In this episode, Andrew welcomes Matt O’Mara, CEO and founder of Whimsy Intermodal and Whimsy Trucking. Matt’s journey into the transportation industry began in 1994 when he worked as an owner-operator for a trucking company. When that company was acquired and its drivers let go, Matt seized the opportunity to start Whimsy Intermodal in 1996 and hired many of those drivers. Today, Whimsy has about 50 company drivers, 145 owner-operators, and 150 trucks. 

Andrew and Matt also cover:

• Whimsy’s organic business growth and unique capability in handling challenging freight, the importance of finding consistency, and Whimsy’s focus on execution, including how they add value beyond transportation.
• The significant challenges Matt ran into of implementing new TMS systems in a legacy company, the importance of team buy-in, and the eventual success of digitizing and going paperless, including leveraging AI for order entry and real-time driver coaching.
• Treating drivers with respect and providing robust support as the key to retention, highlighting the reason why Whimsy has a waiting list for owner-operators.
• The importance of transparency, leading by example and avoiding hypocrisy, and the critical role of communication, emotional intelligence, and self-awareness in leadership.
• Current market conditions, the lack of impact from Chinese New Year, potential tariff effects, and the critical need for robust infrastructure and processes.

In this episode, Andrew welcomes three seasoned logistics leaders with a unique perspective, having all started on the brokerage world before transitioning to the shipper side: Nicole Schuman, transportation procurement manager at Reser’s Fine Foods; Marco Vargas-Avila, director of U.S. logistics at Dole Packaged Foods; and Andrew Dafnos, director of supply chain at KeHE Distributors.

Andrew and the panel cover:

• Balancing cost vs. service, the importance of understanding different provider models (asset vs. non-asset), and strategic bid cycle planning.
• How shippers evaluate potential partners, the critical role of transparency, and why understanding a shipper's specific network needs (not just offering a truck) is key.
• Direct feedback on what makes cold outreach successful, common pitfalls to avoid, and the power of demonstrating genuine understanding before pitching.
• Perspectives on how the logistics landscape is changing and preparing for future trends.

In this roundtable-style episode, Andrew brings together a panel of industry experts at the center of cross-border shipping and trade compliance: Matt Silver, CEO and cofounder of Cargado; Emil Stefanutti, CEO and cofounder of Gaia Dynamics; and Justin Sherlock, CEO & cofounder of Caspian.

These leaders break down how complex, ever-changing global trade regulations are impacting shippers, brokers, and carriers and how AI is being used to bring order to the chaos. From tariff classifications and regulatory confusion to duty refunds and compliance risks, this episode uncovers the real headaches businesses face and the tech that's helping them navigate it.

Andrew’s conversation with Matt, Emil, and Justin covers:

• The challenges businesses face in navigating the volatile landscape of tariffs and trade regulations, including the complexities of product classification and the impact of geopolitical events.  
• How AI is being used to streamline trade compliance processes, offering solutions to automate classification and other time-consuming tasks.  
• The impact of recent tariff announcements on businesses, with real-world examples illustrating the challenges companies face in managing increased costs and supply chain disruptions.  
• Insights into the potential implications of trade policies and the importance of adapting to the evolving global trade environment.

In this episode, Andrew welcomes Charley Dehoney, CEO and cofounder of Upwell. Charley has worked at brokerages like Worldwide Express. He bootstrapped his own brokerage, Dehoney Transportation Management. He bought and sold the 50-year-old Mannings Truck Brokerage. He’s worked for a digital freight startup, a supply chain accelerator, and a container shipping company. And that’s not even all of it. Across every chapter, one thread stands out: Charley’s intimate understanding of freight payments and the cash flow challenges that logistics companies face.

So when Charley reflects on his career, it’s clear why it’s led him to where he is today. As he puts it, “The sum of all of those experiences have positioned me uniquely to do exactly what I’m doing at Upwell.” 

In this conversation, Andrew and Charley also get into:

• The trust problem in freight and why we need more API: Assume Positive Intent
• Trends across the rise of managed transportation, broker consolidation, and the old guard versus the new guard of brokerage ownership. 
• How Upwell is tackling the freight payments problem — and the cash flow lessons Charley learned the hard way (including selling his Mercedes in front of his own brokerage).
• A candid take on VCs in freight: why they’ve earned a bad reputation, when they make sense, and how to spot the good ones.
• Tactical advice on fundraising — how much to raise, how long it should last, and what investors really expect in return. 
• Why starting a business in a down market might be the smartest move you can make. As Charley says, “You never want to waste a good crisis.”

In this episode, Andrew sits down with Greg Paulson, CEO of Giltner Transportation, a transportation and logistics company based in Jerome, Idaho. Greg’s journey with Giltner began in 1999 when, as an accountant, he worked closely with then-owner Doug Blevins, who eventually offered him a job. Now, 26 years later, Greg and his wife, Shawna, own and lead the company.

Giltner started in 1980 as a milk tanker transporter and has since expanded into a 300-truck reefer fleet, a $250M brokerage, a $100M factoring business, and an insurance and compliance arm helping small carriers.

In this episode, Greg also shares:

• Hard lessons learned from Giltner’s toughest challenges, including near-bankruptcy in 2003 and how the company rebounded.
• The four pillars of a successful trucking business and his philosophy on business. 
• What he’s learned from running a trucking business, like navigating bid cycles, developing smart bidding strategies, managing the emotional toll of losing key lanes, and why a diversified network is key to long-term stability.
• Operating an asset-based trucking company alongside a brokerage and the pros and cons of company drivers vs. owner-operators.
• Growing a factoring business to 300 trucks without any sales or marketing, just by word of mouth.
• Trucking’s biggest safety challenges today, including the impact of nuclear verdicts and how Giltner is investing in technology to protect its drivers.
• Advice for entrepreneurs looking to start and scale their own trucking businesses.

