Key Takeaways:
- The finance-to-hospitality pivot: Seidman spent years at Goldman Sachs, Credit Suisse and a luxury developer overseeing $3.5 billion in projects before deciding he’d rather save abandoned 1950s motels than finance another glass tower
- The $22.5 million orphanage: When Seidman transformed a crumbling 1864 New Orleans asylum into Hotel Saint Vincent, it landed on Travel + Leisure’s list of the world’s 500 best hotels – proof that historic preservation and commercial success aren’t mutually exclusive
- The hotelier who calls big chains “fauxtique”: With 11 boutique properties and a philosophy that “there’s no such thing as a great vibe at a big hotel,” Seidman has become one of America’s sharpest critics of corporate hospitality’s attempts to copy his playbook
Most hoteliers build their careers acquiring sites in predictable markets. Jayson Seidman builds his by finding the buildings everyone else wants to demolish.
A 1956 motel on an industrial stretch of Tulane Avenue that operated as a by-the-hour establishment. A 19th-century orphanage built during yellow fever epidemics. A 1948 motor court in San Antonio overrun by vagrants. These aren’t properties that appear in investment banking pitch decks. They’re the kind of buildings that get razed for parking lots.
Seidman sees something else entirely.
The banker who got restless
According to multiple industry sources, Seidman’s path to hospitality was anything but direct. Born in Mobile, raised in Houston, he graduated from Tulane University in 2001 and was recruited by a Goldman Sachs technology startup. When that folded, he moved into real estate analysis – first in New York and Dallas, then Miami for private equity work.
The jobs paid well. The buildings bored him.
“It’s a lot more exciting than an office building or multifamily property,” Seidman later told Tulane’s alumni publication about his eventual pivot to hotels. “I finally had a platform where I could channel my passion for travel, fashion, music and design, while utilising both sides of my brain.”
He enrolled at Columbia University’s Graduate School of Architecture, Planning and Preservation, then completed a master’s in real estate finance at NYU. By 2007, he’d founded Sandstone. But the real education came during his final corporate role: Head of Development at SHVO, a luxury real estate developer in New York, where he oversaw more than $3.5 billion in high-end projects over three years.
“It got to a point where I thought, you know what, it’s time to just slow down,” Seidman later reflected. “I felt like it was the general trend in society that we were all kind of becoming carbon copies of each other.”
He went looking for places that weren’t copies of anything.
The motel that changed everything
Walking along Tulane Avenue in New Orleans around 2016, Seidman found the Rose Inn Motel – a decrepit 1956 motor lodge with popcorn ceilings, smoke-stained carpets, and a reputation for hourly rentals. The building had the bones of mid-century modernism buried under decades of neglect.
According to industry accounts, Seidman partnered with developers Zach Kupperman and Alex Ramirez. They hired Nicole Cota Studio for interiors and Costa Rican landscape firm VIDA Design Studio. The renovation had to work within historic tax credit requirements – which meant preserving elements down to the painted stripes on the parking lot.
The Drifter Hotel opened in 2017. Twenty rooms. Trowelled concrete walls. Oaxacan tiles. A saltwater pool with a cantilevered disco ball. Rates that seemed audacious for a former hourly motel on an industrial corridor.
It worked. Architectural Digest named it one of America’s chicest motels. The project won the 2018 Louisiana Landmarks Society Award for Excellence in Historic Preservation. More importantly, it proved Seidman’s thesis: there was demand for design-driven hotels that celebrated their past rather than erasing it.
“I wanted to breathe life back into the property in a way that didn’t feel like a mid-century modern relic,” Seidman told Yatzer, “but a piece of history that’s continued to thrive through subsequent decades.”
The orphanage on Magazine Street
The success of The Drifter led to something far more ambitious. On Magazine Street in New Orleans’ Lower Garden District sat a five-building campus that had served as St Vincent’s Infant Asylum since 1864. Built during yellow fever epidemics that killed nearly half of those infected, funded by Irish immigrant philanthropist Margaret Haughery, the property had languished for decades – briefly converted to a low-budget hostel, then left to deteriorate.
