City life

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

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

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

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

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

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

Physical factors 

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

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

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

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

Transportation 

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

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

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

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

Attitude

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

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

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

Conclusion 

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

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

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

Leaving mobile

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

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

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

The role of mobile

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

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

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

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

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

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

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

Trying something new

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

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

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

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

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

Staying motivated

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

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

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

Finding goals 

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

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

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

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

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

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

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

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

Motivation and over-achieving 

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

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

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

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

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

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

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

Conclusion 

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

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

How good are political party emails?

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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: 

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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. 

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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: 

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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) 

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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: 

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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. 

Frequency 

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. 

Conclusion 

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

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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 Tilt.com, 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. 

Conclusion

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. 

Conclusion 

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

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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). 

Conclusion 

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

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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. 

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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. 

Conclusion 

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

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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. 

Goals 

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. 

Conclusion 

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

   

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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. 

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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? 

Conclusion 

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

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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

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Second Email

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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. 

Conclusion 

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.

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#triggered - using intent in marketing campaigns

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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. 

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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. 

Conclusion 

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! 

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Intro to Digital Marketing

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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: 

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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.

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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. 

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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. 

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Marketing Data for Tech Companies

Tracking your user from lead to advocate. 

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For an early-stage startup, it's fairly common to create a set of buyer personas. The process normally evolves from making assumptions about what types of companies are the best fit for your product, and then talking with the sales team to validate said assumptions. While this is a good start, it's very temporary and hard to scale. 

Having worked with both large companies like Shopify Plus, and smaller startups like Turnstyle and #paid, I've seen the various models you can use to collect and work with marketing data, and the success these models have depending on company size and structure. In this article, I'm going to dive into the idea of marketing data and the role it should play in your company. 

Data from Day One

We all want to make data-driven decisions. There's an allure to throwing stats at your colleagues when proposing a product, refuting their weak, emotionally charged objections with cold, hard, data. The issue, however, with many startups is that their data set of customers and leads is simply not large enough to draw a logical conclusion on what works and what doesn't. This raises the challenge of when to make the jump from testing an idea to proposing an approach based on data. 

For example, most startups that specialize in the B2B space are going to be very sales-heavy in their early days. If you don't have a large customer base, budget, or inbound traffic, it may not make sense to invest in areas of marketing like content creation, lead nurturing, and retargeting. While I do address that notion in this article, it is worth noting the difference between collecting data and actioning data. 

A Strong Foundation 

I like to think about the relationship like hosting an event. Tickets for a conference will go on sale months before the actual date, and a number of the finer details will change based on registration. A smart planner might change a specific session focus if a large proportion of the attendees are from one industry. Notice that the focus of the event is unlikely to change, but data is being collected from day one. 

 Changing conference seating based on attendees can increase engagement. 

Changing conference seating based on attendees can increase engagement. 

Likewise, if you are running a small startup and have yet to develop consistency in your client base, it doesn't make sense to make decisions primarily driven by data. In most cases, doing so will result in skewed tests. For example, you might decide that India is the ideal market for your product, because 5 of your 10 inbound leads are from India, as is your only paying customer. This is simply untrue due to the small amount of data you're working with. 

What you can do, however, is begin to collect data. In this post interviewing Steve Huffman (Reddit) and Emmett Shear (Twitch), this point is driven home. Huffman notes: 

There are a lot of corners you can cut when you’re building your MVP, but lack of data can haunt you. Think very carefully about what the minimum viable data is. You don’t even have to look at it, just log it somewhere, so you have it when you need it.

This observation has strong parallels to marketing. When you have the data (and budget) to make decisions about paid advertising and SEO, there will be a sense of regret if you don't have data behind how your early users came to your site, and what search terms have been hitting your site the most over your product's tenure. 

Beyond Lead Generation 

Having credible marketing data can stretch into making good decisions about your product in other areas as well. Using tools like Segment to connect marketing data with user data can be very telling about your user experience. Some basic applications could include: 

User onboarding: is there a noticeable pattern among your trial users that come from certain marketing channels? It's possible that a larger percentage of your users captured through organic search are dropping off due to misconceptions around what your product does. The solution might be to revisit the funnel of those users, and see how you can optimize your landing pages and messaging to get users that stick, and nurture those that won't. 

Identify pain points: as a marketer, it is incredibly intriguing and useful to see the pages that a visitor has seen before converting into a lead (give their email). What can be even more intriguing is the pages visited by your customers. Are there certain pages that are frequented significantly more by your highly engaged users compared to users that drop off, or vice-versa? Do certain assets (i.e. industry reports) increase user activity if downloaded by customers? 

