Tanay started coding at 10, built a product with millions of users by 11, and never stopped. In this episode, he shares how he created Wispr Flow—one of the fastest growing AI startups today. He's built the world's best voice to text app. I use it myself every single day. And he just raised a $30M Series A from Menlo Ventures 

This is a must-listen for any founder obsessed with building something users can’t live without.

Why You Should Listen

• How Tanay built one of the world’s first voice assistants at 11—and what it taught him about startups.
• Why most founders get product-market fit wrong 
• The critical mistake that almost killed Wispr AI
• The one thing Tanay wishes he’d known about building a startup team five years ago.

Keywords
product market fit, AI startup, Wispr Flow, Tanay Kothari, founder stories, startup pivot, voice interface, building teams, hyper-growth startup, deep tech startup

00:00:00 Intro

00:07:22 Learning to Code in Secret

00:13:27 From New Delhi to Stanford and Silicon Valley

00:17:34 Feather X—Tanay’s First Big Startup Exit

00:24:33 The Original Moonshot Vision of Wispr AI

00:31:19 Why Wispr AI Had to Pivot

00:38:32 The Power of Incremental Change Over Radical Shifts

00:43:00 Achieving Explosive Growth and True Product-Market Fit

00:49:01 The Most Important Lesson—Building the Right Team

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We go through some lessons I learned from my own startup journey. I also go through  why almost every business challenge beyond product-market fit is actually a people issue—and how to quickly spot and fix these hidden problems. You’ll learn why staying in direct contact with your customers accelerates your path to true product-market fit, and hear a powerful story of how making something radically different—even free—can disrupt entire industries and create massive competitive moats.

Why You Should Listen

• Discover the #1 reason your startup’s growth might be stalling
• Learn why staying hands-on with sales longer accelerates finding PMF
• Find out how to instantly identify if your team members are truly A-players.
• Uncover the hidden power of making your product free—even when competitors think you’re crazy.
• Understand why radically different strategies beat incremental improvements every time.

Keywords

product market fit, startup hiring, startup growth, founder lessons, free business model, early stage sales, team building, radical differentiation, founder mistakes, scaling startups

00:00:00 Intro

00:04:21 Every Startup Problem is Actually a People Problem

00:05:56 How to Identify Great Talent Without Hiring

00:07:10 Why Founders Should Stay in Sales Longer

00:09:35 Subtle Details are The Key to True Product Market Fit

00:12:24 Zeffy and the Hidden Power of Being Radically Different

00:17:00 The ROI of Being Uniquely Different

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Immad grew Mercury to $500M in annualized revenue and profitable. Mercury is one of the fastest-growing fintech startups ever. No wonder they just raised $300M from Sequoia at $3.5B. 

Immad breaks down exactly how he structured a viral launch, why fundraising is easier with zero customers than you think, and how he unlocked massive word-of-mouth growth. If you’re building a startup, especially in fintech, you can’t miss this episode.

Why You Should Listen

• How Mercury went from $0 to $1M ARR in just 5 months
• How Mercury leveraged Twitter to explode user growth at launch
• Why building with zero users might be your secret advantage
• Why Immad believes defining company culture at employee #4 was critical to hitting $500M in revenue

Keywords

Mercury, Sequoia, Immad Akhund, startup fundraising, fintech startup, product market fit, neobank, early-stage growth, Y Combinator, banking as a service, startup culture

00:00:00 Intro

00:09:23 How Immad Validated the Idea for Mercury

00:17:53 Why Immad Turned Down VC to Start Another Company

00:28:11 How Immad Raised a $6M Seed Round Before Writing Any Code

00:36:08 Launching Mercury and Going Viral on Twitter

00:47:08 Knowing You Have Product Market Fit

00:51:48 Raising a $20M Series A Just 3 Weeks After Launch

00:53:10 The Importance of Defining Your Culture Early

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Ever wonder why some startups follow every “right” rule and still fail, while others break every norm and dominate? Mike Maples (Floodgate, author of Pattern Breakers) reveals how true breakthrough startups aren’t built by checking boxes—they’re created by founders bold enough to reject consensus, ignore conventional wisdom, and rewrite the rules entirely. 

This episode explains why your biggest risk isn’t failure, it’s wasting years on the wrong idea. If you want to build something people are desperate for, not just mildly interested in, Mike’s insights will change how you think about startup success.

Why You Should Listen

• How to know if your startup idea is worth years of your life—or if it’s secretly wasting your time.
• Why “non-consensus and right” ideas create billion-dollar breakthroughs.
• How raising too much money too soon can sabotage product-market fit.
• The difference between playing by market rules and inventing your own.
• Why the best startup ideas polarize rather than please everyone.

