He thought his startup would fail—then grew to $100M ARR. | Rick Song, Co-founder of Persona

Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded.

In this episode, Rick reveals how a casual project with zero expectations turned into a billion-dollar business, why early-stage startups should avoid hyper-optimization, and the secrets he learned at Square about identity fraud that became his breakthrough.

If you want to challenge the typical startup narrative, this one’s a must-listen.

Why You Should Listen

• How Rick Song took Persona from $0 to $100M ARR without believing in product-market fit.
• Why obsessing over optimization might be killing your startup.
• How to think differently about fundraising—Rick raised $2.4M without even trying.
• The real truth about what decisions actually matter in your early days.

Keywords

product market fit, startup advice, early-stage founders, fundraising, hyper-optimization, identity fraud, Persona, Rick Song, Square, founder mindset

00:00:00 Intro

00:08:07 Finding Persona’s First Customer

00:17:56 How to Quit a Successful Job for a Risky Startup

00:26:54 Early Product Strategy

00:37:40 Hiring the First Employees Without Selling the Dream

00:47:54 Fundraising Without Even Trying

00:56:55 Hyper-Optimization is Hurting Your Startup Decisions

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