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 Boostly 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 bookings. And confidence is something that we're talking about. Today we do a mini series on the Boostly podcast which talks to a short term rental host, somebody who has started their journey, who has felt that fear and and has got started and is now helping to motivate others to do the same. So this is the miniseries 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 his journey and how you can get started yourself. So let's dive into it. Rhys, 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 device. And after about 11 year old long and successful career there, I got restless. I saw the business there from multiple different angles and ultimately decided that along with some burnout, I decided now was the time to dive into the entrepreneurial journey that I'd always kind of felt a pull to do. And every B was kind of an intersection of a lot of different interest of mine. So I dove 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 let that happen again. So I got started in 2020, late 2020 and now this 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 I 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, 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 gonna let the house pay me back for that. So that's how I'm using the, the 0.5.

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 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 were 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 felt extremely fortunate to have found that line of work. It was rewarding both personally but also financially. 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 copilot for the physician and together we would go in to fix that patient. Oftentimes we fix their heartbeat within a split second of finding the right location. And a lot of that had to do with the insight and navigation that I was providing or eventually my team was providing. It's a 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 the further I got away from that reward, the patient reward, 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 led some of our key programs and initiatives. And again, very rewarding because it was complex, it was fast moving, etc. But at the end of the day, it burned me out. So the discomfort that I faced was leaving a career that I had built that I absolutely loved. I worked for Johnson and 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, didn't feel fulfilled at the time. I no longer felt how I did earlier in my career and from that position in 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 or 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. 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 on site 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? You still work in the same job or are you now in property fully or in short term rental? Fully.

No, I went full time self employed last July.

Oh, congratulations. That is. That's amazing to hear. So what has been some of the wow 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 wow moments along the way?

I think the first wow 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 0 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 it just the speed at which that came and I got to this point where I've been interviewed now a Couple times on podcasts and look to for a lot of different direction from others on online and in my network and people find me through social. It's like. So I've gone from a medical device expert and resource in that field to within two years building a portfolio of business and starting to build a reputation. So when I look back at all of that, it's all kind of up. Oh wow.

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That's amazing. And it's one of those things which I always 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, 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 sticking with the theme of going from your job to 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, 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. Well, I know a lot of it came from at that time when I was in my career finding myself burn out on that hamster wheel. My dad also had AFIB 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 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 texts, a lot of times I would just ignore it. So when it came to me being burnt out and facing this opportunity to leave my career behind, I really started asking myself a few baseline questions of, okay, what is it that I need in life? What is my purpose? Or what is the purpose of life for me? What is my goal? My goal ultimately is to be happy. 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 get happiness from these things? And I get happiness from solving problems, from helping others and solving problems for other people and bringing others happiness. 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. But 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 a bunch of people whose time has run out. And that's a rather deep thought, right? It's, you know, it can be heavy. And if anyone listens to this, and if they're not, if 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's. It puts a lot of things into perspective. And I decided. I realized 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. To do that so that I didn't end up on my deathbed 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 things 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, laying on my deathbed and having regret that I never tried.

I really like 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.

You know, it really resonates with, with me certainly because there is, I mean there's some sayings on online you can, you people can go and check out. It is a bit more, but it's 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 deathbed 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 what's motivated you're into, 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 they'd say and that's helped you to make your decision. And there's 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, it's yourself giving yourself advice. But by imagining it in third person, you, you're much more likely to take action, which is, which is amazing.

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. To me, I think it's always just a voice in my head that's like I'm always. It's either voice with my parents or voice of a teacher or a mentor in the past or ultimately has 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. So, yeah, I think we're on the same page.

You trust it 100%, don't you? As well at the end that 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 are 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, you know that being our guests, of course, and being in 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 responsive. We need to give them a voice, we need to make them feel like they have a voice. And really all of those things apply in hospitality. So, you know, from the ground up, my places are designed, furnished and stocked 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 time they 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, you know, 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 US And a lot of Things we would 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 immensely valuable when it comes to establishing a process. So when the guest books, they get a welcome message, then I 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 the day they check in and two days ahead of, or a 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 offloaded 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 it will cash flow and meet my objectives. But the second piece is on the back side of that, which is more of measuring my results. So of each property, what are my daily rates, what's my lead time? How can I, how can I leverage lead time to customize my pricing on Price Labs? If my lead time's 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, hone your listing and do some A B testing to see what's really working. So I've been testing 0 cleaning, $0 cleaning fee. I've tested $99 cleaning fee and I've tested the full standard cleaning fee and things of that nature. I use data to help drive my actions and ultimately impact my business.

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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, hospitable. And for anybody who hasn't used Hospitable, it's an awesome PMS, especially if you're getting started between sort of one and 20 properties. Really, it's ideal. Yeah. So Hospitable is awesome. For hosts who are looking to make messaging a lot easier as, 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 events, any kind of holidays, things like that, you'll be able to have a higher price for. And certainly when I did my, when I did mine originally and I use Price Labs for my business, it actually added 12% to my bottom line profit, you know, so that is, is something which can really help you with, 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 similar to yourself thinking, hey, I can't afford to come out with 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 a 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 listening to thought leaders to understand and accept that failing is not the end all, be all failing is not a big deal at the end of the day. You learn so much from, 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 a hundred percent of the things that you think you need to know before getting started. And I am an analysis paralysis poster child. There are so many things that I've wanted to do in my life that I haven't pursued because I just didn't know all the answers of how to get started. Then what do I do? And then what do I do after that? What do I do in this situation? The reality 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. So as we reach towards the end of these, we love to just do a couple of quick fire sort of questions. 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, I think it's a very wholesome place to ground yourself and get back to your roots and clear your head and put things back into focus.

It definitely is on is on my list. I've seen those Instagrams. That does look amazing. What does the future for your business look like?

For me, at this point, I'm in the Nashville market. My goal strictly was to get to this point with my portfolio, to be income neutral with my career. So now that I've established that I want to look or I am looking in other markets. So I'd like to 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 will be links to those tools. A lot of them, if not all of 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 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 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 it 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 or 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, it rings true. So we've learned a lot, obviously about your journey. I certainly feel we've covered the feel of fear and do it anyway. And there's something which I'm going to take away from this podcast is that often 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 the time. Was there anything we missed before we bring it to a close?

No, I think that I'm starting to post content on my Instagram page and that's at jwreece R E E C E. I posted some material there on using artificial intelligence to help you host, but also a 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 your place of comfort. And the reason I say 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've signed on a property. There's no way for me to know for certain that is going to work. But 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 takes you.

Thank you Jason. And just to confirm for everybody listening, you can go and check out Jason's journey at JW Reese, which is rwce. 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/jw rees 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 boostly listeners. We'll see you on the next one. Bye for now.