Podcast Episodes

How he grew to $100M ARR—then exited for $460M. | Zuben Matthews, Founder of Brigit

Season 4 Episode 56

Zuben turned his personal experience with crippling overdraft fees into Brigit, a fintech he sold for $460 million after hitting $100M ARR. This episode gives early-stage founders the unfiltered trut…

Published on 2 months, 1 week ago

He Hit $3.5M ARR and Still Failed. Here’s His #1 Mistake. | Joseph Lee, Founder of Freshline

Season 4 Episode 57

Joseph built Freshline to $3.5 million in revenue and nearly $2 million raised. It looked like a marketplace success story—until it wasn’t. In this episode, Joe shares the hidden reasons marketplaces…

Published on 2 months, 1 week ago

1st-time founder raises $140M with $0 revenue—grows to 800 employees & profitable. | Andrew Rubin, Founder of Illumio

Season 4 Episode 54

Andrew Rubin raised $40M in 6 months before writing a single line of code—and another $100M before seeing his first dollar of revenue. Today, Illumio is valued at billions and counts Morgan Stanley a…

Published on 2 months, 2 weeks ago

PMF Observations: Why it doesn't matter how fast you get to $1M ARR

Season 4 Episode 53

Forget what you thought about early-stage growth. In this must-listen episode, you’ll hear firsthand how startup success truly happens—and spoiler alert, there’s no playbook. From companies like Carb…

Published on 2 months, 2 weeks ago

He went 7 years with no revenue— then grew to $100M ARR. | Rob Woollen, Co-Founder of Sigma

Season 4 Episode 52

Rob Woollen, founder of Sigma Computing, shares the unfiltered reality of going from 0 to $100M ARR. After spending seven years grinding without product-market fit, Sigma finally hit an inflection po…

Published on 2 months, 3 weeks ago

$10M Raised, 500K Users, but she still failed—here’s what went wrong | Benedetta Lucini, Founder of Oval Money

Season 4 Episode 51

This is the brutally honest startup story every founder needs to hear. Benedetta  shares how she built a fintech app to half a million users and raised $10M—yet still failed. 

You’ll learn why chasing…

Published on 2 months, 3 weeks ago

How $100B Mercado Libre got started—& why it almost went bankrupt after 9 months. | Hernan Kazah, Co-Founder Mercado Libre

Season 4 Episode 50

How do you build a $100B business without hypergrowth or endless funding rounds? Hernan Kazah co-founded Mercado Libre, the Latin American ecommerce giant, at the peak of the dot-com bubble. But when…

Published on 2 months, 4 weeks ago

PMF Observations: How 4 Founders Built Massive Startups Their Own Way

Season 4 Episode 49

Four founders prove you don’t need Silicon Valley, a technical degree, or a massive seed round to build a massive company. We go through the key observations from the last 4 episodes: How Skip create…

Published on 3 months ago

His AI Voice Startup grew to $10M ARR in 1 Year—after 3 Years Stuck at $500K | Jordan Dearsley, Founder of Vapi

Season 4 Episode 48

Jordan Dearsley spent 3 years building a startup stuck at $500K in revenue—then he burned it all down and moved to San Francisco. A year later, he was at $10M ARR. This episode walks through Jordan’s…

Published on 3 months ago

WebSummit Panel w/ Founders of Glean ($5B) and Huntress ($2B): What it takes to hit $100M ARR

Season 4 Episode 47

Two founders, two wildly different paths to $100M ARR: Arvind Jain, founder of Glean, walked away from a unicorn to start over—raising $15M without revenue and ignoring lean startup rules. Kyle Hansl…

Published on 3 months, 1 week ago