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Forty-one years is a long time to run one software company. Tom McLeod started McLeod Software in 1985, five years after deregulation blew open an industry that had been run like a public utility, and he's still at the helm today with 550 employees, no outside investors, and a product line that just went through a complete revamp. In the mid-80s, dozens of small software companies were all trying to build the operations platform for trucking. McLeod rose above the fray by the mid-90s, and Tom has a clear view of why. That view matters right now because he sees the same pattern playing out again. Dozens of AI companies are springing up to serve transportation, the way dozens of software companies did forty years ago, and Tom's read is that the winners will be decided by the same things: focus, picking the right customers, and not promising more than you can deliver and service. In this conversation he walks through the early years selling the first 50 systems himself, the decision to exit the brokerage software market for several years in order to win trucking first, how a group of 30 to 35 customers shaped the PowerBroker rewrite through biweekly sprint demos, and why he views freight brokers as America's secret weapon for an efficient transportation system. He also gets into why every attempt at a vertical technology stack in freight has failed, how McLeod is using AI inside its own development, testing, and support teams, and the one piece of advice he'd give any founder entering the market today. What you'll learn: - Why deregulation created the software industry for trucking: how the end of franchise rights in 1980 turned manual, utility-style carriers into companies with a reason to get efficient - Why brokers are the secret weapon of US freight: how a shipper's top-20 carrier list runs out and a broker's hundreds of carrier relationships fill the gap - The case for focus over reach: why McLeod stepped away from brokerage software for years to win trucking first, then came back with PowerBroker in 2006 - How to run a customer advisory process that actually steers the roadmap: why one customer's input is a trap, and how 30 to 35 companies watching sprint demos every two weeks reshaped the product - Why fragmentation protects incumbents: how dozens of niche markets inside trucking make it hard for new entrants, and how configurability and an API answer that - Why the vertical stack never works in freight: the mid-90s competitor that fell behind on integrations, and how mobile comm providers started bringing McLeod their customers - How AI fits the 40-year arc of trucking software: why eliminating the manual work behind 40 to 50 percent of ops emails is the same job as automating the freight bill - What building without outside capital made possible: the luxury of time, the long view, and the one loan McLeod ever took - Tom's formula for AI vendors entering freight: focus, pick the right customers, don't outkick your coverage, sell a ton, and build great product Time-stamped highlights: - (00:00) Intro: 41 years of McLeod Software - (01:01) Deregulation, turbulence, and why disruption creates opportunity - (01:31) What trucking looked like under regulation: franchise rights to haul freight and the flood of new carriers after 1980 - (02:28) Dozens of software startups in the mid-80s and the parallel to today's AI field - (04:10) Why incumbents ran manual operations: regulated like a utility, entitled to a 15 percent profit - (05:14) Early customers who ran both trucking and brokerage, and the first two TIA lifetime achievement winners - (06:14) Brokers as America's secret weapon and why shippers keep a top-20 list - (07:38) Exiting the brokerage software market for several years to focus on trucking - (08:36) The complete product rewrite and the launch of PowerBroker in 2006 - (10:44) What trucking and brokerage systems share and why separate teams build the operations tools - (13:25) What separated McLeod from the pack: focus, blocking and tackling, and the long-term view - (14:23) Choosing an industry that couldn't be offshored - (14:52) Building a development feedback loop with customers and an advisory council - (15:50) Growing through the late 90s with zero unemployment in the computer field - (16:49) Why you can't let a single customer drive the roadmap - (17:46) 30 to 35 companies watching sprint demos every two weeks during the PowerBroker rewrite - (18:45) How customers flip McLeod's internal development priorities - (20:27) Niche markets inside trucking and why they make it hard for new players to attack - (22:40) Focusing on flatbed, van, and refrigerated while adding configurability for liquid, heavy haul, and bulk - (26:02) The API and how customers build bolt-on solutions - (28:22) Tom's view on AI: the same job as eliminating the typed freight bill and driver paycheck - (29:48) Why 40 to 50 percent of ops emails require manual work - (30:46) Dozens of AI startups and the greenfield of the mid-80s - (32:31) Why vertical technology stacks haven't worked in freight - (33:01) The mid-90s competitor that fell behind on integrations and how mobile comm providers brought McLeod customers - (35:30) The goal to demonstrate how to best use AI in a transportation operations product - (36:58) How McLeod uses AI internally: developers, cybersecurity, testing, and 300 new knowledge base documents - (39:42) Why McLeod never took venture capital, or as it was called then, vulture capital - (41:07) The luxury of time and how it made long-term decisions easier - (41:36) The one time McLeod borrowed money: the product rewrite during the 2001 recession - (43:04) What keeps Tom energized after 41 years and 550 employees - (44:34) From sales to programming, and selling the first 50 systems himself - (46:57) Tom's advice for AI vendors entering freight: focus and pick the right customers - (48:26) Why PE groups are learning the value of sales orgs, and the problem of overestimated TAMs - (49:24) Don't outkick your coverage: why services matter as much as the product - (49:52) Why getting an AI prompt to 70, 80, 90 percent is easy and the rest takes time - (51:32) See you in Nashville at the 2026 McLeod User Conference Guest: Tom McLeod — President, McLeod Software Tom founded McLeod Software in 1985 and has led it for 41 years, growing it from a startup selling its first systems by hand into a 550-person company with a leading transportation management platform for carriers and brokers. He began his career in sales before moving into programming in the early 80s, and sold McLeod's first 50 systems himself. He has never taken outside investment, and today he is leading the company through a full revamp of its product line and the integration of AI across its products and operations.

