David McCaslin, Partner, CapStar Advisors, interviewed by Lan Elliott

Dave discusses the importance of delegating and continuous learning as one progress to larger roles. He shares how he acquired the New York Palace with a 3-person team – and why he hires people who have experienced failure.  He explains how to navigate industry receptions, the right way to ask for something you want, and how to be prepared when opportunity knocks.

Transcript

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Lan Elliott 0:00

Hello, and welcome to It's Personal Stories. My name is Lan Elliott on behalf of It's Personal Stories. And today I'm really happy to have my friend Dave McCaslin on with us. And Dave is partner with Capstar Advisors and has had a tremendous career. If you're not familiar with Dave's career, I hope you will go on our website to check out all the wonderful things he's done over the course of his career. Welcome Dave. Well, thank you. I'm very pleased to be here. So always happy to help. Thank you, Dave. I know you've had just an incredible career and just admired the things that you've accomplished over the years. Could you share some of the pivotal turning points in your career? And if there were any. factor or factors that contributed to your success?

Dave McCaslin 0:55

Sure. I think in thinking about it, there's probably one thing that actually before my career started I played baseball is a kid and my father did not play a lot of baseball, but he coached me. And I didn't realize it till later, but he would always set out every other player on the team. And then I played a different position every year because he put me at the position that was the weakest position. So I think in retrospect, it really taught me to value teamwork, to be fluid in what I did. I learned a lot of different things and to how to build teams. And then I think from a corporate standpoint, I had a pretty traditional role. Start, hotel degree got into ops. I was with Weston and then went to a smaller company, Lincoln. And I had a chance at the late twenties, in my late twenties to either go with PKF and become a consultant like a lot of my friends did, or to go with another large company and trust house forte and that might even lead international or I had a chance to help start a company. And so I figured that I was young, I was married, but I didn't have any children yet. And that if I was going to do it, this was the time to do it. And so that has led me to being a serial entrepreneur. And that is probably the single pivotal career moment that I really had.

Lan Elliott 2:17

That's so interesting, this spark to be an entrepreneur. Do you think that came naturally? You always had it, or do you think that first experience led you to be more comfortable with more entrepreneurial pursuits afterwards?

Dave McCaslin 2:32

I was probably raised fairly traditionally, but I was always had a lot of curiosity. And so I wanted to do things, I wanted to learn and to explore. And I found that most of the other things put you into a little bit of a box. And so I think I always had a little bit of a spark to try it. But I don't know that it was necessarily inbred or I was like, destined to do it. I think the circumstances just led me to it. And then once I did it, I just loved the kind of continual innovation of it.

Lan Elliott 3:06

And you had mentioned curiosity, which is a trait that a lot of leaders have mentioned on our podcast. And. What I find interesting is that the skills that take you to about halfway through your career serve you really well, and then usually you come to a point where you realize, oh, there are some other things that I need to learn how to do that. I didn't need up until now, but now I need to focus on and develop those new skills. Did that happen with you? Was there something you discovered that, okay, now in my new role or in this next chapter, I really need to focus on a new.

Dave McCaslin 3:46

I think the biggest change, we were always dealing with teams when you're in a hotel type of situation. But for the most part, early in your career, you're in positions where what you do in that job determines what happens. And and you can generally through force of will or force of personality dictate what happens within a smaller zone. And then I think when you get to a larger platform, you realize that you can't really do everything. And you have to figure out how to pull back and let other people do things and still make sure they're on the same pathway that you want. And provide them with feedback, but you just get to that point where you can't do it all yourself. And I think that's probably the biggest struggle for most people. It was a bigger struggle for me at a point because you're used to what you do that made you successful. And then you have to pull back from that. And then once I became comfortable with it, I was, it was actually. fine and I could get a lot more done. And so it was actually a great learning experience. But it was a learning experience.

