Co-Hosts Mateo Bradford and John Stokinger get real with Cliff Johnson VP of New Homes at Reatlor.com. Most of you know Cliff’s story… Vacasa Co-Founder to Rented Chief Commercial Officer to now the VP of New Homes at Realtor.com.  Although Cliff has left the vacation rental space in which he has solidified himself as a first-ballot shoo-in in the Short-term Rental Hall of Fame, he wants you to know that he is not dead and no need to send flowers. We talk about his current role, future ambitions, regrets, humble beginnings, and his feelings on the news that Vacasa will be publically listed with a 4.5 Billion dollar evaluation. An amazing conversation with one of the brightest and most thoughtful minds in our industry. The No BS Short Term Rental Podcast brings the right people to the table at the right time giving their audience an inside view and real take on the industry like no other. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Practicing Standardized Flexibility With Featured Guest Cliff Johnson

Normally we start this off with a morning, Teo but it is not morning. We waited until evening to accommodate somebody. I don’t know who but Teo, how are you doing?

Fantastic. It is another beautiful hot day in Atlanta. I’m out here sweating my head off. How are you?

It was humid here.

We got to talk about your tank top at some point in time. It is going to be interesting. If people haven’t been watching the YouTube channel or the video, they have to watch this because you have to see John’s tank top. Honestly, that is the first time I have seen your full tattoo sleeve.

I got a little bit going on.

See what happens when you go on vacation. It is a whole new you.

It is a workcation but not work. It’s a demo in the kitchen. I did the laundry room but it needs to be done. Happy wife, happy life. This kitchen needs to be a priority and now we are prioritizing it. I’m exhausted.

You have been putting at work. I saw the pictures. You are better than me because I would be like, “These contractors are horrible. Who could we get to do this kitchen for us?” That is awesome. I can’t wait to see what it looks like.

I’m excited and Misty is excited too. It is going to be good when it is all said and done. We did accommodate. I will let you go ahead and introduce our guest.

I’m honored to have a good friend, someone I consider my brother, a mentor and someone I’ve learned so much about this industry and enjoyed life lessons with, my good friend and brother, Cliff Johnson.

Thank you, Mateo.

I’m so happy to have you. For most people, you know who Cliff Johnson is. At what stage do you know Cliff Johnson? It might be a different story. He is the Cofounder of Vacasa. He is the mind behind the brilliant products that Rented has put out around their wonderful revenue management tools and the addition to the Realtor.com family, who is doing some exciting things. I don’t want to steal his thunder. I’m going to let him talk about where he is and what he is doing. John, you also got the, “Is Cliff leaving the industry? He is calling the Realtor.” The best thing that we can do to kill all that noise is to let Cliff tell the story for himself.

Thanks for joining us.

Thanks for coming on, Cliff.

Thanks for having me. It is a pleasure to be here. Mateo, you know how much I have a hard time with compliments but thanks for all those and right back at you. I have learned a ton from you and continue to all the time. There are so many fun things happening in the vacation rental world. I had this interesting opportunity. Thanks to cofounding Vacasa, launching that and growing that.

I have been fortunate to get a lot of opportunities to come through over the years. I never had one tempting enough to leave the vacation rental world that I love. This was a unique one where I got to run a startup within a large company with great resources and talent in Realtor.com. I’m working with a great team to build the new construction side of the business from the ground up.

What that means is we are working with builders all over the country. We are working on improving the builder experience and how to get their listings onto Realtor.com but also working on the consumer side. It is an area that is a scary thing for a lot of consumers to think about buying a new home for whatever reason. It is less common for people to think they can afford it or even understand the process of buying a new home versus buying an existing home. It is something that I have been diving deep in and learning a ton.

There are many parallels between vacation rental management and builders. There is this deep local expertise that builders have about the markets and communities they work in. The same is true on the vacation home manager side. The areas where I’m going to be able to help them are similar to what we were able to do in vacation rentals. It is looking at the tech stack. What are they doing? How can we help improve that? We are looking at the data. What data do they need to make better decisions?

Those are things that I’m soaking up as much knowledge as I can and learning on that side. I’m looking forward to helping deliver more of those solutions and bringing this new area that I’m learning. I’m bringing along the vacation rental side and thinking about how to integrate vacation rentals onto some of these large real estate platforms.

