Is meditation worth the hype?

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It’s becoming hip to be introspective. Apps like Headspace and Calm have raised hundreds of millions of dollars, and have users across the world. In a hyper-connected world, the ‘contrarian’ thing to do is withdraw yourself from social media and a constant attachment to your phone.

A central part of this is meditation; taking as little as 10 minutes a day to close your eyes and empty your mind, focus on your breadth, and disconnect from the world. These meditation apps offer a nicely-designed interface, a soothing British narrator, and various modules to help with one’s day-to-day struggles. Some are on ‘anxiety’, others on ‘stress’, and one gaining an increasing amount of popularity: ‘sleep’. How effective are these apps and do we need to meditate to be introspective?

In this post, I’ll review my experience with meditation and the various apps, how it has benefitted me, and why I don’t think meditation is necessary to train the mind.

Starting to meditate  

I used to think people who meditated were weird — much like those who did keto or intermittent fasting, and look how well that turned out! The idea that you needed to remove yourself from daily activities and block off anywhere from 10-30 minutes to ‘clear your mind’ sounded folly. Even worse, the concept of using an app to do this sounded like the exact ‘tech trash’ nonsense that I desperately try to avoid (and am often susceptible to).  

Regardless, some turbulence in 2018 (head injury, breakup) pushed me to a limit where meditation seemed like a good idea. I started with Headspace, following the ‘basic’ module of 10 minutes a day, right before bed. Soon after, I added another 10 minutes in the morning, leading to a total of 20 minutes of meditation per day.

Within the first few weeks of starting to meditate, I saw two outcomes that made it seem like a worthwhile endeavour:

#1 — Quality of Sleep

Anyone who lives a reasonably high-stress lifestyle knows how hard it is to ‘turn off’ at the end of the day. I’m incredibly jealous of people (i.e. my dad and brother) who can fall asleep within 5 minutes of going to bed. For me, it takes anywhere from 30 to 90 minutes. I can pinpoint this to a ‘racing mind’ — thinking about what happened during the day, what I wasn’t able to accomplish, or thinking back to awkward experiences that I wish had gone differently (i.e. making a bad joke at work). 

Meditation was incredibly helpful for this. It forced me to focus on my body and let thoughts come and go. This is an important differentiator that I’ll get into later: meditation does NOT encourage you to block out emotions and thoughts. Instead, the idea is to simply ‘observe’ the thoughts that are going in your head, and not ‘chase’ them. With meditation, my sleep noticeably improved.

#2 — Mental clarity

I’m not a morning person, as hard as I try to be. My morning routine typically involves stumbling out of bed, checking my email, and frantically trying to organize my day. Successful people all have their own routines — you can check out The Proof by my buddy Adrian to see how Mark Cuban, Tim Draper, and other entrepreneurs tackle wellness. Meditation stopped my ‘busy mind’ and forced me to settle my body after waking up. This helped me when getting into the office, as (while I still needed coffee) I wasn’t rushing to any specific task or waiting for my brain to ‘wake up’.

I was a Headspace subscriber for a full year, having meditated for 28 hours and sometimes as consistently as 12 days in a row. This isn’t to gloat — I genuinely found that meditation improved my lifestyle and the amount of self-reflection I did. However, I stopped using the apps and meditating in general around 2 months ago.

Meditation isn’t for everyone

I can agree that the mind, like the body, needs to be trained. But like the body, I’ll disagree that there is ‘one right way’ to train the mind. I love lifting weights, but someone can be just as happy (and even healthier) by solely doing cardio or freeweight exercises. Similarly, I don’t believe the mind needs meditation to grow.  

To further explain that, I’ll dive into some of the ‘cons’ to meditation that I found in my year-long journey. There are valid rebuttals to these (that I confront), but I hope this gives some context around how I see meditation. The caveat: with the body, I can refute arguments like ‘your workout isn’t great’ by saying ‘I lift more than you’; unfortunately, the mind is more subjective, so won’t get into that ;)  

#1 Not the universal cure

For physical workouts, there is a time and place for everything. If I only have 20 minutes, I won’t do a full workout, as that might take me more than an hour. In fact, it’s probably hurtful to try doing the full workout, as I’ll feel unaccomplished by the end and possibly even miss muscle groups.  

Meditation is similar; if I had a long day where I’m incredibly tired, I’ll probably be dozing off during meditation instead of doing it properly. For another scenario, if something during the day really irked me, I found meditation to be equally ineffective. I.e. as hard as I tried to ‘empty the mind’, those emotions still dominated my body.

Rebuttal: “Once you get better at meditation, it’ll be easier to do it despite emotions/thoughts”. I think that’s like saying “Once you get better at Crossfit, you’ll start seeing results” — most people won’t make it to the stage of ‘being good enough’, so is it really an effective tactic if the majority can’t utilize it properly?  

#2 Carving time

We’ve all been there: you wake up at 9:15am despite having set alarms at 2-minute intervals from 7:45am through 7:57am. You’re feeling groggy as ever, and the day is off to a terrible start. Let’s meditate?!

No, I don’t think that’s a good mentality. I’m sure it’s possible, but I think it’s weird to grab a phone booth / room and try meditating for 10-15 minutes in the middle of the work day. Another example: work is done and you’re heading on a date, but you have some emotions flowing (anger, anxiety, etc.) that you can’t pinpoint. Let’s meditate on the subway? No, that sounds weird as well.  

Rebuttal: “You have to make time to meditate, even when it’s hard”. That’s how it becomes effective” — again, majority of people aren’t going to put in this level of work. Even with the body, you see benefits from working out + cardio almost immediately. Hard to defend an activity that only gives return after X amount of effort.  

What’s the solution?  

I’m not denying that meditation has its benefits, and can be a great fit for some people. However, I need a solution that gives me the same start & end to my day, while being more versatile throughout daily activities. Maybe it’s in addition to meditation — but there should be another solution.  

And there is a solution: writing. I tell everyone that they should start a blog; it’s an activity of self-reflection that helps you organize your thoughts in a way that’s understandable by readers (aka people with no context). You also get the added benefit of dialogue. I absolutely LOVE IT when people message me about recent posts, sending their thoughts and even challenging me on certain ideas (this one took a lot of heat).

However, I recognize that it’s not the best solution for a lot of people. Maybe you’re scared to put your thoughts out there, for fear of what others might think. Or more likely, you’re not sure if anything you’re thinking is worth reading. I’ll cut the BS — both those fears are probably valid. I put out posts that get 400+ views, and some that take me a few hours to write and get 30-40 eyes on it.  

This doesn’t invalidate writing as a method of self-reflection. Whether it’s a moleskin notebook you keep in your desk or a word document on your computer, writing can be a huge help. It’s the one activity that clears the mind, by dumping everything you’re thinking onto paper (or… screen?). Writing can be a stream of consciousness, a structured argument, or a combination of both. You can also write for 5 minutes a day or 2 hours a week, whatever works for you.

Where do I start?

I recognize that ‘writing’ is a bit too general, and I try my best to make these posts actionable. First, you can check out Writing Well on how to formulate your thoughts in a coherent way (if you’re planning to blog). It takes about 30-45 minutes to get through, and it’s entirely free. I don’t follow all of this, especially since blogging is more of a personal reflection activity for me VS something to gain followers/a brand, but it’s super helpful.  

You can also check out David Perell’s course on writing — it’s more geared towards people who want to become a content creator (blogger, podcast, etc.) but I’ve heard nothing but good things about the course and the outcomes of the students (i.e. published posts for 30 days without fail).  

That aside, here are some pointers on how you can start writing:  

5-Minute Journal

This is by far the EASIEST way to start writing. My friend Kanwar recommended starting a 5-minute journal about a month ago, and I have never missed a day. Sure, I sometimes miss a morning or night, but it’s hard to argue that you don’t have 5-minutes to pull out a notebook + paper and jot down your thoughts.

The journal works like this: you write three headings in the morning: “What I’m grateful for”, “How I’m going to make today great” and “Affirmations about myself”. I add (3) bullet points for each. I.e.

Grateful: A strong friend group, self-control in eating, a flexible work schedule

Great: Hold my fast until 1pm, workout, message (2) people that I really value in life.

Affirmations: “I’m a good son”, “I will achieve my fitness goals”, “I will make time for people that matter to me”.

At the end of the day, you wrap up with another two headings: “What made today amazing” and “How I can make tomorrow better”. See below for sample bullet points:

Amazing: I did XYZ for a client, did 20 minutes of cardio, had a good conversation at work

Better: Make time to write a blog post, plan my calendar in advance, wake up by 730am

I rarely achieve all these ‘daily goals’. It’s also hard sometimes to come up with things I’m grateful for and why today was amazing (if it sucked). However, this ‘micro feedback loop’ is working wonders in my day-to-day. It reminds me of what I set out to do, kicks off + ends my day on a good note, and summarizes how I’m feeling.

Stream of Consciousness

I haven’t really tried this one, but I’m bullish on it. If you don’t like writing, try doing this as an audio recording instead. Whenever you’re feeling a flow of emotions/thoughts, grab your notebook and write / talk for 5-minutes non-stop. This can be ANYTHING: who’s bugging you at work, why you’re disappointed in yourself, what you love about life. Don’t be afraid to ask yourself questions in this ‘stream’ and either answer them or write them down for later.

You’ll find after 5 minutes it’s hard to keep the same thought going. That’s because most of our thoughts + emotions are reactions — once they’re put in a logical framework / reflected upon, 90% of the time they don’t have any ground. The remaining 10%, you can set some ‘next steps’ on what you should do to address the situation.

Conclusion

Meditation is great, I won’t argue against that. However, it’s not the ‘cure-all’ that apps like Headspace and Calm make it out to be. I’d say it’s no more effective than following keto as the #1 solution to losing weight/becoming fit — it might work, it might not, but either way you might learn some things about yourself that inform future activities + decisions.

Do you meditate? What other strategies do you use for self-reflection + keeping yourself grounded? Email me at trevor.sookraj@gmail.com or message me on Twitter or Facebook with your thoughts.

Living or Visiting? (Los Angeles)

One of the live music shows I got to see (Hollywood area).

One of the live music shows I got to see (Hollywood area).

I have a goal of living in a number of cities / countries before I’m old. Not visiting — ‘living’ is a very different concept. Anyone that’s done a Southeast Asia, Europe, etc. trip can tell you that. In the span of 3-4 weeks, you whiz through 5+ countries, countless cities, and try to do as much as you can.

I don’t really like ‘visiting’ places. Even given a full week, I feel like I’m pressured to ‘do things’ with every waking moment. This was the case my first time visiting Los Angeles, in summer 2018. It was a short trip from San Francisco, and those (3) days were packed with tourist attractions, trying new restaurants, and being able to say I had ‘done LA’.

This post is going to dive into my mentality towards ‘living’ in a given area, drawing attentions to the qualms I have with travel and my tl;dr on Los Angeles (spoiler: I wouldn’t want to live here long-term).

What’s the ‘LA vibe’?

In an effort to change things up, I thought I’d try LA for a few months. I moved here this past May, and will be returning to Toronto in the next week. San Francisco left a sour taste of California in my mouth, and I wanted to give the state another chance. LA definitely met the bar!

When you think of LA, you probably think:

Beautiful people, lots of sun, and the epitome of ‘West Coast’ living

What you should think is:

Geographically disperse, good food, tight-knit friend groups

Attractive + interesting people

A lot of those claims are accurate. There are tons of attractive people here, the weather is generally pretty amazing (think 18C to 25C), and the ‘laid-back’ culture is definitely a thing. People value enjoying life here — not to say other cities not, but there’s a certain emphasis on social gatherings, eating well, and being healthy.

I think it’s also well-reflected in the types of people I’ve met here. While there are definitely career-driven people, it’s not like my experience in San Francisco at all. I.e. a person may work in marketing at a creative agency, but I’d be surprised if that came up in initial conversation. Instead, said person might dive into their passion for surfing, yoga, floristry, or countless other topics / hobbies. In contrast, I rarely made it 2-3 minutes into a conversation (if that) where the question “Which tech company do you work for?” came up. Yes, not even ‘which company’, since there’s a 99% chance you work in tech.

This change has made LA very enjoyable. I’ve been to more live music sets in the past 3 months than I have in my entire life, and my immediate friend group (while still tech-oriented, given my interests) includes a doctor and production assistant (film). These people made me realize something about work — a job is simply that, ‘a job’.

That doesn’t mean you shouldn’t work hard, as I’m still very driven to be the top of my industry. However, it means you shouldn’t attach your identity to your work. Starting a company is cool, tech trends are cool, but if it’s hard to talk about anything else in a given conversation, that’s an issue. It was an issue for me a year ago — now I’d much rather chat philosophy (been diving deeper into spirituality recently) or why the Spurs are going to be the hottest team this coming season.

Geographically disperse

Now for the main drawback to LA: everything is VERY spread out. I’m staying in Redondo Beach, which is about 20 minutes south of the airport. Most of my friends live in Santa Monica or Venice, which, while still ‘LA’, is at minimum a 30 to 45-minute Lyft/Uber from my house. This means that meeting up for dinner, drinks, or other social activities is a commitment. That wasn’t the case in San Francisco, where you could walk the entire city in 1-2 hours (ask my mom, she’s done it!).

For many people, this is a big con to the city. However, to my surprise, it hasn’t been the biggest deal for me. I’m very extroverted, which typically meant that I loved meeting up with people & socializing. I realized that my extroversion was largely due to my environment: in college and in geographically dense areas, it was hard not to socialize. Bored on a Friday? Go out with your friends. No plans on Sunday? Grab brunch.

LA made me put a lot more thought into what I actually want to do, given how big of a commitment travelling around LA is. This meant, for the past 3 months, I only did something if I really wanted to do it. I still grab dinner with friends on a weekly basis and hit the bars every ~ 2 weeks, but it’s at a more infrequent cadence than before.

And I love it! I’ve spent a lot more time reading, playing games, and doing other solo activities that I previously ‘didn’t have time for’. I realized what I like doing and which social activities I truly enjoy. It’s improved my self-control and understanding of myself tenfold and for that, I have LA to thank.

Betting on LA?

I’m a fan of Los Angeles, but I mentioned earlier that (despite all the pros) I don’t want to live here long-term. There are a number of factors that go into my decision, but I’ve summarized them below:

  • Family: This is a top priority for me, and my family is based out of the Toronto area. As much as I like the West Coast, a 6-hour flight and 3-hour time difference means a spontaneous weekend trip isn’t possible. Into my professional career, I want to be intentional in making time for family, and visiting 3-4 times per year for holidays isn’t enough for me. LA is too far.

  • Curiosity: I like LA but I didn’t fall in love with the city. If that’s the case, being fairly young, I should endeavour to find a city that I really enjoy. That means trying a lot of other cities that I’ve been curious to live in — New York City, London (UK), Paris, Montreal, the list goes on. One day I’ll settle, but not until I’ve found that (near) perfect fit.

I don’t like travelling

As a final thought, why living VS travelling? Aside from the hustle-bustle I mentioned above, I also believe that I don’t get a good feel of the city unless I’m living there for ~ 1-2 months. For example, with San Francisco, I visited in Feb 2017 and thought I’d want to live there. After living there for a year, I realized I hated it. LA was a somewhat similar story — I loved the city when I visited, now I’m a fan but am not in love with it.

Couple points as to why I think living > travelling when it comes to trying new cities:

  • Impact on routine: If I’m travelling to a city for a week, I’m not in a routine. It’ll feel a lot more like a vacation (which it probably is). Living somewhere means you enter your routine after 2-3 weeks — for me, that’s hitting the gym, shopping + cooking, cadence for social activities, and more. I’ll only know how the city affects that routine after getting into my groove. I.e. San Francisco made nightly activities (i.e. restaurants, board game cafe, etc.) difficult, since the city closes early. In contrast, I’d assume NYC makes nightly activities too enticing, since ‘the city never sleeps’. Seeing how this affects my day-to-day is crucial to how much I like a city.

  • Knowing the ‘locals’: I’ve heard from friends that when visiting cities, they get a good vibe of the locals. I would disagree — it’s hard to really know locals after 1-2 interactions. It’s only when you’ve lived in a city for several weeks/months, will you get to understand their personality, life mindset, etc. For LA, I didn’t realize the wealth divide/inequality and how that affects a given person’s viewpoint on life + work until more than 6-8 weeks in. Likewise, I didn’t realize how ingrained tech was in everyone’s lives in San Francisco until I lived there for a while and could compare.

  • Comparing to tourists: This is a bit of a weird one — when you’re visiting a city, you’re a tourist. That means that anyone you meet who is also a tourist has the same mindset as you: explore the city as much as possible and get the ‘vibe’ of it. After 6-8 weeks, I found my mindset transitioned from ‘I’m just visiting / getting settled’ to ‘I live here now’. That means when friends visited LA, I could better contrast how I felt about the city to how they viewed it (fresh eyes). I think it’s at this point where I can really draw a conclusion about the city.

Conclusion

I hope to ‘live’ in many more cities before I’m old. There are many parts of the world I don’t care to ‘visit’, so I’d much rather plan out future trips with ‘living’ in mind. I.e. if I’m very bullish on France and the UK, why do a ‘Europe’ trip over 2-3 weeks? Why not live in France for 2-3 months and then move to the UK, if I feel the need?

Granted, running my own business gives me the flexibility to do this + work from basically anywhere (need strong internet & working around timezones). However, I hope this post gave some insight regarding my mindset towards travel, and my thoughts on LA. As always, all feedback is welcome!

Building wealth

A big house in Los Angeles.

A big house in Los Angeles.

Millennials aren’t thinking enough about savings and retirement. Articles like this one focus on how fads like ‘avocado toast’ are to blame — my generation loves luxury and living on credit, opposed to stowing away their hard-earned cash.

‘Cash under the mattress’ isn’t the way, however, to build wealth. Instead, many people look to investment vehicles such as real estate and the stock market. This post challenges that idea — I think that in order to build wealth, I need to do one thing well: focus on high-leverage activities that use my skill sets. This article will review my mindset, why I don’t believe in traditional ways of building wealth, and my hunch on why building a business is the best way to do so.

Immigrant mentality

Well, not exactly. I was born in raised in Mississauga, ON (Canada, for all my ‘Murican readers), although both my parents immigrated to Canada as young adults. I won’t go into detail (some background in this post), but I was raised in a pretty frugal household. Lifestyle aside, this shaped my mentality towards money — both the need to conserve it and the drive to earn it.

My parents grinded to be able to raise my brother and I in a financially stable household. Credit card debt, mortgages, and car payments were foreign to me, as my parents prioritized paying everything off ASAP. This was for better and for worse — money (while not abundant) was never a dinner table conversation, however I didn’t learn how to leverage debt.

