Bootstrapped

When you run your own little software company, be it a SaaS or old school downloadable software, and you've been doing it for several years, and you've got through the major initial challenges that were interesting and fun and rewarding to conquer in the first few years, and you've now got to that point where your product revenue is stable, and your product is pretty much feature complete, it becomes boring.

Here's 3 projects I've been working on to alleviate my bootstrapper boredom, while not putting my company in peril.

Mentioned in this episode:

* My coaching: https://steveofmcleod.com/
* My book-in-progress: https://killthehippo.com/
* My public speaking, as recorded at Business of Software Europe in April 2025: https://businessofsoftware.org/playlists/playlist-europe-2025/#SM

Show Notes

When you run your own little software company, be it a SaaS or old school downloadable software, and you've been doing it for several years, and you've got through the major initial challenges that were interesting and fun and rewarding to conquer in the first few years, and you've now got to that point where your product revenue is stable, and your product is pretty much feature complete, it becomes boring.
Here's 3 projects I've been working on to alleviate my bootstrapper boredom, while not putting my company in peril.
Mentioned in this episode:
 

Creators and Guests

Host
Steve McLeod
Founder of Feature Upvote

What is Bootstrapped?

This is the archive of Bootstrapped.fm. A seminal Bootstrapper-oriented podcast started in 2013 by Ian Landsman and Andrey Butov. The first iteration ran for 104 episodes. In 2019, Steve McLeod took over for another 139 episodes. We've set this podcast to release order so you can experience it as it was initially presented.