The Freight Show

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The Freight Show brings stories of freight and logistics leaders who’ve shaped the industry. Through in-depth conversations, we explore their journeys, the challenges they’ve overcome, and the insights that have driven their success. Each episode uncovers the lessons, strategies, and wisdom of these freight leaders.

  1. MAR 20

    Jonathan Drouin (WWEX) on Build-vs-Buy for AI in Freight

    Most freight brokerages are drowning in AI pilots that never make it to production. The gap between a working demo and a system processing thousands of loads per week is not technical — it is organizational. It comes down to setting clear KPIs up front, running biweekly AI steering committees with full leadership visibility, and being ruthlessly honest about what is working and what is not. Jonathan Drouin has lived both sides of this equation. He started as a software developer at 19, moved his first freight load in 2012 at Bear Transportation under Michael Kaney, built and sold his own TMS company and brokerage, then joined WWEX (formerly Worldwide Express) in 2019 to lead truckload technology. Over seven years, he has helped scale the company from $2B to $5B through the GlobalTranz merger and 35+ acquisitions — migrating systems, integrating business units, and now spearheading AI deployment across the entire quote-to-cash workflow. Today, he oversees product strategy and AI initiatives for a company where freight mix is roughly 40% LTL, with the rest split between parcel and truckload, serving primarily SMB and mid-market shippers as the largest UPS reseller in North America. In this conversation, Jonathan breaks down the exact framework WWEX uses to deploy AI: how they mapped every workflow from quoting to cash, prioritized initiatives against three hard metrics — customer retention, margin growth, and cost reduction — launched a dozen AI projects in year one to stress-test the boundaries, and now run every initiative through a rigorous steering committee with predefined KPIs and public accountability. He explains why email AI and repetitive tasks deliver the fastest ROI, why they shifted from build-first to partner-first as model complexity increased, the change-management discipline that separates successful deployments from expensive experiments, and why he believes AI will chip away at exception handling far beyond today’s repetitive-task automation. What you’ll learn The three-pillar AI prioritization framework: How WWEX evaluates every AI initiative against customer retention, margin growth, and cost reduction — and why vague goals like “quality of life improvements” do not make the cut in a private-equity-backed, results-driven culture.Why email AI wins first: The specific reasons email-based automation like quoting and carrier communication delivers faster ROI than other channels — customers do not know AI is involved, responses are faster, and workflows are linear enough for today’s models to handle exception management effectively.From 60 ideas to 12 deployments: The exact process WWEX used to map workflows role by role and team by team, stress-test assumptions with business leaders educated on AI capabilities, and narrow down to initiatives with clear, measurable outcomes tied to business KPIs.Build vs. partner: the 2025 inflection point: Why Jonathan went from bullish on internal builds to heavily favoring vendor partnerships — hyper-funded vendors with MIT and Carnegie Mellon talent can deploy 5–7 engineers on your use case, technology is moving too fast to bring costs in-house, and partnering enables more experimentation at lower risk.The AI steering committee model: How running biweekly reviews with top leadership and all business stakeholders — where every project’s KPIs are public and visible from day one — creates accountability, forces intellectual honesty, and separates projects that deliver from expensive learning experiences.Prototype to production: the 5% to 50% problem: Why getting a functional AI demo working on 1% of use cases takes almost no time, but scaling to 50% production reliability is a months-long journey — and why most people underestimate this gap until they have shipped something real.Repetitive tasks today, exception handling tomorrow: Jonathan’s contrarian view that AI will move upstream faster than people think — today it handles repetitive work, but as models gain more context from email history, phone transcripts, and CRM data, they will chip away at exceptions that require a person today, like invoice mismatches or missing PO numbers.Change management as the real bottleneck: Why the biggest barrier to AI ROI is not the technology — it is cultural buy-in, setting clear outcomes up front, and having the organizational discipline to push through resistance when the destination is clear and the product works.Why PepsiCo and other shippers built internal brokerages: The logic behind turning transportation spend into a profit center, why these initiatives often plateau after aggressive early growth, and how market downturns expose the same cash-flow and margin challenges traditional brokers face.The non-optional AI moment for every company: Why Jonathan believes companies resisting AI adoption risk becoming the next Kodak, why “quality of life” improvements do not cut it anymore, and how WWEX’s M&A-hardened culture of rallying around big decisions enables faster, more disciplined change management than most peers.Time-stamped highlights (00:00) From French-Canadian immigrant to software developer at 19: How Jonathan’s dad put IT books in his hands and sent him to a customer site, leading to a non-linear path from clinical software to freight brokerage at Bear Transportation under Michael Kaney in 2012.(03:30) Early career arc: CH Robinson via Phoenix acquisition, PepsiCo’s internal brokerage, then raising venture capital to build his own TMS company and freight brokerage in 2016–2017 — using his own software to prove the efficiency thesis.(06:45) Why PepsiCo started a freight brokerage: The executive-level logic of turning billions in transportation spend from cost center to profit center, leveraging massive private fleets and backhaul opportunities, and the typical growth-then-plateau trajectory of shipper-owned brokerages.(09:30) The shipper-brokerage plateau pattern: Why these initiatives often stall after hitting a certain scale — the same market disadvantages as traditional brokers, cash-flow challenges when you are in the business of making product, and waning executive excitement as the model matures.(12:00) Building vs. buying a TMS: Jonathan’s journey from building his own TMS to now making billion-dollar TMS decisions at WWEX — why stability and people/process alignment matter more than cutting-edge tech, and when building makes sense.(15:30) WWEX structure and strategy: How the $5B company operates across three go-to-market brands — Worldwide Express, GlobalTranz, and Unishippers — splits roughly 40% LTL and 60% parcel/truckload, and serves SMB and mid-market as the largest UPS reseller in North America.(18:00) Multi-mode sales structure: Why WWEX splits LTL/parcel reps from truckload reps — sales behavior naturally gravitates toward what reps are successful at, so specialization by mode drives better outcomes than training one rep on everything.(20:45) Jonathan’s evolving role at WWEX: From truckload platform buildout in 2019, through GlobalTranz integration and multiple migrations, to revenue operations and AP work with LTL carriers, then shifting to AI strategy in 2024 and now overseeing product strategy with heavy focus on the agent channel.(24:00) Mapping the AI opportunity: How WWEX went role by role, team by team, workflow by workflow to map the entire q...

