The Product Market Fit Show

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!

Dax built Lightspeed into a $1B ARR public company—even though he bootstrapped for the first 7 years. In this episode, he reveals exactly how he used a 4x pricing shift to create a global reseller machine that grew him to $10M ARR. He also breaks down why obsessing over design and deep customer empathy built the foundation for success.—and how stepping away from his comfort zone as an introverted developer was the key to scale. If you're an early-stage founder trying to nail pricing, distribution, and long-term strategic decisions, this story is your playbook.Why You Should ListenLearn how to price your product to build a distribution machine.Why early profitability can make your startup unstoppable.How bootstrapping forces clarity—and can unlock massive scale.Why the hardest move for founders is often letting go of what they're best at.Why giving away titles and equity too soon is a trap.Keywordsproduct market fit, pricing strategy, bootstrapping, reseller partnerships, early-stage startups, go-to-market strategy, startup scaling, founder lessons, Lightspeed POS, profitability00:00:00 Intro00:07:56 Landing the First Customers Without a Product00:11:28 The Pricing Strategy that Changed Everything00:19:20 Growth Through Partnerships00:26:18 Why a Business Plan Can Actually Help00:34:33 Profitable from Day One00:42:15 From On-Premise to the Cloud00:46:59 Finding Product-Market Fit00:49:15 The Truth About Early Employees and Equity00:53:18 Reinventing Your Role as Founder Every YearSend me a message to let me know what you think!

Carta just released their report for Q1 2025. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices. Carta data shows that graduation rates from Seed to A are as low as they've ever been. Bridge rounds make you even less likely to raise an A. And why seed-strapping might be an answer for many founders. VCs read and understand all this data. If you want to operate on equal footing— you should too.Why you should listen:What the Series A gap is and what do about it.Learn what the latest data says on valuations for seed and early-stage companies, round sizes etc.Why bridges and extensions have become so popular. Why bridge rounds have lower graduation rates to Series A.Why you might not need to move to the Bay Area to raise large rounds.Keywordsventure capital, AI, fundraising, market trends, valuations, startup ecosystem, early stage, late stage, investment, venture capital, bridge rounds, seed extensions, startup growth, hiring practices, AI impact, early stage funding, market trends, valuations, exitsSend me a message to let me know what you think!

Kazi Ahmed took a small insight—seeing friends cash out from Amazon brands—and built Carbon6, a software roll-up startup, selling it for $210M just three years later. But behind the quick success was a frantic scramble to survive. Aggressive acquisitions nearly ran them out of cash, forcing a brutal pivot from burning $1M per month to profitability and explosive organic growth. This episode dives deep into Kazi's playbook: when to ignore customer interviews, how to pivot on a dime, and why getting started immediately beats perfect planning every time.Why You Should Listen:How Kazi Ahmed built a startup from $0 to a $210M exit in just 3 years.Why chasing perfect ideas kills startups (and what to do instead).How aggressive acquisitions almost destroyed the company—and the tough pivot that saved it.Why customer interviews are overrated and sales beats surveys every time.How to identify when a roll-up strategy makes sense (and when it doesn't).Keywords:startup growth, Amazon FBA, acquisition strategy, profitable pivot, roll-up startups, founder stories, SaaS growth, startup exits, e-commerce software, early-stage advice00:00:00 Intro00:02:35 How COVID Unlocked an Amazon Gold Rush00:06:51 From Aggregating Brands to Aggregating Software00:12:04 Funding Acquisitions with Friends and Family00:16:18 The Art of Structuring Deals00:21:50 Pivoting from Acquisition Spree to Profitability00:26:35 Aggressive Cost Cutting and Cultural Reset00:29:43 Scaling Upmarket with a Sales-Driven Approach00:36:51 The $210 Million Acquisition by SPS Commerce00:40:26 Reflections and Realities of a Big ExitSend me a message to let me know what you think!

I break down my top insights from recent conversations with four founders who won in unconventional ways. You'll hear how Noah turned LinkedIn posts into his primary sales channel (without ever going viral), why Dan's startup survived a brutal 95% downround but ended up at $400M ARR two years later, how Adam turned a stagnant $3M ARR business into a $25M cash cow by solving one overlooked customer pain point. Plus, and how Cleerly used a 17 day-from- bankruptcy moment as its turning point. Why You Should Listen• How to turn LinkedIn into your best sales channel without going viral• Why a 95% downround doesn't mean your startup is over• How near-failure experiences can lead to breakthrough growth• The power of uncovering overlooked customer problems to drive massive profits• Why constraints and limited resources can become your biggest advantageKeywordsproduct market fit, startup growth, LinkedIn lead generation, fundraising, downround, bootstrapping, founder lessons, pivoting, scaling startups, entrepreneurship00:00:00 Intro00:01:01 How Stacker Leveraged LinkedIn for Explosive Growth00:04:43 Clutch's Wild Ride from Unicorn to Nearly Bankrupt and Back00:07:38 Navigating Market Cycles as a Founder00:08:32 Retention.com's Pivot from Stagnation to Massive Profits00:13:33 Cleerly's Near-Death Moment with Only 17 Days of Runway00:16:21 Why Constraints Are a Secret WeaponSend me a message to let me know what you think!

Public co-founder Jannick Malling shares exactly how he grew his startup from a tiny beta to millions of users—and hundreds of millions raised. He reveals why fractional shares changed the game for user acquisition, how the company cleverly seized on the GameStop moment to explode growth, and why relentless product focus was critical to scaling quickly. He explains the mindset shift needed to nail product-market fit multiple times and why you should only tackle timeless problems if you want your startup to last.Why You Should Listen• Learn how Public went from 1K beta users to millions in just 18 months by flipping the playbook.• Discover how to capture viral growth moments like GameStop and turning them into sustained growth.• Understand how intense product focus can drive massive results even with limited resources.• Hear why you need to solve timeless problems, not trendy ones.Keywordsstartup growth, product market fit, fractional shares, viral growth, Public investing app, fintech startup, user acquisition, scaling startups, startup advice, founder interview(00:00:00) How Public Went from 1K Users to Millions(00:09:41) Jannick's Path from Teen Designer to Fintech Founder(00:19:03) Fractional Shares Unlock Explosive Growth(00:26:31) Why Community was Key (and How it Actually Worked)(00:31:36) Launch Day Metrics Go Off the Charts(00:35:38) Unusual Strategy Behind Public's Word-of-Mouth Success(00:42:38) How Public Increased Average Deposits by 30x(00:49:12) How GameStop Doubled Public's User Base in 48 Hours(00:53:00) Jannick's Real Advice on Picking Problems That MatterSend me a message to let me know what you think!

