The Freight Pod

The Freight Pod is a deep dive into the journeys of the transportation and logistics industry’s brightest minds and innovators. The show is hosted by Andrew Silver, former founder and CEO of MoLo Solutions, one of the fastest-growing freight brokerages in the industry. His guests will be CEOs, founders, executives, and leaders from some of the most successful freight brokerages, trucking companies, manufacturers, and technology companies that support this great industry. Andrew will interview his guests with a focus on their life and how they got to where they are today, unlocking the key ingredients that helped them develop into the leaders they are now. He will also bring to light the fascinating stories that helped mold and shape his experiences.

The Freight Pod is a business podcast hosted by Andrew Silver, with 91 episodes on record and a Required Pod Score of 80.

Andrew Silver hosts The Freight Pod, a business show with 91 episodes published.

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  The Freight Pod

  Ep. #90: Lean Solutions Group Acquires Rapido - CEO Jack Freker and Danny Frisco

  Sep 28, 20261h 20m

  Rates spike, margins shrink, and every “simple” load turns into an exception at the worst possible time. That’s why we sat down with Danny (Rapido) and Jack (Lean Solutions Group) to get brutally practical about what actually helps freight brokers and 3PLs scale right now: a human-in-the-loop model that blends nearshore logistics outsourcing, workflow automation, and real operational governance. We dig into the real story behind Lean and Rapido joining forces, including what it takes to build operations in Mexico, why “cheapest headcount” is a dead-end strategy, and how buyers should think about geography when the goal is consistent execution. Jack also lays out how Lean is pushing past commodity staff augmentation with digital transformation support, data assessments, dashboards, and a roadmap toward outcome-based pricing and gainshare models. Then we get specific about AI in logistics. We talk through what’s working in production today (load building, quote automation, dispatch automation, appointment scheduling, document collection, POD retrieval, document verification) and why freight is a tough proving ground where the exception is the rule. Finally, we tackle the touchiest topic of all: carrier sales. Is it too “close to the wallet” to outsource, or can tech plus training create an “Iron Man suit” that scales relationships without sacrificing quality? If you care about freight brokerage operations, nearshore staffing, AI automation, and building a durable service edge, this episode is for you. Thanks to our sponsors: Cloneops.ai: Not just AI. Industry-born AI. cloneops.ai Bitfreighter : Scale Freight. Not Integration Costs. Win More. Accept More. bitfreighter.com Triumph : Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence. triumph.io/morecapacity

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  The Freight Pod

  Ep. #89: Aaron Graft, Founder and CEO, Triumph

  Aug 12, 20261h 24m

  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.ai Bitfreighter : Scale Freight. Not Integration Costs. Win More. Accept More. bitfreighter.com Triumph : Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence. triumph.io/morecapacity

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  The Freight Pod

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

  Aug 4, 20261h 49m

  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.ai Bitfreighter : Scale Freight. Not Integration Costs. Win More. Accept More. bitfreighter.com Triumph : Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence. triumph.io/morecapacity

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  The Freight Pod

  Ep. #87: Jett McCandless announces LSP44, the AI agent and infrastructure company built for logistics service providers

  Jul 14, 20261h 20m

  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.ai Bitfreighter : Scale Freight. Not Integration Costs. Win More. Accept More. bitfreighter.com Triumph : Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence. triumph.io/morecapacity

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  The Freight Pod

  Ep. #85: Ryan Soskin, Founder & CEO, GoodShip

  Jun 30, 20261h 22m

  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.ai Bitfreighter : Scale Freight. Not Integration Costs. Win More. Accept More. bitfreighter.com Triumph : Accelerate quote-to-cash with AI-powered invoicing, bank-grade carrier payments, and transaction-based market intelligence. triumph.io/morecapacity

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