Be The Fool Who Tries


To create extraordinary in your life, perfection is not required, but a degree of foolishness is. When I cofounded the company that became, I was only 24, so I certainly didn’t have it all figured out. Though, ironically, like most people at this stage of their lives, I thought I did. I was all energy and confidence. I look back and attribute much of my early success to being naïve—too foolish to realize that I had no business dreaming so big and actually succeeding at what I was doing.

I still very vividly remember the moment this dawned on me. When I was in business school, about to drop out to start a company, my co founder, Jenny Lefcourt, and I reached out for advice before fundraising meetings. Jenny called on her old boss and serial entrepreneur that I’ll call John.

John met us in the Stanford Business School cafeteria, which at the time was a windowless basement (nothing like the resort it looks like today!), and we offered him a rice bowl in exchange for an hour of his “been-there-done-that” wisdom. We got the better end of that bargain! We sat down and shared our pitch for an online single stop wedding gift registrybringing together all the titans of retail and content, in one spot on the Information Superhighway. We were pretty impressed with ourselves. The customer value was clear, and better yet, the proof was all right there in our excel model. This was going to be huge! What was his advice on negotiating the best terms with Venture Capitalists for our seed round?

A very amused and cool John sat across from us, leaned back and said “Wow. I really envy you…. Because you are SO naïve….”

This was one of those moments when you’re thinking, “Was that a compliment?” Because, “thank you” is not rolling off the tongue.

John then went on to say, “I admire your inexperience. You look at things for the first time and you see this easy path. You just see one wall ahead of you and you think, ok, I can climb over this wall. I get funding. Done. I can declare victory. But I have been down this path before, so I know that wall is much higher than you think, and instead of looking straight ahead at that one wall, I see it from above and I know that right after that wall, there is another one, and it’s just as high, and then another, and another and another. It looks so daunting to me- I’m too tired to start climbing!”

I stayed silent just a second longer, and then with great sincerity, I quietly said “Thank you!” knowing in that very moment I learned more then I had in any classroom on that campus; right there and then I made a pact with myself to never let life and experience take away my energy and optimism. I vowed to myself I would rather stay a bit of a naive fool than someone too tired to try.

In fact, with the right entrepreneurial spirit, you can gain enough wisdom to see you have more choices than to just use brute force to climb over every single one of those many, many walls. If you ask for it, and you’re the kind of person that will return the favor, you’ll find people to give you a boost. And, sometimes, if you look carefully, there is a door. You can just open it and walk through.

Holding onto your optimism, while cultivating your wisdom, is an art you can master. We want to think that the road to success is paved with golden bricks, but even Dorothy and the gang encountered creepy flying monkeys along their path to Oz. You will always encounter challenges and setbacks on your journey. But the bold remain steadfastly optimistic and always on the lookout for that hidden doorway -- because if think of any road less travelled as too daunting, you never even begin the journey to an extraordinary destination. 

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