Co-Hosts Mateo Bradford and John Stokinger welcome Philip Kennard, CEO at Futurestay.

The title is the moral of this story… or at least it should be.

The desire to offer “alternative accommodations” to travelers when away from home is something that hosts, vacation rental managers, property managers, superhosts, and everyone in between all have in common.

As an industry, whether by design or by accident, we have made unnecessary divides that ultimately are hurting our space as a whole.

Philip and Futurestay place industry-leading tech in the hands of hosts to give them the tools to operate efficiently and successfully.

We discuss lopsided statistics, inclusion inadequacies, and project better environments for short-term rental business operations if coming from a focused look and level playing field.

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.

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We’re All In This Together With Featured Guest Philip Kennard

I’m super stoked because this episode’s guest is someone that I consider a good friend, someone I look up to and mentor in the spaces. Phil Kennard, welcome to the show.

I get to start out the day by having a long conversation with you and talking about all the stuff that we would be talking about if we were meeting at the conferences and more likely the stuff that we would be talking about in the bar after the conferences. I’m excited about that. I haven’t gotten enough of that in my diet in terms of getting to dig into what’s going on and chat with other like-minded people and other leaders in this space.

Phil is the CEO of Futurestay. He is a technologist. He’s an investor and an overall awesome guy whom we have had the privilege to meet with, hang out with, and learn from and build a relationship with within this industry. Someone I have a lot of respect for and who has been helpful for me and my journey through this industry. I’m super psyched to have you on and get your opinion. This is going to be a good one. There is a lot of stuff to talk about.

I’m excited to learn more as well. Unfortunately, the only time that I have gotten to know Phil at all was through a podcast that I watched was Paul Stevens did an interview. That was a two-part series and that was excellent. I’m glad to be able to listen to that. I do want to pivot real quick. I think that podcast was on diversity. I want to tie that into Mateo and I put together a webinar that went out and had great attendance.

We called it Diversity and Inclusion: “A Real Discussion.” If you are interested in watching that, we have it broken out into six episodes. We got the news that VRMA has approved this as a panel discussion for international. Mateo and I are going to commemorate this. We are super excited about it. We have some great paneled guests and it’s going to be awesome. We are super stoked. It was supposed to be in 2022 International. That didn’t end up happening down in Orlando. We are excited that we are going to be able to do it in San Antonio in person. That’s awesome.

This is a challenge that a lot of minorities have internally, and I’m not trying to say, “I have made it right,” but when you get to a certain level in the career and you have that access that wasn’t granted, but that you built over time when you see diversity, inclusion, and efforts, you are of two minds. One is saying, “This is great. We know how important this is. I’m glad this is going to raise awareness.” The other is, is this virtue signaling? You saw the George Floyd protest. America is upset. The world is looking at us like, “How do we show that we are not that far behind the times?” It’s okay to be a little behind the times. What do you think about this particular initiative? How do you balance that in your mind? Where do you think this is?

I’m all about verbs. It’s about action. It’s about not so much what you do at the moment. Yes, what you do at the moment is important, but what is the residual effect of that action at the moment? We are seeing a lot of that. Everything that we talked about happened in 2020. What’s happened since? It’s been years since George Floyd, unrest, shaking, and awakening of our country and granted, that’s not the only thing that’s been happening. A lot of noise going on. To me, that cements the importance of, “What is the action post the event when it’s out of the news cycle? What are companies doing now?”

Are diversity and inclusion still on the radar? Are there actions that are backing that up and improving that? Has it been pushed down to the bottom of the to-do list? With varying responses, and to be 100% honest, I’m seeing a bit of both. Being altruistic like I am and understanding, I get that there are things that are happening. People’s businesses are back opening, but it doesn’t excuse the fact like you still have to call it to the floor. If this is an important initiative, it doesn’t matter what’s going on. It’s an important initiative that needs to be continually addressed and actioned. The awareness can’t just go away because it’s out of the news cycles.

Diversity is not going anywhere. These initiatives still need to be addressed. Programs need to be worked on. Funding needs to happen. Cultural change still needs to be worked on and pushed through and progressed. Just because we got to talk and we had a panel about it, and because we got some people together and started discussions, that’s the first step. The next step is what is the legacy that we are going. What are we doing to put the mechanisms in place to ensure that we are not having these same conversations in the next years down the line?

The hard part about all of this and for me, it was brought to my attention because I reached out to Mateo. I said, “I don’t know how to talk about this.” I don’t know what is the right or wrong thing to say. The George Floyd incident woke me up a little bit. It was always there for me. Mateo has always been my brother. We are close. I looked around and said, “I don’t even know how to talk about this.” I’m just this White guy in a White industry, in an old money industry, and I knew there was something that needed to be done, said, and talked about, but I didn’t know how so I reached out to Mateo.

We had a great splash. We made a lot of traction early. Everyone was on board. You see where now it’s out of the lime line. It’s not the center of the discussion anymore. It’s like, “We don’t have any funding for that. We don’t have this. It’s a great idea, but.” We are trying. This was a win for us, but it’s also a loss. It’s been a battle for us to get some there. There are certain individuals that are amazing. They’re bending over backward to do what they need.

If there are only certain individuals as wonderful as it was, we just need to keep pushing. It’s unfortunate. Speaking of this, we had an amazing guest on Episode 10. We had Robert Geller, the Founder, and CEO of Fabstayz. He is a self-proclaimed Fab Founder. He’s amazing. To bring light to this, I love looking at our numbers. How many downloads are we? We are growing. We are doing great. Unfortunately, the title of the episode was LGBTQ+ in the short-term rental space.

In the first week, it’s about 60% viewership compared to any other one going. What does that say about the openness of the people of our industry? It’s unfortunate. I hope more people will go back and read it because it’s one of the best episodes we have done. It’s enlightening and great. It is what it is. We keep pushing forward.

Having to be constantly conscious of the distinctions, parallels, challenges, discrimination, history of it, or potential solutions, having to be conscious of discrimination for the relationship with other minority groups like LGBTQ+, all of those things are draining for everyone involved in our consciousness. It’s tiring to have to think about it, to create panels around it, and to be it. One could make the argument the most tiring thing is to be a part of that group that is let’s say it’s marginalized, removing or shedding some of that marginalization, but not still viewed in that way.

People don’t want to click on that because everyone’s tired already. They don’t want to hear another thing that’s going to make them more tired. I get that. Put yourself in the shoes for a minute of the person that doesn’t get to not listen to the episode because they live the episode. It is what it is. The silver lining in all of it is what happens after it leaves the spotlight or the limelight. The answer to that is, you guys are talking about it. John, you reached out to Mateo to have a conversation about it because you didn’t know what to say. You had your own thoughts, but you didn’t know what to say or how to broach that topic, how to create change, or how to impact things. You decided that you were going to take and put that effort on when you don’t have to do that.

Mateo doesn’t have too much of a choice. We can talk about it and not talk about it, that’s up to us, but we are still going to live it either way. That’s going to be our lived experience no matter what, regardless of whether or not we spend time talking about it. Neither one of us spend all our time talking about it for certain. It’s passed the anniversary of the George Floyd killing and the sentencing of Derek Chauvin. It’s a timely topic. Ultimately, even when it’s not in the headlines, it is in the lives of many people throughout the world. People like you, John, who decide that you are going to make it a priority when you have limited resources and time are how the change happens.

I have had lots of conversations with people who don’t understand. They feel the weight of everything else especially if you don’t understand somebody’s perspective, or don’t take the time to understand where somebody else comes from, it’s already heavy enough. You think about the weight and the gravity of the issues that we are dealing with as a country in a society right now around race, sexual orientation, politics, or whatever it may be. We just go here instead of taking a step back, working from like a base level of let’s operate from a level of understanding where are these people coming from? What is this? Instead of being like, “Now I got to deal with this or something else. I don’t understand this. I don’t get this. I’m just completely not even open to this.”

It’s a lot and I think it’s how people process these things. Unfortunately, John and I are able to have conversations. Other people that I know and don’t necessarily agree with politically or otherwise. I have good friends that we can have conversations with, but even within those conversations, it’s the weight of my side versus your side. Not saying, “We are in this thing together. We have differing views about certain things,” but the baseline is, I respect for you as a human being and you respect me as a human being, and then building out from there.

In those conversations, I don’t expect you to own my experience or be responsible for my experience. What I expect as a friend and as someone who if you have consideration for my humanity and me as a person. I expect you to listen and hear my experience. Not your job to fix it immediately, but to be open and to understand that my experience, while it may make you uncomfortable, is my reality in my life and for others. The same with issues around people’s sexual orientation, where we want to be understood, but we also have to understand that, on the other side of that, there is a narrative that other people have grown up around.

There are communities that people have gone through and have these beliefs. They may be legacy beliefs that aren’t just going to change overnight with the dialogue and open conversation. If you start from that baseline of being willing to give understanding and in the same effort that you would want to be understood, that seems to be the baseline that I am able to use to have meaningful conversations with people. I’m not trying to convince you. I’m just sharing my story and my experience. If you care about me as a person and my friend, then you are open to hearing that. That’s how you open those doors. The part that I wanted to get to with this is that it’s heavy. It’s weighted and the reality of it is people don’t like to have things forced down their throats, masks, vaccines, or whatever.

No one likes to be forced to do anything.

That’s the part that bothers me more than anything else. We will cut it off the nose and spot our faces like, “Don’t tell me what to do. Even if what you are telling me what to do, it is the right thing.” How do we get away from that part of it to where we can look at it and say, “Your freedom is still going to be there.” You doing something and being understanding of like, “We are all in this thing together.” When you are being asked to do something, it’s more of, “Do this for the betterment of all of us,” versus just, “What’s your personal preference?”

Mateo, you figured that one out and you are president of the world. The core challenge of humanity is getting people to empathize and understand that other people are at their core people and that you are more similar to people in other groups than you are different. If you can get people to overcome that fallacy, you will change the universe.

It’s a truth, and we know it.

This is literally a psychological phenomenon known as the outgroup homogeny bias. It’s measurable. It’s been studied. It exists but knowing it and naming it, doesn’t make it go away. This is nothing to do with like race or sexual orientation. I believe that people from New Jersey act a certain way and people from New York do. This is just any group of people that can define themselves as this and can define another group as a that will do so, and that will believe that people in that group are more different than them than the differences within this group. This is a human trait.

If we bring it back to the short-term space, vacation rentals and business as a whole, it’s like what can businesses or groups learn from this? What you can learn is being inclusive and diverse is going to go ahead and open up opportunities that you didn’t even know existed. It’s going to go ahead and open up doors, bring new business in, and open up ideas. Think about building a diverse workforce in your company. If we are looking down to the company level. If you are going to go and have a bunch of type-A people, and again, we are taking race. That’s who you are folks, your audience, and who you are.

If you go ahead and you bring A through Z personalities together, and then you have them all working together, you are also reaching those A through Z personalities. That’s what this all comes down to. We are all in the alphabet. We are all connected in one way or another, but how do you go ahead and better yourselves without doing anything other than being open-minded?

This mirrors the conversation about why I am in the short-term rental industry in the first place, what my vantage point is on it and what is unique about my vision, and also what needs to change in the industry. This is about removing the uss and thems and understanding taking that step back and analyzing what things look like. This is a piece of data that we talked about when we first met, which is probably at a conference in Amsterdam or something like that.

If either one of you guys has ever seen me speak, and I have spoken at VRMA, Booking.com conference and Focus conferences, and so on. I get on the soapbox and I say the same thing. The first thing I say is, “At the X hundred billion dollars,” because that number always changes arbitrarily every year, “Short-term rental industry, 70% of properties are managed by individuals or independent small managers.”

That alone is shouldn’t be a controversial statement. It becomes controversial when you look at the way groups, investors, OTAs, and the powers that be that deploy resources and capital into this industry, and the way where they are pointing those resources. Ninety-nine percent of dollars of venture capital that has been invested in the short-term rental industry has been invested in companies that either manage hundreds of properties for technology built to serve those managers.

In turn is 30%, not 70%.

By booking volume, it’s almost the same. The booking volume for 1 to 10 properties, you are looking at about 72% of bookings for properties that are managed by the independence of 1 to 10 properties. You have about 28% that are 10 plus properties up to 1,000. There’s a great graph that I love to show people that’s transparent. The interview has a similar one too, which shows this stacked graph and bookings for units with 1 unit is 50%. Fifty percent of bookings in the short-term rental industry are for properties that are managed but have one unit that’s owner, typically.

Sometimes, it’s the management of one unit. It’s like, “Let’s take a step back as an industry and understand how can we grow this industry?” This is what I’ve been saying at the soapbox for years, “If we want to grow the short-term rental industry, we need to make sure that the rising tide can lift all boats in this industry and that we are adequately preparing independent managers who make up most supply and most bookings are prepared with the tech, education, resources and the support that they need to connect to what is now an on-demand hospitality industry.”

That’s the fastest-growing major segment of the hospitality and accommodation segment and in the future, will be the most popular one the way that is going to be considered the default means of travel. Once the on-demand economy, once we remove more friction from it, and you make it easier to connect that long tail supply, this is going to be the most populous, volume-based to the highest volume accommodation class in the world.

How is that industry going to work if we don’t equip the regular guys, Joes and Suzys out there with the picks and shovels to be able to take advantage of the market? What we see instead is the rallying cry. This is where I get frustrated. People that are reading can probably infer what we do at Futurestay. Where I get frustrated and you here, “If you are not a professional manager, you need to leave this industry.” We want 50% of the industry to leave overnight.

If we are putting ourselves in the shoes of the people that are saying that is in, truly, A) They are saying that because they see it as competition. B) If I’m looking at it going, “How do we go ahead?” This is obviously why you are coming in, and exactly what you do is, “How do we give the tools and resources to these the 70%, 50%, or whatever it is to make them professional? With regulations and restrictions on regionals here and there, it needs to be more professional. There needs to be some stringent guidelines and this is how you operate. This is how you are going to be successful, and this is how, as a whole, we are going to go ahead and rise these tides and raise and lift all these ships.

I want to throw one more data point in here. As we are talking about this, we have a well-rounded picture. When I saw this graph, I was surprised. That’s the second thing to say when I get up on a soapbox, which is that there’s a strong positive correlation like 0.7 or 0.8, and it’s a negative correlation, between the size of a manager’s portfolio and their average review score. I’m not suggesting that big managers are bad managers. That doesn’t make any sense at all. They are far more successful in many ways than small managers are.

The review scores for smaller managers, in fact, the smallest managers have the highest review scores, and the largest managers typically have the lowest average review scores. There are one million reasons why that can be the case. Sometimes people are reviewing because they had a coffee with you. Ultimately, the reviews are a measure of the guest experience. The point of saying this is that there is a strong relationship with a high-quality guest experience and a small manager.

There are also many areas that the guest experience that needs to be dramatically improved and professionalized with a small manager because as we are saying here, we can’t modernize the industry. When you have people that are still listing manually on channels that are getting double bookings because they are using an iCloud to try to connect their Booking.com to their Airbnb. They don’t have insurance so when someone burns their couch, they go out of business.

There’s a plethora of lack of professionalization challenges. I will say even the small or medium manager and the independent manager segment, anything less than 2025 properties, there are significant professionalization and operational challenges. John, I know you see them, I see you posting about them.

People are working triple duty. They are being a property manager in the morning, a cleaning person on the weekend and on Wednesdays, or an actuary to reduce risk and try to screen guests before check-in. They’re trying to do risk mitigation and debt collection, way too many jobs. That’s across the whole spectrum until you start getting to the enterprise segment where you at least have people to do that. That’s what the industry needs to fix to professionalize, in my opinion.

It expands on the conversation of professionalization like, “What does that mean?” It’s interesting you are going to hear one segment say, “All of these individuals, hosts and others need to go to professional management.” That’s been the attitude that people need to transition, but that’s not happening. Now there’s a rallying cry with, “We need more properties, hosts, and inventory for the industry.” Property managers are going to go out and start farming, but the reality is now more people, especially coming out of this economy as stimulus checks and government assistance is going away, people’s real economic situations are going to come back to life.

Now you are going to see more people looking to back to the gig economy, “I have a room, house, or an ADU to rent. I just acquired another property,” or whatever that means may be. This segment, we are seeing it with the Futurestays of the world and others in the industry that are like, “Even prior to Airbnb and the others making those huge announcements that they want more inventory, people were already seeing the facts and figures that you put out there and saying, ‘Why isn’t anyone addressing this?’” From an educational standpoint, providing them with the tools to be able to do this is.

The reality is, not everyone’s going to be a good fit for a management scenario. Some people want to learn to be better and enjoy the process of hosting. They may have 2 or 3 short-term rentals and they enjoy doing that instead of driving Uber, Lyft or whatever additional income means they may have. That’s a huge issue. For us not to embrace them, we think about what we are not embracing. We need to embrace that. The industry has to embrace that because if we don’t, at the end of the day, if you ostracize them and push them to the margins, they affect us.

They definitely are going to affect our business, how we operate, what we do and how we are seen in our communities from a regulatory standpoint, and how communities feel about SDRs. It’s a broad-ranging part of this ecosystem that we are all in together. It is important to approach it with the attitude of education and outreach. How do we bring this into the fold? We don’t need to treat the segment of hospitality like hotels treat short-term rentals. They are not going to be around. We will figure out what they do and continue to move on. We need to embrace them.

It’s true. It’s not just to be altruistic, but it’s the reality of we are chained together in this. If we don’t want to continue to fight about parties, hosts not doing the right things or managers. Not all managers are private. There’s an education cycle in here that everyone needs to be a part of and embrace it. We need to take on for our own survival and for us to thrive in this space. It is a great opportunity to help this segment, and our industry and build our strength to push forward for a future that is profitable for everyone because let’s be very clear, there’s dollar science attached to this too.

There are opportunities to help people make more money and through that, help the industry becomes stronger, more profitable, more in line, and a stronger voice together. The reality is we can think of a million ways to divide ourselves, but the fact is, we are stronger together. We are stronger when we are more cohesive and when we embrace the diversity of our business models.

I’m very transparent. I have been in the industry for many years. Mateo is a similar timeframe. We haven’t been in forever. We came in from a “professionally managed” background, more of the property managers, not the individual hosts. Let’s take professionalism out of it. With VRMA and all these different organizations that are more geared towards the property manager as of the individual host, I know overseas, there are some more individual hosts-centric organizations. Do we have anything like that here in the US? If so, I’m unaware and I want to be more plugged into that.

To clarify what you are saying about the organizations in Europe. I see a lot of shows. There are a good number of shows. I will namedrop some because I think they are excellent resources, which are the Host Show and the Short Stay Summit and so on, which tend to be a mix of mid to small managers. Some of those are just distinct because of market dynamics. In Europe, you have a higher concentration of small to medium size property managers. In the US you have the two ends of the spectrum where you have a vast number of independent managers, a very large number of independent managers with 1 to 5 properties, and then you have almost like a Valley with very few managers in it that have between 7 and 20 properties.

The people that figure the formula out here move on rapidly to either growing or they don’t figure it out, and they get their properties managed by a professional manager. You have this big gap in the US that doesn’t exist in the same way in Europe, I don’t think. You have a smaller number of massive managers in Europe. I’m going back to like 2019. You have the inter homes of the world, and psychs, etc. There are some massive managers but there are not as many independents. Those independents would get swapped or would get picked up into the massive managers.

That’s simply because it grew up in a different time in Europe and it grew up here. It’s more mature, because we had the benefit. It’s like the subway system. You go to any other city in the world other than New York, and you are like, “This subway is great. What happened in the New York subway?” The answer is, “I’m from New York. We built our subway first, so it sucks.” We learned everyone else got to look at our crappy subway and say, “I’m not going to do that way.” What happened in Europe as well, where they built the holiday lettings in a short-stay industry in a way that was inconvenient, filling all complex and unwieldy rules it was very difficult to list and manage as yourself or as an individual.

There was no technology at this point in time. In the US the industry rapidly accelerated then we were making the transition from guidebooks to digital guidebooks to online platforms, to online booking. We grew up here at the right time to catalyze the movement of independence. Whereas they grew up, they started growing up, and laid the ground for the industry prior to that. That’s the result is they have a bunch of small and medium-sized, small managers, and independence doesn’t function the same way.

That was a long premise, but the premise of that is to say that I do think there is a growing, especially in urban areas, independent movement in Europe, but at the same time, those things that are shows, I don’t consider those organizations. I think they are great shows. I have attended them. I have spoken at hosts, but those are great trade shows. They are great learning experiences, but they aren’t there to give ongoing support like VRMA. VRMA is a trade organization. When I think about support, I think about renting Responsibly. Do you guys know that Responsibly?

They do a great job.

The way that I define the independent segment, it’s not 1 to 10 properties. That’s a helpful number. That’s useful to draw a line and things so we can count stuff. In reality, it’s a property manager owner that is operating a short-term rental business without significant material educational or structural support from another entity. Their ass is on the line. If your ass is on the line and you are going to lose your house, not your company’s house, you are going to lose your house if someone burns it down, or when that double booking happens on a channel where you have to reimburse, you got to take $2,000 out of your bank account, not your company’s bank account. Maybe you are the joint sign or the main sign-on. That is an independent host.

Independent hosts can scale all the way up to 20 or 30 units. I have seen them. We work with them. Most of them are very small because it’s very difficult to build an independent business with 30 or 40 units. Typically when someone gets a business around 10, 15, or 20 units, have enough corporate or structural scaffolding around that so that they would no longer be an independent host. However, most of this industry sits squarely in the independent segment. Understanding that major difference, which is they need support.

I will put an earmark on that too. They need good support because of one of the things I learned. When I started at rented, they were still the marketplace that was pairing individuals looking for professional management at the time. To learn the industry, I was like, “Where are people going? People in house homes, where are they find it? What’s in the market?” I would go to like meetups and Craiglist stuff that, “Make six figures off your Airbnb. Off your cell phone for a month,” to see what information people were getting out there. I did find good organizations like Host2Host. Shout-out to Debbie in the Host2Host community out in Portland.

They do a good job of bringing in hosts and smaller people together, creating a community around that, and doing education and working advocacy together. There are groups like that around the country, but a lot of people are still on the hustle side of the business. That’s where a lot of the people who are novices because they don’t know where to go. They don’t know that organizations like VRMA and other professional organizations are out there. When they go to those organizations, they probably didn’t have the best experience where I was like, “I got two homes.” They are like, “We can’t help you.” Where do they go? Then it’s like, “I want to make six figures off my cell phone. I’m going to go to this and buy this packet or go to this program.” It’s hit or miss.

The caveat to that is let’s go ahead and look at Clubhouse the same way. There is a ton of great and bullshit information on Clubhouse. There are many thought leaders like gurus. I listened to some of it and I’m surprised. I silently leave or whatever you could put it. I’m like, “Peace.”

This is the continued evolution of exactly what Mateo talking about in the sense that wherever there is demand for whatever type of information, someone’s going to figure out how to capitalize and monetize on that demand and create and supply it, even if they don’t know how to do it. Clubhouse is interesting in a lot of ways. The medium itself has a lot of potential for our industry specifically when you are talking about the independent segment because I’m fairly active on Clubhouse. I participate in a number of groups. I’m a leader of some of the groups.

It’s a tough format to be able to have a substantive conversation. Here’s the reason why. When you are talking about independent managers, there’s this journey. In Futurestay, we call it a roadmap. It’s like, “Where in the journey are you? Are you someone that literally doesn’t even have an Airbnb listing yet,” or whatever the first channel that you are going to list on.

