The Product Market Fit Show

Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data instead of selling, technicians reading manuals instead of fixing. He started Instalily in Spring 2023 when everyone said AI agents were impossible. Instead of replacing workers, he built AI that finds signals in noise—telling each salesperson exactly which deal to focus on right now. The results are insane: $1M ARR within months, tripling revenue year two, delivering $150M+ value to single customers. His secret? While competitors pitched flashy demos, Amit's team attended 100+ trade shows to understand actual operator pain. They hired fresh AI grads who "shipped fearlessly" instead of senior talent stuck in old paradigms.Why You Should Listen:How "operator market fit" beats product market fit for enterprise salesThe GTM playbook that hit $1M ARR in months by attending 100+ trade showsWhy hiring AI-native grads crushed hiring senior talent for AI productsHow focusing on time-to-value unlocked enterprise dealsThe counterintuitive approach: augment the best parts of jobs, not the worstKeywords:startup podcast, startup podcast for founders, Instalily, Amit Shah, AI agents, enterprise sales, operator market fit, B2B SaaS, AI automation, vertical SaaS00:00:00 Intro00:04:42 Leaving 1-800-Flowers00:09:55 Starting when everyone said AI agents were impossible00:11:51 The vision—amplify the best parts of work, not replace the worst00:16:59 Operator market fit over product market fit00:20:48 Landing first $2B enterprise customers 00:29:00 The 100+ trade show GTM strategy that actually worked00:33:02 Why they hired AI-native grads instead of senior talent00:34:51 Hitting $1M ARR in monthsRetrySend me a message to let me know what you think!

Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insurance for Tesla, Toyota, and MasterCard. But the journey was brutal. Wayne worked solo for a year, burning through savings in San Francisco. Flew to South Africa for 7 weeks to land his first insurance partner. The real breakthrough came 4 years later, in 2019, when Elon tweeted about Tesla insurance—instant rocket ship growth. Today Sure is the rails for embedded insurance, like Visa for credit cards.They raised $120M but haven't needed money since 2021 because they've been profitable since their Series B. Why You Should Listen:How to validate an entire business in a weekend. Why he worked solo for a year before raising money or hiring anyone.The exact playbook for pivoting while keeping your old product alive.How one Elon Musk tweet created instant product-market fit.Keywords:startup podcast, startup podcast for founders, Sure, Wayne Slavin, embedded insurance, InsurTech, product validation, bootstrap to profitable, Tesla insurance, B2B pivot00:00:00 Intro00:01:48 The flight to Vegas that sparked a $120M insurance company00:03:03 Building a fake insurance product in one weekend to test demand00:11:00 Working solo for a year while burning through savings00:14:43 Flying to South Africa for 7 weeks to land first insurance partner00:19:58 Convincing 5 friends to quit their jobs00:27:56 Pivoting from mobile app to embedded insurance00:46:03 Elon's tweet creates rocket ship growth overnightSend me a message to let me know what you think!

Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months. His secret? Insane distribution. His formula is to ignore quality—and engineer quantity instead. While everyone obsesses over viral content, Matt posts 1,000 videos across 333 accounts daily, guaranteeing a million views through pure math. No luck required. He applies the same "volume negates luck" philosophy to everything: 15,000 cold emails daily, thousands of Reddit posts to dominate SEO rankings.  Matt reveals the exact Reddit hack to guarantee #1 Google rankings, how AI agents automate everything from account creation to content generation, and why he purposely changes video metadata to trick algorithms at scale. At 23, he's cracked distribution so thoroughly that he can now incubate any business and guarantee its growth.Why You Should Listen:How posting 1,000 videos daily GUARANTEES 1M views The Reddit hack that guarantees #1 Google rankings in 7 daysWhy referral revenue is the only true sign of product-market fitThe "volume negates luck" framework that beats any growth strategyKeywords:startup podcast, startup podcast for founders, Matt Everett, Clover, growth hacking, viral marketing, SEO hacking, distribution strategy, AI automation, bootstrappingChapters:00:00:00 Intro00:01:31 Selling first company at 2000:03:54 Selling second company for $800K in 3 months00:06:37 The 1000 videos per day distribution hack00:24:39 How to guarantee #1 on Google with Reddit posts00:30:52 15,000 cold emails daily—the outbound machine00:47:27 Why 30% referral revenue is true product-market fitSend me a message to let me know what you think!

Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software. Then Russ told investors to pretend the $5M didn't exist and bet on a $200K pipeline instead. That pivot led to 600 Fortune 2000 customers and an exit at $50M ARR. Now building his AI measurement startup Larridin, Russ shares why being a repeat founder creates a different problem—everyone tells you your idea is great even when it's not. His solution? Don't believe anything until someone writes a check.Why You Should Listen:Why he walked away from $5M ARR to pursue a $200K pipeline.How emergent user behavior revealed a $50M business.Why "everyone loving your idea" means nothing.Why finding product-market fit is only step 1.Keywords:startup podcast, startup podcast for founders, Dynamic Signal, Russ Glass, product-market fit, enterprise sales, employee advocacy, pivot strategy, B2B SaaS, influencer marketing00:00:00 Intro00:01:36 30 years of Silicon Valley startups00:03:05 Dynamic Signal's original idea00:07:29 The emergent behavior that changed everything00:15:38 Walking away from $5M ARR to pursue a $200K opportunity00:18:23 Why product-market fit is never final00:22:14 Selling Dynamic Signal 00:24:30 Starting Laridin00:36:34 Raising $17M as a repeat founder—why everyone says yesSend me a message to let me know what you think!

Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up.Then he made two changes—and scaled to $100M in revenue in 2 years. Shopify acquired them for over $2B.Harish says it wasn't about finding product-market fit. It was about finding product-PRICE-market fit. The product was fine. The pricing model was killing them. This episode breaks down why pricing often isn't just a business decision—it's part of your product, how to build self-serve systems that scale to thousands of customers without talking to anyone, and why you must obsess about end users AND economic buyers if you actually want adoption.Harish is now building Augment, an AI company for logistics that just raised an $85M Series A. He shares what he learned shadow-sitting operators for 60 days and why demos mean nothing in the AI era.Why You Should Listen:Why PMF is often not enough—you need  product-price-market fitWhy subtle changes can have huge resultsWhy you need both users AND buyers to love your productHow to master self-serve Keywords:startup podcast, startup podcast for founders, product market fit, pricing strategy, $2B exit, Shopify acquisition, product-price fit, logistics startup, self-serve systems, Amazon fulfillment00:00:00 Intro00:07:06 Starting Deliver in 201700:14:24 Struggling with only 10 customers after 9 months00:19:53 The two changes that changed everything00:23:43 Zero to $100M in 2 years and product-price-market fit00:29:32 How the $2B+ Shopify acquisition happened00:32:07 Starting Augment AI for logistics00:47:35 PMF moments and top advice Send me a message to let me know what you think!

Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A.This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why that strategy fails, and how Dheeraj thinks about building platforms with use cases instead of just features. He explains why the biggest opportunities come from bundling and why you need to hit 130%+ NRR to scale in B2B.Dheeraj also shares the two near-death experiences at Nutanix in the first 5 years, how they survived, and what he's building differently at DevRev in the AI-native world.If you're wondering whether you have real PMF, how to think about platforms vs features, or why your existing customers matter more than new ones—this is mandatory listening from someone who's done it twice at massive scale.Why You Should Listen:Learn why PMF at $1M doesn't mean PMF at $10M—and why you have to find it again at every milestoneWhy "sell and run" kills startups—the real work starts after you close the dealSee how platform thinking (not feature thinking) took Nutanix to $1B ARRUnderstand why 30-40% of revenue from existing customers is real PMF Keywords:startup podcast, startup podcast for founders, product market fit, platform thinking, Nutanix founder, enterprise SaaS, net dollar retention, PMF milestones, fastest to $1B, second-time founder00:00:00 Intro00:01:58 Starting Nutanix00:14:24 Why he left a $20B company00:18:53 The DevRev thesis00:27:39 Pre-AI vs post-AI product strategy and the agent shift00:40:57 Platform vs features00:46:25 PMF is not a destination00:48:10 #1 AdviceSend me a message to let me know what you think!

Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it. When Cursor emailed about their crushing costs, Simon flew to San Francisco unannounced. They migrated their entire workload within a week, cutting their bill by 95%. Then came Notion. Justin pulled 24-hour coding marathons during their POC, fixing 300 milliseconds of latency in three hours. They signed on July 25th—the same day Simon's daughter was born. Now TurboPuffer powers Cursor, Notion, and Linear while staying profitable with just 17 people. Simon shares why he turned down easy Series A money and his framework of exactly 6 legitimate reasons to ever raise capital.Why You Should Listen:The power of making something 10-100x cheaperWhy you need to be willing to fly to early customers (how that landed Cursor)The 6 reasons to raise money (and why you often shouldn't)How working 24-hour sprints during POCs converted enterprise customersWhy staying profitable with 17 people beats raising $30M you don't needKeywords:startup podcast, startup podcast for founders, TurboPuffer, Simon Eskildsen, vector database, Cursor, Notion, bootstrapping, database startup, AI infrastructure00:00:00 Intro00:07:52 Finding the problem00:12:25 Building alone00:22:27 Going viral on X00:26:18 Closing Cursor00:40:17 Closing Notion00:45:26 Why he didn't raise $30M when everyone expected him toSend me a message to let me know what you think!

Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay.Then he figured out the problem: he had product-user fit, but not product-buyer fit. Developers loved Snyk. Security teams (the actual buyers) didn't care about it. The distance between user and buyer was killing him.So Guy spent a year building governance features, reporting, and enterprise capabilities—all the stuff developers didn't care about but security teams needed to write checks. Four months later, Snyk hit $650K ARR. A year after that, $4.5M. Then $19M. Today it's over $300M ARR.This episode breaks down the brutal reality of PLG when your user isn't your buyer, why Guy thinks the worst outcome for a founder is getting stuck (not failing), and how he's now raising $125M for his next company Tessl.If you're building PLG, selling to enterprise, or wondering why your users love you but won't pay—this is required listening.Why You Should Listen:Learn why thousands of users loving your product means nothing if they won't payDiscover the difference between product-user fit and product-buyer fitUnderstand why the worst outcome isn't failure—it's getting stuck in the grey zoneMaster the art of anchoring in the future instead of just filling today's gapsKeywords:startup podcast, startup podcast for founders, product market fit, PLG strategy, product-user fit vs product-buyer fit, developer tools, security startup, enterprise sales, bottoms-up GTM, Snyk founderChapters:(00:00:00) Intro(00:01:37) The first start up :Blaze.io"(00:06:16) The Beginning & Concept of Skyk(00:15:27) Why use Snyk(00:23:41) The Product Led Growth for Snyk(00:33:08) Raising for Snyk(00:38:58) The Beginning & Concept of TESL(00:46:39) Raising for TESL(00:48:52) Finding PMF(00:49:26) One Piece of AdviceSend me a message to let me know what you think!

Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make.But the wildest part? He got Ford to commit in under a year by doing something most founders would never do: he asked for SO MUCH money that only the CEO could approve it. That one move made him "part of the transformational change" instead of a vendor they could ignore.In this episode, Amar breaks down the exact pricing strategy he used to land an 8-figure deal, why founders who sell discounted pricing are sabotaging themselves, and what it actually takes to compete against billion-dollar incumbents like Carta (his current company, Mantle, is doing exactly that).If you're trying to sell to enterprise, wondering if you should bootstrap or raise, or questioning whether your market even exists—this episode will reset how you think about all of it. Amar's built companies in mobile, vehicles, security, and fintech. He knows what works.Why You Should Listen:Learn the pricing trick that got a CEO to sign off to an 8-figure deal.Discover why asking for MORE money (not less) is how you win enterprise dealsWhy getting told "you're nuts" might mean you're dead rightMaster the one metric that matters more than ARR in the early daysKeywords:startup podcast, startup podcast for founders, enterprise sales, 5x founder, product market fit, pricing strategy, Tinder origin story, competing with incumbents, bootstrapping vs raising, SaaS pricingChapters:(00:00:00) Intro(00:03:56) The Start & Finding PMF for Tinder(00:09:04) Xtreme Labs(00:12:18) Autonomic(00:17:03) The Contract Turned Acquisition(00:22:04) The origin of Mantle(00:28:56) Going into a Dominated Category(00:32:39) Raising & Pitching for Mantle(00:40:01) One Piece of AdviceSend me a message to let me know what you think!

Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from scratch using a technology that barely worked.Two years later, Blue J went from $2M to $25M in ARR. They're adding 10 new customers every single day. NPS went from 20 to 84.This isn't a story about getting lucky. It's about a founder who knew—with absolute conviction—that the market would eventually arrive, and made sure he was ready when it did. But it's also about the danger of fooling yourself into thinking you have PMF when you only "kind of have PMF."Why You Should Listen:Learn the brutal difference between fake and real PMFDiscover when to abandon millions in existing ARR to go all-in on something elseWhy "time to value" might be the single most important metric for word-of-mouth.See what it takes to survive until the market is ready.Keywords:startup podcast, startup podcast for founders, product market fit, founder journey, early stage startup, startup pivot, AI startup, SaaS growth, founder advice, hypergrowth startupChapters:(00:02:00) Starting BlueJ(00:9:26) Introducing AI to Tax Research(00:12:44) Starting to Build(00:17:03) Not Having True PMF(00:19:44) Believing in Retrieval Augmented Generation(00:25:34) Updating to V2 of BlueJ(00:30:58) The Necessity of Time to Value(00:33:47) When You Knew You Have PMF(00:38:19) One Piece of AdviceSend me a message to let me know what you think!