According to Engineering News-Record, Seidman and partner Zach Kupperman invested $22.5 million to transform it into Hotel Saint Vincent. The restoration required repairing 150-year-old masonry, converting 12,000 square feet of exterior corridors into private verandas, and navigating historic preservation requirements that involved 50 to 75 professionals before construction even began.
The 75-room hotel opened in 2021. It preserved the Virgin Mary grotto in the courtyard, a gargoyle atop the clock tower, and a marble header inscribed with “St. Vincent’s Infant Asylum” at the entrance. Designers Liz Lambert and Larry McGuire layered 1960s and 70s Italian modernism over the Victorian bones.
Hotel Saint Vincent has since appeared on Travel + Leisure’s list of the world’s 500 best hotels and won an ABC National Eagle Award as the nation’s top historic restoration.
“There’s no such thing as a great vibe at a big hotel”
By late 2024, Sandstone’s portfolio had grown to 11 properties across Texas, Louisiana, and New York – including the Columns Hotel (an 1883 mansion on St Charles Avenue), the Thunderbird in Marfa (reimagined by Lake Flato Architects), the Boro Hotel in Long Island City, the East Austin Hotel, and the Ranch Motel in San Antonio.
Each property follows a similar philosophy: find overlooked buildings with architectural character, restore rather than replace, and create spaces where locals want to gather – not just tourists passing through.
“What makes our properties special is the attention to detail as it relates to the aesthetics, something that evokes emotion and creates a vibe,” Seidman told NOLA.com in November 2024.
He reserves particular disdain for major chains’ attempts to enter the boutique space. “The Hiltons and Hyatts are now creating these ‘fauxtique’ hotels,” he said. “It’s a testament to how behind the curve they are from a design perspective… Like they’re just putting in Edison light bulbs. I’m like, ‘C’mon guys. We stopped doing that a long time ago.'”
The pause button
In April 2024, Seidman opened Hotel Henrietta on St Charles Avenue – the first ground-up hotel construction on that street in 30 years. Then he announced something unexpected: a pause in new development.
“It doesn’t make financial sense to build any, to do any projects at the moment,” he told NOLA.com. Rising interest rates, escalating construction costs, and threats to historic building tax credits have shifted the economics. “Obviously, much of what I do has been incentivised by historic building tax credits. Most deals don’t underwrite without them.”
Instead, Sandstone is expanding into third-party management – leveraging operational expertise built across 11 properties to run hotels for other owners. “We’ve invested so much in building our team, our company and our presence here, that it really makes complete sense,” Seidman explained. “And it helps in the interim while we wait for rates to continue to go down in the next couple years, hopefully.”
The preservationist’s bet
For a man who jokes he’d “be a lot wealthier if I just went and developed 20 Holiday Inns around the country,” Seidman has built something more interesting than wealth. He’s proven that the buildings America discards – motels operating as flophouses, orphanages crumbling into the Louisiana humidity, motor courts slated for demolition – can become destinations that travellers cross continents to visit.
Now based in New Orleans with his wife Paris Neill (a fellow Tulane graduate) and their daughter, Seidman has rooted himself in the city he first encountered as a student. His mother is from New Orleans. His father attended Tulane. The Columns Hotel, which he acquired with family members in 2019, was a place he visited as a child and drank on the porch as an undergraduate.
“My life has come full circle in a way,” he told Tulane’s alumni publication. “I started in New Orleans as a young adult, then I saw the world – living in Asia and Europe and travelling globally. And now, here I am, back in New Orleans.”
When rates eventually decline and the historic tax credit picture stabilises, the pipeline of overlooked American buildings awaiting transformation remains vast. Seidman will be waiting.
“I’m trying to do what I can to preserve that and not have New Orleans evolve into just another generic city,” he said. “I’ve always felt like New Orleans deserves that.”