Our family got burned, like many others did, with our investments (mutual funds) by the 07-08 financial crisis. The only investment vehicle I knew growing up was a Guaranteed Investment Certificate (GIC) account, which typically returns 2% to 3% annually. Put your money in, lock it up for 1-3 years, and forget about it. When starting college, I ventured into the stock market and made some great gains on Shopify, Amazon, and Square (more here). Hurray!

My mindset has changed in recent years. In my opinion, my parents worked hard to allow my brother and I to take risks. I’m fine with calling it ‘privilege’, because in many elements, that’s what it is (earned or not). I don’t have a family to support, wife/kids, or hold much debt (student or otherwise). Hence, I should be open to taking risks in my financial planning, and ‘wealth building’.

My privileged position to take risks means that reasonable gains (i.e. S&P grows 8% annually according to Investopedia) are insufficient. Due to my Type A / Alpha personality, my goal in life is to 10x or 30x the wealth of my parents. Is that possible using traditional investment vehicles?

Real estate, stocks, and ‘traditional investing’

Well, let’s find out! And by that, I mean let’s do some back-of-the-envelope math that explains my thinking. Disclaimer: I’m a Political Science graduate, so this math is far from foolproof. In fact, it may even be foolhardy. If that’s the case, please send me a message before my mom sees this, so I can fix it :)

Base scenario (income)

To make things easier, I’ll set up an example: let’s say my parents have built a net worth of $1MM CAD. My goal, therefore, would be to build a net worth of $10MM CAD or $30MM CAD. To further simplify this, I’m going to lean on a 10-year projection. Keep in mind, the goal of this section is to set up a base scenario, not to be exact with what I would earn (without ‘investing’).

The average business graduate makes around $70k CAD per year, but for argument sake, let’s bump that to $85k CAD. Post tax, this would leave me with around $63k CAD of disposable income (calculated here). I’ll set some parameters below on what my annual expenses might look like:

  • Rent: $12,756 ($1,063 / mo average)

  • Food: $3,396 ($283 / mo average)

  • Entertainment: $5,340 ($445 / mo average)

  • Insurance: $2,722 (quote from AllState on my 2010 Lincoln MKX)

  • Misc: $1,380 ($65 for phone, $50 for gym average)

A total of $25,594 of expenses; leaving me with $37,406 of disposable income. Again, being pretty conservative here — no vacations, buying clothes, etc. The challenge now is to project what my income would be like after 10 years. After some limited Googling, I found some ways to project this…

5 years out — The typical route for many business graduates is an MBA around ~ 2 years in. The MBA takes 2 years to complete, which means my approximate salary (5 years in) would be that of an MBA graduate. Attending a good MBA program means an average salary of $103,024 (see here); to give the same boost I did post-undergrad, let’s go with $125k, or $86,585 post-tax. Minus the same expenses (would likely go up, but for argument’s sake), $60,991 left in Year 5. Again, I’m assuming I’m earning $$ while I’m doing my MBA (usually not true), but bear with me.

10 years out — this one was a lot harder. I’m still on Google (cutting into my Netflix time…), and found a few answers. This Quora article projected average increase in salary, but was somewhat aggressive. I altered it using this Global News article, using a 7% increase for pay raise, 12% for promotion, and 20% for job-switching (aggressive). Using these projections, and a flat rate of expenses, I would make $105,111 post-tax & expenses in year 10.

Option #1 — Investing in stocks

To be realistic (and honestly I did this after calculating the first time), no one invests ALL of their disposable income. It is recommended that you save 20% of your income for a rainy day, or externalities (illness, vacations, etc.). So, I redid the calculations to factor that in (see here)

Using the S&P annual return rate of 8%, and compounding it (I think that’s the word) over a 10-year period, I would have amassed $788,114. This is pretty solid; just by investing and matching the market, I would have saved around ~ 17% more than if I just kept my money in the bank. However, it doesn’t match my optimistic goals — I wouldn’t have even 1x’d my parents’ wealth, 10 years into my career (WITH an MBA). Furthermore, I’m not considering that I would pay tax on the investments I’m making (TFSA contribution maxes at $6k per year).

Counter point: Wouldn’t this compound for the remainder of my 35-year career? For kicks, I calculated that at 8% annual return. I would be left with just over $11.6MM at the age of ~ 67. This assumes I never buy a home, have kids, go on vacations, increase my expenses (since the age of 22…), and invest ALL of my disposable income into the stock market.

Option #2 — Investing in real estate

Most people want to own a home at some point in their life. However, does it make a good investment? Traditional logic says yes — the value of property increases year-over-year, not to mention the rental income that you can make off of it. It does come with a mortgage and down-payment, but you would supposedly surpass that through your capital gains, right?

Time to find out! I have even less knowledge about real estate than stocks, so once again, I’m trusting Google to guide me through it. There are a TON of factors to consider — what type of home am I buying? Is it a condo, detached home, etc.? How many bedrooms?

For the sake of this scenario, I’m going to go with a 2-bedroom, 2-bath condo in Toronto that I can rent out to (2) people each month. According to the Financial Post, this would cost me $558,000 in 2018. Let’s see how that adds up:

Down-payment: $111,600 (20% of the total), which I should have by Years 2-3 in my income projections. So, I’ll assume I’m not investing my first 2 years of income, and be able to make the purchase in Year 3.

Counter point: My parents could co-sign a condo for me, and this would allow me to make the downpayment immediately, paying them interest + only having the cost of the mortgage. I’m not including my parents’ in this model, aside from in my investment motivations, to make matters simpler.

Awesome, I’m a home-owner! And real estate always increases in value, right? Historically, yes — the National Association of Realtors (USA) says it increased by an average of 5.4% from 1968 to 2009. An 8-year projection from 2008 to 2016 saw GTA home prices increase by a whopping 63% (see here). And, if we look at just 2017 to 2018, it only increased by 1.8% in the GTA (see here). So, for the sake of this argument, let’s just use historical price increases — 1.9% annual increase, from 1982 to 2019 (see here). My condo would be worth $636,580 by Year 10.

Counter point: I’m investing in real estate because of the exploding value, what if it keeps going up? Using the 63% growth mentioned above, the condo would be worth $958,440 by Year 10. Keep this in mind!

Mortgage: $28,512 per year ($2,376 per month, according to the same article)

To avoid over-complicating things, I’m going to assume that I do not live in my condo and keep the same level of expenses. This allows me to rent out the entire property, treating it as a true investment vehicle. See below:

Rental Income: $33,732 per year ($2,811 per month, according to this article)

Net-net, I would walk away each year with $5,220 in rental income. Not bad, especially if my post-tax salary in Year 3 is $50,128. Over the span of 10 years, my condo would appreciate an additional $78,580, which is $7,858 per year. So is it fair to say that I’ll make $13,078 per year?

At minimum. This starts at Year 3, and there’s a high likelihood that I will make enough money to purchase additional properties in the span of the 10 years. I tried estimating this, assuming I could purchase a new condo of the same value every ~ 2 years, and make rental income throughout. I would have amassed close to $3MM in property value, and $120,060 in rental income over the 10 year period.

From what I can tell, investing in real estate is a lot more lucrative than putting your money into an index fund. Hiring a property manager (6% of rent; $2,023 per year) means it’s not time-consuming either. Even with maintenance fees, the property value alone is hitting 3x of my parents’ wealth in a 10-year span. This looks like the best option so far.

Remember I said to keep the 63% growth rate in mind? Looks like it would be $3.7MM instead of $3MM, when applied to the same scenario (calculated here).

Option #3 — Investing in… Business?

Okay time for some heavy personal bias, but you’re on my blog, so you signed up for that! I think both stocks and real estate are boring. It’s a way to hold a 9-5 and make ‘passive’ income, in a way that is glorified by the 4-hour Work Week and envied by those who are married to their job. It’s not for me, however, the highest leverage way to build wealth .

The barriers to buying a stock or buying a property are very low. You don’t need operational knowledge for the renting (property management). ‘The market’ and its consistent returns are open to everyone. My dad, who was a mechanic his whole life, trades Shopify in 5-10 day windows, and has 2x’d to 3x’d his retirement savings in the past few years (more on this in a future post).

High leverage activities are ones that make the most of your skill set, and the time you allocate to them. I’m a marketer, which means I have a pretty good understanding of how to ‘grow’ products — direct-to-consumer brands, B2B or B2C software, etc. Should my goal of building wealth not align with the career that I’m building?

I would argue yes. That’s why I signed up for this Micro PE course, that walks you through the nitty gritty of buying a business — including outreach, contract templates, getting financial leverage (read: not your typical mortgage), growing the business, and switching from ‘active’ to ‘passive’ investing.

In the first few videos/lessons, one thing stands out — someone who starts a business needs to figure out product, customers, and make revenue. By buying a business, you already have guaranteed demand, sustain the payback period (i.e. $2k monthly revenue, even if you don’t grow), and get the years of training + labour for free. The challenge? Finding businesses that don’t need daily nurturing (time-intensive), or are already producing high yield due to a good founder (expensive to buy).

Over the next 2-3 weeks, I’ll be completing the Micro PE Course, and I’ll write a review on this blog. Sign up here to take the course with me, or wait until after my review to make your decision. I’ll also be sharing the growth tactics + internal conversations that I have when going through this process — the same one I apply with Abacus Growth, helping companies like Atmosphere, Walden, and PolicyMe.

Will this really deliver more ROI than investing in stocks or real estate? TBD, but I’m excited to find out. Subscribe to my blog for updates!

More disclaimers: Obviously, this post did not delve into the particulars of stocks & real estate, but I hope it did walk you through how I think about them. You can make 150% a year trading stocks, or several millions by ‘flipping’ houses. While I may incorporate those in my wealth building strategy, that isn’t the game I’m trying to play :)

The Keto diet: a 7-week experiment

My best friends for the last 7 weeks. Oh, and  Superhuman , saves me a ton of time.

My best friends for the last 7 weeks. Oh, and Superhuman, saves me a ton of time.

‘Eat healthy, count calories, and exercise’ was the advice I used to live by when it came to trying to lose weight. It makes sense — if you put good things into your body, eat less than you’re supposed to, and challenge your body with weights + cardio, you will look and feel good. Naturally, I was intrigued when I first heard of the Keto diet, which argues you can eat a ‘high fat, low carb’ diet to lose weight and, more importantly, be healthy.

I took the dive on Keto by trying it out for 7 weeks. This post will break down my path to fitness, why I started Keto, my experience on the diet, and overall thoughts now that I’m no longer doing it. If any of that isn’t your cup of tea, feel free to skip — I’ll be posting more tech / marketing stuff soon!

Healthy roots

My parents were health-conscious in raising my brother and I — we rarely had sugary drinks at home, ate a bowl of (cut) fruit a day, and both participated in a number of sports growing up. I personally played several seasons of competitive basketball and soccer, skied, and dabbled in other sports (cross country, hockey, etc.). This meant that, from an early age, being physically fit + healthy was core to how I viewed myself. A lot of good things come from body positivity, but I’m still out here trying to look like Ronaldo.

Despite this, I had weight problems as a kid. Before my growth spurt, I remember my mom having to get 32” ‘husky’ jeans from the US, so she didn’t have to tailor 6” off the regular ones. I thinned out a lot in my teenage years, and only started lifting weights towards the tail end of high school. Throughout college, I experimented with different workouts, took protein, bulked & cut, etc. all to get into better shape.

Some strategies worked better than others, i.e. the 4x4x8 routine helped me get past a big plateau and increase the weight of my lifts by 20% to 30%. Similarly, implementing tactics like intermittent fasting, low carbs (i.e. chicken breast + salad), and counting calories helped me lose around 10lbs (after pic). Other strategies, like ‘bulking’ made me add it right back without seeing any drastic changes to strength.

Granted, a lot of this may have been due to doing a strategy ‘properly’ or not. However, like communism, it’s hard to have faith in a strategy if you’ve never seen it done correctly, or know what’s wrong when you’re implementing it. Therefore, if you’re considering starting the Keto diet, hopefully this post will help with that.

Taking the dive

I follow a guy named Ryan Kulp on Twitter; initially because his company was a Clearbit customer and I was doing interviews, but later due to his funny and unapologetic opinions. Regardless, he started Keto and lost a lot of weight (around 30lbs I think?), despite spending most of his day at his computer, like me. He was so passionate that he wrote a book called Fitness for Hackers — the ultimate guide for those in sedentary lifestyles to kickstart their fitness journey, via diets, workouts, and technology!! (Google Sheets, Trello, Zero, MyFitnessPal, etc.).

I signed up to be an early tester, which meant reading the book, implementing it for 90 days, and giving feedback along the way. I was already curious about Keto, as I met his co-founder who built incredible businesses in Perfect Keto and Kettle & Fire (Keto-friendly). I also am very interested in habits, life hacking, etc., so the mental / energy benefits were also intriguing.

Hence, I took the plunge to start Keto on May 20, 2019, and officially ended it on July 9, 2019. Below, I’ll explain the pros & cons of the diet, my personal experience with it, and my verdict on ‘going Keto’.

Pro — Eat foods you enjoy

I didn’t like doing a low-carb diet when I cut in early 2018; it was miserable, bland, and overall hard to stay motivated. With Keto, dieting became somewhat enjoyable. It’s high-fat, which means I was able to eat things like yogurt, bacon, cheese, etc. The fact that this did NOT affect the success of the diet, and in fact was a central component, made this a pro of Keto. I still had to be healthy — I didn’t eat sweets (sugar), fried foods (carbs), or even fruit (also sugar). However, it was still doable — sample meal below:

Rinse & repeat for every meal! Although avocados are expensive, damn…

Rinse & repeat for every meal! Although avocados are expensive, damn…

Pro — Mental clarity

It’s possible my body is still adjusting, but 7 days after quitting Keto and I’m noticing the differences. I’m definitely lower energy (need 2 cups of coffee VS just 1), and feel hungrier more often. My days are also arguably less productive; I usually wasn’t starving when I ate my Keto lunch, and could get right back into work afterwards. Now, eating sandwiches + carbs, I get into a slump around 2pm and find it hard to get on track.

Pro — Weight loss & strength gain

The challenge to traditional low-carb diets is that you lose strength; i.e. it’s fine for someone who just wants to drop a few pounds, but if I start regressing in the gym, it’s definitely not worthwhile. In contrast, I was nervous that a high-fat diet would actually cause me to gain weight, as is the gut reaction (pun intended). Over the 7-week period, both were proven wrong: I lost weight and was able to lift more in the gym.

Con — Social challenges

Doing Keto means that, while you can eat foods you enjoy, you can’t eat a lot of foods (whether you enjoy them or not). An immediate go-to is alcohol — I could technically drink hard alcohol (i.e. whisky), since it was carb-free (more on this later), but I couldn’t drink beer, cocktails, and even wine needed to be limited. Eating out with friends was tough; a lot of spots (sushi, ramen, etc.) were off the list, and I had to be super careful when I did go to a restaurant, in terms of the sauce they used, vegetables, etc. At first, this was awkward, but eventually it just became annoying and made social interaction a pain.

Con — Skin & bowels

This part is a little gross, as a heads-up… A high-fat diet has implications outside of weight loss, as I was changing the way my body processed food. For starters, I had bad eczema growing up and still have very sensitive skin. A high-fat diet wrecks havock on this, where my skin started to get uncomfortably dry. The worst part was the bowel movements — a high-fat diet can either cause constipation or diarrhea as (if) your body adjusts. Initially, I had minimal issues and used avocados + spinach as my green. After I got ‘knocked out of Keto’, about 3 weeks in, I started to get diarrhea while my body adjusted. That meant the runs 3x per day, for several days in a row. Not fun.

Con — Consistency & consequences

Calorie-counting is a numbers game; i.e. if I eat too much today, I can just run it off tomorrow or make it up later in the week. Even terrible cheat days don’t set you back that much, right? Not with Keto. Once your body is ‘fat adapted’, even eating (1) carb-heavy meal can throw you off. For me, this was Pho after a night out with friends. Following this, despite taking exogenous ketones and eating properly, I was ‘out of ketosis’ for a solid 8+ days. That meant eating a high-fat diet, with no reward, for 8+ days. VERY demoralizing.

Another example was alcohol — despite being allowed under Keto, I developed a pretty low tolerance (no carbs to process it). That’s fine, except for hangovers — I got drunk twice in my 7-week journey, and both resulted in a terrible morning after. Think 5+ hours of stomach pain, throwing up, being unable to move / function, etc. Now I’ve had bad nights out, but both these nights were fairly tame with terrible consequences.

The verdict?

Over my 7-week journey on Keto, I also worked out around 4x per week — twice with a focus on weight-training, and twice where the focus was more cardio-heavy. Results below:

  • Lost 8.8lbs (167.4 to 158.6)

  • Lost 1.9% body fat (15% to 13.1%)

  • Various gains in the gym (bench, squat, curls, etc.)

I’m still going to keep my 90-day commitment by working out consistently, counting calories, and possibly adopting an alternative diet recommended by Ryan. For me, Keto wasn’t worth it — I’m confident I can lose weight by following my initial mantra. However, there are a number of unintended benefits that came from doing Keto:

  • Alcohol consumption: I made a New Year’s resolution to quite drinking entirely, which coincidentally lasted 7 weeks as well. After this and Keto, I can say I’m no longer conditioned to drinking alcohol during meals, social events, or even having the same urge / need to ‘get lit’ on nights out. This is a huge W, as it changes my approach to social situations and what I want from them.

  • Carb & calorie-conscious: Keto made me avoid a lot of foods that aren’t great for me anyways. Fried foods, sweets, and snacks in general are a huge killer to effective dieting and productivity. Moving forward, I might still adopt some Keto restrictions so that I can be healthier and get more out of my day. I.e. eating my lunch in 2 attempts VS 1, so I don’t have the carb-loading slump.

  • Don’t eat unless you’re hungry: Through the Fitness for Hackers guide, I implemented an intermittent fast (16:8) that I still follow, which means eating between the hours of 1pm and 9pm. This made me realized how many times I would’ve ate (i.e. breakfast) without being hungry, or ate as something to do (i.e. snacking, many of which are not Keto-friendly).

  • Have health goals: Doing Keto gave me something to strive for, health-wise. Whether you’re training for a marathon, trying to hit certain weights in the gym, or a small goal like removing sweets from your diet — these all motivate you to keep fitness & health as a top priority. In the future, I definitely want to find other creative ways to do this.

It’s also worth noting that, technically, I didn’t really do Keto right. To do it effectively, you’re supposed to avoid alcohol entirely (drinking stops your liver from producing ketones) and avoid dairy until you’re fat-adapted. I didn’t do either, and this probably took a toll on its effectiveness + my ability to stay in ketosis.

