Jay Roberts keeps changing the size of the room

The first room was a spare bedroom near Times Square. Jay Roberts was working in real estate investment banking and renting part of his apartment to travelers. People arrived with different accents, different itineraries and a shared willingness to sleep in a stranger’s home. He enjoyed meeting them. He also saw a business problem: the pleasures of an apartment came with rather a lot of suspense.

Would the place resemble the photographs? Would anyone answer a question? Could a group stay together without booking a small collection of hotel rooms? Roberts and his co-founder, Adrian Lam, built Domio around those questions in 2016. A decade later, Roberts is developing waterfront property in Florida and interviewing businesspeople on a podcast called The Long Game. The rooms have grown considerably. So have the commitments attached to them.

A California childhood, a New York education

Roberts was born in Seoul and spent his first three months in an orphanage before an American family adopted him. He grew up in Seal Beach, California. In his account of his childhood, his mother worked as a secretary on less than $30,000 a year, and his half-sister Leslie helped look after him. Those details put some distance between his upbringing and the luxury property market he now inhabits.

He has described feeling different from other children and developing a strong desire to work for himself. In high school, that ambition took a practical form: door-to-door sales. There are quicker ways to discover how frequently people say no, but few that require so much walking. Selling gave him practice in persistence before he had a development site or an investor presentation to offer.

He graduated from the University of California, Santa Barbara with an economics degree in 2007, then earned an MBA at NYU Stern in 2015. At Stern, his interests included finance and real estate. He received the Abraham & Julienne Krasnoff merit scholarship and placed first in the school’s 2013 J.P. Morgan investment banking case competition.

There was also a teaching chapter. At Training The Street, Roberts taught financial modeling and Excel practices to investment banking analysts, including people at Goldman Sachs, Credit Suisse and Evercore. His later work at Bank of America Merrill Lynch put those skills inside institutional real estate transactions. The teams he worked on handled deals including the $1.2 billion MGM Growth Properties IPO and Paramount Group’s $2.6 billion IPO. These were team assignments, with the machinery and responsibilities that description implies.

The spare bedroom becomes a business

His hosting experience supplied a more intimate view of property. A building could be an entry in a financial model. It could also be the setting for someone’s reunion, birthday or first visit to a city. Roberts liked the human encounters. His own travels, which he said had taken him to more than 30 countries by 2018, had exposed him to apartments and hostels with uneven standards.

Domio proposed a recognizable experience across homes and apartment-style hotels. It leased properties, furnished them and rented them for shorter stays. Design, ready-to-use kitchens and guest support would make a group feel settled. The economics depended on paying for the property over a longer period while selling accommodation in shorter increments. A comfortable sofa was useful; so was keeping it occupied.

The group-travel argument was concrete. Friends scattered across several hotel rooms could spend an impressive portion of a holiday arranging to meet downstairs. Domio offered shared space, with the services travelers expected from a hotel. By November 2018, the company said it had hosted more than 80,000 guests. Its planned first apartment-hotel in New Orleans would take the idea from individual homes into a larger building.

“The comfort of a home and the confidence of a hotel.”

Jay Roberts, describing Domio’s proposition in 2018

There were small conveniences behind that promise. Guests could receive instructions before arrival and use mobile-delivered codes for keyless entry. In 2018, Domio announced a $50 million joint venture with Upper90 to fund as many as 25 apartment-style hotels. The plan made the company’s ambition visible: a traveler should know what to expect before opening the door.

Expansion had an address, and a price

Chicago supplied an early demonstration of how Roberts intended to expand. In October 2018, Domio acquired Reserve Rentals, which had 32 units across ten buildings. The initial price was about $1.4 million, with performance-based payments potentially increasing the total to $4.4 million. Founders Grant Hosking and George Savaricas joined Domio’s real estate operation.

That acquisition brought local knowledge as well as inventory. Chicago had its own short-term rental rules, including restrictions on the number of units permitted in a residential building. Every new city introduced another set of conditions. Domio’s average booking then involved five guests, and its median unit had three bedrooms. The product was designed for people arriving together; operating it required negotiating with many parties who did not.

