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.


 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.


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.


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. 


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. 


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. 


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. 


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


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


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. 


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. 

How good are political party emails?


Although I'm physically far removed, being in another country while my provincial elections take place, I'm far from isolated. Like with any industry, politics is no stranger to marketing and technology. While some campaigns still painfully hit the phone lines, major political parties vie for voter attention via social media, email marketing, and other channels. 

I subscribe to a number of these updates, and want to use this post to explain what can be improved. It shocks me that while companies around the world are striving to improve customer experience, email communication is so behind. I'll review emails from all provincial parties (PCs, Liberals, NDPs, and Greens), giving my thoughts on what is good and what can be improved.  

Unapologetically cynical (PCs) 

I get it. You want my attention and the best way to do that is to anger me — make me frustrated with what our current government is doing, why opposing parties are getting it wrong, and why your party has the answer. I respect that, and if it's well-reasoned and informative, then by all means, keep it coming. Here's an example from the PCs: 


I get that you're angry from the results of a pollster, and I'm sure some Ontarians will be discouraged to see that the NDP is that far ahead. It may even discourage them from voting. However there are ways to point out that the poll is bogus without resorting to what is essentially complaining. 

"They're lying again" — what image does that give me in my head of the potential, future leader of our province? You've got my attention, but not for the right reasons. A good marketing email should capture the attention of the reader, have coherent content, and leave them better off than before. On that second note, let's move onto the copy. 

"They’re calling it a poll, but it’s junk science. They did the survey online, and it was 802 people."

Again, this tone is the last thing that I'd want from any politician, political party, or government. I get the craze around making emails feel like conversations, that I'm on a 1:1 with Doug Ford and he's explaining his frustration over the recent poll, but this type of content just annoys me.  

Naturally, the ending of this email (like all of them) is to donate. Somehow, donations are going to fund campaigns that get them the win. That is the only thing that a reader can do to help. I don't see any call-to-actions that encourage me to share the truth (which is the goal), volunteer my time, or other solutions. All the parties want is your money. How is that supposed to motivate me to vote for the party?! 

To avoid this turning into a hypocritical complaining session, I'll suggest a better email below: 

Subject: The NDP have 43% of the vote? 

Hey Trevor,

There was a misleading poll by a company called Pollara that stated the NDP have 43% of the vote, compared to the Progressive Conservatives at 32%. This is false, and you need to know why. 

The survey only included 802 people and was conducted online. This is far from scientific; it is not nearly big enough to represent Ontario, {{your city}}, {{your riding}}, and most importantly — you. 

Your voice deserves to be heard, and together we can make that happen. CBC's Poll Tracker reports that the PCs are leading the province, but we need your help to guarantee the win. 

There a number of ways you can help — just click below and give even a few minutes to give this province the leadership it needs, a Progressive Conservative one. 

{{donate now}} .  {{volunteer your time}} . {{share this message}}

This is far from a perfect email, but it's easy to follow, has a tone that is relatable to voters, makes them more informed of the issue, and gives them something they can do about it. 

Confusing and Lengthy (Liberals)

Let's take a look at a Liberal Party email. The subject line already is confusing — does the regular Ontarian know what GOTV even means (Get Out The Vote)? I can only imagine that open rates are extremely low amongst political parties, and I don't see how this would help. 


Secondly, the text blob is giving me a headache. I'm going to assume that if you have my email, you probably know what riding I'm in. If that's the case, why not just use Liquid to only send the candidate that matters to me? Do I care who is running in Windsor if I live in Mississauga? 

This might feed into the issue of lack of data in politics, and the danger of public opinion if you collect it, but I don't see how someone will take the effort to find their candidate in this list, and THEN take action on it. 

Lastly, let's take a look at the call-to-action: 


There's a weird switch in the call-to-action that focuses on volunteers. A basic rule in email marketing is that the focus should be narrow, and the call-to-action follows that. To drop a bunch of names and then ask me to support volunteers doesn't directly connect — is the goal of the email to get me to vote, or to donate?

If it's the latter, which by the subject line it looks to be, then why mention the candidates at all? Wouldn't it make more sense to solely focus on the volunteers, maybe highlight a success story of a senior citizen or new immigrant that's been helping out, and then focus on donating to thank them? 

On the right track (NDPs) 


I've taken a look at a few NDP emails, and I have to applaud them overall. It's hard to pick at any distinct pieces that make their emails objectionable. The subject makes sense — I'm either going to choose their government, or the PC government: 

The body connects well to the subject line. They start by outlining what their future could look like — less student debt, lower hydro bills — and then show what the other future could look like — budget cuts and terrible hospital visits. Although the call-to-action is hard to read, given that it's (3) lines of hyperlinked text, it follows a strong narrative and I am enticed to click it.

A little tweaking (Greens) 

In the spirit of being completely non-partisan, I knew I had to include at least one email from the Green Party. There are some improvements that can be made, but overall it's a solid effort: 


While the subject is vague, the content of the email has the right approach. The goal of this email is finally NOT to have me donate, but instead to have me vote. There's a link with details on what type of ID is needed to vote and information on when voting occurs. Sure it would be nicer with an infographic or something sharable, but relatively speaking this is a good email. 


It's common knowledge among companies that spamming your users, even with useful information, is most likely going to result in an unsubscribe, being reported as spam, or a direct reply complaining how annoying the emails are. 

I counted — 5 emails from May 24 to June 1 from one political party. That's almost an email everyday! I understand advance polls were approaching, and you needed to get your message out, but is a flurry of emails the best solution? Imagine if your parents emailed you 5x per week, each time berating you with details, issues, and complains about an event that's coming up. You'd probably be annoyed, but you'd still hear them out, help where you can, and most likely show up to the event, since they're your parents and you care. 

Now imagine that's a political party. The event (voting) is coming up, and they're trying every which way to get your attention. You have the option of ignoring it (unread) or telling them to stop (unsubscribing). Neither of those will result in a positive benefit to the political party, especially not a donation. 


I hope if anyone involved in politics is reading this, they can take this advice to heart and give some serious thought to how they're communicating with potential voters. From what I've heard, some of these email lists contain tens of thousands of people, and I'd be genuinely curious to see what the engagement rates are like. 

If there's two pieces of advice I can give it's to stop focusing on donations and give the voter something to care about, a track to becoming a bigger part of the party, and empower them to want to donate eventually. The second would be to pay a lot more attention to the approach of an email, thinking more about subject lines and how the content should flow. 

Misconceptions about startup success


Startup culture can be very nuanced, especially to someone who isn't engaged in it day-to-day. Having contracting for various startups and interning for larger tech companies, I made some assumptions about what classifies a 'successful startup', and how to dismiss others. 

Approaching my one-year mark in the Valley, I've had the privilege of diving into startup culture first-hand. This starts with my current company — dealing with customers + learning about how they see the landscape, and especially chatting with my colleagues who have worked at various tech companies both in and out of the Valley for years. 

In this post, I'll explain which misconceptions I use to have around successful startups, and some ideas I have around how to sift through the noise. 

"What's your funding look like?"

This is a common question I get, and while it's understandable, it makes me laugh every time. Back home, I use to evaluate startups solely based on this metric. A startup who hasn't secured funding was weak, and the more funding you amassed, the better you were. This was also (unfortunately) a consequence of the Canadian tech ecosystem. Venture capital is more sparse and focused there than in the United States, so it was an anomaly to come across a company at Series A with $10M funding, and hence the first reaction was to glorify it. 