Realtor.com is the original. They started in 1996. They have always partnered closely with brokers and agents. That connection is still deeply there. We are looking at how we work with all sorts of partners to deliver a better consumer experience. One of the things that resonated with me is I got to meet the CEO David Doctorow early on in my interview process. He is a purpose-driven leader. He sees the Realtor.com platform as an opportunity to help people find their first home in an easier way that is less painful and scary. How do they get their mortgage? How do they qualify for a mortgage? How do we make sure that people can move from becoming a renter to a homeowner in a seamless process?

As part of that, we are committed to fair housing specifically. We are looking at how we make sure that people have fair access to housing. There are a lot of fun and exciting things going on. I hope to come back maybe 6 months or 1 year from 2021 and talk about some of the cool things we have done but a lot of those written works.

You are in Realtor.com. There are some big competitors out there. Realtor.com is the original but there are Zillow and all these other ones out there. You are coming to this builder startup for Realtor.com. Are Zillow and some of the other competitors doing similar things? Are you still in direct competition? Are you pioneering this ahead of them?

Zillow and BDX are the two biggest competitors. The interesting thing is that BDX is owned by a consortium of builders and was a longtime partner of Realtor.com. That relationship ended in February 2021. That is a different competitor than Zillow, where Zillow is more directly competitive with Realtor.com across the board.

One big difference is that they are in the iBuying space and we are not. Something positive for most of our partners is that we are not competing on that side. There are going to be a lot of things that we look at as this landscape continues to unfold. There are so many opportunities. Real estate touches many areas. If you look at the potential for us to grow rentals or the mortgage side and all these different areas that are integrated with real estate buying and selling, there is a lot of room to improve across the board.

Whoever delivers the best consumer experience for buyers, sellers, tenants, landlords and all the categories, in my case, builders, home buyers, agents and brokers that work with them, a lot of it comes down to consumer experience. If you look at where companies have made gains over the last several years in real estate, it has been delivering a better and simpler experience with a more positive outcome. Zillow is our biggest competitor but it is not one-to-one on everything. We are offering different ways to get there for buyers.

It is almost like a blank slate to map a way of getting people into homes. It is a huge issue. At the end of the day, you think even within our lifetimes. We work within the vacation rental industry. We are always around people’s 2nd or 3rd properties or depending on who they are. They got dozens or hundreds. When you look at the grand scheme of housing in this country and that conversation, we are smack dab in the middle of it from the STR space. Having to have this conversation, especially in urban areas, how do these two worlds live together? How do places like Atlanta used to be relatively affordable but are not that way anymore?

Even selling starter homes. People are coming in. You got flippers and people that are competing with these first-time home buyers who are coming into the market at its most expensive time in our history. It is a hell of a problem to look at and solve. I’m excited to know that mine was like Cliff’s and other people are thinking of new and tech-driven ways to make sure that this is a reality for people here in this country because that is a huge thing. People’s first home is a huge thing.

We take that a little bit for granted because we are used to working on the business side of vacation rentals and STR but sometimes that does get overlooked. I’m excited to see what you do. There are lots of room. For marriage, there are lots of room to work together to solve this problem. I hope everything from the regulatory issues to how we make this more equitable for people is something that you are able to do. I know we are not losing you but it is a great opportunity. We are excited and we will have you back on to hear how things are going.

On that note, I am staying on as a board member at Rented. We will continue to work with Andrew and the team to advance the strategic direction of the company. It was funny at first when the news Amy published an article. Everybody was like, “We are going to miss you.” It was Amy that said, “It does feel almost like you passed away the way you are getting it.” I was like, “It does feel like that.” I didn’t leave. I’m still on the VRMA and Rented board. I’m going to be working in the industry, not in a full-time capacity.

The knowledge I’m gaining at Realtor.com is only going to enhance my ability to help the industry, especially when it comes to the regulatory side and having a different lens on affordable housing, which is an issue that is near and dear to me. Not everybody knows this. I’m going to tell you. You know it quite well. I grew up in a lower-middle-class family, figuring out things month to month. I didn’t own a home until I was 32. I never had the means to be able to do it. I lived in places where it was unaffordable. I lived in Boston and Denver, which seems cheap. Looking back on it, I should have bought a home there but I couldn’t. I went to San Francisco and Portland. It took me a while. Portland became a hot market. It was ahead of the curve for a bit.

