Feeling The Fear And Doing It Anyway

Hi, everybody. Today, we're talking about feeling the fear and doing it anyway. So you're listening to the Bootsley podcast, and if this is your first time listening, this is the podcast that gives hosts the tools, the tactics, the trainings, and most importantly, the confidence to go out there and get more direct bookends. And confidence is something that we're talking about today. We do a mini series on the Bootsley podcast, which talks to a short term rental host, somebody who has started their journey, who has felt that fear and has got started, and is now helping to motivate others to do the same. So this is the mini series where we dive behind the host. And here today, on behind the host, we've got Jason Reese. He's got 5.5 properties, and we're going to share YS 5.5 during the podcast. And he's going to be sharing his tips on things that he's learned across this journey, and how you can get started yourself. So let's dive into it. Reese, welcome along. Yeah, thanks, Liam. I'm looking forward to the conversation. So first of all, can you give yourself an introduction? Let us know about your business and anything you'd like to share. Yeah, so I started hosting just a little over two years ago. I haven't hosted a single person prior to that. And going back to 2011, I started my career in medical advice. And after about 11 year long and successful career there, I got restless. I sold the business there from multiple different angles. And ultimately decided that along with some burnout, I decided now is a time to dive into the entrepreneurial journey. That I've always kind of felt a pull to do. And Airbnb was kind of an intersection of a lot of different interests of mine. So I do head first and bought my first property in October of 2020. And so that was during the pandemic. So I didn't let the, didn't let the pandemic shut me down and, and you know, put out that fire. I've done that. I've let the fire go out too many times in the past. And I haven't pursued some of the things that I wanted to do. But this time I was pretty determined not to, not to let that happen again. So I got started in 2020, late 2020. And now that year, I have five and a half properties that I'll have on Airbnb. That half is my personal home that I decided to kind of use Airbnb strategically here. Since they am in Nashville with some pretty high demand premium weekends. And there's some things that I've paid for for the house, some upgrades for the house that, you know, I wanted the house to pay for its own shoes, you know, pay for its own nice things. And I spent about $20,000 on the yard recently. And I decided I'm going to let the house pay me back for that. So that's how I'm using the, the point five. So I know there's going to be a lot of people who, you know, feel that fear before they get started. And first of all, you know, doing, having your own house on short-term rental and available is, is, is a different fear from getting started with your first property. And we'll talk about both of that. So take me back to when what was your fears before having your first short-term rental? What was some of the things you worried about? And how did you overcome those, those fears, those challenges? Well, I can tell you that just asking that question or hearing that question gave me chills. I think it's because a lot of it was because I was in golden handcuffs. So my career was very rewarding in a lot of aspects. And I was, I felt extremely fortunate to have found that lot of work. It was rewarding both personally, but also financially. You know, at the end of the day for the work that we were doing, we were working with patients that had abnormal heart rhythms. And we would build 3D maps of their heart during the procedure. I would co-pilot for the physician. And together we would go in to fix that patient. And oftentimes we fix their, their heartbeat, you know, within a split second of finding the right location. And a lot of that had to do with the insight and navigation that, you know, I was providing work. Eventually, my team was providing the very rewarding role. And as I climbed the ladder through that company, I found myself learning, a lot about the business from all aspects, but further I got away from that reward, the patient or award. I would say the less fulfilling it became. And eventually I worked my way into the corporate office out on the West Coast. And I managed our 3D mapping software portfolio for the United States and let some of our key programs and initiatives. And again, very rewarding because it was complex, it was fast-moving, et cetera, but it ended the day to burn me out. So the discomfort that I faced was leaving a career that I had built that I absolutely loved. I worked for Johnson & Johnson for almost 11 years. I built a reputation, I built a network, all things that I was proud of. But I didn't feel, I didn't feel fulfilled at the time. I no longer felt how I did earlier in my career. And from that position and corporate, I didn't see anything that appealed to me within the organization any longer, or even within an employed setting of any sort. So it was extremely uncomfortable to leave behind the idea of even leaving behind a career that so many people would be thankful to have. And should be thankful to have. It's a great place to be. But for me, there was a feeling of being called to answer that entrepreneurial knock, if you will. At a time where it made sense to me, the burnout was real. I experienced physical symptoms in the