The Stack Is Stacking Itself. I'm Walking Past It.

By Millisa Nwokolo, Founder of La Crown Inc. — May 10, 2026

The 29th-largest freight broker in the country shut down in January. AGX Freight died days later. Helix Logistics imploded the same week. Meanwhile, three SaaS giants spent over $700 million bolting themselves together — and my top customer runs a 150-year-old business off email and Excel.

A few weeks ago I sat down and started counting how many freight brokerages, freight tech platforms, and trucking companies with affiliate brokerage authority have either filed Chapter 11 or simply shut their doors in the last eighteen months. I lost count somewhere past twenty. The list now includes the 29th-largest freight broker in the country — R&R Family of Companies, an $850-million-revenue Pittsburgh operation that just stopped operating in January and left hundreds of carriers unpaid.

In that exact same window, three of the biggest names in freight tech have spent the better part of seven hundred million dollars buying each other up. DAT bought the Convoy Platform from Flexport for around $250 million. DAT also bought Outgo for payments and Trucker Tools for visibility. Triumph Financial bought Isometric Technologies and then Greenscreens.ai for $160 million. McLeod stitched its TMS to Truckstop's payment platform and then bolted on Aurora's autonomous trucks. RXO bought Coyote for $1.025 billion. Schneider National bought Cowan Systems for $390 million.

Here is what nobody in freight tech is saying out loud, and what every operator I know is starting to feel in their gut: the stack is stacking itself. The same SaaS vendors who have been selling us subscriptions for the last fifteen years are bolting themselves together as fast as they can. The bigger the stack gets, the more I'm convinced the game has actually changed and most operators don't see it yet.

I'm not trying to be one of them. I'm walking past the whole thing.

The Body Count (Eighteen Months In)

Pull up a chair. This is what the freight market actually looks like right now. These are real companies, real Chapter 11 filings, and in some cases real shutdowns where drivers and dispatchers walked into work on a Monday morning and were sent home by lunch.

And then the smaller waves. Liberty Carriers, NAS Logistics, Golden Spirit Freight, NV Freight, Star One Transport, and PSS Trucking all filed in April 2026. Best Choice Trucking, C&C Freight Network, Best Logistics, AZA Transportation, and Mister M&K Trucking filed across April through October 2025. Newkirk Logistics, Mast Trucking, and Bee & G Enterprises filed in February 2026. Standard Freight Logistics filed February 23, 2026. Bulmaks Inc. filed January 5, 2026. VIB Trans filed October 2025.

That isn't a complete list. That's just the names a freight broker who keeps an eye on FreightWaves and TheStreet can rattle off. Bankruptcy filings across the freight transportation and logistics sector continued to mount through March of this year, with companies filing across trucking, brokerage, last-mile delivery, and marine transportation. Industry analysts estimate 5,000 to 8,000 trucking companies effectively exited the market in 2025 alone. The most significant capacity shakeout since deregulation in 1980.

Meanwhile, the Big Guys Are Bolting Themselves Together

Now compare that body count to the deal sheet on the SaaS and platform side over the same eighteen months. This is where I find it odd. Tools are making the stack bigger. The two big load boards — DAT and Truckstop — are buying the same kinds of layers as fast as they can: payments, factoring, visibility, freight matching, automation. Watch what's actually happening:

DAT — The most aggressive buyer

Truckstop — Building the same stack

Read those Truckstop and DAT lists side by side and tell me what you see. Both load boards are buying the same stack. Payments. Factoring. Back-office automation. Visibility. They aren't differentiating. They're racing each other to be the one platform that owns every piece of the broker's day.

Triumph Financial — The third pole

McLeod — Stitching the TMS to everything

The asset brokers — Consolidating up

And one more for context: DAT's parent company, Roper Technologies (a $60 billion market cap holding company), spent over $450 million on freight tech acquisitions in seven months alone. FreightWaves analysis.

The math is brutal. The same period when twenty-plus named freight companies are dying, the SaaS and platform layer is consolidating into three or four mega-stacks. FreightWaves CEO Craig Fuller called it "load-matching wars" — three rival groups (DAT, Truckstop, and a Highway+Triumph combination) racing to be the dominant freight exchange platform.

Three Wars That Aren't Yours to Fight

I find it odd that everyone in this industry is acting like the answer to AI is to make the stack bigger. TMS plus load board plus payments plus visibility plus carrier vetting plus autonomous capacity plus factoring — all in one platform, please don't unsubscribe, here's a discount if you sign for three years.

That isn't AI. That's bundling. It's the same playbook the cable companies ran in the 90s.

There are three wars happening right now and none of them was started by an operator like you or me:

Watch closely. These wars are about who gets to charge you the recurring fee. They are not about whether you should be paying it in the first place.