I feel the pain of people who feel like they can’t get that first property or even find an affordable rental. In our industry, we see the other side of that, which is we depend on a lot of great team members, particularly housekeepers, to work in the markets and take care of these homes that people enjoy. We got to think about their quality of life. Are we providing a living wage? Are we providing adequate housing? What are we doing about that?

On the regulatory front, there is often a mismatch with the understanding of regulators that it is the vacation rentals that are taking affordable housing. In reality, a lot of these homes are $500,000 or above at a minimum in most of these markets. Removing that from the market alone doesn’t solve the problem. A lot of it is the adequate housing stock in the market and accessibility to that housing stock.

It is inventory and it is terrible. Another side of it is taking these homes that are affordable and throwing a bunch of money into them. That $150,000 home is now a $400,000 home. The neighborhood is changing from once being affordable the gentrification and now it is a whole different neighborhood. Several years ago, it was affordable. It is a huge issue. We are seeing it all over on both sides. I was thinking about it while you were talking. This is the 4th or 5th home we have owned.

I grew up in the lower middle class. I joined the Army. I used a little bit of savings to buy a $30,000 home. It is when we got out of the Army. That is how we got started. We flipped it, made $15,000 and bought a little bit bigger home. Every time we have made smart decisions, we are in a pretty nice home but it took a while. Our first home was only $30,000.

I grew up in rural Missouri and stayed there. I would have started building equity sooner, even though my income potential would have topped out quickly. The opportunities and jobs weren’t there. Every home was well beyond my price range as soon as I moved to Boston. Your story is an interesting one. Getting more people to get that first home in their early ‘20s starts to build wealth, especially if people come from a household where the household has rented. They haven’t had the opportunity to build wealth and they also haven’t had the experience of home ownership. That makes it harder for the next generation to buy their first home, especially as homes become less affordable.

There is such an opportunity, whether it is down payment assistance or looking at creative modeling on the mortgages. That is not what we saw before. Realtor.com released a tool for prospective buyers to figure out their affordability range, like, where they should be looking. There are a lot of these calculators but a lot of them are predisposed to tell that you can afford something that you can’t.

It is an interesting design if you walk through it because I walked through the exercise to see it. The outcome where says, “You should probably look at a house that is a little less expensive so you are able to comfortably afford it.” We are always getting upsold in life. We are used to being like, “You should buy the more expensive thing. That is what you want.” If that happens, it puts people in a bad position. In many cases, they can’t recover from that.

It is that predatory lending that used to be way more prevalent than it is now and is still out there. When we bought our first home at $30,000, we were told we could afford a $100,000 home. There is no way in hell I could afford a $100,000 home getting out of the military. My wife has always been frugal, which has helped because I would have been like, “Sure, $100,000 home.” I wouldn’t be here now. Let’s talk about your journey a little bit and the elephant in the room. Something that you cofounded announces it is going public for an unreal amount of money.

We talked about this a little bit. We had Wil Slickers on and we were talking about this coming out. We mentioned the posts that you made. You were thanking everybody and you had to stop because LinkedIn only allowed you to thank many people. Talk about the sale of this and your evaluation of it. Let’s talk about your humble beginnings and why you think it is gotten to where it is now.

It was an interesting journey. I’m several years removed from Vacasa as far as day-to-day. When you invest so much of yourself in something, you are always going to have an attachment to it. I can’t imagine, in my wildest view, what Vacasa would have been. I’m an optimistic person who tends to shoot for the stars as much as I can. I generally have nothing to lose.

My view of what that meant at Vacasa was never about going public. The thing that always made me happy was making creating great opportunities for employees and making guests happy. I was connected to the stories of those guests. That is something that we don’t spend enough time on in this vacation rental community. I hear people complain about guests a lot but they are not a commodity. Sometimes I hear they are treated as a commodity. Every guest has their story. People saw that more in the last few years than they paid attention to it before then.

