This week, I spoke at the capstone event for Startup Canada in Vancouver, which was a cross-country tour helping local startups get ready for the major leagues. The organizers did it big — 400 people at the new Waterfront Convention Center built for the 2010 Olympics.
They also did things a little differently; rather than have people come up and pitch their companies, 20 founders were chosen to share personal stories about the time in their life when they *knew* they were going to be an entrepreneur (including one person I’d mentored at Startup Weekend Alexandria last year who’s now raised money and moved to Canada). My most favorite came from a guy who shared his painful journey battling a life-crippling addiction to… pay-checks.
In my keynote, I decided to share a few AHA moments of my own. Here’s a short summary:
1. When I realized I was going to be an entrepreneur: June 14th, 2000. I’ll never forget this day. In the middle of writing my Senior Year final exams, my friend and I sold our web-hosting business, and I gained the confidence to join the world on my own terms. All my life up to that moment, everyone around me, my parents, my family, my teachers, my counsellors, etc. was telling me what to do with my life. They all had an opinion (expressed more lovingly by some (ie. my folks) than others (you know who you are! :-)). For me, taking a small idea from a hobby and growing it into a real business serving tens of thousands of customers was all that mattered at the time. I was having the time of my life making something out of nothing. I count myself really lucky because it was the sale of the business that made it possible to defer college and take entrepreneurship seriously (if we’d failed, my life would have taken a very different direction, one that may not have pushed me as hard).
2. When I realized I wasn’t the smartest person in the room. The easy part was getting into business school. The hard part was surviving (and then thriving). All my life I had been at the top of my class (whether it was the G&T program in seventh grade or the IB program in high-school), but all of a sudden, I found myself struggling not to finish last in every assignment from Operations to Management Science (the hardest set of classes I’ve ever taken). The only way out of it was asking for help. Something I’d never done before. Asking for help = something in my mind that most closely resembled failure. Running out of options and excuses, I admitted I just didn’t get the material (to a small group at first, and then more openly with professors).
Surprisingly, I wasn’t chastised (well, a little), and the real pain came in all the extra homework and readings, which cut heavily into my sleep (but thankfully not the partying). With a little bit of luck, and A LOT of help, I graduated with an A- average. In the end, I learned that the only way to get help is to be vulnerable (not something that entrepreneurs like to do! See my quote in Forbes).
3. When I realized the best days are ahead. Starting a company in Silicon Valley was a dream I’d chased since I was a teenager. After bschool, I moved down to Palo Alto to find three things: an idea, some money, and a co-founder. It took me nine months, and we were off building Involver. In a few years, the team grew from 7 to 70, which meant I had fresh college grades who were senior executives, including a guy with a beard running around the office with a blanket (he recently defended this dress by reminding me how cold it was in the building: B-Y-O-Blanket right?).
All of a sudden I had an organization to manage: lots of people with different personalities (sometimes conflicting) and priorities and wants and needs. As a leader, I knew we had to operate at breakneck speed, but I was over-analyzing. Everytime I made a decision, I’d go back and revisit it. I would replay situations over and over like a movie, and make mental notes of all the things that went wrong, and what I could do better next time. I was destroying myself.
Then one day, I read a blog post by Ben Horowitz where he talked about why it’s so hard to be CEO:
1) “Everybody learns to be a CEO by being a CEO.” There is no school for this stuff.
2) “Focus on where you are going rather than on what you hope to avoid. When they train racecar drivers, one of the first lessons is when you are going around a curve at 200 MPH, do not focus on the wall; focus on the road. If you focus on the wall, you will drive right into it. If you focus on the road, you will follow the road.”
Once I realized that entrepreneurship is a marathon not a sprint, life got much better. I began to focus on the next meeting not the previous one. Nowadays, I don’t worry about making mistakes; I focus only on doing the very best job I can at this very moment.
Startup Canada was amazing. Thank you to all the people who shared their tweets and emails. And thank you to the volunteers, BCIC, and everyone else that made this tour possible.