Keywords

product market fit, startup ideas, breakthrough startups, seed funding, Mike Maples, lean startup, inflection points, AI startups, zero to one, startup growth

00:00:00 Intro

00:04:12 The Real Reason “Pattern Breakers” Win

00:12:00 Stop Finding Problems Start Living in the Future

00:21:23 Why Most Founders Play the Wrong Game

00:31:01 How to Know You’re Actually in the Future

00:36:38 The Hidden Cost of Raising Too Much Money

00:46:20 The True Purpose of Your First Million in ARR

00:50:58 Three Tests to Know You’ve Found Product Market Fit

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Zuben turned his personal experience with crippling overdraft fees into Brigit, a fintech he sold for $460 million after hitting $100M ARR. This episode gives early-stage founders the unfiltered truth: how Zuben discovered massive market pain hidden in plain sight, validated the idea with real customers, built bulletproof unit economics early, and navigated brutal early-stage fundraising. It’s a real story about solving problems banks deliberately ignore—and getting rewarded big time. 

You don’t want to miss this.

Why You Should Listen

• How Zuben turned a personal $1000 overdraft nightmare into a $460M exit.
• Why solving your customer’s deepest pain point is the only way to unlock real growth.
• How to validate product-market fit fast (and what most founders miss).
• The surprising reason Zuben says unit economics matter way earlier than you think.

Keywords

fintech, overdraft fees, product market fit, earned wage access, early stage startups, customer validation, fundraising, founder stories, lending, unit economics

00:00:00 Intro

00:08:47 Inside the Hidden Overdraft Market

00:16:34 Validating Your Idea the Right Way

00:27:37 How Brigit Cracked Customer Acquisition

00:33:38 Why Unit Economics Saved Us

00:37:08 Navigating a Crisis and Coming Out Stronger

00:45:14 Behind the Scenes of a $460 Million Acquisition

00:48:57 The Moment of True Product Market Fit

00:50:22 Advice Every Early-Stage Founder Needs

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Joseph built Freshline to $3.5 million in revenue and nearly $2 million raised. It looked like a marketplace success story—until it wasn’t. In this episode, Joe shares the hidden reasons marketplaces fail, critical lessons on how to spot the right market, and why traction alone doesn’t guarantee success. It’s a raw, real look at what happens when hype meets reality.

Why You Should Listen

• How a $3.5M startup stalled despite traction
• Hard lessons on finding the right market
• The hidden traps of marketplaces
• Why staying gritty isn’t always enough
• Painkillers vs. Vitamins Rethinking Startup Advice

Keywords

marketplace, product market fit, startup failure, raising capital, entrepreneurship, founder advice, traction, B2B SaaS, early-stage startup, growth challenges

00:00:00 Intro

00:04:10 Crashing the Boston Seafood Expo

00:08:25 From Shopify to Marketplace

00:12:40 Door-to-Door Fish Sales

00:17:55 Hidden Risks of Marketplace Models

00:23:05 Cracks Emerge at $3.5M Revenue

00:26:45 COVID Hits and the Pivot Begins

00:30:50 Why Market Matters More Than Grit

00:32:55 Rethinking Painkillers vs Vitamins

00:35:30 Staying Alive Long Enough to Win

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Forget what you thought about early-stage growth. In this must-listen episode, you’ll hear firsthand how startup success truly happens—and spoiler alert, there’s no playbook. From companies like Carbon6 using roll-up strategies to Graphite pivoting multiple times before exploding, we unpack real founder journeys that prove getting to $1M ARR fast isn’t what matters. You’ll see why the real winners chase true product-market fit, why copying competitors is a trap, and why patience in the early stage might be your biggest competitive advantage. If you’re building a startup, stop what you’re doing and listen now.

Why You Should Listen

• Discover why getting to $1M ARR fast is NOT the goal (and what really matters instead).
• Learn how randomness and serendipity shape startup success—straight from real founder stories.
• Understand why chasing product-market fit beats obsessing over short-term revenue milestones.
• Hear why copying existing playbooks can sabotage your startup’s long-term growth.
• Find out how radically different paths—roll-ups, pivots, or total serendipity—can all lead to success.

