Jan, 05 2020
2 Minutes

I’ve been thinking a lot about bootstrapping a software business.

Bootstrappers are alchemists. They produce a product people love, profits, and a lifestyle of freedom - all from seemingly thin air. How do they do it?

Alas, I haven’t figured that out. But I think I found the first step.


Successful entrepreneurs solve their own problems:

  • Shopify - Tobi wanted to sell snowboards online
  • Nomad List - Pieter wanted to find cheap travel destinations with good wifi, and good weather
  • Stripe - The Collison brothers (the elder two) had sold their last business and realized how difficult it was setting up online payments
  • Basecamp - Jason’s web consultancy couldn’t find a project management suite that stuck. Borne of frustration, they built their own.
  • Airbnb - Joe and Brian couldn’t make rent, but they had an extra airbed

In other words, they “scratch their own itch”.

You’ll find this advice everywhere on the Internet. So much so you might have grown numb to its wisdom.

I know I did. I saw it so many times, I began to confuse familiarity with understanding. I thought it meant:

  1. Find one of my problems
  2. See if others also have the problem
  3. Test if they’re willing to pay for it.

But that’s not what it means. All “scratch your itch” means is solve your own problem.

Full stop. Nothing else. Nothing about finding paying customers. Just scratch your own itch, and no more.


What?! That’s literally the opposite of everything I’ve read about market validation!


You see, something important needs to happen first - a change within your own mind. Instead of focusing on making money, you need to focus on making.

I was listening to an IndieHackers podcast between Courtland Allen and Arvid Kahl and they both talked about the importance of finding a good market. In the past, they worked on unsuccessful businesses and didn’t want to repeat their mistakes. And thus, it was important for them to start a business with the wind behind their backs.

It’s essential advice. But notice a key detail - they had failed at previous endeavors (Arvid around the 45:00 mark, Courtland mentions his past stumbles on the podcast all the time). They were already makers.


Previously, I conflated coding ability with being a maker. They are not the same. Working at a startup doesn’t make you one either. In fact, you can be a maker without knowing how to code. A maker is someone who lives this entire process: ideation, building, shipping, engaging passionate fans, and incorporating feedback. It’s an identity, a habit, not a skillset. And once you do all of that, something fascinating happens:

  1. You grow more empathetic. You get excited to show customers changes you’ve made. You await their response. When they point out a broken experience, you run back to your computer and fix it. And then you send it to them again. Maybe they’ll say thank you for solving something painful. When that happens, that’s the best reward. It’s why we do what we do.
  2. But perhaps the most amusing thing is you get “itchier”. The confidence you’ve built up from shipping will change how you see the world. You start seeing more solvable problems - you get more and better ideas. Which motivates you to build and ship. And when you do, you get itchier again. It's a virtuous cycle

Becoming “itchier” is key to the bootstrapper’s journey. It motivates you to build, ship, listen, learn, and grow. It helps you find better ideas. It helps you meet people. And all you need to do to kick off this incredible metamorphosis is to “scratch your own itch”.