Advertise on podcast: A Product Market Fit Show | Startup Podcast for Founders

Rahul ran a sleep clinic that lived and died by insurance paperwork. He sold it, then built the tool he wished it had. Two customers signed on before Assured was even incorporated. Five months in, four new customers landed in one week and the founders couldn't onboard them all. Twelve months in, they hit $1M ARR. Assured just raised a $19M Series A. In this episode, Rahul breaks down why his team skipped AI SDRs for six human BDRs making 150 to 200 calls a day, how doing discovery before the demo took their close rate from 18% to 40%, and why landing one small logo unlocks a whole medical specialty. Why You Should Listen Why an 8% cold call pickup rate made human BDRs the right call.How human in the loop lets a V1 hit 100% accuracy from day one.Why the same ROI pitch wins one buyer and kills the deal with another.How to turn a long deployment into urgency that closes the deal.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Assured, Rahul Shivkumar, healthcare AI, AI agents, provider credentialing, payer enrollment, revenue cycle management, cold calling, BDR compensation, discovery calls, forward deployed engineering Chapters 00:00:00 Intro00:02:21 Four New Customers in One Week00:05:14 From Dawn Health to Assured00:11:36 Starting at the Front Door of Revenue Cycle00:18:00 Human in the Loop, 100% Accuracy00:21:28 The ROI Math, and When It Falls Flat00:30:25 $1M ARR and the Power of One Logo00:34:27 Why Human BDRs Beat AI SDRs00:48:20 Discovery Before the Demo00:51:27 Getting Stalled Deals Over the LineSend me a message to let me know what you think!

Tushar gave his app away for free. It spread to 200 locations. Almost nobody used it, and nobody paid a single dollar. So he started charging from day one, with a one-month pilot that rolled into a full annual contract. In Q4 2025, his team closed more revenue than in the two years before. Delightree just raised $25M. In this episode, Tushar breaks down the three questions he used to qualify every customer, how turning a dusty ops binder into TikTok-style training became his biggest source of leads, and why his best cold email was a screenshot of the prospect's own logo. Why You Should Listen Why free pilots kill real feedback, and what to offer instead.How to qualify a customer on pain, budget, and outcome before you sell.Why you should ignore feature requests that muddy your go-to-market.How a screenshot with the prospect's logo beat every other cold email.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Delightree, Tushar Mishra, franchise software, frontline employees, customer onboarding, customer qualification, outbound sales, cold email, net revenue retention, AI training Chapters 00:00:00 Intro00:03:18 The Brand That Flew Him to Dallas00:06:59 From Review Software to Delightree00:12:10 A Free App Nobody Used00:13:31 Ruthless Customer Qualification00:16:56 From Ops Binder to TikTok-Style Training00:22:50 More Revenue in One Quarter Than Two Years00:26:52 A New Demo After Every Call00:30:27 Which Feature Requests to Ignore00:37:07 The Cold Email With Their LogoSend me a message to let me know what you think!

Hermann wanted to build Stripe for phone plans. Every carrier said no and investors passed. So he plugged into an aggregator with terrible economics and sold to kids' smartwatch makers losing 30 to 40% of devices to returns. That niche paid for his seed and Series A. Then AT&T opened the door. Today Gigs powers phone plans for Revolut, Klarna, Nubank and Cash App and wins 90% of the deals it goes after. In this episode, Hermann breaks down why a small niche with a sharp pain point beats a big market with a mild one, how a founder tells a 15-year story to investors without losing them, and why landing an enterprise customer is statesmanship, not salesmanship. Why You Should Listen Why 30 to 40% return rates made kids' smartwatch makers the perfect first customer.How building on an aggregator with no margin got Gigs its first deal with AT&T.Why you should borrow another company's story until you have your own.How working every layer of an enterprise at once wins 90% of deals.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Gigs, Hermann Frank, embedded telecom, eSIM, telecom API, fintech, enterprise sales, founder led sales, niche markets, Y Combinator, Stripe for telecom, storytelling for fundraising Chapters 00:00:00 Intro00:02:03 Product Market Fit Three Times00:06:21 From Berlin Wi-Fi to Stripe for Telecom00:16:10 No Carrier Would Talk to Them00:19:35 Kids' Smartwatches With 40% Returns00:24:11 Why Fintechs Want to Sell Phone Plans00:30:22 Telling a 15-Year Story to VCs00:37:18 Statesmanship, Not Salesmanship00:43:33 Stay in Sales Longer Than You ShouldSend me a message to let me know what you think!

