From entrepreneur to a Big Co PM

Last July, I made the decision to join Facebook after 10 years of running my own businesses. (But not without some good time off first, my official start date was in January this year)

Now, many entrepreneurs reluctantly join Big Cos after their company is acquired and then count down the days of their gold and handcuffs before starting their next venture. And then here I was after selling all my business interests in Toronto just volunteering to join one…

Here’s what made me take the leap:

  1. It was time for a change.
    Ten years heads down focused on a business is a long time. It consumed my entire 20s and although I was very happy with the outcome, the long haul affected me physically and mentally. I knew I needed to start investing in myself and that that investment needed to start with some big changes.
  2. I always dreamed of living and working in SV.
    Every 6 months or so an article pops up trying to combat the Canadian brain drain by comparing the progress in Toronto/Waterloo’s innovation sector to SV to help motivate talent to consider joining and building companies north of the border. While the progress has been stellar, the reality is SV is truly a place unlike any other. The ideas, talent, diverse climates, access to capital and financial opportunities are second to none. It is the collection of all of those things that make this place unique. I wanted to experience it first hand and one day bring these learnings back to the city that raised me.
  3. I wanted to grow.
    I’ve always tried to hire ‘above my weight’ as a founder and kept really strong mentors around me. These incredible people taught me a lot by sharing their approaches, frameworks, perspectives, etc. For this I’m eternally grateful. The problem was I found myself spending majority of my time “running a business” — the operations, sales, finance, legal and HR. These became great growth opportunities, however the bigger the business grew, I got further away from the actual products we were building. As someone who obsesses over product design and product growth — it was important for me to get back to what makes me happy and at Facebook I could operate on a much larger scale (more data, more people, bigger problems) and work closely with some of the best product minds in the world.

One year in it is now safe to say, I’m really glad I embarked on this adventure. Although some of these may seem pretty obvious, I wanted to share some of the learnings and highlights I’ve had over the last year:

At work:

  1. What bottoms up really looks like.
    Authority is not something you hear about or see frequently at FB. This was the biggest learning curve for me personally when joining. I kept thinking, “but how do decisions get made?”. In short, they aren’t kidding when they say “data wins all arguments”. Decisions get made by asking good questions, by figuring out how to quickly answer those questions (analysis, experiments, etc) and then letting those answers lead you to decisions. The better the questions and the better the answers, the more obvious what to do next. As simple as this sounds, this can be applied to everything from operations to product development. Even when I’m extremely sure that the direction I want to head is right, by going through this process everyone around will also be confident in the direction and this pays dividends when executing.
  2. Earning your spot rather than proving your worth.
    My time at Facebook really illuminated to me what it feels like to be hired. It’s something so simple, but as a business owner I never got the opportunity to really experience it outside of some odd jobs as a teenager. At my prev. co we relied on the staples of good hiring — strong hiring managers, recruiters, well-designed orientations and good resources. There is a cultural part to hiring though. The culture when someone was hired was usually- let’s see if they can earn their keep. The onus was on the new hire to prove themselves. It was almost as if we thought they wouldn’t and speaking to several old employees — it was a very stressful and challenging first several months until they got in their groove. My experience at Facebook so far has been very different. My first few weeks at work wasn’t stressful at all. Everyone I met was so happy I joined. They were excited to learn from me and to get my feedback. I believe this is because all of us know how selective Facebook is and how difficult the interview process can be. If you made it through, the general feeling is you must be great and therefore you’ve already earned your keep. It’s a nice warm start to help you quickly get adjusted so you can hit the ground running.

In life:

  1. If you aren’t healthy, don’t expect your career or relationships to be either.
    As an entrepreneur I underinvested in my health. I drank a lot, stayed up late and rarely exercised. This affected everything from my energy levels to the clarity of my thoughts. After a year of consistent exercise, predictable eating patterns and dedicated time for leisure and self-reflection — I just feel better. I don’t work 60+ hours a week anymore, but I feel like I’m just as productive. There was a time when I could barely get out of bed at 8am. Now I wake up everyday before 6am energized.
  2. Don’t rush.
    I’ve always felt like I’ve been in a rush. In a rush to grow up, to grow the business and to be successful. I focused so much on this that I forgot to really enjoy life. At one point life just got too serious. My mood, for example, would be directly connected to the success of the business. It impacted how I treated my family, friends, co-workers and myself. In hindsight, I wish I just slowed down to really enjoy the moment and invest more in the relationships around me. I’m going to try and make sure the next 10 years don’t disappear as quickly.

Now of course, you don’t need to join a big company to experience any of this. The big company job by design just offered the stability to help me discover the importance of these things. I do feel that with these learnings under my belt now building my next company won’t have to take as big of a toll on myself or the people around me. But until then I look forward to continuing my journey as a student within Facebook.

So long 2016.

Written by

CEO/Co-Founder at Converting passion into everyday life.

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