    56 min

  2. MAR 3

    Terminal Industries CPO Chris Brumett on the Hidden Cost of Yard Congestion

    Freight doesn’t slow down at the dock. It slows down in the yard, at the gate, and in the messy handoff between facility ops and transportation. Chris has spent decades inside that “supply chain execution” layer, and he’s now building a modern yard operating system at Terminal Industries to remove the friction most networks have learned to tolerate. In this episode, Chris Brumett, Chief Product Officer at Terminal Industries, breaks down how warehouses actually optimize (labor travel time, staging space, dock throughput), why carrier appointment compliance is a facility survival mechanism, and how low-visibility yard operations quietly create expensive downstream inefficiency. We also dig into the technology shift powering the category, from ASNs and appointment scheduling to computer vision and AI-driven workflows that reduce gate congestion, improve trailer/chassis visibility, and tighten execution across the full facility visit. What you’ll learn Dock-Driven Warehouse Optimization: How product velocity, storage zones (ambient vs. temp-controlled), and travel time dictate door assignments and labor planning.ASN Visibility and Receiving Automation: Why ASNs matter, how they connect to scanning and inventory accuracy, and where “ideal state” still breaks down.Tendered vs. Operating Carrier Validation: How load brokering creates identity ambiguity at the gate and why facilities need separation between tendered carrier, operating carrier, and cargo asset.Appointment Windows as Labor Control: The real reason strict appointment rules exist, how staging creates dock congestion, and why facilities penalize missed windows.Inbound Priority Logic From Outbound Demand: How facilities prioritize inbound based on outbound shortages, retail promotions, and SKU velocity, not “fairness” to carriers.Drop Trailer Strategy and Yard Buffering: Why drop-and-hook creates slack that smooths operational variance, and when yard footprint becomes the constraint.The Hidden ROI of Yard Execution: Why optimizing “five spotters” misses the point, and how yard inefficiency causes dock labor idle time and throughput loss.From Point Tools to Yard Operating System: How Terminal approaches the yard as an end-to-end workflow problem, not a check-in camera or a spreadsheet replacement.Computer Vision and AI Workflow Automation: Where CV reduces gate processing time, and how AI can automate repetitive operational steps without removing the human-in-the-loop.Facility ROI Levers That Actually Pencil: Labor displacement/reallocation, detention and demurrage reduction, and scaling volume without scaling labor.Time-stamped highlights (01:40) Warehouse Operations and What Facilities Optimize For(04:44) How Warehouses Actually Optimize Labor and Inventory(08:05) Warehouse Management Systems and Labor Efficiency(10:17) Advanced Shipping Notices, EDI, and Inbound Visibility(12:21) Carrier Visibility Gaps and Multi-Broker Complexity(15:08) Appointment Scheduling and Labor Planning Mechanics(17:28) Why Appointment Compliance Drives Facility Efficiency(22:11) Staging Loads and Dock Congestion Tradeoffs(23:32) Freight Prioritization Based on Product Urgency(27:00) Retail Promotions and Inbound Acceleration(29:49) Facility Optimization vs. Shipper-of-Choice Tradeoffs(35:17) The Yard as the Forgotten Operational Lever(40:28) Spotter Inefficiencies and “Asteroid Hunt” Yard Problems(44:42) Terminal’s Yard Operating System Approach(51:11) Customer ROI, Labor Savings, and Throughput GainsGuest Chris Brumett — Chief Product Officer, Terminal IndustriesChris Brumett is the Chief Product Officer at Terminal Industries and a longtime supply chain execution operator focused on warehouse and yard technology. He has spent roughly 30 years building software that improves operational execution, with the last 15 years centered on yard management and the systems that connect facilities, assets, and transportation providers.LinkedIn: https://www.linkedin.com/in/chris-brumett-6a04201/ Links & references Terminal Industries (Company): https://terminal-industries.comChris Brumett Profile (Terminal / org directory): https://theorg.com/org/terminal-industries/org-chart/chris-brumettANSI X12 856 (Advance Ship Notice / Ship Notice): https://www.stedi.com/edi/x12/transaction-set/856GS1 Overview of ASN (Advance Ship Notice) Standards: https://www.gs1.org/standards/ediCouncil of Supply Chain Management Professionals (CSCMP) — Supply Chain Resources: https://cscmp.org Brought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    56 min

