Beyond Brokerage: Reimagining Freight Jobs in an AI-Powered Future

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 nameEarly pivots, experiments, and lessons from projects that didn’t make itWhy solving unstructured data entry unlocked massive opportunities for brokers and 3PLsThe founders’ decision to build an in-person company in San Francisco and the trade-offs involvedVooma’s core values: hands-on execution, long-term games with long-term people, intellectual honesty, and “run with the ball” ownershipHow AI co-workers will reshape the freight broker role—removing repetitive tasks so humans can focus on strategy, growth, and customer relationshipsWhy building culture, humor, and resilience matters as much as the tech itselfMike 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?Chapters00:00 – 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.