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Every founder has 1 goal: find product-market fit. We interview the world's most successful startup founders on the 0 to 1 part of their journeys. We've had the founders of Reddit, Gusto, Rappi, Glean, Cohere, Huntress, ID.me and many more. We go deep with entrepreneurs & VCs to provide detailed examples you can steal. Our goal is to understand product-market fit better than anyone on the planet. Rated one of the world's top startup podcasts.
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Soham co-founded Rubrik by taking what he learned from building Google's data center tech to enterprises desperate for cloud migration. Two quarters later, he hit $1M ARR. And a few years later, a $16B IPO. Soham breaks down why paid pilots beat free trials, how to sell enterprise hardware before it works, and why early customers become your bigges…
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Stéphan bootstrapped AODocs to $55M in revenue and 250 employees without taking a dime of VC money—while competing directly with venture-backed competitors. Starting as a services company in 2012, he spotted the cloud migration wave early and built document management for enterprises moving to Google Workspace. In this episode, Stéphan breaks down …
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Andrew bootstrapped Wrike and grew it from 0 to a $2.2B exit by doing the exact opposite of what every startup book tells you. No pivots. No talking to customers before launch. No narrow niche. Just 17 years of relentless focus on one problem while everyone else was pivoting every 18 months. In this episode, he breaks down exactly why bootstrapping…
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Peter Walker from Carta drops the hard data every founder needs. Based on actual cap table data from 1000s of startups, this Q2 update reveals the brutal new reality. It takes 2+ years to go from seed to A (up from 1.6), you need 3X the revenue you used to, and if you're not AI, you're getting half the attention. But there's good news too—teams are…
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Hedra CEO Michael Lingelbach breaks down how his generative video app went from zero to millions of users and an eight-figure run rate in months — then deliberately slowed down to rebuild a V2 that enterprises would pay for. We dig into the prosumer-to-pro upsell, why free users are a false signal, and how a creator-seeded launch can outpull ad spe…
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Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI. In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He tested co-founders by starting fights. Built in Slack for 10 months before adding a web interface. Kept his team at 8 people …
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Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded. In this episode, Rick reveals how a casual project with zero expectations turned into a billion-dollar business, why early-stage startups should avoid h…
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Neil Patel just flipped everything you know about startups upside down. He says product-market fit is overrated, giving away your software for free can make you rich, and the real secret to scaling isn’t charging customers—it’s monetizing the leads your free product generates. Neil breaks down his playbook on how startups can leverage free products…
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Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months. We go deep on Roy’s playbook for using controversy, virality, and content to get millions of views—and millions in ARR. You’ll learn why Roy intentionally designs content to sp…
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Mary Beth Snodgrass shares the raw and real story behind Healthiby—an innovative healthcare startup that succeeded in delivering measurable health outcomes but ultimately failed commercially. Hear firsthand what went wrong, from unclear payer dynamics and sales friction, to macroeconomic shifts and storytelling gaps. This episode pulls back the cur…
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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 …
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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 …
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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 gro…
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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 e…
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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 …
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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 h…
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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 bein…
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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 i…
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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.…
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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 …
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How do you build a $100B business without hypergrowth or endless funding rounds? Hernan Kazah co-founded Mercado Libre, the Latin American ecommerce giant, at the peak of the dot-com bubble. But when the market crashed, funding disappeared, and competitors doubled down on spending, Mercado Libre focused relentlessly on building a rock-solid, profit…
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Four founders prove you don’t need Silicon Valley, a technical degree, or a massive seed round to build a massive company. We go through the key observations from the last 4 episodes: How Skip created a $200M business in a third tier city, Polarsteps’ NPS‑obsessed rise, Jobber’s decade‑long compounding engine, and why a small decision was key to Pu…
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Jordan Dearsley spent 3 years building a startup stuck at $500K in revenue—then he burned it all down and moved to San Francisco. A year later, he was at $10M ARR. This episode walks through Jordan’s decision to abandon a profitable business, why solving a painful customer problem was the key to explosive growth, and how finding product-market fit …
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Two founders, two wildly different paths to $100M ARR: Arvind Jain, founder of Glean, walked away from a unicorn to start over—raising $15M without revenue and ignoring lean startup rules. Kyle Hanslovan, founder of Huntress, faced brutal rejection, slept in his car, maxed out credit cards, and still crushed it. This episode is packed with raw less…
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Avery Pennarun raised $160M for Tailscale—without even meaning to. What started as a small, simple project exploded into an unstoppable force in network connectivity and security. This episode reveals exactly how Avery turned a tiny seed round into millions of dollars in ARR, powered by nothing more than word-of-mouth and an obsession with solving …
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Description: Jack Kuveke returns to unpack the wildest startup news this month: from billion-dollar frauds and crypto scams, to OpenAI’s secretive $6.5 billion gadget project with Apple’s design legend Jony Ive. We dig into why big-name investors keep missing red flags, and why AI might be crushing entry-level tech jobs faster than anyone expected.…
