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Floodgate

Pattern Breakers

A Entrepreneurship , Business and Technology podcast

#138 in Entrepreneurship · 🇺🇸 #158 in Business · 🇵🇭
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About the show

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.

Newest episodes

Victoria Hitchcock: What Founders Say Before They Speak

45 min

Silicon Valley made the hoodie a symbol of authenticity. But founders send a message before they speak, and it isn't always the one they intend. What happens when how you present yourself no longer reflects the leader you've become? Victoria Cardenas Hitchcock helps founders close that gap. A Bay Area image, wardrobe, and lifestyle consultant, she sees possibilities others miss and has the candor to say when something isn't working. For Hitchcock, personal style isn't about dressing up. It's about making outward appearance match identity, ambition, and the demands of leadership. In this episode of Pattern Breakers, Mike Maples Jr. talks with Hitchcock about Silicon Valley's changing style, the impressions founders overlook, and how to become more intentional without sacrificing authenticity. Metronome founder and CEO Scott Woody joins to share what working with Hitchcock taught him about how he shows up as a leader. 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!

Max Mullen: How Instacart Solved the Problem of Grocery Delivery

43 min

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. Follow Mike on X!

James Beshara: How a Dangerous Problem Led to a Magical Solution

45 min

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. Follow Mike on X!

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All episodes

Victoria Hitchcock: What Founders Say Before They Speak

45 min

Silicon Valley made the hoodie a symbol of authenticity. But founders send a message before they speak, and it isn't always the one they intend. What happens when how you present yourself no longer reflects the leader you've become? Victoria Cardenas Hitchcock helps founders close that gap. A Bay Area image, wardrobe, and lifestyle consultant, she sees possibilities others miss and has the candor to say when something isn't working. For Hitchcock, personal style isn't about dressing up. It's about making outward appearance match identity, ambition, and the demands of leadership. In this episode of Pattern Breakers, Mike Maples Jr. talks with Hitchcock about Silicon Valley's changing style, the impressions founders overlook, and how to become more intentional without sacrificing authenticity. Metronome founder and CEO Scott Woody joins to share what working with Hitchcock taught him about how he shows up as a leader. 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!

Max Mullen: How Instacart Solved the Problem of Grocery Delivery

43 min

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. Follow Mike on X!

James Beshara: How a Dangerous Problem Led to a Magical Solution

45 min

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. Follow Mike on X!

Immad Akhund: How Mercury Saved The Day For Startups

39 min

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. Follow Mike on X!

John Zimmer: Pink Mustaches, Rideshare Wars, and the Legacy of Lyft

42 min

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!

Spenser Skates: How Perseverance Paid Off for Amplitude

44 min

 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!

Wade Foster: Why Zapier is Built for the AI Revolution

42 min

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!

Howie Liu: Building Airtable to Feel Magical

46 min

 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!

Joe Liemandt: The AI-Powered School Rewriting the Future of Education

42 min

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!

Mårten Mickos: Essential Lessons From A Legendary Tech CEO

41 min

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!

Eric Schmidt: The Implications of Superintelligence

40 min

 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!

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

43 min

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!

Mitchell Hashimoto: How Solving His Own Problem Sparked HashiCorp

39 min

 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!

Jake Knapp: The Founder’s Guide to Product-Market Fit

41 min

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: Resolve, Persistence, and the Rise of Replit

39 min

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!

Aaron Levie: The Restless Founder Plotting the Future of Cloud Storage and AI

40 min

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: The Product Visionary Fueling Vercel and Millions of Developers

39 min

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!

Zach Perret: The Survival Story of a Fintech Giant

38 min

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!

Baiju Bhatt: First Robinhood, Next …. Outer Space?

40 min

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!

Josh Reeves: How Gusto Took The Pain Out Of Payroll

38 min

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!

Breakthrough Lesson: RIP To Old-School Marketing

10 min

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!

Niels Hoven: Teaching Two Year-Olds to Read Like Second Graders

34 min

The team behind the educational technology company Mentava is a small one, but its product idea is extremely ambitious: An app that teaches two year-olds to read at a second grade level. The idea is the brainchild of founder Niels Hoven, a father of four committed to accelerating K-12 education and helping high-achieving kids reach their true potential. In this episode, Mike Maples, Jr. of Floodgate speaks with Hoven about the origins of Mentava, how one very online critic gave the company an unexpected sales boost, and why Hoven has found himself engaged in a much bigger story about the shared and growing frustration with the cult of lower standards in education. 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!