Corporate spies stealing Slack messages. Adam Neumann raising another $100M (for WeWork 2.0?). AI startups hitting $34B valuations with zero revenue and ordering Ben & Jerry's ice cream over 15 payments with Klarna on DoorDash. April was wild, and Jack Kuveke joins the show to unpack the chaos, controversy, and insanity behind the biggest startup headlines. This is different than our normal episodes— definitely a much lighter twist, to be taken with a grain of salt. Let us know what you think!Why You Should ListenWhy Adam Neumann can raise billions—but you can't raise your seed roundHow a $40B valuation for AI startups might not be as insane as it soundsWhy espionage is moving from Wall St to Silicon ValleyWhat Klarna and DoorDash teaming up says about consumer debt cultureWhy A16Z thinks VCs will be the last job standing when AI takes overKeywordsAdam Neumann, AI startups, Silicon Valley espionage, A16Z, Klarna DoorDash, startup news, corporate spies, consumer debt, tech valuations, VC funding00:00 Intro01:45 Neumann's new $500 M raise and the WeWork déjà‑vu08:20 Deel‑vs‑Rippling spy saga uncovered13:00 11x growth scandal and TechCrunch backlash18:25 Marc Andreessen says only VCs are irreplaceable20:38 ChatGPT's $10 M “please & thank‑you” GPU bill26:10 Safe Super‑Intelligence and the $34 B pre‑revenue club30:00 Klarna × DoorDash lets you finance ice cream37:40 How consumer debt became America's default setting41:55 Quick survival guide for founders (and a few rants)Send me a message to let me know what you think!

Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people.In this episode, Forrest shares the brutally honest story behind Jobber's early days: months of rejection, maxing out credit cards, and nearly quitting. You'll learn why there are rarely any “silver bullets”, how he handled relentless investor skepticism, and how incremental daily improvements—not crazy inflection points—led to exponential growth. If you've ever wondered whether your startup can make it through the grind, this is a must-listen.Why You Should Listen• Learn how to persist through brutal rejection—Jobber took 6 months to land their first customer.• Understand why chasing “silver bullet” features or channels rarely works.• Find out when it makes sense to keep going despite extremely slow traction.• Hear why your first investors can shape or destroy your startup journey.• Discover why “compound growth” beats chasing short-term inflection points.Keywordsproduct market fit, startup growth, founder stories, fundraising, bootstrapping, Jobber, vertical SaaS, early stage startups, scaling startups, startup rejection(00:00:00) Intro(00:01:55) From Freelance Devs to Startup Founders(00:07:23) Six Months of Rejection(00:15:09) Landing the First Customer and Almost Losing Hope(00:25:39) Brutal Investor Feedback and the $250K Seed Round(00:35:13) Early Growth and Near-Death Experiences(00:44:15) Hitting Customer Milestones and Finding True Product Market Fit(00:48:41) Crossing $100M ARR and Key Lessons Learned(00:51:11) When to Quit and When to PersistSend me a message to let me know what you think!

He turned a personal travel tracker into an app with 10 million users and $10 million in revenue, with almost no funding. He reveals how ignoring conventional startup advice—like launching early, chasing revenue, or partnering for growth—was key to their viral success. He realized everything growth was about word-of-mouth. So the key to success was obsessing over a single metric: NPS. If you're an early-stage founder deciding where to focus, this is your must-listen episode.___Why You Should Listen• From losing 90% of users overnight to over $10M in revenue.• Why obsessing over Net Promoter Score (NPS) instead of revenue can drive explosive organic growth.• How to stay hyper-focused on one metric—and avoid distractions.• The truth about partnerships and why most startups shouldn't chase them.• The counterintuitive decision to build for quality first, even if it delays your launch.____Keywordsproduct market fit, startup growth, net promoter score, organic growth, consumer apps, app monetization, viral growth, user retention, travel app, early-stage startup_____(00:00:00) Losing 90% of Users Overnight(00:01:10) Turning a Personal Project Into a Travel App(00:09:36) Raising $50K and Building Before Launch(00:24:09) Launch Day and First 2000 Users(00:30:35) Why Chasing Partnerships Can Hurt Growth(00:36:40) How Polarsteps Reached $10M Revenue(00:41:00) Surviving COVID as a Travel Startup(00:42:20) Finding True Product Market Fit(00:43:26) The Moment Polarsteps Almost Failed(00:45:03) One Metric Every Founder Should TrackSend me a message to let me know what you think!

Jordan Boesch started 7shifts as a teenager helping his dad manage restaurant shifts. Today, his software runs scheduling for 50,000 restaurants. This episode dives into how Jordan bootstrapped early growth, why relentless focus on solving real customer pain mattered more than funding, and how tight partnerships supercharged his expansion. Jordan also shares hard-won lessons on managing burnout, dealing with near-failure, and creating a company culture that lasts. It's packed with practical insights every founder needs.___Why You Should Listen:• From side project to being used by 1 in 10 restaurant workers in the U.S.• How to use SEO and partnership strategies that drove early growth• Why customer complaints are often a good sign. • What to do when you're about to run out of cash. • See why defining clear core values early was key to building a resilient team._____(00:00:00) Building for Passion Not Profit(00:01:32) Solving Dad's Restaurant Problems(00:06:01) Getting the First Real Customer(00:10:47) Taking the Leap to Full-Time Founder(00:13:07) Moving to Silicon Valley and Finding Focus(00:16:51) Growth Hacking with SEO and Partnerships(00:24:59) How to Actually Make Partnerships Work(00:27:08) Building a Big Company Outside the Bay Area(00:30:29) Raising Money and Surviving Near-Failure(00:35:49) Defining Culture to ScaleSend me a message to let me know what you think!

Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years.He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots. Fast-forward two years, and he's doing $10M in revenue, profitable, with just 10 employees. He shares every bold tactic—bundling random AI packs, hacking Google rankings, landing affiliates, and manually doing customer support until there was no time left. Wes shares insights that every founder should know, including how he navigated intense competition, handled burnout, and maintained growth without a sales team. You'll walk away with clear, actionable strategies you can apply immediately.If you want a raw, practical take on zero-to-10M product-market fit in the AI era, this one's unmissable.Why You Should Listen:• How Wes grew Aragon to $10M ARR—without burning any money.• The guerrilla marketing tactics Wes used to turn a $30 idea into millions of revenue.• Why starting early let him outrun lookalike competitors.• How one affiliate blog post drove more than 50% of early sales.• How he managed high early churn in the early days until the product improved.Keywords:AI startups, early-stage growth, product-market fit, AI headshots, founder stories, affiliate marketing, startup tactics, SEO for startups, guerrilla marketing, startup growth strategies(00:01:54) Zero to $10M in Two Years(00:02:34) Exploring Ideas Before AI(00:05:25) Discovering the AI Headshot Opportunity(00:07:37) How Getting Fired Led to a Startup(00:18:31) Doubling Down on Professional Headshots(00:24:11) Early Guerrilla Marketing and Traction(00:27:59) From $2K to $200K a Month(00:32:13) Affiliate Marketing as a Growth Lever(00:43:18) The Moment of True Product Market Fit(00:47:18) Surviving Near-Failure and BurnoutSend me a message to let me know what you think!

Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable. The difference is in his first startup he was just catering to investors— in his second one only to customers. If you're an early founder chasing growth, listen to how Mike ditched vanity metrics, found sustainable traction, and grew ButcherBox past $500M in revenue—with no outside funding.____Why You Should Listen1. Why not raising can often be a powerful forcing function.2. Why what VCs want is often not the same as what customers want.3. How to differentiate in what seems like a commoditized market.4. Why there is no stronger force in startups than true product-market fit.______Keywordsproduct market fit, bootstrapping, butcherbox, direct to consumer, CPG subscription, grass fed beef, founder lessons, Kickstarter, food startup, early stage founder_____(00:00:00) Mastering the VC Game(00:01:45) How I Raised $30M Without Product Market Fit(00:08:21) Why my VC-backed Startup Failed(00:15:34) Growing Revenue but Losing Money(00:28:07) Early Signals of Real Product Market Fit(00:34:59) Solving Supply Chain to Scale ButcherBox(00:39:43) Bootstrapping to $550M (The Power of Constraints)(00:51:18) Product Market Fit from Day One(00:52:42) Why Founders Need a Lifestyle PlanSend me a message to let me know what you think!

Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves. If you're raising a pre-seed or seed, Gopi's tips will make your process faster, more targeted, and a lot less painful.___Why You Should Listen1. The 2-minute test for "real" pre-seed investors – Spot VCs who truly lead early rounds vs. those who waste your time.2. His 3-step framework for finding your perfect lead – Forget the 100 investor pipeline. Zero in on 10 prospects who'll actually write a check.3. How to balance short-term execution with a massive mission – Win over pre-seed VCs by knowing your next 6 months and your 10-year ambition.4. Why "business acumen" beats everything – Gopi explains how it trumps domain expertise or brand-name credentials.5. When to be fuzzy, when to be precise – The counterintuitive approach that shows you're open to customer feedback while still having big vision.____KeywordsPre-seed Funding, Early-Stage VC, Business Acumen, Go-to-Market Strategy, Founder–Investor Fit, Strategic Networking, Seed Round Pitch, Warm Introductions, Mission-Driven Startups, Conviction Investing____(00:00:00) Why Ruthless Prioritization Wins(00:03:29) Why Investing at Pre-seed is Personal(00:08:36) Investing When There Are Still Typos in the Pitch Deck(00:12:23) Spotting Founders with Exceptional Business Acumen(00:17:21) Great Ideas in the Hands of the Right Founder(00:26:29) The Practical Guide to Raising Your Seed RoundSend me a message to let me know what you think!

Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work. Yet healthcare's glacial pace, payers, and federal approvals all stand in his way. Hear how he's testing AI across thousands of patients, fighting for universal insurance coverage, and coping with near-burnouts. If you're a founder navigating hyper-regulated markets, Jim's journey is the blueprint.____Why You Should Listen1. Heart Disease Kills More Than All Cancers Combined – The staggering truth behind silent heart attacks (and why most diagnoses come too late).2. Jim's Big Bet on Early Detection – He's using advanced AI to spot “dangerous plaque” long before a patient gets chest pain or drops dead.3. A 10–15 Year Fight to Save Lives – The brutal reality of building a medtech startup in a system that moves slower than any other.4. Surviving a 17-Day Runway – How his mission-focus (and supportive backers) pulled Jim's startup back from the brink.5. Why repeated failure drives game-changing breakthroughs____KeywordsHeart Disease Detection, Medtech Startup, Coronary CT Angiogram, AI in Healthcare, Early Heart Attack Prevention, FDA Approval Process, CPT Code Reimbursement, Plaque Imaging, Cardiovascular Innovation, Clinical Trials____(00:00:00) Embracing Failure & Surviving Dark Days(00:01:56) From Cardiologist to Startup Founder(00:03:07) What Most People Don't Know About Heart Attacks(00:06:39) Using AI & Imaging to Predict Heart Attacks(00:09:19) Why Cleerly Needed to Exist(00:16:34) The Reality of Healthtech(00:20:41) How Cleerly Built its First Product—and Why it Wasn't an MVP(00:28:33) Raising $225M to Prove a Radical Idea(00:33:57) Finding Product-Market Fit & the Fight Worth HavingSend me a message to let me know what you think!

Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding.In this episode, Adam reveals why he ignored “scalable hacks” until his product proved undeniable, the two keys that finally unleashed product-market fit, and how he uses no-friction brand marketing on LinkedIn to sign up thousands of new leads.____Why You Should Listen1. He chose profit over fundraising – Adam shows how ignoring “growth-hack hype” and focusing on real word-of-mouth built a wildly profitable SaaS.2. Shocking pivot to product-market fit – A failed email tool spun out a game-changing identity product that users demanded.3. The #1 trap killing early-stage founders – Why “growth hacking” tactics fail without genuine pull, and what to do instead.4. Bootstrapping to $14M profit – His surprising path from 3M stalled ARR to unstoppable momentum (with a team of only six).5. LinkedIn brand building done right – How to attract thousands of perfect-fit leads—no spammy sequences required._____KeywordsBootstrapped SaaS, Product Market Fit, Email Marketing Growth, Founder Lessons, B2B LinkedIn Strategy, High Profit Margins, Startup Pivot, Word-of-Mouth Marketing, Early-Stage ExperimentationTimestamps(00:00:00) Intro(00:01:57) A Bootstrap Story(00:06:33) Why Bootstrapping Often Means You Can't Lose(00:10:36) The downside of raising VC(00:19:53) A Case Study: Constant Contact(00:22:45) Find an Unsolved Porblem(00:32:06) PMF and Word of Mouth(00:46:45) Piece of AdviceSend me a message to let me know what you think!

Dan Park joined Clutch when it was selling 20 cars a month. Then he grew it from $20M in 2019 to $200M in sales by 2022. He was one of Canada's fastest growing companies. Just as he was going to close a $100M round, the macro changed completely. Suddenly, he was left with only six weeks of cash. He was forced to go through a 97% down round at a $15M valuation.Just two years later, he not only grew right back to a $575M valuation, he also doubled revenue from its previous peak to $400M.This episode unpacks every near-disaster move, including turning off test-drives (and why it worked), re-engineering unit economics in real time, and renegotiating debt so Clutch could keep buying cars. Dan's hard-won lessons will change the way you think about speed, iteration, and survival._____Why You Should Listen1. He had just six weeks of runway – Find out exactly how Dan rescued Clutch from the brink.2. Taking a car startup to $400M in sales – The surprising moves that made consumers buy cars online, sight unseen.3. Cutting 75% of staff—then doubling revenue – The inside story of Clutch's brutal pivot and swift rebound.4. How to survive capital-intensive nightmares – Lessons on debt, term sheets, and crisis-mode fundraising.5. Why fast iteration trumps everything – Dan's secret to making big bets—then yanking them back if needed.________KeywordsUsed Car Marketplace, Capital-Intensive Startup, Near-Bankruptcy Turnaround, Automotive E-Commerce, Cash Flow Management, Startup Layoffs, Rapid Iteration, Debt Restructuring, Growth vs. Profitability, Founding Team DynamicsTimestamp(00:00:00) Intro(00:02:23) The Birth of Clutch(00:04:37) The Chicken and Egg Problem(00:08:31) How Do We Scale This?(00:14:21) Baby Steps and Achievable Milestones(00:22:45) Becoming Profitable(00:34:45) Do Whatever Makes Sense for The Business(00:37:29) Finding Product Market Fit(00:42:23) Piece of AdviceSend me a message to let me know what you think!

