The Modern Hotelier #204: How Trailborn is Bringing Design-forward Hotels to Outdoor Destinations | with Michael Weiss
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David Millili: Welcome to The Modern Hotelier, the most engaged podcast in hospitality. Don't forget to follow, like, subscribe, and let us know in the comments what you think about today's episode. Steve, who do we have on the program today?
Steve Carran: Yeah, David, today we have on Mike Weiss. Mike is the co-founder of Trailborn. Mike is transferring outdoor hospitality and travel, creating experiences that connect people to nature without sacrificing the comfort or service. Trailor hotels are iconic outdoor destinations where they create beautiful spaces and local experiences designed to guide your adventure. Thanks for joining us, Mike. 
Michael Weiss: Great to be here guys. Thanks for having me.
Steve Carran: You bet.
David Millili: So Mike, we're gonna go through a quick lightning round, get to know you a little bit better, and then dive into some industry topics. Sound good? So what's something you wish you were better at?
Michael Weiss: Golf.
David Millili: What is your most used emoji?
Michael Weiss: Either the thumbs up or the pound
David Millili: Got it. What's a luxury you can't live without? All right. If you had a time machine. Are you going into the future or into the past? And what year are you going to?
Michael Weiss: Either going way in the past before I was born or into the future. I think reliving, like reliving Groundhog Day, I think would be a, a pretty bad existence.
David Millili: I hear you, what's the best piece of advice you've received?
Michael Weiss: Treat people the way you wanna be treated.
David Millili: And finally, what's your favorite city and why?
Michael Weiss: Ooh. I guess I have to go with New York. I'm born in New York, um, and I've lived in New York or around New York most of my life. And, uh, after experiencing New York, I, I go into other cities, just isn't the same.
Steve Carran: Well said. Well said, Mike. Well, you're leading right into this next section perfectly. We're gonna dive into your background a little bit and more. What makes you tick? So, as you just said, you grew up in New York. how did growing up in New York shape you into who you are today?
Michael Weiss: Good question. So I think when you're young in New York, you just get thrown right into it. I remember when I was a, it must have been like fourth or fifth grade, I started taking the public bus across. Town to school. Now I've got a 2-year-old daughter and a 4-year-old daughter, and I don't think I would ever put them on a public bus.
I think New York forces you to to kind of up your game a little bit and grow up a little bit faster. And, it's a competitive place. And so, I'm a fairly competitive person, so I think that's, that's how New York has shaped me. 
David Millili: And you majored in psychology from Cornell. You got your business MBA from Stanford. What made you choose those degree? Careers, sorry. And what really kind of led you to those schools?
Michael Weiss: So Cornell, it's funny, I'll tell you a story. My dad went to Cornell, his dad went to Cornell. My uncle went to Cornell. My cousins went to Cornell. And, uh, when it came time for, for me to pick a school, I played baseball in high school. I wanted to play baseball in college. I started doing the school tour and I went up and start, started going from place to place.
I met with the baseball coach. I did, you know, the campus tour. and then we kind of hit the road and moved on to the next one. And when I got to Cornell. My dad, who was very involved in the school, had me meet with the dean, had me meet with the athletic director, had me meet with the baseball coach toured me around. We stayed in the Statler Hotel, which is a great hotel on campus. and we basically spent three days there in Ithaca, whereas we spent about an hour in each of the other places. And then my dad was like, so where do you wanna go to school? And I was like, well, I know where you want me to go to school.
So, Luckily, I grew up going to Cornell, it's an awesome school just a really great education, a beautiful place, at least when there's not three feet of snow on the ground. and so I loved it there, and was lucky enough to get recruited to play baseball there as well. So it all worked out.
And then Stanford, you know, I feel like I'm like still pinching myself that, that I was able to go to Stanford. That campus is like, it's like a dream. And it's just one of the best places in the world to learn. You get people coming from all industries coming together who are just trying to advance their career and grow as people.
And it's amazing what that admissions office can do in terms of identifying really good people, not just smart people, not just successful people, but really good solid people. And so, some of my best friends in the world, are from Stanford, GSB. 
Steve Carran: Very cool. So this was something interesting that I found that you and Ben, your, uh, partner Ben Weinberg, actually were childhood buddies growing up, and you knew you wanted to go into business with each other. You just didn't know what you wanted to do. Can you talk about kind of maybe some of the ideas you had before trail born or just how you knew that he was the right person to go into business with? 