  3. FEB 24

    Price Rite Transport President Will Kerr on How Carrier Density Drove a $10M First Year

    The freight market looks very different depending on which side of the phone you sit on. Will Kerr has lived both sides deeply, first as a carrier sales operator and brokerage founder who scaled Edge Logistics to $10M in its first year and over $160M in revenue, then as a trucking executive navigating today’s broker-driven freight environment. His perspective cuts through a lot of surface-level advice by unpacking the mechanics that actually determine who gets freight covered, who absorbs risk, and where margin is really made. In this episode, William Kerr, President at Price Rite Transport and Founder and former CEO of Edge Logistics, breaks down how Edge scaled by building carrier density instead of chasing volume, what separates high-performing carrier reps from the rest, and how internal brokerage dynamics quietly decide which loads get covered and which go negative. We also dig into capacity realization risk, why “autobook” freight is the real profit center inside large brokerages, how carrier tagging and internal trust are earned, and why a disciplined, broker-centric carrier strategy can outperform direct shipper relationships in the current pricing, compliance, and payment environment. What you’ll learn Carrier Density as a Productivity Engine: Why top carrier reps drive volume through a small bench of relationship carriers to reduce rate thrash and increase repeatability.The 50–500 Truck Sweet Spot: How mid-size fleets unlock lane-level consistency, and why those carriers are the hardest to win and retain.Carrier Ownership and Tagging Mechanics: How “exclusive use” works inside big brokerages, including minimum booking thresholds and time-based earning rules.Internal Deal Selling in Split Models: Why carrier reps sell deals internally to customer reps and managers, and how that determines who gets the freight.Minimum Fees and Loss Allocation: How carrier-side minimums are structured and why losses typically roll to the customer side when markets turn.Capacity Realization as a Hidden Risk Lever: How booking two weeks out can turn into same-day chaos when carriers shop loads and fall off late.Why Loads Go Negative Fast: How day-of repricing at 30–100% higher rates can flip a marginal load into a multi-hundred-dollar loss.Autobook Freight and Tribal Knowledge: How the best reps pre-position capacity and become the default option when “easy money” freight hits the board.Carrier Compliance in the Digital Era: Why digital footprint scoring and broker-centric reporting systems can block legitimate carriers from freight flow.Carrier Consolidation as a Reset Button: The operational steps behind merging six carriers into one brand—dispatch, safety, systems, fleet branding, and go-to-market.Time-stamped highlights (01:20) From CME Trading Floors to Truckload Freight(03:10) Learning Carrier Sales Inside Echo Logistics(05:30) Commission Changes and Talent Flight(07:30) Launching Edge From a Trailer(09:30) Scaling a Carrier-First Brokerage Model(12:00) What Made Great Carrier Reps Win(14:10) The 50–500 Truck Carrier Sweet Spot(17:10) How Carriers Get Locked and Tagged(19:10) Losses, Minimum Fees, and Split Models(22:00) The Myth of “No Trucks”(24:30) Becoming a Broker of Choice for Carriers(27:20) Tribal Knowledge and Auto-Book Freight(30:10) Capacity Realization Failures(35:10) Carrier Compliance in a Digital Vetting Era(41:30) Consolidating Fleets Into One BrandGuest William Kerr — President, Price Rite TransportWilliam Kerr is President of Price Rite Transport and Founder and former CEO of Edge Logistics, where he built a carrier-first brokerage that scaled to enterprise volume. He brings a rare operator’s view of both brokerage carrier sales and trucking network strategy.LinkedIn: https://www.linkedin.com/in/william-kerr-92275363/ Links & references Price Rite Transport: https://www.priceritetransport.com/Edge Logistics: https://www.edgelogistics.com/Echo Global Logistics: https://www.echo.com/Traffic Tech: https://www.traffictech.com/Highway: https://www.highway.com/Brought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    50 min

