Last year at the Mid-America Trucking Show, Tapan Chaudhari introduced Hey Bubba, a voice AI dispatcher and assistant made for owner-operators and small fleets. Bubba looked like it had the potential to seriously shake things up.
Bubba promised to handle back office work, including invoicing, managing rate cons, even filing for detention if the terms of a load allowed for it.
More directly as a dispatcher, Bubba also stood ready to call brokers on any given load and negotiate a price on your behalf.
Brokers use AI, perhaps to onboard carriers, all the time, reasoned Chaudhari. Why not fight fire with fire and arm owner-ops with their own AI?
Pesky track-and-trace needs -- Bubba promises to handle those, too. "We can handle all communications from the customer through email or phone calls, look in the system to get a location from the ELD, and if the location is older than 15 minutes Bubba will make a call to the driver," said Chaudhari.
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Overall, Bubba promised a year ago to take most of the pain out of booking loads and hauling for brokers.
Why hasn't it taken over the trucking world yet?
The answer certainly isn't the price -- Hey Bubba remains free for all owner-ops to try out for three months, and Chaudhari doesn't even plan to start charging anyone until next quarter.

The easy answer is that last year Bubba only offered a single load option, or allowing owner-ops to get the AI agent to call on a single load.
"At the end of the day, that's just one call you could have made yourself," Chaudhari said.
Hey Bubba CEO Tapan Chaudhari, on the East Hall Pro Talks Stage at MATS in March.
Now, Bubba offers what it's calling Autopilot, which comes much closer to emulating a full-on dispatcher.
Autopilot "can make parallel calls and emails to cross-negotiate and book the best freight," said Chaudhari.
Basically, you tell Bubba what lane you need, set a price floor, and let the AI make five or ten or even more phone calls at the same time to different brokers to negotiate loads. The agent will scroll through Truckstop, DAT, and 123LoadBoard, with whom it has partnerships, likewise big brokers like Uber Freight and Arrive Logistics.
It can even comb through offers in your email.
But Chaudhari, still hopeful his bootstrapped AI agent and 18-person company will eventually take over trucking, gave some stark examples of why slow growth is better than a blitz.
"You know Sam Express?" Chaudhari asked.
For those who don't, Sam Express is part of a now-infamous ring of "chameleon carriers" under investigation after a horrific, deadly crash caused by an "illegal" immigrant and non-domiciled driver.
Chaudhari said Sam Express "came to us and wanted to use our product.
"We had a call with them and they wanted to book 200 loads every week," he said. Perfect, Chaudhari thought, "looks like a good customer."
Yet when Chaudhari looked closer into the carrier, he saw only 20 trucks listed on its federal Safer profile. "Where are the other trucks?" he asked, only to hear back that Sam Express wanted to "just book it to one MC, and then they had these other carriers we give it out to."
If that sounds like a double broker looking to use AI to scale up operations, that's because it probably is.
Chaudhari and Bubba didn't work with Sam Express. A few weeks later, when one of their drivers got into a now-infamous crash, he realized he's dodged a bullet.
"We are very cautious in enabling this Autopilot," he said. "We take calls with owner-ops to see who is interested and who is real, because we don’t want to get caught into a space where people are saying now that our AI is being used by scammers."
Imagine double brokers instantly, immediately not just undercutting you on every load posted to DAT, Truckstop, and other big load boards, but using AI agents to lock down the loads within seconds. That's the kind of AI-enabled horror Chaudhari hopes to avoid, not just for his own company's reputation, but for the good of the industry.
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AI's trucking potential, despite automation obstacles
Trucking still presents major obstacles for full automation. After Chaudhari's presentation at MATS, an owner-op approached him with all the ins and outs of flatbed hauling.
What if the load weighs 20,000 pounds more than the broker claimed? What if the broker incorrectly describes the freight, or what if it requires much more chaining and tarping than previously thought?
"We don’t touch anything oversized," said Chaudhari, to start. But with "a regular flatbed carrier, Bubba can support that. AI is very much capable of handling [flatbed loads]" and can detect when a commodity might need special attention.
"How many tarps? How many chains? Do they have ramp or not?" -- Bubba is trained to ask all these questions while negotiating.
"If the broker is lying, all of these calls are now recorded," he added. "If something comes up later, Bubba can say, 'Hey, this is what you mentioned before.'"
The service works exclusively for carriers, and does not take money from brokers or shippers: Chaudhari believes it would be a conflict of interest, and that the AI agent must be the carrier's representative solely.
Additionally, Chaudhari has not raised money to build Bubba, instead self-funding to the tune of some $3 million already. Almost all of that money has gone towards paying programers and dishing out free AI services to owner-ops and small fleets, none of whom have paid for the service yet.
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Chaudhari still thinks Bubba will play a major role representing the asset side in the spot market. He's comfortable with the pace and progress so far.
When AI does eat trucking, he thinks it will be brokers, not owner-operators, left out in the cold. After all, the brokerage world has already got plenty of reasons to fear automation, something always easier to bring to a desk job than real-world trucking.





