Daphne Koller: Changing Lives With Coursera

43 min

Few startup founders follow a path to success like Daphne Koller, a polymath whose academic career in machine learning, computer vision, and computational biology make her a force far beyond the business arena. Koller left her academic career at Stanford in 2012 to co-found Coursera, the world’s largest platform for massive open online courses (MOOCs). After building the company into a global phenomenon she left Coursera in 2016 to become chief computing officer at Calico, and in 2018 she founded insitro, a drug discovery startup. In this episode, Mike Maples, Jr. of Floodgate talks with Koller about the origins of Coursera and the challenges the company faced in its early days, as well as its lasting impact for learners worldwide. She also discusses what she sees in the future for insitro and why she believes so strongly in machine learning-driven drug discovery and 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!

Pattern Breakers: Which Startups Change the Future?

36 min

On this special episode of Pattern Breakers, host Mike Maples Jr. of Floodgate joins LinkedIn founder and legendary investor Reid Hoffman for a conversation on Hoffman’s podcast Masters of Scale, where iconic business leaders share lessons and strategies that have helped them grow the world's most fascinating companies. Mike discusses the insights he’s gathered from decades of investing, inflection theory, what the latest AI sea change means for the future of business, and ideas from his new national bestselling book, Pattern Breakers. This episode originally aired on the Masters of Scale podcast. 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!

A Sneak Peek at Pattern Breakers

39 min

Today is a huge day for Pattern Breakers, the book. Co-written with Peter Zeibelman of the Stanford Graduate School of Business, Pattern Breakers has been dubbed “the most important start-up book of the last ten years” by legendary entrepreneur and co-creator of the Lean Startup movement Steve Blank. Pattern Breakers draws from decades of experience in entrepreneurship and venture capital from its co-authors to offer a radical set of new ideas for how entrepreneurs, investors, and corporate leaders can dominate the future. 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!

Maddie Hall: A Different Path to the Future

40 min

There is no single path to becoming the founder of a pattern-breaking startup. For Maddie Hall, her journey began with a crucial choice: to brainstorm startup ideas or to spend time with people already shaping the future. She chose the latter, following Sam Altman at OpenAI as his Chief of Staff. This experience, along with the connections and knowledge she gained, inspired her to co-found Living Carbon. Her startup offers "supertrees" that grow faster, produce harder wood, and absorb more carbon from the atmosphere. In this episode, Mike Maples, Jr. of Floodgate talks with Hall about her career path and how her decisions led her to start Living Carbon, where she is driven by the urgency of addressing the climate crisis. 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!

Breakthrough Lessons: Founder-Future Fit

12 min

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!

Justin Kan: Pattern Breaker Personified

41 min

If pattern breaker was a term in the dictionary, you just might find an image of Justin Kan. From his attempts as a teenager to send a camera to outer space, to selling his first company on Ebay, to strapping a camera to his head to play the starring role on Justin.tv, Kan has always been a man with uncommon ideas and the ability to convince people to follow his lead. On this episode, Mike Maples, Jr. of Floodgate speaks with Kan about the  runaway success of Twitch, but also his fear of scarcity, chasing extrinsic goals, and what he learned from his setbacks at Atrium, where he served as founding CEO. 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!

Breakthrough Lessons: The Value of a Superbuilder

11 min

In the early days of a start-up, the superbuilder can be as important to greatness as the start-up leader, and they’re often not the same person. But what are the traits of a great superbuilder, and why do they play such a crucial role in the zero to one phase of a company? In this Breakthrough Lesson, Mike Maples, Jr of Floodgate discusses the success of superbuilder Kyle Vogt and how his ingenuity saved Justin.tv, as well as how superbuilders help a startup tackle adversity and attract greatness to the team. 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!

Kyle Vogt: A Problem Solver With A Purpose

39 min

Kyle Vogt has always been fascinated with designing robots and machines. From his youngest days, he retrofitted his father's car to drive itself along the highways of his home state of Kansas. Later, he dropped out of MIT and became a wildly successful startup founder, playing a crucial role in the development of Justin.tv and Twitch. With Cruise Automation, he returned to his roots, making robotaxis a reality rather than science fiction. In this episode, Mike Maples, Jr. of Floodgate speaks with Vogt about his career and the lessons learned from a lifetime of solving problems. 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!

Breakthrough Lessons: Learning to Savor Surprises

11 min

The ability to notice and savor surprises is a key overlooked skill of the greatest founders. It allows you to narrow in on the types of capabilities that will lead to breakthroughs. In this Breakthrough Lesson, Mike Maples, Jr of Floodgate calls on the lessons learned by Twitch co-founder Emmett Shear to discuss why founders should seek surprises instead of validation, and how positive surprises can be a key source of 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!

Emmett Shear: How Twitch Changed Media by Merging it with Gaming

38 min

Emmett Shear was a gamer long before he helped define one of the most important new media companies at the intersection of gaming, media, and the creator economy. What can we learn from his success as a founder? (hint: it has something to do with truly listening to users.) 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!

