Pedro Franceschi: Lessons from an Evolving Entrepreneur, from Hacking iPhones to Building Brex

At just 13 years of age, Pedro Franceschi was one of the first to jailbreak the iPhone. By the time he was 15 he had co-founded a payments company that would process over a billion in transactions. And by the time he was in his early 20s, helped transform a last minute YC pivot into Brex, one of the most iconic fintech breakout stories of the decade. In this episode, Mike Maples, Jr. of Floodgate speaks with Franceschi about how he made headlines and found startup success in his native Brazil, why he traded it in for stints at Stanford and YC, how mental burnout can destroy a business, and why adaptive flexibility can be a vital founder superpower, if you build it like a muscle with practice, commitment and time.   Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

 The most successful founders don't usually chase startup ideas. Instead, they're pulled toward problems they can't ignore. Back in 2009,  Mitchell Hashimoto set out to fix what frustrated him by hacking nights and weekends, open sourcing the tools he wished had existed for over a year. His quiet persistence and commitment to fixing the problem ignited one of the decade's most influential cloud companies: HashiCorp. In this episode, Mike Maples, Jr. of Floodgate speaks with Hashimoto about those early days, building Vagrant to streamline dev setup, the dawn of HashiCorp, and the tough decisions Hashimoto faced when hiring a CEO and deciding if he should sell the company he built from scratch.   Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

For startups in the zero to one phase, finding product-market fit isn't everything. It’s the only thing. And there are few people in the entrepreneurial world better at solving the product-market fit puzzle than Jake Knapp, who helped build Microsoft Encarta and Gmail, co-founded Google Meet, and has advised teams at Miro, Slack, LEGO and NASA on product strategy and time management. Knapp also wrote the New York Times bestseller Sprint, and he’s a guest instructor at Harvard Business School. In this episode, Mike Maples, Jr. of Floodgate dives into the details of Knapp’s new book Click, which  helps founders figure out who your customer is, what problem they have, how your idea stands out, and how to test your idea quickly to see if it really works. The book offers 12 important lessons, a step-by-step playbook, and memorable stories from Nike, Microsoft, Google, and Slack, and helps founders to stop guessing and start building something people truly need.  Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

Amjad Masad's journey is defined by relentless persistence. Born and raised in Jordan, he borrowed computers to teach himself coding, and then earned money building software for local internet cafes. He applied to Y Combinator again and again, finally gaining acceptance on his fourth try. His constant drive fueled continuous improvement, culminating in the breakthrough success of Replit, the $1.1B company focused on empowering the next billion software creators.In this wide-ranging episode, Mike Maples, Jr. of Floodgate speaks with Masad about his journey from Jordan to Silicon Valley and the early days of Replit, how he always focused on figuring out the future of technology, the reasons some founders simply feel born to succeed, and why the 1997 book The Sovereign Individual resonates so loudly today.  Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.  Mike's book Pattern Breakers is available now wherever you buy books.Follow Mike on X!

When the team behind Box first went looking for funding back in 2005, they tried just about every trick in the book. They sent Bill Gates a fax. They dropped a prospectus off at Paul Allen’s house in Seattle. And they took a shot at convincing Mark Cuban to join two ambitious college kids  with a hunch the way businesses stored and collaborated around information was about to change. Two decades later Box is a cornerstone of the cloud era with $1 Billion in revenue, but co-founder and CEO Aaron Levie is as restless as ever. In this episode, Mike Maples, Jr. of Floodgate speaks with Levie about how he started Box when he was still in college at USC, why it’s fatal for startups to hire sales reps too slowly, and how he’s personally leading the way as the company looks to reinvent itself in the era of AI.  Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

Guillermo Rauch didn’t find success by accident. He began working on computers as a kid growing up in Argentina and was hooked immediately, eventually falling in love with programming and open source before moving to Silicon Valley. Since then his blend of technical foresight, audacious ambition and obsessive attention to detail in products has made him the successful CEO of Vercel, the cloud platform service company used by over a million developers each month, from small companies to tech giants like Netflix and Scale AI. In this episode, Mike Maples, Jr. of Floodgate speaks with Rauch about his early days as a programmer and connecting to open source community, the origins of his wildly popular blog post “7 Principles of Rich Web Applications” and how it led to founding Vercel, the importance for founders in telling their individual stories, and his thoughts on AI and how it will change the future of software development.  Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

Long before Plaid became a $13.4 billion fintech juggernaut, it was just another struggling startup. Co-founders Zach Perret and William Hockey burned through cash and pivoted from one failed idea to the next, ultimately getting turned away by roughly 100 VCs during seed round funding. But Plaid persevered, and eventually revolutionized how financial data moved through the internet, eventually boasting customers like Robinhood, Coinbase and Venmo. In this episode, Mike Maples, Jr. of Floodgate speaks with Perret about the company’s austere early days, convincing the banking industry to change its legacy ways, the concept of lighthouse customers, and why every day your startup lives, you get another chance to find greatness.   Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

As the co-founder of Robinhood, Baiju Bhatt didn't just help launch a company. He sparked a movement that fundamentally shifted the dynamics of investing, and created a new path for everyday people to participate in the markets. But can the man who changed the way people think about money do the same for energy? In this episode, Mike Maples, Jr. of Floodgate speaks with Bhatt about the origins of Robinhood and how hands-on research in the Stanford cafeteria helped the company find product-market fit, and how Bhatt’s new renewable energy company Aetherflux could make science fiction ideas a reality.  Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

When Josh Reeves, Tomer London and Edward Kim founded Gusto in 2012, roughly 40 percent of the employers in the United States were still doing their payroll by hand. Thousands of small business owners spent their time reading up on various federal and local tax codes or buried in late-night paperwork, drained of the energy to truly chase their dreams. In this episode, Mike Maples, Jr. of Floodgate speaks with Reeves about how Gusto identified pain points for small business founders everywhere, what it took to turn payroll from a grind into a tool that freed entrepreneurs to focus on what truly matters, and what he’s learned as the CEO of a revolutionary $9.5B software company.  Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!

Most startups stick to traditional methods of getting their message out. Pattern Breakers, however, don't follow the old rules of marketing. Instead they ignite a movement where they ultimately rise to the top, uncontested, while others later scramble for the leftovers. In this Breakthrough Lesson, Mike Maples Jr. of Floodgate examines three lessons learned from the recent viral breakout of the educational technology company Mentava, and why true Pattern Breakers don’t depend on the media or outside voices to shape their narrative. Instead, they speak for themselves, directly and boldly, telling the world their story in their own words.   Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books. Follow Mike on X!