Shows
The Freight ShowBill Driegert (DAT) on the Technology That Actually Sticks in FreightFreight 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...
2025-12-1656 minThe Freight ShowA Masterclass in Scaling Freight: The Tech and M&A Blueprint That Built a $1B+ 3PL BrokerageBuilding a $1B+ multimodal 3PL brokerage in a deregulated, brutally cyclical trucking market doesn’t happen by accident. Doug Waggoner, Chairman & CEO of Echo Global Logistics, walks through one of the most dramatic long-run arcs in transportation — from three-martini LTL sales calls and rolls of quarters for pay phones to cloud-optimized networks, data-driven pricing, and AI as a “task killer, not a job killer.”Doug takes us through the real strategy behind Echo’s rise: building lane density the hard way, turning small acquisitions into consistent growth engines, and developing a managed transportation model with 96%+ renewal rates — al...
2025-12-1058 minThe Freight ShowThe Great Freight Reset: How Smart Data and AI Are Transforming Capacity ForeverFreight market pulse + what’s next. Echo Global Logistics EVP Jay Gustafson breaks down why shippers are consolidating carrier networks, how continuous movement & drop-trailer programs create stability, and where AI + email automation will actually move the needle for brokerages and carriers.We cover market conditions (soft but stable demand, high primary acceptance), the return of annual/biannual RFPs, the 50–250 truck carrier sweet spot, and how top carrier reps are now managing 100+ loads/day thanks to automation and stickier relationships. (FreightWaves)Key Topics & TakeawaysMarket pulse (Q4 2025): Soft/stable demand; high primary acce...
2025-11-1850 min
The FreightCaviar PodcastVooma: Transforming Freight Operations with AIIn this week’s episode of The FreightCaviar Podcast, we sat down with Mike Carter and Jesse Buckingham, Founders at Vooma, an AI automation platform for the logistics and freight industry, designed to act as an "AI agent" for freight brokers and carriers. They bring us behind the scenes of their company, share their take on the future of artificial intelligence, and explain how they're helping transform businesses with it.This week's episode is sponsored by ShipperCRM, Rapido Solutions Group, and GenLogs.Interested in sponsoring our podcast? Send us an email at pbj@freightcaviar.com.
2025-10-281h 02The Freight ShowWhy Most Freight-Tech Projects Fail Before They Even StartRyan Schreiber—Chief Growth Officer at Metafora—joins The Freight Show to unpack why most freight-tech projects fail before they start, how to reframe “the problem” as an operational one, and why a broker’s goal should be zero inbound calls. We dig into AI’s real promise (natural-language workflows at 3 a.m.), the orchestration mindset (people × process × tech), and how to redesign the carrier org around strategic sourcing → advanced booking → coverage instead of asking one rep to do it all.Brought to you byVOOMA — AI agents that help brokers/carriers win and move more fr...
2025-10-2744 minThe Freight ShowWhy Most Brokers Get Freight Pricing Wrong (And How to Fix It)Freight analyst ≠ data analyst. In this deep dive, Chadd Olesen, co-founder & CEO of AVRL, explains why averages lie, how “composition scoring” beats lane-by-lane thinking, and what it really takes to make automated spot bidding profitable at scale. We get tactical on separating cost from margin, building region-first strategies, measuring MAPE, and why speed to quote (sub-second!) wins planners’ attention. We also talk participation rules, when not to bid, and how to use routing-guide gaps to win awards.Brought to you byVOOMA — back-office automation for freight brokerages & 3PLs (AI document h...
2025-10-2147 minThe Freight ShowWho’s Really Hauling Your Freight? Rethinking Freight Security for the Digital EraFreight fraud is evolving — gone are the days of just stolen cargo. Today’s attacks are digital: email hijacks, phone spoofing, “sold MCs,” and identity theft. In this episode, Michael Caney, Chief Commercial Officer at Highway, unveils how fraud works in 2025 and how his team is building the rails to stop it.We dig into:Why fraud attempts spiked 27% in 2024, led by identity theft and inbox compromise Highway’s new Trusted Freight Exchange (TFX)—a secure, identity-verified platform for brokers and carriers Why rate confirmations in email are too risky, and the importance of real-time identity vetting The te...