Noah Greenberg grew a content-distribution product from zero to $1M ARR in just one year (and to $4M in 2 years) by focusing on a single channel most founders underrate: LinkedIn. He posted insights daily, highlighted key players in his industry, and made it impossible for prospects not to notice him.In this episode, Noah reveals the exact step-by-step playbook, including how to structure 3-month pilots for fast feedback, craft DMs that actually get replies, and pick the right content “watering holes” so your future customers come to you eager to sign. If you're a founder trying to figure out your go-to-market approach, you need to see what Noah did.______Why You Should Listen1. Turning LinkedIn into a Free PR Engine – Noah shows how daily micro-posts drive high-value leads without needing to go viral.2. Finding Your First 10 Customers with 3-Month Pilots – Short trials = instant feedback on who'll stay and who'll churn.3. Never Stop Triangulating – How 50 customer conversations per month reveal the right product, price, and packaging.4. Selling without Selling – The “this isn't a pitch” call that makes prospects lean in and ask, “Wait, how do we buy?”5. Earning Credibility at Scale – Noah's “watering hole” posts spark real engagement from decision-makers (and reel in 5-figure deals)._______KeywordsB2B Sales, LinkedIn Strategy, Early-Stage Growth, Founders' Playbook, Bootstrapped Startup, Content Distribution, Sales Prospecting, Pilot Contracts, Outbound Leads, Product-Market FitTimestamps(00:00:00) Intro(00:02:35) Stacker's Origin Story(00:06:00) How to generate warm leads(00:15:53) How to use LinkedIn for lead gen(00:21:42) No One Wants To Be Pitched(00:26:06) How to get feedback on pricing(00:38:08) LinkedIn Go-To-Market Strategy(00:42:20) Breaking Above The NoiseSend me a message to let me know what you think!

Jack Kuveke has cracked the founder game—by doing the exact opposite of what every expert tells you. We break down the “real” startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard). Forget chasing product-market fit. Start chasing growth, money, and, most of all, hype.Why You Should ListenWhy you need to spend most of your time fundraising.Learn exactly how to fake traction, drive FOMO and raise millions-- even with a terrible product.Get Jack's ultimate playbook for quitting early and winning big (without working hard)How secondaries can make you rich BEFORE your startup fails.Why League of Legends is the key to startup successKeywordsstartup fundraising, pivot strategy, early stage VC, founder mistakes, product market fit, startup advice, venture capital, startup growth, entrepreneur mindset, founder stories(00:00:00) Intro: Why Quitters Win and Fundraising Beats Traction(00:02:54) Ex-Googlers Can't Hack It as Founders(00:03:12) Raising Money is Your Only Job(00:10:49) How to Fake User Growth & Create FOMO(00:14:18) Quit Fast, Pivot Faster(00:15:28) Jabroni Capital: The World's Worst VC Fund(00:26:26) Hiring Hacks: How to Convince People to Join Your Startup(00:28:27) Adam Neumann: Hero or Villain?(00:38:16) The Real Jack Kuveke: Satire, Startups, and Why VC is BrokenSend me a message to let me know what you think!

Wes Bush wrote the original bestseller on Product-Led Growth—and then watched everyone try to copy Dropbox and Slack without truly getting it. Now, he's here to break down exactly what goes wrong when early-stage founders jump into PLG, how to spot your product's “million-dollar free problem,” and how to fix the three biggest onboarding gaps that sabotage new users.He'll show you why some sales-led companies die when they try freemium, how to carve out a simpler “first strike” moment, and the reason you need bumpers (like an onboarding checklist) to guide people to success. If you're still using the “Request a Demo” button, this episode could totally transform your approach and give you a self-serve funnel that scales faster than any sales deck ever could.Why You Should Listen1. Make Users “Smell the Cologne” – Learn Wes's approach for letting users experience the core value before they buy.2. Turning Complex Setups into a No-Brainer – How to map out product, skill, and knowledge gaps so anyone can get started.3. Bowling Alley Onboarding – A framework to slash unnecessary steps, guide users to that “aha” moment, and cut churn.4. Freemium vs. Free Trial vs. Reverse Trial – How to pick the perfect model for your startup.5. Sales-Led to Product-Led – Why some founders fight this shift, and how to pull it off without blowing up your funnel.KeywordsProduct-Led Growth, PLG Strategies, SaaS Onboarding, Freemium Model, Free Trial Optimization, User Adoption, Customer Success, B2B SaaS Growth, Onboarding Framework, Go-to-Market TacticsTimestamp(00:00:00) Intro(00:01:27) What is Product Led Growth(00:04:37) When to use PLG(00:18:20) Why Simplicity is the key(00:20:15) Wes's Favorite Case Study(00:25:42) The Bowling Alley Framework for Onboarding(00:31:02) Free Trials Must Have Progression(00:36:28) Finding Those Ideal Limits on your TrialsSend me a message to let me know what you think!

Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched in Toronto, backed by billions in funding, he thought it was over.Instead, Skip became Canada's dominant food delivery platform and got acquired for $200M.Then Jeff did something even crazier—he decided to take on the banks.With Neo Financial, he's tackling Canada's most entrenched industry, building a modern, full-stack digital bank from scratch. He's raised $100s of millions at a $1B valuation.Why you should listen:How bootstrapped SkipTheDishes took on $10B UberEats How to build a three-sided marketplace.Why building trust with customers is key to long-term success.Why beginnings are always messy and more about grit than perfection.Why Jeff didn't stop after exiting for $200M.KeywordsSkiptheDishes, Neo Financial, entrepreneurship, delivery service, startup journey, market competition, founding team, restaurant industry, business growth, feedback loop, three-sided marketplace, startup journey, Canadian startups, entrepreneurship, financial services, exit strategy, partnerships, growth strategies, advice for foundersTimestamps(00:00:00) Intro(00:02:00) Gotta Have Thick Skin(00:03:54) Skip's Origin Story(00:07:18) Competing with Uber(00:16:09) The First Few Restaurants(00:22:45) Initial Demand(00:26:28) Three-Sided Marketplace(00:38:38) The Original Mission(00:52:10) The First Year at Neo(00:58:40) Product Market Fit(00:59:55) A Piece of AdviceSend me a message to let me know what you think!

One of the most common questions I get is 'How do I know if I have product market fit?" Especially when you're in that gray zone where things are kind of working but they're not really taking off yet, how do you know if you have product-market fit or not?That's exactly what we dive into here. Why you should listen:Why demo to close is an excellent leading indicator of PMF.Why NPS is not as good as Sean Ellis test to measure product-market fit.Why retention is the best long-term metric, but takes long.What qualitative signals you'll feel when you have true PMF.What to do if you realize you don't have real product-market fit.This podcast originally aired on Matt's podcast called Product Driven, because the topics were so relevant, I figured I'd post it here too.Timestamps(00:00:00) Intro(00:00:55) How do you know if you have PMF(00:06:33) Why some problems are good(00:11:24) Solve a True Top of Mind Pain(00:15:54) Why timing matters(00:21:30) How to Know When to Pivot(00:25:00) Asking the Right Questions to CustomersSend me a message to let me know what you think!

Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI.Then ChatGPT dropped.Suddenly, Pinecone was the must-have database for AI apps, with thousands of developers signing up daily. The company exploded, leading to a $100M round led by Andreessen Horowitz and a 10x revenue surge.If you're an early-stage founder, this episode is a must-listen.Why you should listen:•How he went from from 40 VC Rejections to a $10M Seed Round• Why he quit a High-Paying Job at AWS to start a Startup• The game-changing shift that made VCs finally “get it”•What really happened inside Pinecone when AI took off•Why most founders misunderstand market timing and what to do about itKeywordsAI, Machine Learning, Startups, Entrepreneurship, Vector Databases, Fundraising, SageMaker, AWS, Technology, Innovation, Pinecone, vector database, seed funding, ChatGPT, startup growth, business model, AI, infrastructure, early stage foundersTimestamps(00:00:00) Intro(00:07:50) Edo's Story(00:12:27) The Early Days of Machine Learning(00:32:23) Seed Funding(00:42:09) Unsustainable Scaling(00:53:41) Told You So(00:59:24) A Piece of AdviceSend me a message to let me know what you think!

Jon Yoo's startup wasn't working. He pivoted mid-YC, spent five brutal weeks without signing a single customer, and then—right after raising his seed round—his co-founder left.Most startups die right there. Instead, Jon figured out how to land massive customers like FiveTran and Snowflake. He grew from $500K to $2M ARR in 6 months. Why you should listen:•Navigating a founder breakup – What happens when co-founders split and how to handle it.•The real YC experience – What worked, what didn't, and how they pivoted mid-program.•Landing major customers – How they got big logos like Snowflake.•Fundraising insights – What really matters to investors at the seed and Series A stages.•Why startups need forcing functions – The tactics that drove fast product development.•How to know if you have product-market fit – The signals John saw at Sugar.•Burn rate discipline – Why they raised millions but barely spent it.Keywordsentrepreneurship, startups, investment banking, Salesforce, Y Combinator, founder dynamics, product market fit, scaling, cloud marketplaces, business strategy, fundraising, startup, YC demo day, customer acquisition, product-market fit, founder dynamics, early stage startup, team building, scaling, challengesTimestamps(00:00:00) Intro(00:07:55) The Origin of Suger(00:13:30) Going All In(00:19:08) The first 10 customers(00:24:20) The Hardest Pain Point(00:30:29) Becoming Profitable(00:37:05) Celebrate The Small Wins(00:39:56) Finding Product Market Fit(00:42:27) A Piece of AdviceSend me a message to let me know what you think!

This is one of the wildest founder journeys you'll ever hear. Dmitry Gurski went from growing potatoes and picking mushrooms on a farm in Belarus to building Flo—a billion-dollar company with 75M monthly users that dominates the health and fitness category worldwide. He started Flo in a market already controlled by PayPal co-founder Max Levchin's startup, which had $30M in funding from a16z. Today, Flo is 100x bigger than its once-dominant rival.Dmitry shares raw, unfiltered startup truths—like why he got rejected by 200+ VCs, why 90% of startup failures are team-related, and why most founders are delusional about product-market fit. He breaks down how simplicity beats complexity in product, why retention is everything, and how deleting features can actually boost revenue.If you're a founder, this episode will fundamentally change how you think about perseverance, pivots, and building something that lasts. Listen now—you'll be referencing this one for years.Why you should listen:Why big market beats niche – How Flo won because it targeted all women's health while competitors focused only on fertility.How Retention is the real test – A product with natural recurring use cases (like periods) has built-in retention, unlike fitness or productivity apps.Why simple wins – The first version of Flo was less complex than competitors but had far better predictions—accuracy mattered more than features.Fundraising is brutal – Flo got 300+ investor rejections before raising $300M. Many VCs just didn't “get” the space.Keywordsstartup, entrepreneurship, product design, user retention, Flow app, health and fitness, early stage founders, product market fit, simplicity, user engagement, retention, user case, app development, entrepreneurship, product market fit, mobile apps, business strategy, team dynamics, failure, success, risk, uncertainty, decision making, market demand, competition, product-market fit, fundraising, entrepreneurship, startup success, female healthTimestamps(00:00:00) Intro(00:09:10) Why you Need to Keep it Simple(00:13:10) Why B2C is All About Retention(00:19:05) Why you Need to Delete Features(00:24:14) PMF is about the Shape of the Curve(00:39:17) When to Persevere, When to Pivot, and When to Quit(00:42:22) More attempts = more success(00:51:34) The Idea for Flo(00:59:05) Finding Product Market Fit(01:02:07) Advice for An Early Stage Founder(01:10:22) A Potato StorySend me a message to let me know what you think!

Saurav started a Groupon-like offering for SMBs in 2011. He quickly learned it wasn't going to work. He and his team pivoted and started driving leads to suppliers using Facebook ads. It worked and they generated revenue—but they were becoming a digital advertising agency. It wasn't at all what they wanted to build.So they pivoted again.  They used the cash from that business and built Perkbox. The idea was a subscription-based offering that that gave perks to SMB customers. Telcos started buying it and attaching it to their products to drive sales. Then, they pivoted again, this time moving away from customer perks and to employee perks.This time, it worked. They grew from $2M in ARR to $14M in just 2 years. They kept growing and hit $36M in ARR. Then he sold the business to PE for $170M.It took longer than expected. There were more pivots than expected. But it was a huge success.Here's how it happened.Why you should listen:How to use new social media channels to drive growth.How to leverage partnerships to get end user adoption.Why having a profitable agency can be a great way to get started.Why capital efficiency can be a huge edge.Rebranding can help clarify market positioning.What it feels like to make $10s of millions in one day.KeywordsPerkBox, Groupon, startup journey, business model, SMB market, marketing strategies, recurring revenue, partnerships, entrepreneurship, exit strategy, venture capital, entrepreneurship, startups, employee benefits, social media marketing, capital efficiency, business growth, acquisition, rebranding, emotional marketing, lessons learnedTimestamps(00:00:00) Intro(00:01:48) The origin of Perkbox(00:04:52) Going after SMBs(00:12:16) The Pivot(00:26:35) Creating Viral Ads(00:32:28) Demo to Close Rate(00:40:12) Selling to PE Firms(00:49:38) A Piece of AdviceSend me a message to let me know what you think!

In 2005 most people didn't even have cellphones yet. Those who did used flip phones. That's when Noah started Olo, a webapp to let people pre-order coffee from nearby shops. Users had to login on web, add a credit card, create pre-made orders and then send a text to a preset number when they wanted to pre-order. It was way, way ahead of its time. Noah and his team 7 years to hit $1M in ARR. In the meantime, they raised a round with 50% dilution the week before the financial crisis, went on live TV to an audience on 6M viewers and had to pivot from a marketplace to B2B SaaS.But overtime smartphone penetration increased, on-demand ordering became a trend, and then, one day, Starbucks launched their app. All of a sudden, every single restaurant in the world wanted a way to let their users pre-order.And there was Noah and his team at Olo.Today, Olo is a public company worth over $1B and generating nearly $300M in sales. Here's the story of how it happened.Why you should listen:How to use guerrilla marketing tactics to get early growth.Why PR can move the needle but not in ways you expect. How to pivot from a marketplace to B2B SaaS.Why it often takes much longer than you might hope to hit an inflection point.Why fundraising was so hard, even though Olo became a $1B+ public company. Why Noah thinks founders should embrace challenges and adversity.KeywordsOlo, Noah Glass, entrepreneurship, product-market fit, restaurant technology, mobile ordering, startup journey, business challenges, marketing strategies, innovationTimestamps:(00:00:00) Intro(00:02:20) Building an app in 2005(00:13:20) The Burn the Boats Moment(00:16:31) Building A Network Business(00:26:08) The Cold Start Problem(00:30:33) A Happy Accident(00:36:55) Going through the 2008 Financial Crisis(00:51:20) Finding Product Market Fit(00:57:20) Blueprint of Values(01:05:11) Best Piece of Advice(01:06:08) A Big MilestoneSend me a message to let me know what you think!

