The Freight Pod

Ep. #77: Tarek Alaruri, CEO & Founder, Stuut Technologies

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 networkhttps://www.genlogs.io/

Ep. #76: Pablo Palafox, CEO & Cofounder, HappyRobot

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 networkhttps://www.genlogs.io/

Ep. #75: Chris O'Brien, President, Sunset Armada Holdings

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?

Ep. #74: Peter Coratola, President, CEO, & Founder, EASE Logistics

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.

Ep. #73: Shawn McLeod, President of Axle Logistics

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.