A penny stock wiped $4.8B off C.H. Robinson's market cap yesterday. Plus: self-driving trucks are now running 1,000 miles nonstop, STG Logistics cleared a major bankruptcy hurdle, the FMCSA revoked nine ELDs, and more.
For a long time, secure parking lived in the “nice-to-have” bucket. That framing no longer works. In today’s environment, secure parking functions as a preventative security layer.
Here’s what’s trending across freight and logistics on X, LinkedIn, Reddit, and YouTube.
What really happened with Convoy? How did Silicon Valley get freight brokerage so wrong? We got the answers from the ultimate insider: Bill Driegert, Co-Founder of Uber Freight and now EVP of Convoy Platform at DAT Freight & Analytics.
Happy Tuesday.
We've got the unfiltered inside story from one of the architects of modern freight tech. In this landmark episode, we sit down with Bill Driegert, the Co-Founder of Uber Freight, and now a key leader at DAT Freight & Analytics.
Bill reveals the shocking miscalculations that fueled the tech boom, the whirlwind 24-hour deal to acquire Convoy’s platform, and what brokers must know about the next wave of AI.
Plus, check out our carrier of the week!
Not everyone in the industry starts with dreams of being a racecar engineer, but that’s exactly what Bill Driegert envisioned when he moved from Atlanta to attend Georgia Tech in the 1990s. After enrolling in the Mechanical Engineering program there, he soon relocated to Vermont to start a race fabrication shop that he opened with a friend, building cars for privateers.
When the dot-com crash hit, Bill and his business partner lost many clients overnight, and revenue at the shop dropped. This prompted him to return to school, completing his BBA at the SMU Cox School of Business.
At the time, job opportunities were scarce, so he accepted an internship at Frito-Lay in supply chain. Bill often reflects on this as a great starting point in the industry, one that laid the foundation for his future career. Thanks to the company sponsoring him, in 2002, he was able to take part in the Master's in Logistics program at MIT.
From there on, Bill was immersed in the world of freight, first starting at Coyote Logistics in 2006, as the CIO, Director of Planning and Innovation at Amazon in 2014, and later becoming the Co-Founder and Head of Operations at Uber Freight. In May of 2023, he became the EVP, Head of Trucking at Flexport.
We also spoke with Bill about DAT’s acquisition of Flexport’s Convoy Platform in 2023 and its launch as a freight-matching service for brokers and carriers the following year in April.
“It was like buying a broken F1 car and then trying to hire engineers to put it back on the track...Everything had to be rewired."
While not everyone welcomed the transition, the reality is that the company pushed the industry forward, making it more tech-centric. With the changes they’ve implemented, they’ve effectively removed fraud-based theft from the platform, boasting over 380,000 theft-free loads and counting. The acquisition also enabled the scaling of the Convoy Platform to serve the broader market.
How exactly are they fighting fraud?
To maintain service integrity, drivers who fail to engage with the app are blacklisted. In addition, the company actively monitors patterns and behaviors that appear suspicious, strengthening the platform’s reliability and security.
We also got Bill’s take on technology in the industry. For those not as up-to-date on cutting-edge tech in San Francisco, he mentioned that while the ideas are the same as last year, what’s different is how quickly things are moving forward. Both autonomous vehicles and AI implementations continue to advance rapidly.
His stance on AI?
“It’s not like conversion is going to improve in certain channels just by switching to AI. In fact, it’ll be the inverse, because if you lower the cost, now people just flood the channel, so it’s going to become less and less effective. I think we’ve already seen that shift where people are going to engage with companies and brands and people proactively versus taking the call.”
Who wins in the big freight tech game? It’s safe to say brokers in tech adoptions are ahead of the curve.
But we can still expect relationships to be a priority, particularly on the shipper side, and different business models going back to app-centric carriers.
Bill expects brokerages to become more and more shipper-centric as the carrier side grows increasingly automated. Instead of chasing trucks for every load, automation will handle the matching. That frees carrier sales to focus on cultivating business with established, reputable mid- to large-sized carriers.
The verdict? To stay competitive, freight brokers need to focus more on customers and rely on stronger, long-term partnerships with carriers built on trust.
This episode covers a lot of ground:
Here's what Bill had to say on the current state of today's market:
“I think it's in a better space now. The smart brokers are figuring it out and piecing these things together, and staying a step ahead.”
This week's episode is brought to you by Epay Manager, Levity.ai, and CtrlChain.
Listen to the episode on Apple Podcasts or Spotify. Watch the interview on YouTube.
Levity automates high-volume email and phone tasks like quoting, load building, and track & trace, without black-box agents or risky AI experiments.
Designed for teams that need control, transparency, and results they can trust.
One thing they wish more brokers understood:
That we are reliable, eager to grow, and want dedicated freight.
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A penny stock wiped $4.8B off C.H. Robinson's market cap yesterday. Plus: self-driving trucks are now running 1,000 miles nonstop, STG Logistics cleared a major bankruptcy hurdle, the FMCSA revoked nine ELDs, and more.
Here’s what’s trending across freight and logistics on X, LinkedIn, Reddit, and YouTube.
In just three years, we have moved from an industry that relied heavily on manual phone calls and emails to one where many of us use AI to some extent to support the above.
Plus, XPO and Hub Group Q4 2025 earnings, a trucking private-equity firm files bankruptcy, Mexico long-haul truckers win union rights, and more.
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