You are thinking about putting a listing out. You realize your uncle’s house is vacant for nine months out of the year because he’s now moved to Singapore. It’s nicely decorated or whatever. You are thinking about getting a listing together. Are you there or are you maybe two stages later where you already have a listing on your channel of choice? You don’t even know how to gauge market performance. You downloaded a report on AirDNA and it looks like you are not doing great, but Airbnb smart pricing says you are or are you at the place where you now are able to pay your bills, but those one-off events are costing you so much money.

When someone lights a cigarette outside and it creates burn damage on your deck, or someone steals your mother’s vase, or whatever it is. You are trying to figure out how to do risk mitigation. That journey is not linear necessarily, but it has steps that go in groups in order. The problem is when you try to get in front of a room of whoever shows up at your Clubhouse talk, you don’t know where to talk to them.

What I’m interested in the space, and I guess we can talk about Futurestay a little bit too is that I want to be the world’s foremost expert at understanding how data connectivity, optimization, and automation can work together to create guardrails around an independent manager’s business and help them meet their own goals. Help them meet the goals and expectations of a traveler, and help them meet the expectations and demands of the short-term rental industry, including regulations and OTAs demands.

When I talk about automation at Futurestay, some people are like, “You guys are an automation platform, PMS, or a channel manager.” Futurestay is not those things. Those are useful. It’s like saying, “Is Netflix a video rental store?” “No. That was a helpful construct on the way to what Netflix is.” Futurestay is an operating system for independent short-term rental managers.

It’s the dashboard they log into in the morning to see who’s going to check-in. It’s what they look at after lunch to make sure all their payments were collected correctly and that the chargeback that happened was successfully fought. It’s what they look at after dinner to see that all the emails were sent out and the online check-in receipts and notes were sent out correctly to see the engagement with their campaigns.

They look at it before bed to get a good night’s sleep and realize that their NoiseAware device is not going off and that their insurance policy is successfully processed. That journey of taking someone from not having anything, from literally trying to decide whether to put their uncle’s house on Airbnb to getting to that stage is the roadmap that we provide at Futurestay, with our technology.

It’s getting independence to have guardrails around their business so they can do the thing that they do well, which is finding, discovering, and creating supply, bringing into the industry, and giving amazing guest experiences that are rated by travelers as the best in the industry. It’s taking all the other crap off their plates because no one likes fighting chargebacks.

If my cofounder and COO were on this show, he would say the exact same thing. He would be like, “I do like fighting.” My team loves fighting chargebacks. There’s a team that likes to do it. We like to do it with technology, with all the tools in place. A manager should not have to like fighting them, learn to fight them or even see them. They can be absolved. That’s what Futurestay does. We bridge the gap between the expectations of a massive rapidly growing industry and the ability of independence to catch up with that we do that through a combination of tech and process. That’s how that works.

When we look at the space, we see opportunity. We see a gap that needs to close. We need to figure out how to build the advocacy around that to help everyone row together and close this gap and not create this us or them where people are saying, “We don’t want people that are not professional hosts in the industry and they define professional hosts as not doing this full-time, not having X, Y and Z number of units,” and those sorts of things. We got to create that come-together moment.

The theme for the episode seems to be In This Together. We are definitely in this together from the diversity side of things to us or them, to the professional or unprofessional. We are all in this together. We all have the same goal. We all want to see some success. Success is how that is defined is different for everybody, and that’s okay. That’s totally cool. As the short-term rental, vacation rental space, it’s like, “What does that success mean to you? How are we going to get there?” The only way we are going to get there is together.

That’s the interesting part. You get to define what success is for you. Not everybody has the same goals. Not everybody is running in necessarily the same race. Think about the Olympic trial. We are all on the same team but all the different events can coexist together. The goal is to be the best in class in whatever event that we are working on. The inclusiveness of it has to start with, “It’s okay.” You want to be a better host in this industry. Awesome. Welcome. You want to be a professional manager in this space. Awesome. Welcome.