Dean thought he'd have to bootstrap Axonius because no investor would fund a solution to a problem that had existed for 20 years. He was wrong—they've raised $500M. The breakthrough came when a Fortune 500 company was actively being hacked by Chinese state actors. Their first customer almost said no—they had 20 bugs during the POC. But Dean's team fixed each one within 48 hours while their competitors took quarters to respond. That speed changed everything. They went from zero to $100M ARR in under 5 years, created an entirely new category (cyber asset management), and achieved an NPS score in the 80s—unheard of in cybersecurity. His framework for the three types of enterprise journeys will change how you think about positioning.Why You Should Listen:Why responding to customer issues in hours changes everything.How to turn a "dormant pain everyone accepts" into a $500M+ company.Why speed beats everything.The 3 types of enterprise software journeys and which one VCs won't fund.Keywords:startup podcast, startup podcast for founders, Axonius, Dean Sysman, cybersecurity startup, enterprise sales, Unit 8200, cyber asset management, B2B SaaS, YC alumni00:00:00 Intro00:02:25 From Hacker to CyberSecurity00:14:46 The three types of enterprise software journeys00:18:41 Why time to value beats everything00:29:33 Thought they'd bootstrap but VCs validated the problem00:35:14 Failed POCs and landing first customer with 20 bugs00:40:10 Zero to $100M ARR in under 5 years00:45:24 When to know you have product-market fitSend me a message to let me know what you think!

Casey  turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on category creation when everyone thought hackers were the enemy. You'll learn about the exact moment he knew he had product-market fit, why he blew every pitch to top VCs until he reframed his vision, and how giving away 500 t-shirts did more for growth than any paid marketing. If you're building a marketplace, creating a category, or just trying to figure out how to explain what you do—this is required listening.Why You Should Listen:Master the 30-second Uber pitch test—Casey's framework for refining your message until anyone gets it.Learn why problem-solution fit without product-market fit is worthless Validate your marketplace with $500 and no codeWhy your network is your only real asset pre-Series AThe surprising ROI of early brand marketing Keywords: startup podcast, startup podcast for founders, marketplace startup, go-to-market strategy, product-market fit, category creation, B2B sales, early-stage fundraising, founder pitch, cybersecurity startup00:00:00 Intro00:01:36 From white label pen testing to the Bugcrowd idea00:18:58 Testing with MailChimp and 5000 hackers signed up00:21:46 Landing Google as customer in month four00:24:24 Blowing every pitch meeting in Silicon Valley00:33:21 The Uber pitch technique for simplifying the message00:36:57 Early go-to-market tactics and hitting $1M00:43:37 Open heart surgery and stepping back as CEOSend me a message to let me know what you think!

Zach spent 8 years at Google leading engineering for Google Docs, then left to build a photo sharing app with zero go-to-market plan. Reality hit hard: "At Google, anything you launch gets millions of users. At a startup, the challenge isn't building—it's getting anyone to care." After writing a brutal postmortem documenting everything that went wrong, he started Warp with strict principles: only hire product-obsessed people, document every process, build pure software not services. For three years, Warp had hundreds of thousands of free users but no revenue. Then they pivoted to AI-powered development in 2024. Here's how they went from taking 300 days to hit their $1M to now adding $1M ARR every 10 days. Why You Should Listen:Why working at Google can set you up to fail as a founderHow to know when to quit your own startupWhy you should write down every operating principle before startingThe shift he made to grow insanely fastWhy competing directly with fast-growing startups is actually smartKeywords:startup podcast, startup podcast for founders, Warp, Zach Lloyd, Google alumni, developer tools, AI coding, product-market fit, startup pivot, Series B00:00:00 Intro00:01:48 From law school to Google via Craigslist00:05:01 Why Google makes you a terrible startup founder00:10:36 Joining SelfMade as technical co-founder00:19:00 Writing a brutal post-mortem of the startup experience00:27:15 Building Warp and getting 10,000 signups day one00:38:08 Raising $50M Series B with zero revenue00:41:50 Pivoting to Agent Mode and AI development00:46:27 From 300 days to $1M to adding $1M every 10 daysRetrySend me a message to let me know what you think!

Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months. Then retail media exploded and everything changed—he went from grinding against the current to riding a wave.After selling to Microsoft, he took 6 months off, got bored, and started Bluefish AI with the same team. This time they called Fortune 500 CMOs before building anything. His #1 advice for early-stage founders: Get on the plane. And go meet your customers. You'll be shocked by how big a difference that makes. Why You Should Listen:How to survive on 2 months of runway indefinitelyHow to validate your next startup before writing any codeWhy second-time founders often have more blind spots than first-timersKeywords:startup podcast, startup podcast for founders, PromoteIQ, Microsoft acquisition, Alex Bluefish, retail media, product-market fit, MarTech, enterprise sales, second-time founder00:00:00 Intro00:01:58 From management consulting dreams to startup world00:04:44 Trying to return $200K to investors after 30 days00:07:19 Pivoting through iterations to find retail media00:12:13 Finding product-market fit like a river reversing00:21:28 Microsoft acquisition with $2,000 in the bank00:24:30 Post-exit sabbatical and starting Bluefish00:35:08 Building for AI marketing with Fortune 500 design partners00:43:12 Always get on the planeSend me a message to let me know what you think!

Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair." Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% right, 10% of B2C customers can end you. He raised from Tiger just as the firm exploded. The DoorDash partnership that seemed like salvation turned into their worst nightmare. But then they pivoted to B2B and saw their average order value grow 5x overnight."Work-life balance is BS. If you can work seven days a week, you'll fail faster, fix faster, and find product-market fit faster."Why You Should Listen:Why just 10% of your customers can destroy your business How to close funding in the middle of a macro crisisWhy work-life balance is BS if you want to build something bigHow stealing another startup's playbook can lead to 5000% growthWhy your worst customers might actually show you your best pivotKeywords:startup podcast, startup podcast for founders, ServiceUp, Brett Carlson, marketplace startup, B2B pivot, Tiger Global, auto repair tech, fleet management, startup growth00:00:00 Intro00:01:40 Failed auto shop becomes ServiceUp idea00:03:27 Pulling co-founder out of retirement00:09:30 Raising $2M seed from angels00:13:23 Building the MVP in Puerto Rico00:15:01 Early Bay Area operations and getting shops00:17:50 The drug dealer death threat incident00:21:17 Tiger Global loses $8B during Series A00:26:57 DoorDash partnership disaster00:28:36 Pivoting from B2C to B2B fleets00:30:00 Finding product-market fitSend me a message to let me know what you think!

Doug spent 3 years building technology before landing real customers. While other startups were growing fast, Ethic was stuck at $5M AUM after two years. Until he found a way to help his customers help them WIN new clients they couldn't land before.That single shift took them to $250M AUM in one year. He reveals why he left investment banking in Australia, sold everything, and moved to the Bay Area within three weeks with no idea what company to start. He pitched over 100 investors to raise early rounds, survived years of building with no traction, and discovered the enterprise sales playbook that unlocked distribution in wealth management. Today Ethic manages $7B and has raised. "If I knew how difficult it would be, maybe I wouldn't have done it." This is the reality of building a decade-long overnight success.Why You Should Listen:Why helping customers win new business is the killer ROIHow to survive a 3-year build phase when everyone else is growing fastWhy you should pitch 100+ investors even if only 5 will say yesHow to figure out distribution and go-to-marketWhy the best value-add investors never pitch their value-addKeywords:startup podcast, startup podcast for founders, Ethic, Douglas Scott, wealth management, ESG investing, fintech, B2B2C, Series A, distribution strategy00:00:00 Intro00:01:47 What Ethic does00:08:15 Leaving Australia for Bay Area with no plan00:17:06 The breakthrough for 5x YoY growth 00:29:42 Three years building with no traction00:38:36 Distribution partnerships unlock growth00:42:44 Finding product-market fitSend me a message to let me know what you think!

