Trucking has plenty of trailers. They're just in the wrong place.

Todd Waldron, Chief Commercial Officer at REPOWR, joins host Kevin Carpenter to break down the trailer sharing marketplace that has moved more than 60,000 trailers across 10,000+ carriers and 275 suppliers. A dry van now runs about $50,000 and a reefer up to $90,000, yet the average trailer spends 30 to 40 percent of its life empty or idle. REPOWR lets fleets relocate trailers by renting them out instead of paying a driver to go out of route, and gives carriers and shippers access to equipment right where they need it.

Kevin asks the expedite question: how fast can you actually reposition a trailer? Todd walks through short run pricing, the new loadaway product and a realistic five to seven day window. They also get into trailer tracking, fraud and the guardrails owners set over who hauls their equipment, when owning still beats renting, and how REPOWR's trailer optimization platform balances trailer pools automatically. Then Todd takes on the On Air Gauntlet, and pickles do not fare well.

Todd has 19 years in transportation, including CH Robinson, JB Hunt (where he helped build JB Hunt 360), CEO of Q Carriers, and VP of Carrier Experience at Truckstop.

Learn more about REPOWR: https://www.repowr.com
Need something moved today? https://www.airfreight.com

On Air with AirFreight.com explores every corner of the transportation world with the people who keep it moving.

The Supreme Court removed the federal preemption defense freight brokers relied on for decades. Brian Dreher, Vice President of Transportation at Brown & Brown, joins Kevin Carpenter to explain what actually changed and what it means for anyone who hires a carrier.

They get into the practical stuff: why "any auto" policies have mostly given way to scheduled auto and scheduled driver policies, why verifying that the specific van and driver on your load appear on the carrier's policy is now the highest-value check a broker can run, and how to get that written onto the certificate in the first place.

Brian also explains why the bigger near-term cost is not the nuclear verdict everyone fears. It is the price of defending the suits that are now worth filing. Old cases are being pulled back into play. Reasonable care will mean something different in every state. And all of it points the same direction on premiums, which points the same direction on freight rates.

Chapters
0:00 The subject nobody wants to talk about
1:46 Why carriers cut corners on insurance
3:56 The red flag to check on every certificate
5:57 What "scheduled" actually means
7:03 Reading the COI and asking for VIN numbers
8:15 The Supreme Court ruling, explained
9:17 What counts as a nuclear verdict
11:20 Reasonable care and who carries the burden
13:15 How deep does carrier vetting have to go
14:42 Put it in writing, and the shipper's share
17:19 Old suits coming back, and the cost of defense
20:16 Why freight rates are going up
22:59 The On Air Gauntlet

A note on the case: it comes up in conversation as "Caribe versus C.H. Robinson." The full name is Montgomery v. Caribe Transport II, LLC, decided May 14, 2026 in a unanimous 9-0 opinion written by Justice Barrett. The Court held that the FAAAA does not preempt state negligent-hiring claims against freight brokers, because those claims fall within the statute's safety exception.

Guest: Brian Dreher, Vice President of Transportation, Brown & Brown

On Air with AirFreight.com is hosted by Kevin Carpenter, who has spent nearly 20 years in expedited freight operations. New episodes cover the people, decisions, and pressure behind time-critical shipping.

Listen wherever you get podcasts:
Apple Podcasts: https://podcasts.apple.com/us/podcast/on-air-with-airfreight-com/id1896897939
Spotify: https://open.spotify.com/show/033v3HrCwuSWhoy0rLv3Qx

AirFreight.com moves time-critical freight by air and ground across North America. https://www.airfreight.com

#expeditedfreight #freightbroker #logistics #truckinginsurance #supplychain

Todd Anderson came to AirFreight.com after nearly ten years at one of the largest expeditors in the country, first leading an operations team on the 3PL side, then in corporate project management. He and Kevin work through the mode hierarchy, from air charter down to ground expedite, and why an NFO handled front and back is a different product from handing a shipment to an airline and hoping. The part worth the listen is his standard for judging a carrier: anyone can run a clean shipment, so he watches what happens when one goes wrong. He tells it through a carrier who dropped freight at the wrong address on a first shipment with a new customer. The communication was honest and immediate, they tracked the freight down, and that customer is now his biggest.

00:00 Intro
00:52 Ten years at one of the largest expeditors in the country
01:41 What makes freight "expedite": speed and care
02:51 Why a dedicated truck removes the failure points
03:52 The mode hierarchy, starting with air charter
05:45 NFO, hand carry, and who actually touches your freight
09:43 Why "hotshot" means something different in Texas
10:35 What a top-tier carrier network really means
10:51 How Todd judges a carrier when something goes wrong
12:10 The wrong address delivery that created his biggest customer
13:33 The vetting process, and going deeper than the surface
16:17 Coast to coast coverage on one-off, time-critical freight
19:02 Two customers: the one paying us and the one we pay
20:17 "A diamond in the rough"
20:53 The On Air Gauntlet