Casey turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on category creation when everyone thought hackers were the enemy.

You'll learn about the exact moment he knew he had product-market fit, why he blew every pitch to top VCs until he reframed his vision, and how giving away 500 t-shirts did more for growth than any paid marketing.

If you're building a marketplace, creating a category, or just trying to figure out how to explain what you do—this is required listening.

Why You Should Listen:

• Master the 30-second Uber pitch test—Casey's framework for refining your message until anyone gets it.
• Learn why problem-solution fit without product-market fit is worthless
• Validate your marketplace with $500 and no code
• Why your network is your only real asset pre-Series A
• The surprising ROI of early brand marketing

Keywords: startup podcast, startup podcast for founders, marketplace startup, go-to-market strategy, product-market fit, category creation, B2B sales, early-stage fundraising, founder pitch, cybersecurity startup

00:00:00 Intro

00:01:36 From white label pen testing to the Bugcrowd idea

00:18:58 Testing with MailChimp and 5000 hackers signed up

00:21:46 Landing Google as customer in month four

00:24:24 Blowing every pitch meeting in Silicon Valley

00:33:21 The Uber pitch technique for simplifying the message

00:36:57 Early go-to-market tactics and hitting $1M

00:43:37 Open heart surgery and stepping back as CEO

Send me a message to let me know what you think!