 Mode Analytics addresses user drop-off with their tutorials.

Mode Analytics addresses user drop-off with their tutorials.

Basic Marketing Data 

Even if it's clear that all types of companies should be collecting marketing data, where do you start? I divide it into a few different types below, with mediums you can use. 

Visitor Data: Use a free tool like Google Analytics to connect your site and start measuring your daily views, popular pages, and more. If you're feeling adventurous, you can set up a Goal and start tracking inbound conversions. 

Lead Data: Sales teams need to be meticulous with their efforts early on, to see what works and what doesn't. Use a free tool like Hubspot CRM to manage your outreach. They will get an idea of the industries, titles, and other categories leads are in, and which ones are successful. 

App Data: Most developers already have some function of storing user data, though programs like Keen IO make it a lot easier. If your developers already store their data in a warehouse like Redshift, you can use Mode Analytics to interact with it.

Conclusion 

This is only a general outline, and it will take you some time to decide on what stack works best for you. More than anything, it is crucial to decide early on that you will be collecting marketing data, and have it organize in some way. As long as you have a key (i.e. email) or other token that you can use to link your data together, it will be significantly easier to make data-driven decisions when the time comes. 

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The Basics of SEO (Part 2 of 2)

How to tweak your site to be optimized for SEO 

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I wrote an introductory post on SEO that gives you the raw basics on the idea behind SEO and how it works. Give that a read first! 

Before you go shedding thousands of dollars on optimizing your website for SEO, take a step back and re-evaluate your focus. I mentioned in my last post that (on average) search makes up 30% of your total traffic. While this is very impressive, there’s a belief that SEO will perform miracles for your site. That isn’t necessarily the case. 

In fact, without a strong foundation for your site, you’ll end up spending a lot of money on having an SEO agency build something that you could do yourself. In this post, I’ll dive into how you can think about SEO while building your site, and small tweaks that will make noticeable differences to your search engine traffic. 

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A Foundation for Organic Traffic   

When looking at SEO, it can be helpful to think about your site as a physical store. Someone passing in front of your store (homepage) may not have actual intent, compared to somebody that approaches a store rep (Contact Us page) or inspects a price tag. 

With that in mind, your website should be structured in a way that makes it easy for people who have intent to get what they want, and those who are unsure to find out more/be convinced. I’ve written about how to target people at different interest levels here. 

For a simple software company, this could mean having a visible “Contact Us” or “Free Demo” button on the homepage, while also displaying call-to-actions that quickly segment your visitors. A site that does this incredibly is Turnstyle. You can either “Try for Free” or “Learn More”, dividing visitors by intent immediately. 

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Optimize your Headings

I mentioned in my last post how to optimize your description in Search Engines like Google to get the best click-through for your site. The second challenge is keeping people on your site, and that starts with headings. 

There are three main types of headings: H1, H2, and H3. While a CMS platform like Wordpress will give you the ability to choose what type of heading your text is, they are easily identifiable by size/weight. H1 is the largest, followed by H2, then H3. 

Why does this matter? Imagine stumbling across a site through a Google Search. The first thing you’ll look for is the heading (probably the biggest one) to see if it’s relevant to your search. Hence, the rule of thumb is to have maximum (1) H1 and (1) H2 heading on your page. 

Your H1 heading should clearly connect to the purpose of the page. If your title is “10 Marketing Essentials”, your H1 heading/subtitle could be “What most small businesses miss”, and your H2 heading could be “Creating a Facebook Page”. The flow from title to content is smooth, and readers who are interested in that topic will be more likely to continue reading. 

The 🔑 Words

With site structure and headings out of the way, the final step is to optimize the actual content of your site for SEO. I mentioned in my last post about you don’t want multiple pages fighting against each other for the same keyword. This ties into how you should think about your actual site pages. 

If your site has a “Features” page, what keywords relate to your industry that you are trying to optimize for? A mattress company might look to target the words “improved sleep”, given that visitors who are looking for a mattress would favour that. 

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Likewise, mattress company Leesa.com has the words “better night’s sleep”, “cooler night’s sleep”, and “amazing sleep” all on their features page, with the first actually being included in a heading. This ensures that anyone who is looking for a mattress and stumbles across Leesa.com’s site through a search engine sees what they’re looking for right away. 

Not a Lone Wolf

I’ve mentioned before that SEO is not the miracle that will springboard your site into 10x visitor traffic. The reality is that SEO is simply a compliment to your existing efforts. Having more engaged visitors may not necessarily make an impact if you aren’t creating content that resonates with them, or placing call-to-actions (CTAs) that get them to complete your desired goal (i.e. signing up for a newsletter). 