Conclusion

Keto is an interesting concept — I think it can definitely be effective in spurring weight loss (while not diminishing strength), ONLY if it is done properly. If I do Keto again, which I probably will, I would endeavour to avoid alcohol entirely and follow the rules more strictly (re: dairy).

Regardless, weight loss + fitness can be achieved in other ways that are proven and healthy. I like bread, pasta, fruits, vegetables, and other items that are taboo to Keto. I definitely believe I can eat those while being healthy + physically fit. Therefore, no Keto for now!

Disclaimer: None of this is medical or professional advice, but if you decide to try Keto and potentially drastic improve or ruin your life, use my referral code!

Caveat: A big part of quitting Keto was due to my parents coming to visit me in LA this week, where being ‘Keto’ should get me a smack to the back of the head 😂My mom is a nurse and I assumed she would disapprove when I told her (update as of July 17, told her; she does), so now I can live my life in peace!

Vulnerability and genuine interest

Deep conversations — will I be doing this when I’m their age? Will I be white?! Lots of questions.

Deep conversations — will I be doing this when I’m their age? Will I be white?! Lots of questions.

‘Small talk’ is a concept almost everyone is familiar with — it could be with a stranger sitting next to you on an airplane, with a new colleague at a team lunch, or even with people you know well in time-constrained situations.

In sales, it’s easy to game the system around small talk and establishing connection with a prospect. I can shoot the breeze with an older gentleman from the mid-west as well as I could with a young social justice warrior out of San Francisco. Except for the select socially awkward friends we all have, we’re conditioned to read social cues, avoid certain topics, and respond accordingly to co-exist.

My perspective around this has changed a fair amount over the past year, and I want to share my thought process & approach through this post. If you’re looking for a tech / marketing-focused read, this probably isn’t your cup of tea.

Ingrained in leadership

Positions of leadership are acquired through a combination of things — qualifications for the position, passion for the work, etc. Above all, I’ve found that many positions are secured via respect and admiration for the individual — you want to be associated with them, hence it makes sense to put them in a position of leadership where being a follower / subordinate brings a sense of pride.  

In my high school days, I was heavily involved in student politics. Voting was obviously a key component of this —being recognized and liked by a wider audience. For students looking to get elected, this meant meeting as many students as possible, and establishing a minimum level of rapport with them that would elicit a vote.

This continued into my college days, where ‘leadership’ positions required a base level of competency but were still largely a popularity contest. Network, build rapport, climb the ladder. This spilled into my social life as well — I found it difficult to spend too much time with one friend / friend group, since I always wondered what the opportunity cost was of doing so.

This made it very difficult to build deeper relationships, since I never knew one person well enough to be vulnerable and share what was really on my mind. It started with ‘How are midterms going’ and transitioned to ‘XYZ sucked at work’. To clarify, I was far from a loner; I had plenty of friends, but the majority were functional — i.e. enjoyable in the context they were made (during work, men’s soccer, etc.).  

A generational problem

I’m convinced this is an issue that plagues the younger generation, due to ‘instant communication’ and online connection. I have the illusion of lots of friends (i.e. on Facebook), and even for people I would consider true friends, I have the illusion that I’m up to date on their lives (i.e. their Instagram stories).

What’s the effect of this? For starters, it gives me the impression that I know how someone is doing VS how they’re actually doing. I think this plays strongly into the rise of poor mental health in young people: I.e. ‘yes I know you went to New York City last week, but what was keeping you up while you were there?’ or ‘Congrats on getting into law school, moving across the country will be fun! How’s your relationship with your parents?’.

These are deep questions, and to be fair, I wouldn’t feel comfortable asking them with 95% of the people I know… Is that not a good thing? There’s only so many hours in the day, why not spend them building deeper relationships with the 5% that matter the most to you?

From a different lens: A friend recently told me that he only keeps in touch with (5) friends from college. That shocked me at first, but it made a lot of sense. You’re obligated in certain environments (work, school, etc.) to interact with people and even be ‘functional friends’. It’s only once you leave this environment do you have to reflect on who you want to keep in touch with. Unfortunately, at that point, it’s too late to invest in the relationships you value if you haven’t already.

How I’m changing my behaviour

As the title says, there are two things that I started focusing on in the past year (even less) to develop a stronger support base and deep relationships. I’ll break them both down, in terms of my approach + how I built up to tackling them directly:

Genuine interest

I’m guilty of not letting people finish their sentences. Not in terms of cutting them off (mansplain), but more that I stop giving them my full attention about 60% through and start thinking of my response. This is typical in a ‘networking’ conversation — you want to show the person that you’re listening to them, while also trying to accomplish your own agenda (i.e. feel out for referral if job, or potential client).

My goal in the near future is to eliminate this tendency and focus explicitly on taking a genuine interest in the people I’m chatting with. If they’re boring, and I realized I’m not actually enjoying the conversation, I should either dig deeper or end it. If not, it could yield some very interesting conversations where I learn more about a person + their passions, along with better understand my interests and what I want to discover.

Vulnerability

With genuine conversations comes a deeper sense of connection; strangers become acquaintances and eventually good friends. The second step in this path is to focus on being more vulnerable with people I consider ‘good friends’. How often does someone ask you ‘So what’s new?’ and you immediate jump into a recap of your week? For me, catching up often entailed this, and it made me dread the conversation after 5-10 minutes, even if it was with someone who I would consider a ‘good friend’.

My goal is to increase my level of vulnerability with people who I want to develop deeper connections with. There are a few stages to this that I’m going to try, to help ease myself into this new behaviour:

#1 Starter questions

Switch from starting conversations with ‘What’s up?’ to ‘How are you feeling?’ — this should immediately change the nature of the conversation and skip the formalities / small talk that usually take up the first 5-10 minutes. Shorter interactions will be more fruitful, or spur on future longer conversations that wouldn’t have been had otherwise.  

#2 Flow of consciousness

Recently, with people where I’m looking to be more vulnerable with, I’ve stopped worrying about how I articulate a thought or feeling. I.e. instead of saying ‘I’ve been having trouble with XYZ’, I switch to ‘XYZ is tough, here’s how I’m feeling, and what I’m thinking — does that make sense?’ This way, I get them to engage with what I’m going through VS just commenting on it from their perspective. It creates a bond, so you don’t feel like you’re tackling anything alone, with the other person ‘spectating’.

 #3 Intentionality

I think in many cases, I’m afraid of vulnerability due to the fact that it might involve placing a burden on someone else, or taking someone else’s burden. A friend goes through a break-up, and the default response is “I’m here if you need to talk”, but I rarely follow up on that. This may be the excessive planner in me coming out, but wrapping up conversations with next steps (either with the person, or on my own) can be helpful.

#4 Cadences

It’s tough to keep in touch with people, so why not plan it out? Building on my obsession with Google Calendar, I’ve started scheduling recurring ‘catch-ups’ with my friends. They can last 30-60 minutes, and range from as often as weekly to monthly. Some are structured, but the majority are open-ended — with the goal of voicing anything that’s on our respective minds. I’ve pushed them back, had conversations earlier than planned, etc. The goal is just to get into the habit.

Conclusion

Life is too short — every interaction should spur feelings, questions, and overall just feel worthwhile. I believe this begins with shrinking your ‘network’ and support base, making it exclusive to people you want to engage with and develop a deeper relationship with. This is followed by being intentional with vulnerability and taking a genuine interest in their respective lives.

This is not to say that networks and acquaintances are not important. A lot of relationships will continue to be functional in the context of work, sports, etc. However, as long as I’m being intentional with the close relationships that I’m fostering, I think I’m on a path to living a good life.

 This post was inspired by The Art of Happiness, a gift I received from my friend Steeve, and from starting a 5-Minute Gratitude Journal (adapted), which my friend Kanwar told me about.

Community is everything (All DRF 2019)

drf_squad.jpg

When I returned from San Francisco back in September, I was honestly a little lost. I knew I wanted to build something, as many people do, but as all entrepreneurs know, the road is rough and lonely. Most of my good friends had full-time jobs, or were actively looking, whereas I was thinking of which problem space interested me and how I would go about building a business to address it. This wasn’t a more ‘noble’ or ‘purposeful’ path, but simply the one I felt was the best fit for me.

Trying to build something is not a fun headspace to be in, but one thing changed that — joining Dorm Room Fund (DRF). Since coming onto the team in November, I’ve been surrounded by highly motivated people, many of whom are trying to build their own business. In this post, I’ll dive into my experience with the organization thus far, my experience at our annual retreat (All DRF), and how that all fits into ‘community’.

What is DRF?

In 2013, Josh Kopelman and the team at First Round Capital (FRC) decided to make a bet. They saw that some of the hottest tech companies were being started by college founders, many of whom dropped out to build their business. This didn’t have to be the case; college is an incredible time in your life, whether that’s undergrad, MBA, or a different stage. The access to professors, resources, and like-minded students should incubate the greatest ideas. FRC wanted to improve the experience of building in school by funding student founders with a $20,000 pre-seed cheque.

The DRF team is essentially split into two parts — investment and operations. The former consists of ‘investment partners’ in each of our investment cities (Boston, NYC, Philadelphia, and San Francisco) that attend school in that area. They source deals from surrounding schools and make decisions on whether DRF should invest. The latter, operations, consists of partners that support DRF in a specific capacity, as well as DRF portfolio companies. I joined this team to help with marketing alongside my co-lead, Phillip, however there are other roles for engineering and design.

It was rewarding getting to share my marketing / growth ideas with our portfolio companies, and see them implement that into their planning. It has also been a blast getting to run DRF’s brand via social media, blog posts, and other cool initiatives in the pipeline. However, that’s not the point of this post; the best part about DRF has by far been the community.

‘The G.O.A.T.’

Ever since Tom Brady staged an incredible comeback to win the Super Bowl, the term GOAT (Greatest of All Time) has been thrown around in increasing frequency. It spilled into non-sports related conversation in reference to other incredible people, i.e. ‘That movie was amazing, DiCaprio is the GOAT’, and later spread to products and inanimate objects: ‘I’ve never felt so organized, Notion is the GOAT’, finally culminating in daily use for simply accomplishing a task (see below):

goat_msg.png

How does this relate to DRF? Well, as cocky as it might sound, I strive to be the GOAT. I want to be the top in my field, have drive and grit that pushes me beyond the crowd, and inspire others to do the same. At the same time, I’m human — I’m prone to sleeping in, being comfortable in complicity and/or mediocrity, and being risk averse.

Community is a big indicator of success and potential. I prefer to call it ‘tribe’; the people you heavily associate with, who project and reinforce your value system, challenging you to strive for new heights. I try to surround myself with people who are at the top of their game, but this is rarely in a contrarian sense. Top = coveted job that everyone is striving for. This unfortunately creates a culture based on achievement; people who obtain these jobs have ‘made it’, and it becomes difficult to break the chain and continue to challenge yourself. I’ve seen this become an issue for people in their mid-20s, who face existential crises on whether they’re pursuing a career based on their values, opposed to one that validates their value choices.

Enter the DRF community: partners that hail from Ivy League schools and coveted MBA programs, all of whom were already at their top of their game when joining the DRF family. In just (6) years of existence, past DRF partners have gone on to become partners at top VC firms, start and run companies worth $100M+, participate (and graduate from) Y Combinator, and, as many high-caliber people do, work at those highly coveted jobs in tech, finance, and other fields. The difference, which I’ll dive into later in this post, is that they possess the drive to relentlessly pursue experiences (job-related and not) that get them one step closer to self-actualization.

3 Takeaways from All DRF 2019

Last weekend, I had the pleasure of attending DRF’s annual retreat, All DRF, that brought together 70+ current partners, alumni, and allies of the program for programming, updates, and team bonding. This was my first exposure to the full team and alumni in-person, and for an extended period of time, hence it’s the focus for this post. Below are some key takeaways I got from the weekend, which I think are universally applicable to any community / tribe.

(1) Support & Challenge

This past year, I witnessed a number of friends get new jobs and make big life decisions. In the process, they were supported by close friends who helped them prep, and made introductions for them that would increase their chances. This is typical of any strong community, built on a backbone of support. If these jobs were conventionally attractive (i.e. high-paying), or life decisions that were expected (i.e. moving for high-paying job), a pat on the back was automatically extended.

DRF is similar, in the continual openness and support offered by the community. The difference is that, in my experience, a ‘pat on the back’ is never automatically extended. You got a great job, kudos, but why are you taking it? It felt natural to get that outcome; what would be unnatural AND give you the same sense of gratification? Challenging your closest friends and urging them to share their thought process is crucial to building a strong and hungry tribe. It avoids confirmation bias and increases the probability that you’re pursuing the path of greatest return, not the one of least resistance.

(2) Search for diverse perspectives

I’m a marketer, which means my views are largely shaped from a ‘business’ lens. Most of my good friends are in business-related roles, i.e. finance, sales, etc. The majority of them also received a business education. This creates a homogenous worldview, despite efforts to diversify. Building on the previous point, a homogenous group can only challenge themselves to a certain extent; it is impossible for them to ask questions or approach problems in a way that is alien to their foundation.

DRF is bonded by a love for tech, a knack for building, and an interest in venture capital. This brings together a smorgasbord of people — engineers, researchers, MBAs, and more. Some partners are freshman in college, others are 10+ years into their career with multiple degrees. This range of perspectives means I can have the exact same conversation with a couple different people, and each goes in a very different direction.

Example: Over the weekend, I asked a few people how they reconcile their values with their work. I’ve tried this in the past with other circles, and it was usually met with ‘that’s a good question!’ or ‘I’m still trying to figure that out’ — the former forgotten a few minutes later and the latter met with no plan of action. At All DRF, this was rarely the case; in fact, I’ll list a few (summarized) views below:

  • Person #1 — Believes that you can reconcile your career with your value system, and pursue a career that fulfils it. I.e. social impact investing for someone that wants to make a difference. Reasoning: had an earlier near-death experience and seeks something more from life (work and personal).

  • Person #2 — Believes you don’t have to reconcile career with value system. Work is a natural motion and trying to find value in everything leads to misery. Reasoning: runs their own startup, is possibly already fulfilled to a certain threshold?

  • Person #3 — Believes that value system and career are mutually exclusive. Being challenged in work does not (always) mean being challenged in values, should aim to realize that through personal relationships and pursuits. Reasoning: wants to be a chef but works in tech, hard to aim for a convergence of the two paths.

This is just one, specific example, but there are many more that happened throughout the weekend. I.e. talking about starting a company yielded different results — one did it while in school, another dropped out, and another left a highly coveted job (Google APM) to pursue it. Tl; dr is that intentionally surrounding yourself with diverse perspectives gives you more to compare against when introspecting, and (in my opinion) gives you an enriched worldview. Can’t find these perspectives? Force yourself into situations (and communities) that will provide them.

(3) Never stop having fun

All this talk about career planning, optimizing for learning, and other cliches bring one thing to mind: hustle porn. The LinkedIn and Instagram ‘influencers’ that talk about ‘never stop grinding’, that laugh at the idea of work-life balance and idolize an unrelenting hunger for productivity. I hate this; it’s toxic, suppresses vulnerability, and makes you feel less valuable if ‘grinding’ is not your #1 priority.

At All DRF, after the workshops on venture investing and recapping DRF initiatives, we had fun. Everyone, regardless of age and stage of life, enjoyed decompressing through bowling, basketball, and even flip cup. I loved this part about All DRF, and to know my community values this balance, as it reinforces the notion that your career — synonymous with ‘hustling’ and ‘grinding’ — is only one part of your life. Personal relationships, hobbies, and, to put it bluntly, things that make you happy, comprise the rest. I believe that any successful community, and one I’d want to be a part of, should promote having fun and building relationships (note I said relationships, not connections or a network) as a core tenet of their membership.

Conclusion

Like many of the recent developments in my life, DRF was not ‘part of the plan’. Last summer, in San Francisco, I went to a NavTalent speaker event that my friend invited me to. In the pizza / drinks part of the evening, I met an Asian dude with impeccable style who was a design intern at a tech startup. After grabbing beers a few days later, he mentioned that a group he was a part of (DRF) was hiring for a new marketing partner. A few months later, after applying and interviewing, I joined the family.

I can’t thank DRF enough for taking a chance on me and welcoming me into their family. As with many other communities, it’s what you make of it — and I hope I can maximize my contribution in the time I have left. If you’re looking to improve student entrepreneurship on your campus, or if you’re a student starting a venture and looking for funding, drop me a note at trevor@dormroomfund.com :)

Race, Culture, and Heritage

skintone.png

Slack, a messaging tool for groups and companies, broke social norms when they announced users could change the colour of emojis, like ‘thumbs up’ or ‘raised hands’. Rightfully so, they were celebrated for giving users an opportunity to react in ways that truly represented who they were, and didn’t default to a bright yellow tone (think most smile emojis). For me, it sparked an internal debate around who I associated with racially, and how I choose to portray myself on a day-to-day. Talk about an ‘aha!’ moment for a product, am I right?!

This post will primarily go through my thought process around race, culture, and heritage, including personal experiences and how I see the discourse.

Being Canadian

About 2 weeks ago, I was staying with my parents in Mississauga and visiting some friends and former colleagues in Toronto. I missed the GO train and my dad was generous enough to drive me to the subway station. He also flagged down another man, probably in his late 20s, offering to give him a ride.

In the car ride over to Kipling, the man revealed that he worked in Toronto and had immigrated to Canada about a year ago. When asked about my dad’s path to immigration, he proudly revealed that he had been in Canada for 40 years. As someone born and raised in Canada, this didn’t initially register to me. My dad came to Canada at a relatively early age from Guyana (a Caribbean nation), and spent the entirety of his adult life in this country. He has an accent, a ‘brown’ name, and is of a dark brown skin tone. He also listens to Kenny Rogers, dresses in typical ‘Canadian’ clothes, and has fully adopted this culture.

My mom came to Canada at the age of 17 from Goa (India) — a Portuguese colony. Her maiden name is Portuguese and she was raised Catholic. Coming at such an early age, she too has ‘grown up’ in Canada — we bond over ABBA and Jim Croce more than any ‘brown’ music, and she makes the meanest lasagna, salmon casserole, and chicken divan that I know. Like my father, she too has a ‘brown name’ and an accent, but a very light brown skin tone.

Fast forward to marriage and having kids — my name is Trevor and my brother’s name is Richard. I grew up skiing and speaking French (via the immersion program) and listening to Nickleback and Greenday. I don’t know any ‘brown’ languages, I’ve never been to India, and, to be honest, I don’t identify with the culture at all.

