Ep. #62: Charley Dehoney, CEO & Cofounder of Upwell from The Freight Pod

Ep. #62: Charley Dehoney, CEO & Cofounder of Upwell

1 hour 39 minutes Posted Apr 15, 2025 at 9:00 am.

Sponsor message and Andrew’s introduction

API: Assume Positive Intent

The turning point in a small broker’s business

The industry old guard vs. new guard

Why don’t the bigger brokers build their own AI?

An introduction to Upwell

The payments problem for brokers

Charley’s personal challenges with payments

The $15M moment that started it all

Charley’s background in freight

Buying a business with the plan of selling

Mentally preparing yourself to sell

How Upwell is different from what Charley’s done

Charley challenges the VC naysayers

Why VCs have a bad name in the industry

How to raise money and how to spot a good VC

Building a business in a down market isn't a bad thing

How do you know how much to raise?

Charley’s final thoughts on “the ultimate validation”

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Show notes

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 payme...

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