Every broker on the phone is pitching service. Jacob Benbenek has a harder proof point than most: Magna has never had a fraud incident in 14 years of business, and his carrier reps get paid on loads that lose money exactly as if they made a hundred dollars. Ask him how a small team stays disciplined on a hard-to-cover load at 4:30 on a Friday, and the answer starts with how people get paid, not with a compliance tool. Jacob spent ten years on big brokerage floors before he started Magna, a Chicago boutique focused on dry van freight in the lower 48 east of the Mississippi. He sat in a parking lot for an hour before he could make himself walk in and resign, took a massive pay cut, and started with three partners, four computers, and a spreadsheet of shippers pulled off Google over the weekend. The first load was Woodchuck hard cider. Fourteen years on he has bought out the last of his partners and built a shop that goes after just-in-time enterprise freight against brokers many times its size. In this conversation, Jacob explains the pay structure that gets a $1,000 losing load worked like a $100 winner, why the preferred carrier at $1,300 beats the unknown carrier at $1,200 every time, and the smell tests his team ran on carriers years before RMIS and Highway existed. He also gets into the rule that every new hire tracks loads for their first three to six months, the check call policy he wrote at the start that still runs alongside the tracking pings, and why the one-to-two-hour gap between a load being sold and a driver being verified is where most shipments actually fail. What you'll learn:- Why Magna pays carrier reps on losing loads: how treating a $1,000 loss like a $100 win removes the incentive to slap a shaky carrier on a load and walk out the door- How incentives connect to fraud: Jacob's view that most fraud and most mistakes come from "pushing sausages through the factory too fast," and why five or ten seconds of qualifying prevents a catastrophe- What fraud prevention looked like before the compliance tools: the running list of red flags, license plate and ID photos, and the smell tests every rep is trained on- Why every new hire tracks loads for three to six months: how the rule teaches internal communication, what to look for, and why Jacob says Magna operates differently from a big floor- Why tracking tech doesn't replace the check call: the policy Jacob wrote at the start, why a ping an hour out doesn't mean on time, and the sold-to-verified gap where shipments fail- How a boutique competes for enterprise freight: the case for just-in-time shippers working with a team that gives the same high-level touch all day and into after hours- Why "be really good at something" beats a hundred offerings: how Magna picked dry van east of the Mississippi and stopped chasing the customers who email 50 brokers at once- What the market transition looks like from a boutique: rebids, spot activity down, and why Jacob says the years of building through the down market are paying off now- Who succeeds at Magna: the Chicago Public Schools teacher who came in through operations and became the best account executive on the floor, and what "take ownership" means day to day Time-stamped highlights:- (00:00) Intro: everything has been rebid, new pricing is in, and spot activity is down across the board- (01:54) Why Jacob says the market transition was necessary and how Magna balanced contract freight against spot- (04:10) The customer Magna wants: sophisticated enterprise accounts, not five or six loads a week- (05:20) What "boutique" means in practice: an owner on the floor every day and the inefficiencies Jacob took out of the big-floor model- (08:48) The decision to leave a stable job, the massive pay cut, and an hour sitting in a parking lot before resigning- (10:29) "There was nothing wrong with my path, but I knew it wasn't my path"- (11:13) Four computers in a small room and calling shippers sourced off Google- (12:23) Three partners, a buyout three years ago, and the first load: Woodchuck hard cider- (12:52) Two or three loads on the board, no carriers willing to work with them, and the Centralia auto-rack account that started the mojo- (14:43) Alone in the office for nine hours on a snowy day, calling off a spreadsheet- (16:02) The pitch that won early freight: knowing the region and the seasonality, not name-dropping former employers- (17:57) Why a just-in-time enterprise shipper is a bad fit for a huge shop- (18:57) Payless versus Gucci, and why the operations team is not data entry- (21:20) Refusing to be on an email with 50 brokers, and picking dry van in the lower 48 east of the Mississippi- (24:00) The rule: every new hire tracks loads for three to six months, no matter their experience- (27:04) What new hires learn: internal notes on every shipper and receiver, and reading between the lines- (29:13) Who does well at Magna: extremely hard-working, hungry people who love teams- (30:19) Low turnover, three or four interviews, and spotting a whatever-it-takes attitude- (31:19) The Chicago Public Schools teacher who became Magna's best account executive- (35:18) Team structure: carrier, operations, tracking, and outsourced night tracking- (36:16) The check call policy Jacob wrote at the start, and why reporting a pickup after the actual time is a failure- (38:17) Qualifying the load properly and the one-to-two-hour gap between sold and verified where shipments fail- (40:17) "Old school stuff" and why understanding the pulse of the market every morning is how you make money- (42:58) Everybody preaches service; how Magna gets the shot to prove it- (45:07) Fourteen years fraud-free: the red-flag list, license plate and ID photos, and smell tests before compliance tools existed- (47:00) "Pushing sausages through the factory too fast" and the five or ten seconds that prevent a catastrophe- (48:38) Why carrier reps get paid on losing loads as if they made $100- (49:38) Every load gets worked like a winner, and why the bottom line is what matters- (50:55) The preferred carrier at $1,300 over the unknown at $1,200, and why cutting corners doesn't go far Guest:Jacob Benbenek — President, Magna Jacob spent ten years at two large brokerages before starting Magna in Chicago with three partners, buying out the last of them three years ago. Magna is a boutique 3PL focused on dry van freight in the lower 48 east of the Mississippi, built around just-in-time enterprise shippers in manufacturing and beverage. Fourteen years in, he is still on the floor every day, and the company has never had a fraud incident.

Most brokerages that stall in the $40-50M range never get out. The math is unforgiving: growing means hiring, onboarding, and training faster than the volume arrives, but staffing ahead of volume burns cash you don't have yet. American Diamond Logistics sat at $44-45M for three straight years. Then, in a matter of months, its run rate jumped to nearly $100M. Steve Wineriter has been in freight since 2002, when he joined his dad's 3PL out of college. After founding American Diamond, he made a decision that had no business working: in 2016, as a roughly $5M company, he built his own TMS and GPS tracking platform, sketched out on an actual bar napkin after a chance meeting on a shuttle bus. Navigator and Freight Tracer went live January 1, 2017, and within five years the company had scaled past $50M. One of the largest 3PLs on the planet later subcontracted American Diamond on one condition: don't show the client your technology, because it's better than ours. In this conversation, Steve breaks down what it actually takes to break through the revenue ceiling: why the plateau is a staffing math problem rather than a sales problem, how automating carrier calls, load sheets, appointments, and track and trace turned a floor that sounded like the New York Stock Exchange into a quiet one, and why his agent department went from zero to over $20M in three years. He also gives his read on the strangest freight market of his 25-year career. What you'll learn: - Why the $50M ceiling is a staffing math problem: the chicken-or-egg trap where 3PLs wait for volume before hiring, then can't onboard fast enough when it arrives- The bar-napkin TMS: how a $5M brokerage built Navigator and Freight Tracer with outsourced developers and why owning the roadmap became the business model- Why Steve wanted a sales-centric TMS when everything on the market was a back-office data placeholder, and how it changed his reps' first 60 seconds with a prospect- The Starbucks meeting where one of the biggest 3PLs in the world asked American Diamond to hide its technology from a shared client- Why the agent model outpaces hiring salespeople: non-solicits handcuff new hires for 12-24 months while agents bring their book with them- What changed on the floor: 15-20,000 inbound calls a week, now handled without a human picking up, and Steve's motto that AI handles the transactions so staff can manage the relationships- How John Drager, one of the leading figures behind Landstar's agent success, is scaling American Diamond's agent department- Steve's market read: why this is a supply-driven market