WS1377: Overcoming Fear of Real Estate Investing | Jay Helms

Are you one of the many people who want to invest in real estate but never actually get around to doing it? You read books, listen to podcasts, join webinars, and even enroll in courses to get educated about real estate investing. And yet, you get paralyzed by fear and end up doing nothing.

Watch the episode here:

Listen to the podcast here:

In today’s episode, we talk to Jay Helms, founder of W2 Capitalist about overcoming fears in real estate investing. He details how he and his wife broke through the fear barrier with their first scary step to investing. Learn what masterminds are and how they can help you rise above your paralyzing fear and encourage you to take action. Listen now and understand the mindset that propels you from intention to action and then to success in RE investing.

Key Points From This Episode: 

  • Jay’s initial background in real estate investing and that first big scary step.
  • Why Jay believes that the first scary steps should always continue to happen.
  • How Jay and his wife arrived at a mutual decision to take their initial biggest plunge in investing despite the fear of bankruptcy.
  • Jay’s tips on how to break through the first scary step of investing.
  • Jay lost his W2 job during the pandemic, went full-time in real estate investing, and has been traveling with his family all over the country in the past year.
  • What is a mastermind and why is it a helpful way to overcome fears in real estate investing?
  • Jay’s virtual mastermind group and its structure, flow, and direction.
  • Why Jay encourages joining a mastermind that rather stretches the member financially. 
  • Jay’s predictions on the real estate market for the next six to twelve months.
  • His best source for meeting new investors and the most important metrics that he tracks.
  • The main contributor to Jay’s success; his way of giving back; and his contact details.

Tweet This!

“You cannot eliminate risk. But you can make a really good educational guess based on what you know, and what other people who have gone before you know.”

“It (mastermind) is getting around like-minded people who are going to not only give you ideas of what to do next but keep you accountable.”

“I would encourage everybody to join a mastermind that is going to stretch you just a little bit financially because you’re going to take it that much more seriously.”

“Not everybody invests for the same reason.” 

Links Mentioned in Today’s Episode:

Jay Helms on LinkedIn

W2 Capitalist website

Schedule Virtual Coffee with W2 Capitalist – Jay Helms

W2 Capitalist on YouTube

W2 Capitalist on Instagram

Best Places website

75 Hard

Operation Underground Railroad (O.U.R.) website

The Family Board Meeting by Jim Shiels

About Jay Helms

Jay Helms is an Amazon #1 best-selling author. He has been featured twice on, and is the founder of the W2 Capitalist, a mastermind community for aspiring and experienced real estate investors. Timid, apprehensive, and fearful about purchasing his first single-family rental, Jay now owns over a million dollars in real estate assets and escaped the rat race after just 6 years of side hustling in real estate investing. Knowing that closing on the first deal is the biggest hurdle and mental roadblock for new investors, Jay has a goal to help one million people create multiple streams of income, achieve financial freedom, or build legacy wealth through real estate investing. When their family of five is not traveling the country, Jay and his wife, Cassie, reside in Gulf Breeze, FL with their three kids.

Full Transcript



Jay Helms (JH): First big scary step, you know, I still go back to that first property that we bought. I sit down with my wife and it was a $25,000 purchase. We were sitting there and I was like, “what if we go bankrupt from this?” You know, we were living paycheck to paycheck. And it was just one of those things where we finally felt like we were taking the biggest plunge of our lives.

Whitney Sewell (WS):  It can be so scary to take that first step into a new venture. It can be so scary to put all your life savings into this new thing. You have big hopes, you have dreams, you want to make things happen but you’re gonna risk everything you have possibly and lose it. If you do lose it, what’s the worst that can happen? 

Our guest today is going to talk about just that. He’s gonna talk about that scary first step but what he did he and his wife and they put everything up to make it happen to take that first step. He’s gonna go through that. He’s helping many other people to do the same thing now. He’s gonna help you think through what’s the biggest fear? What’s the worst that gonna happen but also even masterminding. He has a mastermind, he’s going to talk about the importance of that. You’ve heard that many times on the show now. If you’ve not thought about a mastermind or joining one, I’ve been a part of many, I would encourage you to look into joining a mastermind. There’s something about being around a group of guys or gals that are motivated high achievers. It just brings you up in many ways. And it will also allow you to help other people, right, you’ll be able to bring them up in ways that you’re an expert. So, look into a mastermind, and he’s also gonna help us with numerous other things. But his name is Jay Helms. He’s an Amazon number one best-selling author. He has been featured twice on and is the founder of the W2 Capitalist, a mastermind community for aspiring and experienced real estate investors. He’s gonna share many things with us today. He’s got lots of experience in many different parts of real estate. Right now he’s traveling all over the country with his family while being a real estate entrepreneur. So, that’s one of the perks right? Being able to travel, being on your own schedule, go places. However, he’s still very active and very busy. He’s making it happen even while on the road which is impressive. I know you’re gonna learn a lot from Jay today on the Real Estate Syndication Show. 


WS: Jay, welcome to the show. Honored to have you on. I know you are good at helping people make that first scary step. It is scary. No doubt about it. It’s so scary but we all had to do it. And then often we have to continue to choose to do the scary.

JH: The first scary step, yeah. 

