🎣 Dispatching Freight's Future

On today's episode, we sit down with Dan Kao, Co-Founder & CEO at TruckSmarter, a free load board and all-in-one platform that helps truck drivers, owner-operators, carriers, and dispatchers find higher-paying loads and much more.

He shares insights on launching DoorDash in Canada, predicts where the industry is headed, and explains how the company is helping businesses operate more efficiently.

Don’t forget to check out this week’s featured carrier, powered by TruckSmarter!

How AI Can Give Drivers Their Time Back

Dan’s story is one of grit, resilience, and unconventional thinking. Born to Taiwanese parents who had dreamed of starting their own business but were unable to, he was inspired to forge his own path and create something of his own.

After graduating from NYU’s Stern School of Business, Dan ventured into the technology world. In 2014, he moved to San Francisco to join Square, a business technology platform.

"I was drawn to Square because their ethos was to make it ridiculously easy for the everyday entrepreneurs to run their business. I saw how hard it was to get started first-hand and wanted to make it as easy as possible for everybody else."

He later joined DoorDash, soon leading their first international launch in Canada at a time when the company had fewer than fifty employees and operated in only a handful of cities. It’s hard to imagine now, but at the time, DoorDash was far from being seen as the food delivery giant it is today.

What has since become a household name had a humble and challenging beginning.

“You had a driver coming in with a big, red bag with DoorDash on the front. The restaurant is like, ‘Who the hell are you?’. Then more often than not, they’d call me or whoever else that’s running the market and say, ‘We don’t want to be associated with you guys,’ but then we’d go to that restaurant, show them the sales, and ask if it was worth a conversation. That was the growth hack.”

They quickly realized this was the only way to build restaurant density; otherwise, it would have taken years just to get a foot in the door with the right decision-makers.

For three years, it was nonstop hard work—sleeping in the office, showering at the gym. ‘You can have as much capital and hype as you want,’ Dan says, ‘but if you don’t have people who have the grit and determination to go the extra mile, you won’t get anywhere.’

That relentless drive carried over to his time at Uber Freight, where Dan began seeing opportunities to apply his experience.

In 2019, while running the shipper platform at Uber Freight and building technology tools for small- to medium-sized shippers, conversations with drivers revealed how underutilized they were. Dan recognized that an entirely new opportunity was waiting to be unlocked– and the idea for TruckSmarter was born.

Three years later, he co-founded the company.

“When we first started, we were like, ‘Nobody wants to be opening up 30–40 apps to go and try to piece the market together. By the time you find a load, it’s going to be unavailable. So what we did was we effectively aggregated all that information to a single place. I think we ruffled a few feathers as well, but we had a lot of great conversations with brokers and many of them are some of our best partners.”

On Monday, TruckSmarter made an exciting announcement alongside their $16 million raise. They introduced their latest product, Dispatch, an AI-powered assistant that helps carriers book loads faster. Since its beta launch, carriers have reportedly already saved 1000s of hours a week verifying load details and receiving successful load matches.

We asked Dan how he thinks communication with AI, truckers, and brokers will evolve over the next decade.

He notes truckers are already operating at full capacity, so adding an AI tool only brings more of it to the table. This allows them to focus on other priorities, like running their business more efficiently, because they no longer have to spend two to three hours a day hunting down a load.

“You see this with any technology, people may be comfortable with the way they’re running their businesses, and that’s fine, but then you see those that do adopt it, it’s like adding a jetpack onto your business. You can do things far more interesting than call on loads.”

Dan also weighed in on the current climate in the VC world and what investors are focusing on.

“I think the most attractive thing about it is the opportunity size, and that’s what VCs care about. I think there’s enough scar tissue now, at least within freight, that the tech investors are looking at what’s really durable. What are you doing that’s actually going to stick around through the next cycle?” 

When asked whether excitement among Silicon Valley VCs has remained the same or faded, Dan says:

“There’s a lot more exuberance now, and it’s warranted. We have new AI technology that can fundamentally change the landscape of every industry. For the builders, you have to reconsider everything frequently with new tech developments.”

He also gave us a glimpse into his daily life. Living in San Francisco, Dan admits it’s difficult to disconnect from work. 'You really have to love what you do,' he says. Even during dinners with friends, technology inevitably comes up in conversation.

“You have to pick between work and life. At least at this time in my life, I’m prioritizing work. I get so much energy just doing what we’re doing.”

Dan’s story shows that determination and hard work pay off, while highlighting the exciting developments we can expect within the next decade in freight.

In this episode, we cover:

• Are We Creating a Race to the Bottom?: Dan confronts the criticism that making it easier to start a trucking company is flooding the market and driving down rates for everyone.
• The Coming Load Board Wars: With a hard stance that "load boards should be free," Dan is challenging a fundamental business model in freight.
• Your Broker Is About to Be Obsolete: AI adoption by carriers will force brokers to automate or die. Dan explains why the holdouts don't have much time left.

Here's what Dan had to say on building your own product:

“DoorDash dispelled the notion of having to build this perfectly done thing to create something amazing. You should just go and start it."

Listen to the episode on Apple Podcasts or Spotify. Watch the interview on YouTube.

Brought To You By Trinity Logistics

At Trinity, our Pricing Team helps you stay competitive. From assisting with customer RFPs to offering insight on market conditions, project pricing, and transactional quotes, we give Freight Agents the tools to price smarter and win more freight. Our multimodal expertise ensures you’re ready for ANY opportunity. 

Carrier of the Week: MAY Trucking LLC

• MC: 1451329
• Location: Covina, CA
• Years in Business:  5
• Equipment: Transports all types of freight
• Lanes: Generally runs CO, AZ, NM, TX, ID, WY, UT, NV, MT, but will go anywhere except North-East.
  
• Behind the company: MAY Trucking was founded in 2020 at the height of the pandemic by Mark Yaxley, a native of Oxford, England. Frustrated by the frequent shutdowns affecting his business at the time, and seeing a strong demand in the industry, he partnered with others briefly until he could get his own MC. Since then, he's been successfully running the company on his own. Based in California, it specializes in transporting a wide range of freight and prides itself on putting quality over quantity.

One thing they wish more brokers understood:

"The broker should bear in mind that the load we are on is the sole income stream during that time period, and offer a rate that is supportive to maintaining a reliable and profitable business. We will go above and beyond to ensure a safe and timely delivery, and show great loyalty to their business."

Want to be featured? Fill out this quick form to be our next Carrier of the Week.

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• Built for high-reliability, high-volume workflows
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🎣THE FREIGHT CAVIAR CORNER

• Manifest 2026: We're proud to be an Official Partner of Manifest: The Future of Supply Chain & Logistics conference, the premier event shaping what's next in freight and logistics. Save an additional $200 when you register now before prices increase September 12.
• Freightjobs.co: Join HaulPay’s Customer Success team as a Customer Experience Specialist. Help brokers and carriers onboard, retain, and grow. Apply now.
• Freight Broker Group Chat: Lost a load to a ghost MC? Just discovered a 15-layer carrier spoof ring? Come swap war stories, drop memes, and ask the stuff no one wants to post on LinkedIn. Join us on forum.freightcaviar.com

FREIGHT HUMOR