Ep. #63: Tariff Talk: Cargado’s Matt Silver, Caspian’s Justin Sherlock & Gaia Dynamics’ Emil Stefanutti on Navigating Tariff Volatility

This week, Andrew sits down with Harish Abbott, CEO and cofounder of Augment, the AI teammate for logistics. Harish says, “Logistics is broken,” and in this episode, he goes deep into just how broken, talking about the inefficient ways information is shared between numerous parties on any given shipment. He talks about how overwhelmed operators are by emails and manual processes, leading to costly inefficiencies, a lack of time for creative work, high turnover, and burnout. The former CEO and cofounder of Deliverr, which was acquired by Shopify for $2.1B in 2022, is setting out to change that with Augment.In this episode, Harish shares:Why the flow of logistics information is broken and the real-world costs of its inefficiency, including missed appointments, wasted labor, and asset underutilization.How Augment aims to solve these problems with an AI teammate named Augie that can understand SOPs, manage workflows like tracking and document collection, and learn from context, freeing up human operators for judgment-based tasks.The critical importance of living out your company’s values and deeply understanding operator pain points in building scalable businesses.Insights on navigating the rapidly evolving AI landscape, balancing innovation with delivering tangible business value, and Harish's approach to fundraising for a capital-intensive AI venture.A five-year vision for Augment focused on significantly reducing waste in the $10+ trillion global logistics industry and enabling more efficient commerce.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.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 IntentTrends 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. ***