As a freight broker I literally had twelve to fifteen websites open every day to do my job. TMS. DAT. Truckstop. Highway. Trucker Tools. McLeod. Customer portal. Carrier portal. Compliance portal. COI inbox. Email. Slack. Quoting tool. Mileage calculator. Accounting. The shared drive where the rate confirmations live. Every tab is a subscription. And now those subscriptions are merging with each other so when one of them raises my price, I can't unbundle the piece I actually use.

My 150-Year-Old Customer Doesn't Need AI

Here's the part the SaaS folks don't want me telling you out loud.

My top customer right now runs their entire business off the cloud, email, and Excel spreadsheets. They have been around for over 150 years. They are successful. They do not need AI, nor will they probably ever need AI in the way the vendors are selling it.

They send me orders by email. I quote them by email. They pay me on terms. The whole relationship runs on the basics — trust, response time, and clean execution. If I tried to get them onto a "platform" they would politely decline and then move their freight to whoever made it easiest by email. The platform isn't the product. The trust is.

Another one of my top customers has fourteen divisions across the country. Top in their field. They use Gmail. They have no social media presence whatsoever. Zero. And they are crushing it.

Both of those operators built their businesses long before the SaaS stack existed. The thing that made them successful is the same thing that's keeping them successful — relationships, judgment, and a stubborn refusal to outsource the parts of their business that actually matter. They don't need a $200-a-month platform to know who I am, what I charge, and whether I move their freight clean. They need a phone, an email account, and a person on the other end who knows what they are doing.

AI Isn't Making the Stack Bigger. It's Making It Optional.

This is where I disagree with the entire freight tech industry.

The vendors are reading AI as a reason to bundle more — bigger platforms, deeper integrations, more lock-in, longer contracts. They think AI is the next gold rush and the way to win it is to be the one platform you can't live without.

I think they are reading the signal exactly backwards.

What AI actually does is give the small operator the ability to do what only the big stack used to be able to do. Quoting. Tracking. Carrier vetting. Voice agents. Pricing models. Fraud detection. COI follow-up. Document handling. All of it. Built on your own data. Held in your own systems. Without paying anybody else.

The big guys are trying to build the moat higher. AI is filling in the moat. The reason load-matching wars even exist is that the platforms know — somewhere deep down — that the operator with their own AI doesn't need their load matching anymore. The operator with their own AI doesn't need their TMS anymore. The operator with their own AI doesn't need their visibility platform, their factoring platform, or their payments platform. The operator just needs the data and the systems to act on it.

Look at the bankruptcy list again. Most of those companies didn't fail because they couldn't move freight. They failed because their margin was too thin to cover the SaaS stack on top of the operations stack. Every one of those subscriptions was supposed to make them more efficient. Add them all up and they ate the margin instead.

I Am No Longer Reliant on Anyone. That's the Part That Scares People.

A few months ago I made a quiet decision. Anything I was paying for as software, I was going to build myself. Anything that lived inside a vendor's database, I was going to move into systems I owned. Anything that required a recurring subscription, I was going to question whether the recurring value justified the recurring fee.

Most of the time, the answer was no.

I built my own transcription tool. I built my own quoting skill on top of my own customer data. I built voice agents — five of them now, with names like Anna and Brad and James and Kara and Mike — that handle compliance, tracking, document follow-up, COI requests, and inbound carrier sales. I linked Claude to my TMS and started asking it questions about my own book of business. Each time I add a piece of context — a customer-specific rule, a lane-specific quirk — it remembers. None of those tools live on someone else's roadmap.

What that means in practice is I am no longer reliant on anyone to do business. Not on a load board to find me a carrier. Not on a TMS vendor to roll out the feature I needed last quarter. Not on a payments platform to give me terms. Not on an enterprise tool to give me visibility into my own data that I should have had all along.

That makes a lot of people nervous. I get it. If you have been selling software to operators for fifteen years and the operators figure out they don't need you anymore, that is a big problem for your investor deck. The whole freight tech industry is reading the same data I am reading and reaching a completely different conclusion. They see a market consolidating and assume the survivor takes all. I see a market that just woke up.

My 150-year-old customer is going to keep running her business off email and Excel and beat everyone she competes against because she actually knows what she is doing. The 14-division Gmail customer is going to keep dominating his field because his judgment is better than the algorithm. And the small broker who quietly builds her own systems on her own data is going to outlast every Chapter 11 that's coming this year and next.

The stack is stacking itself. The wars are happening in someone else's boardroom. The body count is mounting on the side that paid for too many subscriptions. None of it is yours to fight.

Walk past it.