There is no plan strong enough to survive a collision with reality
One of the most fascinating parts about my job is that I get to speak with so many successful (often very successful) entrepreneurs about their journey. Each story is very unique and you can't help but marvel at how things turned out the way they did. That's because the most common pattern I've recognized in all of my conversations is that the path to success not only isn't straight, it sometimes takes a complete nosedive off a cliff followed by 3 or 4 times of falling on your face before eventually clawing your way to success. In fact much of the time their CV essentially reads as "founded 3 total flops followed by a unicorn". It really is that stark much of the time and there's a very good reason for it.
This is a concept I love to bring up whenever I give a talk about building entrepreneurial communities. VC's have a very unique perspective on failure in that their entire business model is trying to play the odds to overcome it. They realize that 90% of their bets are likely going to fail and of those that don't, the top performing portfolio company is likely to outperform every other company they've invested in combined.
A founder on the other hand only experiences one company at a time. As a result they see failure as overcoming the odds, not playing them, and that's the problem. Founders that try to "overcome the odds" end up putting their head down and trying to ram their idea into the market irrespective of the data they're receiving from customers. To them the only way forward is forward. They have a plan and their sticking with it. That's a loosing recipe. As Chuck likes to say "There is no plan strong enough to survive a collision with reality."
Let's be honest for a second, the ultimate success of a business cannot be attributed 100% to someone's grit, determination, or intellect for that matter. Back in October of 2018 we were lucky enough in Upstate NY to host Marc Randolph, the co-founder and original CEO of Netflix, as the keynote speaker for Upstate Venture Connect's annual conference. In his address he echoed this exact same idea: "I was involved in starting 7 different companies (including Netflix). 2 of the companies have billion dollar + market caps, 3 of them have had IPOs, 2 of them went completely out of business, and 1 was a mediocre business. But if you had asked me on day 1 which would be which I guarantee I never could have told you and neither could anybody else."
Persistence is a necessary but not sufficient factor for success. If in retrospect an entrepreneur is claiming they never would have correctly guessed which of their ventures would ultimately lead them to success then it's impossible not to assume chance and circumstance played some role in the outcome. The point is that successful entrepreneurs embrace those odds and play them in their favor. They make up for the high failure rate by taking as many swings at bat as they can and learning from each experience.
My perspective is therefore to tell entrepreneurs to play the same game investors do. Don't think about any one idea as being the defining idea of your career. Test lots of ideas, run many experiments, expect most of your ideas to fall flat on their face. And don't just think, do! Finding that successful idea that sticks is not a matter of persistence to overcome the odds its a matter of persistence to play the odds. Test, experiment, try, fail, iterate, and try again. Entrepreneurial success is about having a passion for the hunt not for the end game. When the market response to a test is stronger than you anticipate it, that's the moment you start to double down and discard the rest.
Why do I find this such an important topic to bring up, even to experienced and successful entrepreneurs? Because oddly enough I find that the more stuff you know the more you realize how much stuff you still don't know. If life hasn't dealt you that punch to the face just yet it's an incredibly humbling and exciting experience when it does. Even the most experienced among us need to be pulled out of the weeds once in a while and be reminded that entrepreneurship is and iterative process not a planned outcome.
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