Episodes
273
Latest episode
Oct 2026
Language
EN-US
The FreightCaviar Podcast interviews founders, executives, and decision-makers in the freight and shipping industry. New episodes are released every Monday at 5 a.m. CT and are available on YouTube, Spotify, and Apple Podcasts. Also, subscribe to our free freight broker newsletter on FreightCaviar.com.
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 pbj@freightcaviar.com
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 pbj@freightcaviar.comCHAPTERS: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 pbj@freightcaviar.com .
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 pbj@freightcaviar.com
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.
Freight brokerage founder John Ferguson breaks down how Pivot Supply Chain Solutions grew to $50M, why cold calling and customer service still win in logistics, and where AI fits into the future of freight brokerage. John also opens up about how freight brokering changed his life, from spending time in foster care and struggling as a young adult to building a career, a family, and his own company. Now, after checking off many of the milestones he set for himself, he says the next thing left to chase is a $1B freight brokerage. This week's episode is sponsored by Epay Manager, Goodship, Highway, and Bitfreighter.
Lev Krasnopolskiy, Co-Founder of Everest Transportation Systems and Founder of Alpha Staffing and Recruiting, shares how he went from immigrating to the U.S. from Moscow at five years old to building a career in freight, co-founding Everest, and using offshore talent in Ukraine to help the brokerage compete and scale.Lev also breaks down how chess shaped his approach to sales and negotiation, how speaking Russian helped him build relationships with carriers, why he believed Ukraine could give Everest more firepower for less money, and why he thinks freight offshoring isn't going away. He also shares his views on offshore fraud, building a global logistics workforce, launching Alpha after Everest, and combining offshore staffing with domestic recruiting.This week's episode is sponsored by Epay Manager, Highway, Bitfreighter, and Chain.Interested in sponsoring our podcast? Send us an email at pbj@freightcaviar.comCHAPTERS:0:00 Intro1:09 Meet Lev Krasnopolskiy2:38 From Moscow to America4:58 Geography, History, and Early Ambition7:43 Chess and Learning to Sell11:57 Breaking Into Freight at Echo14:05 Building Carrier Relationships15:55 From Echo to Custom19:22 Founding Everest Transportation Systems21:18 Learning Customer Sales24:49 The Ukraine Staffing Experiment30:42 Moving the Team to Ukraine34:04 How Ukraine Helped Everest Scale37:49 What Held Everest Back40:12 Why Freight Offshoring Won't Stop43:19 Freight Becomes a Global Industry45:03 Offshore Fraud and Regulation48:25 Starting Alpha Staffing and Recruiting52:22 Offshore and Domestic Recruiting56:02 The Future of Alpha57:33 Lev's Formula for Success58:49 The Four-Hour Workweek1:01:05 Final Thoughts
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