Placemakr has raised more than $350 million, runs buildings across the country, and just became the company Hilton chose to launch an entirely new brand. Its CEO and co-founder, Jason Fudin, trained as a mechanical engineer and worked his way through development and strategic initiatives at Vornado before leaving to build what became Placemakr, where an apartment can be a hotel for one night or a home for a year. In this episode of Space Makers, Jason shares how he turned empty buildings into a new category of real estate, and why the most valuable thing about a building might be how easily it can change.
Jason studied mechanical engineering at McGill, but the work left him cold. He spent 60 and 70 hour weeks alone in a lab building one-dimensional models of sound, and for someone who describes himself as a social person, it was isolating and more than a little depressing. He knew he wanted to build something, just not like that. So he spent months walking around Montreal looking for work that was analytical, people-driven, and carried real financial upside, and real estate development checked all three boxes. The way in was humbling: he took a secretary job at Vornado despite a master's in finance and a degree in engineering, and filed papers until his fingers cracked so badly he says he couldn't touch lemons. Then, close to overnight, he went from filing that paper to running nearly a billion dollars of development.
Back at Vornado, Jason led strategic initiatives, a mandate that came with a lot of whiteboarding and one simple charge: figure out where real estate was going. Most of the proptech he saw was about shaving costs, trimming a submetering bill on a building already throwing off tens of millions in income. His question was the opposite one: how do you actually make money? The answer was hiding in plain sight. A building in lease-up sits half empty for months, and the gap between empty and full is millions a year of cash flow that no one was capturing.
The biggest surprise of the whole venture, Jason says, is that real estate people do not actually move fast. He assumed that if he could hand an owner extra profit on an empty building with no risk, they would say yes on the spot. Instead he learned that the people controlling the most resources are usually more focused on not losing their jobs than on betting on upside. One deal died at the finish line when the owner's CEO admitted he would never stay there himself. Jason asked where he stayed. The Four Seasons. "You're not our customer, friend."
Placemakr had been cruising on its pop-up model, and investors wanted it to stay right there. Then COVID hit, the team shrank from 100 people to 27, and eight openings got canceled. It was also the opening Jason had been waiting for. With the old playbook frozen, investors finally gave him room to chase the real vision: permanent, blended buildings that run every length of stay. He calls it the best thing that ever happened to the company. The team rebuilt from scratch, cleared out what felt like years of tech debt, hired engineers, and settled on three norms they still run on today: make it better, own it, treat people right.
Here is what the model looks like in practice. In Nashville, Placemakr bought a 313-unit tower a block off Broadway that was generating $4 million in income, and Jason says they had it at $9 million within 24 months. When that market got overbuilt with new hotels and rates softened, they did something a normal apartment owner simply cannot: they turned dozens of nightly units back into 12-month leases. "They're apartments now."
The same building can lean into high-cash-flow nightly stays or stable long-term leases depending on what the market is rewarding that month, because it was designed and licensed to do both. Jason's running joke captures how rare that flexibility still is: the apartment world and the hotel world hold their biggest conferences on the very same two days, and neither one has any idea how the other actually works.
In January, Hilton chose Placemakr to launch Apartment Collection by Hilton. The biggest surprise for Jason was how entrepreneurial Hilton turned out to be up close, a culture he says mirrors his own. But the alignment that mattered most was philosophical: both companies obsess over delivering real profit to owners rather than chasing unit count, and putting owners first is what lets the whole thing scale.
That, in his telling, is exactly where the others stumbled. Sonder and Marriott got the consumer demand right and the business model wrong, the same trap that caught WeWork. As Jason puts it, you can get the demand right, but if you don't get the structure right, none of it matters.
Jason's story is a reminder that the most valuable feature of a building is often the one nobody designs for: the ability to change. The companies winning in flex space aren't the ones with the prettiest lobbies or the boldest growth numbers. They're the ones whose unit economics actually hold up, in every market and every cycle.
For developers, owners, and operators, the lesson is clear. Most buildings are built for a single use and quietly leave money on the table. Build for change from day one, prioritize cash flow over revenue, and the optionality pays for itself.
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