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

Josiah: One of my goals on this show is to raise awareness of different parts of the hospitality business. Today, we're doing that by looking at asset management. Whether you work in operations, commercial strategy, technology, finance, or investment, understanding how hotel owners think about performance will help you better understand the hospitality industry and your role within it. My guest today is Dina Winder, EVP of Asset Management at Highgate and President of the Hospitality Asset Managers Association. Last week, I had the opportunity to join a panel Dina led at the NYU International Hospitality Investment Forum, and I wanted to continue the conversation we started there here on the podcast. Today you're going to hear the first episode in our series together. We start with Dina's career journey, how she found her way into hospitality, and what asset management actually covers, all from her perspective leading this from the highest levels. Let's get into it.

[intro]

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 are a lot of amazing hotels, including this one. And we were talking before recording, around, we want to raise awareness of what asset management is. So you're 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: Yeah. I find that fascinating. 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. And I wonder if you could speak to why the profitability of hotels matters.

Dina: 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.

Josiah: So there's a lot of variability, but there's also a lot of creativity. And I feel like even coming from this conference we were at, hearing a bunch of case studies, there's so many different ways you can drive performance, which is sort of compelling. And you touched on this early in our conversation, where compared to office or multifamily, it feels like there's a lot more to work with.

Dina: That's what makes it fun.

Josiah: Yeah. I wanted to ask you, for people maybe that work outside of asset management, what could they learn from asset managers? There's so much beyond just the hotel operations that asset management does, a lot of which we can teach you. It's the financing and the capital stack that is the portion that's the hardest for people to learn, right?

Dina: That's the finance part of it that isn't the nuts and bolts of hotel management, and that's a completely different skill set. So when we look to hire asset managers or we look to hire people in our acquisitions team, we're looking for people who have that analytical mind. They don't necessarily need to come from a hotel background, but they need to be able to think analytically. Because we can teach the industry.

Josiah: Interesting. And this is your story, right? Coming from outside the industry. Some people I talk with say, "I always wanted to work in hotels, and that was all I care about." But I am curious just on this point, because I am trying to think about how can we show people what personal development, what career development looks like. And I think with your story, you go to Cornell, and then you work across some amazing organizations, you get your MBA from Berkeley. What was most helpful on that journey?

Dina: I mean, obviously working 100 hours a week will do that to you. So that's the foundation. I also can tell you when you're missing a period in any presentation, because back then we actually had to review them by hand, and then fax them to people. That's how old I am.

Josiah: Was that from some early experiences you had in environments where you just had that maniacal attention to detail?

Dina: Oh, I can still remember the first day at Bear Stearns, and somebody gave me whatever task to do. I gave it to the VP, and he didn't even look at it, and he handed it back to me. And I said, "What's wrong?" He's like, "It doesn't look pretty." Okay. I'm going to format this page. I'm going to put it in a table that looks somewhat together. The numbers were right. He didn't even look at the numbers because it wasn't in a pretty, easy-to-digest format.

Josiah: Interesting. So this is something I don't get to talk about a lot on the show. I love the soft, empathetic side of hospitality, but it's also a business. And I feel your experience, leading at one of the biggest hotel companies, but also seeing this investment world, is there maybe a place for some very direct feedback that we need to lead with in the hospitality world?

Dina: Oh. I mean, I hate saying you have to pay your dues. But you do. And whether it's at the hotel or it's at the investment side, it's just basics that you can't skip. Yeah. And I think that's something that everybody wants to leapfrog over, and I understand why. But if you don't have that, then there's no chance to catch up on that because life moves too fast. So if you don't have those fundamentals, like I was talking about, I want somebody with an analytical mind, right? You need to be able to look at a piece of paper, even if you don't know the industry, can you tell me the story from this spreadsheet? If you can, that's awesome. That's who I want to hire. I want to hire somebody who can turn an Excel spreadsheet into a story.

Josiah: I love that, and I feel like I didn't frame up the questions real well, but I love where you went with that because I do feel that is leadership. That is kindness. It's actually ultimately kind to give that very direct feedback and get to the state that you're describing, right? So I think for people listening, they need to think about putting in the time and the effort and the work to operate at the highest level of excellence. And you've demonstrated this over your career. Now you're running not only stuff here, but across the industry, and I think it takes that work, right? There's no shortcut.

Dina: No. And even, you know, we talk about this with all the technological advances and AI, and it can do a lot of the basic computation for us now. But you can't skip learning how to do that and how to interpret that. Because if you just rely on some AI chatbot to do it for you, you can't learn how to tell the story about it.