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The Freight Show

Vooma
Freight Industry
Logistics
Freight Brokerage
Automation
Artificial Intelligence
Vooma
Axle Logistics
Echo Global Logistics
Freight Pricing
Logistics Industry
Mergers and Acquisitions
Transportation
Brokerage
Technology In Supply Chain
Data Analysis
Transportation Management Systems
Sales and Brokerage
Freightvana
Carrier Networks
Covid-19

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. Each episode uncovers the lessons, strategies, and wisdom of these freight leaders.

PublishesTwice monthlyEpisodes33Foundeda year ago
Number of ListenersCategories
ManagementBusinessMarketing

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Artwork for The Freight Show

Latest Episodes

Most operators who want back into freight brokerage would start a new company. Andrew Silver thinks that's the slow way to do it. Building a carrier network takes years no matter how good you are, and in a post-Montgomery world, a broker that opened ... more

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The Friday before the Fourth of July this year, nobody could find a truck. By Monday there were trucks everywhere and no loads, and spot conversion at EASE Logistics fell by more than half overnight. What Ken Adamo's pricing team did over the followi... more

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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, ... more

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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 d... more

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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 Logist... more

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Going into the Montgomery case, everyone expected the brokers to win. The FMCSA and the Department of Transportation both filed on the brokers' side. Matthew Leffler, a supply chain attorney and law professor, called it for the brokers too. The Supre... more

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Look at a freight brokerage P&L the way most investors do and you'll see a 10 to 20% gross margin, a 3 to 8% EBITDA margin, and a business at the mercy of the freight cycle. Brandon Wolfe looks at the same numbers and sees one of the most underestima... more

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For decades, brokerage has run on two assumptions: pay your reps on commission, and stay asset-light. Shannon Breen built FreightVana by breaking both. What happens when you strip commissions out of a brokerage entirely and own the trailers instead o... more

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Key Facts

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Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Andrew Silver
Co-founder of MoLo Solutions and host of The Freight Pod
The Freight Pod
Episode: Andrew Silver on Why He’s Buying a Brokerage Instead of Building One
Ken Adamo
Chief Strategy Officer at EASE Logistics; spent seven years at DAT working on forecasting and analytics products.
EASE Logistics
Episode: Ken Adamo (EASE Logistics) on Why You Can't Price Like a Coward
Tom McLeod
Founder and CEO of McLeod Software
McLeod Software
Episode: Tom McLeod (McLeod Software) on Building a Trucking Software Company That Lasts 41 Years
Jacob Benbenek
Founder/CEO of Magna
Magna
Episode: Jacob Benbenek (Magna) on Why His Reps Get Paid on Losing Loads and How He's Gone 14 Years Without Fraud
Steve Wineriter
President & CEO, American Diamond Logistics
American Diamond Logistics
Episode: Steve Wineriter (American Diamond) on Going From Stuck at $45M to a $100M Run Rate
Matthew Leffler
Law professor and expert guest on freight law and policy
Independent (law professor)
Episode: Matthew Leffler (The Armchair Attorney) on Montgomery and the New Era of Broker Liability
Brandon Wolfe
Managing partner at Jordan Partners, investor with focus on supply chain and logistics
Jordan Partners
Episode: Brandon Wolfe (Jordan Partners) on Why Freight Brokerage Is America's Most Underestimated Business
Shannon Breen
Founder and CEO of FreightVana
FreightVana
Episode: Shannon Breen on Why FreightVana is a No-Commission Brokerage and Won 150 of the Largest Shippers
Harman Cheema
CEO of Cheema Freightlines
Cheema Freightlines
Episode: Harman Cheema on Why Shippers Are Flooding Back to Asset Carriers (Cheema Logistics & Freightlines)

Host

Jesse Brown
Host of The Freight Show

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Talking Points

Recent interactions between the hosts and their guests.

Andrew Silver on Why He’s Buying a Brokerage Instead of Building One
Q: Do you build something from scratch or buy something?
Silver favors acquiring an established broker because it avoids years of building a carrier network and gives the business a foundation of customer relationships, process, and compliance. He intends to grow the acquired company toward becoming a top-five broker.
Andrew Silver on Why He’s Buying a Brokerage Instead of Building One
Q: What do you feel like you were like when you were in the driver's seat?
Silver describes himself as intense, highly competitive, and demanding, with a strong focus on excellence. He says he could also be emotionally reactive, and later feedback helped him recognize how that affected his team.
Ken Adamo (EASE Logistics) on Why You Can't Price Like a Coward
Q: What is your perspective on the impact that Montgomery is going to ultimately have on both the carrier market and the brokerage market?
Adamo expects the decision to make it harder for small and new carriers to get freight, particularly as brokers face greater pressure to document carrier selection. He believes large asset-based carriers and brokerages with established insurance and safety structures are better positioned, while small brokerages may struggle with compliance costs and vetting tools.
Ken Adamo (EASE Logistics) on Why You Can't Price Like a Coward
Q: Why is the demand factor so much more important?
Demand can create new lanes and shipments beyond what a shipper normally moves, while spot-market freight reaches brokerages after earlier routing-guide options fail. Supply-driven changes, by contrast, can move faster as trucks enter or leave service.
Matthew Leffler (The Armchair Attorney) on Montgomery and the New Era of Broker Liability
Q: How do you see regulation evolving for autonomous trucks?
Regulation will involve a mix of federal and state actions, with ongoing rulemaking around Level 4/5 autonomy, training, hours of service, and safety standards; the industry will need to engage in rulemaking processes and advocate for robust safety protections while supporting innovation.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About The Freight Show

What is The Freight Show about and what kind of topics does it cover?

Conversations focus on freight, logistics, and supply-chain leadership, featuring founders, CEOs, and senior operators who discuss strategy, policy, technology, and market dynamics. Episodes frequently explore brokerage models, carrier relationships, regulatory changes, and the evolving role of technology (AI, automation, data) in optimizing freight networks. A standout pattern is the mix of practitioner stories (scaling a brokerage, overcoming regulatory hurdles, building density) with high-signal analyses from legal, financial, and technology perspectives. This blend makes it valuable for listeners who are operators, investors, or professionals evaluating market shifts, carrier and shipper relationships, and the tech-enabled future of fre... more

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Which podcasts are similar to The Freight Show?

These podcasts share a similar audience with The Freight Show:

1. The FreightCaviar Podcast
2. BigDeal
3. All-In with Chamath, Jason, Sacks & Friedberg
4. WHAT THE TRUCK?!?
5. Freakonomics Radio

How many episodes of The Freight Show are there?

The Freight Show launched a year ago and published 33 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on The Freight Show?

Recent guests on The Freight Show include:

1. Andrew Silver
2. Ken Adamo
3. Tom McLeod
4. Jacob Benbenek
5. Steve Wineriter
6. Matthew Leffler
7. Brandon Wolfe
8. Shannon Breen

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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