Looking back on your entrepreneurship journey, which decisions made the biggest impact?

In this solo episode, Rob Walling breaks down the 10 decisions that shaped his success, like choosing action over perfection, learning fast from failure, and building a financial cushion to take smarter risks. It’s an honest look at what worked and the choices that made the biggest difference.

• (2:53) – Stop reading, start shipping
• (4:48) – Learn from mistakes and change course
• (6:47) – Build a financial cushion
• (8:38) – Write publicly about your journey
• (13:04) – Make bigger, but manageable bets
• (15:21) – Embrace the unsexy, grindy work
• (18:05) – Identify blind spots to grow faster
• (19:39) – Set clear goals and stick to them
• (21:26) – Know when to persist, pivot, or quit
• (24:40) – Don’t make decisions in emotional moments

• MicroConf Connect
• Start Small, Stay Small
• Comic Lab Podcast
• TinySeed Institute

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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Are you repeating any of these mistakes in your business?

In this episode, Rob Walling walks through his ‘founder regret list’, detailing 12 key mistakes from his 20-year entrepreneurial journey. In this very personal episode, he tells some stories he’s never shared publicly before.

• (4:17) – Thinking venture capital was the only path
• (6:12) – Launching without validating the idea
• (9:26) – Choosing ideas that couldn’t be bootstrapped
• (12:48) – Relying too much on books
• (16:36) – Trying to do everything solo
• (21:10) – The arrival fallacy
• (23:19) – Delaying email list growth
• (25:51) – Taking random advice too seriously
• (28:43) – Overestimating skills after early wins
• (30:29) – Letting anxiety steal the joy from success
• (32:34) – Not letting wins build confidence
• (33:50) – Holding onto a scarcity mindset

• TinySeed Institute
• Sponsor the Podcast or MicroConf
• Start Small, Stay Small
• The SaaS Playbook
• Zero to Sold by Arvid Kahl

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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What if your biggest growth blocker isn’t the market, but the story you’re telling yourself?

In this episode, Rob Walling welcomes back fan favorite Ruben Gamez, founder of SignWell, to debunk common bootstrapper myths. They discuss misconceptions like never needing to sell your company or market your product, and emphasize the realities of growth plateaus, business valuation, and exit strategies.

• (4:50) – I’ll never sell my company
• (11:40) – I can just coast on profit forever
• (21:48) – I’m built differently, so I don’t need to market
• (31:54) – Building many tiny projects is a strategy
• (34:46) – It’s all about luck

• Invest in TinySeed Fund 3
• Ruben Gamez (@earthlingworks) | X
• SignWell
• Ruben Gamez | LinkedIn
• MicroConf YouTube Channel

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify