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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.
______________________________________________
📍 Thanks to our incredible sponsors:
⚫️ Rose Rocket and TMS.ai are transforming the freight industry with seamless transportation management solutions. Improve your operations, streamline communication, and gain real-time visibility—all in one powerful platform. Try RoseRocket and TMS.ai today!
⚫️ Salesdash CRM is built specifically for freight brokers & 3PLs. Organize your sales outreach, notes, follow-ups, and lane profiles for your shippers and carriers. All for an affordable price. Try Salesdash free for 14 days with no credit card required.
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By Thomas WerdineWhat 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.
______________________________________________
📍 Thanks to our incredible sponsors:
⚫️ Rose Rocket and TMS.ai are transforming the freight industry with seamless transportation management solutions. Improve your operations, streamline communication, and gain real-time visibility—all in one powerful platform. Try RoseRocket and TMS.ai today!
⚫️ Salesdash CRM is built specifically for freight brokers & 3PLs. Organize your sales outreach, notes, follow-ups, and lane profiles for your shippers and carriers. All for an affordable price. Try Salesdash free for 14 days with no credit card required.