The Freight Pod

Drew Wilkerson, former sales guy turned CEO of a publicly traded brokerage, shares his incredible success story. He discusses his rise to the top, the importance of transparency and alignment in leadership, managing through COVID, making difficult decisions, and dealing with investors.

Another (mostly) AI-written episode description:We're thrilled to bring you this discussion with Bill Driegert, EVP, Head of North America at Flexport. Bill was previously the 4th employee at Coyote Logistics and then co-founder of Uber Freight. He takes us on an enthralling journey through his illustrious career and the landscape of the freight industry. This episode packs a punch, offering you an exclusive peek into the challenges, triumphs, and future of the freight market. Whether you're a logistics pro or a curious bystander, get ready to be enlightened on tech's role in advancing this traditional industry.Imagine the excitement of being part of Coyote Logistics' initial days or the thrill of breathing life into Uber Freight! This episode takes you there! Bill candidly shares his insights about Coyote's pioneering journey, from attracting the right talent to the challenges of launching a brokerage from scratch. Discussion further navigates through the inception of Uber Freight, shedding light on their vision of disrupting the freight industry. We also touch upon the trials of automating the carrier experience, the potential of AI in transportation, and the delicate balance between technology and personal touch in customer care.Our conversation doesn't stop there! We dive into the nitty-gritty of pricing models, the pros and cons of tech fragmentation, and the changing dynamics of owner operators in the market. As we further dissect the operational intricacies, Bill shares his hopes after acquiring the Convoy technology and the role it can play within Flexport. The discussion wraps with a glimpse into the future of transportation, the potential of autonomous vehicles, and the impact of digital models. Brace yourself for this rollercoaster of insights, stories, and perspectives from another great guest.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. ***

Matt Pyatt, CEO of Arrive Logistics, shares valuable lessons learned in early businesses, the story behind founding Arrive Logistics, strategic approaches to scaling business growth, potential disruptions in the freight industry, and his vision for the future of Arrive. Join for this stimulating conversation on building a successful business and planning for the future.

With Andrew attending the Freightwaves conference in Chattanooga, we start the episode sharing stories of our experiences at industry conferences. We talk about what it's like to be a broker and shipper at these events, and how to make the most of your time when attending. Our guest for the episode is Meredith Neizer, Chief Logistics Officer at Armada. Meredith has had a fascinating career in the industry, but taking it back to her youth, we talk about how she broke barriers as the first female to ever attend the U.S. Merchant Marine Academy. This set the tone for the rest of her career, as she came into a male-dominated industry and found ways time and again to break glass ceilings for herself. We talk about the value of mentorship, networking, and taking chances on yourself. Meredith highlights how a solid network can be a game-changer in one's career trajectory. We also delve into the need for increased diversity in the logistics industry and the steps necessary to achieve it. From exploring the latest innovations in supply chain solutions to discussing effective sales strategies in freight, this episode provides a wealth of knowledge. So, buckle up for an episode brimming with inspiring stories, valuable advice, and game-changing experiences.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. ***

AI-written episode description:Success rarely follows a straight path. Our guest, Cameron Ramsdell, will attest to that. As the CEO of Armstrong Transport Group, he has weathered the storm of transitions, been shaped by mentorship, and emerged as a leading voice in the industry. Journey with us as we explore the winding road of his career, starting from his time at Coyote Logistics, leading a new division at US Xpress, and finally clinching his role at Armstrong Transport Group. Delve into the topic of mentorship and its profound influence on career progression. Cameron discusses how the guidance and support of mentors and peers has helped him grow and steer through the complexities of the industry. We dig into the evolution of Coyote, the freight brokerage industry's transformation over the years, and the impact of refusing to say no when faced with a challenge. In the second half of our conversation, we zero in on Cameron's experience navigating new roles and organizational changes amidst uncertain times. He shares the personal sacrifices he made while relocating from Chicago to Atlanta. Cameron's story of transitioning from a legacy business to a dedicated division is a testament to resilience and adaptability. We wrap up by exploring his current role at Armstrong Transport Group and his vision for its future. An episode jam-packed with insights from the logistics industry awaits you. Get ready to be inspired!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. ***

