Not Done: Sloan Dean After Remington - How He's Betting on Himself and What's Next

Josiah: We have so much to talk about. You've led Remington to an incredible place. You've recently stepped down as CEO. I wonder if we could take a moment to look back on the years I've spent as CEO, doing extraordinary things. I feel like what you built at Remington was at the forefront of innovation in hospitality, leadership, and management. Looking back on that experience, what are some of the things that you're personally most proud of?

Sloan: That is a great question. There's a lot. I'm very, very proud of what we did and have done. I was there for eight years. I mean, you blink and it flies by. It feels like just yesterday that I was given the seat. There's probably three things. You know, if I look back on my time, think about what I am most proud about. First and foremost is the cultural revolution that we brought. When I started, Remington was not really well thought of in the employment marketplace. We were just the Ashford captive management company and was kind of a secondary thought. If you were an associate looking to become a GM or advance your career, we've seen our Glassdoor rating rise from a 2.5 to as high as a 4.4 even surpassing Hilton at times. And that wasn't one thing. Yes, of course, the employer branding that we did, re-imaging Remington Hotels as Remington Hospitality and the tagline we're known for, "room to thrive," and being the place where passionate people thrive. It was a lot of effort, a lot of iterative effort and multi-year, and that journey is never done. You know, we started that journey in 2018 when I took over. That's probably what I am most proud about because we really did upend and reinvent the culture of the company to when I left, I felt with complete conviction that we had improved the company both optically externally and also actually internally for associates. And I always talked about, I wanted us to be the place that you hire to retire. And I think we started that and that journey is still going on. So that's number one.

I think probably number two is we survived COVID. No one plans to have zero occupancy in their hotels. And I think any hotel CEO who survived 2020 and lived to tell about it did some harrowing things, worked long hours, got in front of their teams and inspired them to keep going and reinvented the way they did business. And I learned more in 2020 than any other year. Now, I never want to relive it. I don't want to go through that, but strong muscles are made with heavy weights. And I think COVID taught me a lot in surviving and shepherding the company through that period was not only transformational, but was necessary. And I learned a lot, the team learned a lot.

The third thing is we more than doubled the size of the company. So when I started, we had about 80 hotels, only Ashford as an owner, and fast forward to today, it's 150 hotels, 44 capital partners, six countries, and our revenues went from kind of, call it six, seven hundred million in hotel revenues to 1.5 billion. So really good growth trajectory in a six, seven, eight year timeframe. And most of that growth came post-COVID. So those are probably the three I've had the very fortunate experience of having tremendous people underneath me. And if you're listening in, it was really the people that made the difference. And thank you.

Josiah: I love it. I'm going to include some links in the show notes we've recorded over the years, telling some of that story. I love nerding out on the details of this kind of stuff. You talk about culture, you kind of shared a deep dive in all the investments. It was substantial. This wasn't just a poster on a wall, right? Heavy, heavy investments over years got you to this place, all starting with people, all starting with the culture, right? Incredible.

I want to make this kind of personal, Sloan. You are now moving on to the next thing. How do you think about what's next after being CEO? So many people spend their entire careers kind of hoping to one day be CEO. You've done it, you rocked it. And now that you're post CEO, you're thinking about what's next. You got a lot of good stuff cooking. I would love to hear your thoughts on that because I'm personally interested. But also, I think for our listeners that may be going through a career transition, maybe they held the leadership role that they always wanted and they're in this point where they're thinking about what's next. How have you approached that process?

Sloan: I have always been a lifelong learner. My probably greatest strength is my curiosity. And I have yet to read enough books. I've yet to face enough challenges to feed that curiosity fully. And I have been very fortunate. I don't know any other CEOs who are not founders who had the opportunity to be CEO of a multi-billion dollar business at 36. You know, in today's tech world, that is common with founders of tech businesses, but of operating businesses where you're not the founder, it's pretty rare. And I feel really fortunate and I do feel like we did great things, but I think what so often happens is you reach a point and you think that is the summit. And I never thought, and this is no knock to Remington, I never thought being CEO of Remington was my summit. I've always had an entrepreneurial spirit about myself. I've always wanted to leave a big legacy. And so to be able to do the next thing I had to leave. And it's hard. And frankly, I stayed probably a year longer than I would have because of the people. But I do think you get it from my own father because I'm self-made and my dad was the first person in his whole family to ever go to college. A lot of my qualities I get from my father, a lot of the good qualities about people first, humility. But he didn't understand. The first time I told my dad that I was thinking about leaving and doing some other things, and some of which are still confidential I can't talk about today, but obviously I'm doing the podcast is one. He was like, why? You made it. You're the first CEO in our family. Like, what are you doing? And so, and I love my father. He's my hero, but you can't be afraid of the unknown.

I think most humans, both investing and in careers, don't take enough risks. And I think if you look at someone, I know Elon Musk, but you look at him and the success, his risk tolerance is through the roof. And if you look at a lot of successful people, their ability to take risks is greater than the average human. And I think that's where a lot of people come up short is that they're not willing to take necessary risks and self-confidence I don't lack. That doesn't mean I'm arrogant, and I'm betting on myself. That's why I'm doing this. And it is a bit odd to walk away from a substantially compensated, well-known position and to walk away from it. But this is what my family and I feel like is best. And my own father didn't understand it at first.

Josiah: So I wonder if you could tell me a little bit more about what you have to push through to take that risk to move to that next level. You're touching on this just a little bit. Does this feel scary? How do you, everyone wants that growth, right? What does it feel like to kind of push through and make a decision like you did?

