The Freight Pod

A 23-year-old with a pager, a bag phone, and a point to prove—Chris O’Brien takes us from apologizing for not owning trucks in the early days of his C.H. Robinson career, to shaping one of the most influential commercial engines in logistics, then into a new play: One Armada. We dig into the early days of brokerage at Robinson when check calls ruled and service meant relentless follow-up, and we unpack the moment that rewired Chris’s approach—working on-site at a shipper and learning to think outward first. From opening Raleigh and hiring for mission, to selling in French while integrating an acquisition, this is a masterclass in how hustle matures into scalable systems without losing its edge. We also get a rare look inside Armada’s unique model. Chris lays out why restaurant supply chains are different—SKU velocity extremes, temperature control, and LTO shocks—and how redistribution, inventory visibility, and engineering create leverage. Then we zoom into managed freight: a curated carrier base treated like strategic partners, long-term commitments that outperform spot-market whiplash, and the power of behaving like a good shipper. Add Sunset’s LTL and truckload brokerage and ATEC’s export specialization, and the strategy gets clearer: combine capabilities to win complex, multi-modal, multi-temperature flows where savings and service matter most. One Armada isn’t just a new logo; it’s a deliberate way to sell and deliver—aligning brand, enablement, and go-to-market so customers can say yes faster and teams can sell more without losing what already works. Chris shares how he designs change—listen broadly, anchor on growth, and build collaboratively—and what success looks like in two years: greater scale across industries, tighter integration, and customers and carriers saying the experience got better because Armada got smarter. If you care about freight brokerage, managed transportation, restaurant logistics, or building a sales engine that actually helps customers win, this conversation is a roadmap. Subscribe, share with a teammate who leads sales or operations, and tell us: where would you place your bet—redistribution, managed freight, or both? Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

What does it take to build a $220 million logistics company from scratch? Peter Coratola, CEO and founder of EASE Logistics, reveals the hard-earned wisdom behind his remarkable journey from unemployed college graduate to logistics leader. After being let go from his first industry job at 23, Peter launched his own brokerage with nothing but determination and a newborn son to support. His philosophy was simple yet powerful: "The more you do, the more you make." This approach became the foundation for a company that now handles hundreds of millions in freight and employs teams across brokerage, asset-based transportation, and warehousing operations. The turning point in EASE Logistics' growth came from an unexpected direction – taking on high-stakes automotive line production freight. "That's like taking your driver's ed on the Indy 500," Peter explains, describing how the unforgiving standards of automotive logistics (where line shutdowns can cost manufacturers $5,000 per minute) forged operational excellence that transferred to other industries. Peter's perspective on technology and AI reflects his commitment to customer service above all else. While embracing innovation internally to make his team more effective, he remains cautious about technology replacing the human connections that differentiate his business. "It's easier for logistics companies to be good today, but harder to be great," he observes, pointing to EASE's true 24/7 operations with 25% of staff working night shifts to ensure problems get solved, not just acknowledged. As market conditions continue to challenge freight brokers, Peter's leadership lessons offer valuable insights for anyone building a business. The hardest moments weren't market crashes but people decisions – learning to balance emotional investment with necessary business choices. His advice for navigating tough times? "Stick to the plan, not your mood," and focus on putting points on the board every day through small wins. What will the freight market do next? Peter sees challenges continuing through 2025 but anticipates improvement by mid-Q1 2026, particularly with automotive manufacturers launching 27 new models. For those weathering the current market, his story demonstrates that preparation, adaptability, and maintaining team swagger through continued investment can position companies to thrive when conditions improve. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

How do you build a billion-dollar freight brokerage without a single dollar of outside capital? Sean McLeod, who joined Axle Logistics as employee #21 in 2016, gives us a rare glimpse into one of the fastest-growing and most respected brokerages in North America. Sean shares the extraordinary journey of scaling Axel from a small operation with 20 people to a powerhouse with nearly 700 employees. What makes this story particularly fascinating is how Axle has maintained its cradle-to-grave model at scale – something many industry veterans claim is impossible. "Everyone says you can't operate a billion-dollar company cradle-to-grave," Sean explains. "Yeah, you can—you just keep hiring people." We dig deep into Axle's counter-cyclical approach to downturns, where they double down on customer visits and hiring while competitors pull back. This strategy led to explosive growth during COVID, with the company growing from $176 million to $521 million in just one year. Sean's philosophy is refreshingly straightforward: "Volume is everything. The market dictates my rate and profit. All I can do is continue to find new business." The conversation takes an emotional turn when Sean discusses his leadership style, revealing how deeply he cares about his employees, customers, and carriers. He still makes cold calls alongside his team, books freight, and holds everyone (including himself) accountable to the company's high standards. His authentic passion becomes clear when he admits, "I probably care too much, but that's all right." Whether you're running a small brokerage or a large logistics operation, this episode offers invaluable insights on maintaining culture through growth, balancing compensation between different operational models, and strategically adopting technology without sacrificing the human touch that makes freight brokerage work. Ready to be inspired by a freight success story built on grit, service excellence, and unapologetic commitment to people? This episode will challenge your assumptions about what's possible in building a brokerage in today's market. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

