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 entrepreneurship, resilience, capital raising, lending risk, family sacrifice, and building tools that actually serve real operators. If you’re in real estate, private lending, tech, or trying to build a scalable business without losing your sanity, this episode is packed with real-world insight.

Key Talking Points of the Episode

00:00 The internal struggle every entrepreneur faces: work vs. family guilt

01:16 Introducing Bryce Matheson and his move from Idaho to Arizona

02:52 How Bryce and I first connected through private lending

04:19 Early entrepreneurial instincts and selling candy as a kid

05:21 Starting the “traditional” path: college, tech job, and early rentals

06:21 Buying his first house in 2016 and accidentally house hacking

07:17 Scaling rentals, then burning out as a landlord

07:55 Transitioning into flipping houses—and why they loved it

08:38 The flip that went wrong during COVID and lost $50K

09:59 The moment Bryce realized: “I need to be the bank”

11:05 Moving into private lending with his own capital

12:32 Why underwriting is easier when you’ve flipped houses yourself

14:21 Seeing operational gaps and naturally building software to fix them

15:32 Building and selling an early QuickBooks-style tool

17:02 Are entrepreneurs born or built? Bryce’s take

18:59 The role of resilience in every successful entrepreneur

37:27 Managing loans with phone notes—and why that couldn’t last

38:42 Demoing existing lending software and deciding to build his own

40:07 Launching Lender as an MVP—and letting customers shape it

41:28 Our experience transitioning 60+ active loans into Lender

44:26 How customer feedback directly drives product development

45:15 Growth strategy, conferences, and expanding the team

49:13 Using AI to automate document review and insurance tracking

50:14 The future of AI-powered underwriting

52:23 How Lender replaces full-time employees and reduces risk

53:28 Building trust with investors through systems and safeguards

Quotables

“You can’t fail if you don’t quit.”

“If I’m going to live in a system all day, it better be built well—and built for real operators.”

“Most people underestimate how important underwriting experience is in lending.”

“Capital always finds a home if you keep your marketing turned on.”

“Every business starts messy. The ones that survive are the ones that build systems.”

Links

Lender Software

https://lender.com

608B Capital

https://608bcapital.com