Lan Elliott 4:55

Yeah, I think you make a really good point, which is what makes you successful through sheer force of will or hard work or whatever gets you to a certain point. But like you said, you can't scale. You can't then move on to bigger roles unless you learn how to work through other people. And help other people be successful and learning to delegate, and letting go. And for those of us who are control freaks, letting go can, tends to be quite difficult. But I think a big, it's actually very scary. It's scary, right? But I think learning and growing. In a way, as a leader where you can then impart to your team how to do things and ensure that they're stepping up their game and they're growing. All of that can also be super fulfilling.

Dave McCaslin 5:46

No, I think it is. And I, and it allows you to expand what you're doing and to continue to learn because otherwise you continue to do the same things you've always done. And so when you do find that you can let go, it allows you to expose yourself and continue to learn. So I like that personally, and I think it's what's best for corporate organizations.

Lan Elliott 6:09

Yeah, I think that's true. And I think eventually people want to learn new things. And you're right, you have to let go of other things in order to learn the new things that you need to do. I wanted to talk a little bit about taking risks because you talked about the entrepreneurial piece of it. About being at a crossroads and choosing that entrepreneur. How do you approach taking a risk? How do you prepare yourself mentally to do something like that? Is it something that comes naturally to you or do you have a method? What's your trick for approaching risk? No, I think

Dave McCaslin 6:47

risk is called risk because it's scary and the outcome is unknown. And so I think that I don't know that. It comes naturally to people. I think it's a little bit learned of what you do and what you want to take. And so I think that from my standpoint, I always tried to look much further down the road in terms of was what I was doing, if it was a risk, I didn't always analyze it just in terms of the risk of what was in front of me. I'd look at, does it help me get somewhere down the road? And could I do things that would help minimize that risk? And one of the ones I've talked to some other people that thought I was Probably a little bit of crazy to do it. But when I was with a company called Northwood, we started from scratch. We had not, it was, we did the first hotel. It was me. That was the only corporate employee. It was a smaller project, but I hired the right GM and I knew I could work with that person. By the second person I had somebody in accounting. And so we did our second hotel and our third hotel was the New York palace, which was doing 190 million a year. And we had two corporate employees and normally you would have said this was impossible, but I figured out what I needed and I went and talked to people that I trusted and I got together a team of three people. that I knew and I got them to agree that if we got this deal that we would go forward and laid out what the path looked like. And so five weeks before closing, we went hard. They all gave their notice 2 to 3 weeks before we took over. They walked in the door and but they were all seasoned people. And they had their specializations and I knew what I had already analyzed the hotel where the opportunities were and what not to really play with. So that was a large risk, but I think you mitigate your risk when you plan, when you understand what could make things go wrong and you take steps to correct those.

Lan Elliott 8:52

I do like the idea of putting a box around the risk that you're taking and saying, okay, what can I do to mitigate different risks? How do I bring the risk profile down a little bit? And I love the idea also of bringing in trusted people from your network. And I do want to get to that in a second, but I love that theme as well of mitigating risk by bringing in people that you trust and using your relationships to help you get through that. Anyone who takes a lot of risks, and you've had to take a lot of risks to be as successful as you are, sometimes things don't turn out the way you hope. And I think for a lot of us, it's a situation where you learn more when things don't go well. Then you do what everything goes perfectly according to plan. And I'm wondering if you've had a setback that was a great learning opportunity for you.

