Jeff Cavins sold his house. Then he built a business around the open road.

Jeff Cavins and Jen Young sold their houses and bought a trailer. In the usual telling of a successful executive’s life, this is where the retirement chapter begins. For them, it was product research. Their Airstream, an Eddie Bauer edition they called Eddie, became a home, an office and a rather effective excuse to ask strangers how they spent their holidays.

They were looking for a business they would enjoy inhabiting. Cavins had already spent years in software, communications and digital media. Young came from advertising and marketing. In January 2014, sitting through company updates in a conference room, they exchanged a look and began considering a different working life. The outdoors was essential to the idea. The exact business still needed discovering.

By June 2026, the venture that grew from those conversations had acquired a name broad enough to accommodate its ambitions: The Ride Platform. Cavins, its co-founder and CEO, was now talking about car fleets, insurance and autonomous vehicles. The route from Eddie to that announcement is worth following. It explains why a founder who wanted fewer walls around him ended up building so much of the machinery behind other people’s businesses.

The domain cost $15.98. The commitment cost two houses.

The first name was Outdoorsy. Cavins liked its suggestion of adventure; the available domain, at $15.98, had the additional charm of being affordable. In his account of the founding, the couple invested their life savings in the autumn of 2014. They bought a GMC Denali to tow the Airstream and started traveling, meeting RV owners and prospective renters along the way.

There is something pleasantly practical about this beginning. They wanted to understand a holiday business, so they went where people were actually taking holidays. The research involved knocking on camper doors, sitting with owners and hearing about the pleasures and inconveniences of taking a home on the road. A campsite offers fewer opportunities to hide behind a presentation than a conference room does.

Young’s own early account gives Eddie a supporting role with considerable personality. They had considered a conventional motorhome before choosing a truck and travel trailer. Their working year included time in San Francisco and stretches traveling through the Northern California coast and Southern states. Business travel and home life became unusually difficult to separate when both required the same tow hitch.

Before the campground, the broadcast booth

Cavins brought a long technology career to this apparently unlikely market. His early work included nearly a decade in Sony’s broadcast division, in engineering and sales management. He later founded and led CSI Digital, which developed visual technology for television and film. Those jobs placed him close to customers whose equipment had to work when the programme, the production or the game demanded it.

His subsequent roles included senior vice president at Exodus Communications and chief executive at Loudeye, CallWave and Fuze. Digital media distribution, internet infrastructure and communications software may seem distant from a campervan key exchange. Each involves getting a complicated system to behave simply enough for somebody else to use it. That is a useful connection across an otherwise restless-looking résumé.

At Loudeye, his work included international expansion and partnerships with large technology and media businesses. At Fuze, the product story reached the iPad: the company’s software appeared in Apple’s 2011 advertising. Cavins’s connection to Steve Jobs remains part of his own account of how he learned to think about customers. The advice he says he carried forward was to understand their needs closely.

These were established executive credentials to bring to an RV startup. They also make his willingness to start again more interesting. He knew the vocabulary of big-company partnerships and public markets. He still went to campgrounds. Experience had given him contacts and a working method; it had not supplied the answers to how a private owner would feel about handing over the keys.

Jen Young, Eddie and the people with the keys

Cavins and Young met in 2013 while he was advising a technology company and she was consulting there. Their partnership joined his software background to her experience in marketing. It also rested on a shared enthusiasm for being near mountains and water. The business they chose gave both of them a reason to keep doing what had drawn them away from their desks.

Outdoorsy launched its platform in 2015 with a small remote team. Referrals and an early video helped introduce it to customers. The proposition was straightforward: owners could offer their vehicles to travelers who wanted a road trip without buying an RV. The work underneath included customer service and making the exchange between owner and renter easier to manage.

They continued using the product’s way of life themselves. In 2020, the couple took a seven-week journey from Austin through Texas, New Mexico, Utah, Colorado and Montana in a Winnebago Revel. For a founder selling access to the outdoors, that is useful proximity to the subject. It also makes a better photograph than another executive standing beside a company sign.

“I’m actually an engineer at heart.”

Jeff Cavins

A rental booking comes with paperwork

The postcard version of an RV marketplace contains open roads, mountain views and perhaps a dog enjoying an unreasonable amount of window. Its working life contains insurance. Cavins’s expanding business followed the practical obstacles that appeared between a vehicle owner and a paying customer. Helping people meet was one job. Helping them operate reliably required more tools.

Roamly became the insurance business within the group, while Wheelbase provided software for rental operators. The distinction matters to understanding Cavins’s career: the company grew into activities that an ordinary traveler might barely notice. A holiday booking depends on arrangements that remain invisible when they work. Fleet owners, however, have to think about those arrangements every day.

In July 2025, Roamly announced its appointment as a Lloyd’s Coverholder, giving it delegated underwriting authority for policies backed by the Lloyd’s market. This was a concrete step in Cavins’s effort to extend the insurance business into more forms of shared mobility. It connected the group’s software ambitions with the specialist underwriting relationships needed to support them.

The following month, Roamly introduced its Carshare insurance platform. Its announcement described coverage integrated into Wheelbase, allowing operators to take bookings through their own branded websites as well as outside marketplaces. It reported 7,000 vehicles covered nationwide at that point. Cavins’s case for the product was rooted in a familiar operator complaint: insurance could become an obstacle to expansion.

When the name stopped fitting

On June 17, 2026, Cavins announced that Outdoorsy Group was becoming The Ride Platform. Outdoorsy remained the RV marketplace brand. The parent’s new name accommodated Ride, its professional car-rental marketplace, alongside Roamly and Wheelbase. A business once described by the type of vehicle on its website was describing itself by the work it performed for operators.

The scale was also different. In that announcement, Cavins reported more than $4 billion in transactions across 4,800 cities and 11 countries, together with more than three years of profitability. Those are the company’s figures, dated to the announcement. They describe transactions passing through the businesses, rather than Cavins’s personal wealth or the group’s revenue.

His next ambition reaches into autonomous mobility. He argues that people operating those vehicles will need the same combination of demand, management software and suitable insurance. The premise carries his earlier RV experience into a different market: a useful vehicle becomes a workable business only when someone can manage its bookings, costs and daily operation.

By July 2026, Roamly had announced a London commercial and underwriting office and appointed former Bolt insurance executive Dan Severin to lead global mobility insurance. That expansion added people and underwriting capacity to the proposition. It is a less cinematic development than a driverless car, but an international mobility business requires rather more than an interesting vehicle.

The customer still gets a vote

Cavins has collected recognition along the way, including selection among Goldman Sachs’s Most Exceptional Entrepreneurs of 2022. In 2023, Outdoorsy placed fourth in Fast Company’s Travel and Hospitality innovation category. Such acknowledgments belong in the record. The more revealing detail may be that his latest corporate identity still depends on the questions that sent him onto the road.

His public conversations now range across robotaxis, fleet economics and the future of cities. On Austin Next in August 2025, he discussed how autonomous vehicles might fit into marketplaces and insurance. The scope has widened considerably since Eddie. The recurring interest is the person trying to earn money from a vehicle, and the practical arrangements that person needs.

A founder can acquire a larger vocabulary without losing the original question. Cavins and Young began by asking how they could build a business around a life they wanted to live. They found themselves listening to people who already owned the keys. The Ride Platform gives that habit a broader territory. For all the talk of vehicles driving themselves, somebody still has to knock on the customer’s door.