2025-10-1453 minThe Freight ShowMercedes F1 Champion Nico Rosberg on Winning Under Pressure, Mental Performance & Building Rosberg Ventures2016 Formula One World Champion Nico Rosberg joins The Freight Show to unpack the mindset, mechanics, and team dynamics behind working with / competing with legends like Lewis Hamilton - and how those lessons now power his work as an entrepreneur and investor. We dig into sports psychology, meditation, micro-improvements, F1 team culture, and the insane logistics of moving a global racing circus every week. Nico also shares how he transitioned from the podium to Rosberg Ventures, what he looks for in founders, and why embracing failure compounds growth.What you’ll learnHow tiny ha...
2025-10-0752 min
Check CallSupercharge your Logistics OperationIn this episode, we dive into the world of automation and efficiency. Our guest, Jesse Buckingham, founder of Vooma to break down how to create more efficient processes and integrate AI into an organization. For more information, subscribe to Check Call the newsletter or the podcast. Learn more about your ad choices. Visit megaphone.fm/adchoices
2025-09-2327 min
FreightCastsSupercharge your Logistics OperationIn this episode, we dive into the world of automation and efficiency. Our guest, Jesse Buckingham, founder of Vooma to break down how to create more efficient processes and integrate AI into an organization. For more information, subscribe to Check Call the newsletter or the podcast. Learn more about your ad choices. Visit megaphone.fm/adchoices
2025-09-2327 minThe Freight ShowWhy AI Won't Replace Freight Brokers (And What Actually Will)In this episode, we sit down with Drew Herpich, a freight industry veteran with nearly two decades of experience scaling brokerages and leading carrier sales teams. Drew brings a wealth of knowledge from the trenches, sharing insights on navigating today's challenging market conditions and what it takes to build successful freight operations.Key Topics Discussed:Market Analysis & ForecastingWhy 2024 spot rate predictions missed the mark (forecast: 13-30% growth, reality: ~0%)The flattening of traditional freight cycles and what's driving itHow real-time data and mini-bids are making shippers more nimbleThe shift from annual RFPs to continuous...
2025-09-2342 minThe Freight ShowBootstrapping to $50M: The Power of Reinvestment Over Outside CapitalIn this episode, Ali Shafi, CEO of SIO Logistics, shares insights on bootstrapping a freight brokerage without outside capital. He emphasizes prioritizing company culture over short-term revenue and discusses how AI is increasing load-to-rep ratios. Ali covers early-stage cash flow management, co-founder dynamics, and the benefits of counter-cyclical hiring. He advocates for evaluating tech investments over a 12-month horizon for proper ROI assessment. Throughout, Ali offers practical advice on building a resilient brokerage in today's evolving freight industry.Top takeawaysBootstrapped & disciplined: Reinvest profits; build runway; avoid FOMO spending.Culture > revenue: Hire slow...
2025-09-1539 minThe Freight ShowBeyond Brokerage: Reimagining Freight Jobs in an AI-Powered FutureIn this episode of The Freight Show, Mike and Jesse, co-founders of Vooma, sit down to discuss how a chance introduction between a strategist and a builder evolved into one of logistics’ most exciting automation platforms.From early experiments—including wild ideas like training crows for last-mile delivery—to killing the wrong projects and zeroing in on freight’s biggest bottleneck, unstructured data, this conversation highlights the relentless problem-solving and intellectual honesty behind Vooma’s rise.We cover:The origin story of Vooma, including how a South African slang word became the company nameEarly pivots, ex...
2025-08-1832 minThe Freight ShowHow Shawn McLeod Grew Axle Logistics to $1B: Culture, Sales, and Smart AutomationShawn McLeod, President of Axle Logistics, joins us to share how the Knoxville-based 3PL scaled from $17M to over $1B in revenue. We explore Axle’s “build your empire” culture, their six-week LaunchPad training program, and where they automate without losing the human relationships that drive freight. From hiring and retention to thriving in soft markets, Shawn delivers a playbook any brokerage or ops-heavy business can use.Chapters: 00:00 — The hard lessons of first-time leadership 03:30 — Axle’s trajectory: from ~$17M to $1B+ 07:30 — Culture as strategy: “Build your empire” and loud sales floors 12:00 — Avoiding micro-cultures when scaling offices...