Dave McCaslin 9:49

Oh, I've had more than one setback, but I, I think nobody sets out to fail at anything that they do. But I do agree. It's a truism that you learn more from what you don't do well than what you do well. And you can take those learning experiences and grow with them. But it's painful at the time. And so I've always looked at it. Honestly, if I hired somebody, I would ask the question if they didn't really have failures. I tended not to hire them because I didn't want somebody who had been that conservative. And if they had a failure, how would they actually handle it? I wanted somebody that knew what they were doing. So I was Probably famous when I was CEO of Maristar, I had a large picture in my office of eight hotels, and they were the eight hotels that I had dealt with that I felt like I had failed at, and that they all had something wrong with them, and that I either hadn't seen or that we couldn't overcome, like a market or a physical product or a location and I had it in my office as a reminder of what those things were so that when I looked at anything new, It would tell me like, how do I make sure that I learned from those things and didn't repeat that? And, I think that's probably it on the hotel side on the corporate side. There was one startup that I did that we ended up being financially successful. And that company still exists and they're doing fine. But I I came into it as a startup with a certain set of cultural values. They had a different set of cultural values of people that I was partnering with and, it was professional, but in the end run, it just didn't really work. And I think that the lesson that I really learned from that is that you really are investing with people as opposed to more so your capital. And what those people do and how you feel comfortable with them you don't really even have to like them, but you have to respect them. And you have to know that when things go bad, you can trust them is probably the most important thing. And that's probably the most important lesson that I think I pulled out of anything that I've done that I would ask somebody listening to this to contemplate.

Lan Elliott 12:03

Could you talk a little bit more about that? Cause I think that's really interesting. In terms of when you put together a company and you're partnering with people. How do you figure out who are the right people for you? I know you mentioned failure, checking if they have ever failed and how they handled it, but are you looking for certain things when you go into business with someone? Do you now have, I know you had your eight deals that you try and not make those same mistakes again. And that's your reminder, almost your checklist, but do you have in your mind certain values or certain things you're looking for when you're going into business with people?

Dave McCaslin 12:46

I think I do look at how they've handled adversity in the past and how they interact with people. And I do that because honestly, when things are going well, you can get along with anybody. Checks are coming in the door. There's not a lot of friction. There's really nothing to argue about. And it's only when COVID, economic depression, Interest rates go to 12 percent or whatever. It's only when there's some extraordinary event, then the pressure is really hitting that you can tell when somebody, how they act, how they deal with you. Do they look to put the blame somewhere or do they jump in and try to help you work with it? And so I think the biggest thing is is it somebody that I can really trust when the chips are down? Because if you're, in our business and you're view is 5 to 10 years out. The chances of nothing bad happening over that time frame are about nil. And so you you want to know that you can get through those periods with the people that you're with. And I think the other things that I look for is, do they, in some cases, do they have a specific talent that you can put them in that area and have them do? I tend to value fluidity. I've always been more of a growth person. So people that can handle Change is probably a big deal for me. That may not be as big of a deal for other people that are perhaps a little bit more static in terms of what they're trying to accomplish. And I actually look for people that have a little bit of something to prove is that, whether that's in their career or in their personal goals or something like that, where I know they're going to just, when the things get tough, put out a little bit extra. And I think that's part of what drove me. And I respected that for people that I would surround myself with. Those are the things that I would tend to look for. There are roles that's not necessarily the right thing for the entire world or for every organization. But for me and what we were trying to do, that was what was very important to me.

Lan Elliott 14:47

Yeah. Those are really important traits to, to look for. Thank you for sharing that. And for sharing, what you've learned when things don't go the way you hope they will, and you're right in our industry, you're always going to have downturns. It's just the nature of it and investments when you're doing deals and you're working on things, they are unlikely to get done in a short enough period of time where we don't run into one of these cycles. So I think approaching things in that way of, what happens in the worst case scenario and who are you with in the trenches at that moment is such a great lesson to think about. Along those lines, I wanted to talk about developing. a network because you have quite a vast network from your years in the industry, but I'm curious how you've developed your network in a way that's comfortable for you, that's authentic to you.

