Weekend Interview: How Jesse Stein Went From Fighter Jets And The NFL To Airbnb's Real Estate Head

This series goes deep with some of the most compelling figures in commercial real estate: the deal-makers, the game-changers, the city-shapers and the larger-than-life personalities who keep CRE interesting.

For Jesse Stein, becoming the global head of real estate for a giant brand like  Airbnb wasn't close to his career goal. 

In fact, for the longest time, the goal was flying fighter jets. When the Air Force Academy didn’t work out due to his history of concussions, the goal became playing in the NFL. 

And Stein did get there. After walking on to the Florida State University football team as a punter while studying finance and real estate, he eventually earned a scholarship. He then was picked up by the Jacksonville Jaguars and even starred on the first season of “Hard Knocks” before eventually getting cut.

“That was hard,” Stein said. “When you train for something your entire life, and you make it close to the mountaintop and you get cut.”

Stein then made a pivot, getting scooped up as a financial analyst thanks to a previous internship at Starwood Vacation Ownership. As a result, he traded in two-a-day practices for 18-hour days running financial models. 

“I'm the son of a five-foot-six lawyer. He had no athletic ability at all. So I wasn't blessed with the athletic genes, but it's all about hard work,” Stein said. “You'll get knocked off the horse a bunch, you just got to get back up, you got to push harder, you got to wake up earlier, you got to hustle. You can use that mentality, not only in sports but also in work.” 

Since joining Airbnb in 2020, Stein has been helping guide the hospitality giant amid its most tumultuous period. He’s working to bridge the gap between Airbnb and landlords by piloting an Airbnb-friendly apartment program as well as working with developers to build branded residences in Miami. At the same time, the company has encountered backlash from politicians, including in New York, where new short-term rental laws have all but pushed the company out. 

Bisnow: You have a background developing hotels at Wyndham Hotel Group, Kimpton Hotels and KHP Capital Partners. Was it an adjustment joining Airbnb? 

Stein: Every time I was trying to get approval for a deal, the last conversation was Airbnb. Airbnb was always top of our mind, and I did a lot of investing based on markets Airbnb wasn't in or markets Airbnb already saturated, because there wouldn't be that incremental growth. 

But then Airbnb called. 

What was really interesting about my time at KHP was I would fly to Denver, I would fly to Austin, I would fly to Nashville, and all I would see was cranes. Just cranes, cranes, cranes, cranes. And when you start looking at the cranes, the majority of them were for apartments. All I could think to myself is there's a world out there where we just build more housing, but we use the housing more flexibly, which will help alleviate the housing issues that we all know exists in the U.S. today.

Bisnow: You joined in 2020 with the world changing and hospitality changing. Can you walk me through how you made that shift, how you rode those waves, especially early on in your time at Airbnb?

Stein: It was interesting because it was a shock. I left a really great group of folks that I really loved. I loved what I was doing personally over there. It was fun to kind of take a flyer — I know it sounds insane now, but take a flyer — on Airbnb, which was not public at that point in time, still not what it is today, not a noun and a verb, and lead a new group. And then all of a sudden, within my first month of joining, Covid hits and our business goes down 80%. And everything that I thought I was brought in to do kind of changed.

Bisnow: Did you think of it as, like, a bad omen? I don't know how superstitious you are, but…

Stein: I'm a big believer in things happen for a reason, and you shouldn't worry about the things you can't control. You have to make some bets in life. I didn't view it as a bad omen, I viewed it as another curveball. Everybody's knocked off the horse right now. We're not in this by ourselves. And how do we make lemonade out of lemons? I think one of the things Covid really brought upon Airbnb is focus.

Bisnow: You talk a lot about building these bridges with other players, whether that's the real estate industry or policymakers. With New York’s Local Law 18, which has been nicknamed the Airbnb Ban, what conversations have you had internally, but also with local stakeholders?

Stein: First and foremost, we philosophically believe people should be able to share their primary home to make some extra money. Everything we do will be fighting for those hosts and those individuals to have the ability to host their primary home to make some extra money. 

When it comes to New York, there's a lot of individuals that aren't able to monetize that, and they need that money. An extra couple 100 bucks a month, that's huge. That's like helping people not choose from putting food on the table or repairing their car.

The real root of this is there's just not enough housing supply. There needs to be more housing supply. But we'll continue to fight in New York and every other market in the world to give individuals the ability to host their home to make some extra money.

Bisnow: Airbnb was making the transition to being a little bit more asset-heavy, then you took the step back during the pandemic. How are you expanding while still staying asset-light?

Stein: My experience on the real estate side helps thread the needle of how we can help these real estate developers build more housing, develop more projects, get more things moving. It's really in partnership with these developers and having conversations with them like “OK, let's try this.” The Miami condos have done extremely well.

I would say we're at the top of the first inning now, but we're definitely going to expand that and expand [partnerships on] the rental side as well.

Bisnow: Give us a bold prediction for the rest of 2024.

Stein: Florida State wins the national football title.

Bisnow: What's your favorite weekend routine or favorite weekend activity?

Stein: I am the head coach of the 8-and-under girls Swifties softball team. I coach my daughter's softball team, and right now it's the age where we pitch to the girls, so I am the pitcher for Team Swifties. 

Bisnow: Do you listen to a lot of Taylor Swift? 

Stein: Unfortunately.