Asset Management Is Hospitality's Most Misunderstood Career - Dina Winder, Highgate

Dina: I didn't come from this world. I didn't grow up in the hospitality industry. This is something that was completely foreign. I went to Cornell, but I was in the ILR School. This was not something that was in any way planned.

Dina: I didn't even know this was a job. It was something I kind of landed in. When I got out of school, well, roll back. I had an internship before senior year at the formerly known Bear Stearns.

Dina: Rest in peace. Great time. They then offered me a full-time job. I still really didn't know what investment banking was, but people told me that was a great training ground to do anything else you wanted to do, which I had no idea what I wanted to do. All I knew was I wanted to be in business.

Josiah: Which is really broad.

Dina: Yeah, no idea. So I spent three years at Bear Stearns in their real estate lodging leisure group. Did some fascinating deals with people that I still work with today, and went back to business school because I realized I had no idea what business was. And then that's when I started to understand the hospitality business more. I thought I was a real estate person coming out of Bear Stearns, but I realized I was a hotel person.

Josiah: What was that moment? How? Was it all at once, or was it a gradual process over time?

Dina: So I interviewed for a bunch of different jobs for real estate, and then I got in touch with Kimpton, and it was a cold email to Joe Long. Bless his heart, he answered it because I was a Cornell grad. And he hired me. They had just raised their first fund in 2005. So he gave me an offer, and then I had an offer from other real estate companies, and I sat down and said, "If I have to value office leases for the rest of my life, I think that might not be a great fit." I really liked the operating business. So I liked the real estate, but I needed the story, and I couldn't get that story in my head for any other type of real estate.

Josiah: That's amazing. Now, I feel like I want to get into so many elements of this. Many people know Highgate, but I want to hear in your words, how would you describe Highgate, and then how would you describe your role? And then I think we're going to get into a lot of threads of what you raised.

Dina: Yeah. So Highgate is an amazing company. Largest independent, still very much in its roots of owner-operator, which is one of the reasons that I joined and I came on board. Super smart people, the smartest people I've worked with, who are constantly changing the paradigm of how we work, trying to think of things just differently. No doesn't exist here. It's, "Okay, well, let's just try it." Which is something I love, and that's one of the reasons I joined. So I was working private equity, and this opportunity, really I didn't know what I was going to be doing. I was talking to a bunch of the principals, and they're like, "Just come on board." Well, what am I going to do? They said, "Well, this is great." So I wound up, I started our asset management group when I came on board in '21. And before then the acquisitions team was doing the asset management, which is how it is in a lot of shops. But the portfolio was getting bigger, and we needed some more institutional asset management.

Josiah: So the portfolio is large, it's diverse. We are recording at one of your hotels in Midtown Manhattan. I'll include a link in the show notes where people can check out the portfolio, because there's a lot of amazing hotels, including this one. And we were talking before recording around, we want to raise awareness of what is asset management. And you are the president of the Hospitality Asset Managers Association. You're running asset management here at Highgate. For people who are unfamiliar with this part of the hospitality ecosystem, what is asset management?

Dina: In one phrase, it's being the owner's rep, which I think is something that people can kind of get their head around. But it's that person at the table who is keeping the owner's interests in mind. So on a day-to-day basis, it could look completely different, and every day is different, which is why I love it. But it's everything from underwriting and doing due diligence on a deal to financing, construction, renovation. You're putting together a business plan, and then you're executing that business plan. So sometimes there's a big renovation and repositioning. Sometimes it's just, hey, this is a cash flowing hotel, let's just keep it a cash flowing hotel, and it's a different risk profile in our portfolio. So we're making investments for different reasons, and I think that's the interesting part. Every hotel has its own story, and we say that from the management perspective all the time. But it's the same from an investment perspective, right? No two deals are the same.

Josiah: I find that fascinating. I had the privilege of being on a panel that you led at the NYU International Hospitality Investment Forum talking about this, and on the show, on Hospitality Daily, I'm trying to raise awareness of how the economics need to work for owners for all the beautiful things that you mentioned at the beginning of our conversation, being attracted to so many elements of hospitality. But the financials need to work, the economics need to work for owners, and I feel like some pockets of the industry are having more awareness of this. But for people maybe that are new to this world, or maybe don't care about owner returns, I wonder if you could speak to why the profitability of hotels matters across the ecosystem, because I think it's fundamentally important for all the things we love in hospitality.

Dina: I mean, at the end of the day, the real estate trades on the income that's coming in. So in an office building it's fairly easy, right? You have a long-term lease. You can value that lease. You can do a DCF, a discounted cash flow analysis, and you can see what your income is going to be for the next five, ten years, as long as those leases are. In the hotel world, we reset our leases every day on every room, so it's a lot more dynamic, which is why I love it and why a lot of people are in this industry. But it's a lot more difficult to underwrite. So that's why it matters so much, because there's so much fluctuation. Especially on the independent hotels, but overall, hotels tend to go up faster and down faster than the rest of the real estate world because we reset our leases on every room every day.