Unpacking identity

I see posts on Twitter and Facebook go viral around people taking pride in their culture. The word itself, ‘culture’, is worth unpacking as well. To me, it embodies the norms and symbols (language included) that I most identify with. Culturally, I’m Canadian, through and through. This hasn’t raised much debate, and rightfully so.

The word ‘heritage’ is harder to come to terms with. To me, it doesn’t represent so much the culture you identify with, but rather your cultural background. My father’s side of the family is predominantly Hindu — I grew up going to brown weddings, jhandis, and participating in those ceremonies. My father, brother and I all showed up to these events in jeans and a polo — I didn’t have any of the traditional garments. However, this was my ‘heritage’. It felt foreign and was difficult for me to reconcile with.

In contrast, my mother’s side of the family is Catholic and I was raised Christian. Some of my earliest memories are linked to Sunday School and worship songs. This is a big part of my heritage, as it is tightly aligned with my mother’s background. However, it is very far from being stereotypically ‘brown’. I don’t have any memories of distinct ‘Indian’ experiences, aside from the occasional food item that makes it into a family gathering.

Finally, there’s the concept of race. To me, this refers to your ethnicity, and is determined more by what others see you as than what you see yourself as. This isn’t much an issue for me — Caribbean nations were populated by Indian slaves, with the colony of ‘British Guiana’ coming to be in 1831. Likewise, the former Portuguese colony of Goa was thoroughly Indian before it was conquered. Therefore, despite my colourful heritage and cultural overlap, I’m ethnically Indian.

I’m not sure how this works for people who are of mixed race, i.e. half-white (Caucasian) and half-black (African-American). There’s also people who claim a variety of racial backgrounds, such as being 1/8 Chinese and 1/16 indigenous. If that person looks white, are they racially classified as Caucasian? Does it really matter if they can still claim other elements in their culture and heritage?

21st century flaws

Growing up in Canada, I never found racial tensions to be that pronounced. Yes, I understood the positive and negative stereotypes associated with being ‘brown’, along with the possibility that some people might discriminate against me. However, I can’t think of an explicit time that I experienced direct racism — the stereotypes were often a joke or in reference to an episode from The Simpsons than an experience that would shape my personality and worldview.

One of the most confusing encounters I’ve had with race and heritage was several years ago in applying for American colleges. There was a detailed section where you needed to indicate your background, which referenced region (i.e. South Indian, Latin-American, etc.). Naturally, I selected both South Indian and Caribbean. Opposed to getting an ‘Indo-Caribbean’ option following that selection, the only option I could select was ‘African-American’. I asked my father, and he mentioned that he had a similar experience in immigrating to Canada back in the 1970s. The overlap in how we see ‘race, heritage, and culture’ in comparison to how various institutions define it and causes a great deal of confusion. Some of these inconsistencies, decades later, have yet to be corrected.

How this all relates back to community is what I’m most interested in. Culturally, I’m stereotypically Canadian and therefore a lot of my friends reflect that. Naturally, a great number of those friends are also Caucasian. This has rarely caused any discomfort for me, as our interests, tastes in music, and even sense of humour are very similar. Race plays a factor, as does heritage, but neither are as salient as culture.

In contrast, I have a number of ‘brown’ friends, but the sense of community isn’t nearly as strong. I don’t get all the jokes, mid-sentence switches to Hindi, and cultural nuances. I’ve taken heat for not being able to recognize a Sanskrit tattoo or for having a look of confusion when someone tells me what part of India they’re from (‘That’s North right? Close to… Bombay?’). An experience that shook me quite a bit was while I was in San Francisco and met my roommate’s (also brown) friends at a party. I introduced myself as ‘Trevor’, and immediately they asked ‘but what’s your real name?’. After a few minutes of back-and-forth, including a point where I pulled out my driver’s license to prove it, the conversation ended with ‘sure, whatever you want to go with’. I don’t blame this person, but it really questioned my identity and whether I take enough of an interest in my background.

The intersection between these two groups (culturally familiar and racially familiar) brings the idea of ‘assimilation’ into the discussion. Many viral debates and movements are centred around governments and institutions trying to stifle cultural expression and have those individuals adopt what is ‘normal’. I never had to assimilate, since Canadian culture has always been what’s most familiar. For my parents, however, I wonder if there were instances where that shift to Canadian culture was a conscious decision — and whether Canadian culture really fit our family more than our respective pasts.

Conclusion

Race, culture, and heritage are all distinct concepts that influence my day-to-day life. They dictate the way I present myself (language, clothing, interests) and the people I associated myself with (community, tribe). I’ve been making an effort to take a greater interest in my heritage, as I think it’s incredibly important and something that should impact how I define myself as a person. I often wish I could speak an Indian dialect (i.e. Konkani) or that I felt more tightly associated with my heritage. While neither of those are possible without a ton of force, at this point in my life, what is possible is making an effort to learn about it.

For any first-generation or second-generation individuals asking the same questions I am, I’ll finish with this: race is a given, culture is what’s familiar, and heritage is up for discovery. Take the time to ask your parents and relatives about these experiences, as those experiences are a significant part of you as a human being. Definitely something I’ll be digging into for 2019!

Being 'over-productive'

Air Pods are peak productivity(?) (via  Unsplash )

Air Pods are peak productivity(?) (via Unsplash)

I’m not ashamed to say that I’m obsessed with life hacks and productivity. I swear by Google Calendar, use Notion for organizing my to-dos and thoughts, and feel pretty disappointed when I wake up past my goal of 8:30am.

I have conversations with friends about how to be ‘more productive’. Some things, i.e. meditation and hitting the gym consistently, work wonders for my productivity. Others, like intermittent fasting and blocking time, haven’t been as effective. Regardless, it fires me up to think there’s someone out there working harder than I am and achieving more, while I’m sitting idle.

In this post, I want to explain my approach to being productive, how it’s changed over the years, and why I strongly believe there is such a thing as being ‘over-productive’ — it can be toxic, and my generation is most susceptible to it.

It’s always a race

I went to a high school with regional programs (i.e. IB), so competition was ingrained early. It wasn’t a question of whether you got honours, but rather how well you did relative to the rest of the class. Classmates were heavily involved — leading clubs and extra-curriculars outside of school, playing on competitive sports teams, the list goes on.

I fell into that, and it stuck with me — all my friends were shooting for (and getting into) the top programs for their respective interests. Fast-forward 4 years and those same former classmates are in med school, working software engineering jobs in Silicon Valley, or grinding at top consulting or banking firms. Simply put, it’s not special to be an over-achiever, the question is to what extent you can take it.

College was a similar story, but instead of getting top executive positions in school clubs, it migrated to getting top internships at coveted companies. Friend groups began to shift apart, and I increasingly tried to associate myself with people who were always on the look-out for new opportunities, hustled hard when given the chance, and often sacrificed health (mental & physical) to get there.

Conversations were (and still are) very predictable. “What are you up to for the summer?”, “Did you sign full time?”, “How are grad school apps going?”, and countless other questions that solely related to your position as a student and success towards (supposedly) objective career goals.

The working world

Things changed when I started working full-time at Clearbit. The majority of the company was in their late 20s or early 30s; anyone who was caught in the rat race of being ‘furthest ahead’ burned out by 25 and had since found a proper balance, while those that were late bloomers found their footing and were well content with their life — both career related and not.

I was shocked to be in this environment, and to be honest, a little lost. There’s hustle porn galore in The Valley, but I increasingly started to realize that your job was only a fraction of your life. I.e. your friend group, the city you’re living in, and what you do / think about outside of work is what shaped you as a person.

The sheltered environment of college and highly concentrated interest groups make for a rough transition to the ‘real world’. Example? I work in tech, read tech, and talk about tech a lot. This is fine in college, and a large part of my friend group is very engaged in tech. Entering the work world, even people I looked up to a ton, with regards to their tech knowledge + career, never wanted to talk about it outside of work. My job is not what defines me as a person, no matter how much I threw myself at it.

Over-productivity

The idea of being ‘as productive as possible’ marks the transition of college/young professional life into what could arguably be regarded as ‘full adulting’. I’m guilty of all the cliches; I tried intermittent fasting, I still meditate fairly frequently, and I’ve used grayscale on my phone, Moment, and deleted apps like Instagram and Facebook to maximize productivity.

I can confidently say this isn’t living; life loses its zest when all your activities are reduced to a slot in Google Calendar or related to how it positively or adversely affects your productivity / career progression (trackable by a spreadsheet). So with that in mind, I’ve tried making a conscious effort to dive deeper into my hobbies and interests, making decisions that don’t optimize for productivity, but instead for experience.

Example — I could stay in on a Friday night, grab a coffee and my laptop, and meticulously work on building a company. I could also ditch the laptop, hit the bars to hear live music with my friends, many of whom I may never see (ever, or for a prolonged period of time) after a few weeks when we part ways.

Conclusion

There’s a beautiful simplicity to taking goals & objectives off your day-to-day, and instead being intentional about enjoying life. Not to say that being driven is a bad thing, or that goals should go out the window. But the minute that they drive every decision I make and result in me missing out on experiences I otherwise would not have had, is where I have to draw the line.

The crisis of choice

Now THESE guys knew how to make decisions. Or relentlessly colonize the world. Maybe both!

Now THESE guys knew how to make decisions. Or relentlessly colonize the world. Maybe both!

Merely a few decades ago, religion had a strong hold on society. While the Enlightenment had long since passed, and church and state were clearly separated in most developed nations, many would still have considered themselves ‘religious’. Around 81% of Americans identified as white and Christian in 1976; that number has since fallen to 43%.

Secularization, in the face of globalization and an increasing access to technology, has created problems that did not previously exist. In this post, I want to un-pack what I understand this shift to mean. Tl;dr is that secularization is not intrinsically a bad thing, but the lack of change in other aspects of society is. And for anyone about to close the tab, I’m not preaching that religion is/is not a good thing, nor that you should / should not convert — that choice is up to you! This is purely a thought exercise to flesh out my thoughts and why I view the world the way I do.

A solid foundation

Religion, across the board, is a great source of values and morals for the average person. Many religions, and as a Christian I’ll speak primarily to that, preach the importance of community, loving thy neighbour, and being honest and void of temptation (alcohol & other influences).

They also preach a specific way of life that adheres to their vision of a perfect world. This comes with gender roles, denouncing certain types of behaviour (read: social conservatism), and often altering the world order from its current state. Cue debates on whether abortion or homosexuality should be made legal or not.

In an era where religion was extremely salient, many individuals could lean on religion as reasoning for their beliefs and decisions. You didn’t need to justify why a certain viewpoint was valid, you could simply state that it says so in scripture. This alone may not sound like enough — however when the majority of the country is religious, mounting an opposition is challenging.

Over the years, this dominance eroded; not just in the population as a whole, but especially in youth. Exposure to The Internet meant you no longer had to rely on your parent(s) to develop a worldview, which included your view on religion. Why ask Mom why the welfare gap exists when you could ask Google?

The challenge to this is lack of guidance — someone between the ages of 8-15 doesn’t have a de facto system for browsing The Internet and discerning what is real/fake. More importantly, there is no system for discovering what path they need to pursue in order to live ‘The Good Life’.

This used to be provided by religion. When you were lost or unsure of how to act, leaning on religious values or even scripture itself was the solution. The rise of secularism frowns upon that — as an individual, you should pride yourself in being able to reason over everything else.

The education gap

This phenomenon doesn’t just affect youth, but adults as well; perhaps even more. While youth had little guidance on how to form their world view, adults had little guidance on how to alter their world view. As mentioned above, previous arguments that used religion as reason could no longer be accepted. An adult in 2019 needs to be able to justify their world views using reason.

I’ll be the first to admit that I’m not always the most reasonable person, agreeableness aside. Although I try to ‘logic’ my way out of most decisions and scenarios, emotions get in the way and my judgement can sometimes be clouded. Don’t believe me? I’ve written full posts on regret and decision-making to rationalize (to myself) why I operate the way I do.

While I do falter on occasion, I’d like to think I’m quite capable of thinking critically about decisions and coming to reasonable conclusions. I don’t know if this is true for the majority of people — especially those who may be less educated. A prime example can be found in fake news: how many people are guilty of reposting (and/or commenting on) something they didn’t verify as factual? Worse yet, how many people are guilty of doing this without verifying if it was factual?

Niche news outlets and pundits allow for your typical individual in 2019 to consume content that solely affirms their views and beliefs. If I was socially conservative (I’m not), then following Fox News and selectively listening to Jordan Peterson and Ben Shapiro could be enough to get by. I could find justification for anything I believed in, without needing to explain my reasoning.

I blame education more than anything for this phenomenon. For starters, the K-12 system is more interested in teaching history and biology than it is with teaching financial and digital literacy. As much heat as liberal arts degrees get today for producing ‘unemployable’ graduates, the benefit is that they teach you how to read, not what to read. Being able to identify the bias in an article, find comparable pieces, and come to a conclusion on your own is the essence of critical thinking.

For adults, this problem compounds. Most adults aren’t in an environment like K-12 or post-secondary education where they are forced to learn. 24% of Americans haven’t read a book (even in part) in the last year. For those that never developed the ability to reason and filter information — whether due to dependence on religion, lack of education, or other factors — are lost in an age that throws more information at them than ever before.

‘Societal norms’ aren’t helping this. The minute I identify as conservative (I do), a whole swath of people shut their eyes/ears like they are in a terrible combination of Bird Box and A Quiet Place. People are afraid of debate, whether due to micro aggressions and fear of conflict, or simply because they don’t want to rock the boat. The value of ‘reason’ that led us to the Enlightenment is being shunned in an age where we are more developed than we ever were.

Steps to reason

This is usually the point in an article where I have a solution that gets me high fives from a handful of friends (and my Mom), before stumbling into a conclusion. Unfortunately, I don’t have the answer to this ‘crisis of choice’, but I have a few ideas:

1) Re-evaluate

Set a timer for 5 minutes and write a list of statements that you believe to be true about the world, including about yourself. Look at those statements and find reason as to why they are right/wrong. Then, challenge yourself on your reasoning. For some points, you may have no qualms. For others, you may furrow your brow, urging you to dive into that topic.

2) Read & write

Find areas of interest and read a lot about them. Philosophy, finance, politics, gardening, whatever you fancy. Then write about it — leverage the monster we call The Internet to organize your thoughts in a way that is presentable to a general audience, and invites discussion around it. This post took me about an hour and had me researching statistics on religion and reading to either challenge or validate my points.

3) Debate

I have a number of strongly held opinions — corporate jobs suck, everyone can get experience + money while in college, and sales is an underrated career path. None of these opinions are universal, that much is obvious. However, it’s not until I put my thoughts out there (and have them challenged), that I either further validate or invalidate them. For example: corporate jobs don’t suck, they’re a great outlet for people in tough financial situations, specific paths (i.e. doctor), and/or technical routes (i.e. engineer).

Conclusion

The dominance of religion throughout the 1900s allowed many to lean on it as reasoning for their values, morals, and the basis of social order. Through challenging the status quo, society was able to progress to guaranteeing basic human rights and equality to a larger group of people (i.e. ending apartheid + segregation, allowing gay marriage, etc.).

Increasing secularization and The Internet brought an influx of information and variance of choice that requires the ability to reason and think critically in order to come up with valid opinions. Most people don’t do this, nor do they need to.

Aside from a shift in education, individuals need to re-evaluate their existing views, read to answer lingering questions, and write + debate to further improve their understanding of the world. Failure to do so will further embed a culture of toxicity and fear that has already polarized a number of nations (i.e. USA).

Thanks to Phillip and a few other friends for sparking this idea and giving their thoughts. As always, if you disagree or have a strong opinion, please message me!

Corporate jobs

Brad and Chad celebrate the launch of their new marketing campaign, which was ready 6 months ago but had to get approved ( via Unsplash ).

Brad and Chad celebrate the launch of their new marketing campaign, which was ready 6 months ago but had to get approved (via Unsplash).

I posted a tweet this past week that took a fair amount of heat around choosing startups / riskier roles with high upside compared to ‘stable’ corporate jobs. In hindsight, it was a generalization, although that’s hard to avoid in 140 characters. Hence, I decided to put together this post to dive into it in deeper detail.

The gist of this post is that, in general, as a new graduate pursuing a career in tech and/or with an interest in entrepreneurship, you are better off working at a startup than a large corporation. Is this a ‘hot take’? Of course — but it’s something I feel strongly about, and look forward to being debated on.

Disclaimer, exceptions, externalities…

I’ve watched a ton of debates and lectures on politics, philosophy, and other topics of interest that are fairly polarized. In the Q&A, there’s always someone that comes out with an ‘edge case’ on why the argument the presenter was making is wrong. I.e. if I make the argument that an area marked ‘danger, do not enter’ should stop people from entering. Someone may retort ‘what if the person is blind and/or can’t read’. That is valid, but it’s an exception to the rule, and a minority / ‘edge case’. So in light of that, let’s dive into groups / exceptions where my argument carries less (or no) merit.

Extreme Poverty / Vulnerable Peoples

The biggest retort to my tweet, and one that I agree with (to some extent), is if you are coming from a family with very low income, and your first job needs to have a solid, stable income to help support them. Startups are probably not your best route; they don’t pay as well, the hours are / can be more volatile, and benefits (i.e. health insurance to spouse + family) may not be sufficient.

Likewise if your parents / family is in an incredible amount of debt, and you have a responsibility to help with this. Other situations of vulnerability may include: you / someone in your family is gravely ill, you are an immigrant and need a corporate job to sponsor your visa, etc. I don’t want to sound like the guy at the end of a drug infomercial, but if you think you’re in this boat, then feel free to ignore my argument.

Technical roles

I’m not a fit for engineering, data science, or other ‘technical roles, so those paths aren’t ones that I can speak to. I’ve heard arguments from both sides — startups move faster and give you more responsibility, which are universal arguments I’ll make in this post. On the other side, corporate jobs give you exposure to larger infrastructure and problems you wouldn’t see at a startup. There isn’t a true Product Manager at a 10-person startup — you’re probably 80% engineer and 20% putting out fires. However, at a company like Facebook, Google, IBM, etc. this is a great role. You’ll learn how to work with different teams and see what it takes to push out a new feature / product. So if you’re technical and want to pursue those types of careers, this post may have value to you or it may not be applicable.

Other passions / paths

I added this part as an afterthought, so I apologize for the brevity. If you want to become a doctor but have an interest in entrepreneurship, then startups probably aren’t a good fit for you. Likewise, if you love finance and want to start your own fund, startups would be a poor choice. If you want to make a stable 9-5 salary, start a family, and retire in 40 years, then startups also aren’t the greatest path.

This post is for anyone who hasn’t decided on their path yet and is choosing a corporate job because of the benefits that supposedly prepare you for entrepreneurship + maximize learning.