So let's squash that assumption right off the bat — your funding level doesn't indicate very much about the level of success your startup has seen. If you're not convinced, take a look at Startup Graveyard, which has overviews of a handful of startups that 'died' in past years. Notably there's Homejoy (~ $40M), Optier (~ $103M), and Calxeda (~ $100M). 

Funding, in a lot of cases, simply means runway. It's money given to you by a venture capitalist to pursue certain goals, that will run out in X number of months. For startups that don't yet have revenue/a product, the funding might go towards developing it + taking it to market. For startups that are past that stage, the funding might help them take on market leaders + expand their sales/marketing efforts. 

The challenge to this, is that taking this funding keeps you accountable to certain goals defined by the venture capitalist. A startup with $1M in ARR might take a $10M Series A, with the promise of hitting $3M in the coming year. If they fail, they might shut down, and if they succeed, they might secure even more funding to hit new goals. 

This also spills into the idea of employee count — it's possible for a 30-person startup to have the same ARR as a 100-person startup, it's just that the latter raised more capital + hired more aggressively. A company like BuiltWith has less than 10 employees, but has numerous customers including Fortune 500 companies — don't count them out. 

Tl;dr: Funding doesn't indicate success or lack thereof, it's simply one way of growing your startup. 

"Tilt got acquired by Airbnb! They're killing it." 

Being acquired was another assumption I made that indicated a successful startup. The first example is, the famous money transfer product popular amongst college students. They were acquired for ~ $12M cash by Airbnb, which at first glance is incredible. The reality? They raised ~ $67M in funding and had a valuation (the previous year) of ~ $375M.

This is a better alternative to shutting down, but it means that no one emerged victorious from this acquisition; investors took a heavy loss, employees were laid off, not to mention losing their stock options (now worthless). 

There are other examples, even for startups that get acquired for more than their amount of funding. Venture capitalists expect a multiple on what they invest — if it's $10M Series A at a $40M valuation, then an acquisition for $20M is generally regarded as a failure. 

It's also important to note why acquisitions happen. In some cases, it's an acqui-hire: a larger company wants the talent working for a smaller (possibly struggling) company, so they offer them a discounted offer to acquire those workers. In other cases, it's a result of intense competition: a startup taking on Google might gain some speed, but will need an incredible amount of resources to make a considerable dent in their market share. This happens (via funding), like Airtable taking a $52M round to battle Microsoft Excel. But in a number of cases, the company realizes it won't be able to compete, and takes the offer. 

Tl;dr: Acquisitions don't indicate success of lack thereof; they're very circumstantial and can either be good or bad.

"So what defines startup success?"

For an outsider looking in, it can be fairly challenging to (at a glance) determine the level of success for a startup. The main challenge is figuring out what you think is 'successful' — is it a 2-person company that manages to make $1M in ARR with basically no costs? Or is it a 500-person company that has secured $100M in funding and is on the cusp of taking on industry leaders? 

If you're simply looking at a startup from afar, there are some things you can consider to determine whether it's successful in your eyes. For starters, what is the product? Is it something you think is objectively interesting + game-changing?

Maybe you value the user interface (GUI), and how accessible it is. Or maybe you value the actual content of the product; is it extremely powerful, even if you can only use it via an API? For example, I rarely pass judgements on medical tech startups because I don't know enough about the industry + don't find them interesting. But if you show me something in the sales/marketing space, i.e. a CRM for nail salons, you best believe I'll have an opinion. 


There are tens of millions of startups around the world, all with varying degrees of success. The word itself is subjective, and really depends what you're looking for. Don't assume a startup with lots of funding and employees is successful, and don't praise a startup for getting acquired without digging deeper. Startups without funding can be extremely successful too! 

Start by determining what you value in a company, and what you would regard as successful. Don't be afraid to have an opinion about a company that goes beyond emotional reactions, but also don't be afraid to admit when you're wrong. 

I'll handle the business side

Being "technical" and starting a venture

 This is a stock image and I have no idea what it means. 

This is a stock image and I have no idea what it means. 

I use to think that it was a common misconception that you had to be “technical” to have a job in tech. Every software company, whether a giant like Google or a smaller startup like Clearbit, is built with a balance of technical and non-technical people. 

Roles like marketing, customer success, and sales are crucial to the growth and viability of a startup. So to answer that question outright, no — you don’t have to be technical to have a job / be successful in tech. With that out of the way, I’ll tackle the more controversial question of “do I need to be technical to start a tech company”. 

In the first months of a startup, where the idea is still far from validation and the product is laughable, there is a definite need for technical people. In this post, I’ll dive into why I believe it’s incredibly difficult to build a tech company if you’re non-technical, why this is the case, and how I think it can be fixed. 

No vision in building 

It’s quite possible for non-technical founders to build products that can scale, in terms of purpose and product-market fit. When I refer to this, I’m speaking primarily to the business as a whole, not the product specifically. 

From chats I’ve had, and personal experience, non-technical founders don’t have full visibility or understanding in how the product is being built, with relation to its purpose and feature set. For example, if you’re building a product like Slack, there are intentional directional changes you need to make at an early stage to ensure it scales properly. 

I heard this via a fireside chat at the Startup Grind conference with the Head of Infrastructure Engineering at Slack. Had a strong technical backend not been taken into account, with regards to how Slack manages load, handles downtime, stores messages, etc, then Slack successfully scaling at the rate that it did would be near impossible. 

It’s definitely possible to change products at the later stage, but it becomes increasingly difficult the larger you get. And if your core team is largely non-technical, this is something that won’t be seriously considered. 

Building an MVP 

This is a thorn that bugs me to this day, and pushes me (step by step) to learn how to code. In my opinion, getting a product validated and determining whether it’s feasible is not incredibly difficult. It requires lots of conversations, cold emails, and going back to the drawing board when things don’t make sense, but it’s definitely doable. 

The rising popularity of venture capital, and subsequent willingness of investors (especially in the Bay Area) to take risks on largely undeveloped and untested ideas, means that raising capital (as a whole) is easier than ever. The explosion of Initial Coin Offers (ICOs) and angel investors makes that even easier — products, mainly involving cryptocurrency, can raise millions of dollars in capital with nothing more than a white paper (read: collection of thoughts with no product). 

The challenge I consistently face, and have yet to hear an alternative to, is building that “Minimum Viable Product” (MVP). It’s possible to validate VERY simple ideas without being technical — a combination of fancy advertising and Google Forms can give you a sense of whether people are interested and wiling to pay for your product. For anything else (even if it might be simple), it’s hard to create an MVP. Without an MVP, you can’t fully commit to an idea of truly test it out with a cohort of customers / interested users. 

In these cases, it’s possible to hire a developer / outsource the work, but I’ve outlined in a past post the challenges of this — namely that it can be incredibly costly, as the MVP will inevitably change drastically in the early days.

Gaining trust 

Let’s run with the last example — you’ve spoken to numerous people and validated that your business problem exists (read: Step 1) and you’ve vetted an idea that MIGHT address that problem. Now the final step is to build an MVP and see how users react. 

I outlined in the last section the challenges of building the MVP itself, but let’s evaluate the solution of finding a technical co-founder. 

I’ll preface by saying there are a ton of jokes in the engineering community around finding a technical co-founder. There’s even a large Facebook group where people post threads and calls-for-submissions they’ve seen where the “business guy” will give equity to the engineer, assuming they are highly qualified (in their eyes). The extreme majority of these cases are based around foolish ideas, where the “business guy” did no validation around the problem OR idea, let alone would know how to find demand / sell the product if it ever materializes. So, for the sake of this scenario, let’s assume the business problem is already validated, there are potential pilot users, and all you need to do is build the product. 