2025-08-1356 minThe Freight ShowFrom Dispatch to President: How ARL Scales Freight with People + AutomationFrom dispatch trainee to president, Jordan Reber unpacks how ARL Logistics scaled an agent-powered network by pairing offshore talent, selective automation, and a revamped cradle-to-grave model—without losing the relationship-first DNA. We dig into building hybrid teams in Colombia, “train-the-trainer” systems, cleaning messy TMS data, and ARL’s shift toward a revenue-engine sales structure.What We CoverCareer arc: Management trainee → dispatch → brokerage launch → ARL presidencyHybrid operating model: Staffing-assisted cradle-to-grave (Colombia ops + US client touch)Train-the-trainer: “Four super users” to eliminate perpetual entry-level retrainingSales structure 2.0: Splitting hunters (sales) and BDR/CS to speed response & enforce SLAsPeople vs process: EOS/Tr...
2025-08-0756 min2025-07-2300 min
Tire Tracks: Driving the Logistics IndustryThe Impact of AI on Freight Procurement: How AI Agents Are Reshaping Logistics Workflows | Episode 57 Episode 57 of Banyan Technology’s Tire Tracks® podcast explores how AI-powered agents are helping Brokers, Forwarders, and Carriers scale their operations and streamline logistics workflows. Jesse Buckingham, Co-Founder of Vooma, explains how these AI agents handle quoting, scheduling, dispatching, and even carrier communication — all while operating within the systems logistics professionals already use. By blending automation with freight expertise, Vooma is helping teams lower cost per load, speed up processes, and boost scalability without extra headcount. Listen to learn:How AI-powered agents improve efficiency across the load lifecycleThe advantages of integrating AI directly into email an...
2025-07-2335 min
The Rental RoundtableRental Roundtable #59: How AI Voice Agents Are Transforming Freight—and What It Means for RentalAI agents aren’t coming—they’re already here.In this episode of Rental Roundtable, we’re joined by Jesse Buckingham, former CEO of Record360 and founder of Vooma, to explore how AI is actively transforming the freight industry, and what that means for the future of rental.Jesse walks us through a live demo of a voice AI agent that can answer calls, qualify carriers, and book freight with zero human involvement. This isn’t a future prediction. It’s already handling thousands of calls a day.
2025-07-0941 min
TransfixSupply Chain Decoded | Feat. Jesse Buckingham, VoomaIn this episode of Supply Chain Decoded, host Jenni Ruiz sits down with Jesse Buckingham, co-founder of Vooma—the platform that’s redefining what it means to scale a freight business with AI. Jesse’s no stranger to the logistics industry, having previously led companies like Trucker Tools and Record360. Now, he’s building AI agents that slot directly into the workflows of logistics teams, taking on the tedious, repetitive tasks that slow brokers down.
Jesse shares the vision behind Vooma’s orchestration platform, why their "launch week" strategy took the industry by storm, and how AI agents are being personifie...
2025-06-2540 min
Let’s Talk LogisticsLet's Talk Logistics with Jesse BuckinghamJesse Buckingham, helped sell Trucker Tools and ran private equity-backed freight tech—now he’s building AI agents to kill the busywork in brokerage. We get into why scaling with headcount is dead, how mid-size brokers can punch above their weight, and what AI actually means for freight.
Key Chapters:
(0:00) Introduction and Background
(1:02) Founding and Early Days of Vooma
(7:29) Agent AI and Its Impact
(13:04) AI in Logistics and Brokerage
(16:30) Future of AI in the Industry
(21:35) Opportunities for Mid-Market Brokers
(26:20) Challenges in Truckload Brokerage
(26:35) Future Plans for Vooma
(27:45) Jess...
2025-04-1049 min
Venture with GraceHOF Capital Partner Hansae Catlett: Early-Stage AI & Dev Tools InvestingHansae Catlett is a Partner at HOF Capital where he invests across sectors and stages, with a particular focus on leading the firm's early stage investment strategy in applied AI, B2B application software (horizontal and vertical), dev tools & infra, and deep tech.Prior to joining HOF Capital, Hansae was a Vice President at Bessemer Venture Partners, helping to lead the firm's investments in cloud and AI. His investments and/or board positions included Guild, Jasper, Luxury Presence, MaintainX, Nala, Productboard, Rilla, ServiceTitan, Sila, Shopmonkey, Spot AI, TRM Labs, and VendorPM. He also supported Bessemer's investments in Canva, EvenUp...
2025-02-121h 03
The Freight PodEp. #48: Jesse Buckingham, CEO and Cofounder of VoomaIn this episode, Andrew is joined by Jesse Buckingham, CEO and cofounder of Vooma. Jesse studied law and economics at the University of Sydney and got his MBA from Stanford. Before Vooma, he was CEO at ASG LogisTech, whose businesses included Trucker Tools, Record360, e-Courier, and PackageRoute. He was also a consultant at Bain & Company.Now, Jesse’s leading the Vooma team in building AI tools that will automate the shipment lifecycle and help brokerage teams enhance productivity and reduce opex. Vooma recently raised $13M in Series A funding led by Craft Ventures, on top of a $3.6M...