Frankie lost $10K in a crypto transaction—so he started Staging Labs to find a way to help others prevent crypto scams. He was head of an incubator called Entrepreneurship First and had seen dozens and dozens of founders build startups. He knew exactly what to do—and he did everything right. He found a co-founder, built an MVP, did customer discovery, checked willingness to pay—but he still failed.The world changed when crypto crashed in late 2022. The people who were originally interseted in paying for crypto insurance nolonger were. And by the time Frankie realized it, it was too late.Here's how it happened—and how he was able to sell his startup even though the product wasn't working out.Why you should listen: How to sell your startup even when it's not working out.Why sometimes the best ideas come from personal struggles. Why you need to constantly validate willingness to pay.Why you can't treat lean startup as a series of checklists.The last 10% of execution is often what determines success or failure.Partnerships can be a double-edged sword in startup strategy.How aligning personal values with customer needs is essential for founders.Keywordsentrepreneurship, startups, crypto scams, fundraising, product launch, market timing, personal experience, validation, community building, business challenges, willingness to pay, user experience, scams, customer alignment, market cycles, acquisition, strategic partnerships, investor relations, startup lessonsTimestamps:(00:00:00) Intro(00:02:25) The Idea & The Origin of Staging Labs(00:08:07) Next Steps & Pre-Seed Fundraising(00:13:27) Why you should never depend on partnerships(00:18:28) How to create urgency(00:24:55) Pivoting(00:28:43) Trying to sell the business(00:35:55) Biggest Lessons LearnedSend me a message to let me know what you think!

Hussein's travel startup was doing $10s of millions when COVID hit. His revenue didn't just go to zero, it went negative. There were more customers asking for refunds than new sales. He was 4 months from running out of money.He ended up making a complete pivot, he changed the company's name from SnapTravel to Super.com. He went from travel to fintech and launched a banking card. It seems like a strange pivot —but through deep research he'd realized what his customers truly needed. They needed more money—not for travel or vacations—but for every day life.The new card helped customers earn points and rewards, it helped them save on everyday expenses. The pain was so acute and the solution so perfect, that just 3 years later, Super.com is doing $150M in ARR.Like Hussein said, he got 50 'no's from VCs for every 'yes' he got. He saw his business grow and then crumble over night. He was literally going to zero. But he turned it all around. Now he's not just growing, he's profitable now.And here's how it went down.Why you should listen:How to think from first principles to figure out the right product expansion.Why cross-selling is much harder than you think, and how to make it work.Why finding an unfair advantage is key to scaling a startup.How to use actual customer behavior to understand what customers truly want.Why testing and validating ideas through smoke tests is essential.KeywordsSuper.com, SnapTravel, COVID-19, travel industry, pricing strategies, customer needs, market fit, entrepreneurship, AI, business growth, COVID-19, resilience, travel industry, financial innovation, membership model, customer insights, entrepreneurship, investor relations, business strategy, cross-sellingTimestamps:(00:00:00) Intro (00:02:39) The original startup: Snap Travel(00:08:40) Why a great user interface is a big edge(00:11:26) How to acquire customers(00:13:30) When your entire hypothesis is wrong(00:22:52) Meeting Steph Curry(00:29:03) Nearly crashing to zero-- and going bankrupt(00:33:51) Starting over and rebranding(00:42:42) Creating the Fastest Growing Membership Program(00:52:17) Finding Product Market Fit(01:00:00) One Piece of AdviceSend me a message to let me know what you think!

When Amplitude launched Mixpanel was the big game in town. They were first to market, had raised more money, and had a well-known brand. VCs passed on Amplitude because it seemed like just another Mixpanel.Today, Amplitude is a $1.5B public company—they're about 50% bigger than Mixpanel. Mixpanel's marketing spend helped educate the market. But before buying an analytics solution most businesses do market research. That's when they'd find out that Amplitude had several features Mixpanel lacked—and they were much, MUCH cheaper.It's not cool to win on price, but it works. It worked for WalMart, CostCo, Shein, and it worked for Ampltiude.Here's the story of how it all happened.Why you should listen:How to use cheaper prices to win in a crowded market.Why you often need 12 hour days to win in Startupland.Why even massive $1B+ successes often have trouble raising early rounds.How pivoting can often be the key to finding real market pull.Why big competitors can often be a huge tailwind.How to use storytelling to raising bigger rounds. Keywordsstartups, entrepreneurship, analytics, Amplitude, pricing strategy, market positioning, data processing, voice recognition, technology pivot, competitive advantage, market dynamics, differentiation, product-market fit, storytelling, fundraising, startup challenges, customer relationships, analytics tools, business strategy, entrepreneurshipTimestamps:(00:00:00) Intro(00:06:13) A cool demo-- but a bad business(00:18:36) Why funding was so hard(00:25:43) Why lower prices are a big differentiator(00:40:50) Working 24/7(00:50:35) Product Market FitSend me a message to let me know what you think!

This first time founder just raised a $38 million Series A. The crazy part is that for all of 2021, 2022, 2023, he had almost no revenue. He spent all that time building and pivoting. Finally he launched in 2024—and it blew up.I saw his LinkedIn post and his revenue chart doesn't look like a hockey stick... it looks like straight a vertical line. He built a health benefits platform—it doesn't get less sexy than that. And yet, it absolutely exploded to millions in ARR in less than a year.All because he figured out how to make something that every single company in the U.S. needs, exceptionally simple. Here's the story.Why you should listen:Why choosing the right co-founder is the most important thing.Why having a mission is crucial to make it through the ups and downs.How to listen to and understand customer pain points. Why pivots are not a bad thing, and can actually be the key to crazy traction.How to use external deadlines to drive urgency and focus .KeywordsThatch, startup journey, co-founders, healthcare innovation, product market fit, venture capital, entrepreneurship, health benefits, business challenges, pivoting, healthcare, startups, product development, market demand, customer needs, external deadlines, product market fit, scaling, company culture, founder intuitionTimestamps:(00:00:00) Intro (00:02:27) Finding the Right Co-Founder(00:10:23) Why You Need to Go All In(00:16:20) The Seed Round & Pivoting From the Original Idea of Thatch(00:30:08) How to use external deadlines to drive focus(00:37:55) The Growth in 2024 & The Business Model(00:42:16) The Benefits of Forcing Functions(00:45:58) How Many Customers are Using Thatch Today?(00:47:50) Finding True Product Market Fit(00:52:10) People Didn't Believe in ThatchSend me a message to let me know what you think!