Michael Weiss: Yeah, so I guess to tweak what you said a little bit, we had known each other our whole lives. Socially. We had not worked together. And so going into this, we weren't positive that we wanted to spend the rest of our lives working together. So we actually had a pretty extensive period of time where we were meeting with each other, learning about each other, what our goals and ambitions were, what type of company we wanted to build, what we were both really passionate about, what we were both really good at, and so we had an extensive period of time where we were just trying to. Solidify that decision of are we the right partners for each other? Because as you guys know, the world changes, hospitality changes, real estate changes, businesses change. inevitably there, there will be change over time. We've already experienced some of that.
And so we made the decision that, let's make sure we're the right partners before we decide on, on any one single business idea. And then we can, we can work together to solve all of our problems from there. and so that's one of the best decisions I've ever made. and to answer your question on, on what some of our ideas were, you know, we were both passionate about real estate, passionate about hospitality, and wanted to build something that.
There was a real white space where we could have a competitive advantage in where we'd spend the rest of our lives, working on this idea and that kind of led us down a, a, a road of exploring different ideas in and around real estate and hospitality that ultimately landed us on Trailborn, which is our brand and management company, and Castle Peak, which is the investment arm
Steve Carran: Very cool. So now we're gonna dive into your career a little bit, how you got to where you are today. So, after college you worked at Goldman Sachs outta school, then you were one of the, one of the first. First people at Airbnb. I think you were one of the first 30 people there, during business school, and then you helped co-found Compass. What did those early days teach you that you still take with you today?
Michael Weiss: I mean, I feel very lucky to have been a part of all those things. Um, and you know, I think as is the case with, with most things in life, you don't know exactly where one thing is gonna lead you. And so coming out of undergrad, I was actually, you know, I was, I was, as you mentioned, Dave, I was at Cornell, but I was not in the hotel school.
I studied psychology and business undergrad. Didn't really know what I wanted to do when I grew up. and so graduating upon graduating, I just said, I'm gonna learn as much as I possibly can. And so I just threw myself straight into it. Investment banking at Goldman, um, and then eventually real estate private equity at Goldman.
And so, there, I just learned a ton about corporate finance, about how different businesses worked. I learned work ethic more than anything else, right? You, you kind of get your butt kicked. first few years of investment banking, Then, from there, I, uh, while I was working at Goldman, I helped start a nonprofit in my free time, like nights and weekends, helped build, build a nonprofit called Pence as a promise, which builds schools in developing countries.
And that's what really got me excited about entrepreneurship and building businesses. So I went out to Stanford to, to kind of make that shift and, and move towards, startups and company building and was very lucky to find Airbnb, while I was there at school. And so Airbnb, I think they had just raised their series B round, and there was like 30 or something people there, as you said, Steve and it was just a great place to get exposed to what it means to actually create and build something. what product is really about right. The two of the three founders are, are product and design focused people. So getting exposure to that was a great experience for me. and so I love my time there and then was, was lucky to come back to New York and, and co-found Compass and run the product team there at Compass.
And so I think the theme through all of those is I like to work on consumer problems where there's a big white space and solving something that I'm personally passionate about that's a consumer, consumer need. and I think that  a lot of those learnings made it possible for us to do what we're doing today.
David Millili: You're answering some of the next question a little bit. We're gonna go through it again, but you've, you've co-founded such a diverse. Range of ventures. So you mentioned Pencils of Promise, rise Brewing Company, castle Peak Holdings, trail Born. Take us a little deeper into what drives you to those and what do you look for that really gets you excited about, you know, starting something like that.
Michael Weiss: I mean, I think any good business starts with a real consumer problem or white space in a market, and so I personally, I'm less of a B2B person, right? I like consumer businesses. I like things that I can experience myself, where I can go and talk to someone and understand what their problem is, what their need is, and identify a real opportunity.
And so I think that's true of all of those, right? With compass is entering into the brokerage industry, which before we got started, was a very slow, tired industry without a lot of technology, low NPS score. Not a lot of people were happy with their real estate brokerage transactions.
And so, those things combined where people aren't happy with a product, it's not really leveraging technology, there's an opportunity for improvement, are the types of things that I like to work on. Airbnb created a whole new market themselves. Now they're one of the largest hospitality businesses in the world, and then Maple, which is where I went after Compass, similarly, was trying to deliver restaurant quality food to your door in under 30 minutes. that's a product that a lot of people can touch, a lot of people can, can feel. and I joined an incredible team there that was, that that was a fun consumer challenge to solve as well. 
