In this episode, Andrew is joined by Jesse Buckingham, CEO and cofounder of Vooma. Jesse studied law and economics at the University of Sydney and got his MBA from Stanford. Before Vooma, he was CEO at ASG LogisTech, whose businesses included Trucker Tools, Record360, e-Courier, and PackageRoute. He was also a consultant at Bain & Company.

Now, Jesse’s leading the Vooma team in building AI tools that will automate the shipment lifecycle and help brokerage teams enhance productivity and reduce opex. Vooma recently raised $13M in Series A funding led by Craft Ventures, on top of a $3.6M seed round led by Index Ventures, with support from founders and execs at companies like Motive, Project44, Ryder, and Uber Freight. 

Andrew and Jesse cover:

• How to motivate teams, lead with passion, and build trust when you’re not the founder.
• The greatest challenges around addressing and automating manual processes in logistics. 
• How AI tools like Vooma will reinvent the way brokerages run their internal operations. 
• The future of hiring for the skills required to thrive in an AI-driven environment.
• The artful balance of building an innovative, new business with having a newborn at home.

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.***

For the last episode of 2024, we welcome our first driver to the show: Chad Boblett. He created the longstanding Rate Per Mile Masters Facebook group, which, in its 11 years, has grown to be a vibrant community of close to 37,000 owner-ops, carriers, brokers, and agents. 

In this episode, we go back even further — 13 years — to how Chad got started in trucking, when a severe injury caused him to lose just about everything in his life — including his job and his house. He was living in a motel. But he still had his CDL. So with a $35,000 credit limit and a half a tank of gas, Chad bought his first truck and ran his first load. And that's how his trucking company, Boblett Brothers, was born. 

In this episode, Chad joined The Freight Pod from his house, on a lake in Lexington, Kentucky, where he talked to Andrew about:

• Building community in trucking
• What he's seeing in the truck market
• His rules of engagement with brokers
• The broker rate transparency debate
• What he thinks about freight AI
• The one thing that irks him about digital brokers

***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.***

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.***

In a special episode to announce the acquisition of Trucker Tools by DAT, we are joined by Trucker Tools CEO Kary Jablonski to break down the deal. She walks us through why now was the time for Trucker Tools to go to market, why DAT makes the most sense as the long term home for the TT platform, and what the future looks like for Kary and her team. 

This move helps further DAT's position as the premiere freight marketplace and rate analytics platform, enhancing their product pipeline and capabilities. Tune in to learn everything you need to know about the deal.

***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.***

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.***

Andrew is joined by Jonathan Salama, the CEO and co-founder of Transfix, a logistics technology company. He discusses Transfix's origins, starting as a freight brokerage business that he and his co-founder Drew built from the ground up. They focused on automating key functions like pricing, scheduling, and carrier management using machine learning models. 
When the pandemic hit, Transfix's technology proved invaluable in navigating the volatility. However, Transfix later had to pivot away from being a full-service broker when plans for a SPAC deal fell through. Salama then took over as CEO and refocused the company on its pricing automation technology, which he believes is highly differentiated and can be licensed to other brokers and shippers. 
Salama emphasizes the importance of building a strong team and doing right by people as key lessons from his 10 years in the freight industry. He remains optimistic about Transfix's future, believing the company can continue to make a positive impact by helping carriers and the broader supply chain through innovative technology solutions.

***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.***

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.***

In this captivating episode, Andrew sits down with Ryan Petersen, CEO of Flexport, for an insightful and candid conversation about leadership, personal growth, and business. Ryan shares his journey of self-discovery, discussing how he reevaluated his values after a challenging period in China and the profound impact of mentors like Tony Robbins on his life and leadership style.
The discussion delves into Flexport's operational processes challenges, including the impact of COVID-19 on their Net Promoter Score and the subsequent reorganization to improve quality and customer satisfaction. Ryan emphasizes the importance of customer obsession, highlighting Flexport's use of AI to analyze both employee and customer feedback to drive improvements. He also discusses the company's unique position in the industry, leveraging custom-built software and a worldwide network to provide innovative solutions in logistics.
Throughout the interview, Ryan offers valuable insights on balancing technology and traditional forwarding practices, the importance of attracting top talent, and the potential for AI to revolutionize the logistics industry. He shares personal reflections on leadership, and specific changes he has made to have a positive impact on his health and decision-making. The conversation concludes with a discussion of Flexport's recent acquisition of Convoy and its plans to integrate this technology to expand into new markets and improve efficiency in domestic trucking operations.