The other piece was the homeowners. Homeowners have these great stories. In the early days of Vacasa, it was just Eric and me. There was a third cofounder and Nick Tostenrude, who has never mentioned anything but he was only with us for a few months. He is a good friend of mine. He works for Amazon and has had a lot of success in his career. It was a good combination of skills with the three of us and a tenacious work ethic.

One thing I will always say about Eric is that we didn’t have to motivate each other. We were both intrinsically motivated. We both came from humble backgrounds and had a bit of a chip on our shoulders but not sure whom we were trying to prove. We are motivated to work hard and build something great.

The thing that worked well was that we would recognize our failures, learn and move on quickly, especially when it was the two of us. I have seen that more as I have been involved in larger organizations. You lose some of that velocity as you bring more people in, especially if you have people that are afraid to fail. It is like with any startup. You are going to fail a lot. It is making sure that you don’t keep beating your head against the wall and figuring out what didn’t work.

The example that is tangible that I will give is that we launched the company as two products. We launched it as a booking and marketing service where we would take listings and market those across the channels but we had no control over the experience. That was a big problem. We launched the full-service side but you can imagine when we started the company, we had one 400-square-foot home on the wrong side of the highway. That was Eric’s wife’s family’s home in Long Beach, Washington. That home alone did not drive a lot of confidence in our ability to go manage $1 million homes.

It was about us, selling ourselves and getting people to trust us. At that point, there were no Elocks. It was handing over their keys to their home and trusting that 28-year-old me was going to take care of it. It was an interesting time when I got so much flack for being an attorney over my life but at that period, it was helpful because there was a level of trust that at least he had passed two bar exams.

Eric and I did a ton of work on people’s homes in the early days, similar to the work you are doing, John, where we were renovating homes and bringing them up to code. They could pass and get a permit. We were hands-on. People appreciated that. It got us some good inventory in the early days. Those owners became advocates and referred properties.

We also had a great aggressive strategy on direct mail that was fairly novel at the time. A lot of the owners we were reaching out to were not getting that. We did a lot of things right. The thing I’m most proud of is that our review scores were incredible. Our owners were happy. We had no attrition on homeowners. We had no turnover on that side. I still remember the first owner that we lost and it was a relief. I didn’t like having that blemish but it was also a nice lesson. We were like, “We are going to have to start to have higher standards.”

It is to fire homeowners.

That is when you have made it. When you are in that position to be able to do that, you are doing something right from a business standpoint.

We were running and scaling. Depending on when people came into the industry or anything, they may not realize we were bootstrapped for the first several years of a company. We were growing fast. We are using all of our profits to push back into growth. That gave us a lean mindset. We valued the team that was willing to take that ride with us.

The biggest challenge I have with Vacasa is we lost some of that culture as we started taking outside funding. As soon as you take that outside funding, you have stakeholders where the primary concern is, “How do we optimize margins?” The interesting thing looking back on was we had to work with what we had in those early years. We optimized performance quite well on that.

There are also breaking points at scale and I talk a lot about getting twenty properties and you have a real business. It is not properties I have gotten longer in the industry. It is about revenue. You could have 5 homes that are doing $100,000 or 20 homes that are doing $100,000. It is easier to have 5 than 20 homes that are doing $100,000. You are going nuts trying to service low-dollar reservations and there is a need for that but it is a difficult way to earn a living.

I’m getting to those different tiers where there is an operational structure that works with that but there was no blueprint for $30,000 or more homes. As you are recreating a blueprint for doubling in size every year, getting it all right is not going to happen. Keeping that speed was such an important part of our growth, recognizing when things were going off the rails and being willing to pause. If we had a market where the review scores were low, not putting more fuel on that fire was important.

As we grew, having one bad guest experience with 8 guests in a house meant those 8 guests were never going to want to stay with us again. How many of those eight guests may have owned a vacation home? They don’t want to rent their home through us. Our scope was not limited to the people traveling to one market or anything.

Cliff, I got to hear some of these amazing stories about you driving all over the Pacific Northwest. You hear these stories and meet some of the people. They were like, “I remember Cliff and this guy. They gave us a hot tub.” It is this whole story about how this industry has changed. Someone is going to have to write a book, a movie or a documentary about the Vacasa story. When you look at how and when it started and what you were able to build, you didn’t build something cookie-cutter. You didn’t say, “We are coming into the vacation rental industry and we are going to build the largest vacation rental management company in the US and the world.”

