In this episode, Rich breaks down the wild story of Fathom's launch. He reveals how they secured a prime spot on the Zoom Marketplace and generated 100,000 signups in 30 days—only to realize 99.9% of them were useless.

He discusses the pivot to monetization when the market crashed, how to design a product for viral loops, and why staying in private beta for 10 months was the best decision he ever made.

Why You Should Listen

• Why getting 100,000 signups in a single month nearly killed the company.
• How to use the "Iceberg Strategy" to build a defensible moat.
• Why you should attack the "800-pound gorilla" incumbent.
• How to hit $100k ARR by selling a roadmap that doesn't exist yet.
• The "Visible Feature" mechanic that drives zero-cost viral growth in B2B.

Keywords

startup podcast, startup podcast for founders, viral growth, product market fit, AI startup, freemium strategy, Zoom marketplace, PLG, B2B sales, Fathom

00:00:00 Intro
00:03:14 Why Sales Reps Hated Gong
00:07:54 Betting on Transcription Costs Going to Zero
00:11:52 The 10 Month Private Beta Strategy
00:17:46 The Zoom Marketplace Launch
00:19:52 100k Signups and Zero Growth
00:26:39 Selling a Roadmap to Hit 100k ARR
00:33:53 The Viral Loop of Visible Bots
00:36:12 Why Enterprise Sales Was a Trap
00:39:51 The Moment of True Product Market Fit

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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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The startup game has completely changed. If you are still building with the 2018-2022 B2B SaaS playbook, you are already behind.

In this episode, we break down exactly how the GenAI shift has altered value creation, competition, and business models forever. This isn’t just about adding AI to your product—it’s about rethinking your entire reason to exist.

If you want to know where the massive, uncrowded opportunities are right now (and why Service-as-Software is the next gold rush), this is your blueprint.

Why You Should Listen

• Why "incremental value" startups are no longer fundable.
• The 3 new threats killing your "time-to-market" moat.
• Why the B2B SaaS playbook is dead and what’s replacing it.
• The massive "Service-as-Software" opportunity most founders are missing.
• Moving beyond "per seat" pricing: The new revenue models winning today.

Keywords

startup podcast, startup podcast for founders, GenAI startups, product market fit, service as software, B2B SaaS, AI business models, startup competition, seed stage, founder advice

00:00:00 Intro

00:01:57 Pre-Gen AI vs Post-Gen AI Eras

00:03:23 The Trap of Incremental Value Props

00:06:58 Gen AI Unlocks Undeniable Value

00:08:50 The New Triple Threat Competition

00:11:50 Why Time in Market Is Dead

00:13:14 Cycle Speed Is the Only Moat Left

00:15:00 Rethinking B2B SaaS Business Models

00:16:45 The Service as Software Opportunity

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For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3.

Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.

Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.

But then things changed:

2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR

Huntress is valued at $2B.

The investors who backed his $1M bridge are up 140x.

Now every VC wants to invest—and Kyle's the one saying 'no'.

Why you should listen:

How to know whether you should keep going or quit.
What it takes to get through the first few years at a bootstrapped startup.
Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
How starting a startup can impact your personal life and relationships.
How to work with partners to sell to long tail SMB customers.
Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth

Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice

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