unlike anything since he started in 2002, and why he thinks demand in 2026-27 could outpace COVID- Why data is currency: how capturing every spot quote gives American Diamond pricing visibility when tools like DAT are going back to the drawing board Time-stamped highlights: - (00:00) Intro and Steve's vision for a technology-centric 3PL- (02:19) The old solicitation model: a salmon swimming upriver- (02:48) Building a TMS at $3.5-5.5M in revenue with no business doing it- (04:39) The trampoline park, the shuttle bus, and the chance meeting that started it all- (05:38) Sketching the TMS on an actual bar napkin in New Orleans- (06:07) Building a GPS platform without knowing Macro Point existed- (07:29) Spinning the technology out as its own company and giving developers equity- (07:58) Why the TMSs of that era were back-office data placeholders, not sales tools- (08:57) Going live January 1, 2017 at $6M and scaling past $50M in five years- (10:34) The mystery call that turned out to be one of the biggest 3PLs on the planet- (11:26) "Do not share your technology with the client, because it's better than what we have"- (13:27) Starting in freight in 2002, when a loaded trailer disappeared around the corner- (14:23) Tracking through the driver's phone, pinging every five to ten minutes- (15:50) Fighting 30-40% driver acceptance in the early days- (18:53) Turning internal lane data into a carrier RFP tool- (19:46) Covering a load at the projected rate in three minutes with a 500-carrier blast- (22:00) Learning the business at his dad's 3PL and discovering the agent concept- (23:25) Why agents scale faster than salespeople stuck under non-solicits- (24:22) Over $20M in agent revenue by the third full year- (25:47) What agents actually care about: the split and the model- (29:16) Change management with traditional agents and the light-bulb moment- (31:17) The floor that sounded like the New York Stock Exchange, now silent- (33:43) John Drager, Landstar, and "I hope you're ready for hundreds of millions of dollars"- (39:22) Three flat years at $44-45M, then a run rate near $100M- (41:19) The chicken-or-egg staffing trap that keeps 3PLs at the ceiling- (42:12) 15-20,000 inbound calls a week and the opportunities that got missed for 15 years- (44:21) "I was not a very good operator back then. We were just printing money."- (45:18) AI handles the transactions so staff can manage the relationships- (48:09) Educating shippers: the first one to find a truck gets the load- (50:37) The strangest market in Steve's 25 years and what makes it supply-driven- (52:58) Why demand in 2026-27 could outpace COVID- (58:49) Data is currency: capturing every spot quote- (59:17) How AI agents should talk to dispatchers, and avoiding carrier fatigue- (01:02:03) What Steve is most excited about for the next 12 months Guest:Steve Wineriter — Founder & CEO, American Diamond Logistics Steve started in freight in 2002 at his father's 3PL and went on to found American Diamond Logistics, where he bet a $5M company on building its own TMS and GPS tracking platform in 2016. That technology became the business model: American Diamond scaled past $50M within five years of launch and now sits at a run rate near $100M, powered by a fast-growing agent department and an operating model where AI handles the transactions and people manage the relationships.

Going into the Montgomery case, everyone expected the brokers to win. The FMCSA and the Department of Transportation both filed on the brokers' side. Matthew Leffler, a supply chain attorney and law professor, called it for the brokers too. The Supreme Court came back unanimous, against them, and wiped out a presumption the entire brokered freight model was built on: that when a motor carrier has a catastrophic accident, the broker isn't the one who pays. Matthew calls Montgomery the most profound Supreme Court decision ever handed down for brokers and 3PLs, and in this conversation he explains why. The ruling leaves two questions nobody can answer, not even the regulator: what makes a motor carrier unsafe, and what counts as a reasonable vetting process? With 94% of carriers carrying no safety rating and 6,000 new ones entering every month, brokers are now held to a standard the FMCSA itself can't define, and the only way answers arrive is through litigation. From there the conversation widens out into the forces that got the industry here: deregulation since 1980, the beacon waiver quietly clearing the road for autonomous trucks, the cargo theft wave and the CORCA bill stalled in the Senate, and the Slaughter decision reshaping who controls the federal agencies that regulate freight. What you'll learn: Why Montgomery matters more than any prior broker case: how it erased the decades-old presumption that a carrier's accident wasn't the broker's liability, across every federal circuit at onceHow the circuit split actually formed: why the Ninth and Seventh Circuits read the same 1994 F4A statute and reached opposite conclusionsThe two unanswerable questions the ruling created: what is an unsafe carrier, and what is a reasonable vetting process, and why only litigation can settle themWhy carriers are effectively judgment-proof: the $750K minimum insurance set in 1985, and why plaintiff attorneys now name the broker in every suitWhat a defensible vetting process looks like in practice: written policy, no deviation, and pressure-testing it with your insurer and outside counselWhy insurance premiums are already up 3 to 5x, and how discovery will pull every big broker's "proprietary" carrier-selection process into the openHow deregulation since 1980 set the stage: 18,000 carriers then versus 600,000 now, the collapse of trucking's union share, and the $8B consumer-savings bet behind the Motor Carrier ActWhy the technology for autonomous trucks is ready and regulation is the only barrier: the beacon waiver, remote-operator questions, and a rulemaking that drew fewer than 400 commentsHow organized cargo theft actually works now: cartels hacking ELDs to reroute trucks, and why CORCA is the tool built to fight itWhat the Slaughter decision changes: the end of for-cause protection at federal agencies and what that means for the regulators over freightTime-stamped highlights: (00:00) Matthew on why he's rooting for the robots(01:32) Why Montgomery is the most profound Supreme Court decision ever for brokers and 3PLs(02:26) How brokers went from moving ~5% of freight to 25-30%(03:17) The circuit split: Ninth Circuit vs Seventh Circuit on the same F4A statute(04:18) The unanimous ruling, Matthew admitting he was wrong, and the two questions with no answers(05:04) Why litigation is now the only path to answers(05:49) The travel-agent analogy for what freight brokers actually do(06:17) The FMCSA's billion-dollar budget against 600,000+ carriers(07:12) How brokers vet on price, route, and service, and where the gap opens(08:09) The $750K insurance minimum set in 1985 and the underinsured-carrier problem(08:35) Why plaintiff attorneys go after brokers, shippers, and leasing companies(09:55) The US Chamber, TIA, FMCSA, and DOT all filing on the brokers' side(10:54) How carrier safety audits actually work, and the conditional-rating problem(11:24) 6,000 carriers a month, and why vetting tools can't tell you if a driver is sleepy(12:18) What Matthew would tell a brokerage to do right now(13:55) No legal requirement to carry contingent auto, and why you need it anyway(14:24) Premiums up 3 to 5x as insurers price in the new liability(16:14) The plaintiff strategy of suing everyone with money left(17:06) Why every broker's confidential vetting process is headed for discovery(21:13) The Wabash case: a $462M Missouri verdict and how tort reform revised it(23:29) Private equity and venture money now backing plaintiffs(23:57) The 22% out-of-service rate: one in five trucks unsafe(25:07) The deregulation story, starting with his father at Roadway in 1976(27:12) Carter, the Motor Carrier Act, and the $8B consumer-savings bet(27:32) Roadway Package Systems to Caliber to FedEx Ground(30:47) Kodiak and Aurora hauling Houston to Dallas every day(31:43) The beacon waiver and the broken-down autonomous truck problem(32:40) The rulemaking that drew fewer than 400 public comments(37:48) Why California has tried to ban driverless trucks twice(40:31) Reported cargo theft near $1B, with estimates as high as $35B(42:35) CORCA explained, and why it's stalled in the Senate(46:34) How cartels hack ELDs and reroute trucks without the driver knowing(50:27) The Slaughter case, Chevron, and the reshaping of federal agencies(58:11) What Matthew is most excited about over the next twelve monthsGuest: Matthew Leffler — supply chain attorney and law professor, known as The Armchair Attorney Matthew has spent 15 years in litigation across the freight and supply chain world and teaches as an adjunct law professor. He grew up in the industry: his father started a company maintaining equipment for Roadway Package Systems, the business that became Caliber and then FedEx Ground. Today he writes and speaks widely on the legal forces reshaping brokerage, from broker liability to autonomous trucking.

