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.