Carta just released their report for Q4 2024. 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 much lower for companies that have raised a bridge round. We analyze why that might be and what that could mean for early-stage founders.VCs read and understand all this data. If you want to operate on equal footing— you should too.Why you should listen:The role of AI in the venture capital landscape.Why there are a trend of larger funding rounds going to fewer companies.Why so much capital is being allocated to AI companies.Valuations for seed and early-stage companies are on the rise.Why bridges and extensions have become so popular. Why bridge rounds have lower graduation rates to Series A.What the data shows about how hiring practices are changing.Keywordsventure capital, AI, fundraising, market trends, valuations, startup ecosystem, early stage, late stage, investment, venture capital, bridge rounds, seed extensions, startup growth, hiring practices, AI impact, early stage funding, market trends, valuations, exitsSend me a message to let me know what you think!

Alon was a hacker for the Israeli Defence Forces' cyber department. There he saw the most advanced methods used in cyber warfare. So when he left, he started IntSights-- a company that helped enterprises defend themselves from cyber attacks. He was a first-time founder who didn't even know the word 'unicorn'. He made all the mistakes you could make. But he had real, undeniable pull. He grew to $1M ARR in a year and to $4M a year later. By the end of it, he was doing $30M in revenue and exited for $335M.But when I asked him what it felt like to sell for hundreds of millions, he said it 'felt like emptiness'. Alon is a builder—that's all he wants to do. So he quit post-acqusition and left millions of dollars on the table. Moeny he was guaranteed to make if he just stayed in his role.Instead, he started PointFive to help enterprises reduce wasted spend on cloud infrastructure. He know nothing about the space. One year in, he's raised $36M and grown to millions in ARR—it's even faster than IntSights.Here's the story.Why you should listenWhy Alon felt empty after exiting for $335M.Why he left millions of dollars on the table to start a new startup.Why the mistakes he made in his first startup helped his second one grow way faster.Why he raised $36M in under a year.Why true customer pull comes from solving top of mind problems.KeywordsLinkedIn, video content, cloud cost optimization, engineering responsibilities, startup funding, second-time founders, product market fit, customer traction, entrepreneurshipSend me a message to let me know what you think!

Ned had a chance to run Robinhood Asia but he turned it down. Instead, he launched a competitive product. He decided to go B2B and sell to banks and other financial institutions. He locked down a $400K revenue sale before writing a line of code. It seemed easy at first. Overtime, he grew to $3.5M in revenue, billions in assets under management and hundreds of thousands of users. He raised $20M in venture capital. But then the problems started. Enterprises that paid for large contracts didn't push the product—many had no marketing budgets. In some cases, they shelved the product altogether. The one-time revenue never turned into ARR. Running out of money, he was forced to raise a small bridge and lay off more than half his staff.He came close—but ultimately, he just wasn't able to recover. He sold off the company for parts and went through a wind down. This is his story—and the lessons he learned.Why you should listen: Why the difference between success and failure can be minimal.How to balance custom contracts with building scalable product. Why enterprises might not push the product they've paid $100K+ for.How to build a strong company culture.Why layoffs are the hardest thing a founder will go through.When things go south, "the days are long, but the months are short".Keywordsstartup, FinTech, B2B2C, customization, revenue models, marketing, client engagement, leadership, company culture, lessons learned, B2B sales, startup challenges, emotional toll, liquidation, lessons learnedSend me a message to let me know what you think!

Jason built a data center company in the 2013. When he exited in 2019, it was the third-largest exit in Canada that year. He'd sold his previous startup and invested 100% of his capital into ROOT. He grew to 10s of millions and exited for 100s of millions. Now he's invested in over 20 angel-stage startups. He shares the story of ROOT and what he looks for in the startups and founders he backs.  Why you should listen:Why seeing inefficiencies can lead to huge advantages vs competitors.How customer concentration can actually lead to a huge success.Why the 'Why Now' slide is so important.Why Jason values startups can get to free cash flow within 1-2 years.How to use the lead to conversation ratio as a leading indicator of PMF. Keywordsdata centers, investment, entrepreneurship, product market fit, angel investing, business growth, technology, risk management, funding strategies, customer relationships, investment, startup, venture capital, product-market fit, founder advice, business model, cash flow, total addressable market, team dynamics, entrepreneurial hungerSend me a message to let me know what you think!

Pablo is the first guest that has the same name as me-- so you KNOW this episode will be great. Pablo hustled for months just to get to $70K in ARR. He got rejected from YC, re-applied, and finally got in.But after months in YC, he realized his first product was not going to work. He had some traction, but not nearly enough customer pull. So he shut it down. He went back to square one. He did customer discovery in a totally different space and leveraged the latest in Gen AI. He then built AI agents that automate calls in the logistics space.Just a year after shutting down his first product, he'd grown to $2.2M in ARR. In December, he raised $15.6M from a16z. Here's how it happened.Why you should listen: Why you should be careful of "free" money from grants.Why YC changed the trajectory of Pablo's startup.How a big pivot is often necessary-- even when you have customer traction. Why the key is to find a true, no-brainer pain point.Meeting customers where they are can lead to smoother adoption of new technologies.How to build a product that provides clear ROI is essential for customer buy-in.Continuous exploration and adaptation are key to finding the right market fit.KeywordsHappy Robot, startup journey, product market fit, early stage funding, co-founders, computer vision, YC, venture capital, entrepreneurship, business development, funding, European founders, Y Combinator, customer acquisition, pivoting, logistics, AI agents, startup growth, Series A, market researchSend me a message to let me know what you think!

Alex sold his last IoT startup for over $200M to Samsung. He felt the needed to build something much bigger, so he started BrightAI. The goal was to use AI and IoT to solve big problems for enterprises. A few years later, he bootstrapped to $100M in revenue across just 7 customers.  Last quarter, he raised $15M in venture funding. He shares how he closed million-dollar enterprise projects before building a product, why he refuses to go after just one vertical, and some of the biggest lessons he's learned after years building startups.Why you should listen:Why impact is the biggest driver for starting startups. How to find champions and get enterprise design partners.How AI and IoT can combine  to solve real-world issues.How to make sure you don't get stuck in a niche forever.How to tell if you're on to something in less than 18 months since launching. KeywordsSmartThings, Bright, IoT, critical infrastructure, pest control, AI, technology, innovation, entrepreneurship, product development, AI, pest control, multimodal AI, revenue streams, platform scaling, product-market fit, early-stage founders, entrepreneurship, sustainability, critical infrastructureSend me a message to let me know what you think!

Nathan has interviewed 100s of founders on how they raised their first few rounds. In this interview, we go through some of the most compelling stories he's heard. We go through step-by-step what you should do to raise a round, how to get meetings, how to tell stories, and every other piece of the fundraising puzzle.If you're planning to raise a round anytime this year-- check this episode out.Why you should listen:Why you need to look for believers in the early days.Why you need to meet way more investors than you might want to.How to create momentum for your round.Why spending more time planning will mean spending less time raising. Keywordsfundraising, startup, venture capital, investor relations, fundraising process, founder stories, capital raising, startup funding, investor introductions, fundraising strategiesSend me a message to let me know what you think!

