The Bootstrapped Founder

294: RoxCodes — Building Dreams and Letting Go


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Rox (@RoxCodes) recently sold his SaaS thumbnailtest.com. But he's pretty conflicted about the sale. What was promised to be a moment of joy and celebration quickly turned into doubt, grief, and confusion.

Today, I talk to my friend Rox about the emotional complexity of giving up something you hold dear, how to move forward, and what it means to level up even further after a successful exit. Rox opens up and talks candidly about the weight on his shoulders, the pressure, and the expectations.

"Surrender" is the operative term here. If you ever wondered just how nuanced the sale of a business can be and how a founder has to struggle their way through it, this one's for you.

Rox on Twitter: https://twitter.com/RoxCodes

00:00:00 Founder Talks Acquisition and Business Surrender
00:08:07 Choosing Potential in San Francisco
00:13:04 Building Creator-Led Software
00:25:13 Building a Software Entrepreneurship With Creators
00:30:12 Challenges of Building a Public Persona
00:44:41 Emotional Toll of Selling a Business
00:51:42 Navigating Challenges, Building Next Venture

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/roxcodes-building-dreams-and-letting-go/

The podcast episode: https://tbf.fm/episodes/294-roxcodes-building-dreams-and-letting-go

The video: https://youtu.be/OG7ExrERbuY

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


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  • (00:00) - Founder Talks Acquisition and Business Surrender
  • (08:07) - Choosing Potential in San Francisco
  • (13:04) - Building Creator-Led Software
  • (25:13) - Building a Software Entrepreneurship With Creators
  • (30:12) - Challenges of Building a Public Persona
  • (44:41) - Emotional Toll of Selling a Business
  • (51:42) - Navigating Challenges, Building Next Venture
  • ...more
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    The Bootstrapped FounderBy Arvid Kahl

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