Steve Carran: So I heard through the grapevine that you got the idea to start trail born while you were staying at a very mediocre, probably a little bit too expensive hotel in Estes Park. Is that true?
Michael Weiss: Yeah, that was one of the key moments. It was an evolution, like basically building the idea. But was one of the kind of light bulb moments for us where we were in Estes Park staying in a select service product and paying a lot of money, not really having the experience that we were looking for. And so that was one of those light bulb moments.
Steve Carran: Yeah. And is that, how did you decide to focus more on the outdoor space? Compared to a traditional hotel that is, you know, more in the city.
Michael Weiss: Yeah, like I said, we wanted to find something that we had a competitive edge in. and right macro trends were behind us. And so outdoor travel has been growing. It's something that people like spending their money on, they will continue spending their money on. It's something that Ben and I are personally really interested and passionate about.
We both love the outdoors. we both have young families that we want to take to the outdoors. and if we were to, you know, the two of us. If we were to go try and buy a 500 key property in Midtown Manhattan, like we just, didn't have a competitive edge there, right? There's a lot of other people focused on that product.
There's a lot of other people trying to do that. Whereas we found an opportunity in these markets. It's much harder to find deals in these markets. It's a lot more travel to travel all over the country, but we're actually doing something that we have a competitive edge 'cause it's. All we focus on. And that focus for us really helps us win deals and build a product that's purpose built for our customer which is why we decided to do it. 
David Millili: For those who are watching or listening who aren't familiar with trail borne, can you take us through a little deeper dive into what Trail Born's all about? 
Michael Weiss: Yeah, so Trailborn is a brand and management company that, exclusively operates what I'll call four star Hotels in outdoor destination markets. That includes wine, country, national park markets, beach markets, ski markets. Anywhere where there is an outdoor draw, an outdoor activity that people wanna go to that destination for.
So most of our markets, there's already millions of people traveling there, but they don't have a hotel that's design forward. They don't have a hotel that that has great design. They don't have a hotel that has, programming on site. and so we've. tried to solve that need by, by building Trailborn as the brand that is solely focused on these outdoor destinations. 
Steve Carran: That's great. So now we're gonna dive into some thought leadership topics and really what's happening in outdoor hospitality. So, now is kind of an interesting time in the outdoor hospitality space. How has it shaped the product you've built and I guess why is it an interesting time in this space?
Michael Weiss: I think, I mean, listen COVID was a piece of this puzzle, but people were traveling the outdoors long before COVID. I think COVID opened people's eyes, that weren't traveling outdoors. So like, wow, there's great places to go here in the us. I don't need to get on a plane and fly to another country to, to see some beautiful places and, and get myself and my family outdoors.
And so I think outdoor hospitality has, has almost doubled over the last seven years. and people wanna spend their money on things and on experiences, not on things. And so I think like three quarters of, the country would rather spend their money on going to an experience, outdoor hospitality being one of those things.
And so that presents a lot of like strong demand trends, for the space. And like I was saying earlier, like the, there, there are real supply constraints, um, in this market, right? You're not going into a place where you can build an endless number of keys. And so, that supply demand mismatch makes us a really compelling real estate opportunity and the fact that most of these outdoor destinations don't have a boutique design forward brand makes it a really compelling consumer opportunity.
David Millili: Yeah, and you talked about all the different, you know, locations and, and, and types of destinations your properties are in. How do you balance localization and then the consistency across different types of properties?
Michael Weiss: Yeah, that's a great question. For us, we have a set of pillars that every trail born stands stands behind. And so when you go to a trail born, you know it's gonna be a destination worth traveling to, you know, it's gonna be beautifully designed, uh, four star product. You know, there's gonna be programming on site that makes it fun and makes it the kind of place that you can actually enjoy on property, not just out in the destination.
You know that we're gonna guide your experience because we have a team of experts that are. Super passionate about the places that you're traveling to. So when you go to the Grand Canyon, you've got a team of people who have been to the Grand Canyon a bunch of times, who know all the best places to go have all those insider tips.