2025-01-011h 37
FreightCastsWHAT THE TRUCK?!? EP785 Kal Freight’s fraud allegations; Make-A-Wish convoys; Vooma’s $13M Series AOn Episode 785 of WHAT THE TRUCK?!?, Dooner is talking about the latest scandal to hit freight. Daimler Truck Financial Services USA LLC, the company’s largest vehicle finance lender, says it has uncovered evidence of massive fraud perpetrated by Kal Freight against its creditors. Now, Daimler alleges that Kal Freight fraudulently obtained approximately $16.9 million to purchase 164 trailers from Vanguard. The Mother’s Day Truck Convoy began over 30 years ago, inspired by wish kid Matt Strausser’s dream to ride in a big rig and talk to his sister on a CB radio. Starting with just a...
2024-12-1645 min
WHAT THE TRUCK?!?Kal Freight’s fraud allegations; Make-A-Wish convoys; Vooma’s $13M Series A | WHAT THE TRUCK?!?On Episode 785 of WHAT THE TRUCK?!?, Dooner is talking about the latest scandal to hit freight. Daimler Truck Financial Services USA LLC, the company’s largest vehicle finance lender, says it has uncovered evidence of massive fraud perpetrated by Kal Freight against its creditors. Now, Daimler alleges that Kal Freight fraudulently obtained approximately $16.9 million to purchase 164 trailers from Vanguard. The Mother’s Day Truck Convoy began over 30 years ago, inspired by wish kid Matt Strausser’s dream to ride in a big rig and talk to his sister on a CB radio. Starting with just a...
2024-12-1645 min
The Bearhug Experience(Funding Recap #35) Bearhug Recruiting's Early & Growth Stage Tech Startup Funding Recap! 12/9/24Here’s this week’s startup funding recap ($478.42 million raised across 11 featured companies):
1. AMP, led by Matanya Horowitz, has raised $91 million in a Series D funding round. AMP provides AI-powered sortation systems for the waste and recycling industry, using deep learning to identify recyclables and contaminants in real-time.
2. Heirloom, led by Shashank Samala, has raised $150 million in a Series B funding round. Heirloom develops Direct Air Capture (DAC) technology that uses enhanced limestone to capture CO2 directly from the atmosphere.
3. Tractian, led by Igor Mari...
2024-12-1415 min
The Freight Coach Podcast1087. #TFCP - Utilizing Multi-Channel AI To Scale In Logistics!Let’s dive into the last episode of this week with a returning guest, Jesse Buckingham, talking about the evolving technology in the transportation business! Today, Jesse presents Vooma’s vision to streamline logistics by reducing manual tasks, the critical role of speed and efficiency in freight brokerage, valuable startup insights, and rapid AI advancements! About Jesse Buckingham Jesse is a founder of Vooma, an automation platform for freight brokers and carriers that automates email quoting and load building using AI. Vooma has been adopted by leading brokers like Echi, MODE and A...
2024-12-0630 min
The Freight Coach Podcast935. Jesse BuckinghamGet tons of value from today's episode with Jesse Buckingham! Jesse talks about his journey into the transportation industry, his background in logistics technology, raising capital, and building relationships for long-term success in the trucking business! About Jesse Buckingham Jesse is a founder of Vooma, an automation platform for freight brokers and carriers that automates email quoting and load building using AI. Before Vooma, Jesse was the CEO of a logistics software company that sold to brokers, carriers and fleet owners that he grew from $2M to $20M+ ARR. Previously Jesse was a s...
2024-05-2846 min
House Life (How's Life)The life of a passionate amateur dancerYour hosts: Emma Brooks, Jake Zuidveen, Patricie BendovaIn this episode we talk about the life of a passionate amateur dancer. How do we, as people with full time jobs, still make time for dance, practice, teaching, events etc. It's not easy but we are committed to the cause. Want to share feedback with us? Email houselife_ams@outlook.comFind us on Instagram: https://www.instagram.com/house.dance.amsterdam/Find us on Facebook: https://www.facebook.com/AmsterdamHouseDanceCommunityOur favourite tracks:Jake: Vooma...
2023-02-201h 19