Andrew Leto shares his journey from Navy veteran to successful freight entrepreneur, revealing how he built Global Tranz from zero dollars into a half-billion-dollar business by spotting opportunities in the eBay shipping market and creating an agent-based model that revolutionized LTL freight.  • Starting with no money but securing prepayment from customers while getting delayed payment terms from carriers created instant working capital • The agent model allowed rapid growth by recruiting sales reps who brought their book of business for higher commissions • Building 10-4 Systems as a visibility platform that was later acquired by Trimble in 2017 • Creating Emerge as a procurement platform that offers shippers a free RFP system while generating revenue from carrier participation • Napoleon Hill's "Think and Grow Rich" provided the mindset foundation for success through belief and visualization • AI will transform freight by potentially eliminating 70% of current jobs while creating new opportunities • Investment strategy focuses on knowing the industry deeply and finding undervalued assets like Roadrunner • Future freight brokers will need to operate on 5-6% margins as AI creates price transparency across the market If you have an interest in entrepreneurship, Leto recommends reading "Think and Grow Rich" by Napoleon Hill, which he considers more valuable than a college degree for anyone seeking success. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

This week, Andrew has a candid conversation with Jett McCandless, CEO and founder of project44, about his freight journey, from making $12 an hour at Roadway Express to building a global supply chain network that powers more than 1 billion shipments across 180+ countries each year. Jett opens up about growing up on food stamps in Section 8 housing, the hard-earned lessons from his exit at GlobalTranz, and the bold vision behind project44’s next frontier: Movement, its Decision Intelligence Platform. In this episode, Jett shares: The story of GlobalTranz's rapid growth, the complexities of its sale, and how that experience fueled his next move. How project44 evolved from an LTL API tool into a global visibility platform and now into the newly launched Movement, an AI-powered decision engine. Why “visibility” today means more than track and trace and how true supply chain intelligence includes inventory in motion, predictive insights, and transaction-level optimization. His big vision and response to industry buzz around project44 becoming an “operating system” for logistics and why that vision could shift power dynamics in the industry.  A bold take on the future of transactional brokerages and why tech-forward disruption is just getting started. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

This week, Andrew is joined by Sean Henry, CEO and founder of Stord, a major player in omnichannel fulfillment and supply chain technology. In this episode, Sean shares his incredible entrepreneurial journey, which started by selling Christmas presents on eBay at age seven to launching Stord in 2015 as a student at Georgia Tech. In this episode, he reflects on the company’s early days, turning points, and what’s next following Stord’s recent $200 million fundraise and major acquisition of Ware2Go from UPS. In this episode, you’ll hear from Sean on: How a few Christmas sales on eBay, plus a few other ventures, sparked his entrepreneurial drive and how mentors like Ted Alling shaped his approach to leadership. The founding premise of Stord: helping brands compete with Amazon-level logistics by offering flexible, tech-powered fulfillment solutions. How Stord evolved from an asset-light model to owning facilities and building a robust software platform to deliver a Prime-like experience to companies of all sizes. What it takes to make big business decisions, including how he thinks through market shifts, customer obsession, and staying committed to a long-term vision. His advice for entrepreneurs: don’t be afraid to ask, learn from people one step ahead, and “just start.” Iteration and momentum are everything. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