  4. FEB 5

    Reliance Partners President Chad Eichelberger on Freight Risk Economics and Scaling to $675M

    Freight companies that scale well usually share one thing in common: they obsess over the operating details that keep the business from breaking as headcount, customers, and complexity explode. Reliance Partners President Chad Eichelberger has built his career inside that reality, from early-stage brokerage growth to enterprise-scale execution and risk management. In this episode, Chad walks through two rare zero-to-scale runs—helping grow Access America from an early-stage Chattanooga startup into a brokerage that reached a $675M run rate before selling to Coyote, then applying the same scalability discipline to build Reliance Partners into a specialist insurance platform for trucking and logistics. We unpack the metrics and cultural rules that made the brokerage model work at scale, plus the new risk reality for brokers today—where strategic cargo theft and fraud are reshaping underwriting, controls, and the true cost to serve. What you’ll learn How to design brokerage growth that scales (not just grows): The input metrics Access America measured (talk time, calls, pipeline hygiene) and why “small” behaviors become massive leading indicators.How to build a competitive sales culture without breaking teamwork: The CRM rules, account ownership enforcement, and RFP adjudication process that kept teams aggressive and aligned.Why cradle-to-grave worked—and where hybrid structures emerged: How large enterprise accounts naturally evolved into regionalized “enterprise pods” while keeping accountability tight.What elite cold calling really looked like: Gatekeeper navigation, dial-by-name tactics, and the persistence that turns “years of voicemails” into a top customer.What a “never say no” service mindset costs—and why it pays: The $32K charter-plane shipment loss that reinforced execution as a brand advantage.How insurance scales differently than brokerage sales: Why insurance is often “win it all or win nothing,” and how renewals create an annuity-like book when service stays tight.How broker risk has shifted from catastrophic liability to high-frequency cargo losses: Why strategic theft and fraud are forcing new controls—and raising the cost of coverage.What underwriters actually evaluate: Vetting stack, loss history, commodities, contracts, compliance maturity, and why the pool of active underwriters is tighter than most brokers assume.How to reduce theft exposure: Repeat-carrier discipline, high-value protocols, anomaly detection signals, and why “one exception” often becomes the breach.Why 2026 feels different: The optimism case for a healthier market—if the macro picture doesn’t break.Time-stamped highlights (01:05) Early Access America Origins(02:40) Entering Brokerage as a Young Seller(03:33) Rising Through the Ranks(05:25) What Actually Scales a Brokerage(06:19) Metrics, Measurement, and Process Discipline(08:24) Competitive Culture at Access America(10:12) Sales Training and Battle-Tested Reps(11:16) Cold Calling That Works(16:01) Competition Without Breaking Teamwork(18:08) CRM Discipline and Account Ownership(20:05) Cradle-to-Grave vs. Chicago Model(25:29) Transitioning Through the Coyote Merger(27:05) Building Reliance Partners(32:00) Why Transportation Insurance Is Fragmented(42:35) Rising Risk and Changing Insurance RequirementsGuest Chad Eichelberger — President, Reliance PartnersChad Eichelberger is President of Reliance Partners, the largest standalone insurance agency dedicated exclusively to the transportation and logistics industry, insuring more trucking fleets in the U.S. than any other agency. Previously, he served as President of Access America Transport through its merger with Coyote Logistics, bringing deep experience in scaling freight brokerages, building high-performance sales organizations, and managing risk at enterprise scale. LinkedIn: https://www.linkedin.com/in/chadeichelberger/ Links & references Reliance Partners: https://reliancepartners.com/Access America Transport + Coyote deal coverage (growth + transaction context): https://www.chattanoogan.com/2014/11/17/288154/Coyote-Logistics-Merging-With.aspxUPS acquisition of Coyote Logistics: https://www.ups.com/assets/resources/media/en_US/20150812_UPS_Coyote_Deal_Deck.pdfC.H. Robinson Worldwide, Inc. v. Miller (No. 20-1425): https://www.supremecourt.gov/docket/docketfiles/html/public/20-1425.htmlBrought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    54 min