You guys said, “We are going to do it differently.” You are bringing a new perspective and smart approach to business that also takes care of people internally and outside of the organization because you can talk to anyone who has been surrounded by or been a part of the Vacasa story. They will tell you it was different. The culture was a different experience in the earlier days.

Talk about what that was like because you didn’t have a background in vacation rentals when you were coming into this. I would love to hear what that was like in terms of building the vision for what you were building and how you were doing it differently with people in mind and a business that is centered around profit and revenue.

One of the common things that people don’t know about Vacasa is it was born more out of a guest experience issue than an owner experience issue. I give the majority of the credit to Eric on this. I could never afford to stay on a vacation rental. At that point in my life, my experience staying on vacation rental was quite nominal.

A lot of the conversations we had early days were like, at that time, you couldn’t get a confirmed booking. You would almost beg someone to stay in their house and they would send you back an enormous contract of 27 pages that signed your life away to go stay in that house and you got to wire the money or something sketchy. The guest experience was atrocious on the booking side. Even on the stay side was wildly inconsistent than now. In a lot of markets, it was standard for you to bring your sheets and stuff like that, which is absurd.

We were far as an industry in some ways and not everywhere. There were a lot of managers that have been doing this for a long time. I don’t want to give the perception that it was broken. There is a lot of opportunity, especially on the owner-managed side. About 1/3 of our inventory would come on from people who were managing on their own and 1/3 would be other professional managers, usually on the lower half in terms of the quality of their service. We brought in a lot of new inventory because we were able to gain the trust of people who otherwise, for whatever reason, didn’t trust the options that were out there.

In those early days, it was so much about what happened on the ground and those relationships. The thing that helped me the most was having a high degree of empathy. I was thinking about what it is like to be a contractor or a maintenance person in these markets and how they probably are dealing with a lot of wealthy people that don’t pay them fast or call them and want them to go fix toilets at midnight all the time.

Having that degree of empathy and trying to pay people fast and take good care of people. I would clean alongside my housekeepers. If there was a guest that was being a jerk to one of my housekeepers, I would take that off of their plate and so would my team as we built that out. Creating a culture of support was critical.

We are paying fair value. We had a $ 12-an-hour company minimum wage back in 2009 when a lot of people in business were taking advantage of the recession and the fact that there was a lot more labor available than there were jobs at that time. We tried to take the opposite approach and did a 401(k) match from the beginning. We added benefits as fast as we could on top of that and tried to keep the pay competitive.

In some cases, we had to help people do math because they were used to getting paid cash. They didn’t want to switch to a become W-2 employee. We had to do a lot of work. Some people had established companies. We had to be flexible. I ended up using a phrase at Vacasa where we had standardized flexibility. We would have our standards of how we wanted to do things but when somebody didn’t want to do that and they were a valuable team member or person to have on there, we would consider the why and make an adjustment. We make that part of our menu of options we would work with.”

On the contractor side, you could be a contractor but you have to be a legitimate contractor. We are not going to let you be an unlicensed person getting paid cash. That was probably my legal side too but we tried to do things by the book from the beginning and on the regulatory front, whether we needed to be a licensed broker in the state or not, whether what the process was for getting a vacation rentals license.

One of my favorite things on that front was that I became friends with the Tillamook County permit inspector. She was happy we followed the rules and would get the permits. People would come in and fail for the third time. She was like, “You should work in Vacasa. They will get it done for you and you will stop failing your inspection.”

Cliff, I got two questions for you and I’m hoping to get some unique answers that not every show is asking. Our number one question is, looking back and coming from that lower-middle-class family, when did you know that you were like, “I made it?” There was that a-ha moment when you were like, “Yes, it happened.”

I always felt it was a greater responsibility. It was 2013 when I was able to buy a house. That was a distinct moment because I did not make much money up until that point. Even then, I still wasn’t making that much. I abandoned a law career, which was clear with how much I was going to make and what stages I would make more. It wasn’t fulfilling for me. I knew I didn’t want to keep doing that. If I was going to stay in law, I was going to start my law firm. That was going to be a challenge when you started from the ground up there.

