How I Reached My Escape Velocity

It’s been 10 years, 3 years, 2 years, and 5 years since I started investing in early-stage companies. It went fast and it went slow. Surfing the sea of start-up anonymity, assembling a team that developed each other into who we needed to become, worrying about making payroll, bootstrapping, fundraising, negotiating, joining/navigating/changing a big company. And advising other entrepreneurs on the same. It’s a blur full of gems I’ll never forget. I’m on a flight back from Dublin. I took a stroll around the start-up pavilion. Literally thousands of start-ups have a 3 foot long space to engage anyone willing to hear their pitch. I felt the energy and the pain. You’re putting everything on the line. Your business becomes intertwined with identity and self-esteem. Nothing is more humbling than everyone passing by your future. Anonymity is both a blessing and a bitch. Nobody cares. Breaking through anonymity is a game of endurance and optimization. Enduring mistakes and optimizing via postmortems. Enduring sleepless nights to process the solutions. The journey of entrepreneurship is one of “relative joy.” Rational thinking keeps us where we’ve already been. The greatest products I see are made in irrational ways. AirBnB was at the edge of reason. Investors must work at the edge of reason. The worst investors and entrepreneurs are the most rational and reasonable. Groups make us too rational. You shouldn’t want or need consensus. Don’t require it to proceed. Respect is incredibly productive. Work with an eclectic mix of all-stars that have conviction at the edge of reason. If you avoid folks that are polarizing, you avoid bold outcomes. You must tolerate some necessary ruckus. Great creative minds have their demons. Conflict is an ingredient. It’s part of the package. Engineers ahead of their time are intolerant of engineers behind the times. Being aggressive is a feature, not a bug. A strong culture tolerates some necessary ruckus. Shaking things up keeps things going. Creating something from nothing is a contact sport. It’s messy for a reason. Feeling entitled is always a losing strategy. There’s no bigger red flag than an entrepreneur that feels entitled. You stop hustling. Others resent you. One suddenly feels that a lot of work is “beneath” him or her. Feeling entitled is always a losing strategy. You stop winning once you believe you deserved what can only be the result of good luck. Don’t feed greed. This is a simple but important lesson. People are never satisfied. I respect investors that get what they deserve. You always should. But some people aspire for an endless share. Beware of people that will feed themselves extra at the expense of others getting what they deserve. People are toxic. Most leaders are pleasers. I love keeping people happy. But you can’t feed greed. The science of business is the things that scale. The art of business is the things that don’t. Art is special because it doesn’t scale. Art inspires us in inexplicable ways. It is real, unique, and personal. These same forces make a business special. They don’t teach them in business school. They defy conventional wisdom. Why would a fast-growing food chain engage local artisans for each store they open (sweetgreen)? Why does a massive tech company deliver kittens (Uber)? Why does a guy with millions of followers take time to personally respond? One by one, each action is “unnecessary” and quantitatively immaterial. It is all that distinguishes you from being a commodity. Gestures build relationships between people and entities. Design is the little things that make a big difference. Great entrepreneurs are designers. They compete with the art of business — the stuff that doesn’t intuitively scale. Don’t optimize the art out of your business.

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