Season 4
He raised $250K, had thousands of users—but here's what he'd do diffe…
Darius started an EdTech startup to help users of online courses collaborate with each other. It blew up during COVID when everyone felt isolated. It gained thousands of users. They were engaged. They came back to use the pla...
Stripe bought his startup for $1.1B—just 2.5 years after he quit his …
Zach was burned out after a decade of working at top roles in Coinbase, Square and Brex. He quit with no startup idea-- and then, he went right back in. Given their background, Zach and his co-founder quickly raised an $8M se...
The 5 Steps to Product-Market Fit w/ Chris Saad, ex-Head of Product a…
We took examples from the last 100 episodes and built a clear, 5 step path to finding product market fit: 1.Before Startup Mode, There’s Research Mode —> Become an expert to find problems worth solving. 2.Only the Insanely Fo...
How Gusto’s $10B founder raised $6M, built a team of 5—& hit $5M ARR …
Gusto is a $9.5B startup that does $500M ARR. Josh built an absolute monster of a company-- and it all started with payroll software for SMBs. Not just that, he started by servicing only new tech startups that were based in C...
The top 5 early-stage startup lessons for 2025
We go through the top 5 product-market fit lessons I've learned from speaking to well over 100+ founders on this show over the last 3 years. These are the top 5 things you should keep top of mind going into 2025. Why you should listen: Small teams outperform larger ones in early stages.Paying emplo…