Why choose startups

Great, so with that out of the way, let’s dive into why startups are an amazing path for those interested in tech + entrepreneurship. The main three points I’ll argue for are (1) Hands-on experience, (2) Versatility and challenges, and (3) Learning potential.

(1) Hands-on experience

I’m a marketing / sales guy. That means my background is primarily in email marketing, content creation, marketing analytics, paid acquisition, and partnerships. When I joined Clearbit, they were 22 employees, and I was the 2nd hire on the Growth (marketing) team. There was a lot to get done, and they really couldn’t afford to silo work and set barriers because I was an intern.

So over the course of the year, I setup multiple email drip campaigns that went out to 10,000+ users, set up a dashboard to monitor the revenue and marketing/sales stats for the company, and was the main point of contact for partnerships with Zapier. This is the reality at a lot of startups — you get hands-on experience since there is an infinite amount of work to be done.

This isn’t the case at a corporation. A company like Uber has very specific roles for each function of marketing — building community (3-5 years exp), coordinating influencers (3 years exp), analyzing marketing data (5 years exp), paid acquisition (5+ years exp), and the list goes on. It’s challenging to get an entry-level role where you get hands-on experience in any of these roles; it’s more likely they’re curating you to be a manager for these types of people.

Tl;dr — it’s hard to get hands-on experience and autonomy at corporations. Instead, you get to shadow and assist people who do.

(2) Versatility and challenges

During my first college internship at Shopify Plus, the organization was 60-people and in a unique spot — they had the resources of a public company (Shopify) but the autonomy to prove out their own model, similar to a startup. This meant there was a lot of work to get done and little precedent on who should tackle it and how.

Over the course of the summer, I had a variety of responsibilities. At one point, we had a ‘concierge’ service where I’d take incoming calls from the Shopify Plus website — very representative of an intern role. On the other end, I had the freedom to send multiple sequences of outbound email to potential Plus customers, conduct a discovery call, and, if it got to that point (which it didn’t), negotiate the contract and close a deal.

In my 2nd summer at Shopify Plus, the organization had grown to ~ 300 people. I was on the revenue operations team, had great direction & mentorship, and learned a ton. However, there was the added bureaucracy and red tape of a bigger company. Certain projects were high-priority and out of my scope, others I had the freedom to tackle but had to jump through hoops to get approval for moving it forward.

Large corporations can’t afford to (and honestly don’t need to) take chances on new grads to get work done. Instead, they have training programs like these — two years of rotating between different departments so you can learn how the organization functions and how to navigate it. This is an incredibly powerful role, but keep in mind that they have this program for a specific purpose.

More specifically, there are things they’re expecting you to do, and things they aren’t. They know how to challenge you, and what you’re capable of doing. You’re most likely the 95th+ person to go through this program, so there shouldn’t be any surprises. I have friends in some of these roles where it’s frowned upon to work beyond a certain amount.

Startups don’t have this — in (most) of the roles I’ve taken, I was doing things I’ve never done before or didn’t know how to. I was challenged beyond my means (which helped me to learn faster), and my role was never silo’d into one thing or another. Early on in your career, I think that’s exactly what you need to grow.

Tl;dr — corporate roles are well-defined, in terms of responsibilities and challenges. Startup roles aren’t, and that helps you grow faster.

(3) Learning potential

I’ll never forget an interview I had with a sales manager at Shopify Plus in late 2016. I was ecstatic about sales, and made my entire ‘pitch’ about my passion for it, what I wanted to learn, and what I could do. His response made me think I didn’t get the job:

You can learn sales anywhere. The most you’ll take from this internship is seeing what happens when a company is growing this quickly. It’s a rare opportunity.

He was right — the sales team was ~ 10 people, and we were very much still figuring out what worked and what didn’t. Witnessing those conversations, how people sold a new product, and what experiments worked (or didn’t) was infinitely valuable.

That’s the benefit of a startup. Things move so quickly, that your role (and the company) 3 months ago is very different from what it is today. These learnings helped me understand what it took to build a business. What it meant to hire for sales, find new channels for leads, retain customers once you’ve signed them. Essential learnings, in my opinion, to being a good entrepreneur.

Corporations don’t give you this opportunity. The business has been around for decades (if not more), meaning that while it has changed, it does so slowly and not in ways a new grad can observe. I.e. the conversations on what direction Facebook is taking certain products will not be visible to someone who is in charge of shadowing the person that grows the use of Facebook Marketplace in Canada.

Tl;dr — corporations move slowly and are siloed, so learning how the business grows is stifled. Startups change quickly, so learning what it takes to go from $1M to $5M, or $5M to $10M is drastically different.

Conclusion

I’d assume (and hope) I ruffled some feathers with this post. So to clarify, I see a ton of merit to corporate jobs, and I don’t think anyone is making an objectively ‘bad’ decision by pursuing one. You get a good salary, clear opportunities for progression, and far more resources for mentorship. I have friends in these roles — whether it’s consulting, banking, product or product marketing — and I think those are phenomenal opportunities.

You learn how to be a manager, how to work with different stakeholders, and how to solve problems. These are universally applicable skills, but I don’t believe they are (as) useful as an entrepreneurship. You need to know how to sell to start a business. To generate leads and grow your presence as a marketer. To retain the first customers (and revenue) your business has ever seen. This all happens with limited resources and no direction. Working in startups prepares you for this a lot more than working at a corporation ever will.

I omitted a few points for startups that didn’t fit neatly into the categories above. Throughout your time, you’ll develop a huge network of people (marketers, salespeople, developers, etc.) that you may eventually want to start something with, or hire them. You’ll also meet mentors who have done it before and venture capitalists who can fund your idea. There is overlap here, as I’m sure you’ll meet this types of people while working at a corporation like Facebook or Google. Unlikely you’ll meet them at a CPG company or a big bank.

Lastly, I want to stress the absolute nonsense of prioritizing salary / prestige if you’re not in the ‘exception’ boats I mentioned above. I’m 22, what am I really going to do differently if I’m making $100k instead of $70k? Factoring in taxes and other factors, not much. I’d also be very hesitant to start a company with anyone who doesn’t have execution experience, regardless of whatever brand name they have on their resume. Management skills, in my opinion, are far less important when you don’t have product-market fit or consistent revenue.

The next Facebook

Imagine if the ‘rating girls’ app in  The Social Network  blew up INSTEAD of what we know now as Facebook? Actually, don’t imagine that…

Imagine if the ‘rating girls’ app in The Social Network blew up INSTEAD of what we know now as Facebook? Actually, don’t imagine that…

There’s no question that companies like Facebook, Apple, Amazon, Netflix, and Google (FAANG) have disrupted their respective industries, in many cases creating new ones that are worth billions of dollars. When I mention tech to the average person, these are the names that come to mind. Be the next ‘Zuckerberg’, 'Jobs’, etc. But what does it take to build the next Facebook?

In this post, I’ll go over my thoughts around the characteristics of massive tech companies, what it might take to build the next one, and emerging players that could be exactly that. A lot of this stems from a convo I had with a friend at Penn (thanks Will!), so giving credit before we jump into anything.

‘It’s a platform play’

Within the tech / VC community, this phrase is seen more as a meme or joke than a serious consideration. Any startup looking to raise capital will have at least thought of mentioning this in their pitch. To build a massive tech company, it’s not enough to have product-market fit and a profitable model — there’s a need to build something that has the ability to foster additional businesses.

A company like Salesforce isn’t just CRM software; they have an ecosystem that provides an environment for other integrations (i.e. email marketing, data enrichment, etc.) to thrive. Their market capitalization is $115B, but their ecosystem is valued at around $859B. The same goes for companies like Facebook, Apple, and Shopify (each with their own app stores).

I’ve mentioned in past posts that it’s an incredible success to build a business that has product-market fit and is profitable as a company. However, I don’t believe that alone is enough to be the next Facebook. In fact, there are businesses that make 8-figure revenue whose sole clientele are Salesforce customers. This goes the same for platforms like Shopify — agencies like BOLD and BVAccel generate tons of revenue for Shopify, and in turn, Shopify Plus customers make up a big portion of their revenue.

Industry & market size

I personally hate the mentality of ‘shoot for the moon’ when you’re building a business, especially for the first time. Sure, it’s more exciting to be tackling an industry or problem that is massive and ready for disruption, but this makes execution especially important — and for entrepreneurs with no track record or background, probability of failing (which is already very high) skyrockets.

There is a difference, however, between ‘moonshot’ businesses and ones that try to tackle a unique industry, with a lot of potential for expansion into a large target market. Amazon didn’t start as the de facto option for ordering online, it started as an online bookstore. If you looked at the company 1-2 years after starting, no one would have predicted the rise of Amazon Web Services — which has since risen to become one of the incumbents in the web hosting space.

An easy example to look at to better understand the difference is Square. They started with a Point of Sale (POS) reader that allowed merchants to take electronic payments. There was no dashboard, fulfillment integrations, or services for discounting and customer management. You’d be a fool to think they would ever venture into being a financial institution — offering loans, debit cards, or P2P money transfers. And that’s exactly what they did.

They didn’t do it from day one, with a slide deck and a 5-year plan. Square did it by starting with something they knew they could tackle (POS), and grew to involve other aspects of the business. Eventually, when a huge portion (if not all) of a business’ revenue was being processed by Square, they could predict future revenue and costs, allowing them to offer loans with a high probability of repayment. Square is now emerging as a financial institution, and is on its way to taking over the industry.

Tackling the right niche / problem, with potential to expand into a larger market, is another characteristic of businesses that will become the ‘next Facebook’. I have personal conviction behind the idea that finance will be the next industry where this happens — hence my bullish attitude towards Square, Shopify, and other companies that are tackling this (directly or indirectly).

Good timing

With an incredible team, product, and level of validation, a company can achieve success. Without the right timing, it will always fall short of its true potential. When I think of timing, the last two elements (industry and problem it solves) comes to mind. A great example comes in the form of Virtual Reality.

The possibilities of Virtual Reality are endless; it would reduce the need for many visual displays (i.e. TV, monitors, etc.) that we currently require for other devices (i.e. computers, gaming consoles) to function. The idea that you could have what is basically a brick-and-mortar experience from the comforts of your living room is mind-blowing. At some point, it could make remote working experiences the near equivalent to the physical office environment.

But not yet. Although it has some consumer appeal, Virtual Reality is more of a luxury than a practical piece of technology. Startups tackling this space may see some success, especially if they can find a niche and execute well, but really blowing up is challenging when consumers just aren’t ready. Facebook hit the timing well, when consumers were being used to having computers + the Internet in their everyday lives, but lacked an (effective) method to stay connected with each other.

In order for a company to become the ‘next Facebook’, timing will have to be near perfect. Anyone who comes too early will either fail or see limited success, while those who come late will see strong returns but fail to be the incumbent.

Conclusion

Technology companies have been changing our lives for 20+ years. It started with IBM and Xerox, then Apple and Google, and finally with Amazon and Facebook. Each one of these companies found a problem with a larger target market they could grow into, and had great timing. Others may have tried, but couldn’t get the formula right, and are eventually forgotten. Try it yourself — I can easily name ~ 5 companies that have recently failed; I’d be hard pressed to do the same for the 1980s.

The caveat in all of this, as I mention with many of my blog posts, is that I know nothing and am constantly learning. The elements I mentioned above could be essential to the ‘next Facebook’, or they could be entirely irrelevant. Send me a message if you disagree, and your thoughts on the ‘next Facebook’.

2019 — Checking in

Need to be on course for 2019! Avoid rocky waters! More sailing puns! (above: Mexico — 2018)

Need to be on course for 2019! Avoid rocky waters! More sailing puns! (above: Mexico — 2018)

I’ve mentioned in past posts that 2018 was easily the most eventful year of my life, thus far. There were a lot of ups — solid career experience, met amazing new mentors, and found a strong support system — and also lots of downs — injuries, loneliness, and heartbreak. Overall, it sets the bar pretty high for 2019, which makes it all the harder to plan for.

In this post, I want to dive into my plans for 2019, revisit my 2018 goals, and share my thought process. This is more of a personal exercise for me than anything, but I hope anyone reading takes something from it as well.

The past year

I’ll start by outlining a few of the goals that I had from 2018 and the progress I made on them. I think this will help set the stage for 2019, see what went wrong, and how I can improve.

(1) Reading

I’ve heard countless times that reading is the #1 thing that successful people do, and I back it. There’s the actual information you take in from a book, but more importantly there’s the reflection you do while reading. I.e. if you’re reading Steve Jobs’ biography, how do his experiences make you think about your approach to life, and the things you’ve done?

Unfortunately, I didn’t make a lot of progress on this goal. I read 3/10 books that I planned to, and am only just starting the 4th (River Out of Eden). My friend Kanwar gave some advice on this that I’ll share here:

“Life is too short to drag your feet through a book. Get the main ideas from it, and don’t be afraid to move onto a new one”

That’s paraphrased from my memory, which may have been impaired by a few beverages, but the idea sticks. I spent 3-4 months trying to read Meditations by Marcus Aurelius, and only got ~ 1/4 of the way through. I have a similar goal in 2019, to read a ton, but I won’t hold myself to a list of books or week-by-week goal. Instead, I’ll block off time to read every week (i.e. 30 minutes every 2 days), and not be afraid to start a new book if I’m not making progress. The following categories are especially interesting to me:

  • History — what happened between the 10th and 15th century? Before that? What can I learn from this? I believe that any book that survives the test of time has something to offer.

  • Philosophy — I fundamentally believe that any successful person operates from a sound value system. Similar to Principles, they know why they make the decisions they do, and don’t have weak beliefs. I believe different approaches to philosophy (i.e. stoicism) can help me get there.

  • Autobiographies — Successful people did something right, there’s no question there. So learning from how they think and specifically what they wish they hadn’t done can help me achieve my definition of success.

  • Business / Self-Help — I’m not sure what category 4-Hour Week Work or Principles falls into, but they were both great reads and I hope to continue to find books similar to them. Also nice to switch things up, since they’re typically a lot lighter reading than history / philosophy.

  • Fiction — I should force myself to read more fiction, since the only book (in recent memory) that I’ve read is When Breath Becomes Air, and it was phenomenal (though not entirely fiction). I hope to enjoy reading a lot more by switching it up with fiction books.

(2) Personal health

I tried becoming an early riser this past year with little success. I found the biggest issue was having a reason to get up — if I didn’t have class, someone to meet, or another commitment, there wasn’t much incentive to get out of bed. A part of this was probably my poor quality of sleep, which is a consequence of sleeping late, drinking coffee / other stimulants (i.e. alcohol), and not having a good routine.

I’ve heard before that everyone has their own biological clock and some people function better as night owls. I don’t believe this is true (for me), but I think a smooth transition is in order. So I’ve decided on the following goals:

  • Wake up at 8:30am (latest) everyday — I’d assume with work / school I might have to get up earlier, but I think committing to this regiment will help maintain a somewhat predictable sleep schedule

  • Meditate for 15 minutes per day — I’m a huge fan of Headspace, and used it frequently from July through October. While I will strive for 15 minutes in the morning and before bed, I think setting the bar of once / day is a good start.

In terms of my other personal health goals (food + fitness), I felt like I made some solid progress. Although I ate out a lot while working in SF, from Sept — Dec I had home-cooked meals usually 5/7 days of the week. I also made progress on my weight training goals, and have considerably better cardio thanks to intramural soccer and squash (Victor & Chris, I’ll beat you one day!).

(3) Mentors & skill development

This is by the far the goal I am most proud of making progress on in the past year. While in SF, I met a number of early-stage founders who have been incredibly supportive and helpful in my entrepreneurship journey. — people at companies like Slab, Kettle and Fire, Mattermost, and Zypsy. The biggest thing I learned was that no one really knows what they’re doing. Sure, some founders are better equipped than others, but everyone faces challenges that they’ve never seen before, and they’re not afraid to ask for help.

I’ve received some questions recently around how I approach reaching out to people, coffee chats, etc. Personally, I don’t feel the urge to reach out to new people anymore. I’m always open to meetings, but I think the generic “tell me about your life / career” didn’t yield many positive encounters in 2018. Hence, I want to use 2019 to only reach out to new people if I have a specific ask / value-add, OR if someone introduces us and thinks there is something there.

Instead, I’m going to direct this energy towards improving relationships with people I already know. I’m not ashamed to say that I have a Google Sheet with ~ 150 people, which tracks their name, position / company, the time we last chatted, and any relevant notes (i.e. had a child, left their job, taking karate). I want to further refine (reduce) this list in 2019 and be very intentional in how I improve those relationships.

For example, I’ll make a note 1-2 times a month to reach out to a set of mentors and see how they’re doing + share my progress. I’ve already scheduled recurring calendar events every ~ 2 weeks for close friends that I want to keep in better touch with. I recognize this is weird / unconventional, but I urge anyone who likes to be organized to give it a shot!

New goals

My goals this past year were great, and I’ll still going to pursue some of them, with varying levels of vigour. However, looking to 2019 I have two main goals that I want to be public about so I can be kept accountable. Here they are below:

(1) Social independence

This may sound like a(n intentionally) confusing term, but allow me to explain. I’m a natural extrovert, and I thrive off being around people. However, there are some people I enjoy being around more than others. To make up for the deficit, I’ll often have to use some sort of crutch — typically via going out / drinking alcohol. This is a convoluted (and unnecessarily more serious) way of saying “drinking + dancing at a function where you don’t know anyone so it’s less awkward”.

I’m a strong supporter of, especially career-wise, committing to things and doing them regardless of social norms. There’s no reason this shouldn’t extend to my social interactions. So, the first soft goal here is to stop being a ‘yes man’. I know it’s my last semester and I’m supposed to ‘send it’, but I think I’ll enjoy it considerably more if I say ‘no’ to more things and spend that same time with people I truly enjoy being around, ideally doing more wholesome things. Think karaoke, board games, or sports instead of hitting the bars.

The stronger goal here involves the ‘social crutch’ that I mentioned earlier. For 2019, I’m planning the hard goal of not drinking once I’m back in school. I’m incredibly impressed with friends who do this and don’t abstain from social environments (i.e. bars / clubs), so I don’t plan on cutting those out entirely. However, I think that cutting back on alcohol intake will help me understand myself better, and allow me to turn my ‘social self on/off without the need of a drink’, as a good friend once said.

(2) Starting a business

I’ve been committed to tech for the past few years, but only this past year did I realize that building something (entrepreneurship) was what most excited me. I’ve been grateful for a few opportunities this past year that have primed me for that path, such as getting into the Next 36 and joining Dorm Room Fund as a marketing partner.

