What if your sales motion created real partnerships instead of fragile price wins? That’s the thread we pull with Hans, CEO of Odyssey Logistics, as he maps a journey from Danish directness and early Maersk rotations to leading a global multimodal platform through a roll-up-to-one-brand transformation. The conversation is practical, candid, and loaded with moves you can copy tomorrow—whether you’re running a desk or running a P&L.

We start with the foundation: a value proposition built on facts, not slogans. Hans explains how probing, silence, and quarterly KPI reviews expose true customer pain, unlock share of wallet, and make relationships stick at multiple levels, including the C-suite. He shares why he spends heavy time in the field, what onsite town halls surface that email never will, and how a consistent cadence—global Q&A, divisional sessions, defined values—turns culture from posters into behavior.

Then we dig into Odyssey’s shift from 16+ legacy brands to One Odyssey. Hans breaks down the integration playbook: centralizing shared services, standardizing procurement, and rebranding fast without crushing entrepreneurial spirit. He’s frank about PE carve-outs, IT risk, and why overcommunication beats overpromising during ownership changes. On growth, we get specific: three levers—share of wallet, new logos, and cross-sell—powered by a cross-trained sales force and subject matter experts. Multimodal strategy is the differentiator, with intermodal often beating truckload on cost and CO2 when planned well.

Technology underpins the whole plan. A data lake fuels route optimization, predictive analytics, and automated bidding, while better systems lift both customer outcomes and employee satisfaction. Odyssey’s rebranded brokerage in Atlanta becomes the easy entry point—truckload and LTL open the door to deeper multimodal solutions. Hans closes with career advice that never expires: choose training over titles, learn every job, stay humble, and remember the team is smarter than any one of us.

If this resonates, follow the show, share it with a colleague who sells on price, and leave a quick review so more people can find conversations that move logistics forward.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/

Cash flow is oxygen, and too many teams are holding their breath waiting on portals, proofs, and “who handles this?” handoffs. We sit down with Tarek, a former TQL broker turned founder, to unpack the culture of persistence he learned on the brokerage floor and how that same grit now powers an AI platform that doesn’t just assist accounts receivable—it does the work.

We start with the reality of freight sales: real-time chaos, creative problem solving, and an all-out push to win accounts. Then we widen the lens to founder-led growth, the kind of leadership that gets teams to feel the mission and deliver through tough cycles. From there, we go deep on AR. Why does a missing lumper fee stall a giant remittance? How do portals, short-pays, and missing documents consume weeks? Tarek breaks down a task-based system that sits on your ERP, automates the repeatable steps, and routes exceptions to the right humans in sales and CS. Think instant W‑9s, dispute drafts with proof attached, and AI-powered calls that surface the exact invoice history mid-conversation.

This isn’t AI as a buzzword. It’s time-to-value measured in days, not months, with reductions in overdue invoices and DSO you can feel in your working capital. We talk hiring A-level engineers who talk to customers and ship fast, the difference between commodity selling and value selling, and how a platform partner like A16Z adds real leverage in talent, BD, and brand. We also draw a firm line on ethics: automation belongs in B2B workflows where it creates clarity and speed, not in consumer collections that cross the line.

If you want practical tactics to close your cash gap, align finance with sales, and keep customers happy while the money moves, this conversation is for you. Subscribe, share with a teammate who’s drowning in AR follow-ups, and leave a review with the next bottleneck you want us to break down.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/

What if your operations team started each day with every check call completed and only the real exceptions waiting? We sat down with Happy Robot co-founder Pablo Palafox to unpack how an AI workforce is changing the cadence of work in freight—beyond chatbots and into end-to-end execution.

Pablo’s path runs from deep learning research and a Meta internship to YC, a hard pivot, and a clear problem: late deliveries, fines, and interns glued to phones. That pain created an opening for agents that don’t just “assist,” but actually do the work—track and trace, carrier sourcing by phone and email, POD collection, and data updates—while writing everything back into your systems. We dig into the three-layer model his team uses to scale results: execution (agents that act), data (records that get richer with each action), and intelligence (an observability layer where leaders can ask the business direct questions and get grounded answers).

We go inside the enterprise stack: why orchestration and developer-grade tooling matter, how forward-deployed engineers capture tribal knowledge and SOP nuance, and what “manage by exception” looks like for a rep when agents handle the repetitive flow. From reviving dormant LTL accounts to surfacing carriers for real loads, we talk about what to automate, what to avoid for compliance, and where human creativity stays central—especially in customer sales. Pablo shares real outcomes, including dramatic reductions in manual workload and teams redeployed to higher-leverage roles without heavy headcount cuts.

Call it minute one of a much bigger game. As operations interconnect—maintenance signaling brokerage, intelligence spotting margin leaks—agents become the connective tissue and humans become the strategists. If you’re serious about scaling service, protecting scorecards, and growing without linear hiring, this is a blueprint for turning AI from buzzword to advantage.

If this convo sparked ideas for your team, follow the show, share it with a colleague, and drop a review with the one workflow you’d hand to an agent first.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/

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?

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.

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.

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.

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.