Arnold Schwarzenegger mastered three completely different fields—bodybuilding, acting, and politics—with one simple philosophy: reps, reps, reps. This solo episode reveals why speed of execution is the only real moat for early-stage founders. One founder takes an idea from conception to signed customers in three weeks. Another takes six months. They both had equally good ideas, but one got 100 reps in a year while the other got 10. Even Twitter, an established app, became top 5 in the App Store not through one or two big changes but 300 small iterations. Teams naturally slow down over time. You used to ship in days, now it takes months. You have more engineers but move slower. This episode breaks down why this happens and how to maintain that day-one velocity even at $10M ARR. Why You Should Listen:Why speed is the only moat early-stage founders actually haveHow to get 100 reps while your competitor gets 10Why MVPs shouldn't stop after you have a product in marketHow Twitter went top 5 in the App Store with 300 tiny changesWhy teams naturally slow down and how to fight itKeywords:startup podcast, startup podcast for founders, startup speed, MVP strategy, iteration cycles, product development, founder mode, execution velocity, startup growth, early-stage strategy00:00:00 Intro00:00:32 Arnold Schwarzenegger and reps, reps, reps00:02:18 Speed as the only moat for early-stage founders00:03:48 Why founders lose MVP mentality after launch00:09:22 How to stay in Jeff Bezos' day one RetrySend me a message to let me know what you think!

Aviv spent months walking construction sites carrying tools for managers just to understand their problems—speaking to customers is "bullsh*t"—you need to work beside them to see reality. His company Buildots had a working AI product that tracked construction progress perfectly, but 90% of users got zero value from it. Until he made one key change that took them from barely surviving to 3-4X yearly growth. He reveals why his first customers had negative margins, how he accidentally underpriced by 10X, and why you should never build a feature until you've proven the value manually in Excel first. After nearly dying, today Buildots does tens of millions in revenue.Why You Should Listen:Why you need to stop talking to customers and start working alongside them.Why one simple change can transform usage and value creation.Why you should prove value without product before writing a single line of code.How to price when you have no idea.Keywords:startup podcast, startup podcast for founders, Buildots, Aviv Leibovici, construction tech, customer development, product-market fit, B2B SaaS, computer vision,00:00:00 Intro00:01:41 From Israeli intelligence to construction tech00:05:03 Working alongside construction managers00:10:20 Understanding the problem00:21:41 First customer deployment disaster00:30:29 COVID and nearly failing00:39:04 The pivot that changed everything00:45:16 Finding product-market fitSend me a message to let me know what you think!

Shensi cold messaged 50,000 engineers to build Merge. She worked 9am-9pm every day, gave her first customers two months free to prove herself, and refused to hire anyone remote—even during peak COVID. She purposefully didn't collect a single dollar of revenue until she knew she could hit $1M in a months. "Startups are all about momentum." She lost their biggest deal to a competitor who copied them, then won that customer back years later. She outbounded her way from zero to $10M through sheer force of will, doing demos all day until her calendar was completely booked. Today Merge has raised $75M and powers integrations for hundreds of B2B companies. This is raw, unfiltered founder advice from someone who believes you just have to "man up" and outbound your way to success.Why You Should Listen:Why you should wait to collect revenue until you see a clear path to $1M ARR. Why you need to outbound thousands of people to build your team.You can will your way to $10M—but you'll need something else to hit $100M.Why they are an in-office company, even for remote rockstar devs.Keywords:Startup podcast, Startup podcast for founders, Merge, Shensi Ding, integrations, B2B SaaS, outbound sales, seed funding, product-market fit, API, developer tools, startup growth00:00:00 Intro00:02:55 From coding in middle school to investment banking00:06:45 How she found the problem00:09:09 100 customer conversations00:13:51 Quitting during COVID00:16:16 Raising $4.5M seed in 3 weeks00:21:01 Outbounding 50,000 engineers00:25:32 Landing first customers through cold LinkedIn00:31:37 Not collecting revenue on purpose00:37:47 When product-market fit actually hitSend me a message to let me know what you think!

Eldon put a $150K line of credit on his house to start eSentire in 2001. No VCs would touch him—they didn't understand services businesses. He worked 12-hour days, 7 days a week for 7 years to hit $1M in revenue. His co-founder coded while he flew to New York on $99 JetBlue flights from Buffalo to save money. Then something clicked: they brought in an experienced CEO who transformed their scrappy cybersecurity consulting into a managed service. Revenue grew from $1M to $10M in just 3 years. They won 95% of competitive deals against Dell-backed SecureWorks by comparing themselves to a local burger joint versus McDonald's. Today eSentire is worth over a billion dollars. This is the raw, unfiltered story of building a massive B2B company without following any of the Silicon Valley playbook—no YC, no venture capital for years, just pure survival mode.Why You Should Listen:How to win head-to-head sales battles against bigger competitors with no marketing budget.Why taking a long time to hit $1M ARR doesn't mean failure.How bringing in an experienced CEO after 8 years saved the company.Keywords (comma-separated):Startup podcast, Startup podcast for founders, eSentire, Eldon Sprickerhoff, cybersecurity, bootstrapping, managed services, B2B sales, Canadian startup, MSSP, founder-led sales, pivot00:00:00 Intro00:01:00 Starting eSentire after 9/1100:03:26 The dot-com crash reality00:05:23 $150K home equity line to start00:08:32 Landing first customer at ING00:14:03 Making up the rules as they went00:19:09 Bringing in an experienced CEO00:22:44 The hamburger pitch that beat Dell00:28:36 From $1M to $10M in 3 years00:34:39 Common founder mistakes00:40:39 Chief survival officer mindsetSend me a message to let me know what you think!

Soham spent 6 months building AI that would auto-generate integrations between any software. He locked down Glean as an early customer because he had friends there. And it failed completely.So he pivoted. This time, he refused to work with friendly customers who knew him. Instead, he did 10-20 calls per day with strangers who would tell him his product sucked. He posted on Discord communities at 3am, wrote technical blogs that went viral on Reddit, and created fake landing pages to see what integrations people actually wanted. In one year, Composio grew to 100,000 developers and raised $30M from Lightspeed in just 3 weeks. His contrarian take: in AI, asking users what they want will just get you faster horses. Built it instead, and watch their eyes light up.Why You Should Listen:Why friendly customers will kill your startup.The 20  calls per day strategy that scaled Composio to 100,000 users.Why you can't validate AI products by asking.The exact Discord and SEO tactics that got their first thousand users without spending on adsKeywords (comma-separated):The PMF Show is a startup podcast. The Product Market Fit Show is a startup podcast. Startup Podcast, Composio, Soham Ganatra, AI agents, developer tools, pivot, Series A, Lightspeed, integrations, API, tool calling00:00:00 Intro00:06:44 Playing with GPT-2 before ChatGPT00:12:37 Leaving his job to start Composio00:21:16 Pivoting to integrations for AI agents00:28:42 Why friendly customers are dangerous00:31:01 Getting first users through viral content00:36:01 Taking 10-20 customer calls per day00:40:58 Scaling from 1,000 to 100,000 developers00:43:58 MCP and the explosion of growth00:48:59 Raising $30M from Lightspeed in 3 weeksSend me a message to let me know what you think!

Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and watched their business implode. So they fired everyone, moved back to their parents' homes, and spent months cold-calling dentists and lawn care companies to find a real problem. What they discovered: 80% of SMBs still use community banks from 1995. Now Affiniti has 2,000 customers, $10M ARR run rate, and just raised $17M by partnering with trade associations to acquire customers at 25% the cost of traditional fintech. This is the raw story of teenage founders who got punched in the face by Silicon Valley and came back swinging.Why You Should Listen:How getting destroyed on TechCrunch at 18 and subpoenaed by the government led to a $3M revenue pivot in 12 monthsWhy going back to square 0 is often the best moveThe trade association go-to-market strategy that worked for SMB.Why 200 VC rejections and raising $6M in peak 2021 couldn't save their first startup—but taught them everything they needed to know.Get comfortable with bad days—stoicism is the only way to survive.Keywords:Affiniti, Sahil Phadnis, SMB fintech, startup pivot, Y Combinator, teenage founders, Series A, B2B payments, startup failure, trade associations00:00:00 Intro00:01:50 COVID existential crisis at 1600:08:36 Building websites for restaurants00:11:11 Meeting Aaron on Instagram00:15:17 200 VC rejections then raising $6M00:23:03 Getting called a fraud on TechCrunch00:29:15 Firing everyone and moving home00:31:16 Faking toothaches to research SMBs00:40:50 Launching Affiniti00:47:00 The trade association growth hack00:55:03 Raising Series A in 3 weeks00:58:30 Stoicism and bad daysSend me a message to let me know what you think!

Jon spent 3 years building Gamma with barely any traction—just a few hundred users after burning millions. Then ChatGPT dropped. In desperation, he pivoted to AI-powered presentations in March 2023 with one year of runway left. What happened next was insane: Paul Graham publicly mocked their launch tweet calling it worthless—then it went viral. They went from 2,000 signups a day to 60,000. Their servers crashed for three days, but when they came back online, panicked users threw $50K at them thinking they needed to pay to make it work. Within two months of launching payments, they hit $1M ARR and became cashflow positive. This is the raw story of how a dying startup caught the AI lightning and never looked back.Why You Should Listen:How to survive 3 years with no traction.Why 80% hype and 20% value can still build a real business The exact onboarding flow that turned 5% activation into viral growthHow negative viral engagement can still drive massive revenueThe difference between 10x better and 50% betterKeywords:Gamma, Jon Noronha, AI presentations, product market fit, pivot to AI, viral growth, Paul Graham, ChatGPT, cashflow positive, productivity startup00:00:00 Intro00:02:15 Why presentations haven't changed in 40 years00:11:55 User research reveals the real problem00:26:26 The market crashes and runway shrinks00:34:32 ChatGPT drops and everything changes00:43:19 Paul Graham trashes the launch tweet00:48:59 Going viral by accident00:51:33 60,000 signups a day breaks everything00:55:07 Hitting $1M ARR in 2 months00:58:47 Endurance is everythingSend me a message to let me know what you think!

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 biggest champions when you solve real pain. Now building WisdomAI after watching the ChatGPT moment unfold, he shares what's different about competing in AI's gold rush versus owning an ignored category.Why You Should Listen:Why early customers  endure broken productsHow he hit $1M ARR in 2 quarters selling enterprise hardwareWhy you should always charge for pilotsCustomer feedback is the only PMF signal that mattersKeywords:Rubrik, Soham Mazumdar, enterprise sales, data backup, IPO, product market fit, B2B SaaS, cloud migration, WisdomAI, data centers00:00:00 Intro00:04:26 Leaving Google to start a company00:11:00 Building the founding team00:14:27 Landing the first customer in Australia00:22:30 Hitting $1M ARR in two quarters00:25:42 Go-to-market strategy and the DeLorean stunt00:30:30 When Arvind left to start Glean00:34:10 Starting WisdomAI after the ChatGPT moment00:51:22 Advice for early stage foundersRetryClaude can make mistakes. Please double-check responses.Send me a message to let me know what you think!

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 why doubling every two years beats hypergrowth, how to win enterprise deals with zero funding, and why touching business-critical documents means year-long sales cycles but 10-year retention. This is the anti-Silicon Valley playbook that actually works.Why You Should Listen:Why the founder must personally close every single deal in 0 to 1How doubling every 2 years (not every year) creates a more stable businessThe brutal reality of enterprise POCs: doing it for free before getting paidWhy you can't have both fast customer acquisition and high retentionHow being French/European became an advantage against US competitors KeywordsAODocs, bootstrapping, Stéphan Donzé, enterprise sales, document management, SaaS, Google Workspace, cloud migration, product market fit, B2B00:00:00 Intro00:01:12 Bootstrapping vs VC backed00:03:44 From services to SaaS00:19:08 Landing the first customer 00:20:47 Why they turned down VC money00:25:32 The 997 grind—four days on-site with customers every week00:35:21 Why you can't have fast sales and high retention00:40:33 Product-market fitSend me a message to let me know what you think!

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 saved his company (and why VC would have killed it), why he ignored customer development and just built in a bunker, and how manning the support phones himself became his secret product development weapon. Now building Zencoder (AI coding agents), he shares why the future isn't about replacing developers but making every human "superhuman" at their job. This is mandatory listening for any founder questioning conventional startup wisdom.Why You Should Listen:Grew to $2.2B with no pivots for 17 years while competitors kept "failing fast"How he doubled revenue every year from $0 to $100M+ ARRWhy manning support phones himself was better than any customer development processWhy copycats helped Wrike grow fasterThe future of AI agentsKeywords:Wrike, Andrew Filev, bootstrapping, 2 billion exit, product market fit, SaaS, Zencoder, AI coding agents, no pivot strategy, collaboration software00:00:00 Intro00:03:30 Moving to Silicon Valley from Russia to build for millions00:10:06 Going all-in after previous side projects failed00:11:27 Why he never pivoted once in 17 years00:18:47 Launching without talking to customers first00:24:12 Manning support phones and discovering the real roadmap00:29:01 When Microsoft Project, Basecamp, and Jira were the competition00:34:31 The only job definition—double the business every year00:54:16 Why Developers won't be replaced, and become superhuman01:01:57 The $2.2B exit and making employees' dreams come true01:04:36 Finding product-market fit at Zencoder vs Wrike01:06:55 Focus on people—everything traces back to themSend me a message to let me know what you think!

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 finally getting leaner, exits are picking back up, and the worst of the funding winter might be behind us. If you're raising in 2025, this is your reality check.Why You Should Listen:$3M ARR is the new Series A bar—& it takes 1 in 4 founders 3.5+ years to get thereHalf as many seed deals are getting done but at 20% higher valuations—you're either in the AI club or you're outFounders own just 56% after their first priced round and only 10% by Series D—every round costs more than you thinkKeywords:Carta data, Series A requirements, startup fundraising 2025, seed to Series A timeline, ARR benchmarks, AI startup valuations, bridge rounds, founder dilution, startup team size, venture capital trendsSend me a message to let me know what you think!