A few years into building Flashfood, Josh was $35K in debt with no money in his account. Just a few months earlier, he'd lost both the pilot customers he'd worked so hard to lock in. He'd worked for months to land them and had delivered what he promised.But both retailers told him the problem he was solving was not important enough.And then, he met Loblaws-- one of Canada's largest retailers. They loved the case studies he had. They tested it out and quickly launched it across 100% of their locations. "I was going to shut down the company." That's how close it came to failing completely. Instead, a year after meeting Loblaws he was doing $1.5M ARR and had raised a $3M seed round. Now, he does 10s of millions in revenue and will soon be profitable.Here's the story.   Why you should listen:Why startups often drive founder to near bankruptcy.Why you need to keep testing your startup until you hear 'no'.Why sometimes large customers might be easier to close than small ones.How to get champions to close enterprise deals. Why you might be a top priority for some customer sets and not others.Keywordsfood waste, grocery stores, app development, early stage founders, product market fit, sustainability, entrepreneurship, discount food, consumer behavior, environmental impact, enterprise sales, customer priorities, stakeholder buy-in, corporate culture, product-market fit, revenue growth, grocery industry, startup challenges, business strategy, environmental impactSend me a message to let me know what you think!

Darius started an EdTech startup to help users of online courses collaborate with each other. It blew up during COVID when everyone felt isolated. It gained thousands of users. They were engaged. They came back to use the platform. And, most importantly, they dramatically improved completion rates for online courses.Darius thought he had it. But it turned out universities didn't want to pay. What users cared about was not what universities (the buyers) cared about. His biggest lessons is that he should've pivoted much sooner. Here's why.Why you should listen:Why success and failure are often not that far apart.Why engagement and usage don't always lead to revenue.How to figure out the KPI that matters for your buyer.Why users and buyers are not one and the same.Why you need to pivot much sooner than you might think-- or like.Keywordsstartup challenges, entrepreneurship, online learning, EdTech, market dynamics, product development, business strategy, lessons learned, networking, pivotingSend me a message to let me know what you think!

Zach was burned out after a decade of working at top roles in Coinbase, Square and Brex. He quit with no startup idea-- and then, he went right back in. Given their background, Zach and his co-founder quickly raised an $8M seed round to build an NFT-related product in Web3.One month later, they completely abandoned their idea. They realized it was never going to work. Then, the floor fell from underneath them. FTX went bankrupt. SVB fell apart. They took punches to the face for the first 6 months straight.But, when everyone was paying attention to Gen AI in late 2022, Zach kept going deep in Web3. He noticed stablecoins were growing but there was no platform for developers to build with. So he built Bridge, a Stripe-like API for stablecoins.The first months post-launch were underwhelming-- until they landed a fast-growing customer. From then on, the next year was exceptional 10x+ growth. Then Stripe noticed them.In Oct 2024, they were acquired for $1.1B. Just 2.5 years after he started.Here's the story of how it all happened. Why you should listen:Why even $1B+ exits still feel like rollercoasters from the inside. How to quickly abandon ideas and pivot to what truly matters.How they found a massive opportunity where no one else was looking.Why starting outside of the Bay Area was critical to their success.Keywordsstartup, billion-dollar exit, stablecoins, investor relations, crypto, fintech, market dynamics, entrepreneurship, pivot, challenges, stable coins, startup journey, acquisition, fintech, market resilience, product market fit, Pablo Srugo, Bridge, Stripe, entrepreneurshipTimestamps(00:00:00) Intro(00:2:46) Starting at the Worst Time(00:8:56) The Emotions on Pivoting a Month After Raising(00:11:44) Pivoting(00:18:24) Leaving Brex(00:20:36) Working on Something Out of Trend(00:28:34) The Core Beliefs of Bridge(00:32:56) Launching & First Customer(00:38:57) Sometimes you Can't Think Too Much(00:42:29) Series A(00:44:24) The Acquisition(00:49:05) The Feeling of Exiting for a Billion(00:52:24) One Piece of AdviceSend me a message to let me know what you think!

We took examples from the last 100 episodes and built a clear, 5 step path to finding product market fit:1.Before Startup Mode, There's Research Mode —> Become an expert to find problems worth solving. 2.Only the Insanely Focused Survive —> Focus all your resources to do more with less. 3.You have to be in the market to win the market —> Use niche markets to discover unique insights. 4.Forget Growth. Find Value. —> Optimize for value delivery and growth will follow. 5.Pivot Harder, Faster —> As soon as you realize you're not solving a #1 problem, pivot.Why you should listen:Why creating value by solving problems is the core of startups.Startups must avoid perfectionism and embrace learning.Research mode involves deeply understanding customer needs.Insane focus and hustle are essential for early-stage success.Validation comes from engaging with the market directly.Why growth should be a byproduct of delivering value.Keywordsstartups, product market fit, entrepreneurship, research mode, focus, hustle, validation, customer experience, growth, business strategy, Wattpad, user-generated content, agility, iteration, product market fit, startup growth, pivots, entrepreneurship, value creation, founder storiesTimestamps:(00:00:00) Intro(00:01:47) Who is Chris Saad?(00:02:30) Pablo's Story(00:05:53) The Core to Early Stage is PMF(00:09:07) Step 1: Research Mode(00:16:44) Step 2: Only the Insanely Focused Survive(00:23:46) Step 3: Be in the Market to Win the Market(00:32:57) Step 4: Forget Growth, Find Value(00:37:59) Step 5: Pivot Harder and Faster(00:45:45) RecapSend me a message to let me know what you think!

Gusto is a $9.5B startup that does $500M ARR. Josh built an absolute monster of a company-- and it all started with payroll software for SMBs. Not just that, he started by servicing only new tech startups that were based in California. It was exceptionally niche, and it worked.After YC, he raised a $6M seed round from tier 1 angels, back when large seed rounds were not at all common. But, unlike others, he didn't spend the money. He kept his team small as they iterated on the product. By the time they raised their $20M Series A, they were  only 10-15 people. Gusto is now a $9.5B startup doing $500M ARR. Here's the story of how they got started, gained initial traction, and took off.Why you should listen:Why starting super small can lead to massive outcomes.Why you need a huge, no-brainer pain point to succeed.How to use early customer interviews to deeply understand your ICP. Why small teams allow for faster decision-making and execution.Why deep passion about the problem set is so important.KeywordsGusto, Josh Reeves, entrepreneurship, startup, payroll, small business, Y Combinator, business model, innovation, technology, fundraising, startup, product-market fit, team building, customer satisfaction, growth strategy, small business, Gusto, entrepreneurship, SaaSSend me a message to let me know what you think!

We go through the top 5 product-market fit lessons I've learned from speaking to well over 100+ founders on this show over the last 3 years.These are the top 5 things you should keep top of mind going into 2025.Why you should listen:Small teams outperform larger ones in early stages.Paying employees well is needed to build A+ teams.Go all-in on fundraising to do it faster. Mind your burn rate to maintain flexibility.Creating undeniable value is essential for growth.Keywordsproduct market fit, startup strategies, fundraising, small teams, value creation, entrepreneurship, founder insights, business growth, early stage startups, team dynamicsSend me a message to let me know what you think!