How do you choose between multiple product ideas?

In this solo episode, Rob Walling answers listener questions about picking between two SaaS ideas, product positioning, and how to know when to stop working on a project. Want to get your question answered? Drop them here.

• (3:06) – Choosing between two AI products
• (9:38) – Will early niche positioning hurt future growth?
• (14:51) – At what point would you consider lowering prices?
• (22:35) – Narrowing your ICP and product focus
• (28:07) – How do you spec agency projects?
• (30:10) – Should you keep building on a changing platform?

• MicroConf Europe | Istanbul, Sep 28-30, 2025
• SaaS Launchpad
• TinySeed
• The SaaS Playbook
• MicroConf Connect

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’s the real roadmap to lasting financial freedom?

In this episode, Rob Walling chats with Nick Maggiulli about his new book, The Wealth Ladder. Nick explains how to identify your current financial stage and what it really takes to move up. They dig into how wealth changes your spending habits, why exits (not salaries) drive significant changes in net worth, and how your definition of freedom might evolve over time.

• (6:07) – Defining the six levels of wealth
• (11:49) – Why earning more isn’t enough
• (14:17) – How entrepreneurs build wealth
• (15:15) – The “0.01%” spending rule
• (31:13) – Can money actually make you happier?

• Invest in TinySeed
• Of Dollars And Data
• The Wealth Ladder by Nick Maggiulli
• Just Keep Buying by Nick Maggiulli
• The E-Myth Revisited by Michael E. Gerber
• Nick Maggiulli | LinkedIn
• Nick Maggiulli (@dollarsanddata) | 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!

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When is the right time to sell your profitable SaaS?

In this week's episode, Rob Walling talks with Pierre de Wulf, co-founder of ScrapingBee, about how they mostly bootstrapped their web scraping SaaS to $5 million ARR and an eight-figure all-cash exit. They explore the pivotal shift that took them from $7K MRR to nearly $1M ARR in just 15 months, what Pierre splurged on post-exit, and the emotional, legal, and strategic complexities of selling a company.

• (3:31) – Why they chose to sell
• (5:41) – Post-exit emotions and celebrations
• (9:57) – Lessons from failed startups before ScrapingBee
• (13:16) – From 8k to $1m ARR in 15 months
• (17:14) – Building a scalable SEO content engine
• (29:19) – Handling a major cease-and-desist

• MicroConf Connect
• MicroConf Talk by Pierre de Wulf
• The Java Web Scraping Handbook
• ScrapingBee Blog
• TinySeed
• Discretion Capital
• Pierre de Wulf (@PierreDeWulf) | X
• Pierre de Wulf | LinkedIn

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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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

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.

• (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

• 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!

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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.

• (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?

• 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