That’s the environment that we have to be able to embrace. If we truly want to thrive as an industry again, we don’t get to dictate who is seen in our space. Hosts are going to be here. It’s not going away. Shunning them and wishing that there’s something that they are not, isn’t going to get us anywhere. How do we change the narrative and the conversation to say, “How do we make this industry best in class regardless of what your event or your weight in this industry is?” That approach is going to propel us to the future and to success faster, in my humble opinion.

Matt Landau had an Inner Circle post that he puts on it. It was interesting to see. The question was, “What is a professional manager and/or what is a professionally managed company?” I’m not quoting here. Everyone chimed in and it was so different. It was wonderful to see how different was, but it was also humbling, to see how steadfast people were with their opinions on professional management and basically, “You are a professional manager if you do X, Y, Z.” You are not if you don’t.

I came in from a different direction. It was interesting because the bottom line is we are all in this together. What is professionally managed to you is the same thing as what is success to you. Ultimately, we still have to be together because we still have regulations and all these things where we have to fight to make sure that we can all be successful.

Ultimately, when we figure out how to ally on this and how to bridge the gap, you have to remember the one advantage that the independent segment has, it’s certainly not coordination, but numbers. Think about how much more noise 1,000 managers can make in a local area than 1 manager with 1,000 properties. Maybe 1 manager with 1,000 properties can get a meeting at city hall. 1,000 managers with 1,000 properties can get the law changed.

All 1,000 of those people should be reading this blog.

How are we going to learn about the issues? This is why I call it the soapbox because I think that people don’t think of this as an issue because there’s such an echo chamber in the industry created around the enterprise segment. As they say, “I know the enterprise segment. Some of them are good people.” Honestly, it’s like, “All of my friends in the industry are in the enterprise segment because everyone’s in the enterprise segment.”

I get that this is a unique challenge, but this is something that we need to create a discussion about. We are talking about the hard work of diversity. This is diversity. I had a great conversation with one of the board members at VRMA about diversity and they were like, “We are talking about D&I.” I’m like, “I want to talk about diversity in property managers. I want to talk about how VRMA gets from several hundred manager members to tens of thousands of manager members.

I have thousands of individual managers using my platform at Futurestay. Thousands of clients, hundreds sign up every month. When you compare that to enterprise management systems, they have usually dozens or hundreds of clients. The access to help individual people pay for their college student loans to pay for their kids’ tuition to change their lives. This is the power that we have as an industry, but like, “I can’t do it by myself.” We need to create a broader discussion about it. The first step around all of this like we started this conversation out is awareness.

It’s, “How do we make sure that the guy or girl with two properties are going from 1 to 2 has a seat at this table? How do we make sure that we give them the support that they need so that the policies when they change, don’t prevent them from accessing the market and make it harder, make another hoop for them to jump through?” Give them the understanding of how to get their supply to where the market wants it.

How much do you want to bet the diversity and manager type and diversity of other types are correlated within the space? We go down that road. We are going to see a lot of synergies in that space. One goes with the other. You can look at regions and markets.

I don’t see everyone that we work with, but I get to talk to some of them and meet some of them in person. It’s a vastly different, more diverse group from sexual orientation, age, race, or to everything that you see when you enter socioeconomic status. The whole gamut is run and all these things are correlated. There are barriers in walls that we have to break through. We are doing it and as we said about it, so this is the way we do it. We have conversations about it. We bring it to the forefront. We will put the work in.

That’s why this format is successful. We are stoked that you joined us. Thank you so much. We appreciate the conversation. You bring something to the table that we haven’t had yet. We look forward to having you in the future as a future guest as well.

Thanks. This has been a great conversation and super energizing. I love to know your perspectives and insights on everything. I appreciate it.

We got a whole bunch of new things coming out. This is our side gig. The sponsorships are helping us fund this so someone else can do it because we are working all hours of the day to make sure this happens. Episode 12 will come back. Thank you so much.

Important Links

• Futurestay
• VRMA
• Booking.com
• Episode 10 – Past Episode
• Host2Host