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.
Time Comes First
Jonathan begins with the reality many young professionals know too well: finishing school with a mountain of student debt and zero room to pivot. He left pharmacy school with $160,000 in loans, only to discover within two weeks that the job he had trained for eight years wasn’t for him. Debt doesn’t just drain your bank account; it locks you into decisions you no longer want to make.
His early mission was simple: reclaim his time, the most precious non-renewable resource. Debt freedom wasn’t about frugality, but unlocking optionality. Without the pressure of needing every paycheck, you gain breathing room to take calculated risks, switch careers, learn new skills, or build something new. And Jonathan did exactly that, paying off all $160K in just four years.
The Philosophy Behind the Freedom Stack
Jonathan opens up about the mental frameworks that guided every career pivot he has made. Together, they form the so-called Freedom Stack:
- Time is your most valuable asset.
Everything starts here. Money is renewable. Time is not. When you make decisions, optimize for regaining time, not accumulating things.
- Talent stacking beats traditional expertise.
Borrowing a concept from Dilbert creator Scott Adams, talent stacking means becoming top-20% good at multiple skills rather than world-class at one. Jonathan isn’t the best developer, podcaster, or community builder. However, the combination gives him a unique edge. The same applies to SaaS founders who blend technical ability, communication skills, curiosity, and business intuition.
- Curiosity is a career superpower.
With all the AI craze, your limits aren’t defined by your degree. They’re defined by your questions. If you’re not asking questions daily, you’re either bored or not paying attention. Curiosity fuels momentum, creativity, and rapid learning.
- You are the average of your ‘input stack.’
Jonathan reframes the classic five people you spend the most time with. Those people don’t need to be in your physical life. They can be authors, podcasters, creators, engineers, or founders. The content you consume shapes your mindset, and your mindset shapes your opportunity.
- Cockroach mode makes you unstoppable.
Not glamorous, but incredibly powerful. Keep your personal and business expenses as low as possible so you can take big swings without big risk. When your burn rate is near zero, you can build, ship, fail, iterate, and explore without the pressure that kills most bootstrapped projects.
From Podcast Co-Founder to Self-Taught Developer
Even after ChooseFI exploded into a global movement, Jonathan wasn’t done reinventing himself. Driven by curiosity, he taught himself to code, eventually building a fully functioning platform now actively used by 20,000+ members.
And he built it in the most indie-hacker way possible: publicly, imperfectly, and without a safety net. He didn’t wait until everything was perfect. He didn’t hide behind a dev team. He didn’t obsess over tests before shipping his first version. Instead, he treated the platform like a learning lab.
Audience-First is the New GTM Playbook
One of Jonathan’s strongest beliefs is that audience-first beats product-first.
Traditional venture-backed SaaS:
- Raise money
- Build in isolation
- Hope you guessed a real problem
Jonathan’s approach:
- Build a community
- Listen to what they struggle with
- Solve those problems, directly and visibly
When thousands of people tell you what they need, your roadmap writes itself.
Final Thoughts
Whether you’re buried in debt, stuck in a job you’ve outgrown, or simply craving more autonomy, Jonathan’s story is a reminder that reinvention is not only possible but practical.
Start paying down the things that steal your freedom.
Start stacking skills, not credentials.
Start asking better questions.
Start building publicly.
Start small.
Start now.
Because, as Jonathan says, “Today is the first day of the rest of your life. It only matters if you take action.”
Jonathan’s Background
Jonathan Mendonsa is the Co-founder of ChooseFI, a financial independence podcast with millions of downloads and hundreds of local community groups globally. With a background in pharmacy and a self-taught expertise in full-stack development, he has successfully built a platform ecosystem serving tens of thousands of users within the ChooseFI community.
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