HeyJaredThe Freight Show
The Freight Show brings stories of freight and logistics leaders who’ve shaped the industry. Through in-depth conversations, we explore their journeys, the challenges they’ve overcome, and the insights that have driven their success.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 9, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 9, 2026
Latest episodes
Tom McLeod (McLeod Software) on Building a Trucking Software Company That Lasts 41 Years (opens the original)
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Forty-one years is a long time to run one software company. Tom McLeod started McLeod Software in 1985, five years after deregulation blew open an industry that had been run like a public utility, and he's still at the helm today with 550 employees, no outside investors, and a product line that just went through a complete revamp. In the mid-80s, dozens of small software companies were all trying to build the operations platform for trucking. McLeod rose above the fray by the mid-90s, and Tom ha
Jacob Benbenek (Magna) on Why His Reps Get Paid on Losing Loads and How He's Gone 14 Years Without Fraud (opens the original)
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Every broker on the phone is pitching service. Jacob Benbenek has a harder proof point than most: Magna has never had a fraud incident in 14 years of business, and his carrier reps get paid on loads that lose money exactly as if they made a hundred dollars. Ask him how a small team stays disciplined on a hard-to-cover load at 4:30 on a Friday, and the answer starts with how people get paid, not with a compliance tool. Jacob spent ten years on big brokerage floors before he started Magna, a Chica
Steve Wineriter (American Diamond) on Going From Stuck at $45M to a $100M Run Rate (opens the original)
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Most brokerages that stall in the $40-50M range never get out. The math is unforgiving: growing means hiring, onboarding, and training faster than the volume arrives, but staffing ahead of volume burns cash you don't have yet. American Diamond Logistics sat at $44-45M for three straight years. Then, in a matter of months, its run rate jumped to nearly $100M. Steve Wineriter has been in freight since 2002, when he joined his dad's 3PL out of college. After founding American Diamond, he made a dec
Matthew Leffler (The Armchair Attorney) on Montgomery and the New Era of Broker Liability (opens the original)
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Everyone expected the brokers to win Montgomery, including the FMCSA. They lost unanimously. Matthew Leffler, The Armchair Attorney, breaks down the most consequential Supreme Court ruling in brokerage history and what brokers should do now.
Brandon Wolfe (Jordan Partners) on Why Freight Brokerage Is America's Most Underestimated Business (opens the original)
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A private equity investor's case for why freight brokerage is one of the most underestimated business models in the country. Brandon Wolfe of Jordan Partners on gross margin as an accounting artifact, 20%+ returns on capital, the pricing floor, build-vs-buy, and why AI won't disintermediate the broker.
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