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.

• (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!

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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.

• (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

• 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

What’s it take to bootstrap a niche SaaS to $90M without raising a dime?

In this episode, Kevin Wagstaff joins Rob Walling to share how he and his brother bootstrapped Spectora from a scrappy MVP to a $90M valuation. It’s a masterclass in finding traction in unsexy markets, building with empathy, and making smart bets like embedded payments.

• (4:39) – The surreal moment Kevin and his brother became multimillionaires
• (9:14) – Why a mobile-first approach won in an outdated, overlooked niche
• (17:39) – How adding payments created a second revenue stream and bigger valuation
• (20:36) – The early hustle: trade shows, 6 AM demos, and Facebook group tactics

• SaaS Launchpad Course
• MicroConf
• Kevin Wagstaff | LinkedIn
• Kevin Wagstaff (@KevinWagstaff3) | X
• Spectora
• Kevin’s Built to Sell Radio Episode

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