
332: Beyond Small Bets — Embracing the Big Play
The Bootstrapped Founder
06/28/24
•10m
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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
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Podcast: https://thebootstrappedfounder.com/podcast
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My book Zero to Sold: https://zerotosold.com/
My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/
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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
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Previous Episode

331: Geoff Roberts — Playing the Long Game
June 26, 2024
•35m
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
Next Episode
@Kitze, a Serial indie hacker and entrepreneur, shares his journey through a landscape filled with multiple projects like Sizzy, a browser for developers, Benji, a productivity app, and a comprehensive full-stack video course.
Kitze opens up about how his ADHD diagnosis has shaped his work ethic and productivity, revealing the personal motivations behind creating tools like Benji. True indie hacker fashion: he built a tool that he needed for himself. And that kickstarted a lot of other things.
His candid anecdotes offer a rare glimpse into the life of a busy founder who constantly balances feature development, user experience design, and the demands of a growing user base.
00:00:00 Building Benji
00:03:42 Juggling Multiple Projects and Responsibilities
00:11:15 Founder's Dilemma
00:20:02 Navigating Founder-Investor Alignment
00:27:57 Marketing Strategies for Aspirational Products
00:33:41 Balancing Work-Life Priorities and Responsibilities
This episode is sponsored by Acquire.com
The blog post: https://thebootstrappedfounder.com/kitze-juggling-projects-adhd-and-the-indie-hacker-lifestyle/
The podcast episode: https://tbf.fm/episodes/333-kitze-juggling-projects-adhd-and-the-indie-hacker-lifestyle
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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