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The Unchecked-In goes beyond a traditional podcast—it’s a raw, unfiltered space where independent hotel owners get real about what it actually takes to survive, grow, and stay sane in the hospitality business.
The Unchecked-In will explore critical themes in independent hospitality, including:
Revenue Optimization Strategies: How small properties can compete with larger chains through smart pricing and positioning
Guest Experience Innovation: Creating memorable stays that drive loyalty and word-of-mouth marketing
Technology Integration: Leveraging AI and automation to streamline operations without losing the personal touch
Succession Planning: Preparing the next generation of hospitality leaders and ensuring business continuity
Market Positioning: Standing out in a crowded marketplace dominated by large chains and vacation rental platforms
Each episode will feature candid conversations with successful property owners, industry experts, and hospitality innovators who are pushing boundaries and creating exceptional guest experiences. From family-run bed and breakfasts to boutique glamping retreats, the podcast will showcase the diverse landscape of independent hospitality.
The Unchecked-In Podcast #09: Building A Hotel Brand for Outdoor Leisure Markets | with Keir Weimer & Jonny Jost of Weekender Hotels
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Bobby Marhamat: Hey everyone. Thanks for listening to another episode of The Unchecked-In Podcast where you get real. With the people actually running independent hotels. No fluff, no filters, just the wins, screw-ups, and the lessons that we wish someone told us sooner. I'm Bobby Marhamat. And today I'm sitting down with two guys who are not just building hotels, they're building a whole point of view around outdoor markets and what a great stay should actually feel like.
First up is Keir Weimer.
He is the CEO of Northbound Capital and the founder of Weekender. Keir's been an entrepreneur since he started his first company out of a Santa Cruz dorm room. Here's a fun one. He's never taken a paycheck or been a W2 employee.
He's got a master's in real estate Finance from NYU. Spent years as the number one luxury broker in this region, and built different businesses, which we'll talk about today. And then went all in on hospitality. Now he's focused on scaling Weekender, a fast-growing outdoor hospitality and experiences brand built around Adventure Place and travel differently, with him.
Jonny Jost? Yes. You got the last name right this time. Okay, cool. Perfect. Okay.
Jonny Jost: Perfect.
Bobby Marhamat: Investor and director of growth at Northbound Capital and Weekender Hotels. Jonny comes to us with a real operator's brain. He spent more than 15 years inside founder-led and family-owned businesses, including running a portfolio of Planet Fitness franchises, which I would love to talk about, as well as a managing partner at Jost ADK.
He's been deep in operations, marketing, development, construction, finance, legal, all of it, and big on building systems at scale without killing the culture or the soul of the business. Gentlemen, welcome to the show.
Keir Weimer: Thanks for having us.
Jonny Jost: Thanks for having us, Bobby. Happy to be here.
Bobby Marhamat: Absolutely. Happy to have you guys. I know the two of you through EO, as I've learned. I've read a lot about you. Grew up together in the same outdoor leisure markets and now invest in operating hotels. Take us back to the early years. What was it like being kids on the lake and the mountains and quietly teaching yourself about community and why people travel?
Keir Weimer: I'll jump in. And then Jonny add, because we share a similar background and experience. We're happy to be here, share our story, talk about what inspired us to do this and what brought us to where we are today and being on the show. We've known each other for probably 20 years. Grew up together, maybe even longer than 25 years. Met in high school. Our families were in the same area. We vacationed in the same spot. It's a 6 million acre state park in upstate New York called the Adirondack Park, and it's a special place.
It's an outdoor mecca. We grew up on the water. Starting our days doing dock start, single skis, wakeboarding, wake surfing, rafting in the rivers, hiking on the high peaks in the mountains, going to summer camp, and learning outdoor skills. And at its core an appreciation for the outdoors and a love for what it means to build a life with that at the center.
Fast forward, a lot happened in both of our lives. Jonny moved out West to Colorado. I went through hard stuff in my twenties. We reunited in the summer of 2012, about 13 going on 14 years ago, which is crazy. At that point we're both charting a new chapter. What's next? What do we want to do? We went through life experiences that taught us lessons and got us focused on getting serious about building something of merit and legacy.
He started exploring the option of buying a franchise territory with his brothers in Planet Fitness, which became a double digit portfolio out in the greater Denver and Colorado Springs area. I started as a broker of luxury high-end real estate with Sotheby's International Realty and got my start in real estate that way. I always knew that I wanted to get into ownership, investment, development, and operation and ended up buying a first resort that would later become the flagship and part of the inception story of Weekender.
Closed on a 30 room waterfront resort, a hundred year old story in fall of 2015, about 10 years ago now. I was the listing broker on it. Couldn't find a buyer. Ended up recruiting two friends from Manhattan to run the day to day and have a minority equity interest in it. We learned a lot. We failed a lot. We didn't make any money until year three, but we figured it out. We were open to being coachable through life lessons, the demands of being in business at that scale and surrounding ourselves with the right people.
