How Cockroach Mode + Curiosity Rebuilt a Career from Scratch
December 2, 2025
What does it take to go from $160,000 in student debt to financial independence and then reinvent yourself as a self-taught developer? In this episode of SaaS That App: Building B2B Web Applications, Jonathan Mendonsa, Co-founder of ChooseFI, joins Justin Edwards to share how principles like talent stacking, cockroach mode, and curiosity-driven learning can help anyone design a career and life on their own terms.
This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a big SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.
Got a burning idea for an episode, or a SaaS question you absolutely must know the answer to? Leave us a voice memo at SaasThatApp
What does it take to go from $160,000 in student debt to financial independence and then reinvent yourself as a self-taught developer? In this episode of SaaS That App: Building B2B Web Applications, Jonathan Mendonsa, Co-founder of ChooseFI, joins Justin Edwards to share how principles like talent stacking, cockroach mode, and curiosity-driven learning can help anyone design a career and life on their own terms.
What You’ll Learn:
- Jonathan’s lessons from building a platform for tens of thousands of users
- How to escape debt-driven career constraints
- Why financial independence is really about reclaiming your time
- The cockroach mode advantage for bootstrapped builders
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.
This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a big SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.
Highlights:
Highlights:
- [00:00] Introduction
- [01:03] From Pharmacy to Freedom
- [04:57] Financial Independence as a Mindset
- [10:20] The Real Cost of Frugality
- [20:53] Why AI Will Reward or Replace You
- [25:20] Why Curious Killers Are Winning the Job Market
- [30:21] Building From Scratch
- [33:56] Audience-First Development
- [44:08] Iteration as Intuition
- [51:16] Jonathan’s Core Life Principles
Episode Resources:
- Jonathan Mendonsa on LinkedIn
- ChooseFI Website
- Aaron Marchbanks on LinkedIn
- Justin Edwards on LinkedIn
- Delta Systems Website
Got a burning idea for an episode, or a SaaS question you absolutely must know the answer to? Leave us a voice memo at SaasThatApp
We’d love your feedback. Please take a moment to fill out our audience questionnaire:
https://forms.gle/DN8hWFDcE9jwvNKo6
Your input helps us shape future episodes and continue bringing you practical, real-world insights into building B2B web applications.
https://forms.gle/DN8hWFDcE9jwvNKo6
Your input helps us shape future episodes and continue bringing you practical, real-world insights into building B2B web applications.