The Middle East crisis is already hitting carriers. Plus: Florida lost $3B in crops, flatbed rates posted a fifth straight weekly increase, a $5B brokerage was just acquired, and more.
Plus: autonomous trucking just raised $113M, California is fighting to keep 20,000 drivers, Arrive's 2026 truckload freight forecast, and more.
Two bills just dropped in the Senate that could reshape trucking faster than anything since deregulation. Plus: Russian hackers targeted your load board, flatbed rejection rates just hit 40%, and a robot is taking the Houston-Dallas overnight run.
If you've ever wanted to go behind-the scenes at Uber Freight, learn about the future of custom software and AI in the industry, we've got all the insights from Kevin Novak, ex-Uber Head of Data, and today Managing Partner & Founder at Rackhouse Venture Capital.
Today, we sit down with Kevin Novak, ex-Uber Head of Data, Managing Partner & Founder at Rackhouse Venture Capital, an early-stage venture capital management firm that focuses on founders and companies that sit at the intersection of AI/ML and the real world.
Kevin shares insights into his creation of surge pricing model for Uber's ride-sharing service, predictions for AI in the industry, and why he thinks the majority of software stacks are bound to fail in the future.
Be sure to check out this week’s featured carrier!
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As a native Michigander, Kevin began his career training as a physicist before moving to San Francisco in 2010 to pursue opportunities in data science.
He joined Uber in 2011 as a Data Scientist, quickly rising to Head of Data Science by 2014 and later Head of Data Science Platform. While in this role, he invented the surge pricing model for Uber's ride-sharing service, for which he holds several patents related to GPS processing and marketplace optimization.
In 2017, he joined Uber Freight, serving as the company’s Head of Data & Engineering, Pricing & Operations Tooling.
But what exactly made Uber so innovative at the time?
With the rise of smartphones came early tech trends like GPS data available directly on your phone. That, combined with the revolution of the cloud, Kevin notes, was really what unlocked the company's potential. Suddenly, the transportation network became machine-parseable, something that could be broken down, analyzed, and optimized at scale.
When applying his expertise to freight, Kevin recognized that drivers had to remain at the center of the experience. They were the ones navigating real-world complexities beyond what Google Maps could provide.
After 15 years in the machine learning space, Kevin founded Rackhouse Venture Capital in 2021, an early-stage venture capital management firm dedicated to supporting founders and firms that sit at the intersection of AI/ML and the real world.
We discussed the current AI landscape and Kevin’s perspective on its future in freight. In his view, the evolution has done more good than harm.
“The vast majority of AI adoption will result in some people’s jobs becoming outdated, but far more people will be using this as an opportunity to be challenged, to do or deliver more, or focus more on the strategically important parts of a job.”
When it comes to the vision of the fully autonomous brokerage, to some, it feels like voice agents are taking over, but not everything in freight can be fully automated. While things are massively improving, there’s a lot that a system can’t predict or take over for humans.
Kevin outlined the pieces that would need to take place in a decade or two to achieve a fully autonomous brokerage.
“One of the challenges with AI in general is that it doesn’t have a great BS detector or the ability to infer hidden information that is not present. There needs to be some sort of third-party verifiable system of record. There’s a more macroperspective that these AI’s just don’t have, and that might be the role of humans in this – this executive leadership to steer all of these groups.”
The million-dollar question: Is there room for every brokerage or trucking company to develop its own software?
Kevin thinks that as coding tools become more present, more people will be able to put their ideas into motion. But this doesn’t mean that every idea will be worth investing in.
“A lot of executives will get to experiment with this idea of ‘what if we rolled out our own software stack', and the vast majority of them will realize their ideas aren’t as good as they thought, and they’ll put that idea to rest, so there’ll be a lot less angst. The 10 or 20% that are truly exceptional will have an incredibly good outcome, and the others will move on to other things they’re great at.”
Kevin’s story reflects how innovation is often about timing and tech environment, not just ideas. It also reinforces a balanced view of AI: while full automation in freight is still decades away, it will push people toward higher-value, more strategic roles.
In this episode, you'll learn all about :
Here's what Kevin had to say on the importance of human touch in freight:
“We realized respect was important, but lived experience was also important.”
This week's episode is brought to you by WireBee, GenLogs, and Highway.
Listen to the episode on Apple Podcasts or Spotify. Watch the interview on YouTube.
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One thing they wish more brokers understood:
"Small companies like us struggle to find reliable brokers that offer dedicated lanes, it would beneficial even for them giving out more opportunities based on proven performance and not only online stats."
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The Middle East crisis is already hitting carriers. Plus: Florida lost $3B in crops, flatbed rates posted a fifth straight weekly increase, a $5B brokerage was just acquired, and more.
Plus: autonomous trucking just raised $113M, California is fighting to keep 20,000 drivers, Arrive's 2026 truckload freight forecast, and more.
Two bills just dropped in the Senate that could reshape trucking faster than anything since deregulation. Plus: Russian hackers targeted your load board, flatbed rejection rates just hit 40%, and a robot is taking the Houston-Dallas overnight run.
This week: The Dalilah Law, a trucking bankruptcy that wiped out thousands overnight, a FreightGuard civil war on Reddit, and the payroll data that's predicting Q4 capacity.
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