Look at a freight brokerage P&L the way most investors do and you'll see a 10 to 20% gross margin, a 3 to 8% EBITDA margin, and a business at the mercy of the freight cycle. Brandon Wolfe looks at the same numbers and sees one of the most underestimated business models in the country. The catch, he says, is that the best brokerages stay private, so almost nobody gets to see what the model actually produces. Brandon is Co-founder & Managing Partner of Jordan Partners, a Raleigh-based private equity firm that aims to be the first institutional capital into growing, bootstrapped companies, and the owner of Sage Freight, a brokerage in suburban Nashville. In this conversation he makes the investor's case for brokerage: why gross margin is an accounting artifact rather than a measure of business quality, and how the model produces 20%+ returns on capital "from C.H. Robinson on down." He also explains where the pricing floor comes from when independent drivers exit the market, and why buying near that floor, as Jordan Partners did with Sage, is like buying the equity of a coiled spring. He also gets into the interest-cost math that quietly separates subscale brokers from scaled ones, what the Montgomery decision means for compliant operators, his build-versus-buy framework for technology at Sage, and why he's convinced AI will advance the brokerage model rather than disintermediate it. What you'll learn: Why brokerage is underestimated: booking the full transaction as revenue makes gross margin look thin, when return on capital, not margin, is the real measure of business qualityThe math behind 20%+ returns on capital: how a 2-4% net margin on a 10-20% gross margin business compounds, and why the best brokerages never have to go publicWhy Brandon trusts net income over EBITDA: the games that get played with EBITDA, including capitalizing tech spend, a shell game any future buyer will unwindHow interest costs change with scale: the delta between subscale factoring and an ABL is hundreds of basis points on the entire outstanding balance, and it disappears as you growWhere the pricing floor comes from: independent drivers leave the market below a certain cost per mile, which puts a bound on the downside that most variable-pricing industries don't haveHow to operate through the cycle: keeping your foot on the gas in the downturn, hiring and automating while everyone else cuts, then letting operating leverage flow through in the recoveryWhat business mix he underwrites: stable end markets like CPG and consumer staples, a blend of enterprise and mid-market customers, and no single account dominating the bookHis build-versus-buy framework: integrate the best off-the-shelf technology available, and build in-house only in the specific spots where you can genuinely do it betterWhat the Montgomery decision changes: good actors gain a competitive advantage, insurance costs rise, and fly-by-night operators get pushed outWhy AI won't disintermediate brokerage: if load boards didn't kill the model, automation-first execution with humans on the edge cases won't eitherTime-stamped highlights: (00:00) Intro(00:37) What Jordan Partners does: first institutional capital into growing, bootstrapped, unlevered companies(02:04) Why supply chain: making microeconomic bets in industries that are slow to change(06:57) Sage Freight, Jordan Partners' first supply chain investment(08:04) Why brokerage is one of the most underestimated business models in the country(08:58) The accounting quirk: booking the entire transaction as revenue(09:57) 20%+ return on capital "from C.H. Robinson on down"(10:26) Why Brandon is a net income investor, not an EBITDA investor(12:37) Financing the float: factoring, interest costs, and the sanity check on net income(14:04) The delta between subscale and scaled financing: hundreds of basis points, millions of dollars(15:07) Margins are a function of accounting rules; return on capital is a function of business quality(17:03) Where the pricing floor comes from when independent drivers leave the market(18:02) Keeping your foot on the gas through the downturn(18:31) Buying the equity of a coiled spring(20:26) The microeconomic bet: business mix, end markets, and customer concentration(25:29) Why brokers win by implementing technology, not inventing it(29:52) The Walmart model: dividend efficiencies back to customers and take share(31:06) Low-cost producers in inflationary vs. deflationary markets(34:45) Asset light vs. capital light, and why depreciation is near the top of Brandon's fear list(37:26) The Montgomery decision: good actors win, insurance costs rise(43:57) Why capitalizing R&D to boost EBITDA is a shell game(46:00) Build vs. buy: best-in-class off-the-shelf, integrated well, with selective in-house modules(52:38) Why big brokers build in-house: technical debt, office politics, and "don't break the COBOL"(57:12) "We will never be a tech company. We're a freight brokerage."(58:40) Brokerage as a trading system: when you find an edge, you don't broadcast it(01:01:03) The next five years: automation first, edge cases handed to teammates(01:03:34) If the internet didn't disintermediate brokers, will AI?(01:05:32) Managed transportation and earning the right to expand(01:08:07) What Brandon is excited about: pricing turning positive(01:09:12) The Jordan Mines story behind the firm's nameGuest: Brandon Wolfe — Co-founder & Managing Partner, Jordan Partners Brandon co-founded Jordan Partners, a Raleigh-based lower middle market private equity firm that aims to be the first institutional capital into growing, bootstrapped companies across supply chain, financial services, and compliance. The firm's first supply chain investment is Sage Freight, a brokerage based outside Nashville. Before founding the firm, Brandon spent 15 years investing across public and private markets, starting in payments, where he built his conviction that return on capital, not margin structure, is what reveals business quality.