For someone that is largely non-technical, finding someone to join you on this arduous, early-stage journey is very difficult. The main reason is the aspect of trust; both in terms of your idea and how you plan to execute it. 

What do I mean by this? Imagine you’re in this position, and you find an engineer willing to join you. The engineer builds an MVP, investing many hours into the project. Here is my understanding of their fears, in no particular order: 

(1) You are unqualified

The business guy, despite having validated the business problem, is not able to handle pilot users, find demand, and effectively sell the product. Despite the idea having merit, the engineer now sees his co-founder as dead weight, unable to contribute to the project and leaving the engineer wondering “Damn, couldn’t I have just done this myself?” 

(2) You are uncommitted:

It’s challenging to validate a business problem. I’ve sent about 400 cold emails and 6-7 strong chats with pilot users for a product I’ve been trying to build. This may have taken 2-3 months of on / off commitment, but to an engineer, often this isn’t considered as “real work”. Quite honestly, I don’t blame them — managing relationships can seem a lot less taxing than building a product that actually does something. The caveat is that this balance (and mutual respect) is needed for a business to function. It’s the exact reason why engineers at large tech companies have disdain for “sleazy salespeople” who make the same amount they do, through what they might see as simply emailing + calling various people. If a prospective engineer falls into this boat, they will be very hesitant to jump on board, expecting you to give up the second things don’t work out. 

I’ll go out on a limb and say that the reason most successful software companies are started by two technical co-founders is not because that’s the only model that works, it’s because both people had a mutual respect for each other and were willing to figure out the “business side” together. I strongly believe that this would be a lot more effective if both parties were on the same page. 


At the end of the day, I can rant and argue as much as I want, but this is the tech reality that we live in. So to the original question, of being “technical”, with the goal of starting a company, I find it harder and harder to refute this point. 

The challenge, and what the note I’ll leave on, is that this is easier said than done. Being a developer requires an intrinsically different skillset than sales / marketing, the latter of which I fall into. Often developers are known as people that think logically or systemically, and have a strong math background. Salespeople, in contrast, are known as people that are relationship-focused — they understand how people function, can read reactions, and can frame problems and solutions in ways that many people understand. 

So for the time being, I will be diving deeper into coding / development. I regret that this is the most effective option at the time — it’s definitely not the most efficient. But I believe it will benefit me the most in the long-term. 

1 Year of Blogging


Yearly subscriptions are a blessing and a curse. On the bright side, it’s an upfront payment that you suffer through and never have to think about again, but renewing is always a challenge. Given that the sum is reasonably large, you’re left wondering whether you made the most of that annual subscription, and if you should indeed commit to another year. 

While I’m still on the fence about subscriptions like Netflix or Amazon Prime, I can confidently say that my annual subscription to Squarespace, which hosts this blog, is one I’m happy to renew. Blogging has given me a lot of perspective on life and opened new doors. I hope to share some of the things I’ve learned after a full year of blogging in this post. 

The Beginning 

I started this blog after returning from a reading week (Americans: spring break) trip to San Francisco, with hopes on summarizing what I’d learned. It was actually during a dinner with a mentor in SF that I was prompted to start a blog. He’ll remain anonymous, for fear of misquoting, but the gist was:

Blogging is a forgotten but invaluable tool. It’s an investment — a reflection of your work + what you’ve learned, and an opportunity to experiment with new subject matter. For a marketer, it’s indispensable.

My first posts were strictly to reflect on my trip to San Francisco, and were more matter-of-fact than an engaging narrative. Silicon Valley 101 and Canucks in the Bay weren’t exactly captivating reads, but they helped me distill my thoughts in a public fashion. 

Unfortunately, few people in my network were interested in reading about a trip to SF, or hearing the stories of people I met (as captivating as they were to me). After 1-2 months of blogging, I had racked up only a few hundred views, leading me to question whether starting a blog was worthwhile. The game-changer was when I started to write for my audience. 

Two of my most popular posts, “How to Get a Summer Internship” and “How to Rock your Summer Internship”, struck well within my audience. Reflecting back, they did so well (~ 700 views in a day) because they (1) came from personal experience and (2) were applicable to my network. 

The hurdle I had to overcome in writing these posts is that they were no longer matter-of-fact; they had opinion, tangibility, and were open to scrutiny. What I realized, was these elements are what makes a great post. 

Documenting your work 

The best bloggers are far from actual experts in their field. The top marketers are too busy running a business to blog. The top engineers are too busy creating products to write about it. And the top financiers know that sharing their edge would defeat the purpose of doing so. 

With this in mind, I came to the conclusion that I didn’t HAVE to be an expert to write about something. So that’s exactly what I started to do — I blogged about SEO, content creation, drip sequences, and more things “marketing” to summarize what I was learning in those areas. Looking back (and take note if you plan on reading them), a lot of what I said in those posts was inaccurate and/or inapplicable beyond my specific use case. Did this mean the posts themselves were useless? 

Not at all. The value here was that I was showcasing what I knew, and this was entirely public. A blog for a marketer is like Github to an engineer; nothing speaks better to a line on a resume than somewhere a prospective employer can see it themselves. 

This was exactly the case when I started to interview at Clearbit for my current role. Despite numerous errors and lack of cohesiveness, it was easy to show them what I knew and what I still had to learn. I regret to say that while the blog landed well, my terrible puns still do not (sorry team). 

Dabbling in the rough 

More recently, I’ve begun playing around with different topics that interest me, and blogging about them. Specifically, I’ve started to blog about finance, building companies, and more things I, quite honestly, have very little hard knowledge about. 

The reason being, I want to be challenged and learn more from my peers. I would love to blog around my opinions on the medical field, or political scene, just to have someone shoot me an angry Facebook message denouncing my work. Controversy creates virality, sparks conversation, and (in my opinion) is the backbone of a strong blog. 

Unfortunately, as I’ve only recently begun experimenting with new topics, I haven’t had a lot of this. But if you’re reading this and want to give me a piece of your mind about something I’ve read, please do! 

Learning from failure 

The posts I’ve written that I’ve learned the most from are the ones that expose some level of vulnerability, combined with a strong narrative. Posts like “21 & Up” and “My Failed Startup” forced me to revisit previous assumptions I had, confront them, and evaluate if they’re still true. For the former, it meant leveling with the idea of “good jobs” and focusing more on finding purpose and value. For the latter, it meant diving deeper into something I wrote off long ago — why did my idea fail, and how I can ensure it doesn’t happen again? 

I hope to continue this trend throughout 2018, as it has helped me immensely in understanding where I’m at in my life, what I should be learning, and where I need to be. Just like keeping a diary, I found blogging to be mildly therapeutic, helping to keep me level-headed, rational, and most importantly, observant of what was happening in my life. 

Consistency is key 

I’m often hesitant to put out a new blog post. Even if it’s been weeks since my last one, I often wonder whether it has enough value, a strong enough narrative, or (quite honestly) something captivating that people will want to read. The conclusion I’ve come to, is that to someone reading, it will. 

I’m sure my self-reflection posts strike better with people my age who might be in a similar walk of life. Posts on marketing get a lot more traction on LinkedIn, getting views from people I’ve never met, and helping them to understand the space better. I know that as I continue to expand my scope of blogging, this will grow as the case. 

