In 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 name
• Early pivots, experiments, and lessons from projects that didn’t make it
• Why solving unstructured data entry unlocked massive opportunities for brokers and 3PLs
• The founders’ decision to build an in-person company in San Francisco and the trade-offs involved
• Vooma’s core values: hands-on execution, long-term games with long-term people, intellectual honesty, and “run with the ball” ownership
• How AI co-workers will reshape the freight broker role—removing repetitive tasks so humans can focus on strategy, growth, and customer relationships
• Why building culture, humor, and resilience matters as much as the tech itself

Mike and Jesse also share the books that shaped their thinking—from The Mom Test to Thinking, Fast and Slow—and even tackle the ultimate startup question: Would you rather fight one horse-sized duck, or a hundred duck-sized horses?

Chapters

• 00:00 – Welcome & Introduction
  Setting the stage for how AI and automation are reshaping freight.
• 00:34 – Meet Mike & Jesse
  The chance introduction that led to founding Vooma.
• 02:00 – Early Impressions & Complementary Skills
  Why their different strengths made them better together.
• 04:30 – Crazy Early Experiments
  From training crows to robotic last-mile delivery—what worked, what didn’t.
• 07:00 – Killing the Wrong Projects
  Lessons from pivots and finding the right entry point.
• 08:00 – The Origin of “Vooma”
  How a South African slang word shaped the brand.
• 09:00 – Discovering the Real Bottleneck
  Why unstructured data entry was freight’s hidden pain point.
• 13:00 – The Future of Freight Brokers
  AI co-workers, strategy over grunt work, and what brokerages look like in 5 years.
• 17:00 – Scaling With AI Agents
  Optimizing workflows, market visibility, and clearing inefficiencies.
• 18:30 – Why Build In-Person in San Francisco
  Trade-offs of geography, networks, and startup speed.
• 20:00 – Vooma’s Core Values
  Hands-on execution, long-term games, intellectual honesty, and “run with the ball.”
• 24:50 – Culture & Humor in the Trenches
  Why resilience and laughter matter in startups.
• 25:30 – Deep Dive Interviews
  How Vooma’s unique hiring process uncovers true values and fit.
• 27:30 – Books That Shaped the Founders
  From The Mom Test to Atlas Shrugged to Thinking, Fast and Slow.
• 30:00 – The Final Question
  One horse-sized duck vs. a hundred duck-sized horses—co-founder answers revealed.

Shawn 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
16:30 — Hiring at pace: signals that actually matter
22:00 — Training at scale: LaunchPad’s six-week ramp
27:30 — Retention: base vs. commission, fairness, and grind
34:00 — Where to automate first (repeat touches, doc QA, quoting)
41:30 — Keeping the human: when relationships beat automation
47:00 — Surviving soft markets: travel > excuses
52:30 — Leadership evolution and feedback loops

Key Takeaways:

• Culture is Axle’s #1 growth strategy — lose that, and you lose everything.
• LaunchPad’s six-week program speeds ramp time and improves throughput.
• Automate repetitive touches (document checks, quoting) but never the relationship.
• In down markets, Axle increases customer travel rather than cutting it.
• Hiring focuses on energy, work history, and coachability — not just interview polish.

Memorable Quotes:

• “Culture is number one in the strategy for growth.”
• “Automate the repetitive; never automate the relationship.”
• “Travel is the last thing you cut in a soft market.”

Links & Resources:

• Shawn McLeod — LinkedIn
• Axle Logistics — Website

Sponsor:
This episode is brought to you by Vooma — AI that unlocks revenue in your team’s inbox with automated quoting, order entry, tracking, and more. Learn more at Vooma.com.

From 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 Cover

• Career arc: Management trainee → dispatch → brokerage launch → ARL presidency
• Hybrid operating model: Staffing-assisted cradle-to-grave (Colombia ops + US client touch)
• Train-the-trainer: “Four super users” to eliminate perpetual entry-level retraining
• Sales structure 2.0: Splitting hunters (sales) and BDR/CS to speed response & enforce SLAs
• People vs process: EOS/Traction, shadow-work, and deleting steps before automating
• Tech partnerships: Why ARL co-builds with vendors and aims for 80/20, not edge cases
• Automation lens: Start with mundane, API/RPA bridges, humans as exception managers
• Data reality: TM3→TM4 migration, standardizing inputs, and the prize of drayage pricing data
• Risk & resilience: Receivables caution, tariffs, and modal shifts (intermodal ↔ OTR)
• Culture: Small wins daily, continuous training, and giving offshore teams a real voice

Playbook & Tactics

• Sit tech next to the business. Proximity shrinks build cycles and bakes in reality.
• Free reps to sell. Move load-building, T&T, and intake to an ops pod first—then automate.
• Design for exceptions. Automate 6–7 steps in a 10-step flow; humans handle the rest.
• Standardize input fields. Clean data starts at the source; train against exceptions.
• Measure the ROI. Track time saved, licenses retired, and throughput per seat.
• Organize for strengths. Separate “people-first closers” from “process-first executors.”

Notable Quotes

• “If the tech people would just sit next to the business people, you build product fast.”
• “Train four super users and you never have to train entry-level again.”
• “Those are two different roles—very few are great at both.”
• “Our motto is small wins every day.”

Resources Mentioned

• ARL Logistics (brokerage & agent network)
• US1 Industries (parent; proprietary TMS)
• Lean Solutions Group (nearshore ops)
• EOS / Traction (operating system)
• The Revenue Engine by Kara Brown (sales/marketing alignment)

Sponsor

Vooma — Back-office automation for freight brokerages. From AI document handling to ops streamlining, scale without the growing pains.