For decades, brokerage has run on two assumptions: pay your reps on commission, and stay asset-light. Shannon Breen built FreightVana by breaking both. What happens when you strip commissions out of a brokerage entirely and own the trailers instead of the trucks? Shannon spent his corporate career inside a large public truckload carrier, where he helped stand up the power-only business after the Knight-Swift merger in 2017. He saw the structural problem up close: inside an asset-based carrier, the company trucks always win, so the partner-carrier network gets suboptimized every time the market turns. He left to build FreightVana on the inverse bet, own the trailers, partner for the power, and pay no commission so the whole team is aligned with the shipper and the carrier instead of the margin on any one load. Today FreightVana runs committed trailer networks for 150 of the largest shippers in the country. He also gives a sharp read on the current market: why the historic four-week spot run is squeezing committed freight networks, why this is not a repeat of COVID, and how rising standards and liability after Montgomery could split brokerage into two tiers. What you'll learn: Why FreightVana runs with no commission structure: how removing per-load incentives keeps the team aligned with shippers and carriers instead of extracting margin on every move"There are no solutions, only trade-offs": the cost Shannon accepted to build a non-commissioned model and why he'd make the same call againWhy he owns the trailers but not the trucks: the "totem pole" problem inside asset-based carriers that makes a true partner network impossibleHow a trailer-led model actually wins shippers: drop-trailer flexibility, interchangeability, and security standards a traditional broker struggles to matchWhy length of haul matters more than raw utilization: how a sub-200-mile drop pool becomes quasi-dedicated, and why FreightVana targets 500-plus-mile lanes to build a real networkWhat the model unlocks for small and mid-size carriers: drop-and-hook efficiency, less dwell time, and access to Fortune 500 networks they can't reach aloneWhy this market is not a repeat of COVID: the difference between a supply-driven run-up and a demand-driven one, and how Shannon navigates the contract squeeze with authenticity and dataHow rising standards could split brokerage into two tiers: why the top 200 brokers separate from the field, and why the broker's role gets more important, not lessTime-stamped highlights: (00:00) Intro and the state of the market: a historic four-week spot run and the pressure it puts on committed freight networks(01:29) What committed (contract) freight actually means and why a rising spot market squeezes it(01:50) Why this disruption is not a repeat of COVID: supply-driven versus demand-driven(02:50) Servicing 150-plus of the largest shippers in the country and the purview that gives him(04:06) Navigating the contract conversation with authenticity and data instead of emotion(06:09) FreightVana's disciplined pricing model and why you price for network connectivity(07:18) The split: roughly 45% on owned equipment, 55% traditional brokerage, and three pricing models(07:50) Why FreightVana has no commission structure and what drove that decision(09:00) Aligning with the customer instead of making margin on every single load(09:52) "There are no solutions, only trade-offs" and flipping the triangle(11:22) Why lofty commission structures are nearly impossible to undo once they're built(12:11) The Knight-Swift merger in 2017 and building power-only inside a large carrier(12:14) The "totem pole" theory: why company trucks always win and the partner network suffers(14:00) Building FreightVana from the ground up: trailers, technology, pricing, and no commission(14:43) Why FreightVana was not built for a freight recession(15:46) Security and insurance standards, and why he won't scrape the bottom of the barrel for capacity(17:36) The shipper value prop: drop-trailer flexibility and the long-tail carrier's truck-to-trailer ratio(18:36) The 15-trailer interchangeability example and why a fungible pool beats single-lane drops(21:45) Why the largest carriers' stock is up 40% in three months, and what pricing power leaves shippers(22:57) The pain points that signal a fit: freeing operations from live-load appointments(25:13) The carrier side of the value stream: access to Fortune 500 networks a small carrier can't reach alone(26:13) Dwell time, ATRI data, and the drop-and-hook efficiency the model gives smaller carriers(27:46) The typical FreightVana carrier: under 50 trucks, roughly 75% of the trucks on the road(30:00) Pricing discipline and why a commission floor undermines network density(31:21) Trucking's driver-first totem pole versus FreightVana's focus on the trailer network(33:21) Why sub-200-mile drop pools run quasi-dedicated, and why FreightVana targets 500-plus-mile lanes(35:10) The proprietary pricing algorithm reading freight flows behind every RFP(36:51) The Supreme Court / Montgomery decision and what it does to insurance and standards(38:58) The two-tier split: approved high-standard carriers versus a persistent lower-standard market(40:51) Shipper liability, the Texas case, and indemnity clauses in Fortune 500 contracts(42:57) Why the top 200 brokers hold roughly 90% of brokered volume(45:12) Does brokerage's structural role change? Why Shannon thinks it gets more important(52:08) What Shannon is watching next year: market stabilization, AI's ROI, and the broader economyGuest: Shannon Breen — Founder & CEO, FreightVana Shannon spent his corporate career in asset-based trucking, helping stand up the power-only business at a large public truckload carrier following the Knight-Swift merger in 2017. He left to found FreightVana, a brokerage built on an inverted model: it owns the trailers rather than the trucks and runs with no commission structure, betting that alignment with shippers and carriers beats per-load margin. Today FreightVana operates committed trailer networks for more than 150 of the largest shippers in the country.

or three years, asset-based carriers got beaten on price by capacity that hauled freight for half of what a real truck needed to break even. Now the cycle has turned, and the shippers who spent those years chasing the cheapest option are calling back. Harman Cheema is in a rare seat to see all of it: he runs 500 trucks and 2,000 trailers at Cheema Freightlines, plus a brokerage at Cheema Logistics approaching $100M in revenue. He's getting the calls. He's also telling a lot of them to wait their turn. Harman started Cheema Freightlines in 2006 and launched the brokerage three years later, almost by accident, when customers needed more loads covered than he had trucks for. Running both sides through this market has given him a clear read on why rates collapsed, why they're climbing back, and why this correction is different from every other one he's lived through. In this conversation he walks through the zombie capacity that set the market floor, the broker liability ruling and what it means when you do power-only, the 100% driver turnover problem nobody has solved, and why he thinks brokers are about to lose the route-guide seat they've held for a decade. He also gets into the operational reality of running an asset carrier and a brokerage under one roof: when the two businesses present a united front, when they have to be kept completely separate, and how he structures incentives so they aren't fighting each other over the same freight. What you'll learn: - Why his own brokerage was undercutting his own trucks: how the same Seattle-to-LA lane could be covered for $0.50 a mile when his fleet needed $1.25 to break even - How zombie capacity set the floor: why carriers that weren't making truck payments could haul cheaper than anyone, and why the banks let them keep running - What the broker liability ruling actually changes: why it's good news for assets, scary for brokerages, and especially exposed when you run power-only with your own trailer - Why shippers are coming back to asset carriers: how legal teams and falling-off capacity are pushing freight back toward trucks shippers can actually diligence - Why this correction is different from COVID: capacity left and isn't coming back, because the driver pipeline is being cut off rather than refilled - Why trucking has a retention problem, not a driver shortage: the fallback-career dynamic, aging owner-operators, and the dwell time that burns drivers out - Why brokers are about to lose their route-guide seat: how the cheap-capacity era let brokers act like carriers, and why that's reverting to partnership - How to run an asset carrier and a brokerage together: when to present a united front, when to keep them separate, and how diversifying debt load keeps the balance sheet healthy Time-stamped highlights: - (00:00) Intro and why Harman has a rare both-sides vantage point on the market - (00:46) The Supreme Court broker liability ruling: good for assets, scary for brokerages - (01:26) The spookier part of power-only: not knowing who's actually driving your trailer - (03:44) Why the ruling drives more opportunity to asset-based carriers - (04:01) The fleet: 500 trucks and 2,000 trailers across the western half of the country - (04:55) Why shipper legal teams will push transportation managers toward asset solutions - (05:51) Pass-through liability and why everyone is on the hook together now - (07:13) The dinner-table argument: safety-investing fleets vs. cheap capacity - (08:06) The West Coast example: $1.25 a mile to break even vs. $0.50 from the brokerage - (10:02) Zombie capacity: non-domiciled drivers, unsafe carriers, and the bank fiasco - (10:30) Why banks let upside-down trucks keep running instead of repossessing them - (11:00) Locked into cheap contracts while cheap capacity grabs the high spot loads - (11:13) The "why did you bid this in January?" conversations with customers - (13:34) The ski boat vs. the Titanic: why small carriers can pivot and big ones can't - (14:45) Spot now passing contract, renegotiating in real time, just not fast enough - (15:19) Shippers calling back and why partners who stuck around get first refusal - (17:38) Why more spot volume doesn't mean more money: there just aren't enough trucks - (18:05) The same SoCal-to-Northwest load swinging $4,500 to $7,000 in one week - (18:46) How to quote spot freight in a market that moves hour by hour - (20:14) Why this is nothing like COVID: no hope of capacity coming back - (20:51) The 100% driver turnover problem: a retention issue, not a shortage - (22:18) Playing chess with marbles: trailer pools, dwell time, and the driver who pays - (24:56) CNS Grocers vs. Costco: why an 8-10 hour dock destroys a good load - (26:05) The broken bid feedback loop: why the incumbent carrier has the shortest stick - (29:42) Why brokers became "carriers" on route guides and why that's about to reverse - (33:48) Carrier-first identity and how the combined enterprise sales team works - (36:13) The origin story: trucking in 2006, brokerage in 2009, born out of overflow - (37:43) Diversifying debt load: how the brokerage keeps the asset balance sheet healthy - (45:31) His take on autonomous and electric trucks and when they'll pencil - (49:20) What Harman is most excited about over the next twelve months Guest: Harman Cheema — President & CEO, Cheema Freightlines & Cheema Logistics Harman founded Cheema Freightlines in 2006 and launched Cheema Logistics in 2009 after customers began asking him to cover more freight than his trucks could carry. Today he runs an asset fleet of 500 trucks and 2,000 trailers across the western U.S. alongside a brokerage approaching $100M in revenue, giving him a firsthand read on both sides of every market shift.

