Freight buying has a dirty secret: most bids do a great job of finding the lowest number and a terrible job of finding the best outcome. When shippers reward price without measuring service, good carriers get punished, bad actors slip through, and procurement teams spend weeks in spreadsheets trying to guess what suppliers actually want.

We sit down with Alan Holland from Keelvar to break down a better approach using sourcing optimization, mechanism design, and AI agents. Alan explains how incentive compatible auctions can pull truthful preferences to the surface, why package bids and conditional discounts create space for small fleets to win the lanes they can run best, and how the Google Ads auction is a surprisingly useful model for modern freight procurement. From there we get practical: connecting transportation management system performance data to the sourcing event, weighting on-time performance with price, and designing feedback loops that reward reliable execution instead of “cheap and shaky” promises.

We also zoom out to the bigger AI shift. Massive compute, LLMs, and code generation tools like Claude Code are changing how software gets built, which means logistics technology will evolve faster than most teams are ready for. We talk about risk, uncertainty, penalty cliffs, rebate targets, and the long-term “holy grail” of multi-shipper combinatorial exchanges that could unlock network-level efficiency.

If you care about freight procurement strategy, logistics automation, AI in supply chain, or the future of brokers and carriers, hit play. Subscribe, share this with a friend in logistics, and leave a review with your biggest question about where AI agents help most.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/

Freight is a physical business, but the decisions that make or break a carrier feel more digital every month. I sit down with Chris Ceausu, CEO of White Arrow, to unpack what it really takes to run a complex transportation network across intermodal reefer containers, cross-dock facilities, volume LTL consolidation, and a supporting freight brokerage. If you’ve ever wondered why two carriers can run “the same lane” and get totally different results, this conversation makes it painfully clear: cost allocation, process design, and execution are the whole game.

We get into the hard stuff operators don’t love to say out loud: how margin compression forces brutal pricing choices, why asset utilization can matter more than almost any overhead cut, and why trying to “predict the market” often feels like trusting a Ouija board. Chris shares how he evaluates signals like the CASS Freight Index and utilization data, why he’s working to reduce exposure to the most cyclical truckload segments, and how a network with multiple touchpoints creates both service advantages and operational risk.

Then we get into AI in logistics, not as a buzzword, but as a tool that can ingest real operational data, summarize call drivers, and speed up building internal workflows. Chris explains his “own the core, plug in the rest” tech strategy, why security is a serious concern when you connect AI to sensitive systems, and why execution is the only thing that ultimately matters. If you lead in trucking, brokerage, supply chain, or transportation procurement, you’ll leave with practical ideas on tech, pricing, and building teams that can adapt fast.

Subscribe for more operator-first conversations, share this with a friend in freight, and leave a review if it helps.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/

A 10‑day wait for a refrigerator became the spark for a smarter last mile. We sit down with OneRail CEO Bill Catania to unpack how a racing mindset—frugality, failure tolerance, and relentless iteration—translated into a platform that helps retailers move from static delivery workflows to real‑time orchestration at scale. Bill shares the throughline across three startups: aggregate fragmented supply, connect it cleanly to demand, and let data science make the hard choices in milliseconds.

You’ll hear how RaceFan aggregated 650 local tracks to unlock national sponsorships, why MDOT’s 200‑millisecond cloud coupon switch won over skeptical retailers (and how Bill timed the sale), and the moment OneRail shifted from gig moving to an enterprise platform. We break down OneRail’s three‑layer model—software first, an aggregated carrier network across sedans to flatbeds, and a human exception team—and how the company takes on risk under its authority to deliver accountability most intermediaries avoid.

AI is not a bolt‑on here. Bill explains how courier “credit scores,” market‑level performance, and dynamic assignment replaced manual dispatch, enabling one person to triage roughly 4,000 orders instead of 80. We explore exceptions in furniture and cold chain, SKU‑level loss analysis, and how pushing intelligence upstream into order management can reshape cost to serve before a truck even moves. Along the way, Bill shares the “yes if” leadership mantra that keeps doors open while aligning risk and reward—fuel for winning enterprise trust and recognition like Lowe’s Innovation Partner of the Year.

If you care about last mile logistics, enterprise retail, or building resilient platforms, this conversation is a blueprint: aggregate wisely, decide precisely, own outcomes, and scale through partnerships. Subscribe, share with a teammate who obsesses over SLAs, and leave a review with your biggest “yes if” moment—we’ll feature the best on a future show.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/