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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