***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.***

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.***

FreightVana has acquired the brokerage operations of Loadsmith. We are joined this week for a special episode breaking down the making of the merger between these two organizations. FreightVana CEO Shannon Breen and Loadsmith CEO Brett Suma join the show to break down the deal, explaining why Loadsmith is divesting it's brokerage operations and why FreightVana is the perfect complementary partner. 

With mutual backgrounds at Knight, it was easy for Shannon and Brett to see eye to eye on how a deal like this could come together. Both organizations had a similar approach to brokerage, focusing on power only and leasing their own trailers to build an asset-like network for their shipper customers. These similarities should lead to an efficient integration opportunity.

Shannon and Brett explain the due diligence process and integration plans for the organizations, emphasizing the importance of transparency, learning from one another's teams, and making decisions in the best interests of their people and customers to ensure as much continuity as possible throughout the transition.

***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.***

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.***

The episode features an in-depth conversation with Ryan Joyce, the CEO of freight intelligence startup GenLogs. Ryan shares his unique background, having previously worked as an undercover CIA officer, a path he unknowingly would find himself on after a frightening situation with his father working in the Pentagon during 9/11. He discusses how that experience shaped his empathetic approach to problem-solving and his desire to make a positive impact. 
Ryan explains GenLogs' mission to bring unprecedented visibility and data insights to the trucking and freight industry through a nationwide network of roadside sensors. He outlines how GenLogs' technology can help recover stolen assets, provide capacity insights to brokers, and increase overall supply chain efficiency. Ryan emphasizes GenLogs' focus on responsible growth, as the organization will only be onboarding 200 customers in the next year to ensure high service levels.
Throughout the discussion, Ryan reflects on his leadership philosophy, emphasizing the importance of vulnerability and authenticity. He shares lessons learned from his time in the CIA, where he struggled with the pressures of leadership, and his desire to apply those learnings at GenLogs. Overall, the episode provides a fascinating look at Ryan's background and the unique approach he is bringing to the freight tech space with GenLogs.

***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.***

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.***

Chadd Olesen, CEO of automation technology company AVRL, joined us this week to discuss his company's journey. AVRL started in 2017 focused on natural language processing, but pivoted in 2020 to automate spot freight pricing for brokers. 
Chadd shared how AVRL had to rethink their approach and technology to better fit the needs of freight brokers, rather than trying to force brokers to adapt to their original product. He emphasized the importance of being consultative and collaborative with brokers, allowing their domain expertise to shape the automation rather than fully replacing the human element.
The conversation also touched on the evolving API pricing landscape, the challenges of change management when implementing new technology, and Chadd's personal growth as a leader in navigating the complexities of the freight industry. Overall, the episode provides insights into building a successful freight tech company by deeply understanding the industry and empowering rather than replacing human expertise.

***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.***

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.***

Uber Freight announced it's newest capacity-as-a-service offering, Broker Access. The tool is designed to provide capacity for other brokers through the Uber platform. Uber has tens of thousands of carriers within it's network through the development of it's own brokerage and the acquisition of Transplace. My concern with this program is, in my opinion, this is a case of double or co-brokering. Whichever terminology you choose to use, it represents a problem as most shippers would be very opposed to any type of arrangement where one broker is procuring capacity from another broker. 

During the episode, I break down why I believe what I do about this program, and what I think Uber should focus on moving forward to eventually reach sustainable profitability.

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.***

Kara Smith-Brown joins us on this week's episode to discuss her career in marketing, how her company, LeadCoverage supports the freight industry, and her new book, The Revenue Engine, that comes out November 19th. Together, we explore how aligning sales with marketing can lead to a harmonious and successful business environment. By sharing her journey from the early days at Echo Global Logistics, Kara illustrates the potential of modern marketing tools to create a distinct edge for businesses in a competitive landscape. Her experiences underscore the underestimated power of marketing in shaping a company’s culture and future.

Leadership and emotional resilience take center stage as we discuss the importance of maintaining composure under stress, drawing inspiration from leaders like Doug Waggoner and Scott Pruneau. Our conversation spans meditation practices, the evolving nature of leadership styles, and the unique strengths of Type A personalities. We also tackle the challenges women face in male-dominated spaces, advocating for data-backed opinions and a deep understanding of business finance to gain influence. This episode promises an insightful journey through entrepreneurship, leadership, and strategic marketing, with a dash of real-world triumphs and personal anecdotes to inspire and motivate.

***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.***

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.***