The 6 Tradeoffs Founders Have To Make

And a story about working at Uber and Airbnb

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If there’s one thing all founders can agree on it’s that you can never have it all.

Maybe one day after you’ve IPO’d, retired, and spend half the year traveling the world on your mega-yacht it’ll be a different story.

But being a founder inherently means making tradeoffs every day and the earlier your startup is the more you need to make.

Even if partners, investors, employees, and customers all asking for different things it’s up to you to guide the ship in the right direction and make hard decisions.

This week I’m highlighting 6 tradeoffs that all founders need to make 👇

6 Tradeoffs Founders Make


I built products at both Uber and Airbnb. At Uber every team member had tons of autonomy — the person closest to the problem was the one who was trusted to find the best solution for it. At Airbnb all strategy and direction was handed down from above — the person with the broadest context was trusted to solve the problem and individual team members were just there to execute.

As an employee I enjoyed my time at Uber a lot more but as a founder I understand why Airbnb was built the way it was.

Both are excellent companies in their own ways. But one big difference was that you could always find people in the Uber office late at night, working hard. At Airbnb we had lots of meetings and people left on time.

As a founder it can be hard to give up any control. Your company will make more mistakes if you do. But allowing those mistakes to happen creates more buy-in from your team. They’ll work harder to prove themselves.


When you’re a startup you have unlimited opportunity — you could build anything!

But you also have incredibly limited resources. Often you have no money. You’re on the Soylent and ramen diet. You’re sleeping under the stairs.

Startups need flexibility to adapt, survive, and pursue new opportunities — sometimes rapidly. But they also need focus to avoid getting lost in a sea of half-done ideas.

The more you focus on a single thing, the more you may have blinders on and miss a big breakthrough, or a connection to someone who ends up mentoring you and helping you meet investors. It can be tough to say no to happy hours or new product ideas for this reason.

But on the other hand, a lack of focus means you never make enough progress to reach conviction about whether something is useful or not.

A good tactic is to run time-boxed sprints against specific ideas. Give yourself 1 month to reach conviction one way or the other. Pursue whatever gets you closer to that. If you don’t hit it in a month, move on — you’ve had long enough.


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