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

The Bootstrapped Founder

06/26/24

35m

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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.

00:00:00 Building a Platform for SaaS Businesses
00:11:39 The Journey of Building Outsetta
00:17:47 Founding Team Alignment and Bootstrapping
00:26:01 Revolutionizing Compensation and Company Culture

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/geoff-roberts-playing-the-long-game/

The podcast episode: https://tbf.fm/episodes/333-geoff-roberts-playing-the-long-game

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

Previous Episode

This week was a duality of extremes for me. On one hand, I experienced an unprecedented growth spurt in my user numbers, while on the other hand, I stumbled into frustrating scarcity and infrastructure problems. That’s entrepreneurship for you: big wins while struggling to not lose control of the whole thing.

The juxtaposition of these two experiences in a single week was both challenging and enlightening. Today, I want to share the story of navigating the good and the bad simultaneously.

This episode is sponsored by Acquire.com

The blog post: https://tbf.fm/episodes/330-50-new-users-overnight-and-a-burning-server

The podcast episode: https://thebootstrappedfounder.com/50-percent-new-users-overnight-and-a-burning-server

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

Next Episode

What happens when the 'small bets' strategy leads to a big win, and you're not prepared for it?

Well, you adapt! So that's what I'm working on this week: figuring out a way forward now that circumstances have shifted.

This episode is sponsored by Podscan.fm

The blog post: https://thebootstrappedfounder.com/beyond-small-bets-embracing-the-big-play/

The podcast episode: https://tbf.fm/episodes/332-beyond-small-bets-embracing-the-big-play

Check out Podscan to get alerts when you're mentioned on podcasts: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

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