Convoy (with CEO Dan Lewis)

The hosts introduce Convoy through a mismatch between the scale of U.S. trucking and the small size of most operators. They cite the episode's figures that one in four trucks is empty, 90% of trucking companies have six or fewer trucks, and 97% have fewer than twenty. In such a fragmented market, an individual driver often has to find the next load alone after finishing a job, even if it is far from the current location. The problem is not simply a lack of trucks or freight, but the difficulty of coordinating them across thousands of small carriers.

Dan describes Convoy as a digital freight network that aggregates small carriers and shippers on one technology platform. Traditional brokers and large asset-based carriers connect the two sides, but each intermediary sees only a small portion of the market. A shared system could learn where trucks are, coordinate routes, improve utilization, and make capacity easier for shippers to find. For drivers, the promise is more convenient work and clearer pay; for the system, the intended result is less empty mileage and waste. These are the company's goals as described by its CEO, not yet evidence in this opening segment that the platform has achieved them at scale.

The hosts position Convoy within a broader generation of companies taking technology developed for consumer markets into older business-to-business industries. They compare the opportunity with Amazon, Airbnb, Uber, and DoorDash, while naming firms applying similar approaches in freight forwarding, oil and gas, and scrap metal. The strategic idea is that mobile interfaces and modern software can change how participants work in industries where relationships and manual coordination have long been central. The comparison establishes a thesis for the episode; each industry still has its own operating constraints.

Lewis's path combines a small-business family background with an early interest in technology. His grandfather began an office-supplies distribution company from a garage, while Lewis taught himself BASIC, built websites, and did IT support. At Yale he studied liberal arts; later, at Oliver Wyman, he worked on logistics and operational projects involving the Panama Canal, airlines, Boeing, parts distribution, maintenance, and procurement. He says that consulting helped him discover a repeatable skill: rapidly understanding unfamiliar spaces and getting new initiatives off the ground.

The conversation complicates the stereotype that consultants remain at the strategy level. Lewis describes a seven-month procurement project in Spain that involved specifying aircraft engine maintenance, working with thirty vendors, and handling financial and operational details. He says that experience gave him an operational grounding, even though he later moved away from hands-on operations in technology roles. The distinction matters for Convoy: understanding a market from analysis is different from building the routines and systems that make it work.

Lewis then recounts how networking became a practical route back into technology. After trying to start a location-based services business, he developed a growing map of people and companies through repeated meetings and eventually joined Skydeck. He later describes tech hiring as unusually skeptical of consultants and explains that persistence, rather than a conventional job application path, helped him find opportunities. The underlying lesson is not that networking guarantees a role, but that his consulting habit of learning a new domain by meeting its participants also helped him enter startups.

Before joining Skydeck, Lewis tried to develop a location-based services business around phone records and social graphs. The venture did not become the company he was pursuing, but the process showed him how information compounds through repeated conversations: after ten or twenty meetings, he understood more about the market and could connect people to new companies. He describes networking as both a route into the startup ecosystem and a method for building a map of an unfamiliar field.