The GlobalTranz Mafia and Beyond with Charley Dehoney

In this week’s episode of The FreightCaviar Podcast, we sit down with Charley Dehoney, CEO & Co-Founder of Upwell. Charley shares his journey from freight brokerage to freight technology, discussing his early experiences at Worldwide Express and GlobalTranz and the influence of the "GlobalTranz Mafia" on his career. He explains how he acquired a 50-year-old brokerage, doubled its revenue, and sold it to FitzMark in just 19 months. Charley also addresses the challenges faced by small brokerages, the impact of private equity, and why he believes industry consolidation is on the horizon.

A Dream of Entrepreneurship 

Earlier this year, he celebrated 21 years in the industry. From an early age, Charley dreamed of being an entrepreneur. An alumnus of San Jose State University, he began his career in tech, which back then was a completely different space than we know today. He spoke of his very first role at Worldwide Express, what it taught him, and the moment he realized logistics was the place for him.

“Nothing mattered to me more than creating a path from the impoverished background and upbringing that I had, and to create a path towards wealth. And I knew that logistics could be that for me. So as I got out of WorldWide Express, I knew how to sell, and I knew I could grow.”

Climbing The Logistics Ladder

From there, Charley spent six years working his way up from sales to leadership positions. Along the way, he bootstrapped a couple of companies and even owned a transportation company. He reflects back on that time and what he would do differently today.

“Its really hard to grow in transportation unless you have a backstop. And thinking about that business now, knowing what I know now, I would have raised a little bit of equity, taken on one partner, maybe got a debt line, and grown that debt facility over time and scaled the business to a billion dollars.”

Learning to Build and Scale

In 2013, he joined Cargomatic, later Shiphawk, and more recently, co-founded Airspace Technologies in 2018. It was there, under this venture-backed ecosystem, that he learned how to build technology and raise venture money. 

Secret to Selling a Business

In 2019, he took over as CEO of Manning's Truck Brokerage and successfully sold the company to FitzMark, Inc., in just under nineteen months. When asked about selling a business successfully, this is what he has to say:

“If you want to sell to a big guy, number one, have your product ready. It doesn't have to be perfect, but it's got to be ready. You have to really have your material and collateral buttoned up and crisp and sharp, otherwise it's just not going to pass muster. So it really comes down to communication and it comes down to stamina. And so if you can have your messaging tight and you can get the right people around the table and you just don't give up, you'll get deals.”

Building Upwell

It was there that he realized he was a builder. All the years he spent working in sales prepared him for his role as CEO and Co-Founder at Upwell, a payment company helping logistics companies get paid on time. It sits between the transportation management software, the accounting software, and your accounting email. 

“What we're doing is we're building the world's largest library and catalog of shipper invoice requirements. Upwell is built on the most sophisticated engine out there. The key is we're not just focused on telling you what's on the document and then letting you do something with it. We want to get that document directly where it goes. And more importantly, we want to tell you when it's the wrong document.”

Don’t Stop Believing

What inspires Charley to keep going? Seeing the product out in the wild, hearing people’s feedback and their ideas.

 “Every day we're having customer calls with existing customers, checking in on their progress, and they're coming to us with new ideas.”

Predictions for the Industry

We also talked about his future predictions for the industry and discussed what he described as what once was the Golden Age of Brokerage.

“I just think it's going to be hard. I think there was a golden age of brokerage. There's a lot of companies that came around and they've really crushed it. From this crop of brokers that are starting up now, I don't think we're going to see that.”

Challenges for Smaller Brokerages

Finally, he also shared his thoughts on the future of smaller brokerages and the consolidation of the industry. In his opinion, there will be two options.

“These little guys are either going to have to figure out how to get big, or they're going to get creative and merge up so that they can get acquired. The big companies are just going to continue to figure out how to book freight for less and how to control drivers and keep them in their captive audience. And it's going to get harder and harder for the small guy. I think we're going to continue to see the division where the big continue to get bigger and they consolidate the middle guys, and the small just kind of stay.”

So what exactly should you do if you’re looking to sell? Charley has the answer, but also a warning for those looking to get acquired in the future.

“These big brokerages, they're not a golden ticket. It's not a money-printing machine, so you have to do everything right.”

Charley’s story is one of resilience, adaptability, and commitment to growth. It’s quite clear that even greater success lies ahead for Charley and Upwell. 

Listen to the entire interview on Apple Podcasts, or Spotify, or watch it on our YouTube channel.