Daniel Saks built AppDirect into a marketplace that's nearing $1B in gross annual recurring revenue. Now he runs Landbase, an AI go-to-market company with data on 40 million startups, and it just raised a $30M Series A. So when he talks about cold outbound, he is not guessing. He is reading what actually happens across millions of messages. He also spent two years in a windowless room building an app store for Bell Canada that launched to crickets. Harley from Shopify messaged him: the Bell business app store has less traffic than my intern's blog. In this episode, Daniel breaks down what response rates on cold email actually look like today, how to build a living TAM map instead of paying a consulting firm a few hundred thousand for a dead one, and why three touches get you 90% of the result while five gets you flagged as spam. Why You Should Listen Why product market fit is never won once, only re-won in each new niche.How a 2% email response rate becomes 8-10% on a tight enough list.Why you should not run outbound at all until people can look you up.How to hand an agent your CRM and call notes so it tells you who to call today.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Landbase, Daniel Saks, AppDirect, outbound sales, cold email, AI SDR, go-to-market, TAM mapping, agentic AI, sales development, B2B marketplaces Chapters 00:00:00 Intro00:02:28 Product Market Fit Is Magnetic Momentum00:04:44 The Bell Launch Nobody Came To00:14:24 Leaving the Company He Built00:16:27 Training a Model on What Outbound Works00:26:36 Start With a Living TAM Map00:34:09 Who Gets Your Time, Who Gets Autopilot00:39:50 The Response Rates to Actually Expect00:49:26 The Biggest Outbound MistakeSend me a message to let me know what you think!

Jonathan quit his job in early 2023 with no idea and no co-founder. Tim agreed to join only if he raised $3M. He lined up 75 investor meetings a month in advance. SVB crashed on day four and 40% of his meetings canceled. He closed the round anyway, then won 20 deals in a row, one of them a seven-figure deal with FIS. Baselayer just raised a $20M Series A. In this episode, Jonathan breaks down the 20-minute reply rule he holds every employee to, why he asks buyers if they have ever wanted to be a founder and then introduces them to VCs, and what a 100-hour week actually looks like when your calendar shows 40 to 60 hours of meetings. Why You Should Listen Why replying in two minutes lets you get away with saying almost nothing.How introducing 40 buyers to VCs turned into 40 customers.Why he pitched 15 banks at once so nobody had to go first.How to reach out to everyone you have ever met without it feeling cold.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Baselayer, Jonathan Awad, business identity verification, KYB, fraud consortium, fintech sales, enterprise sales, top of funnel, customer support, founder-led sales, seed fundraising, SVB collapse Chapters 00:00:00 Intro00:03:46 20 Deals in a Row00:06:39 The 20-Minute SLA00:11:15 Banker, Founder, First-Time CEO00:16:07 Quitting With No Idea00:26:26 SVB Crashed in Week One00:33:08 What a 100-Hour Week Looks Like00:44:56 Introducing Buyers to VCs00:53:21 Getting 15 Banks to Go First00:59:29 Swag Selling and Post-It NotesSend me a message to let me know what you think!

Most investors told Nick not to hire a salesperson before he had product market fit. He hired the top rep in legal tech anyway and called him a product market fit finder. That rep signed a paid five-year deal in his first week, over lunch. By the time Sandstone came out of stealth, they had done hundreds of demos and had $10M+ of pipeline waiting. Sandstone just raised a $30M Series A. In this episode, Nick breaks down why the intros he never asked for were the moment he knew PMF was real, how sitting next to customers and watching them work turned into their biggest integrations, and why they fired design partners whose problems did not match the market. Why You Should Listen Why intros you never asked for are the truest early signal of PMF.How hiring an elite AE pre-PMF bought them a product market fit finder, not a quota.Why saying yes to every design partner request leads you away from the market.How two or three dinners a week convert prospects to demos almost every time.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Sandstone, Nick Fleisher, legal tech, in-house legal teams, AI for legal, contract lifecycle management, enterprise sales, design partners, hiring an AE, founder-led sales, word of mouth referrals Chapters 00:00:00 Intro00:02:14 The Referrals That Proved PMF00:05:36 How to Actually Drive Word of Mouth00:07:15 The Idea Born Inside McKinsey Legal00:11:38 Why Legal Never Got a CRM00:17:07 Quitting and Raising From Sequoia the Same Day00:25:53 The Design Partners They Fired00:30:20 Hiring an AE Before You Have PMF00:40:32 Two Dinners a Week That Fill the Pipeline00:47:03 Go Spend Time With Customers in PersonSend me a message to let me know what you think!