Digital marketing is truly a cohesive game, and mastering only one part of the process can limit you as a versatile marketer. Pairing a mind for SEO with the ability to create relevant content can create a noticeable difference in how visitors interact with your site. I’ve written about how you can create content that sticks here. 

Conclusion

If you’re a growing business that seriously wants to improve their SEO, then it might be worthwhile to seek some professional help. However if you’re a small business or simply want to have your site’s search traffic scale with its popularity, then following these tips are surefire ways to improve your ranking and visitor engagement. 

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The Basics of SEO (Part 1 of 2)

Unpacking one of the most popular terms in marketing

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As a marketer, I can identify with always wanting to tackle the most exciting and impactful project for a company. So I can easily say that I would rather be developing the launch strategy for a new product feature than combing through a website to optimize it for SEO. 

With this being said, I know that SEO is a key skill to learn as a marketer. On average, search traffic makes up 30.5% of total traffic for small businesses. Therefore it’s key that a business make an effort to integrate the idea of SEO in their content strategy. 

What is SEO? 

I won’t pretend to be an expert on the subject, so here’s an excerpt from Moz.com on what it is: 

"Search engine optimization (SEO) is the practice of increasing the quantity and quality of traffic to your website through organic search engine results"

There are two factors here that are important to note: quantity and quality. The former is self-explanatory, and simply means driving more traffic to your site overall. The latter, however, is something to explore deeper. 

Visitors coming to your site via a search engine are very different from ones that are referred via, for example, paid ads. Search visitors often have a specific idea of what they’re looking for, unlike paid visitors who may simply be interested in the idea of your site. 

You will notice, with a site that is poorly optimized for SEO, that visitors coming through search might have a high bounce rate (leave on the first page), for one of two reasons: 

  1. The site’s description in the Search Engine was not coherent with what was posted on the page 
  2. The quality of the content on the site is not strong enough to captivate them to stay on the site

Let’s jump into the most basic and popular idea behind SEO to understand how to address these two problems. 

Optimizing for Keywords 

When you type an entry into a search engine like Google, an algorithm searches their database to find sites that align the most with your query. On a basic level, this means looking at factors like:

  • Number of keywords
  • Word count of the page
  • Number of credible links back to the site
  • Total site traffic

At first glance, the idea might be to flood every page on your site with keywords that you want to attract visitors from, in order to maximize the chance that your site is seen. The obvious issue is that Google’s algorithm will pick up on this and penalize you for it, but the more crucial point is the idea of page competition. 

If all of your pages optimize for the keyword “Fidget Spinners”, then all of your pages are competing against each other for the highest page rank. It also means that someone searching for “Fidget Spinners” could be clicking on a different page each time they search, which dilutes your page traffic and makes it harder to improve your site rank. 

This means that you need to think carefully about how your site is structured, and what each page is designed for. For a software company, this often means having certain pages that emphasize certain product features, while others may aim for larger keywords related to the industry. 

Search Engine Appearance 

Even with a strong page that is relevant to the user’s search, the next big challenge is actually getting the user to click on your listing. Wordpress, among other CMS platforms, allows you to edit how your page will show up in a search engine like Google. This includes changing the title, content, and relevant tags. 

The automatically populated description and title is often long and/or simply an excerpt from the page itself, which probably does a poor job of reflecting why someone should click on the link. Using the fidget spinners example, compare a few of the results below:

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The first result has a lengthy title, but the description is succinct and conveys to the user immediately what the page will entail. The second result has a more legible title, especially with the use of the ‘|’ character. One can only assume that gearbest.com has more site traffic than addictivefidgettoys.com, and hence gained a better ranking. 

Seeing Walmart fall below both of these results was surprising, but only reconfirms the strength of Google’s algorithm, and importance of SEO. Being a corporate giant with millions of products, Walmart definitely did not optimize this page for a specific keyword, however their site traffic and overall usability (seeing price and rating in the result) garnered them a top spot. 

The Long Game 

On average, SEO efforts can take 6 months or more before you start to see results. The reason being that Google doesn’t consistently crawl your site, and hence won’t pick up on your changes and improved credibility right away. 

I will go into more depth in Part II about how you can alter each of your pages to improve its SEO, and a few other basics about keywords optimization. 

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Content is like Cheese

Why your content should get better with age, not decay

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I have a lot of hobbies, and recently I’ve taken an interest in cheese. As odd as it might sound, the idea of food getting better with age is almost counterintuitive. In the right environment, a mediocre cheese will age to perfection, while in other conditions it might become moldy and undesirable.

