The AirbnUber Strategy

Supported by Greenhaven Road Capital, finding value off the beaten path.

Inspiration: The Upstarts by Brad Stone

For hopeful entrepreneurs, a roadmap can be a godsend. Adam Carolla puts it this way:

Learning from others is a great way to skip mistakes or at the very least, prepare for them. Let’s see what Brian Chesky did at Airbnb and Travis Kalanick did at Uber. Ready?

1/ Be bright yourself. Chesky attended the Rhode Island School of Design. Kalanick earned a perfect score on the math portion of the SAT. We’ll get to the luck and other factors in a moment but we should at least acknowledge that both men had certain capabilities.

2/ Get/be someone who writes code. Chesky teamed up with someone else and Kalanick adopted the Uber project after it had already been started. For all their abilities in point one, we immediately see that they didn’t write the “Hello World!” code. That’s not to say they couldn’t, only that even successful founders need help from other people. This also is apparent in the advice to ‘hire people smarter than you’ or ‘hire for your weaknesses.’

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3/ Build something. Your first thing won’t be THE thing, but you can’t iterate ex nihilo. Uber went from UberCab to UberX, a monumental shift in the short history of the company. Airbnb’s early site was built on a simple WordPress theme. What each group of founders did was just start. Then you can…

4/ Talk to customers and make changes. The famous story that comes from this period was when Paul Graham told Chesky he needed to get to New York and help the owners take better pictures of their apartments. Do things that don’t scale. Uber too would do this, handing out phones to drivers to test the app. Gentlemen and women in Silicon Valley call this a ‘pivot.’  Marc Andreessen (naturally) put it more colorfully; “When I was a founder, we didn’t have the word pivot. We didn’t have a fancy word for it. We just called it a fuck up.”

5/ Be lawful but not angelic. Neither Chesky or Kalanick toed the line. Chesky pursued a mission he felt was superior to the laws. Kalanick just thought he was right. That’s the point of entrepreneurship. It’s the idea that you can do better. Yvon Chouinard said to study the juvenile delinquent if you want to understand the entrepreneur.

6/ Practice your apologies. At some point, your company will make a big mistake. Follow the advice of Scott Galloway and do these three things. Acknowledge that it happened, take full ownership for the situation, and over correct. Lawyers and public relations experts can help with the words but their fingerprints shouldn’t show.

7/ How to disrupt lives. A change means someone loses and someone gains. Founders who want to #disrupteverything create this transaction. Taxi drivers expected a closed ecosystem with valuable assets (medallions) and limited competition. Drivers of the black cabs of London studied “The Knowledge” to earn their license and chance for a middle-class income. Disruption changes both sides of the ledger, suppliers and consumers.

8/ Elbow grease. Even though both companies eventually found replicable systems for entering new markets at first it was a lot of legwork and elbow grease. There were trips to lawmakers, ‘workcations’ (Uber), and long hours. Technology appears to be a silver bullet solution but as Ben Horowitz notes, most problems require a lead bullet approach.

9/ Once you have a bearing, accelerate to escape velocity. When I did a triathlon, the swim portion was in a large circle. Every so often I paused to reorient myself before swimming again. Startups should do this too. When asked for advice Chesky tells founders to stay off the radar as long as possible but then grow as fast as they can.

Caveat emptor: During the early days of Stripe Patrick Collison wasn’t sure he should be working on Stripe. The early days of Facebook was the same story. The roadmaps for successful and unsuccessful startups are indistinguishable in the beginning. That means you can do all these things and not be a Silicon Valley unicorn. There’s one more thing you need; luck.

Laird Hamilton said, “We’re all equal before a wave.” Stone’s books cover is a wave. Founders can do everything right but they have to get lucky too.

Thanks for reading. If you liked this post you can read more good stuff like it at Mike’s Notes, a monthly paid newsletter.

10 thoughts on “The AirbnUber Strategy”

  1. […] Brian Chesky found this out when starting Airbnb. His advice to future entrepreneurs was to fly as low as possible for as long as possible but once you were discovered to grow as fast as possible. One possible path is to have a Disruptive Innovation as Clayton Christensen defines it. […]


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