office where I had to go to the doctor, the outside doctor, chest pain, stress, high blood pressure, all things that were very foreign to me as someone who was known to be extremely hardworking and committed. So once it got to that point for me, it was eye opening. So the discomfort came from leaving all of that behind to try and do it all over again in a completely unrelated field. And I'm a very calculated person. So to get to a point where I felt comfortable enough was was tough to do. I can imagine. And obviously now you're sitting here today with five properties. Are you still in full-time work at the moment? Are you still working the same job or are you now in property fully or in short-term rental fully? No, I went full-time self-employed in the last July. Congratulations. That is amazing to hear. So what has been some of the while moments since you've started this journey? Because obviously your first one, feeling the fear and then doing it anyway. And then obviously you've added to that. What's been some of the while moments along the way? I think the first while moment is when you get your first property and the bookings start to roll in and then the reviews start to follow. And you're like, wow, I can actually do this. I'm actually, I'm one of the people that I've been studying and researching for for so long. Wow, it's really not that hard. I think we tend to build things up to be quite a bit more intimidating and daunting than oftentimes they are. But more recently, I would say that when I crunch the numbers on how many people I'll host this year based off my projections, it's going to be over 3,000 people. And going from zero people to 3,000 people in roughly two years' time frame, is very eye-opening to me. And I've reflected on that several times. And just the speed at which that came. And I got to this point where I've been interviewed now a couple of times on podcasts. And I'm looked to for a lot of different direction from others online and in my network and people finally through social. So I've gone from a medical device expert and resource in that field to within two years. You're building a portfolio of business and you're starting to build a reputation. So when I look back at all of that, it's all kind of a wow. Quick break from the podcast to let you know that the two Bootsley books that we brought out, the BookDirect Playbook and the BookDirect Blueprint are two of the top rated and the best selling in the hospitality category on Amazon. For just two pounds, you can grab both of those books right now. The foundations and the structures that you need to put in place is in the blueprint. And then for a 101 mark in tactics, that is in the playbook. So go and grab a copy on Amazon. Now just type in BookDirect Playbook or the BookDirect Blueprint. And we'll see you on your side. That's amazing. And one of those things which I would say to hosts is you don't realize the reward but those 3,000 people that you're going to be hosting, you're actually probably hosting them for some of the best times of their years and some of the best memories that they might have for life. You know, like this is the cool thing that we're able to. This is a nice business to be in. We're actually helping people create memories, which is cool. And stick it with the theme of going from your job to breaking into short-term rental industry. There's two questions which come from that. So first of all, when did you know it was time to make the switch? Was there any kind of rules or any kind of structure that you just done? Or was it just a case of going, hey, do you know what now's time? Let's just clean break and do it. Yeah, that's a great question because for me, I think it's a particularly heavy question to answer. And I think a lot of it came from, oh, I know a lot of it came from, at that time, when I was in my career, finding myself a burnout on that hamster wheel. My dad also had a fib, atrial fibrillation, which was something that we treated in our space. There was more of a realization of like, you know, my parents are getting older. My mom had some issues as well. And I was on the West Coast opposite of my family. Not able to see them or spend a lot of time with my family or even participate in family group decks. A lot of times I've just ignored it. So when it came to me being burnout and facing this opportunity to leave my career behind, I really started asking myself a few, you know, baseline questions of, okay, you know, what, what is it that I need in life? What is it that I, what is my purpose? Or what is the, what is the purpose of life? For me, what is my goal? And my goal ultimately is to be happy. They go, okay, so you want to be happy. What makes you happy? And so you answer that question. It's like, okay, well, why do you become, why do you get happiness from these things? And, you know, I get happiness from solving problems, from helping others, and solving problems for other people. And bringing others happiness, like that's what ultimately, as I boil everything down, everything from customer service in the past, from hotels and restaurants that I worked in, to my sales career and even my corporate career. I'm doing, ultimately, was doing something for someone else to bring someone else happiness in some way, shape or form. From there, I had some concerns about leaving my career and was it the right thing to do? What ultimately, I had more concerns about not being true to myself and to my life. Because in the end, it's my life and it's my time here on, on this