Ep. #88: Tom Madine, CEO, ShipStation Global

Buying a bank during a meltdown sounds like a bad idea until you hear what it takes to survive it. We talk with Triumph’s CEO about growing up in small-town Oklahoma, sprinting through Big Law, and then walking away from the safe path with a young family and almost no margin for error. What follows is a candid story of mentorship, risk, and the kind of pressure most founders only admit to after they’ve made it through. From there, we trace how Triumph goes from distressed-debt ambition to becoming a serious force in transportation finance: transportation factoring for carriers, broker payments and supply chain finance, and now logistics intelligence built on an asset most freight tech can’t match, paid invoice data. We dig into why brokers often misunderstand “controlling payments,” how factoring changes the carrier relationship, and what it really takes to sell enterprise payments in a trust-heavy industry. If you care about freight brokerage strategy, carrier liquidity, working capital, or building durable logistics platforms, this one is packed with practical framing. We also hit the uncomfortable realities shaping the market: fraud attempts that target remittance changes, why payments are treated as financial crime, and how post-Montgomery liability breaks the risk-reward math for brokers and demands clearer rules. We close with leadership lessons that apply well beyond trucking: trade-offs, focus, and surrounding yourself with people who love you enough to tell you the truth. Subscribe, share this with a friend in freight, and leave a review with the biggest takeaway you’re applying next.Thanks to our sponsors:Cloneops.ai: Not just AI. Industry-born AI.cloneops.aiBitfreighter: Scale Freight. Not Integration Costs. Win More. Accept More.bitfreighter.comTriumph: Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence.triumph.io/morecapacity

From a live, in-person Chicago studio, we sit down with Tom Madine to unpack what real scale looks like in transportation, and why SMB shipping is still one of the most misunderstood corners of logistics. Tom shares his path from early sales roles into building Worldwide Express, then zooms out to the hard truth: small and midsize shippers don’t just buy rates. They buy accountability, fast fixes, and a partner who can “make it right” when the inevitable problems hit.We go deep on business models that divide founders and operators: direct sales vs franchise networks vs agent programs. Tom breaks down the trade-offs of control, the power of entrepreneurial motivation, and why culture and management matter more than the org chart. Then we shift into mergers and acquisitions strategy, including the mistakes that kill deals (like rushing rebrands) and the playbook that helps integrations stick: align on a common vision, align economically, communicate relentlessly, and move fast on the painful synergy work so it doesn’t drag on.Finally, Tom explains the big bet behind ShipStation Global and the Auctane combination: pairing logistics software and e-commerce shipping tools with deep carrier relationships and a massive commercial engine, aiming for a true single pane of glass across parcel, LTL, and beyond. If you care about freight brokerage, logistics technology, private equity partnerships, and building a durable platform in a fragmented market, this one is for you. Subscribe, share with a builder in your network, and leave a review: what’s the hardest part of scaling a logistics business without losing what made it great?Thanks to our sponsors:Cloneops.ai: Not just AI. Industry-born AI.cloneops.aiBitfreighter: Scale Freight. Not Integration Costs. Win More. Accept More.bitfreighter.comTriumph: Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence.triumph.io/morecapacity

The freight market changes fast, but a lot of broker operations still look the same: endless check calls, status emails, manual appointment scheduling, missing PODs, and a nonstop flood of “where’s my order” messages. We sat down live with Jett McCandless, founder and CEO of Project44, to make a major announcement and dig into the why behind it: LSP44 is launching as a dedicated business built specifically for logistics service providers, including 3PLs, freight brokers, and freight forwarders. We talk through the history that led here, from Project44’s early LSP roots to the hard lessons of selling into shippers with entrenched EDI teams and slow enterprise change management. Jett shares what changed when capital stopped being “free,” how prioritization decisions damaged LSP relationships, and how product reliability helped drive a dramatic NPS turnaround. The big takeaway: LSPs buy and use technology differently because their product is the service, and they need infrastructure that plugs into their operating system and scales without adding overhead. Then we get tactical on logistics AI. Where do AI agents belong in the workflow, and where are they just an expensive band-aid? Jett breaks down the API-first approach, the gaps agents should fill, and the orchestration layer that constantly tests vendors, routes tasks to the best performer, and delivers outcomes without forcing customers to manage a fragmented tech stack. We also dig into trust, data rights, and why “cool demos” are getting replaced by brutal ROI questions across the industry. If you care about freight visibility, AI automation, TMS strategy, and what the next decade looks like for domestic brokers versus global forwarders, this one goes deep. Subscribe, share with a broker operator who’s tired of vendor sprawl, and leave a review with the one freight task you’d automate first.Thanks to our sponsors:Cloneops.ai: Not just AI. Industry-born AI.cloneops.aiBitfreighter: Scale Freight. Not Integration Costs. Win More. Accept More.bitfreighter.comTriumph: Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence.triumph.io/morecapacity

