Geoff Roberts — Playing the Long Game — The Bootstrapped Founder 331


Dear founder,

Geoff Roberts (@GeoffTRoberts) is the co-founder of Outseta, and he's halfway there, 7 years in. Outseta —the SaaS starter kit and the business behind it— is built and operated on a multi-decade timeline, and it's not been easy to achieve profitability.

Geoff shares the ups and downs of a long and painful story; what it means to think and operate both in the here and now as well as focusing on the birds-eye view when it comes to bootstrapping a SaaS business.

We also dive into Outseta's choose-your-won adventure compensation model: a full-time salary of $210,000 for everyone with massive flexibility and choice.

Enjoy this conversation with a veteran of self-funded software.

Check out Podscan.fm! It's my media monitoring service that tracks every mention of you and your brand across all podcasts. Discover where your name pops up in the podcast world.

(And if you're a builder, the Podscan API allows access to fully transcribed episodes for millions of podcasts!)


Thank you for checking out this week’s interview edition of The Bootstrapped Founder. Did you enjoy it? If so, please spread the word and ​share this issue on Twitter.

To make sure you keep getting your weekly dose of Bootstrapped Founder, please add arvid@thebootstrappedfounder.com to your address book or whitelist us.

Did someone forward you this issue of The Bootstrapped Founder? ​You can subscribe to it here!​

Want to change which emails you get from The Bootstrapped Founder or unsubscribe for good? No worries, just click this link: ​change email preferences​ or ​unsubscribe​​.

Our postal address: 113 Cherry St #92768, Seattle, WA 98104-2205

Opt-out of preference-based advertising

Arvid Kahl

Being your own boss isn't easy, but it's worth it. Learn how to build a legacy while being kind and authentic. I want to empower as many entrepreneurs as possible to help themselves (and those they choose to serve).

Read more from Arvid Kahl

Podcast, YouTube, Blog Dear founder, When you build a software business as a founder, you have a dream. That dream is to build something that people actually need, that will make you money, and that you can keep building and make better - and make more money as you build it. Maybe there’s an extension to that dream where you sell it for millions, or where you build a company that allows you to retire. But the core of the dream is this: you have a thing that you think needs to be built, you...

Podcast, YouTube, Blog Dear founder, Here’s the thing: I’m about to share all the reasons why you should never, ever start a software business. And yes, I’m fully aware that I’m talking to an audience of software founders. This is somewhat sarcastic, somewhat ironic twist on the great things about entrepreneurship. THE BOOTSTRAPPED FOUNDER • EPISODE 421 421: Why You Should Never Start a Software Business 21:59 MORE INFO But here’s what I’ve realized - talking about the problematic sides of...

Podcast, YouTube, Blog Dear founder, I know you’re out there. The developer who watches their colleagues enthusiastically embrace Claude Code and Cursor, having AI write entire feature sets while you proudly type every semicolon by hand. The founder who sees AI-generated code as a ticking time bomb of bugs and security vulnerabilities. The software entrepreneur who believes that real code comes from human minds, not language models. This one’s for you. THE BOOTSTRAPPED FOUNDER • EPISODE 420...