Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again
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.
Topics we cover:
(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
Links from the Show:
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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Episode 780 | "I'll Never Sell My Company" and Other Myths Founders Tell Themselves
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.
Topics we cover:
(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
Links from the Show:
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
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Episode 779 | 10 Myths Most SaaS Founders Believe
Are common SaaS myths sabotaging your success?
In this episode, Rob Walling sits down with SaaS growth expert (and TinySeed Institute coach) Marc Thomas to break down ten persistent and damaging myths believed by many SaaS founders and why challenging them is key to scaling smart.
Topics we cover:
(4:52) – “I’m not good at marketing” is a lie
(8:48) – Top-of-funnel obsession
(13:12) – Lifetime affiliate payouts = profit killers
(18:21) – Hiring a marketing team too soon
(21:52) – Chasing new markets too early
(25:08) – Fear of sending more email
(27:36) – Chasing shiny growth hacks like programmatic SEO
(31:14) – Dismissing sales in favor of only self-serve
(35:10) – Avoiding competitor content out of fear
Links from the Show:
MicroConf Europe – September 28–30 · Istanbul, Türkiye
TinySeed SaaS Institute
Positive Human
Marc Thomas | LinkedIn
Marc Thomas’ LinkedIn post on 10 SaaS Myths
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
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Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure)
How do you price pilot projects and niche down without hedging your bets?
In this episode, Rob Walling answers listener questions about pricing pilots, choosing niches, and skipping steps on his Stair Step Method of Bootstrapping.
Want to get your question answered? Drop them here.
Topics we cover:
(3:25) – Feedback on Season 4 of TinySeed Tales
(8:55) – How do you price pilot projects?
(15:11) – How to niche down and de-risking a new SaaS?
(22:40) – What does it really take to build a hit open-source tool?
(29:53) – Can you skip straight to SaaS or is that a trap?
Links from the Show:
MicroConf Connect: Online community of SaaS founders
TinySeed Tales Podcast
Startup Stories Podcast
Stair Step Method of Bootstrapping
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
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Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs
What if the traditional dream of retirement is actually a trap for entrepreneurs?
In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest, to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring and how shifting toward purpose-driven work can create more freedom, meaning, and longevity.
Topics we cover:
(2:17) – Why traditional retirement often leads to boredom and regret
(6:44) – How working longer can drastically reduce your savings burden
(11:05) – The power of $50K moments and appreciating time with loved ones
(17:03) – Prioritizing health and well-being as a long-term strategy
(21:42) – Smarter and more flexible alternatives to full retirement
Links from the Show:
MicroConf Europe – September 28–30 · Istanbul, Türkiye
TinySeed – Invest
Let’s Retire Retirement – Book on Amazon
Derek Coburn’s Website
Derek Coburn | LinkedIn
Derek Coburn (@cadredc) | X
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
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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