The FreightCaviar Podcast

Michael Cherney, Co-Founder and CEO of Cooler Logistics, shares how his team grew a food and beverage focused brokerage to a $25 million run rate in three years without posting loads on load boards, how a network built on repeat carriers has kept them free of stolen freight, and why relationships with carriers and shippers still matter more than any tech stack.
Michael also breaks down his path from employee number seven at Load Delivered to first-time CEO, the tough first year that led him to rebuild his entire carrier team, how walking industry trade shows without a booth became a pipeline for new shippers, when a small brokerage is ready for enterprise freight, and why long-term carrier relationships matter more than quick fixes.'
This week's episode is sponsored by Epay Manager, Goodship, Resolve Logistics and TrackFlo.
Interested in sponsoring our podcast? Send us an email at [email protected]

Gabrielius Stonys, Co-Founder of Spotter Labs, shares how he turned an AI dispatching startup into a 650-truck operation while carrier profitability collapsed 80%, and why he believes scaling down is guaranteed death in trucking. Gabriel also breaks down arriving in Chicago at 12 barely speaking English, meeting his co-founder as a random teammate in Dota 2, raising a $2.5M pre-seed round in 2020, why carriers had zero appetite for automation during the COVID freight boom, and why he thinks autonomous trucks could make up 30% of the market within five to eight years.
This week's episode is sponsored by Epay Manager, Bitfreighter, Goodship and Highway.
Interested in sponsoring our podcast? Send us an email at [email protected]

What separates preferred transportation providers from the rest?

In this conversation with Kevin Mitchell, Director of Transportation at James Hardie, and Derek Zetlin, Director of Sales at GoodShip, we take an inside look at how leading shippers evaluate providers, balance relationships with performance data, and decide who earns more freight. 

Peter Stefanovich, President of Left Lane Associates, shares what it takes to sell a freight brokerage, from the EBITDA most buyers need to see before they get interested to the multiples owners can realistically expect and the risks that move a valuation up or down. Peter also breaks down how Left Lane has advised on 88 transportation and logistics transactions since 2016 totaling just over $2 billion in enterprise value, how near-zero interest rates fueled the 2021 deal boom and set up the freight recession that followed, what the Montgomery ruling means for brokers and buyers, the landmark deals that shaped freight M&A from UPS buying Coyote to Echo acquiring ITS, and why he sees 2027 and 2028 as strong years to exit.

This week's episode is sponsored by Epay Manager, Bitfreighter, Resolve Logistics and TrackFlo.

Interested in sponsoring our podcast? Send us an email at [email protected] 

Dan Manshaem, Co-Founder/CEO of Ally Logistics and Founder of Resolve Logistics, joined Paul-Bernard Jaroslawski and Lev Krasnopolskiy on the FreightCaviar Podcast to discuss how he started a freight brokerage in 2012 with $5K in the bank and grew it to a $300M+ run rate, what he thinks brokerage will look like in 10 to 20 years, his unconventional take on non-competes, and more.

Chris Brewer, Founder & CEO of River City Logistics, joined Paul-Bernard Jaroslawski, Lev Krasnopolskiy, and Reed Loustalot, to discuss how he built a logistics company without outside investment, Chris’ thoughts on AI, and more.

Thomas Mella, Co-Founder at TrackFlo, and Rich Joseph, Chief Commercial Officer and Co-Founder at TrackFlo, joined Paul-Bernard Jaroslawski and Reed Loustalot on the FreightCaviar Podcast to discuss how TrackFlo helped one brokerage cut track-and-trace headcount by more than half while improving service, what acquisitions like Descartes/Tai reveal about the value behind freight-tech M&A, and why distribution matters in an AI-driven software market.

This week's episode is sponsored by Epay Manager, FreightFlex, Goodship, and Highway.Interested in sponsoring our podcast? Send us an email at [email protected]:0:00 Intro0:42 Meet Thomas Smella and Rich Joseph1:51 Why Freight Tech Companies Sell for $100M5:59 The $100M Freight Tech Playbook9:05 Why TrackFlo Focuses on One Problem11:56 What TrackFlo Actually Does15:28 How TrackFlo Started16:40 From TrackFlo Customer to Executive18:05 Cutting Track & Trace Staff by 50%+23:09 Bootstrapping a Freight Tech Company25:38 The Anti-SaaS Playbook27:47 Can You Vibe Code a TMS?33:53 The Future of Freight SaaS35:31 Why Expertise Still Matters in the AI Era38:18 How VC Funding Changes the Incentives40:56 The Tradeoffs of Raising Capital45:00 How Far Will AI Really Go in Freight?48:03 Could Freight Brokers Be Displaced?51:39 The LinkedIn Debate57:08 Should a SaaS CEO Build a Personal Brand?1:07:42 Final Thoughts

Michael Grace, Chief Compliance Officer at FreightFlex, explains how freight fraud evolved from double brokering into organized cargo theft, why so much freight theft is preventable, and how carrier vetting has changed over the past decade. He also shares why freight brokers are facing greater compliance and liability risks, how stricter carrier selection standards are changing the market, and why shippers are increasingly looking for brokers with documented compliance processes. The conversation also covers non-domiciled carriers, and the one rule Michael believes every freight broker should follow.
This week's episode is sponsored by Epay Manager, Goodship, Highway, and TrackFlo.
Interested in sponsoring our podcast? Send us an email at [email protected].

Andrew Leto, Founder of Emerge, GlobalTranz, and Felix AI, explains why bringing AI to carriers could be one of the biggest opportunities in trucking and logistics, and why digitizing the carrier side of freight could reshape how the entire market operates.
Andrew also breaks down how AI agents could help carriers access more loads, negotiate better rates, and improve yield, why so much of trucking still runs manually, and why carriers have been slower than brokers to adopt new technology. He also shares why freight brokerage margins could fall from 12–13% to 8–9%, what that means for hiring and headcount, and how AI could change the structure of freight brokerage without necessarily triggering mass layoffs.
The conversation also covers why carrier data remains a major competitive advantage for large brokers, whether AI could create more freight brokerages instead of fewer, the risks brokers take on for shippers, and why Andrew believes the next major wave of freight technology will be built around carriers.
This week's episode is sponsored by Epay Manager, Bitfreighter, FreightFlex, and TrackFlo.
Interested in sponsoring our podcast? Send us an email at [email protected] 

What does it take to make brokerage growth look easy?Join Epay Manager for a discussion on how freight brokerages are using automation to handle more volume without building a bigger back-office team. We will share real client growth stories, including how River City Logistics increased load volume by approximately 70% without adding back-office headcount.Then, we are settling the freight industry’s greatest debates. What is the GOAT freight snack? Freight phrase? Acronym? Logistics movie? Come ready to share your picks.