Dan's first app made over $1M in two months. Then Facebook sent a cease and desist and killed it. His next company, Mode Mobile, grew revenue 32,481% in three years and ranked #1 on the Deloitte Fast 500. Then his crypto advertisers went bankrupt, revenue fell from $25M to $8M, and he cut half his staff. No VC wanted a declining Series B. So he raised $5M from his own users in three months—then $75M more. In this episode, Dan breaks down how paying people to use their phone actually makes money, why revenue concentration and not growth is what nearly killed Mode, and how to run a creator-led marketing campaign at $30 a video. Why You Should Listen Why the product market fit that feels insane is often the kind that dies fastest.How building on someone else's API cost him two different companies.Why extending your payback period is the fastest way to run out of cash.How to know within $20K to $30K whether creator-led marketing works for you.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Mode Mobile, Dan Novaes, crowdfunding, Reg A, consumer apps, rewards apps, creator-led marketing, UGC creators, user acquisition, revenue concentration, Android apps Chapters 00:00:00 Intro00:03:09 The App He Built In A Week00:06:38 $1M In Two Months00:08:25 Facebook Shuts It Down00:15:39 The Pivots Before Mode00:20:42 32,481% Growth To The Fast 50000:26:26 Revenue Concentration Nearly Kills It00:31:50 How Paying People To Play Works00:37:53 Creator-Led Growth For $30 A Video00:47:09 What Makes A Crowdfund WorkSend me a message to let me know what you think!

Keith raised a $43M Series B for Tome. The product had 20 million users. But retention was terrible and nobody cared enough to complain. So he turned it off before he knew what he'd build next, went from 70 people to 7, and started over. Lightfield just closed a $47M Series A. In this episode, Keith breaks down how he knew Tome would never grow up, why customers lighting up your Slack at 3am is the signal you actually want, and the exact playbook he used to sell an AI-native CRM to YC founders before he charged them a dollar. Why You Should Listen Why angry customers are a better signal than 20 million happy ones.How to know when optimizing metrics will never re-inflect your business.Why you have to kill the old product before you can find the new one.How to win founders with free software and events instead of cold email.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Lightfield, Keith Peiris, Tome, pivoting a startup, AI native CRM, agentic system of record, cutting burn, go-to-market, selling to YC founders, launch videos, B2B SaaS Chapters 00:00:00 Intro00:02:27 The Customers Who Were Hopping Mad00:07:41 20M Users, Almost No Retention00:09:27 When Your Business Works But Won't Inflect00:11:24 Why His Board Said Burn the Boats00:18:29 Turning Off the Product Before Knowing What's Next00:22:13 Reinventing the System of Record00:30:25 How to Sell to YC Founders00:36:04 Making a Launch Video Hit a Million Views00:44:08 The One Piece of AdviceSend me a message to let me know what you think!

Aaron started Vestwell in 2016. Two years in, he had $500K in ARR and an investor asking if it would ever make money. During the 2021 bull market, VCs told him 401ks were too boring—they were busy chasing crypto. Then Morgan Stanley signed. Today Vestwell has 2.5 million people saving on the platform, over $200M in ARR, and just raised $385M at a $2B valuation. In this episode, Aaron breaks down why he white-labeled everything instead of building his own brand, how losing the JP Morgan bid as a 40-person startup still turned into one of his largest partnerships, and how a methodical cap table let him raise a Series A on a couple hundred thousand in revenue. Why You Should Listen Why letting your customers keep their brand beats competing with them.How to raise a Series A with only a few hundred thousand in ARR.Why losing an enterprise deal is the start of the sale, not the end.Why you never regret firing someone too soon.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Vestwell, Aaron Schumm, fintech, 401k, retirement savings, enterprise sales, channel partnerships, white label software, Series A fundraising, Morgan Stanley Chapters 00:00:00 Intro00:02:05 The Morgan Stanley Deal That Proved PMF00:08:32 A 401k So Bad It Started a Company00:10:23 Building V1 in a Regulated Industry00:17:07 Turning Advisors Into a Sales Channel00:23:57 Raising an A on $200K of Revenue00:31:16 Too Boring for the Crypto Bull Market00:38:45 Losing JP Morgan, Then Winning It Back00:43:23 Never Regret Firing Too SoonSend me a message to let me know what you think!