Andrew welcomes Clay Curran, CEO and cofounder of FreshX, a young company tackling the tricky reefer LTL space. Clay shares his entrepreneurial journey, marked by a willingness to pivot that has shaped both his personal career trajectory and the FreshX business model. Today, FreshX is a marketplace that connects brokers with more than 80 reefer LTL carriers. In this episode, Clay also covers: His path to entrepreneurship and early lessons learned from his entrepreneurial parents. The evolution of FreshX, including two major pivots from a last-mile delivery carrier to a reefer LTL brokerage, and finally to its current iteration as a tech-driven marketplace. The challenges and nuances of the reefer LTL market, including carrier specialization, capacity visibility, and the difficulties brokers face in sourcing reliable options. How FreshX is working to unlock hidden capacity and digitize pricing by building relationships with more than 80 reefer LTL carriers and providing a "Google Flights-like" platform for brokers. His advice for aspiring entrepreneurs in the freight industry, emphasizing the importance of good advisors, rapid iteration, and deeply understanding the real problems you're trying to solve. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

This week, The Freight Pod flips the mic as host and former Molo Solutions CEO Andrew Silver becomes the guest. Hosted by colleague and friend Derek Zetlin, this candid conversation dives deep into Andrew’s journey through freight, including growing up around logistics, learning the ropes at Coyote, and ultimately founding, scaling, and selling Molo Solutions. In this episode, you’ll hear Andrew talk about: His early experiences and pivotal moments at Coyote Logistics, from being a high school-aged intern to learning from key mentors and the challenges of early career growth. The decision to leave Coyote and his motivations behind founding MoLo, including the itch to build something independently and overcome his own personal insecurities. The early days of MoLo, the importance of culture, and the strategies behind the company’s rapid and transformative growth, going from $5M in revenue in 2017 to $625M in 2021. His reflections on leadership, the pressures of being a CEO, and the acquisition of MoLo. His perspective on the evolving freight brokerage landscape, the potential impact of AI, the future of the industry, and his own next steps. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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.” Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. *** This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net. ***

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. ***This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. Visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check them out at metafora.net.

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. Follow The Freight Pod and host Andrew Silver on LinkedIn. ***This episode is brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services. Visit gorapido.com to learn more. *** A special thanks to our additional sponsors: Cargado – Cargado is the first platform that connects logistics companies and trucking companies that move freight into and out of Mexico. If you move Mexico freight or are planning to, visit cargado.com to learn more. Greenscreens.ai – Greenscreens.ai is the AI-powered pricing and market intelligence tool transforming how freight brokers price freight. Want to see how it works? Visit greenscreens.ai/freightpod today! Metafora – Metafora is a technology and business consulting firm that has delivered value for over a decade to brokers, shippers, carriers, private equity firms, and freight tech companies. Check ...

Andrew welcomes Paul Singer, CEO and cofounder of FleetWorks, a carrier-facing voice AI agent. It’s been a year and a half since Paul and his cofounder Quang Tran tested the idea for FleetWorks. They signed up for a load board, posted an attractive load, and to their surprise, three carriers responded and negotiated with their AI agent — a product Paul calls “janky” compared to what they have today. “Ever since those three calls, we’ve been off to the races.”  On this episode, Andrew and Paul cover: The recent DeepSeek announcement and why it’s a foundational moment for AI Paul’s biggest takeaways from his four years working in carrier product for Uber Freight What separates FleetWorks from other AI companies and how it's returning 10x the ROI in operating costs for its broker-customers The biggest challenges the FleetWorks team has faced so far Can a brokerage with a sophisticated tech team build AI on its own? Follow The Freight Pod and host Andrew Silver on LinkedIn. ***Episode brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services.***

On this episode, recorded live from Manifest: The Future of Supply Chain & Logistics, Andrew interviews nine founders about their budding startups: Ed Burns with TruSygnal, a connection platform for shippers and carriers Tom Curee with Qued, automated appointment scheduling through AI Omar Singh with Get Real Rates, an API pricing tool Chip Reeves with Enablers, logistics human and AI staffing Alex Bezzubets with myMechanic Inc., a roadside assistance platform Shan Wu with Forward Labs, a brokerage sales prospecting tool Sadie Frank with N4EA, predictive intelligence tools for climate risk Thomas Mella with TrackFlo, a track-and-trace optimization platform Annalise Sandhu with Chain, AI-powered freight booking and visibility Follow The Freight Pod and host Andrew Silver on LinkedIn. ***Episode brought to you by Rapido Solutions Group. I had the pleasure of working with Danny Frisco and Roberto Icaza at Coyote, as well as being a client of theirs more recently at MoLo. Their team does a great job supplying nearshore talent to brokers, carriers, and technology providers to handle any role necessary, be it customer or carrier support, back office, or tech services.***