  5. JAN 20

    Enterprise Shipper Paul Estrada on Designing a Low-Cost-to-Serve Freight Network

    If you sell into enterprise shippers, here’s the uncomfortable truth: your differentiator isn’t your pitch deck, your coverage story, or even your rate. It’s whether you can deliver predictable service and predictable economics inside a network built to eliminate volatility. This episode pulls back the curtain on how a large enterprise shipper actually runs transportation procurement. Paul Estrada has spent nearly two decades leading procurement at scale, and he breaks down what most providers miss: the internal “cost vs. service” tug-of-war, why procurement lives on a scoreboard, how routing guides stay intact when markets swing, and what it really means to be a low-cost-to-serve partner. We get into radical data transparency, carrier enablement, index-based pricing, and why the best providers don’t just quote lanes—they explain the math behind sustainable pricing. What you’ll learn How enterprise supply chains are actually organized: Why procurement, operations, manufacturing, and customer teams optimize for different goals—and how those tensions are managed.The two metrics that matter more than all others: Getting product where it’s needed, when it’s needed, at the lowest sustainable cost.Why procurement lives on a scoreboard: How performance is measured in dollars and cents—and why market cycles can make teams look like heroes or villains overnight.How enterprise shippers manage cost volatility: Dedicated capacity, portfolio mix, and risk mitigation as insurance—not ideology.Why carrier-agnostic procurement wins: How decisions are made across brokers, asset carriers, and dedicated fleets based on utilization and economics—not labels.What shippers actually look for in brokers: Sustainable pricing, operational intelligence, and the ability to explain how rates work—not just what they are.Why deep data sharing creates better pricing: How transparency around volumes, seasonality, and operating constraints leads to routing guides that hold up.How carriers are onboarded like employees: SOPs, portals, escalation paths, and training as a way to reduce churn and execution risk.The “Goldilocks” provider strategy: Why fewer, deeper relationships outperform wide, fragmented networks over time.How AI matters to shippers (and how it doesn’t): Why buzzwords don’t win business—but lower transaction costs do.Time-stamped highlights (00:00) Paul Estrada and the Enterprise Shipper Lens(01:12) Breaking into Supply Chain and Procurement(02:42) Inside a Large Enterprise Logistics Organization(05:19) The Two KPIs That Everything Rolls Up To(06:40) Cost vs. Service and Internal Tension(08:52) The Operations Team as the Balancing Layer(10:16) Promotions, Firings, and the Procurement Scoreboard(12:27) Managing Risk and Volatility Across Cycles(14:46) Service Performance and Failure Points(16:31) Data Infrastructure and Fast Decision-Making(18:19) Optimization as a Cultural Advantage(20:45) Portfolio Thinking Across Carriers and Brokers(22:51) Brokers in Contractual Freight(24:18) Evaluating Provider Sustainability and Risk(25:54) Radical Data Sharing and Pricing Stability(30:08) Building a High-Quality Carrier Bench(33:47) What Separates Long-Term A-Player Providers(37:04) Becoming a True Shipper of Choice(40:21) Reading the Market and Rate Cycles(43:48) Index-Based Pricing and Trust-Based PartnershipsGuest Paul Estrada — Director of Procurement, Niagara BottlingPaul Estrada has spent nearly 20 years in transportation and supply chain leadership, with deep experience across operations and procurement at enterprise scale. He leads procurement strategy focused on cost optimization, service reliability, risk management, and long-term carrier partnerships—bringing a data-driven, relationship-oriented approach to one of the most complex logistics networks in the industry. LinkedIn: https://www.linkedin.com/in/paulmestrada/ Links & references Niagara Bottling: One of the largest beverage manufacturers in the U.S. with a highly optimized supply chain — https://www.niagarawater.com/Dedicated vs. One-Way vs. Brokered Freight Models: Portfolio approaches to capacity and risk managementIndex-Based Freight Pricing: Contract structures tied to market indicesBrought to you by Vooma - Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    55 min