Rates are spiking and the scary part is why. We kick off with a June truckload market update built on real broker payment data, then we zoom in on what the numbers are actually saying: van, reefer, and flatbed buy rates are surging year over year, but freight demand is not the headline. Capacity is. Enforcement pressure, compliance friction, and a permanently higher cost floor are squeezing the supply side, and that changes how you price, how you source trucks, and how you talk to customers.Liz Wayne, CEO of Able Transport Solutions, joins me for a grounded look at flatbed and heavy haul logistics. We talk about why open-deck freight is harder to execute, how rare equipment like multi-axle RGNs can turn a single mistake into a massive TONU, and why proactive communication is the real “margin protection” strategy. We also get honest about the truck in hand myth, what shippers should actually expect from a broker, and the mindset of never giving loads back.We go beyond ops into leadership and strategy: staying focused as a founder, building systems that prevent half-finished initiatives, and learning to delegate without losing standards. We also dig into the Supreme Court negligent hiring landscape and what it means for carrier vetting, shipper contracts, indemnity clauses, and risk. Finally, we hit AI in logistics, back-office automation, and why data center construction may be a quiet demand engine for flatbed freight.Subscribe for more real freight operator conversations, share this with a teammate, and leave a review with the one guest or industry challenge you want us to break down next.Follow The Freight Pod and host Andrew Silver on LinkedIn.Thanks to our sponsors:Cloneops.ai: Not just AI. Industry-born AI.cloneops.aiBitfreighter: Scale Freight. Not Integration Costs. Win More. Accept More.bitfreighter.comTriumph: Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence.triumph.io/morecapacity

Freight procurement is still stuck in a world of portals, spreadsheets, and three-month RFP cycles, even though the freight market can flip in weeks. I’m joined by Ryan Soskin, CEO and founder of GoodShip, to unpack why that gap creates expensive surprises for shippers and impossible commitments for brokers and carriers. Ryan’s career arc from Coyote Logistics to Convoy gives him a rare view of both execution on the ground and what it takes to build automation that actually works at scale. We get specific about what breaks contract freight pricing: most bids share only origin, destination, volume, and equipment type, while real truckload economics depend on lead time, seasonality, days of week, facility hours, and constraints that never make it into the RFP. That missing context fuels winner’s curse, fragile routing guides, tender rejection spikes, and more spot market exposure. From there, we connect procurement to performance management and the need for a shared source of truth, so QBRs stop turning into arguments about on-time definitions and start turning into decisions. Ryan also introduces the idea of network drift: even a “perfect” annual routing guide drifts away from optimal as rates, volumes, and carrier performance change. GoodShip positions itself as a TMS-agnostic system of action that unifies transportation data and recommends corrective moves, including mini-bids and routing guide adjustments. We close with Laney, GoodShip’s AI transportation analyst, and where proactive, always-on logistics analytics can take freight network optimization next. If you found this useful, subscribe, share it with a transportation leader on your team, and leave a review with the biggest freight procurement pain you want fixed next.Follow The Freight Pod and host Andrew Silver on LinkedIn.Thanks to our sponsors:Cloneops.ai: Not just AI. Industry-born AI.cloneops.aiBitfreighter: Scale Freight. Not Integration Costs. Win More. Accept More.bitfreighter.comTriumph: Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence.triumph.io/morecapacity

“AI can negotiate freight rates” is one of those claims that sounds true until you sit on a real brokerage floor and watch what happens. I’m joined by Robby Nathan, founder of Load Delivered, CEO of Envoy AI, and a longtime freight operator, to break down what separates automation that actually helps from automation that just fires off templated emails and calls it intelligence. We start with the roots: how Robbie went from a philosophy degree to the carrier desk, why he chose temperature-controlled, high-value freight in the 2008 downturn, and what hyper specialization teaches you about SOPs, service, and building a carrier network that can handle high expectations. From there we get into the hard parts of scaling a freight brokerage: capital constraints, enterprise shippers that cap your volume, EDI setup delays, and the leadership shift that hits when the company outgrows your personal operating style. We also tackle the new risk reality after the Supreme Court negligent hiring environment, why inconsistent processes across pods or agents can create major liability, and why carrier vetting and documentation are becoming non-negotiable for brokers and 3PLs who want to stay in business. Then we go deep on logistics AI, adaptive rate negotiation, and the semantic layer needed to move from copilot to safe autopilot. Robby shares what he’s building with Envoy around carrier communication, verification filters, and a future where freight operators manage AI workers instead of living on the phone all day. If you care about freight tech, carrier compliance, TMS data quality, and the future of brokerage, this one will challenge how you think about “automation.” Subscribe, share with a teammate, and leave a review. What part of brokerage should never be manual again?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/