Sloan: Well, oh man, it's cumulative. It's a lot of different things. I had been thinking about leaving as CEO for about a year and a half. So I took my time. I didn't have any preconditions that I have to do this by this date. And I had in mind some things that I wanted to do outside of Remington, but I couldn't do it because of a conflict situation with being a CEO under an employment agreement and affiliated with some public company. And so I knew that most likely the path was I had to step away at some point, but it's a lot of reflection, a lot of talking to my wife, Pam, who also has got a great business mind and bouncing off of her and reading a lot, reflecting. And then just, I think what a lot of humans don't have is like the end in mind. I have a vision of end in mind of what I want to do, figuring out the steps to get there. I knew when I was 20 something, I wanted to be CEO of a large company. That's why I was able to get there at 36 because I knew where I was trying to go. I was a little more intentional. Most people just think, well, let me go get this degree. And then that'll set me up for the next thing and what comes, come. I try to think like if I want to be a founder of a transformational legacy company, then how do I get there? Most people are just, let me go get the next grade. Let me get the next promotion. I'm trying to work back from the end in mind. And so that gives me comfort that I feel confident that at 24, I wanted to be CEO and I was at 36. Now 44 and I've had success and I know what I'm looking for.

I also, selfishly, I built up, I'm just being frank, a net worth that allows me to be able to step away. And if I need to go invest hundreds of thousands of dollars in a business, then I can do that. And so I think being at a point financially that you can do that, but you don't need that. I mean, if you're a self-starter entrepreneur in today's AI world, you can start a business with nothing. I'm just speaking it made me feel more comfortable to step away that I'm not worried about paying my mortgage. That's just the reality.

Josiah: Yeah. I mean, I think like sometimes people don't get into that, right? And I think just being transparent, like that's kind of your set of circumstances. Different people have different levels of things in their life that they have to think about. And I appreciate that. How much can you tell us about, you said you can't talk about everything. It seems like you hinted at being the founder of a company that's transformational. How much can you share with us today?

Sloan: So I've got three or four things working. The one thing I can't talk about is I just announced Not Done, which is very literal in this branding. I'm far from done. I'm 44. I'm not going anywhere. I'm staying in hospitality. I do have a year non-compete that I'm honoring with the company. I do have your typical non-solicitation standstill. So I'm in a kind of a garden leave period. Being on a podcast has no impact on that. I'm advising two companies that I believe in. One is in the tech space in hospitality and one is kind of trying to revolutionize how we staff hotels. The other one I can't talk about yet, but I'm focused on three things over the next year. And there's kind of three S's.

Friends and family. I've spent more time with my kids and my wife last two months than I have ever, which is awesome. So it's kind of getting that back, whereas I don't have to work 80 hours a week. Second is fitness. I've been really focused on getting back in shape. I started this workout that's called the Norwegian 4x4 to increase your VO2 max. I'm really trying to get my BMI down. And then the third is founder mentality. So I've been reading a lot, watching a lot of podcasts. I'm actually taking courses at MIT on AI. So I'm now a student. So I enrolled, I paid tuition myself, which has been 20 years since, or no, I guess I graduated college 22 years ago. So I am taking AI courses in the fall at MIT. And so that's all part of the master plan, but that's what I'm up to. It's kind of the three S's. And the longer I go in this next year, the founder mentality becomes a bigger part of the pie. And that's why I really waited until I was gone for about two months before I launched the podcast. I really have only started the advisory work I'm doing and that's on the side, is advising the CEOs of the company. And so that's what I'm up to as best I can share. There'll be more in future times, but I really want to disrupt the hospitality industry. That's at the heart of it. What I want to do is be a disruptor and set up the industry for a greater success.

Josiah: This is not new to you, Sloan. You've been a disruptor throughout your career. You've also been one that you've never held back from sharing your opinions, contrarian takes on stage, off of stage. You have a different way of doing things. That's why I'm so excited you're going direct to the people with the Not Done podcast coming out August 19th. I'll include a link in the show notes so people can sign up. I'm so excited about this. Why do a podcast? Why go direct to the people, communicate directly with everyone who can learn from you on these things?

Sloan: That's a couple of reasons. One, I've always had a lot to say, but I had to be a little more controlled as CEO of a large company. And so the shackles are off, if you will. I love Remington. It's like my family. I'm not going to say negative things about them or Ashford, but I can now give a very strong opinion about how is AI going to disrupt without worrying about shareholder opinion or worried about this owner who doesn't want to invest in this technology. And the CEO just publicly said this, so it's going to impact my hotel this way. I don't have to worry about that. So a little bit of the shackles are off.

Secondly, it's a great way to learn. If you look at masters of any business or masters of art, they produce a lot of product. There's been studies done. There was, I forget the study, what it was called, but there was a pottery instructor that gave his students, he broke the class in half and he said, this side, you're going to do one immaculate piece and it's due at the end of the course and your entire grade is going to come from that. And then this side of the class, I want you to produce as many pieces of pottery and art you can in this course. And the side that had the most powerful pieces were the ones that did high volume because they were iterative and they didn't get caught up on, well, this has to be perfect. And so I feel like a podcast is that, that not each one's going to be perfect. My first episode might suck, but you get better and you learn and have these forward conversations. That's what I selfishly love to learn. Now the handcuffs are off, I can say what I want and it's a great forum. I look at people like you and what you've been able to do. Selfishly, I want some of that.