  6. JAN 14

    Evans CEO Ryan Keepman on Becoming a “3.5PL” and Scaling From $80M to $400M

    The freight market has trained most brokerages to chase volume, compete on price, and treat service lines like shiny add-ons. Evans Transportation took the opposite approach: build a durable business by leaning into complexity, building culture as a competitive advantage, and diversifying with discipline. In this episode, Ryan Keepman shares how Evans — one of the rare family-owned brokerages still standing from the deregulation era — evolved from a Wisconsin brokerage built on relationships into a multi-division logistics operator supporting everything from envelopes to excavators. We unpack the real mechanics behind service-line expansion, why the “jack of all trades” strategy kills trust, and how Evans uses intentional culture and in-person connection to keep remote teams aligned as the company scales. What you’ll learn How Evans Transportation survived deregulation and stayed family-owned: Why relationship-driven brokerage and early operational investments helped Evans outlast consolidation.The real reason Evans diversified into multiple divisions: Diversification wasn’t a growth gimmick—it was a strategic defense after losing top clients and recognizing weaknesses in truckload execution.Truckload procurement vs. traditional brokerage: How Evans built a carrier procurement engine designed to protect managed transportation performance rather than operate as a pure sales brokerage.The modern 3PL approach and blind bidding: How Evans structures managed transportation so shippers can keep multiple brokers in the mix while Evans competes fairly without undercutting.How managed transportation adoption has changed: Why most shippers are already using 3PLs, how the sales cycle has shifted to CFOs and VPs, and why strategic sponsorship matters.Why Evans avoids price wars and “broker poker freight”: Their focus on value, complexity, and long-term trust instead of transactional spot quoting.How to build trust by saying no: Why Evans intentionally accepted only 3 of 13 specialized moves to avoid failure and earn long-term credibility.The blueprint for launching new service lines: Why face-to-face time, slowing down, and releveling teams matters more than speed when integrating new divisions.Evans’ culture operating system: Quarterly in-person rhythms, shared experiences, and a “do life together” philosophy that fuels cohesion across remote leadership.AI as a relationship accelerator: How automation reduces noise so brokers can invest in carriers, deepen relationships, and drive better outcomes. Time-stamped highlights (00:00) Introduction to Ryan Keepman and Evans Transportation(01:14) The Early Years and Founding Story(03:48) Starting Evans with High Risk and Early Challenges(07:32) Evolution from Brokerage to Managed Transportation(08:16) Early TMS Development and Technology Advantage(09:19) Leadership Transition to Ryan(10:02) Diversification Strategy and the Truckload Division(11:07) Expansion into Mexico, Specialized, Parcel, and Government(13:09) Managed Transportation and Truckload Procurement(16:28) Modern 3PL Model and Blind Bidding(19:55) Shipper Trends and Managed Transportation Adoption(24:35) Building a Moat with Parcel and Full-Suite Solutions(25:46) New Warehouse Product and Strategic Fit(28:28) Avoiding Price Wars and Competing on Complexity(32:00) Building Trust Through Gradual Growth and Saying No(35:08) Lessons Learned in Launching New Service Lines(40:08) Evans Culture and the “Do Life Together” Approach(44:16) Leading Distributed Teams with Quarterly In-Person Rhythms(48:10) Leadership Growth, Directness, and Personal ReflectionGuest Ryan Keepman — CEO, Evans TransportationRyan Keepman has spent 19+ years at Evans Transportation Services, building his career across key accounts, sales leadership, and executive leadership roles. He became CEO in December 2020 after serving as President (2018–2020) and previously leading growth as Vice President of Logistics Sales (2014–2020) and Vice President of Key Accounts (2007–2020). Under his leadership, Evans has evolved into a diversified logistics partner spanning managed transportation, truckload procurement, Mexico, specialized solutions, parcel, government services, and new warehousing offerings—while maintaining a people-first culture built on trust, accountability, and shared experience. LinkedIn: https://www.linkedin.com/in/ryan-keepman-75246610/ Links & references Evans Transportation: Family-owned logistics provider offering managed transportation and multimodal solutions — https://www.evanstrans.com/Strength to Strength (Arthur C. Brooks): A framework for reinvention and sustaining fulfillment through midlife transitionsTransportation Deregulation (Motor Carrier Act of 1980): The policy shift that reshaped the freight brokerage industryBrought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    57 min