The fact is, I’ve never started a business that has been revenue-generating. In fact, from failed attempts I don’t even think I’ve had a single user. Regardless of how much I might think I know about tech and startups, this is a hurdle I really want to climb to see what it’s really like to be an entrepreneur, from day one.

Hence, the soft goal for the 2019 is to start a business that is revenue-generating. Not contracting, or a strictly-services business (i.e. moving lawn), although that is already more than I’ve done. Since early October, I’ve done user research + launched a pilot for a venture that is coming to a close. I want to focus the majority of my energy on scaling it in the New Year and making it a profitable business.

The hard goal? Truth be told, and in an ideal world, I would not be working in an execution role after graduation. That includes sales, marketing, customer success, etc. for a company as small as 10-people to as large as Shopify (3k+ employees, public company). I’ve done it with Clearbit, and it was an incredible experience that I am forever thankful for. But entrepreneurship, as of now and going into 2019, is the goal. So my hard goal is to graduate and be running my own business full-time.

Conclusion

For any other students / new grads out there, you’ll relate when I say that every year seems drastically different from the last. It felt like yesterday I was in high school, let alone starting university and now into what is essentially my last semester. Everything from my interests, friend groups, and even my hair has changed over the last few years. It can be overwhelming and hard to keep up.

I find solace knowing that my goals will always change. That’s understandable, I’m human. What needs to stay the same is my ability to constantly question my goals, set milestones to achieving them, and be intentional with what I’m learning and why I’m doing what I’m doing. As long as that’s my mindset, I can’t to see what 2019 brings.

Contract work

My first contract role with the Turnstyle Solutions crew (now  Yelp WiFi )

My first contract role with the Turnstyle Solutions crew (now Yelp WiFi)

College can be a stressful time for a number of reasons. For starters, the endless flow of information is a plus, but the similar flow of assignments is a drawback. Beyond the classroom, there’s the responsibility of extra-curricular activities, sustaining a social life, and finding a job.

Jobs can be tricky, and in college, usually fall into the realm of ‘I don’t like it, but hey, it makes money’. Read: cashiers, waiters, etc. Don’t get me wrong, I have a lot of respect for those jobs and for the people who take them. However, I think there’s another category for jobs, which goes more like ‘I like the work and it makes me money’.

Contract work is a great way for students to dive into what they’re interested in, learn new skills, and most importantly, make some extra cash. In this post, I’ll walk through my experience with contract work, and tips I’d have for getting into it.

Marketing… Yeah that sounds cool!

Wrapping up my first internship, I realized that as cool as sales was, I was more excited by marketing. The only issue was that I knew nothing about it. This introduces the paradox of job hunting — they’re looking for people with experience, I don’t have any experience, but I need experience to get a job.

The first step I took to become prepared for a marketing role was to start reading up on it. Like with other skills (programming, design, etc), a lot of the content is available online (usually for free) that can help you break into that career path. Although I’d recommend anyone interested in marketing start here, I personally read a ton of posts on HubSpot and listened to Neil Patel (SEO) podcasts.

The plot twist? A lot of that information (and to be frank, some of my earlier posts on this blog) wasn’t very effective. It wouldn’t help me kill it in a marketing role, or even have a thorough understanding of that skill, whether it be email marketing, SEO, etc. What it did give me was a foundation — a basic understanding of that field, and a list of questions I could ask that would show that I was (a) genuinely interested in it and (b) eager to learn.

As I mentioned, this parallels a lot of different paths. If I was really interested in learning how to code, FreeCodeCamp and Codeacademy are both incredible resources. Odds are I won’t become a good developer through either, but it’ll give me a head start on knowing what to learn. The same goes for other jobs that build off a skill set, like Design.

Hit me with your best shot!

With a basic skill marketing skill set, I set out to find my first job. As many new grads will notice, there aren’t many roles out there that require “0 years experience and a smile”, even if you have a genuine interest in the job. The difference-maker is proving to the hiring manager that, despite your lack of experience, you’ll pick things up quickly. This is perfect for most ‘junior’ roles where the work doesn’t really require you have done it before.

My first contract gig in marketing came through Turnstyle Solutions (now Yelp WiFi). It was a fluke really — I was at a hackathon in Toronto (didn’t know how to code), and I reached out on their website for a demo account so I could help my team use their product in our hack. The ‘demo request’ went to someone on their Customer Success team, who was actually a Western University grad.

Where to go from there? Well, I had to be a little ambitious and flaunt my (limited) marketing knowledge. I mentioned in the reply to him that I had some background in email marketing and user acquisition, and I’d love to chat with someone on their team to show what value I could bring.

Note: The “I have background in X and want to chat with someone to see how if I can add value” is a fool-proof approach. Even if you definitely can’t, they’ll be willing to take a call with you in most cases.

I ended up getting an intro to their VP Marketing (now a great mentor of mine), and took a call to learn about their marketing efforts. Looking back, he could probably guess I had no clue what I was doing, but he could see that I wanted to learn. So he took me on as a contractor, where I’d get paid $20/hr for a few hours a week to help with their marketing.

Note: Experience is rarely a requirement if you’re looking for roles as a student. They know you have no full-time experience, and are typically open to helping you out if you’re driven.

Not your typical retail job

At this point, it’s worth noting that I wasn’t making an incredible amount of cash. I was, however, getting tangible experience in something I was interested in, AND I could do it from the comfort of my room (on my own schedule), since the work was remote and based on what I delivered (outcomes). That’s another beauty of contract work; in many cases, you’re not tied to a schedule, so if you want to wake up at 2pm and work until 10pm, as long as the work is done for the next morning, you’re golden.

Throughout this time, I also want to stress that I was still learning. There were a lot of tasks I got that I didn’t know how to do, so I spent a lot of time digging on the web and reaching out to people I thought might be able to help. The latter is amazing for finding mentors in your space, or even new jobs. Look at the two questions below:

“Hey I’m interested in marketing and want to learn more about it, can we chat?”

“Hey I’m doing email marketing for XYZ Company, can I see how your company tackles it?”

This works especially well for marketers, but imagine the same question for a designer or developer? I.e. “I’m putting together a branding guideline for XYZ Company, would love to see how you did yours” or “I’m developing a mobile app for XYZ Company, curious how you guys tackled it”.

With a bit of experience and a growing skill set, I stumbled upon my next contract job a few months later, and have kept up with part-time gigs since. Contract work initially helped me splurge on a meal out once a week, but after gaining experience and a portfolio, now helps me pay for trips and school fees.

Where do I start?

If you’re interested in doing contract work for a specific skill, try the same approach of (1) learning about the role (2) reaching out to people to see how they do it (3) offering your services. Even if you don’t have a specific skill, you can try sites like Upwork to get some solid paid work — whether it’s testing an app or conducting Google searches. For obvious reasons I’d recommend the former approach of targeting a skill, but whatever floats your boat.

A couple of things I’ve learned over my time doing contract work:

Communicate frequently. In most roles, you’ll be taken on as a remote employee, which means you won’t be in the office and your work is project-based. The former means you’ll miss a lot of context on projects that happen in casual conversation, and the latter means that you can’t ask questions or give updates on-the-fly. It helps to set check-ins with your manager at a certain time every week, and don’t be afraid to ask questions if you’re unclear on a task.

Give specific value. In the initial outreach, and throughout the contract, it may be tempting to ask for ‘general’ work related to your skill set. I.e. “Can I help with marketing”. For a lot of companies, being a generalist is fine if you’re a full-time employee, but they hire contract workers for specific purposes. So even in the initial outreach, saying “Can I help with your email marketing strategy” or “Can I help with the design of your homepage” is a lot better than “Can I help with marketing or design”.

Learn constantly. As a student, contract work is (should) not be seen solely as a source of income. It’s an opportunity to sharpen your skills in a specific field, work your way up to bigger (and higher paying) roles, and eventually launch your full-time career in that area. If you’re doing work that is repetitive, that might be a red flag where you should ask for new tasks, or better yet, think of new skills you want to learn and tasks at the company that involve that. For some of my earlier roles, that meant doing solid work in their CRM (more repetitive) and asking to help improve their SEO strategy (new waters). That helped me broaden my skill set to include SEO, and have tangible projects to practice on.

Conclusion

Clearly there are professions that don’t allow for contract work; if you want to go to med school, any ‘contract doctor’ role is probably sketchy and might get you arrested. But for work in tech (and a number of other fields), contract work is a great way to make money, gain new skills, and prepare yourself for full-time work, all while being in school and in the comfort of your home!

Finding your dream job

Action shot of the Clearbit sales team and I at Base CRM’s annual conference.

Action shot of the Clearbit sales team and I at Base CRM’s annual conference.

Needless to say, the college environment and the work environment are drastically different. They both have their pros and cons — for the former, I have a lot of free time, a predictable schedule, and I’m surrounded by people at a similar stage of life as me. The latter has its perks too — the work is more engaging, I have a consistent source of income, and there are a ton of people to learn from.

Chatting with friends who are also wrapping up their final year, the conversation varies. Most people fall into one of the following buckets:

  • Signed a full-time offer / committed to grad school, enjoying the year

  • Know what they want to do, but still looking for full-time work / applying to schools

  • Not sure what they want to do, aren’t sure where to start

I’ve written a fair amount about finding internships and succeeding in the workplace, but the tl;dr is that it all comes down to finding what you’re both interested in and good at (usually correlated). In this post, I want to dive into how I found my passion for technology and marketing, what questions I needed to answer along the way, and what role I think is the best for new grads.

Dazed and confused

First year was a bit of a mess. Trying to adjust to school work and a new social environment is hard enough, without everyone stressing about finding jobs and being the best at whatever you’re interested in. My older brother had just graduated from Western, and the friends he introduced me to, who had done the business program (Ivey), were committed to paths in finance. You get to wear a suit, make lots of money, and work in ‘capital markets’, so that had to be pretty sick, right?

The first piece of advice I received and still stick to today, is that you need to dive deep into whatever you’re interested in. It’s not enough for me to say “yeah I think finance is cool”, without having ever spoken to anyone working in the industry, learned any of the material, or discovered whether I’m good at it. The sad reality is that a lot of people never make it past the ‘interest’ stage; I could have gone through all 4 years of college being ‘interested’ in a variety of roles, but when it comes to getting a job, I would have been unqualified for them, and more importantly, would be unsure which path I wanted to commit to.

So following this logic, I started to dive into finance. I read Mergers & Inquisitions to learn about the work and lifestyle, talked to older friends who had worked in finance, and started the (in)famous Breaking Into Wall Street prep course for future financiers. After months of digging and figuring out…

Well actually, scratch that. It didn’t take long at all. In about 3 weeks, I realized some key points:

  • Finance was cool, but I wasn’t really interested in how the markets worked

  • The work (at an early stage of your career) was dry and repetitive

  • The lifestyle involved gruelling hours and being constantly on-the-clock

Keep in mind, this is my personal view of finance careers. I have a ton of friends going down that path, many of whom are genuinely interested in finance, and I commend them for it. It’s an amazing career for many people. Just not for me.

Tech? But I can’t code…

Back to square one, I had to do some deep thinking to figure out what I was really interested in. A lot of my friends told me about management consulting; a job where you get to solve problems, work in different industries, and travel! It sounded glamorous, and a pretty great fit for me. Most importantly, it would ‘help me figure out what I wanted to do’.

There were two small issues with this: first, if I was in first year, I had at least 3-4 years to figure out what I wanted to do, by trying different roles and diving into my interests. It didn’t make sense to commit (that early) to a job path that would eventually help me answer those questions. Second, they typically only hired 3rd year business students for summer internships, so I had to do something in the meantime, right?

Hitting the career fair at Western, I met a recruiter from a large telecommunications company. I was bright-eyed and eager to learn, so I asked them about their internship program. Their response:

“Love your enthusiasm, but we only hire 3rd Year students in the Ivey HBA program”

Great, well that wasn’t helpful. I had plans for Ivey but still had a ways to go. After talking to a variety of firms at the fair, I didn’t have too many leads to run with. Returning back to residence, I realized I signed up for London Tech Fest — a night of free food and informational booths from tech companies. I couldn’t find anyone to go with, so I hopped on the bus solo to get to the venue.

At the fair, there was a green booth with a familiar name: Shopify Plus. I had heard about Shopify before, and though it was a pretty cool place to work. Unfortunately, I wasn’t in engineering (or even business), and didn’t think I had much of a shot. So I walked up to the recruiter, and tried to think of a way to impress him. The conversation went something like this:

Me: “Hey I’d love to work for Shopify, but I’m only in first year and I’m not in business”

Him: “Why would that be an issue?”

Me: “Well I went to a career fair today, and (telecommunications company) said they would only hire 3rd year business students”

Him: “Screw (telecommunications company), we do things differently here”

In a matter of minutes, I was already a big fan of Shopify — they didn’t abide by the status quo. During our short chat, I kept telling him how I wanted a role where I could hustle hard and do work that mattered. He gave me his card, and said to reach out about a sales internship.

Naturally, I was still a little shocked that my limited education wasn’t a barrier. So I asked if I should learn how to code. He told me that ‘tech’ companies don’t just hire engineers — they need salespeople, marketers, customer success experts, and a ton of other non-technical roles to grow and succeed. These people should know about the product, but they don’t need to know how to code. So I ran with it.

Sales: the ultimate launchpad

Fast forward a few weeks of interviewing, I got the offer to join the Shopify Plus team for Summer 2016 as a sales intern. Keep in mind, during this process I was never asked for my transcripts or GPA. I learned later on that those things are a filter for ability, but don’t predict how you will perform in the workplace. Most small to mid-sized tech companies don’t care about your major or grades, they just want to know if you can do the job well.

The interview process was challenging, in that I didn’t really know what to expect. I read up a ton about Shopify as a company and their various products, along with reading up on sales and what it entailed. I reached out to people working there to see what they had to say about a career in sales — here are some of the key points:

You’re a consultant, not a salesperson.

Wow, that got me excited. I was planning on doing consulting anyways, so imagine what this could do for me! In all seriousness, every rep I talked to stressed how important it was to understand the needs of the person you’re selling to (a lead), what their hesitations are, and how your solution might be a fit for them. Shoving products down someone’s throat doesn’t get you anywhere — in fact, it actually costs the company more if they leave (churn) soon after becoming a customer. The best salespeople help leads figure out what they want, and the leads sell themselves.

It takes perseverance, hustle, and creativity.

Sales is not a cushy job. You don’t have vague deliverables or layers of promotions before you actually get to do the job. From day 1, you’re learning to sell and getting direct contact with leads, soon after getting a quota that you need to hit. If you don’t hit the quota, you’ll be placed on an improvement plan and eventually fired. It’s the only job where there is no cap on the amount of effort you can put in — the more you sell, the more money you make and the better for the company. It’ll teach you how to hustle, get creative with your outreach, and hit your goals (your quota).

You’ll become an expert at controlling conversation.

My initial reaction to sales, like many people, was that it’s a sleazy profession that doesn’t involve many ‘hard’ skills — you basically just need to be good at persuading people. The reality is that it’s not that simple, especially when you have to convince the 50 year-old executive of a multi-million dollar enterprise that your product is worth their time of day. Most of my sales colleagues at Shopify Plus were under the age of 25, many of them fresh new grads. They sold to Drake, Tesla, Big Baller Brand, and Kylie Jenner. I can’t think of anywhere else where you’re the main point of contact to such incredible companies, let alone where you’re solely responsible for bringing them on as a customer. Knowing how to drive conservation, set deliverables, and get someone from “I don’t care” to “Take my money” is a magical process — and it’s called sales.

You’re working up from ground zero.

The best part about careers in sales is that there is really no ‘ideal path’ into it. Some of the best salespeople were psychology majors and never sold a day in their life. All entry-level sales positions, whether it’s at Google or a 10-person startup, will teach you how to sell and eventually turn you into a confident salesperson. There is NO pre-requisite, except an ability to think quickly and a willingness to learn fast and hustle hard.

The world is your oyster.

After learning how to sell, you can stay in sales and move up the chain to be a killer account executive, or move to management and run a full sales team. You can also make other transitions — people I know who started in sales have gone on to become successful entrepreneurs, marketers, product managers, and much more. Sales is the ultimate toolkit / skillset that will enable you to succeed in a number of career paths.

Okay — Where do I start?

There are hundreds of tech companies that are hiring new grads as salespeople. All it takes is preparation to learn the sales basics and an open ear from the hiring manager. I saw this gap over my time in tech, both in Toronto and in San Francisco.

That’s why I’m starting a program to get more new grads into tech sales. It involves a 3-week bootcamp on learning how to sell, written by current sales professionals, and then we refer you to a variety of companies — everything from 10-person startups to UberEats — to interview and get a sales job.

If you’re graduating in April 2019 and are still looking for full-time work / aren’t sure where to start, or know someone who is, shoot me a message so I can get you involved in the next cohort.

Regret

I can’t regret a burger right? Especially In-N-Out?!

I can’t regret a burger right? Especially In-N-Out?!

I wrapped up my last post mentioning how I’ve made a lot of bad decisions. The typical feeling associated with these decisions is regret. The question I’ve been thinking a lot about lately is how to discern between the different types of regret I can feel, and what is the best way to handle it.

Revisiting a decision

A key part about decision-making is that I have a certain amount of information available to me at the time of the decision. For example, I could bet on a specific stock if I’m impressed with what the vision and current progress of the respective company is.

After making this decision, a number of things could happen:

  • The stock skyrockets, in line with my assumptions

  • The stock skyrockets, in ways I could not have foreseen

  • The stock plummets, contrary to my hypothesis

  • The stock plummets, in ways I could not have foreseen

Whether the stock goes up or down, if it was unpredictable given the knowledge I had at the time, then I (should) feel confident that I made the right decision. In contrast, if the stock performs outside of my expectations, whether up or down, I can start to question whether the decision was a right one.

Revisiting that decision involves a frank discussion with myself about what I should / shouldn’t have known at the time of making the decision. As I mentioned in this post, if I put a good amount of thought and effort into picking a stock, that in itself should make me comfortable regardless of the outcome.

The challenge here is forcing myself to revisit decisions I make, regardless of the outcome. If the stock went up in ways I didn’t predict, the outcome is in line with what I want, so I won’t question whether the decision was a good one. Though realistically, that lack of questioning might lead me to make an even riskier decision down the road, using the same (probably flawed) line of thinking, that ends up hurting me a lot more.

Forceful re-evaluation

With those scenarios in mind, it’s clear that decisions can be bad ones if they are not revisited. However what makes me want to revisit a decision in the first place? Regret.

Regret is an emotion that is often sparked by the outcome of the decision, but can be associated with the decision itself and/or the outcome. I wouldn’t regret going to the gym unless I hurt myself, nor would I regret playing video games unless I had something pressing to do.