Dave McCaslin 15:52

I think a couple things. One I, it's an overused phrase, but I like people. And so in our industry I, most of the people that I run into, I like the almost most of the rest of them. I may not like, but I'm okay with, and there's really only a handful of people that I just really distrust, which I came down to. And so if you go out with the approach that most people are basically good, if you allow them to be good you can form bonds of friendship with people. And because I was putting myself into situations where I was in growth companies, I developed deep networks within what I'd call the ops performance areas. Cause we always needed people to run hotels, whether the corporate or the hotel level, but you also ran into franchisors. Capital partners, vendors, competitors, that did, they came into play. And it is a social business. And so I think, social business I really could find ways to relate to people. And if I could relate to them, I felt more comfortable with them over time. And then the end run. You really only judge somebody by how they did within their work, but if you felt comfortable with them, you could share things and share experiences and things of that nature. And I don't, I think the mistake people often make is even the term developing a network goes and assumes a transactional, I need to find somebody who does X and their value is only is what they can do for me. And I think people sense that and don't like that. And so if you can help people, even when there's nothing in it for you directly, but you develop a relationship with them it helps you and you don't really even have to expect anything in return. Amazingly, sometimes 15 or 20 years later, something may come up and you do get help. And and people went about it, but I would say. The one thing I see of people coming up today is you don't necessarily have to do anything crazy, but they're all worried about, did I do something silly or I want balance, or I want this is that they view the relationships as being transactional. And I think you should really view it as a relationship. It's not as important as a family relationship. It's not as important as a extremely personal relationship, but it's a relationship. And. If you stay in the industry, you're going to know these people for 30, 40 years through ups and downs in their career and their personal life and things that happen. And I think you want to do that. If you look at it as purely a transactional situation I don't think it really goes well, but all you essentially have to do is a expose yourself to A broader variety of people. So if there's a chance and there's a reception at one of the conventions, it's an hour and a half in the evening, right? Don't run back to your room and play on your phone and do whatever the other things are. Like go to the reception, talk to people, and don't just talk to the people that you already know. Talk to other people or have them introduce you and work from that standpoint. And if you don't like somebody, you don't have to develop a relationship with them. But you have to do, you do have to get out there and talk to people and most people are pretty good. So if you just broaden your network, you'll find people that you like and you'll be able to help each other over time. It's not really that different. You just have to spend a little bit of time and effort at it.

Lan Elliott 19:40

Yeah, I love what you said about these relationships lasting many years and decades. And I've definitely found that to be the case. And it's been wonderful, actually, to be able to follow friends through the different evolutions of their careers over the years. And maybe there'll be a time where you can work together. Maybe there's a time where you can help one another, but I do love the idea of making it more about the relationship and not being transactional and what can you do for me? Sometimes it's just having those relationships is enough and it will maybe someday help you, but maybe someday you can do something nice for somebody else too. And that's okay.

Dave McCaslin 20:20

It's like Christmas or Santa Claus. Actually, I think I get more thrills out of helping somebody else than I do out of them doing something for me.

Lan Elliott 20:28

Yeah, that's very true. I wanted to pivot to mentors and champions and talk a little bit about how important is it to find mentors and champions in the business world and how does one go about it? If that's something that You've had mentors and champions. How do you go about finding them?

Dave McCaslin 20:54

So I view it the same way as a network. I think that if you go out and you're it's about me and what can somebody do that? And, or somebody like companies will set up formal mentors and I'm, I don't totally diss that, but I think when. It's a forced situation. It often doesn't work nearly as well. And so in order for a mentor situation to work, the mentor has to actually want to spend time and help other people. not because they're told to do it, but because it's in their nature. And if it's in their nature, they'll do well at it. And the mentor, I think, generally looks for people that are, want their input and are receptive to their input, and then they're willing to do it. So if it's just somebody that kind of walks in the door they don't do that. But I think there's a, there's an excitement to helping somebody grow. And I'd say, even from my standpoint, I didn't look at it when I was younger, but as I get older, like you want to give back and, but you want to give back in ways that, or to people that you think will respect that. And so I have had a few mentors and, the first one, they're probably the most important one to me. I think I, we work together. But the mentor relationship really took off after we quit working together, where they would still try to look out for me and make sure things were okay. And I could call them up and talk about things. Whereas when we were in the same company, we helped each other from a business standpoint, but it was much more about the here and now and what issues are we trying to take over and afterwards. But that relationship, Came from that initial working together and then developed into more of a mentor relationship. And then champions is interesting. A person that I worked with early in my career and then stayed in touch with later in my career, out of the blue called me and said, Hey, I've got this capital source that I know that I'm working with and they're looking for somebody. And I think you'd fit the bill. And I had no idea who they were. Hadn't really even heard of them. And they made the introduction and then it worked out wonderfully, but they weren't a mentor, but they were a champion. Like they thought enough of our relationship or what I did that they thought it would work, not just for me, but for the other person. And I think that's the key to a lot of this is it should actually work for both parties. And the reason it sometimes breaks down is that people look at it as what's in it for me. And most people don't react well if they're approached by somebody who's only in it for what's interested in them. And they don't take the time to understand what the other person really wants to accomplish. But they're very, both of them are very important aspects in a career that if you can find people that you're comfortable with. It really can't help you because they make you look at things in ways that perhaps you didn't always look at it and cause you to be a little more introspective.

