Jay Bregman and the business of a shorter wait

Before Hailo could summon a taxi, it had to persuade taxi drivers to turn on an app that had no passengers. This is an awkward opening proposition. A cabbie has a meter, a working day and plenty of places to be. A stranger with a download link has a theory. Jay Bregman’s solution was to make three London black-cab drivers co-founders. Russell Hall, Gary Jackson and Terry Runham helped recruit their colleagues, one conversation at a time.

It is a useful place to begin with Bregman, whose career can otherwise look like a list of unrelated companies. Parcels, taxis, insurance: the nouns change. The recurring difficulty is getting an existing service to someone who needs it without an expensive stretch of confusion in between. His companies have worked in the gap between the customer’s intention and the moment something actually happens.

The people inside that gap matter. A courier knows the street. A cabbie knows the trade. A photographer knows how long a booking lasts. Bregman’s businesses have depended on turning that knowledge into a product someone will use. The story includes investment rounds and acquisitions, certainly. It also includes a dispatch system with an ordinary first name.

Larry knew where the couriers were

Bregman studied philosophy at Dartmouth, graduating in 2001, and later earned a master’s degree at the London School of Economics in Media & Communications Regulation and Policy. A stint at Harvard’s Berkman Center had put him among law students who wanted to become entrepreneurs. He eventually took that direction himself. London provided the setting, and Tom Allason, a friend he had met at Dartmouth, provided a business partner.

They co-founded eCourier in 2003. Same-day delivery had an information problem: knowing which courier could most sensibly take the next parcel. Handheld computers made it possible to gather locations and assign work in real time. The team built an algorithm called Larry, which took courier positions, traffic and weather into account. A dispatcher with a remarkably undemanding name could now help organize a moving city.

Larry was clever; the finances were less settled. In Bregman’s later account of the 2008 crash, eCourier had signed clients including Harrods, Goldman Sachs and Morgan Stanley. It also discounted heavily and paid couriers by the hour. The business was losing money on each delivery. That admission gives the early success a different texture. More orders could increase the problem as readily as they increased activity.

Then deliveries fell, customers failed and the investment arrangements became uncertain. The financial crisis supplied an education a founder would have preferred to take as an elective. Bregman has returned to that period in his writing because a good operating idea does not protect a company from bad economics or a disappearing source of capital. eCourier survived and was later acquired by Royal Mail. The experience stayed with him.

Six founders, three sets of cab keys

Moving from parcels to passengers was less of a leap than it sounds. Both markets involved someone available in one place and someone needing them in another. Hailo brought Bregman together with business co-founders Ron Zeghibe and Caspar Woolley, alongside Hall, Jackson and Runham. Half the founding team knew the taxi business from the driver’s seat. Their credibility arrived with them.

The drivers’ involvement helped solve the problem that tends to be disguised by the tidy word “marketplace.” Both sides have to appear. A passenger who opens an app and finds no cars is unlikely to wait around for the business model to mature. Recruiting drivers first gave the passenger service something to offer when it opened. Bregman later recalled roughly 3,000 drivers on the platform before launch.

Hailo launched in London in 2011. It was entering a field with several apps already in it. Union Square Ventures, which later invested, described a company that had arrived seventh or eighth yet had signed up half of London’s approximately 23,000 black-cab drivers by the end of 2012. The founding arrangement helps explain why the apparent lateness did not settle the outcome. Access to a community could matter as much as the order of arrival.

There were memorable surroundings, too. Hailo worked aboard HMS President, moored on the Thames. The office address gave a technology company a rather literal relationship with transport. In a 2012 interview, Bregman said he did not own a car or hold a British driving licence. His contribution was organizing journeys, even if he was not personally qualified to take a London fare.

