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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How I Raised It - The podcast where we interview startup founders who raised capital.
Foundersuite.com - software for raising capital
Produced by Foundersuite.com, makers of the leading software stack for raising capital: Investor CRM + VC/Angel database + Pitch Deck Hosting + Investor Update tools. Used by startups to raise > $2.5 Billion.
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He grew to millions in ARR in 18 months—by fighting with his co-founders on purpose. | Ross McNairn, Co-Founder of Wordsmith AI.
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49:57Ross 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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Ep. 305 How I Raised It with Nisha Dua of BBG Ventures
44:50
44:50
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44:50Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Nisha Dua of BBG Ventures, a VC fund that invests in “underestimated founders” and founders building a polycult…
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He thought his startup would fail—then grew to $100M ARR. | Rick Song, Co-founder of Persona
59:57
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59:57Rick 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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Forget PMF—Neil Patel says to give your product away for free instead. | Neil Patel, Co-Founder of Neil Patel Digital
31:01
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31:01Neil 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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He got kicked out of Harvard—then grew to $5M ARR in just 3 months. | Roy Lee, Co-Founder of Cluely
52:45
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52:45Roy 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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Ep. 304 How I Raised It with Yoav Oz of Rep AI
36:12
36:12
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36:12Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Yoav Oz, CEO of Rep AI, an ecommerce sales and support chatbot that optimizes every step of the customer journe…
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She raised $1.3M, delivered real value—but still failed. Here’s what happened. | Mary Beth Snodgrass, Founder of Healthiby
24:14
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24:14Mary 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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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
51:20
51:20
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51:20Tanay 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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PMF Observations: Why after PMF, every problem is a people problem.
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18:06We 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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How Mercury Hit $500M ARR—then raised $300M from Sequoia at $3.5B. | Immad Akhund, CEO & Founder of Mercury
54:58
54:58
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54:58Immad 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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Mike Maples: Your Startup Idea Isn’t Crazy Enough—And it's holding you back | Mike Maples, Founder of Floodgate
57:59
57:59
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57:59Ever 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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How he grew to $100M ARR—then exited for $460M. | Zuben Matthews, Founder of Brigit
51:10
51:10
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51:10Zuben 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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He Hit $3.5M ARR and Still Failed. Here’s His #1 Mistake. | Joseph Lee, Founder of Freshline
37:08
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37:08Joseph 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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Ep. 303 How I Raised It with Renata Quintini of Renegade Partners VC
1:01:46
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1:01:46Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Renata Quintini of Renegade Partners, an early stage VC fund that supports companies during the high-stakes pha…
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1st-time founder raises $140M with $0 revenue—grows to 800 employees & profitable. | Andrew Rubin, Founder of Illumio
1:03:29
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1:03:29Andrew 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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PMF Observations: Why it doesn't matter how fast you get to $1M ARR
13:46
13:46
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13:46Forget 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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Ep. 302 How I Raised It with Laura Epstein of Pulse Charter Connect
35:01
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35:01Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Laura Epstein, CEO of Pulse Charter Connect, an organ transport logistics startup that helps move hearts and li…
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He went 7 years with no revenue— then grew to $100M ARR. | Rob Woollen, Co-Founder of Sigma
55:57
55:57
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55:57Rob 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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$10M Raised, 500K Users, but she still failed—here’s what went wrong | Benedetta Lucini, Founder of Oval Money
49:31
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49:31This 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 $100B Mercado Libre got started—& why it almost went bankrupt after 9 months. | Hernan Kazah, Co-Founder Mercado Libre
57:20
57:20
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57:20How 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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PMF Observations: How 4 Founders Built Massive Startups Their Own Way
27:31
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27:31Four 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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His AI Voice Startup grew to $10M ARR in 1 Year—after 3 Years Stuck at $500K | Jordan Dearsley, Founder of Vapi
50:39
50:39
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50:39Jordan 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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Ep. 301 How I Raised It with Marlon Nichols of MaC Venture Capital
41:18
41:18
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41:18Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Marlon Nichols of MaC Venture Capital, a a seed-stage venture capital firm that invests in technology startups …
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WebSummit Panel w/ Founders of Glean ($5B) and Huntress ($2B): What it takes to hit $100M ARR
18:45
18:45
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18:45Two 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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How his $2B startup grew to $10M+ ARR with zero marketing. | Avery Pennarun, Founder of Tailscale
50:31
50:31
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50:31Avery 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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May Startup News: Elizabeth Holmes Returns, Billion-Dollar Frauds, & the End of Tech Jobs w/ Jack Kuveke
28:43
28:43
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28:43Description: 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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He hit $1M ARR in 10 months—after doing of a full, 180 pivot. | Merrill Lutsky, Founder of Graphite
56:30
56:30
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56:30After 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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PMF Observations: Why passion is more important than you think
19:51
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19:51Most 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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He didn't raise VC for the first 7 years— then grew to $1B in ARR. | Dax Dasilva, Founder of Lightspeed
55:15
55:15
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55:15Dax 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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Q1 2025: The Seed to Series A Gap is Wider Than Ever. Here's what to do. | Peter Walker, Head of Insights at Carta
48:22
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48:22Carta 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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He went from 0 to a $210M exit in 3 years—without inventing anything new. | Kazi Ahmed, Founder of Carbon6
45:14
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45:14Kazi 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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Forecasts are overrated—great founders build one step at a time. | PMF Observations
18:06
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18:06I 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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Ep. 300 How I Raised It with Stacy Havener of Havener Capital
48:48
48:48
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48:48Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Stacy Havener of Haver Capital, a a firm that helps asset managers launch and raise funds. In this episode we d…
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He took on Robinhood & built Public.com into a $1B company with $440M raised. | Jannick Malling, Founder of Public.com
55:12
55:12
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55:12Public 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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Adam Neumann Returns, SV Spies, AI Robots Rise | April Startup News w/ Jack Kuveke
39:53
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39:53Corporate 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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1 year in he had just 3 customers—today he’s at $100M ARR. | Forrest Zeisler, Co-Founder of Jobber | Forrest Zeisler, Co-Founder of Jobber
53:13
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53:13Forrest 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 lost 90% of his users overnight—then grew his consumer app to $10M ARR. | Koen Droste, Founder of Polarsteps
46:30
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46:30He 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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He launched a “side-project”— now it’s used by 10% of all restaurants. | Jordan Boesch, Founder of 7Shifts
40:20
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40:20Jordan 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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Ep. 299 How I Raised It with Jed Ng of AngelSchool.vc
43:53
43:53
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43:53Produced by Foundersuite (for startups: www.foundersuite.com) and Fundingstack (for VCs: www.fundingstack.com), "How I Raised It" goes behind the scenes with startup founders and investors who have raised capital.This episode is with with Jed Ng of AngelSchool.vc, an accelerator and training platform for aspiring angel investors. In this episode, w…
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1st-time founder grows AI headshot app from $0 to $10M ARR in 2 years—with no funding. | Wesley Tian, Founder of Aragon
53:26
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53:26Wesley 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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He raised $30M & failed. Then raised $0 & grew to $550M in revenue. Here's what he learned. | Mike Salguero, Founder of Butcherbox
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54:56Mike 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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He invested in 30 early-stage startups. Here's what he looks for in the founders he backs. | Gopi Rangan, Founder of Sure Ventures
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35:57Gopi 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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He raised $300M to prevent heart attacks. Here's how he got his health tech startup off the ground. | Dr. Min, Founder of Cleerly
43:22
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43:22Cardiologist 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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