Andrew spent two and a half years selling AI contract review to lawyers. It stalled at $800K. He rebuilt the company around finance teams and grew that to $10M. Then he demoed a little internal tool on the side at his own conference, and nobody wanted to talk about anything else. It did $350K in five weeks. He sold the $10M business and went all in on the side tool—Within went from zero to nearly $20M in 18 months. In this episode, Andrew breaks down the 30-and-100 rule he uses to validate every idea, how he turned every customer conversation into a database that tells him what to build next, and why nine out of ten experiments have to fail. Why You Should Listen Why 30 conversations validate an idea and 100 customers reveal product market fit.Why the thing everyone asks about matters more than the thing you launched.How to tell that slow growth is a market problem, not a go-to-market problem.How to run four bets a quarter with a kill metric on every one.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Within, Klarity, Andrew Antos, enterprise AI, AI transformation, pivoting a startup, enterprise sales, legal tech, finance automation, AI agents, customer discovery, voice of customer Chapters 00:00:00 Intro00:02:04 The Side Tool Everyone Wanted00:04:26 $350K in Five Weeks00:05:42 AI for Lawyers Before AI Worked00:12:44 Stuck at $800K00:13:43 Choosing Finance Over Legal00:17:40 The 30 and 100 Rule00:24:59 Selling the $10M Business00:32:17 Building a Company Data Brain00:40:01 Nine of Ten Bets FailSend me a message to let me know what you think!

AJ spent two years selling health benefits with no customers and no references. His competitors told buyers their service was free. He charged a flat fee and told the truth about where the money actually went. Two years in, at $10M ARR, a Fortune 500 company called him. Judi Health just raised $400M at a $3.25B valuation. In this episode, AJ breaks down how he beat three Fortune 15 giants by operating 70% more efficiently, why he spent zero on marketing for two years and let customers sell for him, and the one hiring signal he refuses to ask about directly. Why You Should Listen Why $10M ARR still felt like nothing against three Fortune 15 competitors.How to sell healthcare when your answer to "who are your customers" is "just you."Why he spent $0 on marketing and made customers the brand ambassadors.How he spots A players without ever asking them about the mission.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Judi Health, Capital Rx, AJ Loiacono, pharmacy benefit management, PBM, healthcare startup, enterprise sales, transparent pricing, bootstrapping, self-insured employers, hiring for mission Chapters 00:00:00 Intro00:02:11 Why Healthcare Has No Shortcuts00:05:34 What Judi Health Actually Does00:11:27 Opacity As A Business Strategy00:15:12 Bootstrapping In A Regulated Market00:21:50 Selling The First Risky Customers00:27:15 Winning Bids When Rivals Look Free00:33:37 Zero Marketing And A Service Moat00:42:20 Hiring For Mission And A Players00:52:35 Founder Advice On Focus And DisciplineSend me a message to let me know what you think!

Niklas quit law school to install CCTV cameras in iPhone repair shops. Eight years later he sold that business to private equity at 26. Then he went after the most boring software in the world: the 1997 tool engineers use to design the wiring and plumbing inside buildings. He spent $150K on a website before he had a product and DM'd engineers on Reddit to find his first users. His first month of sales was $1.5M, all enterprise. Endra has now raised $75M, including a $50M Series A led by a16z. In this episode, Niklas breaks down why he spent $150K on brand before there was a product, how DMs in Reddit engineering threads turned into $300K enterprise contracts, and the hiring principles he used to screen the first 50 employees. Why You Should Listen Why spending $150K on brand before you have a product can be the right call.How DMs in Reddit threads turned into $300K enterprise contracts.Why your customer's competitors are your best sales channel.How to know when 80% output is actually enough to sell.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Endra, Niklas Lindgren, MEP engineering, AI for construction, vertical AI, enterprise sales, brand building, Reddit marketing, hiring principles, agentic design software Chapters 00:00:00 Intro00:02:23 $1.5M of Enterprise Revenue in One Month00:04:22 Why Enterprises Couldn't Say No00:06:04 What Endra Actually Does00:08:27 Law School to CCTV Cameras00:12:06 Recruiting Two Goldman Engineers00:17:11 Finding Users in Reddit Threads00:26:02 $4M, $20M, Then $50M From a16z00:35:00 Spending $150K on Brand Before a Product00:40:11 The Hiring Principles ManualSend me a message to let me know what you think!

