In this episode of Burning the Ships, I sit down with Bryce Matheson—founder of Lender, a fast-growing software platform built specifically for private and hard money lenders. Bryce’s story is a perfect example of how real businesses are built: through trial and error, painful lessons, and the willingness to take action before everything feels “ready.”

We walk through Bryce’s journey from house hacking and rentals, to flipping homes, to losing money on a deal that changed everything—and ultimately to becoming a lender himself. Along the way, Bryce explains how his tech background naturally led him to build systems to solve his own problems, why most lending software misses the mark, and how Lender was born out of pure necessity rather than some grand startup vision.

This conversation goes deep into entrepreneurs ...