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 Hanslovan, founder of Huntress, faced brutal rejection, slept in his car, maxed out credit cards, and still crushed it. This episode is packed with raw lessons on fundraising, product-market fit, and why relentless hustle alone won’t save you. If you’re a founder chasing growth, stop everything and listen.

Why You Should Listen

• Learn exactly what top founders did to get from zero to $100M ARR
• Why chasing perfection won't work (and how to stop)
• The secret to surviving brutal fundraising rejections (over 60 VCs said no to Kyle)
• Why hustle culture isn’t enough—here’s what matters more

Keywords

product-market fit, startup fundraising, unicorn startups, founder hustle, lean startup method, scaling startups, early-stage growth, AI startups, SaaS growth, venture capital advice

Chapters

(00:00:00) Intro

(00:02:05) Quitting a Unicorn to Start Again

(00:05:09) From NSA Hacker to Startup Founder

(00:09:18) Ignoring the Lean Startup

(00:12:59) Knowing When to Launch

(00:16:32) Finding Product Market Fit

(00:18:01) Final Advice for Founders

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