earth. So how do I want to spend that time? And so I thought it would be very enlightening to go to a nursing home and interview of a bunch of people whose time has run out. And that's a rather deep fault, right? It's, you know, it can be heavy. And if anyone listens to this, and if they're not, if like, I encourage them to let it hit them deeply. Because when you put yourself in that frame of mind that there are, for one, there are people out there whose time has run out. And they know that they're facing that every day. They know that their life is behind them. They have 80 years behind them and maybe only a few months ahead of them. There's not much you can do at that point. And so when I thought about having that conversation with those that were in that situation, it was pretty moving and it puts a lot of things in the perspective. And I decided to realize through that thought process that I didn't need to go there to have that conversation with them because I knew what the answer was. If they were in my shoes and it was something that they wanted to do, they would absolutely or that I wanted to do. They would absolutely encourage me to do that so that I didn't end up on my death that with regrets, like inevitably some of them will have. And I felt like that was my opportunity at that time to leave my career and pursue the thing that I just wanted to try. I didn't have to be successful in it. That was a bigger fear for me at the time. I didn't want to fail. I didn't want to be wrong. But at the end of the day, the thing I fear the most is having run out of time, waiting on my death bed and having regret that I never tried. I really liked that. And that was the most motivating thing for me. And I think if I don't know how, if anybody else really puts themselves in that mind space, I don't know how you can ignore that and take the left turn when your future self knows you should go right. Do you know, it really resonates with me certainly because there is, I mean, there's some sayings online. You can, you people can go and check it out. It is a bit more, but it is a bit deep, but ultimately, definitely do go and check it out where you can see what people have said, you know, some of their regrets on their, on their sort of death bed and that. And ultimately, nobody regrets the stuff they did. They regret the stuff they didn't do. So ultimately, like you say, by just taking that opportunity, taking the chance while you're able to, well, yeah, we, you know, the fear of being successful was one fear, but actually the fear of not trying it was worse motivated you're into doing that. And I find that really cool. And just on the, you said about your thought about going there and having the conversation with them, there's, I don't know where I got this from, but it says that if you picture a mentor or somebody else giving you advice, even though it's your own mind, you're much more likely to follow it. And that's exactly what it sounds like you've done. You've kind of thought about the process, what, what they'd say, and that's helped you to make your decision. And this a great decision-making process. I feel that I've got a number of mentors and whenever I hit a problem or a crossroads, not sure what to do before contacting anyone. The first thing I do is I think, hey, if I was this person, what would I think and what would I say and what would I do? And actually, obviously it's not that person. This yourself giving yourself advice, but by imagining it in third person, you're much more likely to take action, which is, which is amazing. Well, it's funny you say that because it's a regular part of my process and it's just something that has come naturally. It's interesting that you've read that and learned that. It's to me, I think it's always just a voice in my head that's like, I'm always, it's either a voice of my parents or a voice of a teacher or a mentor in the past, or it ultimately has to go sort of morphed into my own voice now, coaching myself, checking myself. And again, in the third person, and I found it to be extremely effective. You trust it 100%, don't you, as well? At the end, you start to the more that you exercise that muscle of going, hey, this is what I think I should do. You go off and do it, you sort of exercise that muscle. So one of the things I'd love to ask is, what is the transferable skills that you've taken from, you mentioned a lot of your history there, the sales, the customer service, obviously the medical data side of things, what would you say the key skills you've brought across from your other careers into short-term rental and why? Well, I think first is customer-focused mindset. So that being our guests, of course, and being an hospitality, we better put guests first. So in sales, it's of course very customer-centric. We need to be there for them, we need to solve their problems and we need to add value. And we need to be responsible, we need to give them a voice, we need to make them feel like they had a voice. And really all of those things apply in hospitality. So from the ground up, my places are designed, furnished, and start with items that take the guest experience into account. I want everything to be smooth. I want to reduce friction or eliminate friction altogether from the timely check-in or rather from the time they book, from the time they check out. And if there is an issue, if there is some friction somewhere in that process, I want to make sure they feel like they have a voice and they feel validated in that. So it's very rare