The one thing that has hurt my blog traffic and engagement the most is a lack of consistency. No matter how good / bad the post is, I get a lot more engagement if the time between posts is low, compared to if it isn’t. It’s something I’ve given more thought to in recent weeks, and plan to change my blogging frequency to match once per week (if not more). 


It makes my day when I get a message about a post I’ve written. Since starting, I’ve received a handful from people I haven’t chatted with in years, sparking conversations about their life and what they’re up to. 

If you’re considering starting a blog, regardless of the niche or focus, I’d highly recommend doing so. If you’re consistent with it, the value you will get out of it looking back in a year will be immense — both from self-reflection and external opportunities. 

I look forward to blogging more in 2018, and as always (if not more now), reach out to me if you have any thoughts or comments on what I’m writing. 

Investing for Non-Investors


The first job I ever had was a paper route. I had about 33 houses on my route, and made about $25/mth. Say what you may, but in elementary school, this was an enormous amount of cash. I could buy pizza in class for $1.50/slice and occasionally splurge on Yu-Gi-Oh cards. 

Unfortunately, my dad caught on to my spending habits, and gave the most sound investing advice you can give to an 11-year-old: put it in the bank. Safe to say, had I put those meager dollars into Bitcoin back in 2008... Well, we'll get into that later. 

In my personal opinion, a savings account is a bit of a hoax for students. It gives you the allure that you're saving money, since it isn't easily accessible like a chequing account or cash, and makes you think you're "investing" since the interest rate is slightly higher — approximately 0.1% depending on your bank. 

Although I've stressed in past articles that I'm far from a math major, the economics classes I did take in high school taught me that inflation was around 1% to 2% annually. So in reality, by keeping my money in a savings account, I was losing money. 

Coming of age 

I was left powerless at this realization throughout high school, as you needed to be 18 to open an investing account. Eventually, entering university I forgot about it — I come from a fairly frugal household, so saving money came quite naturally and there was never a need to invest. 

Regardless, I was fortunate enough to have a good friend who worked part-time as a bank teller and told me the advantages of building credit early. Even something as small as only paying your phone bill (on-time) via a credit card for a year can make a huge difference to your credit score if you're starting at ground zero. 

It was more of a coincidence that I opened an investing account around the same time, although it wasn't until a few months later that I actually started to use it. As a non-investor and someone that wasn't innately interested in finance, taking money out of a savings account and throwing it into "the markets" was daunting. 

For starters (and if I'm being honest), I knew absolutely nothing about financial markets. Despite appearing business-savvy, I couldn't tell you what exactly a mutual fund did, or an ETF — hell, even bonds were reasonably confusing (am I investing in the government?). So where do you start? 

Understand your tolerance 

The biggest step I made in my approach to investing was understanding my risk tolerance. Basically, if you're in your mid-30s with a spouse and two kids, along with consistent credit card debt and no savings, then your risk tolerance would be quite low. This meaning, if you invested money and lost it, it would probably have a significant impact on your life. For me, I was a student and saved fairly well, so I wasn't too concerned about losing the money I was planning to invest. 

The second part of risk tolerance that I considered was liquidity. Even if your current economic status is not fragile, you still need to consider your short-term goals and what you will need money for. In the last scenario, locking up even a small sum of money for a few months in the markets could be chaotic. Again, in my scenario I didn't need an incredible amount of liquidity in the near-future (2-3 years) since both my parents and I had saved reasonably well. 

What I avoided 

Before I dive into my approach to investing as a non-investor, I thought I'd shed some light on what I avoided, as a non-investor: 

Automated investing

If you have no interest in investing whatsoever, but still want to reap some level of reward from it, automated investing platforms like Wealthsimple can be a great option. You can select your risk tolerance (among other things), and they'll choose portfolios to invest your money into.

For me personally, I wanted to see what I was investing in. If I put money into a company and lost it, I at least wanted the ability to look at that company with disdain for the foreseeable future. The challenge with platforms like Wealthsimple, is that you really can't do this because you don't really know what they're investing in. 

Mutual Funds 

A mutual fund is a portfolio that is actively managed by investment professionals, and aims to beat the market. There are two challenges with mutual funds that turned me off from them. The first challenge with mutual funds was that aiming to beat the market can often go the other way (underperforming). So similar to automated investing, I had little autonomy / responsibility for the money that was being invested. The second challenge with mutual funds was that the fees on mutual funds are significantly higher than trading by yourself, or even an index fund. 

Picking stocks 

My approach to investing was to pick companies that I both (A) understood and (B) believed in. I'll be honest in saying I didn't scrutinize their 10k reports, balance sheet, and other financials because my understanding of them wouldn't have had a significant impact on my investing decision anyways. The other reason for this is that I lean towards long-term investing (2-3 years), so how the company is currently doing isn't as important to me as their vision and track record for success. 

The easiest example of this (and my first investment) was Shopify. I interned there in Summer 2016 and was instantly impressed by everything they were doing — the industry (e-commerce), their various product offerings, and their plans for the future. There was skepticism (and still is) around the business model, leadership, and potential to grow. But that was when the stock was at $45 — it's now at $170. 

The second example of this is Amazon. Similar to Shopify, I was impressed by their track record of growth, and sheer dominance in a number of industries (e-commerce, AWS, etc). I believed (and still do) in them long-term, and was confident that Amazon in 4-5 years would be an even bigger force to be reckoned with than it was a year ago. 

Of course, there are exceptions to this rule. Investing in either Twitter or Groupon 2-3 years ago would have been a terrible idea, as you would have lost 35% or 32% respectively. And if I was in that boat, and had evaluated the model of Twitter / Groupon in 2015 and truly believed in what both their businesses were doing, I would be jaded but ultimately okay with that investing decision. 

Hedging your risk 

Of course, I know that there's a reasonable chance that both Shopify and Amazon could go under, or lose a significant portion of their value, at any time. The probability, however, of the market as a whole losing a ton of value is lower. Obviously not impossible — I'd be surprised if there were 2008 Recession deniers just as there are Flat Earthers — but less likely by a fair margin. 

So my response to this was investing in index funds. These are essentially portfolios with (reasonably) low fees that aim to match the returns of the market. With the exception of the dotcom bubble (2000-2003) and the housing crisis (2008-2009), the S&P 500 has been up consistently each year. Reverting to my initial story about inflation, the S&P 500 is up about 12.5% in the last year, which beats inflation by a huge margin, not to mention any rate a savings account would offer. Therefore, my mentality was that by adding index funds to my portfolio, I'd be hedging against some of the potential risk that comes with investing in individual stocks / corporations. 

Screen Shot 2018-02-11 at 6.37.17 PM.png

Volatile investments 

I have to admit that not all of my investment decisions have been as sound as they should've been. The most recent example of that is the hype surrounding cryptocurrency. I bought into Bitcoin and Ethereum, two of the most popular types of cryptocurrency with the highest market cap, back in November and saw incredible returns. I also invested in a number of "alt-coins"; significantly smaller types of cryptocurrency focused around different problems, many being payment transactions but others involving online gambling (FunFair), Internet of Things (IOTA), and even processing power (Golem). 

I made a crucial mistake with cryptocurrency, mainly because I was investing in something I really didn't understand. Sure the vision sounded intriguing, but the vast majority of cryptocurrency projects are in their very early stages, many without even a working prototype of an idea that is backed by millions of dollars. The only thing I did right with cryptocurrency, and the advice I'd pass to anyone interested, is only invest what you're willing to lose. I've been both up and down by ~ 50% in the last few months, but either way, I'm not going to lose my house if crypto goes under. 