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After two pivots and nearly running out of runway, Merrill Lutsky found insane growth—scaling Graphite to tens of thousands of daily users and millions in ARR. He reveals exactly how Graphite landed its first massive enterprise customer, doubled revenue overnight by changing pricing, and turned user feedback into momentum. Merrill shares hard-earne…
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Most early-stage founders get trapped in the chaos of endless tasks, there's always too much to do and not enough time. We go through the last 4 episodes to see what how the best founders prioritize. We also see why you can raise millions without real traction but can’t fake product-market fit, how positioning yourself for luck is as important as h…
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Dax built Lightspeed into a $1B ARR public company—even though he bootstrapped for the first 7 years. In this episode, he reveals exactly how he used a 4x pricing shift to create a global reseller machine that grew him to $10M ARR. He also breaks down why obsessing over design and deep customer empathy built the foundation for success.—and how step…
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Carta just released their report for Q1 2025. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices. Carta data shows that graduation rates from Seed to A are as low as they've ever been. Bridge r…
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Kazi Ahmed took a small insight—seeing friends cash out from Amazon brands—and built Carbon6, a software roll-up startup, selling it for $210M just three years later. But behind the quick success was a frantic scramble to survive. Aggressive acquisitions nearly ran them out of cash, forcing a brutal pivot from burning $1M per month to profitability…
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I break down my top insights from recent conversations with four founders who won in unconventional ways. You’ll hear how Noah turned LinkedIn posts into his primary sales channel (without ever going viral), why Dan’s startup survived a brutal 95% downround but ended up at $400M ARR two years later, how Adam turned a stagnant $3M ARR business into …
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Public co-founder Jannick Malling shares exactly how he grew his startup from a tiny beta to millions of users—and hundreds of millions raised. He reveals why fractional shares changed the game for user acquisition, how the company cleverly seized on the GameStop moment to explode growth, and why relentless product focus was critical to scaling qui…
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Corporate spies stealing Slack messages. Adam Neumann raising another $100M (for WeWork 2.0?). AI startups hitting $34B valuations with zero revenue and ordering Ben & Jerry's ice cream over 15 payments with Klarna on DoorDash. April was wild, and Jack Kuveke joins the show to unpack the chaos, controversy, and insanity behind the biggest startup h…
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Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people. In this episode, Forrest shares the brutally honest story behind Jobber’s early days: months of rejecti…
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He turned a personal travel tracker into an app with 10 million users and $10 million in revenue, with almost no funding. He reveals how ignoring conventional startup advice—like launching early, chasing revenue, or partnering for growth—was key to their viral success. He realized everything growth was about word-of-mouth. So the key to success was…
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Jordan Boesch started 7shifts as a teenager helping his dad manage restaurant shifts. Today, his software runs scheduling for 50,000 restaurants. This episode dives into how Jordan bootstrapped early growth, why relentless focus on solving real customer pain mattered more than funding, and how tight partnerships supercharged his expansion. Jordan a…
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Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years. He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots. Fast-forward two years, and he…
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Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable. The difference is in his first startup he was just catering to investors— in his second one only to customers. If you’re an early founder chasing growth, listen to…
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Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves. If you’re raising a pre-seed or seed, Gopi’s tips will make yo…
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Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work. Yet healthcare’s glacial pace, payers, and federal approvals all stand in his way. Hear how he’s testing AI across thousands of patients, fighting for universa…
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Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding. In …
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Dan Park joined Clutch when it was selling 20 cars a month. Then he grew it from $20M in 2019 to $200M in sales by 2022. He was one of Canada's fastest growing companies. Just as he was going to close a $100M round, the macro changed completely. Suddenly, he was left with only six weeks of cash. He was forced to go through a 97% down round at a $15…
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Noah Greenberg grew a content-distribution product from zero to $1M ARR in just one year (and to $4M in 2 years) by focusing on a single channel most founders underrate: LinkedIn. He posted insights daily, highlighted key players in his industry, and made it impossible for prospects not to notice him. In this episode, Noah reveals the exact step-by…
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We break down the real startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard). Forget chasing product-market fit. Start chasing growth, money, and, most of all…
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Wes Bush wrote the original bestseller on Product-Led Growth—and then watched everyone try to copy Dropbox and Slack without truly getting it. Now, he’s here to break down exactly what goes wrong when early-stage founders jump into PLG, how to spot your product’s “million-dollar free problem,” and how to fix the three biggest onboarding gaps that s…
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Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched i…
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One of the most common questions I get is 'How do I know if I have product market fit?" Especially when you're in that gray zone where things are kind of working but they're not really taking off yet, how do you know if you have product-market fit or not? That's exactly what we dive into here. Why you should listen: Why demo to close is an excellen…
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Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI. Then ChatGPT dropped. …
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Jon Yoo’s startup wasn’t working. He pivoted mid-YC, spent five brutal weeks without signing a single customer, and then—right after raising his seed round—his co-founder left. Most startups die right there. Instead, Jon figured out how to land massive customers like FiveTran and Snowflake. He grew from $500K to $2M ARR in 6 months. Why you should …
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