So I can accept that there will be decisions that I make in error; specifically where I don’t consider all the possible factors and end up choosing the wrong option. That’s life, and I’ll learn from those decisions.

What frustrates me the most, is feeling regret from decisions that I am / was very confident in making. Ones that I put an incredible amount of thought into, got insight from people I trusted, and gave it time to ensure I wasn’t making any impulse decisions.

This is what I would call ‘regret from outcome’. Leaving San Francisco is a primary example of this for me. I miss the work, the people, and (sometimes) the city, and that can make me wonder whether it was a regrettable decision. However, I’m still confident in the logic behind the decision and the process I went through to get there.

Handling regret

So what exactly should I do with ‘regret from outcome’? It’s purely emotional, and I can’t exactly logic myself out of it (trust me, I’ve tried). I’ve had it plague me in influential areas like my career and relationships, as well as everyday areas like eating and sleeping. This past weekend, I regretted the feeling of not eating a 2nd Big Mac, but it was the right decision (right? Right?!!).

There are a few strategies I’ve found that are especially influential here. The first is to really dive deep into why I’m feeling regret, what it stems from, and eliminate (if possible) any notion that the decision was the wrong one. This includes both journalling and talking to people I trust about a decision and all the feelings that accompany it.

The second is to think of the opposite emotion, and when I’ll be able to experience it again. For the Big Mac, there will be a day in the coming weeks (or less) where I exercise a significant amount and feel good about eating it. For careers, there will be another role that I’ll feel as passionately about, especially if it’s my own project.

The last strategy on my list to dealing with regret is to, well, feel it. Some days it’ll drain me to the point of not being able to function, constantly thinking about those emotions. There’s no point fighting this, or suppressing it via other mediums. In fact, distracting myself only makes it worst, as it just delays the (eventual) feeling that I’ll have. So the solution is to feel regret of outcome; watch TV, listen to sad Drake, eat some Cheetos and go to bed.

Conclusion

I read a significant amount about ‘hacking’ life — daily habits, stoicism, frameworks to implement, etc. At the end of the day, I’m still human, and there’s something reassuring in that. I’ll feel regret, just as everyone else does.

The key is to discern between ‘regret of decision’ and ‘regret of outcome’, have a concept of the future, while still being present when those emotions hit me. Is it harder than it sounds? Of course! But knowing it’s the logical way to deal with things is enough for me.

Principles & decision-making

Not exactly a ‘fork in the road’, but hopefully the fact that it’s original counts!

Not exactly a ‘fork in the road’, but hopefully the fact that it’s original counts!

Being back in a school environment has been phenomenal — it’s a space for learning, making strong relationships, and figuring life out. In catching up with friends, the conversation quickly shifts to jobs, career planning, and what seem like existential decisions.

I faced similar challenges when deciding to take a year off and work at Clearbit. I had concerns around being behind and missing my friends / family, both of which were valid at the time. Even currently, I struggle with decision-making (both career-related and not), but found strategies and frameworks to make it easier, which I’ll break down in this post.

Personal goals

In his book Principles, Ray Dalio explains how the decisions he made at his hedge fund (Bridgewater) were largely based on a series of statements that the company agreed to be aligned upon (principles). Everything from investment strategies to hiring policies needed to match the principles, and anything that didn’t match should be scrutinized.

For individuals, I see principles being tightly coupled with personal goals. They can involve career aspirations, but for me they include non-career pieces too. Here’s a rough idea of my principles:

1. Be constantly learning

This one is straightforward, but easy to overlook. Every job I’ve taken since coming to college has involved something that I didn’t know, and wanted to learn. In my earlier days with sales internships, it was strictly learning how to sell. Later, it evolved into understanding the full funnel (paid ads, email marketing, etc) and being data-driven (SQL, reporting).

This principle isn’t unique to jobs — while I’m guilty of taking some ‘bird’ courses or module (required) ones, a lot of my classes are ones that I have an intrinsic interest in. Outside of class, a huge component of this is reading. I love discussing my thoughts with friends and being willing to shift my viewpoint. It’s more of a mindset than anything, where I try to come into a conversation with the intention of truly understanding what someone is saying, and challenging them if I don’t agree.

2. Build a strong support system

This is more recently embraced principle, that I adopted mainly after returning from my year in SF. While college gave me a false impression that things were always looking up (internships, grades, etc), I soon realized that life is a combination of good and bad times. It can almost be seen like a portfolio; my work could be going well, while my relationships suffer. Or maybe they’re both in good places, but my physical / mental health is poor.

I believe the ultimate defence against these fluctuations is a strong support system. Friends, mentors, family that I can depend on when certain parts of life are getting me down. While they are all awesome, I rely on different people at different times. My mentors and friends that have similar mindsets career-wise are incredibly helpful when I’m lost in that regard, both for giving advice and being a soundboard for my thoughts. The same goes for school planning, physical / mental health, and handling relationships.

3. Surround myself with people smarter than me

Being wrong or making a mistake is one of the best things that can happen to me — it forces me to re-evaluate, understand what happened, and learn from it. This is especially powerful when I’m with people who are smarter than me, in a work environment but also in life. The former helps me understand how others react to failed projects, slow days, meeting expectations, and being overwhelmed. It’s incredibly helpful to get feedback on poor work when I have an immense amount of respect and admiration for the person I’m working for / with.

The latter is crucial to goal #1 (learning), but is more of an indirect catalyst. I have great friends that don’t challenge me, and sometimes that’s a good thing. But I also have others who will scrutinize my decisions (even when I don’t ask), which is a very powerful quality. Surrounding myself with these people keeps me on my toes, ensuring I have some level of reasoning behind what I’m doing.

4. Be financially independent

I’ll keep this one short, but it ties well into my goal of building something. I’ve heard great arguments around why a 9-5 job is like slavery, where you’re tied to the income given to you and the schedule set for you. I strive to go beyond this, by finding roles where I’m either financially independent or working towards it (i.e. learning skillsets to get there).

A much smaller component around this is budgeting and being fiscally responsible. This ties to decisions that maybe aren’t career-related, and are more dependent on my stage of life and my aspirations. I.e. getting a car (and what kind), taking trips, going out, etc.

5. Discover and refine my value system

The college environment is a double-edged sword when it comes to this one; on one hand, it gives me tons of free time to discover and refine my interests, but on another hand, it often gives me a viewpoint (i.e. through classes / professors) that I don’t need to challenge.

I find this to be one of the advantages of a liberal arts degree, as the classes I’m taking (philosophy, political science) dive into a more epistemological approach to course content. I.e. it’s not just memorization and regurgitation, but rather understanding what different perspectives yield, why they think that way, and developing a critical opinion on what I believe. Beyond the classroom, there are various areas I want to gain a deeper understanding of, like religion / faith and philanthropy.

Application to life

These goals / principles shape a large part of my decision-making, whether at a small or large scale. For the former, it’s everything from cooking more in the week (goal #4) to taking classes that are more challenging / interesting (goals #1 and #5). For the latter, it meant deferring a full year of school so I could learn a ton, be around smart people, and build a skillset (how companies work) to get me closer to financial independence.

Opportunity cost

With an understanding of principles / personal goals, I find existential crises with choosing job paths & internships confusing. Calculating opportunity cost at face value is simple — the difference in salary, prestige, alignment with interests, etc. However, when I factor in my principles, my analysis reaches a new level.

For an imaginary example, choosing a full-time marketing role at Uber in San Francisco over being the first business hire at a promising startup in Toronto might seem like a no-brainer. For the former, the salary is higher, it’s more prestigious, etc. When factoring in my principles, the following thoughts might arise:

  • The majority of my support system (including family) is based in the Toronto area; keeping in contact will be challenging — Goal #2

  • I want to be learning as much as possible; a large company like Uber will provide a safe environment where I can’t (as easily) make mistakes, but it also means I won’t be able to learn from those mistakes, or try areas outside my role — Goal #1

  • Uber is a company that is already thousands of employees; while the salary is higher, it can be argued that learning how to build a company (Toronto) will lead to eventual financial independence faster than simply executing in a role — Goal #4

  • There are a ton of smart people in the Bay Area, and that environment will challenge me more than Toronto would — Goal #3, Goal #5

Is there a clear-cut answer here? Not with the information given, but it did make me think a lot more critically about why I’m choosing one role over the other, which I think is the real value to depending on a set of principles.

Conclusion

I’ve made plenty of bad decisions, and while I try my best to learn from them, it doesn’t change the fact that I made them. Sometimes the “what ifs” can be overwhelming — and if it was a poorly reasoned decision, it makes it all the worse. However, in a lot of cases, using this type of logic helps me either justify good decisions, or question bad ones. Principles, for me, are constantly evolving, and that’s a sign of growth and self-reflection more than anything.

All in all, I’m still 21 and most decisions won’t have much weight in the grand scheme of things. Career choices are far from being set in stone — even a commitment to tech can shift to finance after an MBA, or to being a developer after a bootcamp. Life decisions follow a similar mentality — friend groups will change, value systems will shift, but as long as I’m staying in the present and being accepting + forward-looking for life, the world is my oyster.

A year of life

Company trip to Mexico — a great highlight of the year, and a solid cover photo! 

Company trip to Mexico — a great highlight of the year, and a solid cover photo! 

A large part of me really wanted to name this post "A year in the valley", but I don't think it would do it justice. This year has in many ways been the best and worst of my life, and little of that is connected directly to the idea of being in The Valley, or at least what I imagined it would be like when I wrote this post. 

This will be a lengthy one, and is you're mainly curious about the outcomes, then skip to "An Inflection Point". Otherwise come along for the ride, it's a bumpy one! 

A quick timeline 

I moved to San Francisco in September 2017, right after completing a 4-month internship at Shopify Plus. I was 20 years old doing Growth at a Silicon Valley startup, making an amazing salary and having absolute freedom in what I could do. There was no one here to judge my decisions, there was no precedence on what I should be doing or how I should approach the year. The world was my oyster. 

I also didn't have a strong support system. My family and all my friends were thousands of miles away in a different country, 3 hours ahead. I'd get home from work and realize everyone was already asleep. I'd see the college fun I was missing out on via Instagram (which I no longer use), and the events I couldn't make. While everyone was figuring out life, I had exactly what I wanted (and supposedly, had it figured out), but I wasn't happy. 

The first 3-4 months in San Francisco were rough. I tried hard to make friends here, and find something that gave me value beyond the workplace. I hopped on all the dating apps — Tinder Plus, Bumble, Coffee Meets Bagel (you'd be surprised how many there are) — with hopes of finding someone that would make San Francisco feel a little more like home. I also developed a lot of poor habits and an unsustainable lifestyle, trying to drown myself in work and partying excessively when given the opportunity. 

Things I used to love — gaming, working out, even tech — started to lose value. I wasn't performing to the level I wanted to at work, and not being 21 meant it was hard to participate in the events and social activities that my older friends enjoyed. To sum things up, it's a gut-wrenching feeling to have everything you always wanted and not be happy. 

An inflection point

Eventually, thanks to some very generous introductions and a few chance encounters, I started to get used to San Francisco. Around the start of the new year, I felt like I had a better understanding of my position at work, found a solid friend group of people my age, a girlfriend, and started to warm up to the city. 

It was around this time that I started to give more thought to long-term goals; realizing that at 21, it's highly unlikely that I was (A) at the top of my game and (B) in a role that's perfect for me. So I started to focus a lot more on the goal I knew (starting a company) and the goals I didn't know (what else do I want out of life). 

For the former, that meant reaching out to early-stage founders and others who had scaled successfully, to understand the validation process and what exactly went into building a good business. There are a few things I learned from these individuals, which definitely don't apply to anyone, but are points I'm sticking to in the coming months to building a product:

(1) Validation

If I have a hunch that X product will solve Y problem, I should be validating it. Emailing / calling people you think have that problem, talking to them about their business and how it operates, and learn whether this is something that will actually make a difference in their lives. There is a caveat to this, in that I should validate until I am confident & comfortable committing to this project. For me, that could mean having a large enough sample size of interested users, commitment to pay (or already paying), and a good understanding of what the MVP will look like.  

(2) Scaling 

I should be able to do the majority of the work at a very early stage. I shouldn't be hiring marketers, engineers, designers, or even finding a co-founder until I'm past the validation stage. A similar story for raising capital — yes it's sexy, and lets me have a salary + office, but those factors aren't necessary to success. I don't need a TechCrunch article before having a paying customer. I should be scaling slowly, with confidence, and building a good business. 

(3) Customer Development 

If I am able to secure a few people who are interested in trying my solution to their problems, it is crucial to be very committed to their success. That means expressing constant gratitude and being diligent about timelines and features. They should know that it's going to be a rocky experience this early on, but they should also know that I will deliver on the $$ they pay me. I don't agree with "selling the idea" — I should be able to give them value where it's due, and be accountable to these early users. 

(4) Technical Acumen

I've read the Ryan Hoover post that you don't need to be technical to start a business. I'm also following the various products that allow you build a no-code MVP, or outsource your development while still having full control. They are all valid, and in many cases I'm a huge fan of what they've built, but they're not something I personally subscribe to. At the moment, I'm largely non-technical, but plan to dive deeper into coding this coming year. I believe I need to be somewhat technical to successfully run a business — whether it's building 10% of the MVP, clearly outlining what needs to be built to early hires, or explaining to my first customer what's going wrong when the MVP (inevitably) crashes. I don't want to handle the business side, I want to build a business. 

Cali or bust? 

There are a lot of benefits to being in San Francisco, that I had an idea of when I wrote this post, but couldn't fully grasp. The concentration of tech talent, and the communities between them, is a game-changer. This happens both at an earlier stage, where new grads and young professionals are enticed by an environment with a high concentration of companies, job opportunities, and mentors, as well as at a later stage, where finding a CTO that has scaled an engineering team from 5-25+ in a specific industry doesn't involve a worldwide search. 

This latter point is especially fascinating to me, and a huge win to San Francisco. There's no doubt that you can start a company almost anywhere, and while growing it may be easier in The Valley, it's not a necessity. However, at a later stage, I find it hard to argue with the logic that being located in The Valley is a significant advantage. Finding people to scale your org is one thing, but it's another altogether to find someone who has done it before, and even more so if you're particular about the industry / space you play within. 

The weather is also a huge benefit. I'm not ashamed to say that I laughed when I saw it snowing in April in Canada, while it's 15C - 20C year-round in San Francisco. It rarely rains, making the climate quite desirable. At the same time, you also miss out on the passing of seasons, which is highly associated with the passing of time, the various activities that are native to a specific season, and the different fashions that come with them, respectively. I don't miss -30C weather and multiple feet of snow, but there's something unifying about growing up in that environment. 

The salary conversation is a difficult one. Yes, it's way more expensive to live in San Francisco than other cities. I paid for a single bedroom (3 people, 1 bath) in San Francisco what would get me a comfortable one bedroom condo in Toronto. With that being said, salaries are also inflated to give you a reasonable standard of living, so in my opinion it balances out. 

All-in-all, I'm not a fan of the "Cali or bust" mentality, unless it's well thought out. Do I need to be in San Francisco as an early-stage founder? Not really, but it might help. If I wanted to be an Associate Product Manager at a mid-sized tech company, should I be here? Probably a good idea. 

Becoming a better marketer 

I've mentioned in past posts as well that I had an irrationally high level of confidence going into my role at Clearbit. For some reason I thought that a string of internships and contract work made me suitable to be solely responsible for driving the growth of a product. After many failures, and a lot of team support, I'm proud to say that I've learned a ton about being a competent marketer. 

First, my ability to write copy has improved significantly. In school, I was used to essay-format, where structured introductions, content, and a specific type of prose was looked upon favourably. That's not the case in marketing — get your point across quickly, use a tone that matches your company's brand (took a while to learn, very key), and ensures your call-to-actions are clear. When I first launched campaigns at Clearbit, the copy required multiple rounds of review and performed poorly. Upon leaving, some campaigns I launched had 2x to 3x higher click-rates and higher conversion rates. Long story short (pun intended) — copy matters! 

The other area I improved significantly in was analytics. Last summer, I worked on the Rev Ops team at Shopify Plus, having to learn SQL, how to attribute marketing spend, and calculate sales performance. I was thrown into the deep end at Clearbit when I was tasked with developing a dashboard that reflected all these stats — except it hadn't really been done before. More than SQL (although those skills have improved), I learned the importance of diving into the logic behind analysis and dashboarding. Yes, I can explain the tables that I pulled from to calculate churn. But what is generating those numbers? Are tags firing correctly when someone signs up? Or should we revisit how we set up the tracking? Questions that are extremely important at a startup, and a general approach that is useful at all levels. 

Lastly, I learned the importance of setting expectations and working with teams. This is universal to anyone in the work force, but not something I grasped when completing internships. With a short-time internship, the timeline is short — the first month is spent ramping up, 1-2 additional months of gauging expectations and trying things out, then (maybe) a month of executing. With a full year, I hit that last stage by December, and had an additional (8) months to make an impact. 

What this did was force me to have candid conversations with my boss and team about what I was able to do, what I was interested in doing, and what I wanted to learn. Balancing these factors was a huge focus for me, as it would allow me to get the most out of my internship — learning a ton, but also having something to show for it. I also learned how to work with partnerships, a beast that requires a lot of attention, cooperation, and accountability. My work with Zapier started as a simple conversation on how to promote our app, and a year later, evolved into a guest post on their blog (1M+ readership) featuring Clearbit and a happy customer. 

Managing life

While my professional development was great, the biggest win from this past year was my personal development. I took the college environment for granted — you're surrounded by people your age who are trying to figure themselves out, and by consequence (either artificial or not), you're in an environment where doing so is encouraged. 

The workplace is a very different environment. While my colleagues were very fun to be around, they were largely in their late 20s or early 30s, meaning discussions I was just beginning to have (i.e. perspectives on life, hobbies, etc) were ones they've been having for the last decade. While this stalled me for a while, I eventually decided to take this problem of self-actualization by the horns. 

I quickly realized that career aspirations, which had an incredible focus in college, were only a part of life. Over the next 10 years, my career will progress (at varying paces), and that happens almost automatically. What doesn't happen automatically is personal development; understanding my value system, and what intrinsically motivates me and satisfies me.

Beyond that, there's the question of lifestyle and routine. How I handle stress and the ebs & flows of my relationships (both related to work and not) can make or break my entire day. Understanding when I'm most productive, how to plan out my day, and know when to call it a night is crucial to my mental & physical health.  

