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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.

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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/