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.
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Mitchell Hashimoto: How Solving His Own Problem Sparked HashiCorp
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!
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Jake Knapp: The Founder’s Guide to Product-Market Fit
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!
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Amjad Masad: Resolve, Persistence, and the Rise of Replit
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!
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Aaron Levie: The Restless Founder Plotting the Future of Cloud Storage and AI
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!
Host Mike Maples Jr. from venture capital firm Floodgate offers lessons from the rare startup super performers — BEFORE they were successful. Pattern Breakers features interviews with some of Silicon Valley’s most legendary entrepreneurs and thought leaders, including Netscape co-founder Marc Andreessen, LinkedIn founder Reid Hoffman, Instagram founders Kevin Systrom and Mike Kreiger, business maverick Mark Cuban, and Shopify co-founder Tobi Lütke.
Ireland