Pattern Breakers

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.

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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.

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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.

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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.

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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!