Lan Elliott 24:08

Yeah, I love that to be able to give you a different perspective and I've found that too. I've learned so much from. Asking for help, which took me a long time to get to a point to ask for help, but it's wonderful to get different perspectives and different ways of looking at things. Sometimes you're thinking about a or B and your mentor would be like. You're on the wrong alphabet. We need to be looking over here instead. And so great to be able to shine a light on some of your blind spots. And then also the champions. I read somewhere recently that your brand is 60 percent what people say about you when you're not in the room. And I hadn't heard that, but I,

Dave McCaslin 24:52

I love that story because I. I think there's a certain truism to it. That, that is true is that it's not what people are paid to say or what they pay, what they politically say within the right things. It's what do they say when they're just being honest and that is who you are. I think one of the things you said I would also pick up on is that for anybody watching, it's not a sign of weakness to ask for help. It's a sign of curiosity and you wanting to. Expand yourself and learn.

Lan Elliott 25:22

Thank you. Yes, I think that is an important lesson to learn, especially when you're young and you're coming up and you're afraid to look like you don't have the answers. But I do think when you've done all the work, and you've tried to figure it out on your own, I think it's also good to go and ask for help and say, I've tried to figure this out, but I need a broader perspective, or I need more experience to help me. Understand what this really means. So thank you for. For amplifying that to talk a little bit about advocating for ourselves, because it's such an important skill in career advancement. I would say a lot of times women and some underrepresented groups don't always do a great job at advocating for themselves for a number of different reasons. And I'm curious what you would tell our audience who are struggling to find their voice. What's the right way to ask for something that you want?

Dave McCaslin 26:21

I think the right way to ask for something that you want is to think about ahead of time, who are you asking it of? And looking at it from their perspective. Sounds crass to say what's in it for them, but like, how would they view it? So if you're looking at something from a corporate standpoint, they would have an obligation to make sure that what you're asking for is best for the corporation. If you're asking for a, let's call it a donation of time towards something, then figure out, does it affect. Something that they look at charitably or something of that nature that they're looking to to do Is that think about when you approach them don't make it just about I want this Think about how it's going to affect them personally or the organization personally and how you want to phrase what it is and most people Again, there's always exceptions, but most people I think want to help And most of the time is somebody doesn't ask, or they're afraid to advocate for themselves. There's sort of a perception that'll be difficult or it's a perception that the person doesn't want to do it. And they're going to have to talk them into it. That can happen, but it's rare. Most of the time, if you're not getting exactly what you want, it's because people are so busy, they don't have time to think about it, or they're not aware of what you're trying to get accomplished or they've got their own issues that they're dealing with at a corporate level. And so just the act of asking most people will engage about the worst thing that will generally happen is I can't talk to you right this second, but can we make an appointment to talk is. And then when you get them, when you're calm. Just be direct to the point, talk about it, how it impacts, can be change, why, and don't focus so much on you focus on the organization and what's going to make it better for them. But you can just say, I would like to do this. I'd like this promotion. I'd like a chance to be exposed to these types of things. I'd like to spend more time on a charity thing. It doesn't even always have to be about work. And if you're uncomfortable doing it because you're not sure, or you don't know the person, if you're uncomfortable doing it, start small and do a couple of test things with other people to like anything else, it's practice. And if you're approaching somebody that you don't know, you're not as likely to get a positive response as if you know them. So find somebody that knows them to introduce you, and don't make the ask on the first time that you meet that person. Get to know them a little bit first and what makes them tick and then go through that. But I am somebody who's eternally an optimist. I believe that most human beings are good. There are circumstances that make them do bad things or stupid things, but most people want to help if given the right circumstance and approached correctly.