Keywords 

product market fit, startup growth, early-stage startups, founder stories, zero to one, ARR milestones, startup pivots, product differentiation, scaling startups, startup playbook

00:00:00 Intro

00:02:47 Carbon6’s $210M Exit—Roll-ups and Serendipity

00:04:27 Lightspeed’s Unplanned Journey to $1B

00:06:04 Graphite’s Pivots—How a Failed Idea Led to Success

00:07:27 Vapi’s Rapid Rise After Three Years of Flat Growth

00:08:55 Why There’s No Single Path to Product Market Fit

00:11:19 The Million-Dollar ARR Myth

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Andrew Rubin raised $40M in 6 months before writing a single line of code—and another $100M before seeing his first dollar of revenue. Today, Illumio is valued at billions and counts Morgan Stanley among its earliest customers. But Andrew’s journey wasn’t smooth or easy. Listen in to learn how he navigated the fine line between being early and being too early, how he raised venture capital at unprecedented speed, and why he believes an entrepreneur’s conviction—backed by customer insights—is the real key to startup survival.

Why You Should Listen

• How to raise $40M in 6 months with no product or revenue
• Why “too early” often means bankrupt—and how to avoid it
• Why activity ≠ funding (and what to do instead)
• The hard truth about selling enterprise early
• Why market timing matters more than product genius

Keywords

product market fit, fundraising, early-stage startups, startup fundraising, venture capital, enterprise sales, market timing, Andrew Rubin, Illumio, cybersecurity

00:00:00 Intro

00:08:15 Why Being Early Can Bankrupt You

00:16:09 Creating a Market That Doesn’t Exist

00:27:55 Activity Does Not Equal Funding

00:38:06 Landing the First Enterprise Customer

00:49:57 Surviving Enterprise Sales Cycles

00:54:56 Navigating the Emotional Rollercoaster

01:00:46 The Truth About Product Market Fit

01:01:55 Andrew Rubin’s Best Advice for Early Founders

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Rob Woollen, founder of Sigma Computing, shares the unfiltered reality of going from 0 to $100M ARR. After spending seven years grinding without product-market fit, Sigma finally hit an inflection point—tripling revenue year over year. Rob dives deep into the pivots, setbacks, and critical decisions that turned early failure into a massive success. If you’re an early-stage founder feeling stuck, this episode will show you how patience, resilience, and radical product decisions can transform your startup.

Why You Should Listen

• How Sigma went from $0 to $100M ARR—but spent 7 years figuring it out.
• The pivot that turned years of failure into explosive growth.
• Why obsessing over speed to product-market fit is the wrong game.
• How to handle the psychological toll of startup uncertainty.
• The hidden power of building features your customers never ask for.

Keywords

product-market fit, Sigma Computing, pivot, startup growth, business intelligence, Snowflake, early-stage startup, SaaS growth, cloud analytics, founder stories

00:00:00 Intro

00:02:49 Debating speed to product–market fit

00:10:14 Quitting Salesforce and the EIR leap

00:23:12 Two years of prototypes that went nowhere

00:36:53 The Snowflake meeting and spreadsheet pivot

00:45:41 Dealing with Investors

00:52:30 Tripling three years straight to $100M ARR

00:54:46 Why most people shouldn’t start a company

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This is the brutally honest startup story every founder needs to hear. Benedetta  shares how she built a fintech app to half a million users and raised $10M—yet still failed. 

You’ll learn why chasing big partnerships can backfire spectacularly, how a seemingly successful startup can quietly fall apart, and how to set yourself up to avoid common but deadly fundraising mistakes. 

This isn’t just another success story; it’s a real guide on how not to fail.

Why You Should Listen

• Discover why even rapid growth and millions raised might not save you.
• Find out the hidden dangers of relying on corporate VCs.
• Learn why equal founder equity splits might not be a good idea.
• Hear the biggest fundraising mistakes early-stage founders make (and how to avoid them).
• Get practical advice on how to truly validate your startup before building tech.

Keywords

startup failure, fundraising mistakes, fintech startup, founder lessons, corporate VC, startup partnerships, product validation, founder equity split, early-stage fundraising, startup growth challenges

00:00:00 Early Days at Uber and Moving into Fintech

00:07:00 Launching a Consumer Fintech App in Europe

00:13:37 Validating Without Tech Building an MVP by Hand

00:19:22 Why US Startup Models Don’t Work in Europe

00:23:07 Raising Money Quickly—and the Hidden Costs

00:28:56 Running Out of Cash When COVID Hit

00:32:15 Tough Decisions Layoffs, Sales, and Shutdown

00:37:53 How Big Partnerships Can Sink Your Startup

00:43:41 Staying Optimistic Even When Everything Falls Apart

00:46:38 Crucial Fundraising Advice for Early-Stage Founders

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