My investment journey has been an exciting one, and I'm glad I embarked on it. If you take anything from this post, it's that savings accounts are not a sufficient investment, and everyone who doesn't have a very low risk tolerance or need immediate liquidity should consider entering the markets. 

As a final disclaimer (if it wasn't clear already), I really know nothing about the financial markets and am speaking purely from personal experience. So if you decide to invest and lose... ¯\_(ツ)_/¯.

21 & Up


I never imagined I'd wake up to 15 degrees (Celsius, I'm not converting) on my 21st birthday. If you asked me at the beginning of university, I would predict that I'd be stressed with my first year of business school and recruiting. A few years earlier, I could have expected this occasion to be a lot bigger, as I had my eyes set on a few US schools, where being 21 brings new-found legality. 

I've written a lot about career advice, choosing pathways, and learning about tech, but I've rarely touched upon the idea of personal development. Not for the sake of scoring a top internship, or making a lot of money, but for truly becoming a better person. Figuring out what makes you tick. Understanding what you did, why you did it, and how that changes what you plan to do. 

It's always a sprint 

As humans, we're very used to 'sprinting' in life. You 'sprint' in high school to get the best grades. Then you 'sprint' in university to get the best internships. Typically, if you 'sprint' for 4 months during an internship, you'll get a full-time offer. Then it's the next sprint — moving up the corporate ladder, exiting from a job you hate into a job you hate less, or rinsing and repeating if you still have no clue

My first few months here followed a similar mentality. I was determined to be the highest performer on my team, put in the most hours, and produce the most results. And for the first few months, it appeared to be working. I launched some unique campaigns, met interesting people, and... I started getting a little bored. 

I expected San Francisco to be this new challenge in my life that would be impossible to surmount, and I'd extract something incredible from it. In reality, I was still working at a company (as awesome as it is), doing fairly typical work, with better weather. It was around this time (November) that I hit a wall and started contemplating why this time was different from the rest of my life / more recent experiences. 

With a typical internship, you're typically put on projects that are short-term in nature, or you play a small part in a larger project. One of my old bosses told me 

At the end of the day, you’re here to learn. I might send you down a rabbit hole with no results, but if you learned something from it, that’s a win

In contrast, being here for a year, a lot of my responsibilities were larger in focus. I was responsible for content projects that went through several rounds of review. I launched email campaigns that took a few months to complete. And I realized that I suck. 

The results from my campaigns were fairly dismal and the content pieces weren't revolutionary. This 'sprint' mentality, for the first time, had failed. Despite numerous blog posts and cool internships, I was, (at best) a mediocre marketer. Why was that the case? 

Still Only 21 

I started reflecting on a lot of goals I had leading up to this point in my life, and how they played out. You compete for the best universities in high school, then the best jobs in university, and finally the best 'exit opportunities' from those same highly coveted jobs. Life is a constant circle of 'sprints', until you realize the majority of those sprints (in context) were meaningless. At the end of the day, I'm still a 21 y/o undergrad that has never held a real job, just as I was at 18, and 14, etc. 

My friend group here has given me a lot of perspective this issue. Two of my roommates are from Wharton, arguably the best business school in the world. A few of my older friends left investment banks and are onto new careers. They've all achieved those conventional levels of success, but spending time with them has given me a new look on the 'sprint' mentality. 

For instance, they think a lot more than I do. Conversations are rarely dominated by recruiting or gossip, as I often led them to be in university, but instead about what books we're reading, challenges we're facing, and projects / ideas that intrigue us. From these conversations, I realize how limited I am in various aspects of life (i.e. handling relationships, mental health, political views). This hasn't led to any enlightenment by any means — but being in such a different environment has led me to the following conclusions on my 21st birthday. 


Having already failed a rather superficial New Year's Resolution, I'll take my early birthday as an opportunity to set some public goals that build on what I've mentioned above for this year, and (hopefully) reject the 'sprint' mentality I've often fell into, and start striving for real personal development. 

(1) Reading 

In university, I've often had to read 70-100 pages per week of dense material on everything from early political philosophers to the economic development of African nations. They were interesting, but I regretfully read them with one purpose — regurgitation and application to their respective course. I rarely applied any of my learning to my own life, or used it to challenge or develop my personal perspectives. 

Hence, a goal of mine is to dive a lot deeper into various genres of books this year that will make me a better person. I want to be able to comment on politics and economics beyond what I read in the news — and have sound reasoning behind why I believe what I do. I want to be deliberate with the time I spend outside of work — the hobbies I have, and why I'm interested in them. 

The following books / authors are a start to what I'm hoping to read: 

  • Epictetus
  • Principles by Ray Dalio (100pg note) 
  • The Upside of Inequality (Edward Conard) 
  • The Lessons of History (Will & Ariel Durant)
  • River out of Eden (Richard Dawkins) 
  • Hero with a Thousand Faces (Joseph Campbell) 
  • The Sovereign Individual (James Dale Davidson)
  • Status Anxiety (Alain de Botton)
  • A History of Western Philosophy (Bertrand Russell)
  • Reasons and Persons (Derek Parfit)  

(2) Personal Health 

I've neglected my health over the past few years in a number of ways — for starters, being a university student, both my sleep schedule (sleeping 5am to 12pm) and diet were atrocious.

Hence, I'm making the commitment to become an early riser, ideally waking up at 6am and sleeping by 11pm. I've tried this with a fairly low success rate over the past few weeks, but I plan to be more religious with it in the coming year. 

I'm also committing to home-cooked meals by buying a Costco membership and using apps like MyFitnessPal to track my progress. I know both sound pretty lame, but I think it's a solid start. I've also have some aspirations for gym / weight goals that I'll deliberately leave out for fear of public shaming. 

(3) Mentors & Skill Development 

I have some incredible people in my life that help to guide my decisions and career path, but I rarely put any deliberate work into finding + nurturing those relationships. First Round put out a great post on how to find a mentor which I've been following, narrowing down my approach to both early-stage founders and growth marketers. Expect a post in the new month or two on this!

I also want to give back in whatever way I can, so if you're reading this and need help / advice with anything, don't be afraid to reach out. I've been scolded in the past for doing this, but I promise you I won't give you the response I once got below. Unless you use a drip sequence like I did... Then I'll commend you on the hustle. 

 Shoutout to drip sequences and marketing! 

Regarding skill development, I'm learning an incredible amount about marketing and growth through my current role, so I have no direct plans around that. However, I am going to make an effort this year to learn how to code. There's an incredible amount of literature out there on the value of coding, even at least knowing what's possible / how to read it, so I'm committing to that for the year. 


Despite all my ramblings about enlightenment, learning, and perspectives regarding life, I want to make it clear that (being 21) this year will still be filled with debauchery, terrible mistakes, and new realizations. I'm not even halfway through my time in California, and I can't wait for how the rest of it plays out. Thank you to everyone's that made this a blast thus far, I wouldn't be writing this without you. 

My failed startup



It would be the app that changed the way people lived — the next Uber / Airbnb / Instacart. I finally found a gap in the market that seemingly didn't have anyone else, so naturally I went full throttle on making it happen. And it failed... Miserably. 

Entrepreneurship is flooding college campuses across the world. Every student, from Ivy League schools to community colleges, has an inclination towards starting their own company. Movies like The Social Network and shows like Silicon Valley have glorified startups to the point where "Co-Founder & CEO" is a LinkedIn title almost more prevalent in a university town than San Francisco itself. 