And then, food and beverage, every one of our properties has great food and beverage, which is not always the case in these markets. Most of these markets don't have great food and beverage. and so those are things that we try and keep consistent from place to place the way that those come to life is unique for each property. So, everything from our room design to our lobby design to our uniforms, to the programs that we put on property are all designed to be of the place. And so when you travel to the Grand Canyon and you're on Route 66, you feel like you are in the, in, you know, Americana, like right there on, on Route 66 when you travel to Wrightsville Beach.
You don't feel like you're in a mountain resort or in the desert. You feel like you are on at a beach resort, a design forward and fun beach resort. And so, that's really important because the person, the customer that's traveling to all these places, they don't want a cookie cutter experience, right? This is predominantly leisure travel. They want to feel like they're really experiencing the destination. 
Steve Carran: And you signed a long-term deal with Marriott, and Marriott is now kind of, is focusing a little bit more towards the outdoor. Collection, what does that unlock for? Trail war.
Michael Weiss: I mean for us, we're really excited about this agreement with Marriott. It, it's sort of the best of both worlds for us because we can continue building the product and the experience and control that product and experience that we've spent the last five years building. but we now are partnered with Marriott, who is the largest hotel company in the world that has 230 million Bonvoy members that are all looking to get outdoors, that are looking for a product like ours.
And so, I think it's great for Marriott and it's. It's great for Bonvoy members and it's great for us because, we can bring that product to a wider audience now.
David Millili: So take us through, you've got the trail born, Grand Canyon just touched on it a little bit before. Why is it such a meaningful addition to the portfolio and what does it mean or how does it really reflect on the brand's broader vision?
Michael Weiss: I think for us, we bring people to basically two types of markets. We bring people to what we'll call regional gems. So like Wrightsville Beach and Highlands North Carolina are places that if you live in the Southeast, you've probably heard of those places. If you live anywhere else in the country, you may not have but if anyone were to go in step. In those markets, you, you would be wowed, you'd be like, wow, I can't believe I have not heard of this place. This is a, an amazing place that I wish I had traveled to a long time ago. and so introducing people to those regional gems is something that we take pride in and is like a fun part of the Trail war experience.
The other part of the trail war experience is taking people to places where. Millions of people are already going where it's on their bucket list and they just don't have the hotel product that they're looking for. And so, the Grand Canyon squarely fits into that, right? We are there's 6 million people that go to the South Ram of the Grand Canyon every year.
And there wasn't a hotel like ours in the market. And so, it very much fits what Trail Born is all about, bringing a unique, and boutique product to these. Amazing outdoor destinations. we're right on Route 66, so, you get like a true American experience and we're at one of the seven wonders of the world.
I mean, this is like everyone at some point in their lifetime should go, and see the Grand Canyon. and now you've got a good place to stay when you do it.
Steve Carran: Fantastic. Fantastic. So Mike, question for you here, what advice would you give to, you know, maybe somebody who's looking to start their own brand in hospitality, specifically outdoors or just looking to kind of be an entrepreneur like yourself? 
Michael Weiss: I'd recommend depending on, on what they were trying to build having a partner for me has been crucial. and when you start a business, you go through a lot of ups. You go through a lot of downs, um, and having someone that you can turn to every single day and make big decisions with and brainstorm with and, uh, celebrate with and, you know, console when needed to like that, that is has been super important for me. I think Ben would probably say the same thing. but I'm very lucky that I've found a, a partner that I have a good, that we compliment each other, we push each other, um, and we, we share those same big picture goals. So my advice would be find a partner, find a partner that you are aligned with on the big picture stuff, but that you're pretty different from on the day to day.
Steve Carran: Well said. I like that. I like that. So, uh, Mike, this has been great. We've been asking you questions this whole time, so now we're gonna turn the tables. And let you ask David and I a question. 
Michael Weiss: Let's talk about AI for a second, and I'm sure you guys have a lot of people that tell you, they're doing one thing or another with ai. And so I'm curious, what you guys think, is actually gonna stick when it comes to AI and how brands are gonna be successful in integrating AI into their experience while still keeping it personal and making it feel like a true hospitality experience. I think this is one of the few industries, left where there's like a real human component that needs to remain, but inevitably AI is gonna be a piece of it. So how do you see that fitting in? 
Steve Carran: You know, I think AI, like you said, we still need people. I don't think many people want to go into a hotel where everything's automated and there's really no human action. It's just done by ai. But I do think it'll help. Hoteliers automate mundane tasks where they can focus more on the hospitality experience.