Andrew sits down with Jin Stedge, CEO and cofounder of TrueNorth. Jin grew up in a family of owner-operators, including her dad, uncles, and grandparents, but didn’t see herself in the family business. Instead, she headed to MIT, earned an aeronautical engineering degree, and built her career in consulting, HR tech, and — autonomous trucking. But Jin knew truckers had more immediate needs and that's how the industry pulled her in. 

In this episode, Jin also talks about:

• The evolution of TrueNorth, which evolved from being a carrier to an AI load board with a virtual dispatcher named Loadie, and what she hopes the business looks like five years from now.
• The biggest challenges of building a load board, the necessary features and qualities of an AI load board, how TrueNorth approaches fraud, and what new solutions could improve load boards.
• How technology should enhance rather than replace the human connection to make freight relationships more successful.
• Raising a $50M Series B with Sam Altman as an early backer, how she made the decisions to use the money and what she may have done differently, and best practices for staying in touch with investors, including her “Weekly Reflection.”
• Running the business through maternity leave and early motherhood.

In this episode, Andrew welcomes Dan Manshaem, CEO and founder of Ally Logistics, for his first podcast appearance ever. In 2012, Dan and his cofounder Jeff Chidester started Ally — they quit their jobs, put $2,500 in the bank, and signed a lease for $300 a month for some office space. He calls that time, “One part exhilarating, one part terrifying.” Today, Ally has grown to a team of 95 with a projected top-line revenue of $145M in 2025. 

In this episode, Dan shares:

• How his initial finance career aspirations led him to freight brokerage, starting as an intern before founding Ally Logistics.
• Practical tips for launching a brokerage, winning early customers, and differentiating in a competitive market. 
• How Ally integrates AI tools like FleetWorks and Qued to enhance operational efficiency, how Ally team member roles have evolved to support AI, and the biggest challenges in implementing new tech.
• His perspective on selecting tech providers, managing vendor relationships, and using a “super user program” for smoother integrations.
• How he thinks about remote work in 2025 and Ally’s approach with “earned flexibility.”
• Valuable advice for interns and young professionals entering the logistics world.

Andrew welcomes Krenar Komoni, CEO and founder of Tive, to The Freight Pod. Krenar left Kosovo at 17 years old to pursue his education in the U.S., but the aspiring entrepreneur knew he’d be back one day to create jobs in his home country. 

Krenar went on to earn degrees in computer engineering, math, and electrical engineering and discovered a passion for radio frequencies and wireless communication systems. But it was his father-in-law's trucking company and the constant tracking calls — where’s the truck? Will it be on time? — that led Krenar to build him a GPS tracker. And that's how Tive started in 2015. Today, Tive supports more than 900 customers from its offices in Norway, Mexico, South Africa, Boston — and Kosovo.

In this episode, Krenar also shares:

• The early days of Tive: bootstrapping, landing the first customer, and building Tive’s innovative trackers.
• Tive's near-collapse in 2019 and the moment that turned things around.
• Building a global, remote team and culture across Tive’s offices.
• The biggest mistakes a CEO or founder can make, Krenar’s advice for founders and entrepreneurs, the journey to product-market fit, and how Tive has built a moat around its tracking capabilities.
• Krenar’s vision for the future of visibility and AI, and what’s next for Tive.

In part two of this special two-part episode, Andrew continues his conversation with his dad, Jeff Silver, CEO and founder of Mastery Logistics Systems. Part two picks up with the founding and rapid growth of Coyote Logistics, a company that redefined the industry's expectation of service with its "No Excuses" mentality. Jeff says the experience was “magical the whole time.” 

After UPS acquired Coyote in 2015, Jeff could have easily retired, but as he says, he doesn’t like golf. In 2019, Jeff started Mastery Logistics Systems to tackle a really hard problem: building a modern transportation management system for enterprise carriers, brokers, and shippers.

In this episode, Jeff also talks about:

• How Coyote’s "No Excuses" mentality fueled its growth and changed the industry, what made a great Coyote hire, and his proudest Coyote moments.
• Why freight brokers really exist, what shippers need from a brokerage, and how digital brokerages have gotten this wrong.
• The challenges of building technology for asset-based carriers and how Mastery balances its product roadmap with customer expectations.
• His take on AI’s impact on freight, brokerage’s future in the next five to 10 years, and when autonomy will truly change the game.
• His advice for the next generation of logistics entrepreneurs and what he’s proudest of in his 40-year career.

In this special two-part episode, Andrew sits down with his dad, Jeff Silver, CEO and founder of Mastery Logistics Systems. This is part one, beginning with Jeff’s life in 1980 at the University of Michigan. 

In 1984, Jeff joined Paul Loeb and others in building what became American Backhaulers, one of the industry’s first and most successful freight brokerages. C.H. Robinson acquired American Backhaulers in 1999, and a key driver of that industry-changing deal was Express, the technology system built by Jeff and his team that helped accelerate C.H. Robinson’s growth for years to come.

In this episode, Jeff also shares:

• His college years at the University of Michigan, passion for language, and early jobs scrubbing yachts and painting houses.
• How he got started at American Backhaulers and what led him to write the industry’s first load-matching algorithm. 
• The lasting impacts of American Backhaulers that live on in the industry today and how its acquisition by C.H. Robinson unfolded. 
• What makes a great seller and the book that changed his view of sales.
• His time at MIT, pursuing a master’s in engineering and logistics, and the path to founding Coyote Logistics, which was acquired by UPS in 2015.
• The challenges that Mastery Logistics Systems is tackling today for major trucking companies like Werner, Schneider, and others.