Schools are jumping on the trend as well. There are more than 1200 university business incubators worldwide, which is 50% more than the number of business schools accredited by the AACSB. This shouldn't be surprising; after all, some of the greatest minds in tech are university drop-outs. But the bigger question is whether this trend hurts or helps university students, and whether the vast majority are prepared for or understand the work it takes to start a business. 

You too can change the world! 

Most college students have an idea for a startup that involves one or multiple of the following: 

  1. Beer / alcohol 
  2. Textbooks / notes 
  3. Housing
  4. Partying  

In most cases, it's tied together with the use of a marketplace app, this being an app that creates a community for two parties (often buyers / sellers) to interact. For a company like Uber, that's connecting drivers and people looking for rides. 

Why marketplace apps? Because they're exciting, social, and can go viral quickly. The allure of expanding to new cities (campuses) and growing a user base is much better than cold-calling & emailing businesses to sell software. 

The rather limited list of ideas is a product of the life of a university student. We often want to make ideas that solve problems we face day-to-day, and those few ideas generally sum up the lives of a lot of university students (myself included). The issue is that there's a problem with the marketplace app + university ideas that really hurts the idea of entrepreneurship. 

The vast majority of profitable, successful businesses are not game-changing or explosive. They take time to validate, rework, and grow. Basecamp, a project management tool, is a great example of this. Founder & CEO, Jason Fried, gives some insight into their story

You don’t have to be Apple, or Amazon, you don’t have to be a wildly-growing company. You can be a really great company building something useful for your customers and treating them well, treating your employees well, and making a great living.

This is a stark contrast to the typical approach of raising tons of capital, growing users, and disregarding revenue or profitability. There's countless examples of startups that pursue this path, and that entices students to think the same way. They rely on "X months of runway" to power a frantic attitude and brutal work culture, in hopes to finding a model that works. Heck, some even IPO without figuring that part out. 

Relentless validation 

I'm guilty of this too. My game-changing idea in 2015 was to create a marketplace for students to lend and rent items. I was frustrated by how much stuff I'd collected over the year, but also wish I could temporarily access items like speakers, DJ sets, and musical instruments for a night at a low cost.

So after polling a few friends, I decided to build an MVP and start gathering users. I paid a firm in India to make a clickable concept, and started building a business model and slidedeck on how it would work. I had learned this approach from previous pitch competitions and startup weekends who preach the idea of 5-year plans and business strategies to make ideas happen. This was my first mistake. 


What I should have done is researched and validated my idea, thoroughly. As unsexy as it sounds, I should have spent a few weeks knocking on the doors of the numerous dorms on campus, gathering emails and polling students on what they thought about the idea. A lot of university incubators back this approach, but unfortunately it isn't enough. 

The reality is that most people say they'll buy / support something, but may not actually. It's better to understand whether people find value in your product, and even better, are willing to put money behind it right away. This pulls from the van Westendorp Price Sensitivity Meter, where you test multiple models before sticking behind one. 

I learned from this in my next attempt to build a startup, which was essentially an AI for content marketing. I called and met with marketers at a number of startups, diving into the problems I thought they had, how they were trying to solve it, and what the gaps are. It wasn't pretty; it took about 6-8 weeks to gather enough information to realize the idea wasn't feasible. 

This sucks. But it's necessary, and this is disappointing in an age of instant gratification. This is especially true on college campuses, where students are constantly prepping for the next test or internship interview, operating on short timelines and goals. We want results right away, and that's not the case with entrepreneurship. 

Fill the crack, don't build the bridge 

The one piece of advice I get from successful startup founders is to fill the crack, don't build the bridge. It's a million times easier to solve small problems for big markets than to try and create a new market for an unseen problem.

Think about software that measures the happiness of corporate employees and gives an aggregated report to management every week. Say it requires workers to submit a 25-word paragraph at the end of each day to a 3rd party app, and the app uses sentiment analysis to show management how their employees are feeling. You can use existing frameworks for the analysis, and train it for what employees might report.

For validation, you can ask some small / medium-sized businesses in your area for their thoughts. Do they have a strong grasp on how employees are feeling? What are current mediums for giving feedback? How much time / money does that process currently take? 

Now contrast that to an app that tries to match students for housing. What are all the intricacies that go into finding a housemate? Who do you ask first? Is there a revenue model that doesn't rely on advertising? How is this better than a Facebook group? Do most students even have the problem of finding a housemate? 

This is an idea I've heard a few times since starting university, and while it sounds great, it's hard to validate and be profitable. However, it's sexy and initially appeals to a lot of university students. If someone knocked on your door and suggested it, asking if you'd sign up, you'd probably say yes. But would you pay for it? Do you really need it? 


Entrepreneurship is the new fad, and game-changing startups are becoming more and more attractive. It's hard to take a step back and evaluate ideas before diving into them. It's even harder to reject wild ideas, and focus on smaller problems that are easier to validate.

At the end of the day, your startup may not change the world, but it can still change lives. Profitable startups provide livelihoods for their employees and support their families. These startups can support local charities and youth sports teams, while their employees can be crucial parts of local communities. That may not be game-changing, but it's pretty damn cool. 

Tone & voice: crafting content that fits your brand


One of the most challenging things I've faced with my new role on Clearbit's Growth team is understanding our brand, and how that fits into the content we produce.

Coming into the role, I was pretty confident with my understanding of email marketing. I knew how to structure a campaign, and even wrote about it in terms of creating a nurture funnel and writing content for various purposes

What I lacked, however, was an understanding of the importance of a company's brand, and how this ties into the content you produce. This is a very large topic, so I'll be focusing primarily on email marketing & email content in this post. 

Separating company tone and personal tone 

As a liberal arts student, I spent a good chunk of my college career consuming content and writing essays. Unfortunately, the tone of an academic paper on the intersection between indigenous and formal economies in Egypt doesn't translate too well to that an outbound campaign for marketers that use Salesforce. 

Your company's brand and voice are naturally going to be very different from your own. Being a startup, our tone is very fun and casual. In a lot of ways, our content sounds a lot like a professional conversation between two friends compared to an expert lecturing a student on a complicated topic.  

For example, compare the two sentences below that talk about Clearbit: 

We’re really passionate about good data. Even after our system verifies a record, we have a dedicated team that checks to make sure it’s correct. Now that’s data you can count on!
Our data is industry-leading. Our system first parses through the contents of a record, then a dedicated quality assurance team verifies that the record is correct.

Both sentences are correct and address the validity of Clearbit data, but the first one embodies our brand a lot more than the second. Besides being more legible, the first sentence also conveys a tone of care and attention to the product, which can translate to a customer feeling more comfortable with a sensitive topic like data management. The second phrase sounds automated and robotic, which is not the best impression for a data company. 

Nobody likes a computer 

Automated emails are a hit or miss — if it sounds like a human wrote it, there's a good chance that the recipient will react and respond. If not, it'll probably be deleted immediately. 

While larger companies and smaller companies may differ in tone, they both understand that content needs to appear human. That means ensuring that any attempts at a mail merge are seamless, and the flow of the email is natural. Choppy sentences or obvious substitutions based on industry, role, etc, will backfire. 

At Clearbit, we dogfood by including a lot of the data we return to our clients in our marketing efforts. That also means that the Liquid in an email template can get quite extensive, and needs to be flawless when sent. 

An email that references the wrong name of a recipient, or has a poor fallback, will be recognized immediately as automated. Hence, we extensively test our emails before any of them go live. 