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 spend. Michael shares the GTM that signs enterprise contracts every few days with no outbound, the exact moment he killed feature churn to ship a real workflow, and what to hire (and fire) in the first 10 people. If you're building AI or any early product, this is a must-listen blueprint on getting from hype to revenue.Why You Should ListenHow Hedra hit an 8-figure run rate in months — with a prosumer → enterprise wedgeThe “free user” trap: why signups ≠ demand and how to price for painWhen to pause growth to build V2 that actually sells (workflow > tech demo)A creator-led launch playbook that drives virality without paid influencersHiring early: bring in a talent lead fast, staff for speed, survive co-founder changesKeywordsAI video, generative AI, product market fit, Hedra, Michael Lingelbach, creator tools, PLG, enterprise SaaS, go to market, startup growth00:00:00 Intro00:02:25 Why he built his own proprietary models00:10:19 Target use cases faceless channels marketers podcasts00:15:31 Early hiring lessons00:38:00 Free vs paid00:51:03 V2 launch and shift to enterprise 00:53:46 Hitting eight figure run rate and scaling GTMSend me a message to let me know what you think!

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 while competitors hired dozens. This episode breaks down his exact playbook: how to test co-founders before committing, why attacking someone's core job kills your sales cycle, and how he accidentally created the hottest seed round by ghosting every VC. Plus the reality of building a rocket ship with a newborn at home.Why You Should Listen:Why starting fights with co-founders can be a great way to test conflict.Why keeping your team at 8 people until PMF lets you move fasterThe accidental fundraising playbook that made VCs go crazyHow having a baby forces you to be 10x more productive as a founderKeywords:Wordsmith AI, Ross McNairn, AI legal tech, product market fit, co-founder selection, Series A, Index Ventures, Slack integration, startup pivots, legal AI00:00:00 - Intro00:01:31 - From Lawyer to CTO00:03:45 - Starting Wordsmith AI00:06:41 - Testing Co-Founder Relationships00:14:42 - Building the MVP00:20:44 - First Product Iterations00:26:39 - Finding Product Market Fit Through Slack00:37:42 - Go-to-Market Using Webinars and Influencers00:47:00 - Balancing Startup Life with a 10-Month-Old BabySend me a message to let me know what you think!

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 hyper-optimization, and the secrets he learned at Square about identity fraud that became his breakthrough. If you want to challenge the typical startup narrative, this one's a must-listen.Why You Should ListenHow Rick Song took Persona from $0 to $100M ARR without believing in product-market fit.Why obsessing over optimization might be killing your startup.How to think differently about fundraising—Rick raised $2.4M without even trying.The real truth about what decisions actually matter in your early days.Keywordsproduct market fit, startup advice, early-stage founders, fundraising, hyper-optimization, identity fraud, Persona, Rick Song, Square, founder mindset00:00:00 Intro00:08:07 Finding Persona's First Customer00:17:56 How to Quit a Successful Job for a Risky Startup00:26:54 Early Product Strategy00:37:40 Hiring the First Employees Without Selling the Dream00:47:54 Fundraising Without Even Trying00:56:55 Hyper-Optimization is Hurting Your Startup DecisionsSend me a message to let me know what you think!

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 to grow exponentially, why your churn doesn't matter if you monetize correctly, and the reality about brand building that most founders completely miss. This episode challenges conventional startup wisdom and reveals a totally different way to think about building billion-dollar businesses.Why You Should ListenWhy Neil Patel thinks chasing product-market fit is a waste of your time.How offering your software for free can create a viral growth engine.How to monetize without charging for your product.Why branding matters, but why you'll have to wait 10 years to feel it.KeywordsNeil Patel, product market fit, SaaS growth, freemium model, lead generation, churn reduction, monetization strategy, startup branding, digital marketing, SaaS startups00:00:00 Intro00:07:05 The Secret Math Behind Giving Software Away for Free00:21:32 How Free Software Can Disrupt Billion-Dollar Industries00:26:26 The Truth About Branding (and Why It Takes 10 Years)00:29:59 Neil's Final Advice to Early-Stage FoundersSend me a message to let me know what you think!

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 spark outrage, how he leveraged Twitter to raise millions from top VCs within 24 hours, and his tactical advice for mastering the short-form algorithms that dominate attention today. If you want an unfair advantage to scale your startup, this is a must-listen.Why You Should ListenHow Roy Lee mastered viral marketing to scale from 0 to $5M ARR in 3 months.Why controversy and shock value are the ultimate distribution hacks.Exactly how Roy raised $5M in 24 hours by leveraging Twitter virality.Why short-form content is the most underrated growth channel for startups today.The secret to X/Twitter's algorithm.KeywordsRoy Lee, Cluely, viral marketing, startup growth, product market fit, AI startup, raising venture capital, short-form content, going viral, Twitter strategy00:00:00 Intro00:02:20 Getting Kicked Out of Harvard and Columbia00:10:31 How Roy Engineered His Viral Moment00:17:23 Launching Cluely and Hitting $5M ARR in 3 Months00:20:49 Secrets to Mastering the Twitter Algorithm00:28:21 The Formula Behind Virality00:38:31 Leveraging TikTok, Instagram, and an Army of Creators00:44:06 Retention Challenges and Future Product Vision00:50:50 Roy's Advice for Early-Stage FoundersSend me a message to let me know what you think!

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 curtain on why having a working product isn't enough and why mastering the market dynamics is crucial to your startup's survival.Why You Should ListenLearn why even successful products can fail if the payer isn't clearly defined.Understand the hidden hurdles in long sales cycles.Discover why storytelling and personal founder journeys are key.See how market timing and macro changes can dramatically impact your startup's trajectory.Avoid the pitfalls of focusing solely on solving problems without a robust go-to-market strategy.Keywordsproduct market fit, healthcare startups, startup failure, go-to-market strategy, founder advice, chronic conditions, startup storytelling, B2B sales, health tech, behavior change00:00:00 Intro00:03:04 Pivoting Fast00:06:16 Finding Initial Users00:08:53 Building a Behavior Change Product00:13:55 Why We Failed00:17:48 Navigating Complex Sales Models00:19:56 Key Lessons00:22:45 Final Advice for Early Stage FoundersSend me a message to let me know what you think!

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 ListenHow 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 AIThe one thing Tanay wishes he'd known about building a startup team five years ago.Keywordsproduct market fit, AI startup, Wispr Flow, Tanay Kothari, founder stories, startup pivot, voice interface, building teams, hyper-growth startup, deep tech startup00:00:00 Intro00:07:22 Learning to Code in Secret00:13:27 From New Delhi to Stanford and Silicon Valley00:17:34 Feather X—Tanay's First Big Startup Exit00:24:33 The Original Moonshot Vision of Wispr AI00:31:19 Why Wispr AI Had to Pivot00:38:32 The Power of Incremental Change Over Radical Shifts00:43:00 Achieving Explosive Growth and True Product-Market Fit00:49:01 The Most Important Lesson—Building the Right TeamSend me a message to let me know what you think!

