A Product Market Fit Show | Startup Podcast for Founders

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 Intro
00:03:18 The Brand That Flew Him to Dallas
00:06:59 From Review Software to Delightree
00:12:10 A Free App Nobody Used
00:13:31 Ruthless Customer Qualification
00:16:56 From Ops Binder to TikTok-Style Training
00:22:50 More Revenue in One Quarter Than Two Years
00:26:52 A New Demo After Every Call
00:30:27 Which Feature Requests to Ignore
00:37:07 The Cold Email With Their Logo
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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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