that I will push back on a guest. And honestly, the only time I can think about doing having done that was this past week and that's out of over 300 states. So I think the guest focus or the customer-centric mentality is first and foremost. Second is defining a process. I have my processes set up to scale. And so that was something that I did in my previous role when I was managing the software portfolio for the U.S. A lot of things we do, we define a process and we build out that scalable process and launch it in different markets all around the country. And then sometimes I would relay that to other markets across the world. So on this smaller scale, defining a process really is through my communication schedule and also my schedule with my cleaners. So I have almost 90% probably, if not more, of my process of communications automated through various processes using hospitable as my property management software. And then of course, price labs, dynamic pricing. Those two tools for one are a mentally valuable one. It comes to establishing a process on the guest's looks. They get a welcome message. I'll let them know what other messages they should expect to come. Then they get another message three days prior to check in. Then they get a message of the day they check in and two days ahead of our day ahead of checkout and so forth. And that makes sure that the burden of communicating with guests and running the business doesn't deter me from taking on more properties and growing my business further because I've uploaded that to technology. So I can't or I'm a lot less likely to feel like it's a heavy lift to add another property and therefore that makes growing my business more attainable to me personally. The third piece would be using data to make decisions. The first part of that is of course the property analysis to make sure that this will be a worthwhile venture purchasing this property. So we'll cash flow and meet my objectives. But the second piece is on the backside of that which is more of measuring my results. So at least property ordered my daily rates. What's my lead time? How can I how can I leverage lead time to customize my pricing on price labs in my lead times 30 days. I'm not going to do last minute discounts until maybe two weeks out or seven days out. Also using the conversion metrics that you see on Airbnb to hone your on your listing and do some AB testing to see what's really working. So I've been testing zero cleaning zero power cleaning fee. I've tested 99 dollar cleaning fee and I've tested the full standard clean fee and things of that nature use data to help drive my actions and ultimately impact our business. If you're struggling on how to get direct bookings and overwhelmed on where to start then I recommend you go and book in a call with Boosley and our team right now. We can walk you through exactly what we're offering, how we can help you and give you a portfolio of websites that we have worked with that are matching not only on niche but could be in your location as well. Boosley has helped over 2,000 hospitality businesses all over the world increase their direct bookings and if you are interested then all you need to do is go to boosleyboostly.co.co.uk or slash call and book in an appointment with one of our sales team. That's cool. So it sounds like you've got some I'm drawing people's attention to those ones that you mentioned there. So first of all hospital and for anybody who hasn't used hospital this is an awesome PMS especially if you're getting started between sort of one and 20 properties really it's ideal. Yeah so hospital is awesome for hosts who are looking to make messaging a lot easier as Jason does there. Price Labs is amazing when it comes down to the making your job easier basically price labs will know about what is happening in the area so any event any kind of holidays things like that you'll be able to have a higher price for and certainly when I did my originally and I use price labs for my business it actually added 12% to my bottom line profit you know so that is something which can really help you with profit there. So one question Jason that I'd love to ask you is what would you go back and tell yourself at the start because there's going to be people listening to this who are thinking you know they might be in a career similarity self thinking hey I can't afford to come out of this what advice would you have for them and you know to get started. Expect discomfort. I think that a lot of people try to get to the point where they're comfortable taking risk or comfortable going out on the limb or putting themselves out there in one way or another but I was certainly one of those people and it took me a lot of I think self-reflection but also you know listening to thought leaders to understand and accept that failing is not the end all be all is failing is not a big deal and then to the day you learn so much from failure you learn so much from the process that even led up to the inevitable failure but to continue that one of the most important things I learned was that you don't need to know 100% of the things that you think you need to know before getting started and I am an analysis paralysis poster child that are so many things that I wanted to do in my life that I haven't pursued because I just didn't know all the answers of you know how to get started what then what do I do and then what do I do after that and what I do in this situation the reality is is what I've learned from others but also from my own process is 