Another big part of self-actualization is building a strong support system, something I didn't have when I first moved to San Francisco. I started to really contemplate who I enjoyed spending time with, how I make time for those people, and how I support them in their lives — both career related and not. There's only so much time in the day, and I'd rather have 10 good friends I can depend on than 30 acquaintances I occasionally spend time with. 

I don't have all the answers to these questions, and that's something I'm content with. After all, I'm only 21, and it's more important to ensure I keep thinking about these questions instead of worrying about whether I have the answers to them. Needless to say, I'm far more concerned about how I manage my life over career progression. 

Conclusion 

This year has been an unforgettable one, and I hope this lengthy post conveys some of my thoughts & emotions. On one hand, it was enriching, eye-opening, and helped me mature a lot. On another, it was isolating, depressing, and made me question a lot of my motivations. Regardless, a number of people made this year what it was, and I want to end this post by highlighting them. 

First, it's obvious that none of this would have been possible without the Clearbit crew, led by the ever-inspiring Alex MacCaw (CEO). It's one thing to take a chance on someone. It's another to hire someone in a different country, off a Tweet, with limited experience and no guaranteed payout. Alex, I can't thank you enough for hiring me and making this year possible.

I also want to give a huge shout-out to my boss, Matt, who was not only an amazing manager, but also a phenomenal mentor and friend. I came in as an overly-eager intern, with high expectations of what I would do, and you took that in stride — helping me ramp up, become a part of the team, learn what I wanted, and make an impact on this incredible organization. 

My parents, and the amount they support me regardless of the decisions I make, are the foundation to my life and I can't thank them enough for that. For any 1st gen or 2nd gen readers, you'll relate to the fact that my parents grinded insanely hard to allow me to access these opportunities, hold myself to a higher standard, and strive for a life that is 10x what I currently have. Money and achievement are not the only goals, but I feel it's not doing them justice to settle for mediocrity, when they overcame all the odds to give me a middle-class upbringing in a first world country. 

To my friends, both new and old, I want to thank you for supporting me throughout the year. There are obvious examples of this, like hanging with me in a city I wasn't familiar with and making me feel welcome, and less obvious examples, like sporadic check-ins that helped me get through some tough times and challenging decisions. I can't wait to see how we grow together and the things we'll accomplish, all while having people to spend it with. 

Lastly, I want to thank myself. I'm a meticulous planner, and there were times this past year where every week seemed drastically different and unexpected. Times where I thought my productivity at work was dismal, I was treating people poorly, and lacked any concept of a horizon. But perseverance is key — it's what makes us stronger, happier, and seek meaning beyond the present. 

I look forward to the coming year at school (Huron College) and what it brings. I can't wait to dive deeper into my interests, learn to be a better coder, and launch my own company. To all the surprises, disappointments, and unexpected outcomes — I'm ready for you. 

City life

View of San Francisco from the LinkedIn office (thanks Jay) 

View of San Francisco from the LinkedIn office (thanks Jay) 

Traveling is often seen as an opportunity to see a new city — visit tourist attractions, try new foods, and overall just to relax. After all, traveling is often associated with vacations, and the last thing you should be doing is working. 

Over the past year, I've had the privilege of visiting a number of cities for the first time, across North America. Some were in the Pacific Northwest, like Vancouver and Portland, others on the West Coast, like San Francisco and Los Angeles, and a handful on the East Coast, like Boston and New York (where I'm currently writing this post). 

In a lot of ways, I succumbed to the typical approach of visiting a city. I had a list of places to go and restaurants to try, making it a priority to check them off my list. At the same time, I had an urge to not just see the city, but experience the city — to understand the people that live there, their attitude towards life, and how the city affects that. 

In this post, I'll be diving into the differences I noticed in the cities I visited, how I think it affects one's lifestyle, and what that means for me moving forward. 

Physical factors 

There are some stark differences between North American cities that even Captain Obvious would laugh at. It snows on the East Coast, rains heavily in the Pacific Northwest, and has a temperament climate on the West Coast. 

This affects you depending on what you're looking for in a city. If you hate the snow, then maybe the East Coast isn't the best fit. If you don't really care for nature, the Pacific Northwest won't have the same allure. These are observations that are easy to make. 

I found physical factors to have a reasonable impact on where I want to live, but less so than other people. Growing up in Canada, I'm used to the snow, extreme weather (hot/cold), and a bit of nature to enjoy. Moving to San Francisco and having the same weather year-round was odd and also wasn't necessarily a good / bad thing. With that being said, I'm sure someone who lived in LA and moved to Toronto would be shocked by the snow, and will probably either love it or hate it. 

The reason being, that physical factors dictate a lot beyond what the city looks like. In Toronto, there's winter style, summer style, etc. In San Francisco, that's really not the case. From another angle, there's a changing of seasons in Toronto, and that helps you identify with the passing of time, whereas in San Francisco, it looks the same year-round, so it can be hard to tell. 

Transportation 

There are also observations that will take some more thought, like analyzing how the city is built. I rented a car when I visited Los Angeles a month ago, and it was a decision I'm glad I made. It can be 45-60 minutes from Venice Beach to Koreatown, and similar distances to the downtown, Santa Monica, and other areas of the Greater LA area. 

The lifestyles of people who live in LA are impacted by this factor. Compared to New York, where the entire city is accessible by 20-30 minutes on the subway, people I met in LA had to think more deeply about their plans and friend groups. If you live on the Upper West side in NYC, grabbing drinks with a friend in Manhattan doesn't take a lot of effort. For someone in LA, there are a ton of factors — is there parking where I'm going? How is traffic? Will I drink too much to drive? How badly do I really want to see this friend? 

Chatting with a friend in NYC who moved from LA, these were all valid considerations. It led to a smaller friend group, largely based by where in LA you lived. In New York, that isn't as much of a concern, so your friends are spread out across the city — and you typically have a lot more of them. 

Now contrast that to San Francisco, where the subway (BART) only runs through one part of the city, and Uber is necessary to get anywhere else. I never go and visit my friends in South Bay (San Jose, Mountain View, etc), and rarely go to the West side of the city (Outer Richmond, Sunset, etc). There are distinct communities based on where you live, and a divide between SF proper and the surrounding Bay Area. This changes based on the city you live in, and affects how large your friend group is and what you do with them. 

Attitude

The biggest difference I've found between cities is the attitude that people have — towards work, friends, and really just their general outlook on life. In LA, the vibe was pretty laid back, with people working hard but taking time to enjoy the weather, restaurants, and shopping. Conversations with friends here showed me that there was rarely one hard focus (i.e. work, specific interest, etc), and things definitely moved a little slower. 

There's nothing inherently wrong with this, but it made me wonder what type of person I'd be (or need to be) to live in LA. Draw a contrast to New York, where most people I met were laser-focused on a specific goal or interest. A friend working in education technology wasn't distracted by what else the city had to offer, instead spending 90% of his time on work or other endeavours surrounding that interest. The same went for people in finance, advertising, etc. It's a city that moves fast, and you either know yourself before going in, or the city dictates it for you. People I met weren't necessarily happy with their current lifestyles, but they knew their goals and why they were doing what they were doing. 

Now a final contrast to San Francisco; I found that despite all the stigma around brutal work culture, the city itself upholds a good work-life balance. People are larger companies (Google, Facebook, etc) commute from SF to South Bay (~ 1hr), putting in reasonable hours from Monday to Thursday, and working remotely (from the city) on Fridays. Weekends are an open window — trips to Tahoe, day drinking at Dolores Park, and lining up for brunch on Sundays. Everyone works hard, and stays accountable to their projects, but I found SF sits in the middle of the spectrum between LA and NYC — there isn't a laser-focused mentality, but there also is a fair amount of direction around what you're doing. 

Conclusion 

So what's the verdict — what is the best city to live in? I think the answer is: it depends, largely on your value system and what your goals are. If you're young, very interested in a specific area, and want to commit to that, maybe NYC is the place for you. If you're more interested in personal development and a more chill culture, then LA could be a better fit. And if you're... Well, if you're in tech and want to maximize that, then SF is a solid choice. 

Unfortunately I didn't spend enough time in Portland or Boston to have a solid opinion on them, but I know they both have their unique allure and culture that you'd have to experience to understand. Boston is flushed with post-secondary institutions, has distinct areas like New York (Cambridge, South Boston, downtown), but to a smaller scale. I didn't feel it being very fast-paced, but the industries (healthcare, tech) that thrived there fed into the vibe. Portland is known for craft breweries, nature, and a hipster culture, but I couldn't really place the work culture or general vibe. 

There are a bunch of externalities to this that I didn't mention, like if you value being close to home, have a significant other, etc. Personally, I'm not sure where I'll end up after graduation. But I'm glad I visited a bunch of different cities to see what they're really like, and chatted with people living there, as it really gives you a better sense of what that city is like (and if it's a good fit for you).

Leaving mobile

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One of the distinct things I remember about first moving to San Francisco is the isolation. New city, new job, and your closest friends are thousands of miles away. After a few weeks, I finally started to get into a groove — work became more routine, it didn't ruin my day when a homeless person yelled at me, and I even stopped converting USD to CAD! Social apps, however, still made me feel like I was missing out on something. 

There were some evenings at the office where I'd get a Snap from someone at school, raving about how amazing a house party was. I'd stroll through Instagram, see smiling familiar faces, and wonder why I wasn't having as much fun as they were. Even Facebook gave me a bit of FOMO, the number of times I'd be invited to an event just to realize it was in a different country. 

I've since moved past that, but a big part of that shift in mindset was understanding what matters most to me. People, activities, things that I genuinely enjoy and don't just do for the sake of doing them. For once in my life, there was no real 'norm' of what I should be doing, no obligations to social events, or similar lifestyles that I could relate to. 

The role of mobile

So how does this involve mobile? I started to notice and question some trends in my behaviour. For example, I'm guilty of taking Insta stories of food, cool events I'm at, and even the periodic post with a relatively witty caption. The question I couldn't answer to that, is why do I do it? 

It's a known fact that humans enjoy social validation. A lot of the things we do, and talk about, make us feel better about ourselves when someone notices and comments. Social media makes it even easier to get this, since it takes little effort to pull out your phone, grab a photo, and throw together a caption to share with your XXX followers/friends. 

I'm a little ashamed to say it, but it's hard for me to do something I genuinely enjoy — whether that's eating good food, working out, etc — without feeling the need to share it online. This is a little frightening, because it really made me question why I did those things in the first place; was it for the activity itself, or the validation I got from sharing it? 

The other aspect to social media that has recently unnerved me is the idea of connectivity. I used to find it absurd when people would "quit" social media for a defined period of time, leaving their phone number if you really needed to get in touch. Now I do see the allure: who really wants to talk to you? 

Sure, it's easy to be swiping through hundreds of Insta stories and send a message to someone about something they're doing, or comment on a post while you're aimlessly scrolling through Facebook, but what level of connectivity does that really show? 

For me, I thought more about who I really enjoy spending time with. Who would I message out of the blue, feel like something's missing if I haven't chatted with them in a while, or reach out to for advice and consolation for things happening in my life? Out of 3,500 friends on Facebook, is it optimistic to say 50 people fit that bill? 

It's a goal for me this year to start making meaningful relationships with people I care about. Talking on a regular basis, reaching out when I'm feeling off, and spending time with them when I can. I think that only happens when I limit other interactions, only doing things that I know I'll find satisfaction, happiness, and energy from. This led me to try an experiment that I hypothesize will help me get closer to that goal. 

Trying something new

Like any habit, it's hard to kick right off the bat. So my initial challenge was to delete the majority of social apps off my phone — Instagram, Facebook, Snapchat, etc. I left Messenger on there as a communication tool, but after a few days, the results are already noticeable. 

I don't feel like I'm missing out on as much as I was before. Sure, it does make bathroom breaks a little boring, but if I'm having eventful bathroom breaks, there's probably a bigger issue there... 

I also have less of an urge to check my phone. It's helping me be more focused when I'm at work, and actually be engaged in tasks or activities I'm doing, i.e. school work, watching a video, or even writing this post! 

As a closing note, I don't think social media is a bad thing. I don't plan on deleting Facebook or other mediums anytime soon, but I hope that this break from mobile apps will help me focus more on myself, personal development, and doing things I'm passionate about. I also imagine I'll feel less of the FOMO I used to, and that will help me be more present in the things I'm doing.

Have any of you tried leaving social media, or some variation of it? I'd love to hear what works for you, and what else I can try. 

Staying motivated

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I feel quite privileged to be able to write a post like this. Billions of people, many even within Western societies, hold responsibilities beyond what I could ever imagine having to deal with. I've seen countless posts for Father's Day that praise dads for persevering, having a deep rooted motivation to provide a better life for their children. I know my father reflects that, and I'm thankful for him everyday — that, to paraphrase Aziz Ansari, "My parents grinded so I didn't have to". 

Now with that being said, I'm far from being without responsibility. It's those circumstances that were overcome that heavily influence the goals I have today. Aspirations to not only attend college but do well in it, get a solid job in a respectable field, and take every advantage of the opportunity that my parents afforded me. 

I hope to outline my thought process around goals and motivations in this post, share some of the experiences I've had, and raise some questions to anyone reading. 

Finding goals 

I've written in past posts about the 'sprint VS marathon' mentality, and how a lot of my goals in previous years were very short-term and built around the herd mentality. You're judged by your academic success, so it should be a goal to achieve a good grade, whatever that takes. You're judged by your career readiness, especially for those who are inclined towards careers in business, so you're judged by the internships you get. This is a very reactionary approach to goal-setting, and one I fell into (and continue to fall into) too many times. 

Attached to this idea is what I would call 'expected goals'. If you are in a certain position, with certain opportunities, there is a bare minimum that you should be able to accomplish. If you're in business school, it isn't enough to get a job in business — that much is expected of you. After all, if your parents paid thousands of dollars in tuition for you to receive a business education, shouldn't you at least get a job in business? This mentality extends, in my opinion, to a lot of disciplines. If you enter college as pre-med or pre-law, it's an expectation to get into med school or law school, respectively. Studying software engineering or computer science means you should be getting a job as a developer. It's not so much a goal, as an expectation

For me, this meant that a lot of these 'expected goals' were motivated by fear — that if they weren't accomplished, I would be a failure. Hence, I tried to navigate life in a way that would raise the probability of those goals being achieved. Even though the college experience should educate you, challenge you, and leave you an enriched member of society, concepts like 'bird courses' and 'easy professors' are tossed around. There are even groups where these concerns are the main ones raised when choosing courses. 

I started to give 'expected goals' more consideration throughout college, but not in the ways I should have. For example, I learned that it was easier to do well in classes I was interested in. Pursuing jobs that leveraged my skill sets, and what I enjoyed, were easier to obtain than otherwise. This has led me down a rather unique path — namely, a Political Science major with a background in growth marketing for tech companies. 

I've given goal-setting an increasing amount of thought in my year off. In a lot of ways, working in growth at a startup in San Francisco was my goal throughout college. Hence, when I actually got here, I was a little lost as to what my next steps should be.

That led me to really wanting to challenge the idea of 'expected goals', and start defining pathways for myself that reflect what I'm really interested in. If I want to start a company, I should be building a skillset that better equips me to do that, not choosing opportunities that will give me the most external gratification from friends & family. My current role gives me that opportunity, but that should be the reason I'm motivated to do it, not the end goal of being in a specific role.

So how do you choose these 'real goals'? Unfortunately, I don't really know... But there are a few things that have helped: 

  1. Read. Read different subjects, areas of interest, and take notes on what you learn, are confused by, and outright dislike. Recently, that hasn't taken the form of business / entrepreneurial books, but ones around philosophy — buddhism, historical thinkers, and modern philosophers. It's NOT relevant to my career, but it does help me reflect on my goals, approach to life, and why I do what I do. 
  2. Talk to people. Can you remember the last really good conversation you had with someone? Why was it great? Are there others that come to mind? Surround yourself with people that challenge you, stimulate you, and support you through life. I've been making a conscious effort to invest more in those relationships, and I'm grateful I did. 
  3. Do. If you have an interest in web development, hop onto Code Academy and start learning. Set your mind on a project and try to make it happen. If it's medicine, fix your mind on an area or problem and dive deep into it, with a goal of what you want to learn. I'm trying this with entrepreneurship — validating ideas, talking to founders, and seeing what really makes me tick. 

Motivation and over-achieving 

There is a stark difference between over-achievers who have 'expected goals' and those who have 'real goals'. The former are constrained by the expectations (as the name says) placed on them from external sources. If the expectation from school is to get a job in your field, then an over-achiever will strive to get the best job in that field. Anything less is a failure, right? 

In my experience, staying motivated in that boat is very challenging. There are many forces that are out of your control, and no matter how you try to de-risk it, eventually you can lose motivation. Contrast the two goals below as an example: 

  1. "I want to get a job in Silicon Valley for a tech company" 
  2. "I want to build a product" 

Goal #1 is binary — you either get it or you don't. There are other forces at play (i.e. visas) and restrictions that could make it more or less challenging to achieve. You can be motivated, but if that motivation is tied to a binary goal, you basically have to be putting in 110% effort until you achieve it. And when you get it — then what? 

Now consider Goal #2, which is not binary. There are a variety of roles you could work in — marketing, sales, engineering, etc. You're not restricted by location, salary, or any other (arguably) binary variables. Instead, it's a goal that is driven solely by you, and is rooted deeper than Goal #1. It also, in my opinion, never really ends. You can build a product, but are you happy with it? What can you do to make it better? Did you build it the way you wanted?  

I can think of a handful of explanations for why someone wants Goal #1, but I cannot even begin to imagine the motivations for Goal #2. When you set goal(s) that are 'real' and reflect who you are, then the motivation becomes rooted in something deeper than the outcome. It involves what you learn, and that shapes how you think about the goal. 

So how does this relate to over-achieving? Simply put, Goal #2 is a lot harder for an over-achiever. Since it's not binary, and has an arguably wider scope, you're left wondering how to over-achieve. If it's a goal that's strictly built by you and meant for you, then is it even possible to over-achieve? I haven't exactly come to terms with this, nor do I have a good answer, but the implied answer is "no". As long as you're moving towards that goal, you're achieving it. 

Conclusion 

Goal-setting and identifying what motivates you is a very scary experience. It challenges what you believe in, what gets you up in the morning, and what shapes your outlook on life. A lot of people that I think have this down are not 'crushing it' from an external point of view. If you held them to the 'expected goals' we discussed earlier, they probably wouldn't do too well.

That's because it's hard to rank someone that isn't playing your game. And if you're not playing, then it's no longer about winning or losing, since you're enjoying yourself either way. As a final note, I am terrible at internalizing this perspective, but it's a goal of mine to do so. I think that doing so makes 'staying motivated' a lot easier, and will give me more purpose and fulfillment than I currently have.