Pattern Breakers

By FloodgateBusiness Entrepreneurship Technology Education How To

Pattern Breakers episodes

July 21 Max Mullen: How Instacart Solved the Problem of Grocery Delivery
When Max Mullen was a teenager, he used his mother’s credit card to order some candy and soda off the internet from the online company Kozmo.com. Less than an hour later his order arrived, and Mullen was hooked on grocery delivery as a breakthrough idea that could make people's lives easier. But by the time Mullen became a startup founder years later, Kozmo, Webvan, and their peers were buried in a Dot-Com graveyard, and investors were skeptical that grocery delivery would ever resonate beyond San Francisco.
In this episode, Mike Maples, Jr. of Floodgate speaks with Mullen about co-founding Instacart, lessons learned from the company’s early days, and why he divides startup decisions into three realms: science, religion, and art. Mullen also discusses why some of Instacart’s success traces back to the manager of a local Trader Joe’s, the moment he knew the company had found national product-market fit, and why he’s interested in robotic pets now that he’s a startup investor.
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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44 min
April 27 James Beshara: How a Dangerous Problem Led to a Magical Solution
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.
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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46 min
March 16 Immad Akhund: How Mercury Saved The Day For Startups
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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40 min
February 09 John Zimmer: Pink Mustaches, Rideshare Wars, and the Legacy of Lyft
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.
Follow Mike on X!
43 min
January 05 Spenser Skates: How Perseverance Paid Off for Amplitude
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!
45 min
November 18, 2025 Wade Foster: Why Zapier is Built for the AI Revolution
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!
43 min
September 29, 2025 Howie Liu: Building Airtable to Feel Magical
Spreadsheets were originally designed for finance people. But when Howie Liu and his co-founders started Airtable in 2012, they had a deeper insight that a spreadsheet-database hybrid could be used by anyone for just about anything, including project management, content calendars, recipes, and even travel itineraries. Now the company is valued at an estimated $4 billion, and it’s a prime example of why showing a real difference with your product is vital for achieving breakthrough success.
In this episode, Mike Maples, Jr. of Floodgate speaks with Liu about the original idea behind Airtable and the company’s early days of development, as well as why it took the company roughly two years to release a product to the public. They also discuss the value of visual metaphors and magical capabilities and how they helped Airtable differentiate from competitors in the market, as well as how Airtable is preparing for the future 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!
47 min
September 09, 2025 Joe Liemandt: The AI-Powered School Rewriting the Future of Education
Long before he attended Stanford, founded software giant Trilogy, or became the youngest member of the Forbes 400, Joe Liemandt wrote a high school paper about the potential for a futuristic technology called Artificial Intelligence. Four decades later Liemandt sits in the principal’s chair at Alpha School, an AI-powered private school founded in Austin, Texas with a revolutionary approach to learning and ambitious plans for the future.
In this episode, Mike Maples, Jr. of Floodgate speaks with Liemandt about what an average school day looks like at Alpha School, why kids can still excel with just two hours of focused academics per day, how the school teaches grit and self-confidence, what he’s looking for from pattern-breaking entrepreneurs eager to join his team, and what it was like to be stuck in an elevator with Maples, his college roommate at Stanford.
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!
43 min
August 25, 2025 Mårten Mickos: Essential Lessons From A Legendary Tech CEO
Mårten Mickos isn't the kind of CEO who tries to dream up world-changing ideas or invent brand new markets. Perhaps best known for leading MySQL to becoming a $1 billion success story that powered Facebook, Google, and YouTube, Mickos also led teams at Eucalyptus and HackerOne and has consistently shown an ability to convert the potential energy of an idea into the kinetic energy of execution.
In this episode, Mike Maples, Jr. of Floodgate speaks with Mickos about the essential lessons he’s learned from being a CEO, the importance of developing curiosity in the startup world, and why it’s essential to know your genius, own your gaps, and surround yourself with people who carry the tools you don't.
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!
42 min
August 04, 2025 Eric Schmidt: The Implications of Superintelligence
Best known as the CEO who helped transform Google from a promising startup into one of the best businesses in human history, Eric Schmidt has recently become one of the most important voices in the global conversation about artificial intelligence. He’s co-written two books on the subject including the New York Times bestseller Genesis: Artificial Intelligence, Hope, and the Human Spirit, co-written with longtime friend Henry Kissinger. He goes beyond examining what AI can do, and asks larger questions about the implications on human judgment, dignity, diplomacy, and democracy when intelligence is decoupled from morality.

In this episode, Mike Maples, Jr. of Floodgate speaks with Schmidt about how AI is transforming human agency, global stability, and the very nature of innovation, from personal super intelligence to geopolitical risk. The conversation dives deep into the moral, philosophical, and strategic stakes of AI's rise, and what it means for the future of humanity.

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!
41 min

About Pattern Breakers

From the publisher's feed

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…