Content creation is, in many ways, very similar to cheese. Fresh content is attractive, and can go viral in a short period of time. Older content can become stale, either by losing its relevance or by getting lost in the fray. Like cheese, however, handling older content correctly can enable it to make a huge impact on your marketing efforts including improving your SEO, time spent on site, and overall visitor experience.

The idea of considering both fresh and older content in your marketing efforts falls into the idea of marketing segments: acquisition, inbound, and evergreen.

Acquisition Marketing

Probably the most popular amongst the three, this type of marketing refers to pieces that aim to attract users to your site, simply put. The content is most likely easy to share, and hence has the ability to go viral on social platforms.

Example: “The Dark Side of Entrepreneurship”

Body: Dives into the lows of entrepreneurship including failure and burnout. Little focus on the product but drives a lot of traffic.

Inbound Marketing

There will be a portion of your visitors that visit your site organically, either through a search result or via another referring site. These visitors are typically more engaged as they have a specific idea of what they’re looking for in your content. The content is likely more in-depth, and geared towards those that aren’t already familiar with your product.

Example: “E-Commerce Blueprint: Starting an Online Store”

Body: Breaks down the steps to validating an e-commerce business, and how to do it on Shopify. The call-to-action is signing up for a free trial.

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Evergreen Marketing

After creating content for a while, you will have developed a dedicated following, either through consistent visitors or potentially through an email newsletter. These users are evidently familiar with your product and content, but their engagement will decrease over time. For a business, their customers or cold leads typically fall into this category. The content, therefore, is designed to re-engage users by bridging the gap between your product and their interests.

EXAMPLE: “How 2 Chainz Used Shopify to Make $2m in 30 Days”

Body: Highlights how 2 Chainz became successful on the platform, and touches on the functionality and use of the product. Could be sent to customer/user segments depending on their engagement.

Building a Content Strategy

Like a cheese platter, you need to understand how your content pieces fit together, and how that defines your content strategy. Simply attempting to write viral pieces will lead to a lack of cohesion in your content, and probably be reflected through a high bounce rate (users leaving your site on that page) along with a low time spent on site. As a business, it also makes it challenging to get users to convert to buying your product, as they all have low engagement.

Once you have written a few pieces of content, check your stats and see how each piece is performing, and what their focus is. I.e. if you are a food blogger, and your first few pieces are on restaurant reviews, it’s possible that a piece on Mexican food performs especially well. You could focus your next few pieces of content on more Mexican restaurants, then create a “Top 5” post that is easily sharable, and links back to your other pieces of content.

The “Top 5” post will get a high amount of traffic, and a number of users will follow the backlinks in your post to other pieces of content about Mexican food on your site. This increases their engagement, and increases the possibility of them reaching your conversion goal, i.e. signing up for a newsletter.

Good for Business

I’ve already gone over an example of how personal bloggers can incorporate this strategy, but let’s take a look at another use case, this being for businesses.

Start by reviewing the content you’ve already published, and categorize it based on how it relates to your product. I.e. a restaurant marketing software company might categorize its content into segments such as “Case Studies”, “Industry Information”, and “Product Features”.

Once you understand the basic focus of each of your pieces of content, try to further group them based on their role in your customer funnel. I.e. an industry report might be top of funnel content, meant to attract leads by giving them insights on the industry while collecting email addresses. Case studies on the other hand may be grouped as bottom of funnel content, meant to be used when leads are already in a conversion with a sales rep and need to be nurtured to speed up the sales cycle. I write more about email nurture campaigns in sales in this post.

The next step is very similar to that of a personal blogger, where you review the performance of these posts. If you haven’t already, you should set up goals in Google Analytics to see how well each of your posts convert. Looking at both how your content fits into your customer funnel and how well each of them is converting will give you direction on what to focus on creating. I’ve added a photo below of how content works in relation to a customer funnel for a typical business-to-business (B2B) Software as a Service (SaaS) company.

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For example, if you have a lot of case studies that convert poorly, it might be a good idea to syndicate them, add some additional information on the industry, and create an e-book on how companies can adapt to the changing dynamics of the industry to stay competitive. This may become an amazing source for new leads opposed to being part of nurture campaign, and isn’t hard to do since you already have the posts created.

Conclusion

Crafting a content strategy that values and incorporates both fresh and older content is a sure-fire way to increase user engagement. Though it may take some time to see the results of your efforts, investing the time now will ensure your site and product reflects a cohesive brand and reduce the volatility of your customer funnel.

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