  7. JAN 6

    Fura CEO Jeff Dangelo on Why Most Freight Transformations Break at Adoption

    The real bottleneck in freight technology isn’t innovation — it’s adoption, misaligned incentives, and the absence of ownership over cultural change. Jeff Dangelo has lived every side of that problem: early at TQL, helping scale MegaCorp Logistics, founding the freight collaboration platform Turvo, and now leading Fura as CEO. In this episode, Jeff breaks down what really makes brokerages scale (and where common models break), why most “digital transformation” initiatives stall, and how Fura’s acquisition strategy targets underperforming brokerages and gets them from manual to digital in a matter of months. We dig into the trust-building required to integrate teams, how to decide whether to build vs buy software, and why AI can shrink the adoption gap by running “in parallel” with people — not forcing everyone to change overnight. What you’ll learn How freight brokerages actually scale: Why TQL “played the percentages,” built a culture engine, and used hiring + activity math to compound growth.Cradle-to-grave vs team-based brokerage models: What breaks in the classic spin-out approach, and how MegaCorp kept teams intact to protect continuity and service.Why most digital transformations fail: The real blocker isn’t software — it’s behavior change, incentives, and lack of discovery/business-case selling.Fura’s M&A thesis in a down cycle: The three seller buckets, why “losing money or break-even” firms can be ideal, and how Fura modernizes fast.How to integrate culture without breaking it: The “earn trust” approach — engagement loops, surveys, all-hands, and executive sponsorship.Build vs buy decision-making: The matrix Fura uses (speed, business case, differentiation/IP) to decide what to own vs partner for.Network-based selling in freight: How Fura maps nodes (vendors/customers/suppliers), uses proof of impact, and links sales + ops to drive adoption.AI as an adoption accelerator: Why AI can run in parallel with people to reduce friction — and how that reshapes brokerage into a more strategic model. Time-stamped highlights (00:00) Tech Adoption and the Manual-to-Digital Gap(01:00) Jeff Dangelo’s Freight and Tech Background(04:00) Early TQL and Boiler Room Culture(07:00) TQL’s Hiring and Scaling Engine(10:00) Data-Driven Growth and Hurricane Interns(14:00) The Cradle-to-Grave Churn Problem(18:00) MegaCorp’s Team-Based Fix(23:00) Selling Freight vs Selling Software(28:00) Turvo and the Adoption Challenge(33:00) Fura’s Consolidation Strategy(37:00) The Three Seller Buckets(41:00) Structuring Turnaround Deals(45:00) The Integration Trust Playbook(48:30) Standardizing Systems at Scale(50:30) Build vs Buy Decisions(51:30) The Future of Brokerage With AI(52:04) Closing Thoughts on Execution Over VisionGuestJeff Dangelo — Co-Founder and CEO, FuraJeff is a freight industry veteran with 20+ years across brokerage, technology, and M&A. He helped scale TQL and MegaCorp Logistics, founded Turvo, and now leads Fura, where the team acquires and modernizes brokerages by combining automation, execution, and disciplined integration.LinkedIn: https://www.linkedin.com/in/jeff-dangelo-8a7107a/ Links & references Fura: Brokerage + modernization platform focused on acquiring and digitizing underperforming brokerages — https://fura.com/Turvo: Freight collaboration platform Jeff founded focused on shared workflows across shippers, brokers, and carriers — https://turvo.com/TQL: High-output brokerage known for systems-driven hiring, training, and culture — https://www.tql.com/MegaCorp Logistics: Brokerage scaled with a more team-based operating model and continuity focus — https://www.megacorplogistics.com/Brought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    52 min