The financing grew too. A $12 million Series A arrived in 2018. In December 2019, Domio announced a $100 million financing package, evenly divided between equity and debt. GGV Capital led the equity financing, while Upper90 led the debt component. The round had closed that August. Its size bought room for expansion; its structure also matters. Borrowing and equity are different commitments, even when a single headline adds them together.

The business brought together disciplines that rarely fit neatly in a startup pitch: property selection, furnishing, distribution, housekeeping and customer service. Roberts’s finance background helped explain his comfort with capital and transactions. Domio still had to deliver the experience, stay within local rules and maintain the confidence of platforms through which guests booked.

The break in the story

In August 2020, Airbnb delisted Domio and reviewed earlier activity. Airbnb later said its examination had found past practices that violated its standards on authentic reviews. Roberts and Lam resigned effective September 20. Roberts also left the board, and finance chief Jim Mrha became interim CEO.

Domio said the activity had ended years earlier. Airbnb reinstated the listings after the leadership changes, removed suspicious reviews and placed the company under a final warning. The sequence matters to Roberts’s biography. His departure came during a dispute over how the company had operated on an essential distribution platform. Describing him simply as a founder who moved on would leave out the circumstances of that move.

More trouble followed after his departure. In November, Domio failed to secure additional capital and moved into an assignment for the benefit of creditors. Mrha disputed reports that the business was closing outright, saying properties remained open during a financial restructuring. The distinction between a struggling company and an instantly vanished one is worth preserving. So is the boundary between Roberts’s tenure and the decisions made afterward.

Florida changes the scale

Roberts’s next company, Prosper Group, initially discussed a different problem: housing supply around Tampa. In an early interview, he described acquiring undervalued assets and adding residential inventory. The company’s stated ambitions included rental and for-sale housing, with possible expansion into Orlando and Central Florida. Its present emphasis on luxury waterfront projects marks a substantial evolution in the business.

He moved to Tampa in 2022 and assembled a downtown city block near Water Street. His account of that period includes driving around sites, meeting brokers and learning the market. He originally intended to flip the assembled property, but rising rates and tighter equity markets complicated that plan. He credits patient investors with giving the deal time. By 2023, he was back in Miami looking for waterfront development sites.

In August 2026, Prosper and Belgium’s Versluys Group closed on a Miami River site for $50 million. The next month, Bugatti announced that the partners would develop its first branded residential project in the United States. The planned tower pairs a familiar luxury name with architecture by Brandon Haw Architecture, interiors by Yabu Pushelberg and residential operations by Rhodium.

The proposal calls for 183 residences across 60 stories, including four penthouses, alongside more than 300 feet of river frontage. Sales are expected to launch in 2027. Those are plans, with construction and delivery still ahead. Prosper reports $2.8 billion in estimated sales value across its pipeline, which includes projects in active sales and pre-development. A pipeline measures intention and work in progress; residents eventually supply a rather more demanding verdict.

A microphone joins the toolkit

Roberts now conducts some of his relationship-building in public. The Long Game features conversations with people including developer Carlos Rosso, entrepreneur Ben Van Leeuwen, broker Fredrik Eklund and technology executive Fred Voccola. Property, hospitality, brands and capital recur across the guest list. The podcast gives him a reason to ask questions and gives listeners a view into the network around his work.

His stated approach to social media includes avoiding ego-driven displays and trying to teach the audience something useful. That is an interesting editorial rule for someone developing luxury real estate, a business hardly short of opportunities for display. It places the emphasis on explaining a transaction, a market or a decision. Whether listeners become partners is a separate commercial question, and one Roberts openly connects to the effort.

Across these chapters, he keeps returning to the relationship between a place and the experience promised inside it. The spare bedroom required a host. Domio required an operating system and reliable conduct. A waterfront tower requires capital, partners and years of execution. Roberts has chosen a title for his podcast that leaves plenty of time for the results to arrive. On the Miami River, the next chapter will have to be built.