A Product Market Fit Show | Startup Podcast for Founders

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21 snips
Jul 28, 2025 • 51min

He went viral at 11 y/o—built the world's best dictation app, then raised a $30M Series A. | Tanay Kothari, Founder of Wispr Flow

Tanay Kothari, the founder of Wispr Flow and a coding prodigy who built a voice assistant at age 11, shares his remarkable journey in tech. He reveals how Wispr Flow evolved into an AI powerhouse, emphasizes the importance of product-market fit, and highlights the mistake that nearly derailed his startup. Tanay also offers insights into building effective teams and the power of incremental change. With a recent $30M Series A under his belt, his experiences are a treasure trove for aspiring founders.
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18 snips
Jul 24, 2025 • 18min

PMF Observations: Why after PMF, every problem is a people problem.

Explore the intriguing concept that most startup challenges after achieving product-market fit are rooted in people issues. Discover how staying close to customers can expedite your path to success. Learn the importance of identifying true A-players on your team and hear the compelling story of a platform that disrupts industries by offering services for free. Embrace the idea that radical differentiation often trumps incremental changes, and uncover how subtle details can make or break your product's success.
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17 snips
Jul 21, 2025 • 55min

How Mercury Hit $500M ARR—then raised $300M from Sequoia at $3.5B. | Immad Akhund, CEO & Founder of Mercury

Immad Akhund, CEO and Founder of Mercury, a rapidly growing fintech startup, shares his journey from launching Mercury to achieving $500M in annual revenue. He discusses how Mercury leveraged Twitter for explosive user growth and the surprising ease of fundraising without initial customers. Immad emphasizes the importance of defining company culture early and how this foundational element was crucial for their success. His insights on achieving product-market fit and navigating the challenges of startup growth are invaluable for aspiring entrepreneurs.
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27 snips
Jul 17, 2025 • 58min

Mike Maples: Your Startup Idea Isn’t Crazy Enough—And it's holding you back | Mike Maples, Founder of Floodgate

Mike Maples, founder of Floodgate and author of Pattern Breakers, discusses the boldness required for startup success. He explains that true breakthroughs come from rejecting consensus and embracing radical innovation. Maples emphasizes that a startup's biggest risk isn't failure, but rather spending years on an idea that's not worth it. He also stresses the importance of understanding market dynamics and warns against raising too much money too soon. His insights encourage founders to innovate fearlessly and focus on creating ideas that polarize rather than please.
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11 snips
Jul 14, 2025 • 51min

How he grew to $100M ARR—then exited for $460M. | Zuben Matthews, Founder of Brigit

Zuben Matthews, the founder of Brigit, transformed his personal battle with overdraft fees into a booming fintech company that sold for $460 million after reaching $100 million ARR. He discusses uncovering massive market pain, emphasizing how solving real customer issues fuels growth. Zuben shares invaluable insights on validating product-market fit quickly and why unit economics are crucial early on. He offers a candid look at navigating tough fundraising challenges and the emotional rollercoaster leading up to a major acquisition.
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7 snips
Jul 10, 2025 • 37min

He Hit $3.5M ARR and Still Failed. Here’s His #1 Mistake. | Joseph Lee, Founder of Freshline

Joseph Lee, founder of Freshline and now working on Super Demo, shares the rollercoaster of building a seafood marketplace that reached $3.5 million in revenue. Despite early traction, he reveals the hidden reasons marketplaces often fail, emphasizing the critical importance of finding the right market over mere grit. Joseph also discusses the unique challenges he faced, including COVID-19's impact and the complexities of fish distribution. His insights on rethinking startup advice and the difference between 'painkillers' and 'vitamins' are particularly illuminating.
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11 snips
Jul 3, 2025 • 14min

PMF Observations: Why it doesn't matter how fast you get to $1M ARR

Uncover the unexpected truths behind startup journeys and why fast revenue isn't the ultimate goal. Hear inspiring stories of founders like those from Carbon6 and Graphite, illustrating the power of patience and adaptability. Dive into the significance of chasing true product-market fit instead of merely racing to $1M ARR. Learn how randomness can lead to success and why copying others may backfire. Strategies like roll-ups and pivots could be the key to breakthrough growth—embracing the unpredictable might be your best bet!
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18 snips
Jul 3, 2025 • 1h 3min

1st-time founder raises $140M with $0 revenue—grows to 800 employees & profitable. | Andrew Rubin, Founder of Illumio

Andrew Rubin, founder of Illumio, shares his incredible journey in the cybersecurity realm. He raised $40M in just 6 months without a product, followed by another $100M before generating revenue. Rubin discusses the critical balance between being early and being too early in the market. He emphasizes that true startup survival hinges on conviction and customer insights. Listeners will also learn about the complexities of securing enterprise customers and the emotional rollercoaster of navigating rapid growth and funding challenges.
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12 snips
Jun 30, 2025 • 56min

He went 7 years with no revenue— then grew to $100M ARR. | Rob Woollen, Co-Founder of Sigma

Rob Woollen, Co-founder of Sigma Computing, shares his journey from years of struggle to achieving $100M ARR. He reveals the tough lessons learned during seven years without revenue and the crucial pivots that transformed failure into success. Rob emphasizes the importance of patience over speed in reaching product-market fit and discusses the psychological toll of startup uncertainty. He also highlights the unexpected power of building features that customers didn't request, showcasing how innovation thrives on resilience and user-centric design.
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26 snips
Jun 26, 2025 • 50min

$10M Raised, 500K Users, but she still failed—here’s what went wrong | Benedetta Lucini, Founder of Oval Money

Benedetta Lucini, founder of Oval Money and former Uber manager in Europe, shares her candid startup journey. Despite raising $10M and gaining 500K users, she reveals how chasing big partnerships can derail success. Benedetta discusses the pitfalls of corporate VC reliance, the complexities of adapting US models to Europe, and costly fundraising mistakes. She encourages founders to validate ideas before building tech and highlights the emotional toll of making tough decisions when facing failure. This is a must-listen for aspiring entrepreneurs.

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