Steve Ridout
Indie software creator

Back To Bootstrapping

April 5, 2022

After a few years of radio silence, I’m back! Back to tinkering around, bootstrapping my own software projects, and sharing my journey.

I had an amazing time at Duolingo over the past few years, worked on some awesome projects, and learnt a ton. While there I got to see the company grow from 70 to over 500 employees, from almost zero revenue to over $200M / year and a successful IPO last year. It was by far the best job I ever had and I miss my old colleagues there. It’s honestly hard to imagine a better company to work for. They are hiring by the way!

So why on earth did I leave such an awesome job?! It boiled down to this:

  1. I’m based in Madrid, Spain so I was working remotely. This worked very well, I had great working relationships over Zoom and via occasional in-person visits (at least pre-pandemic), but my network of tech-industry friends within Madrid had dwindled to almost nothing. Working remotely for a US company while also being a parent was not helping me to build connections with like minded friends where I actually live.
  2. I had the feeling that I’d achieved what I wanted to there*. Upon joining I mainly just wanted to prove to myself that I could hack it at a world-leading tech startup. While there I started a new feature called Stories which turned out to be pretty impactful. I like starting new projects and I could have continued doing that but Stories would have been hard to top. I felt I’d peaked.
  3. Duolingo IPO’d last year which removed the golden handcuffs. Basically I had stock options for which the tax burden of exercising was so large that it was impossible to do without being able to sell the stock.
  4. The chance to work on whatever I want without the pressure to make money holds one hell of an allure. It’s an amazing privileged position that I’ve dreamed of being in for many years, and now I can actually do it!

So now I’m planning to follow my curiosity, work on cool stuff, and share some of what I’m up to. Here’s a YouTube video in which I demo a new project I’ve been working on, please check it out!

* One slight caveat is that I didn’t develop Readlang much after selling it to Duolingo. I still think Readlang is great but it’s also niche and developing it further never felt like high enough ROI compared to other projects at Duolingo. It’s still running though, which I’m happy about!