It was around that point when I felt that we had something special on our hands. After we took outside investment, it started to feel like our ability to keep that culture alive was slipping. It was something I kept trying to work with. Even in the last several years, I was there, I launched and grew the international side of the business and I had that feeling again. It was awesome. We had a great team. I had people from sixteen different countries that bonded closely. We had to operate differently in each area because of the local nuances.

We never traveled growing up. We didn’t have the money to do it. I never imagined I would be flying in launching companies in other countries. The areas I always get sentimental about are the housekeeper stories where maybe somebody was struggling to make it and we were able to give them that lifeline. Those were cool, powerful stories.

Internationally was a different level. We would have housekeepers who were homeless when we started working with them and their whole family was. The little bit of money they were making, doing whatever they were doing, was going to take care of the people in their family where there was no social safety net. A place like Nicaragua, for example, is where this was. We were able to change that within a month.

The dollar goes a lot further. You look at these places where the juxtaposition between what someone is paying to stay in a fancy house versus what someone makes in a lifetime is insane. I still strongly believe that vacation rentals and travel, more generally, can be a vehicle for positive change in these cultures. As long as it is led by that culture, I cannot force it upon them.

I’m working in Uganda. I have a management company over there. I have a local manager that lives in Kampala. She is amazing. Her name is Michelle. Everything is still shut down in Uganda. Locally, things are happening. Nobody is traveling there. The tourism market has dropped out since the beginning of COVID. There is a big gap where those tourism dollars used to be but those tourism dollars also were not flowing through to everyone in a way that was equitable.

We are looking for ways to make sure that our industry is a positive force for change in these communities, not just internationally but also looking at what are the biggest challenges in the communities that we work in for the local citizens there. How do we help them? It is not just about what we can extract from that area. That was always at the core of what we did early days of Vacasa. I feel like it is hard to maintain that when a company grows. That is something I always push for. There are a lot of friends I have that still work there and I’m always planting seeds.

Those seeds are infectious. Let’s be clear. Cliff is saying, “I’m planting seeds.” Those seeds go deep and grow strong roots. You both can appreciate it because I look at you both the same in this space. You see your values come through your actions. Your values turn into verbs. When you look at 2020, what happened with the industry and who was the most affected heavily by the pandemic was the housekeepers.

Cliff and a group of others got together and put together an amazing event and campaign to help them out immediately. That is not saying, “This is nice to do and this is great. We care about these people.” That is being able to put that into action and knowing you can do something to change these people’s lives, even little things.

John, you do the same thing with the art projects and the food projects. We all gel well because we believe in the actions of what we are supposed to do, not just what we talk about. That is why I love you both. When I came into the industry, Vacasa was already rolling and running. Vacasa is gobbling up all these companies everywhere.

I remember one of our first calls together. It was somewhere in Southern California. We were talking to this guy about his properties in Newport. Fifteen minutes into the call, he was like, “Vacasa is still buying property management company. We are trying to get out of this business.” Cliff, this is what you do. You were like, “This is what it turns into.”

Spending time with Cliff, hearing about the humble beginnings and seeing how the company grows and scale is fascinating to see what these organizations become versus what they started. One of the things, Cliff, I would say this is you have been gone for a couple of years but your DNA and fingerprints are all over that organization. Talk to anyone from a Vacasa.

This is at this stage in my career where I’m interested in paying it forward. I feel I was fortunate. A lot of people work hard but there is also a lot of luck involved and being in the right place, right time, with the right group of people. I’m particularly interested in spending my time with people. There are two things. One, there is a social purpose or greater purpose behind what they are doing. They are not just doing something so they can make a bunch of money. That is not inspiring me. I have limited time. I would rather spend my time with my kids than try to help somebody else make more money to make money.

The other is instilling confidence in people that don’t think they could be entrepreneurs. Some of the best entrepreneurs are humble and have a hard time believing they can run a company. I saw that a lot at Vacasa, where we would have superstar performers that had a big dream but were afraid to pursue it. Anywhere I stop and work for a company, I’m always more interested in helping support that individual to become the best version of themselves, whatever that means to them, as opposed to preaching loyalty to the company.

