In October of last year, I was running engineering for a promising mobile commerce startup that I co-founded in 2011. By many Silicon Valley measures, we were doing well – seed funded, making revenue, ~20 person team, multiple launched products, etc. It was comfortable.
But one day I decided to abandon my startup, all because of one e-mail. This is that story.
The e-mail of note came from my girlfriend, and it set off a chain reaction of events that led to an abrupt series of personal relevations. It was an e-mail about a friend presenting a revolutionary technology at Google’s Solve for X (a showcase of change makers and moonshots). The e-mail itself was innocuous, but her rhetorical question is what struck me: “You could be there, presenting your world changing innovation. Why not?” That question left me sick to my stomach.
We met up later that night and talked about this. My immediate defensive reaction was to explain my 5 year plan, as I had rehearsed: “I’ll be at Solve for X soon enough. I just have to sell this mobile shopping company for $200M and then I can actually pursue my dream of solving the world’s water problems.” (This is, by the way, what Randy Komisar calls “the deferred life plan” – more on that later).
But my girlfriend challenged this: “How does selling a consumer app company help you disrupt the potable water market?” She was right, and I knew it.
It’s true – being a successful, proven entrepreneur helps your credibility. It helps you raise money, helps you build a team. But notice the verb I used: “help.” This was her point: sure, it’s nice if you have already shown you can return shareholder money (for her, selling her first company helped when she was starting her current company), but that’s far from required.
She went on: “If you have conviction and the right solution, you can get in front of anyone [to raise money, strike a partnership, build a team, etc], so what are you waiting for? You’ve already shown you can build a team and a product, you have the technical background to solve this problem. How does a liquidity event really make a big difference? Why continue being miserable?”
I went to bed that night with my head spinning. What was I doing?
The next morning in the shower, I had what alcoholics refer to as a “moment of clarity.” It all became clear – it was time to quit and go on my journey to solve the world’s water problems. I actually said out loud: “My name is Weston McBride, and I can do whatever I want to. I will approach this problem with enthusiasm unknown to mankind, and I feel sorry for anything that gets in my way.”
You see, for a while I had been living in what Tara Brach calls the “trance of fear.” Back in 2011, my first startup, an ed-tech startup, was doing OK, but we were running out of money, and I was afraid. I was afraid of failing – the cardinal sin of an entrepreneur.
So when I was approached by two successful (and famous) entrepreneurs to start this mobile commerce company together, I put aside my conviction for mission-driven startups and joined them. Why? The promise was a quick exit, the opportunity to make a name for myself, and to extend my runway with the liquidity event. I was afraid of failing, and this seemed like an easy and safe bet. I literally did the decision analysis to determine that this was the most likely path to a notable “TechCrunch” exit (just writing that makes me cringe) .
Any seasoned entrepreneur will tell you that if you want to make money, don’t start a company. You should start a company if you can’t sleep at night because there’s a problem you can’t stop thinking about. You should start a company if you’ve literally been brought to tears by talking to your customers. If you don’t have that level of empathy and commitment, why bother? How long do you expect to have energy to work on this problem?
Randy Komisar, who I mentioned earlier, writes extensively about this topic in The Monk and the Riddle.
“In Deferred Life Plan there will always be another prize to covet, another distraction, a new hunger to sate. You will forever come up short. Work hard, work passionately, but apply your most precious asset-time-to what is most meaningful to you. What are you willing to do for the rest of your life? That question would be absurd, given the inevitability of change. No, what the question really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you be able to say you’ve been doing what you truly care about today? What would you be willing to do for the rest of you life? What would it take to do it right now? “
On top of that, it’s exponentially harder to start a company that you’re not truly passionate about. I imagine it’s like marrying someone you’re not in love with.
There’s a reason why many investment bankers hate their lives. They do their work for the money (I know from experience – I spent six months as a banker and it is literally the main reason why most people are there). Doing work for money, especially when you have passions and interests in something bigger, is the most soul-sucking and demoralizing thing you can do. As Gary Vaynerchuck says in his phenomenal talk, “Do what you love, no excuses.”
Being stuck in this “trance of fear” meant that I couldn’t even identify the reason why I was so unhappy. I knew that I was powerfully unhappy, that something was wrong, but I was powerless to do anything about it.
It took a piercing question from my girlfriend to wake me from that trance. I knew I was working on a startup where I had no empathy for my users and had no passion for the space or the problems we were solving, and I knew that was wrong. But what I had to realize was that I didn’t need to do that.
That revelation liberated me. The next day, I talked with my co-founders and transitioned out of the company over the next 4 weeks.
Some people asked “What if the company gets bought? Don’t you feel like you’re giving up all that money?” The truth is, I wasn’t giving up anything – I was buying my life back.