Most freight founders start with a plan. Will Hopkins started by getting fired right before Christmas, then spent a year on the carrier side dispatching loads off truck stops before he was legally allowed to broker again. He calls it the best thing that ever happened to his career. Will Hopkins co-founded BlackBox out of his business partner's living room in Birmingham during COVID and has built it into a $70M flatbed brokerage. He grew up in the industry, started at a Roadrunner agency at 19, and along with his partners Logan and William, took the leap into ownership before any of them had ever managed a single employee.  In this conversation, Will breaks down what actually got BlackBox unstuck at the $35-50M plateau, the team system they built to escape the cradle-to-grave trap, and what he's seeing in the flatbed market right now. He also gets into one of the more level-headed reads on the C.H. Robinson Supreme Court case I've heard, why he thinks the small-to-mid-sized broker death narrative is overblown, and the contrarian view that the AI data center boom is a much smaller driver of flatbed demand than the headlines suggest. What you'll learn: Why getting fired was the best thing that ever happened to Will's career and how a year on the carrier side shaped how BlackBox operates todayThe team system BlackBox built to escape cradle-to-grave brokering and the seller-level career path that scales talentHow they got unstuck at the $35-50M plateau by documenting tribal knowledge into institutional processWhy Will believes the flatbed market is tight because of capacity exiting, not data center demandThe discipline of refusing to believe your own market story in good cycles and bad onesHow BlackBox uses Eastern European carrier sales talent and the productivity unlock it createsWhy Will isn't losing sleep over the C.H. Robinson Supreme Court decision and what actually changes for small-to-mid-sized brokersWhat three young founders learned about running a business none of them had ever planned to startTime-stamped highlights: (00:00) Intro and how Will and Jesse have been following each other's content(01:09) Will's take on the C.H. Robinson Supreme Court decision and why BlackBox isn't reacting much(02:23) Why the small-to-mid-sized broker extinction narrative is overblown(05:41) Why freight was always a strange exception on intermediary liability and how that's now resetting(08:30) Documentation, common law, and what "reasonable" carrier vetting will end up meaning(11:09) The insurance math and why Will doesn't see this threatening BlackBox's bottom line(12:50) Mega carriers, road check theater, and why announcing inspections still works(15:51) The record month that meant nothing: average revenue per load went from $2K to $3K, but capacity drove it(17:02) Why flatbed is tighter than van and reefer right now(18:11) The data center myth: only 5% of construction flatbed moves, but feels like 100% because AI is everywhere(21:25) The two-week ceiling on freight market predictions and why Will stopped predicting(22:17) Picking the most useful frame for the market and refusing to believe your own story(25:55) What COVID hiring taught BlackBox about discipline through the cycle(28:15) Hitting the 35-50M plateau and what "what got you here won't get you there" actually meant(29:17) Building the seller-level career path and the team system that broke them out(30:38) Turning tribal knowledge into institutional knowledge across the floor(31:20) Partner Logan's internal tooling: Slack-based load previews, data entry bots, the BlackBox Dash(32:53) Why the pod model beats the pure split model on customer ownership(35:18) Building support around great account managers so they don't burn out(36:31) Hiring green talent vs. plug-and-play recruits and how the freight recession brought BlackBox top operators(37:29) Why Eastern European carrier sales reps have been a game changer(40:16) Carrier ownership inside a pod system and the trade-offs BlackBox accepts(44:24) The metric that separates top carrier reps: loads per carrier, not loads per rep(45:47) The origin story: working at Roadrunner at 19 and the moment three roommates decided to leave(47:25) Logan quitting on the spot, William and Will getting fired, and the non-compete that forced the dispatch detour(47:50) The year dispatching for owner-operators and brand-new authorities(48:09) Starting BlackBox in William's living room with no AC in Birmingham(49:15) What was harder than expected about owning a business at 22(51:54) Three founders, three roles, and the rare stable equilibrium of a founding team without overlap(55:13) What gets Will most excited about the next 12 months and the gap-vs-gain mental modelGuest: Will Hopkins — Co-founder, BlackBox Will co-founded BlackBox with Logan and William in Birmingham, Alabama after the three of them were forced out of a Roadrunner agency before Christmas. They spent a year running a dispatching company through the back end of their non-competes, then launched BlackBox out of a living room during COVID. They've since scaled the company into a $70M flatbed brokerage.