Breakthrough Lessons: The One Thing That Matters Most…

10 min

In the early days of a startup, finding product-market fit is paramount. Once you have it, failure is almost impossible. Without it, you can do everything else right, and still fail. In this Breakthrough Lesson, Mike Maples, Jr of Floodgate discusses three heuristics for maximizing the odds of success: Find the right North Star, offer a Delta 4 experience, and don’t fool yourself. 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!

Michael Seibel: “The Godfounder” Discusses Justin.tv, Twitch, and Y Combinator

46 min

Michael Seibel didn’t set out to become a legendary startup founder. As a young man, his sights were set on politics, dreaming of a future on the Supreme Court. But his friendship with fellow Yale classmate Justin Kan led to a fortuitous cross-country trip to California that changed everything. In this episode, Mike Maples, Jr. of Floodgate talks with Seibel about the creation of Justin.tv and Twitch, and the wisdom he shares with aspiring founders as a partner and managing director at Y Combinator. 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!

Welcome to Pattern Breakers

6 min

Mike Maples, Jr. of Floodgate is back with a new season of his podcast, once called Starting Greatness, now renamed Pattern Breakers. The focus remains, but with increased ambitions. In this season intro, Mike explains his reasons for expanding the podcast's scope, what listeners can anticipate going forward, and details about a forthcoming book set to release this summer. Subscribe now so you don’t miss an episode, and check out the new Pattern Breakers letter on Substack at www.patternbreakers.substack.com to read essays and receive updates about what we can learn from the rare startups that achieved outlier success. It’s go time for Pattern Breakers! 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!

Breakthrough Lessons: Nail Your Niche

9 min

Founders are naturally drawn to the tantalizing potential of their product reaching a vast market, but the route to victory starts with nailing a niche before going for the broader opportunity. In this lesson of greatness, Mike Maples, Jr of Floodgate calls on the lessons of Spotify co-founder Daniel Ek to examine how this is done: Identify a stronghold where you can dominate, deliver a Delta 4 experience, and do everything possible to create unfair advantages in your favor. 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!

Daniel Ek: How Spotify Revolutionized The Music Business

47 min

When he was a little boy growing up in Sweden, Daniel Ek was obsessed with two things: the binary realm of computers and the artistry of music. As a young adult, he combined his love for both by co-founding Spotify, which became the global standard-bearer for streaming, Spotify now has more than 500 million users per month. In this episode, Mike Maples, Jr of Floodgate interviews Daniel Ek to break down the importance of recognizing technology infections, securing the perfect niche to secure early product-market fit, and how creating something radically different changed the music industry while redefining consumer listening habits. 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!

Breakthrough Lessons: Crisis Reveals Greatness

9 min

Startup founders dealt with uncertainty, stress and trauma in the wake of the run on Silicon Valley Bank, but the most important lessons from this crisis never showed up in social media. In this lesson of greatness, Mike Maples, Jr of Floodgate calls on the actions of a variety of founders who showed incredible courage and competence to showcase three crucial lessons for founders for how to deal with another potential crisis: Scenario planning, financial agility, and crisis communication. 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!

Untold lessons from the SVB bank run

32 min

The recent run on Silicon Valley Bank led to a variety of accusations, recriminations and finger-pointing on social media, but how can FOUNDERS actually learn from the crisis? And what lessons can we learn from the founders who crushed it under tough circumstances? In this episode, Mike Maples, Jr welcomes Floodgate co-founder Ann Miura-Ko on the show to discuss these topics. Mike and Ann also speak with SmarterDx CEO Michael Gao about how he handled a wild weekend for his company, and legendary marketing guru Christopher Lochhead stops by to discuss the best strategies for crisis communications. 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!

Breakthrough Lessons: Refuse Mediocrity

11 min

When we REFUSE to accept mediocrity, we can start building greatness. But how can you avoid the pitfalls of learned helplessness and help your company break through the arbitrary limits that impede progress? In this lesson of greatness, Mike Maples, Jr of Floodgate calls on the lessons of Boom Supersonic founder Blake Scholl to examine three tips to help founders develop startups that change the future: Embrace the belief you can make radical change, find a big problem that speaks to your soul, and then get maniacally focused on the details. 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!

Blake Scholl: How Boom Supersonic Took Flight

40 min

More than fifty years after the first Concorde took flight, consumer air travel is actually SLOWER. Blake Scholl and his team at Boom Supersonic are out to reverse this stagnation and change how we think about commercial aviation. In this episode, Mike Maples, Jr of FLOODGATE interviews Scholl to learn more about the history of American aviation, the origins of Boom Supersonic and the challenges it faces now, and how tech founders are exploring unfamiliar spaces with great 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!