A major freight market intelligence leader is leaving DAT for a brokerage and he’s explaining exactly why. Ken Adamo joins me and Peter Coratola to talk about what most people misunderstand about DAT, how brokers should actually use spot market data, and why the best teams treat analytics as decision support rather than a single “rate truth.” If you’ve ever argued over Rateview screenshots, struggled to explain pricing to a shipper, or wondered why fancy tools don’t get adopted, this one will hit home.We also break news: Ken is joining Ease Logistics as Chief Strategy Officer. We unpack what that role looks like inside a modern, tech-forward brokerage, from product and pricing science to tech adoption and strategic bets. Along the way we debate the seductive idea of drop trailers and why trailer pools can turn into a margin-killing operational tax if you don’t have the systems, discipline, and accountability to manage them.Then we go straight into the market: Winter Storm Fern, RFP behavior, and the mistakes that cost incumbents freight when they panic, give volume back, or “quote cowardly.” Ken shares a grounded outlook on contract rates, the capacity flush, and why 2026 is the table-setting year that can create a huge 2027 for brokers who stay disciplined on pricing, operations, and portfolio thinking (yes, including the reality that some loads go negative).If you like honest freight broker talk with practical strategy, subscribe, share this with a teammate, and leave a review so more operators can find it.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/

Freight buying has a dirty secret: most bids do a great job of finding the lowest number and a terrible job of finding the best outcome. When shippers reward price without measuring service, good carriers get punished, bad actors slip through, and procurement teams spend weeks in spreadsheets trying to guess what suppliers actually want.We sit down with Alan Holland from Keelvar to break down a better approach using sourcing optimization, mechanism design, and AI agents. Alan explains how incentive compatible auctions can pull truthful preferences to the surface, why package bids and conditional discounts create space for small fleets to win the lanes they can run best, and how the Google Ads auction is a surprisingly useful model for modern freight procurement. From there we get practical: connecting transportation management system performance data to the sourcing event, weighting on-time performance with price, and designing feedback loops that reward reliable execution instead of “cheap and shaky” promises.We also zoom out to the bigger AI shift. Massive compute, LLMs, and code generation tools like Claude Code are changing how software gets built, which means logistics technology will evolve faster than most teams are ready for. We talk about risk, uncertainty, penalty cliffs, rebate targets, and the long-term “holy grail” of multi-shipper combinatorial exchanges that could unlock network-level efficiency.If you care about freight procurement strategy, logistics automation, AI in supply chain, or the future of brokers and carriers, hit play. Subscribe, share this with a friend in logistics, and leave a review with your biggest question about where AI agents help most.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/

Freight is a physical business, but the decisions that make or break a carrier feel more digital every month. I sit down with Chris Ceausu, CEO of White Arrow, to unpack what it really takes to run a complex transportation network across intermodal reefer containers, cross-dock facilities, volume LTL consolidation, and a supporting freight brokerage. If you’ve ever wondered why two carriers can run “the same lane” and get totally different results, this conversation makes it painfully clear: cost allocation, process design, and execution are the whole game.We get into the hard stuff operators don’t love to say out loud: how margin compression forces brutal pricing choices, why asset utilization can matter more than almost any overhead cut, and why trying to “predict the market” often feels like trusting a Ouija board. Chris shares how he evaluates signals like the CASS Freight Index and utilization data, why he’s working to reduce exposure to the most cyclical truckload segments, and how a network with multiple touchpoints creates both service advantages and operational risk.Then we get into AI in logistics, not as a buzzword, but as a tool that can ingest real operational data, summarize call drivers, and speed up building internal workflows. Chris explains his “own the core, plug in the rest” tech strategy, why security is a serious concern when you connect AI to sensitive systems, and why execution is the only thing that ultimately matters. If you lead in trucking, brokerage, supply chain, or transportation procurement, you’ll leave with practical ideas on tech, pricing, and building teams that can adapt fast.Subscribe for more operator-first conversations, share this with a friend in freight, and leave a review if it helps.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/

A 10‑day wait for a refrigerator became the spark for a smarter last mile. We sit down with OneRail CEO Bill Catania to unpack how a racing mindset—frugality, failure tolerance, and relentless iteration—translated into a platform that helps retailers move from static delivery workflows to real‑time orchestration at scale. Bill shares the throughline across three startups: aggregate fragmented supply, connect it cleanly to demand, and let data science make the hard choices in milliseconds.You’ll hear how RaceFan aggregated 650 local tracks to unlock national sponsorships, why MDOT’s 200‑millisecond cloud coupon switch won over skeptical retailers (and how Bill timed the sale), and the moment OneRail shifted from gig moving to an enterprise platform. We break down OneRail’s three‑layer model—software first, an aggregated carrier network across sedans to flatbeds, and a human exception team—and how the company takes on risk under its authority to deliver accountability most intermediaries avoid.AI is not a bolt‑on here. Bill explains how courier “credit scores,” market‑level performance, and dynamic assignment replaced manual dispatch, enabling one person to triage roughly 4,000 orders instead of 80. We explore exceptions in furniture and cold chain, SKU‑level loss analysis, and how pushing intelligence upstream into order management can reshape cost to serve before a truck even moves. Along the way, Bill shares the “yes if” leadership mantra that keeps doors open while aligning risk and reward—fuel for winning enterprise trust and recognition like Lowe’s Innovation Partner of the Year.If you care about last mile logistics, enterprise retail, or building resilient platforms, this conversation is a blueprint: aggregate wisely, decide precisely, own outcomes, and scale through partnerships. Subscribe, share with a teammate who obsesses over SLAs, and leave a review with your biggest “yes if” moment—we’ll feature the best on a future show.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/