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

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

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

A quick timeline

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

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

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

Things I used to love — gaming, working out, even tech — started to lose value. I wasn't performing to the level I wanted to at work, and it wasn’t easy to find a strong friend group. To sum things up, it's a gut-wrenching feeling to have everything you always wanted and not be happy.

An inflection point

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

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

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

(1) Validation

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

(2) Scaling

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

(3) Customer Development

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

(4) Technical Acumen

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

Cali or bust?

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

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

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

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

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

Becoming a better marketer

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

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

The other area I improved significantly in was analytics. After starting in Sales back in 2016, I worked on the Rev Ops team at Shopify Plus, having to learn SQL, how to attribute marketing spend, and calculate sales performance. I was thrown into the deep end at Clearbit when I was tasked with developing a dashboard that reflected all these stats — except it hadn't really been done before. More than SQL (although those skills have improved), I learned the importance of diving into the logic behind analysis and dashboarding. Yes, I can explain the tables that I pulled from to calculate churn. But what is generating those numbers? Are tags firing correctly when someone signs up? Or should we revisit how we set up the tracking? Questions that are extremely important at a startup, and a general approach that is useful at all levels.

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

Managing life

While my professional development was great, the biggest win from this past year was my personal development. I took my support system for granted — being surrounded by people who think like me and support me through uncertainty.

The workplace is a very different environment. While my colleagues were very fun to be around, they were a little bit later in life, meaning discussions I was just beginning to think about (i.e. marriage, buying a house, etc.) were ones they've been having for the last decade. While this stalled me for a while, I eventually decided to take this problem of self-actualization by the horns.

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

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

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

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

Conclusion

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

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

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

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

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

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

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