Colin spent eight years building Looker into a $2.7B Google acquisition. Then he left to compete with his own product. He thought traction would take a month—it took nine. A hundred demos got him five verbally-committed customers, and he lost all five. So he spent two months killing bugs, went on one podcast, and won every single trial that came out of it. Omni just raised over $250M. In this episode, Colin breaks down how to tell the difference between a product that's genuinely better and one the market just doesn't want, why founding with $30M didn't stop them from staying stingy, and the LinkedIn playbook that turned 6,000 connections into a 90% response rate. Why You Should Listen Why losing every deal doesn't mean the idea is wrong—and how to know the difference.Why real differentiation shows up as "wow" moments in demos, not signed contracts.The LinkedIn social-selling playbook that built Omni's first pipeline.Why hiring sellers from your old industry hands you their Rolodex on day one.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Omni, Colin Zima, Looker, business intelligence, BI tools, enterprise SaaS, AI analytics, social selling, LinkedIn outbound, founder-led sales, innovator's dilemma Chapters 00:00:00 Intro00:01:58 The Moment of True Product Market Fit00:06:16 Losing All Five Deals and Doubling Down00:10:43 Leaving Looker to Compete With Looker00:17:39 Founding With $30M and Staying Stingy00:22:09 A Hundred Demos Before the Flywheel00:32:15 No Silver Bullet—Just Do More of Everything00:38:32 The LinkedIn Social-Selling Playbook00:46:07 Hiring the Best People You've Worked WithSend me a message to let me know what you think!

Rafael launched a crypto insurance product in 47 states, backed by a real carrier. Everyone told him it was genius. Nobody needed it. He shut it down with $2M left in the bank, fired almost everyone, and rebuilt with two engineers on $20K a month. Notch just raised $30M. In this episode, Rafael breaks down how a POC he entered through the back door turned into a seven-figure contract, why "isn't everyone doing this?" is the feedback you actually want, and how to tell whether an enterprise deal makes you a real company or just their dev shop. Why You Should Listen Why "that idea is genius" is a warning sign, not a compliment.How entering a POC last still made them the front runner.Why the enterprise deals that scale need zero customization.How to stop hiding your idea and go straight to your dream customers.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Notch, Rafael Broshi, AI agents, insurance technology, customer experience automation, regulated industries, enterprise sales, POC strategy, pivoting a startup, on-prem deployment Chapters 00:00:00 Intro00:02:00 The Moment of True Product Market Fit00:10:07 One Enterprise Deal or Ten00:15:24 A Genius Idea Nobody Needed00:24:33 Picking the Right Wave to Ride00:34:37 Down to $2M, Firing Almost Everyone00:41:48 Getting Enterprise to Take Your Call00:48:07 The POCs That Aren't Real POCsSend me a message to let me know what you think!

Ben and his co-founder had no product, no law enforcement background, and no pitch—just an offer to help detectives solve cases. One commander took a chance, handed them background checks, and said "let's see what you can do." They worked out of that police department every day for 18 months. Peregrine just raised $250M at a $6.8B valuation. In this episode, Ben breaks down how researching every police captain in the Bay Area landed their first design partner, why working as free crime analysts for 18 months was "the purest form of method acting," how forward-deployed engineers drove them from $1M to $3M to $10M ARR, and the 120% RFP prep that won a contract written for a billion-dollar competitor. Why You Should Listen Why doing your customer's job is the fastest path to product market fit.How two founders with no product convinced a police department to let them in.Why over-investing in deployment became a growth engine, not a margin problem.How obsessive research wins enterprise deals when you have zero credibility.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Peregrine, govtech, public safety technology, forward deployed engineers, selling to government, enterprise sales, data integration, design partners, Ben Rudolph Chapters 00:00:00 Intro00:01:07 The Moment of True Product Market Fit00:11:51 Getting a Police Department to Say Yes00:16:45 Slow Growth and Word of Mouth00:19:49 Forward-Deployed Engineers Before They Were Cool00:27:34 Cracking Government Go-To-Market00:34:08 Winning an RFP Written for Someone ElseSend me a message to let me know what you think!