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.

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Thanks to our sponsors:

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

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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.

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.

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.

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.

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.