  8. 12/16/2025

    Bill Driegert (DAT) on the Technology That Actually Sticks in Freight

    Freight tech hype cycles come and go, but what actually sticks inside brokerages, carrier ops, and shipper TMS screens? The “Steve Jobs of freight,” Bill Driegert, traces the real arc of innovation in trucking – from American Backhaulers and the “Chicago model” to Uber-for-Freight experiments, digital freight matching, AI dispatchers, and the Convoy acquisition by DAT. Bill has sat in almost every important seat in modern freight: early at Coyote, co-founder of Uber Freight, Head of Trucking at Flexport, part of the Convoy story, and now leading carrier products and strategy as EVP of Convoy Platform at DAT. He breaks down why each “epoch” of freight tech took a decade to matter, why pure-play digital brokers hit a ceiling, what the DAT + Convoy combo unlocks, and how AI, AVs, and scheduling will reshape the next 10–20 years. What you’ll learn The real tech epochs in freight: From post-deregulation brokerage and the American Backhaulers / CH Robinson split, to broker TMS, to “Uber for freight,” to today’s AI and automation wave.Why “digital freight matching” stalled as a standalone model: The hard TAM limits of being “product pure,” and why the biggest brokers will build, while everyone else partners.Chicago vs cradle-to-grave brokerage models: How floor design, org structure, and TMS shape service, density, and which shippers you can actually win.Fragmentation, scale, and the future of brokers: Why tech makes midsize brokers more dangerous, why service still wins with SMB shippers, and why you shouldn’t bet on a winner-take-all market.AI’s real role in brokerage and dispatch: Where AI and “AI dispatchers” add value, where they just create more work, and why channel choice (app, TMS, email, phone) really matters.Autonomous trucks and carrier consolidation: How AVs could change capital requirements, operating models, and what a “carrier” even is – plus how brokers and 4PLs might evolve around them.Why scheduling is the final frontier: How appointment setting, facilities, and dock operations quietly cap automation – and why solving scheduling unlocks the next big efficiency leap.Time-stamped highlights (00:00) Bill’s background across Coyote, Uber Freight, Flexport, Convoy, and DAT(05:00) Post-deregulation brokerage 101: CH Robinson vs American Backhaulers and the birth of the Chicago model(11:00) Building Coyote’s broker TMS and why V1 tech focused inside the four walls of the brokerage(16:00) Uber launches, “Uber for freight” is born, and why early apps were just mobile load boards(22:00) Convoy, Transfix, Uber Freight and the true end-to-end “app-first” operating model(27:00) Why pure digital brokers ran into TAM limits and why only the largest players can justify full-stack builds(33:00) What shippers actually care about: why transportation is often priority #5, not #1, in the C-suite(39:00) SMB vs enterprise shippers: how Landstar-type agents win locals while big RFPs reward scale and data(45:00) Fragmentation, minimum efficient scale, and whether broker consolidation really happens(51:00) AI in the wild: AI dispatchers, robocalls, and why every extra medium (phone, email, portal) is a process defect(57:00) How apps, TMS integrations, and “one-click” workflows beat phone calls for both carriers and brokers(1:02:00) AVs and the carrier of the future: capital intensity, new operator models, and deterministic dispatch(1:10:00) 4PLs and managed transportation in an AI/AV world: why the role changes but doesn’t disappear(1:16:00) Inside the DAT + Convoy + Truckers Tools + Outgo stack: what Bill’s building for carriers and brokers now(1:22:00) Scheduling as the under-loved bottleneck: why docks, facilities, and appointments still block automation Guest Bill Driegert — EVP of Convoy Platform, DAT Freight & AnalyticsBill has been at the center of nearly every major freight-tech wave of the past 15 years. He was an early employee at Coyote Logistics, co-founded Uber Freight, led trucking at Flexport, and now guides carrier strategy and product at DAT following the acquisition of Convoy’s technology.LinkedIn: https://www.linkedin.com/in/driegert/Links & references DAT Freight & Analytics: Load boards, rates, and network intelligence for brokers, carriers, and shippers — https://www.dat.com/Convoy (acquired technology by DAT): Background on the digital brokerage and platform Bill helped integrateUber Freight: Digital brokerage and 4PL / managed transportation offering — https://www.uberfreight.com/Coyote Logistics: Large brokerage built on the “Chicago model” Bill joined as an early employee Brought to you by VOOMA — Vooma helps brokers and carriers win and move more freight. Their AI Orchestration platform automates SOPs across the full Quote-to-Cash lifecycle helping teams focus on the tasks that actually move the needle for the business. Book a demo now: https://www.vooma.com/

    57 min
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About

The Freight Show brings stories of freight and logistics leaders who’ve shaped the industry. Through in-depth conversations, we explore their journeys, the challenges they’ve overcome, and the insights that have driven their success. Each episode uncovers the lessons, strategies, and wisdom of these freight leaders.

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  • Creator
    Vooma
  • Years Active
    2025 - 2026
  • Episodes
    20
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    Clean
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    © 2026 Vooma