Investors included Accel, Atomico, Wellington Partners, Union Square Ventures and Richard Branson. Yet Hailo’s history also contains a retreat: it pulled out of North America in 2014, the year Bregman departed. The company later agreed to merge with Daimler-owned mytaxi in 2016. Expansion had geographical limits. A method that persuaded London drivers still had to meet the economics and habits of each new city.

Bregman could be direct about the intended destination of a business. Asked in 2012 whether he would consider selling, he answered with four words: “I enter to exit.” The brevity is refreshing. It leaves room for the less glamorous questions that follow: what gets built before the sale, who helps build it, and whether the product continues to be useful after the founder leaves.

A policy as short as the job

After Hailo, drones caught his attention. A meeting with Chris Anderson of 3D Robotics helped turn an interest in programmable aircraft into a commercial pursuit. By early 2015 Bregman was discussing Verifly publicly. The name still pointed toward the sky. The eventual business would turn on something decidedly earthbound: getting the right paperwork before a job could begin.

A drone pilot might need aviation liability cover for a short assignment. The available purchase could require an annual commitment. Bregman and co-founder Eugene Hertz built around the mismatch. Verifly launched its on-demand drone insurance in 2016. The buyer could arrange coverage through a phone, close to the time and place of the work. Insurance could occupy a smaller portion of the day than the work it enabled.

Customers then supplied the next direction. Many pilots were also photographers, contractors or real-estate professionals. They asked about coverage for their other activities. A company built around a flight began following its users into jobs on the ground. That is a more particular account of expansion than the familiar idea of pursuing a bigger market. People who had bought one useful thing were asking for another.

In October 2019, Verifly became Thimble and announced a $22 million Series A led by IAC. Its coverage extended across more than 100 professions, including landscapers, DJs, musicians and dog walkers. The new name offered a small object with a straightforward purpose. A sewing thimble protects you while you work. Bregman discovered that some younger colleagues needed the object explained, an occupational hazard of naming a technology company after something older than a charging cable.

Bregman took the argument to the New York Senate’s Internet and Technology Committee in October 2019. His point was broader than drivers and delivery platforms. Independent work also meant a handyman, cleaner or photographer taking jobs on changing terms. In the figures he presented, 39 percent of Thimble customers were over 50. Flexible work was hardly an invention confined to young people with apps.

For these customers, proof of insurance could be a condition of getting the assignment. Bregman’s ambition was to make the purchase as easy as buying a cinema ticket. That comparison gives the product a useful standard: a person should be able to understand what they are buying and finish the transaction while the opportunity still exists. The insurance remained a serious contract. The buying process could stop behaving like an obstacle course.

“But clarity is always in your control.”

Jay Bregman / on leading through uncertainty

The handover, and the Friday folder

Arch Insurance acquired Thimble in April 2023. At the announcement, Thimble said it had delivered more than 170,000 small-business policies since May 2018. Carrier relationships would continue, and the platform would operate within a larger insurance group. Bregman stayed as President before stepping down in July 2025. Ian Westerman, previously the company’s senior vice president of finance, succeeded him.

Bregman is now founder and CEO of Andel. His public reflections on management still concern the distance between a decision-maker and the work. In 2026 he warned about leaders receiving ever more filtered information as their organizations grow. Reports and dashboards can be useful, but they can also let a manager drift away from what customers, partners and employees actually experience. It is a familiar concern from someone whose first companies depended on knowing where people really were.

His own weekly routine offers a smaller example. On Fridays he reviews the coming week’s meetings and edits presentation materials prepared for them. He also assembles a recap of the week just finished, covering progress, plans and stalled work, and circulates it across the people working with the business. The recap feeds into Monday’s all-hands. Even the founder’s calendar gets its dispatch system.

That folder is a fitting place to leave him. Larry allocated parcels. Hailo connected a waiting passenger with a driver. Thimble let someone fit an insurance purchase around a job. On Friday, Bregman tries to get next week’s decisions into a useful order. The scale has changed repeatedly. The impatience with an avoidable wait has found plenty to do.