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 ListenDiscover the #1 reason your startup's growth might be stallingLearn why staying hands-on with sales longer accelerates finding PMFFind 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.Keywordsproduct market fit, startup hiring, startup growth, founder lessons, free business model, early stage sales, team building, radical differentiation, founder mistakes, scaling startups00:00:00 Intro00:04:21 Every Startup Problem is Actually a People Problem00:05:56 How to Identify Great Talent Without Hiring00:07:10 Why Founders Should Stay in Sales Longer00:09:35 Subtle Details are The Key to True Product Market Fit00:12:24 Zeffy and the Hidden Power of Being Radically Different00:17:00 The ROI of Being Uniquely DifferentSend me a message to let me know what you think!

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 ListenHow Mercury went from $0 to $1M ARR in just 5 monthsHow Mercury leveraged Twitter to explode user growth at launchWhy building with zero users might be your secret advantageWhy Immad believes defining company culture at employee #4 was critical to hitting $500M in revenueKeywordsMercury, Sequoia, Immad Akhund, startup fundraising, fintech startup, product market fit, neobank, early-stage growth, Y Combinator, banking as a service, startup culture00:00:00 Intro00:09:23 How Immad Validated the Idea for Mercury00:17:53 Why Immad Turned Down VC to Start Another Company00:28:11 How Immad Raised a $6M Seed Round Before Writing Any Code00:36:08 Launching Mercury and Going Viral on Twitter00:47:08 Knowing You Have Product Market Fit00:51:48 Raising a $20M Series A Just 3 Weeks After Launch00:53:10 The Importance of Defining Your Culture EarlySend me a message to let me know what you think!

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 ListenHow 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.Keywordsproduct market fit, startup ideas, breakthrough startups, seed funding, Mike Maples, lean startup, inflection points, AI startups, zero to one, startup growth00:00:00 Intro00:04:12 The Real Reason “Pattern Breakers” Win00:12:00 Stop Finding Problems Start Living in the Future00:21:23 Why Most Founders Play the Wrong Game00:31:01 How to Know You're Actually in the Future00:36:38 The Hidden Cost of Raising Too Much Money00:46:20 The True Purpose of Your First Million in ARR00:50:58 Three Tests to Know You've Found Product Market FitSend me a message to let me know what you think!

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 ListenHow 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.Keywordsfintech, overdraft fees, product market fit, earned wage access, early stage startups, customer validation, fundraising, founder stories, lending, unit economics00:00:00 Intro00:08:47 Inside the Hidden Overdraft Market00:16:34 Validating Your Idea the Right Way00:27:37 How Brigit Cracked Customer Acquisition00:33:38 Why Unit Economics Saved Us00:37:08 Navigating a Crisis and Coming Out Stronger00:45:14 Behind the Scenes of a $460 Million Acquisition00:48:57 The Moment of True Product Market Fit00:50:22 Advice Every Early-Stage Founder NeedsSend me a message to let me know what you think!

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 ListenHow a $3.5M startup stalled despite tractionHard lessons on finding the right marketThe hidden traps of marketplacesWhy staying gritty isn't always enoughPainkillers vs. Vitamins Rethinking Startup AdviceKeywordsmarketplace, product market fit, startup failure, raising capital, entrepreneurship, founder advice, traction, B2B SaaS, early-stage startup, growth challenges00:00:00 Intro00:04:10 Crashing the Boston Seafood Expo00:08:25 From Shopify to Marketplace00:12:40 Door-to-Door Fish Sales00:17:55 Hidden Risks of Marketplace Models00:23:05 Cracks Emerge at $3.5M Revenue00:26:45 COVID Hits and the Pivot Begins00:30:50 Why Market Matters More Than Grit00:32:55 Rethinking Painkillers vs Vitamins00:35:30 Staying Alive Long Enough to WinSend me a message to let me know what you think!

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 ListenDiscover 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 playbook00:00:00 Intro00:02:47 Carbon6's $210M Exit—Roll-ups and Serendipity00:04:27 Lightspeed's Unplanned Journey to $1B00:06:04 Graphite's Pivots—How a Failed Idea Led to Success00:07:27 Vapi's Rapid Rise After Three Years of Flat Growth00:08:55 Why There's No Single Path to Product Market Fit00:11:19 The Million-Dollar ARR MythSend me a message to let me know what you think!

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 ListenHow to raise $40M in 6 months with no product or revenueWhy “too early” often means bankrupt—and how to avoid itWhy activity ≠ funding (and what to do instead)The hard truth about selling enterprise earlyWhy market timing matters more than product geniusKeywordsproduct market fit, fundraising, early-stage startups, startup fundraising, venture capital, enterprise sales, market timing, Andrew Rubin, Illumio, cybersecurity00:00:00 Intro00:08:15 Why Being Early Can Bankrupt You00:16:09 Creating a Market That Doesn't Exist00:27:55 Activity Does Not Equal Funding00:38:06 Landing the First Enterprise Customer00:49:57 Surviving Enterprise Sales Cycles00:54:56 Navigating the Emotional Rollercoaster01:00:46 The Truth About Product Market Fit01:01:55 Andrew Rubin's Best Advice for Early FoundersSend me a message to let me know what you think!

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 ListenHow 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.Keywordsproduct-market fit, Sigma Computing, pivot, startup growth, business intelligence, Snowflake, early-stage startup, SaaS growth, cloud analytics, founder stories00:00:00 Intro00:02:49 Debating speed to product–market fit00:10:14 Quitting Salesforce and the EIR leap00:23:12 Two years of prototypes that went nowhere00:36:53 The Snowflake meeting and spreadsheet pivot00:45:41 Dealing with Investors00:52:30 Tripling three years straight to $100M ARR00:54:46 Why most people shouldn't start a companySend me a message to let me know what you think!

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 ListenDiscover 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.Keywordsstartup failure, fundraising mistakes, fintech startup, founder lessons, corporate VC, startup partnerships, product validation, founder equity split, early-stage fundraising, startup growth challenges00:00:00 Early Days at Uber and Moving into Fintech00:07:00 Launching a Consumer Fintech App in Europe00:13:37 Validating Without Tech Building an MVP by Hand00:19:22 Why US Startup Models Don't Work in Europe00:23:07 Raising Money Quickly—and the Hidden Costs00:28:56 Running Out of Cash When COVID Hit00:32:15 Tough Decisions Layoffs, Sales, and Shutdown00:37:53 How Big Partnerships Can Sink Your Startup00:43:41 Staying Optimistic Even When Everything Falls Apart00:46:38 Crucial Fundraising Advice for Early-Stage FoundersSend me a message to let me know what you think!

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, profitable core product—ignoring pressure to chase faster growth. Hernan shares how they turned extreme constraints into a secret weapon, why getting profitable early was a game-changer, and why the biggest businesses are built by doing fewer things, better.Why You Should ListenHow Mercado Libre survived going bankrupt by pivoting overnight.Why most startups die chasing growth—and what to do instead.How to build unstoppable momentum by nailing one thing first.The simple test to know if your startup has real product-market fit.The one thing all $100B companies do differently.KeywordsMercado Libre, product market fit, Hernan Kazah, startup advice, ecommerce growth, marketplace strategy, profitability, venture capital, early-stage startups, Latin America startups00:00:00 Intro00:04:07 Why We Chose the eBay Model00:08:56 The Early Hack That Got Us Our First Users00:14:23 Raising Money at the Worst Possible Time00:21:37 Becoming Profitable and Going Public00:26:34 How Mercado Libre Stayed Patient While Competitors Chased Growth00:34:05 Why We Expanded Across Latin America From Day One00:45:11 Our Secret to Winning Against Better-Funded Competitors00:50:04 The Most Important Advice for Early-Stage Founders00:52:16 Why AI is Different From the Internet and Mobile RevolutionsSend me a message to let me know what you think!

