Pattern Breakers

For most of his 20s, James Beshara tried to go big as a startup founder in a hot category where he burned tons of money in hopes of getting big fast. Instead, he ended up with a heart condition and a fire sale. So he decided to radically rethink his approach, and start with a problem that he actually had. With coffee off the menu due to his medical condition, he began asking what he could use to stay alert throughout the day. Suddenly, the idea for Magic Mind was born.

In this episode, Mike Maples, Jr. of Floodgate speaks with Beshara about his early days founding the fintech company Tilt and what went wrong, the stress that landed him in the hospital, the origin story behind the mental performance shot company Magic Mind, and why solving your own problem makes you a domain expert likely to find yourself inside a community of people with the same issue.  

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even more Pattern Breaking content from Mike.  

Mike's book Pattern Breakers is available now wherever you buy books.

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When Silicon Valley Bank collapsed over 48 hours in March 2023, it marked the third-largest bank failure in United States history and the largest since the 2008 financial crisis. But the fintech company Mercury was willing and ready to save the day for startups in need, landing $2 billion in new deposits in five days. That's what it looks like when a founder who thinks about a problem all the time is ready to seize the moment when it arrives.

In this episode, Mike Maples, Jr. of Floodgate speaks with Mercury co-founder and CEO Immad Akhund about why  more than 200,000 of the world's most ambitious companies trust Mercury with their money, and why the company’s success was no accident. A prolific angel investor with a history of backing more than 350 startups including Ripple, Airtable, and Substack, Akhund had been living inside the startup ecosystem for years, and knew firsthand all about the challenges founders faced with banking. “In some ways the idea seems obvious to me,” Akhund  says. “There’s no reason banking has to be broken.”


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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Lyft co-founder John Zimmer helped spark a movement to revolutionize transportation, but the road was never a smooth one. Zimmer and co-founder Logan Green had to outmaneuver entrenched taxi monopolies and rewrite the rules of urban mobility on the fly, all while scaling a business model that many experts insisted was a logistical impossibility and battling Uber co-founder Travis Kalanick for market supremacy.

In this episode, Mike Maples, Jr. of Floodgate speaks with Zimmer about a variety of different essential lessons from Lyft’s journey, including his ability to spot anomalies and create a genuine breakthrough. They also discuss the origins of and strategy behind Lyft’s iconic pink mustache logo, how Uber operatives tried to bring Lyft down, and why he’s always taken the answer “no” as an invite for a conversation.  

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 Amplitude launched in 2012, the analytics market looked crowded, and the company spent more than a year struggling to find any traction. But co-founder and CEO Spenser Skates prioritized truth seeking over narratives. He studied the outcomes of past Y Combinator batches and noticed a simple rule: Most companies died before they even learned enough to make something that people want. All Amplitude had to do was survive.
In this episode, Mike Maples, Jr. of Floodgate speaks with Skates about that crucial realization and how his company preserved through its first two years on the map, why he’s never been afraid of failure, Amplitude’s surprising early adopters, the value of learning sales skills, and how he tries to raise the bar for the company even higher amid all of its success.


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 Wade Foster was a kid growing up in Jefferson City, Missouri, there weren’t many models for how to carve out a career in entrepreneurship. But when he and his friend Bryan Helmig developed an easier way to help users connect web-based applications, they ushered in what would eventually become Zapier, a remote automation giant that’s now worth an estimated $5 billion and is ideally positioned for the AI era.

In this episode, Mike Maples, Jr. of Floodgate speaks with Foster about his early days in Missouri and his first impressions of Silicon Valley, the concept of seed-strapping and how the company has thrived despite raising just $1.3 million, the importance of making constant contact with reality, and why Zapier is the perfect model for how to build a large-scale company while challenging virtually every part of the conventional wisdom.  

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!