We created something special. It became an award-winning destination resort. To this day it's the nicest, most curated experiential place to stay in a 40, 50 mile radius. It's the highest ADR resort in the area, market leader on RevPAR. It's the destination for weddings, events, outdoor travel, restaurant, 600 feet of waterfront, awesome backdrop and settings.
That was the start in hospitality for me. I won't bore you from that point until COVID, when that started to shake things in the industry and in my own psyche as to what led to the founding of Weekender in 2021. We can get to that later. Jonny, what do you want to add? Maybe some of the stuff we used to get into, because we got into trouble growing up.
Jonny Jost: I think Keir's family is similar to mine. We are four generations into the Adirondacks, the Old Forge area, including my kids and my nieces and nephews. So four generations. Keir, you're probably four generations now.
Keir Weimer: Yeah.
Jonny Jost: Spending time.
Keir Weimer: Up there I spent every weekend, every summer there. As a kid, growing up in an outdoor leisure market equals freedom. You get up in the morning, get on your bikes, find as many friends as you can, and you're either going to the water park or trying to figure out how much trouble you can cause building forts along the rivers, catching bullfrogs and living a wild and free childhood. It was amazing. I wouldn't want to have been raised any other way.
Jonny Jost: You get your first summer jobs. My dad, as soon as you were 14, the legal age to have a job in New York, you had to have a summer job no matter what. That was everything from working at the local water and theme park in Old Forge to working at the marinas, getting introduced to guiding whitewater rafting, cutting lawns, and working at one of the biggest outdoor retail outfitters in the Adirondacks, Mountain Man, dealing with rentals.
Really learning at an early age how these markets trade and what the expectations of guests are and how to provide that guest experience. My first business was before I was old enough to work. When I was 12 years old, we knew where all the bears were in town. Tourists loved to find the bears. We figured out a way to monetize. We knew where they were. We knew the tourists wanted to see them, so we charged a dollar a head to take them into the places where they were.
Bobby Marhamat: Oh man.
Jonny Jost: That went on for a few weeks until my mom figured out what we were doing and shut it down. She did fill the van with all the guests and gave them the experience we promised, and then we shut things down. It teaches you how to hustle at a young age, living in an outdoor leisure market, while having the most fun no matter the season or the weather.
Bobby Marhamat: And make money from it. I love it.
Keir Weimer: Yeah.
Jonny Jost: Right.
Bobby Marhamat: How do you feel like that experience has led you to create the highest ADR, good creation of activities and experiences within your hospitality properties? How has that contributed to that?
Keir Weimer: I think the proximity that our locations are to outdoor amenities and demand drivers, state and national parks, amazing skiing, snowshoeing, snowmobiling, world-class water sports, hiking, mountain biking, rafting, golf, small towns with great retail and restaurants. Location is a critical part of real estate. Locating your assets close to where your target customer wants to be is step one.
Two, making sure your experience on property is aligned with your brand promise. For us that's providing a safe, comfortable, renovated, tech-enabled stay that's easy for guests to enjoy and feel like it's a second home, a base camp, but also a jumping off point where they don't have to spend all their time on property. They can go out and recreate within 20 minutes of the property.
Then leading into programming and curation as a thought leader and connector. Not necessarily being the in-house guide for everything, but having the best recommendations. The best hikes for sunset, the best trails for an elderly couple versus a couple in their twenties. The best outfitter, the best part of the Moose River to kayak, the best time to raft the Hudson.
That packages into a guest experience that we think is different and above what competitors offer and what a guest might expect for the price. We're a pretty affordable brand offering a renovated, safe, tech-enabled, well located stay. We're around 200 and change ADR across the portfolio in summer. High weekends are 3, 4, 500. Some cabins get up to a thousand a night. Off season Tuesday, Wednesday in November or April might be 40. So we're approachable.
Bobby Marhamat: Definitely.
Jonny Jost: I would add celebrating the community and the through line to the properties. Old Forge was a big logging area that moved into a recreation area in the 1800s before the Rocky Mountain West was explored. You had great camps, rustic properties. As time evolved, like Keir's first hotel, Great Pines, a hundred year old hotel, went through evolutions. The design harkens back to the original great camp times and gives guests that through line.
Same in Lake Placid, celebrating the Olympics. Two major Olympics. A town that used the Olympics as a long-term economic driver.
Bobby Marhamat: Makes sense. You guys are about 10 years in, about 10 properties.
Keir Weimer: As Weekender we're about five years in. We started in March of 21. Great Pines was an outlier. I was still doing brokerage full time, multifamily stuff, started a venture-backed hospitality marketplace, then COVID hit. I saw an opportunity shift away from big brand corporate to indie upstart and toward outdoor focused leisure.
That blew wind in the sails to take what we did at Great Pines and build a portfolio and brand around it. We went on a big acquisition sprint for a year and a half until interest rates rose. We slowed down, did four deals over the last 24 months, and now we're ramping up growth again because debt costs have come down and sellers are more realistic and creative.