I'll give one example that happened to me is I called a hotel and nobody picked up. The phone just kept ringing and ringing. I think in that aspect, we've actually had a few people on the podcast where they have had, whether call centers or even AI answering that front desk and mostly can handle all those requests.
And if not, guess what? Then we bring in somebody if they need more help or something like that. So I think, you know. Automating those tasks to help focus on the hotel area is really where AI is gonna stick. I do think, you know, there is gonna be this niche where it is fully automated on technology and that's what people want.
They don't wanna deal with the front desk, they don't wanna wait. They wanna walk into a hotel, get a mobile key, you know, and, and be on their way. But I think for the most part, it's just gonna free up hot, free, up time for hoteliers to provide a better experience.
Michael Weiss: Okay. Can I ask you one more, one more question. If you could put a trail born anywhere in the country, what, what, where would you want a trail borne to go?
Steve Carran: Oh my goodness, great question. David, you got an idea for this one?
David Millili: I don't know where, I don't know all your current locations, but one area that we're gonna actually as a family spend, I'm in Phoenix, so we're gonna spend it in Sedona. We're doing an Airbnb, um, in Sedona with great views and everything. I like hotels a little bit more than Airbnbs, so I don't know if you're in that destination, but that's just one of those spots where I just love going to Sedona.
Steve Carran: Fair enough. I'm going my hometown state here. I'm saying Wisconsin. I think Wisconsin's very underrated as far as the beauty that's there, whether it's a lake or, you know, the beautiful scenery that's there. We have some awesome state parks. and you know what? Whenever I go to Wisconsin and I want to go visit those places, the quality of hotels in a lot of them just aren't there.
It's kind of like what you ran into at Estes Park where you'll stay at one of these maybe two, three star hotels and you're like, man, this trip would be 10 times better if I had a trail board there. So I think there's a lot. I think Wisconsin just has so much opportunity for hoteliers and it's now being considered one of the top states to live in, in the United States. So I think we're gonna see a lot more Wisconsin in the next decade or so.
Michael Weiss: Yeah. Great.
Steve Carran: Cool. Well, our producer, Jon, also a Midwest boy, has been sitting and listening this whole time as well. So, John, we're gonna kick it over to you to ask Mike one more question before we get him outta here.
Jon Bumhoffer: Yeah, for sure. Mike, I'm gonna throw Michigan in the ring for Trailborn somewhere along the Great Lakes. There's so many good coastline places to choose from. So I think that that could be in the running there somewhere. One thing I was going through your whole, whole portfolio, like looking at everything that the you, you kept saying design forward and beautiful and boutique and, and I was looking through everything and it is really well designed.
Like I just found myself being like, man, I would love to just be in that space it just feels really good. So I'm curious. You didn't really talk too much about where those design elements come from or how those come to be or where they're influenced. So I wonder if you could speak to that, like how did you guys land on some of these design elements? What do you think makes your design unique and special for Trailborn?
Michael Weiss: Thanks for asking, Jon. We invest a ton in creative and design. We have our own team in house that, whenever we get into a new project, we do all of our concept work upfront before we hire any other partners. And so we do that concept work to make sure we have a clear vision on what it is we're trying to create that takes interviewing locals, interviewing the current staff, really surveying the market to see where the white space is and what that customer that's traveling there is looking for. and then we have a creative team that starts to pull together a whole concept deck, which I think is unique. Usually you go and hire a designer who puts a concept at. Deck deck together. but what we've found is that if you want the product to look like, look and feel like how you envisioned it, the more work you can do upfront to make sure that those design partners are, are sprinting in the right direction, it'll not only make the product better, but make the whole process a lot more efficient.
And so we do our concept work. We then find an interior design partner that fits the type of design that we are trying to. to bring to life. and then we work very closely, hand in hand with those partners, them driving the, the bus on the interior design with some of our help, and then us driving the bus on a lot of the other brand elements like signage and artwork and programming and uniforms and that collaboration really delivers a, uh, a really cohesive product, at the end of it.
David Millili: Well, that does it for another episode of The Modern Hotelier, Mike. This is where you get to let people know how they can reach out to you and how they can find out more about trail borne.
Michael Weiss: Sure you could come to our website trailborn.com or follow us on Instagram @trailbornhotels
David Millili: Well, that does it for another episode of The Modern Hotelier, the Most engaged podcast in hospitality. Whether you're watching or listening, we appreciate you and hope to see you again soon. Thanks for joining us, Mike.
Michael Weiss: Great. Thanks for having me guys.