A Product Market Fit Show | Startup Podcast for Founders

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 Intro
• 00:02:03 Product Market Fit Three Times
• 00:06:21 From Berlin Wi-Fi to Stripe for Telecom
• 00:16:10 No Carrier Would Talk to Them
• 00:19:35 Kids' Smartwatches With 40% Returns
• 00:24:11 Why Fintechs Want to Sell Phone Plans
• 00:30:22 Telling a 15-Year Story to VCs
• 00:37:18 Statesmanship, Not Salesmanship
• 00:43:33 Stay in Sales Longer Than You Should

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Daniel Saks built AppDirect into a marketplace moving upwards of $10B a year in gross merchandise value. 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 Intro
• 00:02:28 Product Market Fit Is Magnetic Momentum
• 00:04:44 The Bell Launch Nobody Came To
• 00:14:24 Leaving the Company He Built
• 00:16:27 Training a Model on What Outbound Works
• 00:26:36 Start With a Living TAM Map
• 00:34:09 Who Gets Your Time, Who Gets Autopilot
• 00:39:50 The Response Rates to Actually Expect
• 00:49:26 The Biggest Outbound Mistake

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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 Intro
• 00:03:46 20 Deals in a Row
• 00:06:39 The 20-Minute SLA
• 00:11:15 Banker, Founder, First-Time CEO
• 00:16:07 Quitting With No Idea
• 00:26:26 SVB Crashed in Week One
• 00:33:08 What a 100-Hour Week Looks Like
• 00:44:56 Introducing Buyers to VCs
• 00:53:21 Getting 15 Banks to Go First
• 00:59:29 Swag Selling and Post-It Notes

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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 Intro
• 00:02:14 The Referrals That Proved PMF
• 00:05:36 How to Actually Drive Word of Mouth
• 00:07:15 The Idea Born Inside McKinsey Legal
• 00:11:38 Why Legal Never Got a CRM
• 00:17:07 Quitting and Raising From Sequoia the Same Day
• 00:25:53 The Design Partners They Fired
• 00:30:20 Hiring an AE Before You Have PMF
• 00:40:32 Two Dinners a Week That Fill the Pipeline
• 00:47:03 Go Spend Time With Customers in Person

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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 Intro
• 00:03:09 The App He Built In A Week
• 00:06:38 $1M In Two Months
• 00:08:25 Facebook Shuts It Down
• 00:15:39 The Pivots Before Mode
• 00:20:42 32,481% Growth To The Fast 500
• 00:26:26 Revenue Concentration Nearly Kills It
• 00:31:50 How Paying People To Play Works
• 00:37:53 Creator-Led Growth For $30 A Video
• 00:47:09 What Makes A Crowdfund Work

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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 Intro
• 00:02:27 The Customers Who Were Hopping Mad
• 00:07:41 20M Users, Almost No Retention
• 00:09:27 When Your Business Works But Won't Inflect
• 00:11:24 Why His Board Said Burn the Boats
• 00:18:29 Turning Off the Product Before Knowing What's Next
• 00:22:13 Reinventing the System of Record
• 00:30:25 How to Sell to YC Founders
• 00:36:04 Making a Launch Video Hit a Million Views
• 00:44:08 The One Piece of Advice

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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 Intro
• 00:02:05 The Morgan Stanley Deal That Proved PMF
• 00:08:32 A 401k So Bad It Started a Company
• 00:10:23 Building V1 in a Regulated Industry
• 00:17:07 Turning Advisors Into a Sales Channel
• 00:23:57 Raising an A on $200K of Revenue
• 00:31:16 Too Boring for the Crypto Bull Market
• 00:38:45 Losing JP Morgan, Then Winning It Back
• 00:43:23 Never Regret Firing Too Soon

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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 Intro
• 00:02:04 The Side Tool Everyone Wanted
• 00:04:26 $350K in Five Weeks
• 00:05:42 AI for Lawyers Before AI Worked
• 00:12:44 Stuck at $800K
• 00:13:43 Choosing Finance Over Legal
• 00:17:40 The 30 and 100 Rule
• 00:24:59 Selling the $10M Business
• 00:32:17 Building a Company Data Brain
• 00:40:01 Nine of Ten Bets Fail

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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 Intro
• 00:02:11 Why Healthcare Has No Shortcuts
• 00:05:34 What Judi Health Actually Does
• 00:11:27 Opacity As A Business Strategy
• 00:15:12 Bootstrapping In A Regulated Market
• 00:21:50 Selling The First Risky Customers
• 00:27:15 Winning Bids When Rivals Look Free
• 00:33:37 Zero Marketing And A Service Moat
• 00:42:20 Hiring For Mission And A Players
• 00:52:35 Founder Advice On Focus And Discipline

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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 Intro
• 00:02:23 $1.5M of Enterprise Revenue in One Month
• 00:04:22 Why Enterprises Couldn't Say No
• 00:06:04 What Endra Actually Does
• 00:08:27 Law School to CCTV Cameras
• 00:12:06 Recruiting Two Goldman Engineers
• 00:17:11 Finding Users in Reddit Threads
• 00:26:02 $4M, $20M, Then $50M From a16z
• 00:35:00 Spending $150K on Brand Before a Product
• 00:40:11 The Hiring Principles Manual

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