Marketing vs Sales 

The last piece to content tone is whether it is designed as a marketing campaign or a sales campaign. The two have very different purposes, and need to be built accordingly.

A marketing email is often designed to qualify a lead for the sales team, and can have a broader scope of CTAs and reactions than a sales email. The email may be designed to get the recipient to click a link, or complete a conversion (i.e. signup for the product). This means that there is a lot more freedom with design (compared to plain text) and the contents of the email can be a lot more liberal (GIFs, use of bold, etc). 

In contrast, a sales email is generally designed to get the prospect to respond back and schedule a meeting with the sales rep. This means it should not appear to have any aspect of automation or appear generic, as these emails are meant to be sent on a 1:1 basis. Often the prospect is already qualified, so the opening hook could be very specific (i.e. based on the technology they use) or a trigger that has already been completed (i.e. visiting the pricing page). 

See two examples of emails below (signatures removed), and pick which is a marketing email and which is a sales email:  

First Email


Second Email


The former is a sales email: having plain text, and having a specific ask at the end. The latter is a marketing email: it includes an image, has a more relaxed tone, and the CTA is to click a link opposed to reply back. Since marketing emails are generally sent in mass (i.e. 2,000 recipients), the goal of getting a response is actually discouraged, whereas a sales campaign is the exact opposite. 


A good email campaign can take a dedicated 1-2 hours to crank out, even if it's only 1 or 2 emails in length. At larger organizations, this can include passing it by multiple teams for input and approval. A sales campaign that targets 200 qualified prospects with an ACV of $200,000 could be extremely costly if executed poorly. 

Tone that matches your brand is incredibly important, and can ultimately make or break whether you have a high engagement rate or get sent directly to the spam folder.

Like what you read? Subscribe to my email newsletter below and be the first to know about new posts, what I'm reading, and more! 

#triggered - using intent in marketing campaigns


Human beings are predictable. The common initial reaction to this is anger and disgust - how dare someone make such a generalization?! Freedom of choice and speech is the essence of civilized society, and there can't possibly be predictability to that. 

And to some extent, that rebuttal is right. Humans aren't ENTIRELY predictable, but in a lot of ways, we are. Our demographics, geographic location, and lifestyle choices have an incredible influence on how we behave and interact with the world around us. 

The prime example of this is Facebook Advertising. With substantial amounts of data on you, Facebook can sell spaces on your timeline to brands that want you to engage with them. This is already intriguing at a surface level, but where it really gets interesting is with retargeting. 

 My new job has led me to be aggressively retargeted by software companies on my personal Facebook account.

My new job has led me to be aggressively retargeted by software companies on my personal Facebook account.

If you visit a brand's website, they can tag you with a pixel that connects to your Facebook account. Then, when setting up their Facebook Ads, they can retarget you on Facebook with messaging having known that you've already been on their site. I'll dive deeper into ads in another post, but the main concept here is identifying intent

What gets you hooked? 

In digital marketing, there are indicators in every facet of a business that demonstrate the intent of a user. I've gone over this a bit in one of my earlier posts, and how each page on a website has a different purpose for the visitor. The pricing page might be geared to getting an email from or demo scheduled with the visitor, whereas the case study page might be designed to educate the visitor on the product. 

Just as how a visitor that hits your pricing page has a certain type of intent, your customers/users have different levels of intent depending on their interaction with your product. This is where marketing can really shine - instead of guessing at a vague buyer persona, you can use the data you collect to really dig into what your ideal buyer looks like, and how they progress throughout your funnel. 


That was a bit of a jump, so I'll walk through a cheesy example (literally) to make it clearer. Imagine you're running a pizza deals + delivery app, and you're trying to figure out what marketing campaigns to run. The goal is essentially to drive more revenue, but where do you start? 

Ask yourself the following questions about your existing users: 

  1. How many days does it take for a user to go from registering for the app to ordering their 1st pizza? What does this order typically include? 
  2. How many days does it take for a user to order a 2nd pizza after their 1st? What do these orders typically include? 
  3. Which users order more than a single pizza? What times are these types of orders most popular? 

Starting with those fairly basic questions, we can start to identify the intent of our users BEYOND just buying a pizza / downloading the app. For example, the following conclusions might be able to be drawn: 

  1. 90% of users order their 1st pizza within 2 hours of downloading the app. The average order is (1) medium pizza. Of those users, 40% used a discount code that gets them free delivery.
  2. Users typically order their 2nd pizza about (2) days after their 1st. Only 15% of users had a 2nd order, but of those users, 60% had used a discount code in the past. The majority of 2nd orders include (1) large pizza and 1lb of wings.  
  3. Users with their credit card attached to the app are 2x more likely to have larger orders. These orders are most popular between 11pm and 2am on Friday and Saturday. 

These insights are all incredibly powerful. Each point above indicates a level of intent from the user, and a hypothesis that can be tested by the marketer in a data-driven way. 

A/B Testing?! 

The gut reaction to hearing the word 'test' in relation to marketing is to suggest an A/B test. Just run two different versions of the campaign, and whichever converts better wins! This is great in theory, but in practice there needs to be more thought put into how the campaigns will work. There should be reasoning behind each test version and a desired outcome + way to track it. 

Given that we're already pretty baked into this pizza example, lets run with it to get some ideas for campaigns to test. See below for a breakdown of the campaign name, goal, and details following the number format above. 

#1: Free Delivery Campaign

  • Purpose: offer free delivery as an in-app push notification while on the checkout page, see if this increases the chance of conversion (completing an order) for users who just signed up.
  • A/B test: can free delivery increase the order value? Try only offering free delivery if they add a side to their order. 
  • Logic: 40% of first users are using a discount code at checkout, meaning that's probably an incentive to download + use the app in the first place, so let's test on everyone else. 

#2: Better with Friends 

  • Methodology: send a push notification with a discount code if user splits with a friend (on the app). See whether this increases order value + conversion in comparison to the core group. 
  • A/B test: split order with or without discount code - see what effect the code has on orders if the user is already prompted to split. 
  • Logic: the order size of pizza and wings is fairly large, so we can assume it's for more than one person. If we test to split the cost, we not only can increase order value but also the amount of people on the app.

#3: Late Night Munchies 

  • Methodology: send a push notification around 10pm to encourage impulse purchases after a night out. Compare campaign conversion rate to typical conversion rate. 
  • A/B test: messaging could be especially interesting here, whether appealing to club/bar go-ers, or people that stayed in for other reasons. 
  • Logic: help suppliers by encouraging purchases before the peak 11pm to 2am times. Delivery usually takes 30-45 minutes, so correct messaging can get users their food on time VS ordering last-minute. 


It's easy to come up with marketing campaigns based on general assumptions, but it's hard to justify the spend on them or the structure of the test. Looking for user intent through data is the ideal way to setup trigger campaigns that leverage what you already expect your users to do. And while it is a little sad that humans are becoming more and more predictable, at least we will all get discounted pizza! 

Like what you read? Subscribe to my email newsletter below to get the latest articles, top things I'm reading, and more. 

Intro to Digital Marketing


Gearing up for my podcast this Wednesday with Nspire, I thought I would use this post to summarize the practical part of what I plan to say. Namely, the hard skills you should start building if you want to have a career in digital marketing. 