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 Public.com's huge success. You'll learn when to ignore best practices, how to choose one north‑star metric, and why slow, relentless improvement beats silver‑bullet fantasies. Perfect fuel for scrappy founders hunting product–market fit.Why You Should ListenThe single‑metric focus that took a travel app to $10M ARR through CovidTurning six months of “no's” into $100M ARR: the slow‑burn playbookWhy mastering your craft first can unlock your next billion‑dollar ideaPicking the rules to break: using “unconventional” as an unfair advantage00:00:00 Intro00:01:30 Why location odds matter less than you think00:02:50 Skip the Dishes proves huge wins can start in tiny markets00:05:30 Polarsteps shows what happens when one metric rules them all00:09:00 Jobber's decade‑long slow burn to compounding growth00:14:40 Public.com and the power of diving deep into your craft00:21:40 The real skill: knowing when to ignore conventional wisdom00:24:30 Key takeaways and next steps for your own playbookSend me a message to let me know what you think!

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 is as simple—and as brutally difficult—as discovering a 10/10 burning pain. If you're a founder struggling to find breakout growth, this episode is your blueprint.Why You Should ListenHow to pivot from a dead-end idea to $10M ARR in one year.The power of solving a 10/10 burning pain.When customer anger becomes your biggest growth signal.Why chasing local maxima can trap your startup.How true conviction unlocks explosive growth.Keywordsproduct-market fit, startup pivot, explosive growth, voice AI, founder stories, SaaS startups, early-stage startups, customer pain points, San Francisco startups, developer tools00:00:00 Intro00:02:35 Stuck at $500K ARR & Burning the Boats00:07:15 Knowing When It's Time to Quit00:08:49 The Side Project that Became Vapi00:16:28 Early Growth and Finding First Customers00:23:32 The Product Hunt Launch that 3X'd Growth00:27:57 Surviving Explosive Growth00:35:17 Competing Against OpenAI and Big Tech00:41:26 How to Identify a True 10/10 Pain00:48:53 The Moment of Real Product-Market FitSend me a message to let me know what you think!

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 lessons on fundraising, product-market fit, and why relentless hustle alone won't save you. If you're a founder chasing growth, stop everything and listen.Why You Should ListenLearn exactly what top founders did to get from zero to $100M ARRWhy chasing perfection won't work (and how to stop)The secret to surviving brutal fundraising rejections (over 60 VCs said no to Kyle)Why hustle culture isn't enough—here's what matters moreKeywordsproduct-market fit, startup fundraising, unicorn startups, founder hustle, lean startup method, scaling startups, early-stage growth, AI startups, SaaS growth, venture capital adviceChapters(00:00:00) Intro(00:02:05) Quitting a Unicorn to Start Again(00:05:09) From NSA Hacker to Startup Founder(00:09:18) Ignoring the Lean Startup(00:12:59) Knowing When to Launch(00:16:32) Finding Product Market Fit(00:18:01) Final Advice for FoundersSend me a message to let me know what you think!

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 everyday developer headaches. Learn why your startup idea is probably wrong (and why that's okay), how Tailscale found explosive product-market fit, and why the biggest opportunities are hiding in the “smallest” problems. If you're an early-stage founder looking for practical insights, game-changing growth hacks, and lessons from someone who's been through it all, this is the episode you can't miss.Why You Should ListenLearn how Avery grew Tailscale from zero to millions in revenue purely through word-of-mouth.Discover why chasing enterprise deals too early might actually slow you down.Find out why solving “small, simple” problems can lead to billion-dollar outcomes.Hear the counterintuitive reason why your product failing early users is actually a huge advantage.Understand how Tailscale turned COVID lockdown into an explosive growth opportunity.Podcast Keywordsproduct market fit, startup growth, product-led growth, Tailscale, word-of-mouth growth, startup fundraising, developer tools, network security, B2B SaaS, early-stage founder advice(00:00:00) How Tailscale Raised $160M Without Chasing Investors(00:01:48) Building a Billion-Dollar Idea From Scratch(00:05:18) How to Find Real Problems Worth Solving(00:13:14) Landing the Critical First Customer(00:22:25) Why Great Founders Start Small, Not Big(00:28:33) Turning Bottom-Up Adoption into Enterprise Deals(00:36:55) Growing from Zero to $1M+ ARR Through Word-of-Mouth(00:46:16) When Avery Knew Tailscale Had Product Market Fit(00:48:27) Avery's Most Important Advice for Early-Stage FoundersSend me a message to let me know what you think!

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. Keywordsstartup scams, OpenAI Johnny Ive, Elizabeth Holmes, Builder AI scandal, tech IPO crash, AI job loss, crypto meme coin fraud, venture capital news, tech layoffs, Theranos lessonsSend me a message to let me know what you think!

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-earned lessons on recognizing true product-market fit, leveraging internal tools as a market wedge, and surviving the chaos every early-stage founder faces. If you're building, pivoting, or scaling your startup, this is a must-listen episode.Why You Should ListenHow to Know When It's Time to Pivot—or Keep GoingLanding Your First Enterprise Deal (and Getting to $1M ARR in 10 Months)Why Daily User Feedback is a Secret WeaponFinding the Real “Must-Have” ProductWhy Your First Pricing Model Probably Won't Work (and How to Fix It)Keywordsproduct market fit, developer tools, pivot, enterprise sales, startup growth, code review, pricing strategy, software startups, founder lessons, Graphite dev tool00:00:00 Raising a seed round on Airbnb Wi‑Fi00:10:40 Lessons from the first failed DevTool00:16:00 Why daily‑use products win00:24:30 Pivoting from mobile rollbacks to code review00:31:00 Ex‑Meta engineers spark a viral wait‑list00:40:00 Switching on pricing and racing to $1 M ARR00:48:30 The pricing tweak that doubled revenue00:50:00 Surviving outages, bank collapses and chaos00:52:30 Co‑founder trust makes or breaks startupsSend me a message to let me know what you think!

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 having a plan, why slow initial growth might be your secret weapon, and how true passion gives you staying power. Why You Should ListenHow to prioritize ruthlessly—focus is about saying no.Why you can't game product-market fit.Turning random luck into edge.When slow growth still winsWhy true founder-market fit keeps you in the game longer.Keywordsproduct-market fit, founder-market fit, startup prioritization, fundraising strategies, early-stage startups, growth strategies, startup pivot, founder lessons, bootstrapping startups, AI startups00:00 Intro02:58 Why Founders Need to Drop Some Balls 05:04 You Can Fake Fundraising but Not Product Market Fit09:22 Positioning Yourself for Luck13:33 Why Slow Initial Growth Might be OK17:28 Why True Passion Buys Staying PowerSend me a message to let me know what you think!