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.

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.

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.

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.

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.

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 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.

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!

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. 

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.

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 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.

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 shortcuts are actually worth taking when you're building a SaaS?

In this episode, Rob Walling and fan favorite Derrick Reimer delve into listener questions about startup development. They discuss the impact of AI coding tools on building minimum viable products (MVPs) and the importance of user experience (UX) with advice on balancing UX investment based on the product's nature. 

You’ll also hear a breakdown of the real costs of leaving the cloud, plus tips on email deliverability and validation. Throughout, they highlight how validating ideas through user feedback and research is still critical, no matter how fast you build.

This podcast is brought to you by Mercury. I've been banking with Mercury for years and whenever I set up a new account, I'm reminded why traditional banking feels stuck in the past. 

When our previous bank faced solvency issues, we needed to spin up new accounts quickly that could handle millions in funds across multiple businesses. Mercury had us up and running almost immediately.

I manage half a dozen different Mercury accounts across a wide range of companies – from my personal, single-member LLC to MicroConf, our 7-figure global events and education platform, to TinySeed, our venture fund and accelerator. Mercury easily handles them all.

The interface is elegantly simple for daily banking, paying invoices, and sending and receiving international wires, yet powerful enough to handle the multi-step approval processes we needed to put in place when funding founders with large transfers. 

Anytime founders ask me who they should set up their accounts with, I send them to mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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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