A Product Market Fit Show | Startup Podcast for Founders

Bob is a serial entrepreneur who founded MobileIron, grew it to $150M in revenue, and took it public. Now, he's back with his fourth startup, BlueRock, tackling the next massive wave: agentic AI security.
In this episode, Bob breaks down the distinct difference between finding Product-Market Fit and finding Go-To-Market Fit—and why confusing the two can kill your company. 
He shares the exact questions he asked early customers to pivot from a generic mobile idea to a billion-dollar enterprise solution, the painful transition from founder-led sales to a repeatable playbook, and why he believes agentic AI is the "mobile wave" all over again.
Why You Should Listen
Why asking "what else is bothering you?" can uncover real pain points.
Why finding Product-Market Fit might actually increase your burn rate.
Why founder-led sales often fail to scale and what to do about it.
How to use a "Deal Grind" session to turn anecdotal sales wins into a scientific Go-To-Market machine.
Why identifying the right tech wave matters more than your initial idea.
Keywords
startup podcast, startup podcast for founders, product market fit, go to market fit, enterprise sales, founder led sales, mobileiron, agentic AI, cybersecurity startup, bob tinker
00:00:00 Intro
00:03:17 Talk to Customers Before Writing Code
00:15:28 Why Finding PMF Can Increase Burn Without Growth
00:17:51 The Founder "Magic Pixie Dust" Trap
00:25:34 The Deal Grind Exercise
00:31:43 From 1M to 80M ARR in 4 Years
00:32:54 Why Agentic AI is the Next Mobile Wave
00:38:30 The Famous Sequoia Tombstone Meeting
00:40:17 The Magic Question: What Else is Bothering You?
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In less than 12 months, Shahar went from an idea to a $30M Series A and a team of 40. He didn't sell another AI tool—he built an AI-first service that replaced expensive human consultants in the massive pen-testing market.
In this episode, Shahar breaks down the "Service-as-Software" playbook that allowed him to hit $1M ARR in just three months. He reveals how to convert design partners into paying customers before the product is finished, why he refuses to sell to service providers, and how to achieve a 40% SQL-to-Close rate in the enterprise.
Why You Should Listen
How to hit $1M ARR in a single quarter with zero marketing spend.
Why asking "Would you use this?" is useless and the one question that actually validates demand.
Why "Service-as-Software" is the single best business model for AI startups
How to maintain a 100% win rate against competitors in live bake-offs.
The ultimate litmus test for knowing if you have true Product-Market Fit.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, agentic AI, cybersecurity startup, B2B sales strategy, service as software, rapid scaling, Felicis
00:00:00 Intro
00:04:06 Why Manual Pen Testing is Broken
00:15:42 Ideation and The Wallet Test
00:22:38 How to Convert Design Partners to Paid
00:28:05 40 Percent SQL to Close Rate
00:33:14 The Service as Software Business Model
00:46:06 Hitting 1M ARR in One Quarter
00:48:50 Raising a 30M Series A from Felicis
00:50:01 The Turn It Off PMF Test
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Ashwin built a $1.5B company in two years. He didn't do it with a massive team or a complex 5-year roadmap. He did it by ignoring "strategy" and talking to 100+ buyers until he found a problem so painful they would pay six figures for a solution that didn't fully exist yet.
In this episode, Ashwin breaks down the exact playbook Decagon used to go from zero to unicorn. He reveals why he refused to hire anyone until $1M ARR, how to differentiate in a crowded AI market, and why your customers are the only roadmap you’ll ever need.
Why You Should Listen
How to hit $1M ARR in 6 months with just two founders and zero employees.
The "Willingness to Pay" test: How to know if a customer will sign a $150k check.
Why "over-thinking" your strategy is the fastest way to kill your startup.
How to close massive enterprise deals before you have a full product.
Why going vertical is often the wrong move for AI startups.
Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, B2B sales, enterprise sales, AI startup, customer discovery, pricing strategy, early stage growth
00:00:00 Intro
00:02:56 Selling His First AI Startup to Scale
00:09:11 Why Founders Over Intellectualize Strategy
00:13:48 How to Get 100 Customer Interviews
00:15:10 The 150k Willingness to Pay Test
00:21:05 Hitting 1M ARR with Zero Employees
00:25:09 Ignoring Scalability to Win Early Customers
00:31:43 Defensibility in the Gen AI Era
00:39:42 Mocking APIs to Close Enterprise Deals
00:42:58 The Moment of True Product Market Fit
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Jake founded Serval in April 2024— by Dec 2025 he'd raised a $75M Series B from Sequoia at a $1B valuation.
He didn't look for a "wedge" or a "niche." He looked at ServiceNow—a $160B, 20+ year-old incumbent that everyone IT team relies on—and rebuilt it from the ground up in a YEAR. 
In this episode, Jake reveals the audacity behind building a full-platform replacement from Day 1, why he spent months building in the dark with zero revenue, and how he achieved a 50% demo-to-close rate on six-figure enterprise deals.
Why You Should Listen
How to go from incorporation to a $1B valuation in just 18 months.
The psychological shift in sales calls that proves PMF.
How to build a demo so compelling that 50% buy on the spot.
Why you no longer need to find a small wedge to win post Gen AI.
The specific question that stops customers from giving you generic feedback.
Keywords
startup podcast, startup podcast for founders, hypergrowth, zero to one, unicorn startup, Sequoia Capital, replacing legacy software, enterprise sales strategy, ServiceNow competitor, Jake Stauch
00:00:00 Intro
00:03:25 Why "Hair on Fire" Problems Matter
00:06:58 Learning What Winning Feels Like at Verkada
00:14:05 100+ Customer Discovery Calls
00:18:12 The One Question That Unlocks Real Pain
00:23:48 Why No-Code Workflows Fail
00:28:45 Taking Risks on AI Model Improvements
00:35:49 From $0 to Six-Figure ACVs in 6 Months
00:39:00 The Strategy to Rip and Replace ServiceNow
00:47:30 The "Rounding Up" Signal of PMF
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Siqi was the CEO of a hot startup doing $20M a year. Then COVID hit. Overnight, revenue went to zero. He had to lay off 95% of his staff. In the chaos of trying to save the company using broken spreadsheets, he found his next big idea: Runway.
But the path wasn't a straight line. Siqi spent four years building the product before fully launching. 
In this episode, he breaks down why product taste matters more than A/B testing, and the insane viral launch strategy that overwhelmed his sales team and generated $1M ARR in a single month.
Why You Should Listen
How a viral marketing campaign added $1M ARR in just 30 days.
Why "user love" is a trap.
Why it took 4 years of building in the dark to create the "Figma for Finance."
How to mentally survive losing 95% of your revenue and staff overnight.
Why startups are a test of stamina, not intelligence.
Keywords
startup podcast, startup podcast for founders, product market fit, viral marketing, fintech, financial modeling, finding pmf, startup growth, founder stories, Siqi Chen
00:00:00 Intro
00:04:09 The COVID Crash: From $20M to $0 ARR
00:20:36 The V1 Trap: Great UI, Zero Willingness to Pay
00:36:25 The 4 Year Build: Comparing to Figma and Notion
00:46:53 The Viral Time Locked Jacket Launch
00:53:04 Adding 1M ARR in 30 Days
00:53:45 The PMF Moment
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