I don’t want people to feign agreement or interest in what they are doing. I want them to truly be passionate about it. If not, I want to figure out what it is. The test I used to have with our local ops teams at Vacasa was like, “Do you feel comfortable wearing your t-shirt around town or ashamed? If you feel ashamed, we need to fix that. You shouldn’t feel like we are doing something in your community that is embarrassing to you.” That is a minimal standard. I loved that we could get to that point of pride where they wanted to promote it. We were excited about what we were doing and felt like we were helping their community.

It is interesting because you’re coming into a community slinging whatever. I have been slinging in this space. I will go into any community. You see Vacasa and TurnKey, which are the same company. The local managers or local homegrown management companies were like, “We are up against Vacasa and TurnKey.” You can see where it’s like, “Are you embarrassed to be wearing this T-shirt or polo with our logo on it?” That is a simplistic example.

You have to have an environment where they feel comfortable saying they aren’t. That is relationships. Even my interview style with people, if I don’t get to a point where we have some type of personal connection, I haven’t done my job well because they don’t trust me enough. It is sometimes hard to do that in 30 minutes or you are limiting interviews to that time. I was famous for going along on interviews at Vacasa. I hogged conference rooms. That is an important time and opportunity in that person’s life. I want to give them the time of day to have that opportunity.

I saw a lot in my career. People are nervous at first. You don’t always get the real person, good or bad. The best salespeople can fool you into thinking they are going to be great to work with if you don’t get to the real thing. There is a clue that I will put out there if anybody interviews with me. If you start trashing your former employer, that is generally not a good thing.

It speaks a lot about, “This thing happened to me as opposed to here is how I ever came.” You can complain about something but it is either bad that you should get out of that situation or it is something that you should try to positively affect in the other direction. I can’t help it but I’m always trying to do the ladder. I’m like, “I can’t be comfortable knowing this thing exists in a way that doesn’t sit right with me.

It goes back to something I heard you say, which is also interesting about culture in the workplace and being able to have a failure as a positive. Look at failure as a valued part of the culture. All of these things go together. It is like dating in the interview. Everyone puts their best face on and tells everybody what they think they want to hear, regardless of how nervous they are and that rolls into the culture. Everyone is always trying to put their best foot forward at the expense of, “Where is the real candor here? This didn’t go well. Do you have a community or a culture in your organization where people can be honest?

To call out your show, how do you get to the no BS? There is not one way to do that. It is different for every person.

I work for TravelNet and sell Track software. They allow me to be me. They have no problems with me doing this show. I have a long leash. There is trust there that has been established. They know that I’m always putting my best foot forward. I know that it is reciprocated. There aren’t a lot of companies that I could work for that would be like, “Sure, do whatever you want.”

That is valuable to you and it costs them nothing to let you be yourself. As an attorney, it is weird. You would think I would be more risk-averse but to me, there is risk in almost everything you do. You could not do anything ever. That is one good way to off risk from your life. You could start to be smart about it. Hire people and build relationships with people whom you trust. If you have people out there that want to do damage to your company, you are probably not either hiring the right people or treating them well. Be self-reflective as opposed to accusatory. It is always my approach.

I had two questions and I got to one of them. That is a great thing about this show. It goes where it wants to go. I didn’t forget that I did say I had two. You can answer it either way you want. It is more of a negative. What is your biggest regret? This is in a business sense, not necessarily life. What was your biggest fuck up? What was the thing that you looked back on and you were like, “Why?”

I do screw things up a lot. The biggest regret is probably an easier one for me to start with, in the sense that I wish that I would have pushed harder to push Vacasa to be a B-Corp or at least a purpose-driven company in a way that was encoded in the DNA as opposed to being a part of the culture. I feel like we achieved having it be part of the culture and that is still there. It is harder to see from the outside because it was never something we indoctrinated and said, “This is part of who we are. We will always do X and X.”

It was happening organically. It didn’t feel like we needed to do it and it was too late. When I’m working with entrepreneurs that have that purpose-driven sense, I say, “Get it in there early and help it not make your decisions for you so that you are not later trying to fit it in with something that is gone off in a different direction.”

As far as screwing up, I have a funny one where I had a perfect housekeeping score for several years that I had some pride in. I had a back-to-back on a large house on the Oregon Coast, where I had five hours to clean. It was called the stairway to heaven. I used to talk to the owner. I should give him a call. He would get a kick out of this. I did a good job but I left a sock in one of the bunk beds. Somehow, I got it stuck in the laundry and I didn’t see it. I got a four-star on that because the guests said, “There was a sock in one of the bunk beds.” They thought we didn’t wash it.