AI takes the helm to write another captivating episode description for us. Enjoy Episode 6:Ever wondered how one man could turn a company from the brink of bankruptcy into a thriving venture? Enter Mitch Luciano, the CEO of Trailer Bridge who did exactly that. Our chat with Mitch goes beyond the usual corporate jargon and delves into his journey of securing the helm of a ship that was almost sinking. From his audacious move of joining a company going through its worst phase to transforming its toxic culture, Mitch's narrative is a testament to how leadership can make or break a company. Stick around as we unravel his transition from a "carrier guy" to a key decision-maker in the freight industry.But that's not all. Our conversation takes an interesting turn as we explore the nitty-gritty of the freight industry. Unveiling the often blurred lines between brokerage and asset sales relationships, Mitch shares his insights on the significance of transparency and trust in these complicated dynamics. He also explains the unique challenge of owning assets, the cost involved, and how it often leads to the downfall of brokerage businesses. Intrigued? Buckle up for an enlightening discussion.Lastly, we steer the conversation towards the softer aspects of business. Ever given a thought to how love could be a driving force in a business setting? Mitch's emphasis on people, accountability, and even his rather unconventional idea of getting an ice maker, paints a vivid picture of how trust and love can transform a company's culture. From writing birthday cards to his employees to revealing his decision-making process, Mitch's leadership style is a refreshing take on corporate leadership. So, if you're up for a candid chat about freight, leadership and even a secret pasta sauce recipe, this episode is a must-listen!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. ***

Former Convoy employees Ryan Soskin and Zach Knobel share the inside story of Convoy's journey and how it ran out of cash. John Marrinson discusses the challenges ahead for brokers and carriers, including rising interest rates and squeezed margins.

Another AI-written Episode Description for you this week:We are joined this week by Ryan Daube, founder of Advantage Freight Network (AFN) and 240 Logistics. Listen in as Ryan, an Indiana University alumnus and former American Backhaulers employee, takes us through the trials and triumphs of his entrepreneurial journey. From scaling AFN to a staggering $250 million to his latest venture in the cannabis market, Ryan's story is one for the books!Tune in as he shares the secrets of building a strong team and nurturing an intense sales culture at AFN. Learn about his unique "You Inc." concept that has played a critical role in shaping the company culture, promoting a spirit of entrepreneurship within the organization.Hear Ryan's take on effective leadership and risk management, his belief in the power of constructive criticism, and his insights on personal growth. Find out why he decided to sell his business and how he's exploring opportunities in the fascinating world of cannabis supply chains. But it's not all business! Ryan also shares his passion for Camp Kawaga, a boys' summer camp, and the significant impact it has on children. Whether you're a budding entrepreneur or an established professional, this episode offers valuable lessons, inspiring stories, and practical advice. Listen now for a masterclass in entrepreneurship, leadership, and beyond.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. ***

For fun, we let AI write the “Episode Description”. Enjoy:Ready to conquer the freight industry? Prepare to have your mind expanded as we journey into the realms of leadership, success, and the future of freight with Doug Waggoner, CEO of one of the largest freight brokerages in the country. A wrestling enthusiast who developed a mobile app to track wrestling matches, Doug's passion and resilience have shaped every aspect of his life, career, and meditation practice.From his early days in Kansas, through the transition to California, right up until the moment he became CEO of Echo Global Logistics, Doug's story is one of persistence and tenacity. His experiences reveal the undercurrents of his successful journey, including building a startup from the ground up, maintaining a high market cap, and transforming a public company into a private enterprise. We also delve into the pressures of answering to Wall Street and the struggles of generating enough flow for investors.But there's more! As we wind down our enlightening discourse with Doug, we explore the potential of AI in the freight market and how it could revolutionize the industry. We venture into the future, discussing the lack of barriers in the industry and the potential for consolidation among brokerages. So, buckle up, and get ready for an intense, insight-packed journey with Doug Waggoner, a man who knows every inch of the freight industry like the back of his hand.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. ***

Craig Fuller comes on the show for episode 3. We jump in with a conversation about LinkedIn versus Twitter, the role of media in our industry,  and the trust (or lack thereof) that the general public has for media in today's world. We do a deep dive into Craig's entrepreneurial journey, from his days working for his father at US Xpress, to eventually founding Freightwaves. We hit on the emotional toll of failure, and how Craig persevered through his own failures to turn Freightwaves into the company it is today. All this, and more in episode 3.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. ***