Starting a brokerage from scratch is hard. Starting one at 55, after a 30-year career running brokerage at Schneider, OHL, Redwood, and ITS Logistics, is a different kind of bet — and doing it 18 months before the market collapses into a multi-year freight recession is something else entirely. Greg Sanders has lived all of it. He grew up in the family business, an intermodal company his dad sold to Landstar in 1994. He spent 12 years at Schneider, helped build their brokerage division alongside Aaron Benzeland, and later sold the OHL brokerage to Brad Jacobs as XPO was just getting off the ground. After a run as CEO of ITS Logistics in Reno, Greg launched RDS Capacity Solutions in 2019 — partnered with the original RDS family (his dad's old attorney from the Landstar deal), brought in operators with skin in the game, and built a brokerage that returned all startup capital in six months and was profitable in year one. Then COVID hit, the market ripped, and the 3.5-year slump arrived. In this conversation, Greg breaks down what it actually takes to build a brokerage that survives a cycle like the one we just came through — the partner model, the pod structure, the recruiting playbook he learned from TQL, and why he believes the next three to five years will separate the brokers who integrate AI thoughtfully from the ones who don't. He also gets into his work with the TIA on broker liability, the F4A case in front of the Supreme Court, and what's broken about how FMCSA regulates carriers today. What you'll learn: Why Greg started over at 55 and what made the RDS opportunity different from starting from zeroThe partner model behind RDS: skin in the game, equity ownership, and how Jeremy Inksroom grew his book 5x after joiningWhy the pod structure beats the traditional sales-and-carrier split on a big broker floorHow field generals get paid on contribution margin, not top line — and why that changes everythingWhat Greg learned from Brad Jacobs about M&A execution and why simplicity in the message wins on Wall StreetThe recruiting philosophy he stole from Kerry Byrne at TQL: send the executives to campus, not HRWhy he hires athletes and looks for emotional intelligence over IQHow to integrate AI without alienating the operators who built the businessThe TIA's case on broker liability, the C.H. Robinson Supreme Court case, and what's at stake under F4AWhy FMCSA has failed at carrier regulation and what's driving the chameleon carrier problemTime-stamped highlights: (00:00) Intro: filming live at TIA Capital Ideas, hosted on borrowed Freight Caviar equipment(05:43) Greg's origin story: growing up in the family intermodal business, the two rules his dad set before he could join(07:24) Building the Southern California office for ITCO at 24 years old(08:28) Selling his dad's company to Landstar in 1994 and the Landstar agency model(11:46) Why Greg joined Schneider for "his MBA in trucking" and what he learned about asset operations(13:24) Don Schneider's playbook: deregulation, killing the unions early, doing it first class(17:43) The come-to-Jesus moment when Schneider asked him to move to Green Bay(19:02) Joining OHL, running North American transportation, and learning private equity from the inside(21:22) Selling the OHL brokerage to Brad Jacobs at the very start of XPO(23:24) What stood out about how Brad Jacobs transacts and integrates(25:47) Building the Redwood brand from a collection of acronyms (and why the URL was still available)(28:10) Managed trans vs. brokerage: the trade-offs and why brokerage executes better(32:02) Joining ITS Logistics in Reno, becoming CEO, and getting "sideways with a board member"(34:21) The dynamics of family office ownership and what changes when the board takes over(37:11) Starting RDS Capacity Solutions at 55 — the brand, the asset connection, and the partner setup(41:20) Why Mark Casey and Jeremy Inksroom — and how Jeremy grew his book 5x(42:19) Returning all startup capital in six months and being profitable in year one(43:19) Surviving the 3.5-year freight slump(44:09) Recruiting philosophy: what Greg learned from Kerry Byrne at TQL(46:05) Why he hires athletes and looks for emotional intelligence over IQ(48:59) The pod model: building $PnLs around field generals and paying on contribution margin(51:13) Why traditional sales-and-carrier splits break at scale(56:19) Becoming an expert in an industry, not an equipment type(59:48) Integrating AI without alienating the team — and why this is the next three-to-five-year challenge(01:05:49) Greg's involvement with the TIA and the three legs of advocacy, education, and networking(01:08:13) Broker liability, the C.H. Robinson Supreme Court case, and what F4A protection means(01:11:38) The chameleon carrier problem and how FMCSA has failed to regulate it(01:20:09) What gets Greg fired up: the movement of money, the movement of information, and what the next five years look likeGuest: Greg Sanders — President, RDS Capacity Solutions Greg has spent his career building and leading brokerages, with executive roles at Schneider, OHL (acquired by XPO), Redwood Logistics, and ITS Logistics. He grew up in the family intermodal business his father sold to Landstar in 1994, and launched RDS Capacity Solutions in 2019 in partnership with the founding RDS family. He's been a member of the TIA since 1994 and serves on the board.

Most freight M&A deals look great on paper—but execution is where they succeed or fall apart. So what actually matters when you’re integrating teams, systems, culture, and operations while the market is turning against you?  Jordan Strawn has lived every phase of that journey. He joined Reed Transport Services in 2015 when it was a $70M Tampa-based brokerage and helped scale it to $400M before Werner acquired the business in 2022. As COO through the growth years and now Senior Vice President of Logistics at Werner, Jordan has seen the full arc firsthand: scaling the company, navigating buyer interest, managing diligence, and leading integration on the other side of the deal. In this conversation, Jordan shares what made Reed an attractive acquisition target, how they built with discipline instead of chasing growth for growth’s sake, and what it really takes to make M&A work after the deal closes.  He also breaks down the operational mindset behind successful integration, why process matters more than buzzwords, how Werner structured the business post-acquisition, and why power-only and refrigerated logistics are strategic parts of the company’s broader offering.  What you’ll learn: - Why Reed became an attractive acquisition target: how service quality, repeatable execution, and strength in food & beverage and produce helped make the company stand out - What actually matters in M&A: how leadership teams think through diligence, cultural fit, employee continuity, and post-close execution - How to scale without losing focus: why Reed prioritized lane density, operational discipline, and core competencies over chasing every growth opportunity - What changes after an acquisition: the shift from operating a private business to leading inside a public company environment - Why process is a competitive advantage: how documented workflows, training, accountability, and tech-enabled visibility create operational consistency - How Werner approached integration: aligning teams, structures, and systems while keeping the business moving through a difficult freight market - The role of PowerLink and refrigerated power-only: how Werner’s trailer network creates capacity advantages and sticky carrier relationships - How multi-modal sales structure works: why centralized account ownership supported by mode specialists can improve the customer experience  Time-stamped highlights:- (00:00) Intro: Jordan’s triathlon training, upcoming Olympic race, and Ironman commitment - (03:53) The Reed origin story and how the company grew from its early days into a meaningful brokerage platform - (05:25) Jordan’s transition from UPS Freight into Reed and the move from operations into sales leadership - (06:16) Scaling Reed from $70M to $400M and the philosophy behind that growth - (06:58) The Werner acquisition and what made Reed strategically attractive - (08:22) Why Reed’s food & beverage and produce freight complemented Werner’s existing network - (09:43) Why process matters in both sales and operations - (13:04) What the acquisition process felt like while still running the business day to day - (14:48) Why there was strong buyer interest in Reed and how the team evaluated fit - (16:16) Building for quality, not just top-line growth - (18:45) Reed’s core competency in refrigerated truckload, food & beverage, and produce - (24:28) Jordan’s mindset during the sale and why team continuity mattered - (26:45) The challenge of preserving culture through M&A - (30:30) What actually changes after the deal closes: alignment, process, and decision-making - (32:33) How Werner structured sales and account management post-acquisition - (36:28) PowerLink explained and why power-only matters strategically - (42:08) Expanding into refrigerated power-only with connected reefer technology - (43:55) The building blocks of world-class operations - (48:15) How teams drive compliance through visibility, feedback, and execution discipline - (51:08) What keeps Jordan up at night: constant market change and keeping teams ready to adapt Guest Jordan Strawn — Senior Vice President of Logistics, Werner Enterprises Jordan spent nearly a decade helping scale Reed Transport Services from $70M to $400M before Werner acquired the company in 2022.  He now leads Werner’s PowerLink and truckload brokerage operations, overseeing logistics teams across multiple offices and helping guide the ongoing integration of Reed into Werner’s broader logistics platform. Prior to Reed, he spent years in operations at UPS Freight, where he developed the process-driven mindset that continues to shape his leadership approach today.