Lan Elliott 29:23

We are coming up on time and I wanted to ask you two more quick questions if I could. Sure. One of them is one of our favorite questions on our podcast, which is what advice would you give to your younger self? So I am curious, what advice would you give to 22 year old Dave McCaslin?

Dave McCaslin 29:47

I think I'd give him the advice that I still haven't actually worked out yet, which is I spent So much time focused on performance and kind of what happened and the people that were there and what was in front of me. I would say I could have done a much better job of managing upwards and I'm a little better at it. I still don't think I'm that good at it and I probably don't worry about it that much, but probably realistically, if I could have spent a little bit more time doing it, it probably would have made things easier. And, I think the corollary to that is you want to be competitive, you want to win, but you don't have to win everything. And so sometimes if you're right and you're convinced you're right, even if you're right, you may have won the battle, but lost the war. You got to figure out like, what am I really arguing over? And I'd say the other thing that I would look at is make sure that if you're taking a stand. That it's really worth taking a stand over, and it's part of a longer term strategy and not just a, I'm in the moment and this is the way it's supposed to be.

Lan Elliott 30:57

Yeah, those are really good pieces of advice and it has taken me many years to learn that it's more important to be effective than to be right. And I think both of those go towards that thought. And sometimes it's very hard at the heat of the moment to remember that. And one of the themes you've mentioned again and again is to think about it more in the long game and the relationships over time. And is it more important to be right in this moment, or is it more important the end game and the relationships into the future? Thank you. You've offered so much great advice in our conversation. I wonder if you might have one last piece of advice for our audience, keeping in mind that our mission is around empowering personal success. What would you offer as one last piece of advice to our audience?

Dave McCaslin 31:56

All right. Career is a long period of time, and people talk about things like the arc of a career, and it implies that there's like this smooth curve that kind of goes on, and if you go out far enough, it probably looks like a smooth curve, but in reality, it's had all these little ups and downs and things that go along with it, and Realistically, it isn't that smooth because it isn't Hey, I just got to keep running a marathon and put one foot in front of each other. There's an element of that, but I think for most people, there are a handful of times over 40 or 50 years where they are put in situations where they're going to make a decision that really can change their career. For good or for bad, depending upon the decision that they make. So if you look at it for good, I think that you have to realize there are things that you cannot control, cannot really control the economy or kind of what the macro forces are. You can't control whether an opportunity exists or not, but you can control. Knowing what you value personally, what type of risks that you would want to take, what your long term goals are. And be ready so that if an opportunity comes up, so if an opportunity does come up and that's the time you start thinking about, should I do X or should I do Y the mistake that most people make is that opportunity closes before they can figure out what they want to do. So if you can control and you only get maybe three or four chances over 40 years. That something comes up and you already know what's important to you and what you want to do. When that opportunity comes up, you can act. And that's the thing that I would say is that think about it less of a marathon and more of a series of races. And then you get to a point where there's a fork in the road. And as Yogi Berra would say, there's a fork in the road, take it.

Lan Elliott 34:02

Well said. Thank you so much, Dave, for sharing your wisdom, sharing all of these lessons that you've learned over the course of your career. And I really appreciate you making the time to be on and sharing it with our audience.

Dave McCaslin 34:17

I said, happy to help. I hope somebody looks at this and learn something from it. I'd be very happy.

Lan Elliott 34:23

I know I already have learned a number of things from it. So thank you so much. And for our audience, if you've enjoyed this interview with Dave, I hope you'll go to our website. It's personal stories. com where you can find other wonderful interviews with hospitality industry leaders. Thank you.