Drew McElroy’s problem with the empty truck

Drew McElroy once offered truckers a simple bargain: download the app, throw a baseball, and try to drop him into a dunk tank. At the Great American Trucking Show, the future of freight brokerage briefly involved a founder getting wet. There were also beer and pork chops for people willing to spare ten minutes. It was an unusually literal way to put yourself at the mercy of your customers.

The spectacle suited the problem. Transfix needed drivers to join its freight network. Drivers needed a reason to bother. A software demonstration could explain the product; a dunk tank could at least earn the demonstration a hearing. McElroy’s account of those early sales efforts carries a useful warning for anyone enchanted by the word marketplace: somebody has to persuade the first people to turn up.

The spare bedroom education

McElroy had been learning how to do that since childhood. His parents ran a freight brokerage from a spare bedroom in Milltown, New Jersey. At twelve, he helped with the phones. The work involved matching companies with goods to move to truck owners able to move them. An empty trailer might look like nothing much. To a broker, it was an opportunity that somebody had failed to arrange.

One lesson concerned the first question on a call. Listening to his father speak to drivers, McElroy noticed that he began by asking about their day. The whereabouts of the truck could wait. Years later, McElroy would remember that habit as instruction in treating drivers as people, rather than components in a shipment. It is a modest detail, and an unusually revealing one in a business so often described through machines.

“How was your day?”

The question McElroy remembers his father asking drivers first

There was another family story, less solemn. His father had started a carrier called Andrew’s Express in the late 1970s and joked that it was named after Drew. McElroy pointed out the chronological inconvenience: the trucking company had arrived before he did. The family later built Priority Distribution Inc., known as PDI. Freight was both the family livelihood and the subject on which a younger generation could develop opinions.

He studied at Georgetown’s McDonough School of Business, earning a BS in Management and International Business, and undertook further study at the University of Melbourne. Back at PDI, he led business development between 2004 and 2011 and eventually became president. During that period, the company’s annual revenue more than tripled. He had experience selling logistics before he tried selling investors on a logistics startup.

A truck can be busy losing money

What bothered him was the waste embedded in ordinary work. A driver could finish a delivery, drive empty toward another pickup, and spend more time finding the next job. Inside the brokerage, people could expend their own hours assembling the transaction. McElroy described those three problems together: empty movement, searching, and processing. A truck moving down the road was an unreliable measure of how productively its day was going.

Early Transfix let drivers see loads prioritized by location, book at an offered price or make a counterbid. Tracking made it possible to flag delays and contact the people affected. These were practical interventions in a day full of small uncertainties. The point was to make the next useful action easier to see, then reduce the work required to arrange it.

Getting that idea understood required its own transport operation. McElroy took his knowledge west, spending time on friends’ couches in Silicon Valley while learning about startup building and fundraising. He knew logistics; venture capital, technical teams, and the expectations around a software company required another education. He sought out people who understood the parts he had yet to learn.

A changed LinkedIn title helped bring the business forward faster than expected. In his retelling, a potential customer called soon after he identified himself as the new company’s CEO. The opportunity involved Barnes & Noble and a request to start the following week. The product was still being built. Customers, inconveniently for a tidy launch schedule, had freight to move already.

Two kinds of knowledge, one argument

McElroy and Jonathan Salama founded Transfix in 2013. Salama brought engineering experience, including work at Gilt Groupe. Their pairing gave the company two different ways to look at the same job: the freight operator’s familiarity with what happens on a difficult shipment, and the engineer’s ability to make a repeatable system. Neither kind of knowledge automatically supplied the other.

In 2019, McElroy described choosing New York deliberately for access to software and quantitative talent. He wanted freight specialists and technology specialists working through problems together. His description of the process was cheerfully argumentative: put the groups in a room and make them debate. The disagreement mattered because an elegant software answer still had to survive a load that needed covering.

He also had to explain the business to people who had never worked in it. Early investors learned about empty return journeys and the phones, faxes, and bulletin boards used to coordinate freight. The founders made an unfamiliar industry legible through its daily absurdities. An investor did not need a childhood in a brokerage to understand paying for a truck to return empty.

By 2017, Transfix was competing in a crowded field routinely called “Uber for trucking.” McElroy argued that the company’s advantage depended on seeing more of the truckload supply chain. The comparison with a consumer app made a convenient introduction. The commercial argument involved a messier question: how much of a customer’s actual freight work could the system understand and handle?

The price on the quote leaves things out

A 2019 conversation with Anheuser-Busch’s Mark Young gives that argument some texture. Young described moving beyond an inward, price-focused view of transportation toward a fuller account of operating costs. McElroy talked about assigning costs to decisions around waiting, appointments, and contract or spot freight. A low quoted rate could be a poor guide to what the operation actually consumed.

Matching several trucks with several loads opened possibilities that a single transaction could conceal. So did knowing when a driver was falling behind before a missed appointment became a surprise. The attraction was partly better execution and partly better information for the next decision. Here was McElroy’s preference for efficiency expressed in the unromantic language of appointment times.

Recognition followed. Transfix appeared on Forbes’ 2018 list of Next Billion-Dollar Startups. In June 2019, EY named McElroy among its New York Entrepreneur Of The Year award winners. Those distinctions marked the distance from the family brokerage. They also placed him in a different kind of company, among founders expected to turn an operating insight into a business that could keep growing.

Changing his own job

In March 2020, McElroy handed the CEO role to Lily Shen and became chairman. His explanation was unusually direct. The company had grown more complicated, and he believed Shen was better equipped to run it. He wanted to keep working on strategy and the longer view. The management team developed the succession plan and took it to the board and investors.

McElroy described using the period between Christmas and New Year’s for an annual retrospective. That habit made room for a question founders can be tempted to postpone: which job should I actually be doing? His answer included some personal turmoil, he acknowledged, but also confidence in Shen. He could remain committed to the business while giving someone else responsibility for its daily operation.

“I think Lily can do it better.”

Drew McElroy, on the 2020 CEO handover

The company’s route onward proved uneven. A proposed public listing through G Squared Ascend I was called off in October 2022, with the companies citing public-market conditions. Private financing would support the next stage. Salama became CEO in March 2023, succeeding Shen. McElroy remained chairman as the enterprise he had helped create worked through another change of direction.

The former competitors become customers

In June 2024, NFI bought Transfix’s freight brokerage operation. Transfix kept its technology and concentrated on software and data solutions. NFI became the first outside customer for its transportation management system. The company buying the operation would use the system that had helped run it. For McElroy, the sale opened a way to offer years of development to other brokers.

That shift also changed the sales conversation. Buying software from a company competing for the same shipments carries an obvious awkwardness. Selling the brokerage removed that particular entanglement. The former rival could approach other brokers with operating tools. McElroy’s family background now supplied a connection with the people on the other side of the sales call.

In a March 2026 interview, he described the brokerage as the place where the software had been developed through real work. Engineers had covered loads themselves. He also spoke about small brokerage businesses whose owners and loyal teams had much of their lives invested in them. His concern was that a widening technology gap would leave those companies exposed. He wanted the tools to be available to them.

There is a pleasing continuity between that ambition and the spare bedroom. McElroy learned early that freight work depended on people making arrangements with other people. He has spent his career trying to reduce the waste around those arrangements. The software has changed, the customers have changed, and his own title has changed. His father’s opening question still seems like a sensible place to begin.