In this episode, Andrew welcomes Charley Dehoney, CEO and cofounder of Upwell. Charley has worked at brokerages like Worldwide Express. He bootstrapped his own brokerage, Dehoney Transportation Management. He bought and sold the 50-year-old Mannings Truck Brokerage. He’s worked for a digital freight startup, a supply chain accelerator, and a container shipping company. And that’s not even all of it. Across every chapter, one thread stands out: Charley’s intimate understanding of freight payments and the cash flow challenges that logistics companies face.

So when Charley reflects on his career, it’s clear why it’s led him to where he is today. As he puts it, “The sum of all of those experiences have positioned me uniquely to do exactly what I’m doing at Upwell.” 

In this conversation, Andrew and Charley also get into:

• The trust problem in freight and why we need more API: Assume Positive Intent
• Trends across the rise of managed transportation, broker consolidation, and the old guard versus the new guard of brokerage ownership. 
• How Upwell is tackling the freight payments problem — and the cash flow lessons Charley learned the hard way (including selling his Mercedes in front of his own brokerage).
• A candid take on VCs in freight: why they’ve earned a bad reputation, when they make sense, and how to spot the good ones.
• Tactical advice on fundraising — how much to raise, how long it should last, and what investors really expect in return. 
• Why starting a business in a down market might be the smartest move you can make. As Charley says, “You never want to waste a good crisis.”