Breakthrough Lessons: Leslie’s Compass

11 min

When a startup product goes to market, the two key muscles it can flex are marketing and sales. In nearly every facet of a startup product, marketing or sales takes the natural lead in getting the product to customers. But startups often pour resources into these two areas in unfocused ways, and the results can be disastrous. In this lesson of greatness, Mike Maples, Jr of FLOODGATE discusses the work of Silicon Valley legend Mark Leslie and specifically the framework of Leslie’s Compass, a simple but essential set of heuristics designed to bring more clarity and focus to your startup’s strategy. 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!

Mark Leslie: Silicon Valley Go-to-Market Legend (Part 2)

36 min

Mike Maples, Jr of Floodgate welcomes back go-to-market expert and Stanford Graduate School of Business lecturer Mark Leslie for the second of their two-part interview, this time focusing on the role and responsibilities of a CEO and a deep dive into Leslie’s Compass, an essential set of heuristics for every startup founder. Leslie also discusses the value of founders focusing on a five-year plan for their startup, why it’s challenging to make meaningful change inside a large company, and why every founder should understand the relationship between their sales and marketing departments. 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!

Breakthrough Lessons: The Sales Learning Curve

11 min

When a startup launches a new product, it's tempting to ramp its sales force too quickly. Often, this leads to a crash-and-burn scenario for companies that failed to learn what it took for the *entire organization* to achieve product-market-fit. In this lesson of greatness, Mike Maples, Jr of FLOODGATE discusses how Mark Leslie's Sales Learning Curve framework helps startups keep themselves honest about their progress toward product-market fit, rather than falling into the trap of wishful thinking that usually leads to disaster. 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!

Mark Leslie: Silicon Valley Go-to-Market Legend (Part 1)

45 min

During the 1990s, Mark co-founded Veritas Systems, which he piloted from nothing to 6,000 employees and $1.5B in revenue in a decade. Now a lecturer in management at the Stanford Graduate School of Business, Leslie is one of the foremost experts in go-to-market strategy in Silicon Valley, and in the first of this two-part series with Mike Maples, Jr of FLOODGATE, Leslie discusses what strategies he used to make Veritas a runaway success, and the origins for the Sales Learning Curve. 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!

Breakthrough Lessons: The Infinite Game

6 min

We’re taught from a young age about *finite* sporting games like baseball, basketball, and soccer. Or board games like checkers or chess. Or academic games like grades and test scores. Or status games like credentials and university degrees. In these games, we know the rules and how to determine who scored the highest, according to rules set by someone else. But what about *infinite* games, where the rules and players are changeable, and the primary goal is to keep the game going? In this lesson of greatness, Mike Maples, Jr of FLOODGATE discusses how Shopify founder Tobi Lutke exemplifies the advantages of playing the Infinite Game and how to tell when business leaders have fallen into the trap of finite games at the expense of achieving their mission. 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!

Tobi Lutke: A Startup Founder Arming The Rebels Against Amazon

40 min

Growing up in Germany, Shopify co-founder and CEO Tobi Lutke was never quite comfortable with people telling him to do things because that's the way they're done. In this episode, Mike Maples, Jr of FLOODGATE interviews Lutke to discuss the origins of Shopify, the difference between finite games and infinite games, and the reason it's important for startups and companies to always question assumptions imposed by "experts." 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!

Breakthrough Lessons: The Artistry of Startup Breakthroughs

8 min

Too many people mistakenly believe that being a good entrepreneur comes from simply talking to customers and solving their pain. But the most impactful companies are built for aesthetic reasons - think of Twitter, Lyft, Apple, and Medium - and those companies serve as expressions of what their founders thought the world needed. In this lesson of greatness, Mike Maples, Jr of FLOODGATE discusses the success of Pandora’s visionary founder Tim Westergren, and offers three tips for founders looking to bring a more aesthetically beautiful future to the world. 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!

Tim Westergren: How The Band Kept Playing At Pandora

41 min

Tim Westergren maxed out 11 credit cards, racked up hundreds of thousands of dollars in debt, and was rejected 348 times for a second round of funding for his revolutionary idea for a music streaming platform. But like any true artist, Westergren remained committed to his vision of creating an aesthetically more beautiful future with Pandora, and now the company boasts more than 6 million monthly subscribers. Mike Maples, Jr of FLOODGATE interviews Westergren to discuss the company’s humble beginnings, why it took an act of Congress to keep the company alive, and why both men believe the best founders are artists who can sell their vision. 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!

Breakthrough Lessons: “BIG D" Design

7 min

Lots of people think about design from the perspective of how a product should look and function. But design can be applied to greatness on many more levels than most realize. In this lesson of greatness, Mike Maples, Jr of FLOODGATE discusses how you can design your opportunity, your team, your market, your category, your culture, and even your own life. "Big D" design is about understanding that you have the chance to be more intentional in more areas that contribute to success than most realize. 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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