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Guess It Until You Make It

First-time founders have one competitive advantage: they’re unsophisticated.


It has been 3 long months of me trying to get my second startup going, but my brain keeps pressing the brakes. Wait, this problem is not big enough. Wait, there are 17 ways that this idea can go wrong. Wait, we don’t understand the root cause yet. Wait, there’s so much competition. Wait, here’s a slightly better idea! Wait, let’s keep analyzing and learning and thinking and not doing anything.


3 months into my previous startup we were already building a product and signing on customers. Less analyzing, just taking it one fast step at a time. We did fail ultimately, but we were able to build a product, hire a team, sign customers, and raise money remarkably fast.


My second startup is going much more slowly. I’m doing a lot of sophisticated arguing with myself but nothing to create momentum and start changing the world.


Then I got this advice from my friend Yonatan Loewidt. He told me to stop analyzing and start guessing.

  • What is the biggest problem you want to solve? Make your best guess right now

  • How will you solve it? Make your best guess right now

  • How will you get users? Make your best guess right now

  • How will you make money? Make your best guess right now

  • How is it different from the competition? Make your best guess right now

  • What is the next step to make this happen? Make your best guess and do it right now

This advice was liberating. Guessing allows you to move right now. It creates something concrete that you can put in other people’s minds and start testing. It forms a holistic picture of your entire business. It removes your brain from the brake pedal.


Guessing feels both silly and scary to me. So I remind myself that:

  • Guessing is not random, it is following your intuition which is built upon your entire knowledge and experience

  • There’s no progress without movement. Pure learning and analysis are not movement

  • Ideas are iterative. Every guess is a stepping stone

Guessing does not imply less thinking. It’s thinking while moving instead of analyzing while standing.


How are you going to change the world? Make your best guess right now.

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