What does it really take to go from six-figure student debt to financial independence, and then pivot again into a completely new career as a self-taught software developer? According to Jonathan Mendonsa, Co-founder of ChooseFI, the answer lies in something deeper than budgeting or hustle culture. It’s about building a freedom stack: a combination of mindset skills and systems that give you back the one thing money can never buy: time. In a recent episode of SaaS That App, Jonathan joins co-host Justin Edwards to unpack the principles that guided his journey, from the trenches of retail pharmacy to running a platform with tens of thousands of users, and how anyone can apply them, especially builders, developers, and bootstrapped founders.
On this special Thanksgiving episode of SaaS That App: Building B2B Web Applications, hosts Aaron Marchbanks and Justin Edwards stepped back from their usual deep-dive conversations about product architecture and growth strategies to celebrate something far more fundamental: the invisible support systems that allow founders to build meaningful businesses without destroying their marriages, their mental health, or their relationships with their children.
When Daniel Cannon bought his fixer-upper in Puerto Vallarta, he expected chaos. What he didn’t expect was the psychological déjà vu: the exact same emotional rollercoaster he’s felt during custom software builds, the mismatch between dream and reality, the “oh no” discoveries behind walls and inside code, the scope creep triggered by new shiny ideas halfway through a project, and the uncomfortable truth that the hardest part of any build isn’t the thing you want to build; it’s everything unexpected you discover along the way. This is the part nobody tells you: Whether it’s code or concrete, everything always takes longer, costs more, and changes more than you think it will. And that’s not failure. That’s the work.
When half the internet went offline because one single DNS record in one single AWS region got overwritten at the wrong millisecond, it was a very clear reminder for the entire world: even the most advanced, hardened, redundant, planet-scale infrastructure on Earth is still just infrastructure. It’s not magic. It’s not a guarantee. It’s someone else’s computer, and someone else’s software, with someone else’s race conditions, someone else’s delays, and someone else’s shortcomings. That’s why this AWS outage shook so many people.
What if the eight-hour gap between your 7 AM red-eye and 3 PM hotel check-in didn't have to be a caffeine marathon? That's the problem software engineer turned founder Jared Lerner of Nappr set out to solve, first with nap shops, then a consumer hosting pivot, and finally, a hotel marketplace that's now pacing at approximately 250 bookings a month.
Rewriting software is the tech equivalent of renovating a house while you’re still living in it: messy, expensive, and risky. Most of the time, you’re better off patching the roof and replacing the wiring than bulldozing everything. But sometimes, you really do need to burn it down and start over.
Tom Hunt isn’t just building tools; he’s building systems. Systems where the product is the marketing, where customer experience replaces ad spend, and where remote teams thrive through clarity, trust, and retention. At Fame, his podcast marketing agency, growth isn’t driven by noise; it’s engineered into the process. In this episode of SaaS That App: Building B2B Web Applications, Tom joins Aaron and Justin to share why outbound marketing feels like “wasted energy,” how to build retention into your company’s DNA, and what it takes to build a SaaS product that sells itself.
In this episode of SaaS That App: Building B2B Web Applications, Aaron Marchbanks and Justin Edwards sit down with Evan Shubin, a serial entrepreneur, startup operator, and founder of Results.now, to explore the hidden reasons why the vast majority of B2B tech startups flame out before they even get their product in front of real users.
In this episode of SaaS That App: Building B2B Web Applications, Matthew joins hosts Aaron Marchbanks and Justin Edwards to share why he left the enterprise world, how he's building a remote-first development team, and what it really takes to go from enterprise systems to scrappy MVPs, all while balancing scale, trust, and a deeply human approach to leadership.
When you think about the future of work, it’s impossible to ignore the seismic shift that AI is bringing to every industry, and perhaps nowhere more deeply than in software engineering. However, becoming truly AI-forward is more than sprinkling AI into your product roadmap or buying a license for the latest tool. It starts with […]