That was one of my mistakes. That was a mild one in terms of consequences. My biggest thing is organization. Mateo can attest to this. It is not my strength. I love to experiment. Sometimes I don’t document as well as I should for the next person who has to deal with that. He would have more than a few people at Vacasa that said, “I had to clean this thing up because Cliff didn’t write it the right way.”

There are two sides to that standardized flexibility mindset. You can try to get everyone a fit in your view of the world or adapt. The part I have to work hard on is making sure when I adopt and finish outlining that process, what needs to change and whom it impacts. Especially as an organization gets larger, that gets harder to think about all the downstream impacts one decision might make.

Thank you. I appreciate you speaking and letting us know what your positives and negatives are. Looking at where this evaluation is and where Vacasa is, I know you wish it might have taken a few different turns and you have been out for several years but is there pride?

Yes, it is amazing to see what it becomes. It is more positive than negative. I still have these feelings. The sense in the industry sometimes is like, “It is big so it is bad.” If Vacasa did not fill this gap, someone else would have. It could have been with a lot less heart. That is not to excuse the things they are do they do that are not good. There are a lot of great people there that care deeply about doing the right thing. That shows in a lot of the execution.

The interesting thing about any large company is there are many opportunities to fail. I used to tell a team this all the time, “As we would grow, we would have X number of people in the homes. We have the equivalent of the City of San Francisco staying in our homes, spread out across the world.” The odds of all these people being insane and wonderful are not high. There is going to be some crazy shit that is going to happen for sure.

We got to be prepared for how to handle it, especially whoever takes the brunt of it and that we are there for them so it doesn’t ruin their day. Most of the time, sadly, that is the housekeeper. The housekeepers are the ones that show up to the shit like what went wrong in that reservation or the guest shows up early and he is a jerk. They get the most unpredictable situation. We had one that had a giant pig that was in a house. You never know what you are going to encounter as a housekeeper.

A giant pig and a large dog are the same things. It is okay.

There is some sad stuff. Those hit me hard but I always try to be there for the team. They knew they didn’t have to handle that on their own when they encountered that stuff. I have more empathy for large companies than I did before we started Vacasa. I always felt like, “How could they do that and this?” There is a point at which you are at a certain size and there are going to be some bad individual actions. You got to handle them the best way you can. Culture is a different thing. It doesn’t matter how big you are. There are bad small companies and bad large companies. It is always constant work to make sure that when situations change, you have to be there and be able to adapt.

We need to wrap this up but do you have any last words of wisdom? This isn’t your funeral. You are still on the Rented and VRMA board. Are we going to see you in San Antonio?

That is the goal plan and hope. We have world events that may change plans for all of us but hopefully, things will turn in a positive direction. I miss that culmination event. Some of my best experiences have been at these VRMA Internationals and some of those conferences. I’m excited to see everybody.

Any last words for us?

No, thanks for the time. This is a lot of fun. I’m always willing to help people that are getting started. That is my favorite. It is easier to start and get things going on the right foot than it is to fix them later. Deal with it now, especially in integrating a purpose, whether that is tying into the community or something else. I’m seeing more companies do that, which is exciting for me, to see more purpose-driven vacation rental companies.

It has been awesome having you on. I appreciate it. It has been nice catching up. It has been a little while. I know Mateo is your boy. You guys are hanging out.

I miss Cliff. I tell everybody all the time. Mickey is here in Atlanta too. I’m like, “Cliff is not here.” He was like, “It is sad.”

Mateo was the only person I saw other than my family during COVID. Mateo and I had a great bond down there. I miss seeing him in person down in Atlanta.

If it locks down again, I’m coming up to Vermont to quarantine.

You always have a place to go.

Thanks, I appreciate you.

Thank you both.

Important Links

• YouTube – The No BS Short-Term Rental Podcast
• Vacasa
• Rented
• Realtor.com
• Zillow
• BDX
• Wil Slickers – Past Episode
• TravelNet
• Track
• Megaphone.fm/AdChoices