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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