80% is all you need to know as long as you can educate yourself inform yourself about 80% of the information related to whatever it is that you want to pursue you'll learn the rest of the 20% on the journey so learn from people like Liam learn from people like Mark learn from people like me if you want there's a ton of people online that you can learn from and that have they have blazed those trails and there's no reason to feel like you have to make that lift on your own that's cool that's cool and thank you for the mention there um so as we reach towards the end of these we love to just do a couple of quick fire sort of questions um if you could visit anywhere on your wish list to travel to where is that place and why Norway Norway is an absolutely beautiful landscape or at least it is on social media I can say so that's proof that social media marketing works the weather is a bit different than what I'm comfortable with but in terms of environments that I want to be in and I think it's a very wholesome place to ground yourself and get back to your roots and clear head and put things back in the focus it definitely is on is on my list I've seen those Instagrams that does look amazing um what does the future for your business look like yeah for me at this point I'm in the Nashville market um my goals strictly was to get to this point with my portfolio to be income neutral with my career so to now that I've established that I want to look or I am looking in other markets so I could grow my portfolio and also begin helping others so I do some consulting I've started building out some tools to help others I'll be posting about those and there'll be links to those tools a lot of them if not all to them will probably be free a lot of what I like to get out of work it's not just money it's I want to I want to have a sense of reward by helping people that also are taking action that makes sense that makes sense and we love to finish with this question which is there a mantra or a saying that really resonates with you there is I think the the first quote that I ever remember reading when I was a kid is the path well-trodden often leads to nowhere and I've remembered that quote for probably 30 years and I think it's just because I've resonated with me because I was always a little bit different and essentially it's just saying that if you want to achieve something different than the others others are than those around you then you can't do what everybody else is doing you can't follow the path that everybody else is following and to some degree you have to think for yourself and make decisions that aren't common decisions so for me that's been a very powerful one I think throughout my life thank you Jason and yeah rings rings true so we've learned a lot obviously about your journey I certainly feel we've covered the field of fear and don't do it anywhere and the something which I'm going to take away from this podcast is that ultimately we aren't here for a long time we you know we are here to enjoy ourselves and when it comes down to apologies if you're watching on YouTube my camera's gone off again but for the purpose of the podcast those listening you've got the opportunity to do it now so if you're a host who's thinking about getting a short term rental or there's an opportunity that you've got which you're just wondering whether or not you should do it well you know like Jason says get 80% of the information then make the decision just just make that decision at the end of the day nobody's going to do that for you and it's something for you to take away from this podcast so Jason thank you so much for spending your time with us and telling us your story here on the behind the host podcast with with Bruce Lee we know there's a lot of places that the listeners can put their attention and we really thank you for putting it with us if you think you've got value from this podcast please do share it with people who will find it interesting and give it a like give it a subscribe and yeah we really thank you for spending this time was it anything we missed before we bring it to a close no I think that yeah I'm starting to post content on my Instagram page and that's at JW Reese our EEC and posted some material there on using artificial intelligence to help you host with also the variety of other topics including some of the motivational things that we discussed here but I think that at the end of the day you're never going to be comfortable leaving their plays of comfort and to realize that is I still to this day if I sign on another property I am nervous at the signing table and I have been uncomfortable and even nauseous every time I sign on a property there's no way for me to know first certain that it's going to work what all I can do is participate and play the game educate myself try to reduce my risk through information and then take a step forward and at the end of the day you got to get comfortable with being uncomfortable and I wish you well on your journey wherever that thank you Jason and just to confirm for everybody listening you can go and check out Jason's journey at JW Reese which are WCE I will add that to the show notes and also he's got an awesome link tree where you can see his epic properties which is the normal which is www.linktree which is TR.EE forward slash JW Reese and you can check out his awesome properties there so thank you Jason for spending your time with us today and yeah thank you again for the Bruce Lee listeners we'll see you on the next one bye for now