The Freight Pod

This week, Andrew welcomes Hannah Testani, CEO of Intelligent Audit. Hannah dreamed of becoming CEO of Lehman Brothers, so she studied finance at Carnegie Mellon and got a job at Goldman Sachs in 2008, just as the financial world was crashing. Though she had zero initial interest in supply chain, she pivoted to join her father's small, three-person company, Intelligent Audit. Starting from those early days of having to prove herself, Hannah shares her story of transforming Intelligent Audit into a global leader in freight audit, business intelligence, and AI-powered optimization.In this episode, Hannah shares:Her early career pivot from Goldman Sachs during the 2008 financial crisis to joining her father's company, Intelligent Audit, and the initial challenges of proving herself in a new industry.The critical moments that forced Intelligent Audit to mature and redefine its vision, including losing a major customer and the strategic decision to buy out sales channels to control their own destiny.How Intelligent Audit has embraced technological evolution, from leveraging machine learning seven years ago to now integrating advanced AI to enhance everything from customer service to product development.Her experiences and advice as a young female CEO in a traditionally male-dominated industry, focusing on turning perceived disadvantages into opportunities and the importance of perspective.The transformative power of implementing the Entrepreneurial Operating System (EOS) at Intelligent Audit and her vision for a future where the company is even more self-serve and empowers customers through data.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 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. ***

Clay Curran, CEO and co-founder of FreshX, dives into the dynamic world of refrigerated LTL logistics. He shares his entrepreneurial path and highlights the pivotal changes FreshX underwent to become a tech-driven marketplace connecting brokers with over 80 carriers. Discussing the challenges of capacity visibility and specialization in the reefer market, he outlines how FreshX aims to unlock hidden capacity. Clay also offers valuable advice for aspiring entrepreneurs, stressing the importance of adaptability and understanding real industry problems.

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. ***

This episode features Marco Vargas-Avila from Dole Packaged Foods, Nicole Schuman of Reser’s Fine Foods, and Andrew Dafnos from KeHE Distributors, all seasoned experts in logistics. They dive into the intricate balance between cost and service, the importance of transparent partnerships, and strategies for successful cold outreach. Their insights touch on navigating the shifting logistics landscape, adapting to customer needs, and leveraging technology to enhance efficiency in food shipping.

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. ***