The Marketing Stack 

There are a number of skillsets that comprise the job of a digital marketer, and are summarized quite nicely in this post by Buffer. I’ve organized them below with short descriptions: 

  • Search Engine Optimization (SEO): increasing the chances your product will be found in a search engine. Learn more here (Part I & Part II)
  • Search Engine Marketing (SEM): using paid advertisements (Facebook Ads, Google Ads) to promote your product. 
  • Content Marketing: the creation of content (video, articles, etc) for your product, with various purposes. Learn more in this post
  • Marketing Attribution: tracking the performance of your marketing efforts (i.e. conversion rates). Learn more in this post
  • Email Marketing: the use of email to communicate with leads or customers. Learn more in this post
  • Partnerships/PR: using other mediums (i.e. news, social media) to gain traction for your product.
  • Offline Marketing: the use of events and in-person tactics to promote your product. 

The goal is to have a general understanding of all of the above areas, but know a select few (1–2) very well. This gives you versatility as a digital marketer, but also a unique value proposition depending on where you are an expert. For me, my t-shape looks something like the image below: 


Tools for Marketing  

Every company has a different combination of tools they use for marketing, but knowing how to use + having a basic understanding of a few can be helpful. I’ve listed the main ones I’ve noticed below: 

  • Content: platforms like Medium are very easy to use, but you can take it a step further by knowing tools like Wordpress or Squarespace. Learning Mailchimp is great for email marketing. 
  • Analysis: the gold standard is Google Analytics, and their academy is free to attend! Excel is very useful, along with SQL, to pull your own data. There’s a free tutorial on the latter here
  • Testing: tools like Optimizely and Unbounce are very common, to A/B test ideas and landing pages. 
  • SEO/SEM: AdEspresso breaks down Facebook Ads pretty thoroughly, while Google Academy covers their ad network. Check out Neil Patel’s podcasts for more on SEO. 

Nailing down some of these skills will make your value proposition as a digital marketer clear, and make it considerably easier to secure a job or internship. If you’re not sure how to start looking, you can read this post.

I'm moving to San Francisco and I want to keep you in the loop! Sign up below for my email newsletter where you'll hear what I'm learning, reading, and doing in my new journey. 

My Next Chapter: San Francisco

 Full credits to Steeve Vakeeswaran and his superhuman abilities to edit on Snapchat. 

Full credits to Steeve Vakeeswaran and his superhuman abilities to edit on Snapchat. 

As an individual, I consider myself to be rather untraditional. I chose an arts degree over a business one, a tech job over a corporate route, and I'm most involved in a fraternity opposed to a career or academically-inclined club. These things my parents have all eventually come to terms with. The taboo in my household is stopping my education - until now. 

One of my good friends sent me this tweet recently about an opening at a data enrichment startup called Clearbit in San Francisco. The ideal person had a background in sales/marketing, but also had a competency for data analysis and working knowledge of SQL. 


Although I had already planned my coming year out fairly well, I'm always on the hunt for a new challenge. Having already done contract marketing work for a few startups, I thought this might be an opportunity to add to my experience. I sent off a quick email with my background, and followed up over Twitter to ensure he received it. He did - and wanted to chat the next day. 

After speaking with different members of the team, I received an offer to join Clearbit in a growth/marketing capacity. The role would be full-time, and I'd have to relocate to San Francisco. This brought up the tricky situation of deferring my schooling, as Western University unfortunately doesn't have a satellite campus in California. 

There were a million things flying through my head at the time, but I hope this post breaks down my thought process in an understandable way. 

The Mecca of Tech 

One of the biggest pulls to working at Clearbit was the fact that they were located in the heart of San Francisco, the place to be for anyone even remotely interested in tech. Having visited the Valley in February 2017, I knew this was the case, and wrote about all of my findings here.  This included the caliber of people and volume/intensity of tech companies that you can't find anywhere else. 

 My favourite photo from my SF trip - getting to meet Evernote CEO (and Huron College graduate), Chris O'Neill.

My favourite photo from my SF trip - getting to meet Evernote CEO (and Huron College graduate), Chris O'Neill.

Although I did consider doing an internship in San Francisco next year, I knew it wouldn't be the same. It would take 1-2 months to get settled, and with a typical internship, that leaves practically no time to develop meaningful relationships and find your groove in the city. 

Hence, the only viable alternative was pursuing full-time employment. I can't predict what the landscape for visas and appetite for Canadians will be in 2019, so the only definite opportunity I had was now. 

Optimize for Learning 

It's often said that internships are great because they help you figure out what you want to do with your life. Knowing that I want to be in tech, I started my journey towards a final decision last summer. I found a strong interest in growth/marketing, and got deeper into the field during my sophomore year by doing contract marketing work for startups. Mid-way through the year, I knew that tech marketing was the perfect fit. 

With that in mind, my next goal was to optimize for learning. I've referenced the t-shape marketer by Buffer in past posts to show how every career path has a diverse skillset that one needs to learn in order to be successful in that practice. Having started the marketing & sales side, the other area to expose myself to was the data analysis end. This summer at Shopify, while interning in business operations, I was able to do exactly that. I worked with SQL every day, felt a lot more confident using Excel, and more importantly knew how to look at problems quantitatively and present ideas in a data-driven way. 

In the last few weeks, I've been reflecting over how I should spend my remaining years at university to continuously build my skillset. The reality is, the amount you can learn/do as an intern or contractor is limited. Even at an amazing company like Shopify, where I can tackle whatever I'm interested in, I still only have 3-4 months to make a tangible impact. Running a marketing campaign or overseeing the build-out of an attribution system is simply not something you can do in that short time period. 

 The Waterloo Shopify intern crew

The Waterloo Shopify intern crew

Hence, the solution was to dive into full-time employment. I knew with this one-year timeline I'd be able to expose myself to a lot of problems that I hadn't seen before (given the smaller size of Clearbit), while also having a much greater amount of autonomy than I've had in the past. The most exciting part was that when I returned to school, I would know exactly what I needed to learn to become that much better of a marketer when I do graduate. 

Carpe Diem 

I read a post recently by Mark Andreessen, a prominent serial tech entrepreneur, that gave career advice to ambitious people. He states this about the idea of opportunity: 

They tend to present themselves when you're not expecting it -- and often when you are engaged in other activities that would seem to preclude you from pursuing them. And they come and go quickly -- if you don't jump all over an opportunity, someone else generally will and it will vanish.

I could have convinced myself that a similar opportunity would come up after graduation, and that taking a year off would simply put me behind in comparison to my peers. I could have also said that I was already in a good spot for employment, and a safer bet is just to enjoy my remaining years at university and take it easy. Instead, I decided to follow Andreessen's advice, and dive headfirst into an opportunity that could change the trajectory of my entire career. 

Conclusion + Acknowledgements 

I want to give a special shoutout to everyone that helped me make this decision, as is easily the hardest one I've had to make in my life. My parents and brother, for supporting yet another one of my crazy ideas, knowing that I (attempt to) do everything in my best interest. My friend & colleague Steeve Vakeeswaran, for finding this opportunity and helping me think through the decision. My mentors, Niles Lawrence and Jaxson Khan, who have always thrived on untraditional pathways, and reassure me that I can too. And also the handful of people who all recently had very similar experiences (you know who you are!), and act as some of the few references on this rocky road. 

I also want to give a shoutout to Huron University College, for being incredibly supportive in my decision, and helping me coordinate my deferral. Their liberal arts approach has also encouraged me to be critical of traditional pathways, while their tightly-knit community is a big reason why taking this opportunity was even a possibility.

Lastly, to Clearbit - I'm ecstatic to be given this opportunity, and I promise I'll make your risk worthwhile. 

Looking to follow me on this new journey? Subscribe to my email newsletter below to get updates on what I'm learning and recent pieces that I publish.