We're about to close on our 11th hotel. It'll be our first outside the northeast, first out west. We're moving into a dual market focus. Filling in the northeast and expanding in Colorado and surrounding Rocky Mountain states.
Bobby Marhamat: That's awesome.
Keir Weimer: Thanks.
Bobby Marhamat: What do you look for? When do you know a property should be part of the Weekender portfolio?
Keir Weimer: There's a qualitative and quantitative component. It starts at region and market, drills down to properties that fit our criteria, then what's available or off market. About half our properties were off market, which helped our unit economics.
High level, it has to be within two hours of millions of people in a major metropolitan drive-to market. In an outdoor leisure market busy at least two and a half seasons. Baseline occupancy 50 percent or higher with good ADR and RevPAR trajectory. We look for laggards underperforming their comp set, undercapitalized, older mom and pop where kids don't want to take it over. There's transition and arbitrage opportunity.
Bobby Marhamat: What are red flags?
Keir Weimer: Market and physical structure. We won't do transit oriented interstate three level box product. Hard no. Too big, too corporate, 200 rooms and up, hard no. Too small, 20 to 30 rooms and under moving forward, hard no.
Valuation per key, operational and renovation upside must have enough meat on the bone to execute our value add strategy. It has to be brandable after renovation. Usually it's far below what we'd put our name on. We renovate everything we buy.
Bobby Marhamat: Let's talk screw ups. Early decision that didn't work out. Jonny?
Jonny Jost: Joining Northbound Capital recently, early on how we operated discovery calls. I'm engaging and like to get to know people, but needed to structure calls more strategically. Getting upfront what available capital looks like, allocation, timing, qualifying factors so we're not wasting time and finding alignment.
We brought on coaches to dial in discovery calls and capital markets process.
Bobby Marhamat: Money's easier than finding aligned partners.
Keir Weimer: Two things I'd change. I would've looked at larger properties earlier and not grown the corporate function as quickly. That created constraint on cashflow and working capital. We built infrastructure to scale three to four deals a year, then rates punched us. We weathered it and still acquired four deals, but it came with a price.
Also realizing it's hard to build a big brand at scale with 20 to 30 key properties. The math doesn't work. Now we look at minimum 40 to 50 keys up to 150 without losing character and intimacy.
Bobby Marhamat: Aspirations? Five or ten years?
Keir Weimer: Five year vision, 7 to 12 states, 30 to 40 properties, one or two sister brands, Northbound Capital on fund three or four. Scaled infrastructure, team, tech stack, repeatable process, slightly more institutional without losing character. Larger, more amenitized, higher service level.
Probably 500 to 700 employees. Keeping Northbound lean, embracing AI and process to manage money at scale without heavy overhead.
Bobby Marhamat: Great segue into AI and tech. How do you balance experience with tech?
Keir Weimer: Provide amenities and technology people are accustomed to at home or better, but not make it the focus. Laser fast fiber, preloaded streaming apps, easy device casting. In-room experience fast and easy. Automated check-in by text, wifi locks, wifi thermostats, voice enabled rooms for weather, ski conditions, restaurants.
Not in your face. Supporting player that makes you feel at home while allowing you to disconnect outside and come back to comfort.
Jonny Jost: In a more digital world, people will be intentional about disconnecting like they are about exercise. We use AI to enhance guest experience, get them in and comfortable, then get them outside exploring and starting a digital detox if that's their intention.
Bobby Marhamat: For folks in the messy middle trying to grow, what's one lesson you'd tell your younger self?
Keir Weimer: Get clear on what you want to build and merge professional work with personal values. Create an approach to life where you love Mondays and are sad to see Fridays. It takes false starts. I started different businesses that moved me toward schedule control, financial independence, calculated risks.
Take risks when you're young. Fail forward. Like a kid falling off a bike. At 70 you go to the hospital. Take calculated risks, bet on yourself, go after professional and personal alignment early.
Bobby Marhamat: How about you, Jonny?
Jonny Jost: Work life integration. We get to do this every day. Provide health, wellness, and experiences in places we love. It wasn't easy. Work on your business, not always in it. People, process, product. Systems run the business. People run the systems. Right people, right systems, right product tied to mission and vision.
Find someone doing what you want to do better than you. Look for mentors. In the franchise world I could visit others and learn. In any industry, if someone loves what they do and does it well, they'll share.
When I had three clubs at 30, I was running around because I didn't have the right people, processes, systems, culture, leadership development. Once that flipped, things became more integrated and enjoyable.
Bobby Marhamat: Easier and more fun. I can talk all day, but that's our time. If people want to follow your work, where should they go?
Keir Weimer: Best place is our websites, weekenderhotels.com or northbound-capital.com. Fill out a contact form. Jonny and I are on LinkedIn, Keir Weimer and Jonny Jost. Reach out. We're happy to connect and share value with peers and people in the industry.
Bobby Marhamat: Amazing. Thank you.
Jonny Jost: Thanks for having us, Bobby.
Keir Weimer: Thanks.