Episode 85: Tyson Lawrence on Losing It All & Building Back Smarter

What happens when your first brokerage hits $10M… and then collapses?

In this raw and real conversation, Tyson Lawrence, founder of Diablo Freight Ventures, walks us through his 20+ year freight journey — from CH Robinson hustle to drayage grit in East Oakland, and through the gut-wrenching experience of losing his first company and going through personal bankruptcy after a fallout with his largest customer.

But instead of quitting, Tyson doubled down — building a second brokerage, this time with a smarter playbook: focused LTL entry, lean processes, and customer fit over customer size. That business scaled to $25M and was ultimately acquired.

Today, he runs Diablo Freight Ventures, a freight investment and coaching platform, and he’s helping the next wave of founders avoid the mistakes he had to learn the hard way.

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