How does a 3PL evolve from a collection of entrepreneurial fiefdoms competing against each other to a unified, technology-enabled powerhouse? And what does it actually take to build exceptional operations in an industry where the basics—moving freight from A to B—haven't changed, but everything around it has? Phil Shook has lived through every major transformation in modern freight. He started at Hub Group in 1994 when supply chain wasn't even a college major, joined CH Robinson in 1997 as the 40th employee in the Chicago South office (which ballooned to over 100 in just three years), and spent 23 years watching the company evolve through decentralization, the game-changing American Backhaulers acquisition, and the shift to unified operations. He led intermodal operations for years, managed railroad relationships worth hundreds of millions, and worked closely with the Backhaulers integration team—learning both the "Robinson way" and the scrappier, more tech-forward approach that would reshape the industry. After a stint in equipment leasing staying connected to carriers and railroads, he's now leading North America land transportation at Crowley, building a brokerage business from the ground up with truckload, LTL, intermodal, and dray—what he calls his "dream job" for the last chapter of his career. This conversation is a masterclass in operational excellence and industry evolution. Phil breaks down the intermodal business model most people don't understand, explains why internal competition at pre-2000 CH Robinson sometimes mattered more than external rivals, reveals how the Backhaulers acquisition transformed Robinson's culture and technology, and shares what actually creates sustainable competitive advantage in brokerage (hint: it's relationships, but not the way you think). He also gets into why JB Hunt became the intermodal king, what the railroad business model teaches you about capacity planning, and why great operations teams are built on trust and alignment, not complexity. **What you'll learn** - **The intermodal business model decoded**: How rail + truck combinations work, why anything 700+ miles and within 100 miles of a rail hub can save double-digit percentages, and why JB Hunt's 150,000 container fleet makes them the undisputed leader—plus the nuances that don't show up on spreadsheets (like 80% of volume shipping Thursday-Friday changing your entire cost structure). - **CH Robinson's cultural evolution**: How pre-2000 Robinson operated like franchises where offices competed against each other more than external rivals, why the 2000 American Backhaulers acquisition was "one of the most brilliant things the company ever did," and how Backhaulers' superior technology (the Express system) and individual-level entrepreneurialism reshaped Robinson into what it became. - **Why relationships create operational advantage**: Not the surface-level "does your daughter play soccer" stuff, but how understanding shipper nuances (like discovering a lane's volume all hits Thursday-Friday), building direct relationships with receivers (so late trucks still get unloaded without accessorials), and knowing warehouse schedules lets you solve problems before customers even know they exist. - **The railroad capacity planning challenge**: Why railroads historically struggled with unpredictable volume (not knowing if 100 or 400 containers would show up Chicago to LA), how they've shifted toward airline-style reservation systems to gain predictability, and why they're divesting container ownership to focus on their core competency of moving freight. - **What makes exceptional operations orgs**: Phil's framework—it's not rocket science, it's about building great teams of detail-oriented, results-focused people passionate about being the best, then aligning them around common goals. The 90% that goes well is table stakes; differentiation happens in how you handle the 10% of exceptions through problem-solving, communication, and cost management. - **Why 3PLs won the carve-out battle**: How the industry shifted from "we don't deal with brokers" to Fortune 100 companies deliberately allocating freight to 3PLs—because aggregating the 90%+ of carriers with fewer than 50 trucks into one relationship is more efficient than shippers chasing niche capacity themselves. - **Technology's real role in brokerage**: Where tech genuinely adds value (in-transit visibility ending the "where's my truck?" game, automating unstructured data from emails/faxes into workflows, proactive exception alerts) versus where human relationships and judgment still dominate—and why customers still want to reach a human who understands the consequences of failure. - **The intermodal identity crisis that wasn't**: How 20 years ago intermodal had PR problems, but now most freight that can go intermodal does—and if customers choose truckload pricing, it's a deliberate trade-off for cost certainty and recoverability (because when a train derails in Montana, there's zero recovery optionality). **Time-stamped highlights** - (00:00) From Enterprise Rent-A-Car interviews to Hub Group: Phil's accidental entry into logistics in 1994 when supply chain wasn't a college major - (03:00) Joining CH Robinson in 1997 as the 40th employee in Chicago South—which grew to 100+ in three years - (06:00) The decentralized Robinson model pre-2000: offices acting like franchises, GMs getting profit cuts, and internal competition mattering more than external - (09:00) Creating five regional intermodal operating centers in 2000, then centralizing in 2005 to manage railroad relationships - (12:00) The 2012 shift back to leading operations: getting hands dirty with customers and carriers again - (15:00) Working on the American Backhaulers acquisition and learning "the true brokerage aspect, not just the Robinson way" - (18:00) Intermodal 101: the rail + truck model, why 700+ mile lanes within 100 miles of rail hubs work, and double-digit savings potential - (21:00) Why JB Hunt went all-in on intermodal: Mr. Hunt's visionary BNSF partnership 30+ years ago and how Hunt's now the largest with 150K containers - (24:00) How intermodal works operationally: railroads own some containers (like TripLease), big players own their own fleets, chassis pools - (27:00) The railroad capacity planning problem: not knowing if 100 or 400 containers arrive Chicago-LA, versus airlines' reservation model - (30:00) Why railroads divested container ownership: focusing on core competency of moving freight, reducing cost complexity - (33:00) What share of domestic freight goes intermodal and why more doesn't: customers know about it but choose truckload for cost certainty - (36:00) The types of freight that work for intermodal: retail, F&B, transcontinental from Asia through West Coast, temp-controlled on expedited trains - (39:00) Chicago and Memphis as railroad epicenters where all lines converge; why you might only have one railroad option depending on geography - (42:00) The Backhaulers acquisition impact: their Express system "blew away" Robinson's tech, ultra-entrepreneurial culture at individual rep level - (45:00) The 2010s evolution toward "one team" Robinson: realizing external competition required focusing efforts outward, not fighting internally - (48:00) What creates sustainable success at CH Robinson: Dave Bozeman's turnaround from Wall Street skepticism to "darlings" with 30-40x multiples - (51:00) Building exceptional operations orgs: g...

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...

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/

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/

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/