WS: That’s right. And sometimes that fear doesn’t go away right away. That’s for sure. And so welcome to the show, give the listeners a little more about who you are, maybe your business models, and some real estate ventures you’ve been in. Let’s dive in.

JH: Whitney, thank you for having me. I’ve kind of sat on the sidelines and am envious of what you’ve done with your podcast. So, it is an honor to be here and in front of your audience and whatnot. That first big scary step, you know, I still go back to that first property that we bought. And I sit down with my wife, and it was a $25,000 purchase. I’m sitting down with my fiancee at that time, now wife, and I’m like, what if we buy this? Excuse me, she was my wife at the time. Let me get that timeline straight. But we were sitting there. And I was like, what if we go bankrupt from this? You know, we’re living paycheck to paycheck. And it was just one of those things where we finally felt like we were taking the biggest plunge of our lives. At that time, it was. And it’s so funny, you mentioned those first scary steps. I think those first scary steps should always continue to happen. I kind of feel like maybe I’m addicted to them. I don’t know. I don’t know if I have a problem with that. But it’s almost like, I don’t want to compare myself to somebody who goes skydiving for the adrenaline rush. But it’s one of those things that I enjoy getting into that first step kind of scary thing with new ventures. And so that kind of leads me to the question you asked, our background. We started in single-family, quickly moved to small multifamily. We had maybe three doors in our portfolio, and we GP our first syndication. From that, we’ve been an LP and joint venture. As of most recently, we’ve done some short-term rentals and started doing some note investing. So, the full gamut of investing. And that’s one of the things I love about real estate investing, you have so many different avenues you can go after, and so many things you can do. But when it comes down, if I look at our returns, so far, the multifamily deals that we’ve been a part of have provided the best returns. So I don’t know why I’m drifting away from that other than just my own curiosity.

WS:  Yeah, I don’t know, either. Jay, you mentioned a couple of things there that I wanted to just highlight. You said you all were newly married and I can relate to this. So, we bought our first rentals when we were probably been married a year roughly, and man, a ton of stress. We were remodeling our first house that we were living in at the same time. I mean, I was working the worst schedule as a police officer, it was chaos. But you know, a couple of things you mentioned $25,000 property, I think you said, and you all were asking what if we go bankrupt over this? Well, I mean, because it seems like such a big deal at that time. It is a big deal to go bankrupt, I don’t care where you’re at in your financial journey, but 25k, newly married, the biggest plunge. How are you all on the same page and moving forward with that type of investment, you know, living paycheck to paycheck, as you mentioned?

JH: Yeah, it came down to the prenuptial agreement. Totally kidding. 

WS: I was wondering where this was going.

JH: This is one of the things I talked to you about, people who come to the mastermind or are interested in joining or just getting into real estate investing, if they are married, or they have a fiance, I asked him, what does your spouse think about it? A lot of times, actually one of the things for our mastermind members is for just office hours. Sometimes, the members are coming in, they’ll bring their spouse in, I actually become a marital counselor. And I throw out the disclaimer, hey, I’m not a marital counselor. But at the end of it, so far, there’s been some really good conversations and kind of breakthroughs for these couples to get on the same page. And that’s hugely important. My wife and I actually dated, and quite frankly, we lived together for about five or six years before we got married. During that time, we did a live-in flip together. And we kind of figured out that if we could survive that, then we could probably survive anything. But it really came down to you know, I was the guy who had the reservations, and she was the one that was kind of pushing and said, no, you shouldn’t be worried about this. This shouldn’t be that big of a deal. So, that whole saying, for every strong men, there’s an even stronger woman standing behind him, that definitely plays true. It doesn’t mean that we didn’t come out of it with our bumps and bruises. And, I’ve finally learned that any design decisions are hers. She comes up with the ideas and I figured out how to execute it. So, a lot of bumps and bruises to figure out how to work together and what works out best for us. I’m more focused on financials, and she’s more focused on looks, and sometimes look and appeal don’t necessarily match up with the financials, right? We’ve learned from one another over the years to do that. We still argue, and we still fight over things of that nature. But at the end of the day, it’s not going to ruin our relationship. Our kids will. I’m kidding, kids. If you hear this one day, they’re seven, five, and three, they’re not in the world of podcasts just yet. 

WS: You know, help us though, to break through that first step, Jay. It is so important, would you elaborate on how you and your spouse are on the same page moving forward and making this kind of investment? It’s so crucial if you plan to continue, no doubt about it. But help us break through this scary first step. What do you see? You’re talking masterminding with a lot of guys and gals who are and maybe, they’re struggling to break through or maybe syndicate that first deal or you know, even maybe they’re trying to buy the first single-family rental or whatever it may be. What are some of those simple steps here or questions you ask them to help them get started?

WS: To help them get started, I actually (ask), hey, what’s your biggest fear? What is your biggest fear and a lot of them come down to,  well, I’m gonna go bankrupt, just like me. And I’m like, alright, let’s talk about the possibility of that actually happening. So, we walk through these different scenarios. It’s all about handling objections. And this comes from a sales background that I have. I tell myself a lot of different stories as I’m sitting down thinking about different investments and thinking about different opportunities throughout the years. I will sit there and I’ll tell myself the worst-case scenario that can happen. I’ll freak myself out, and then I’ll open up and share with my wife. She goes, well, that’s kind of absurd. When has that ever happened? When is that going to happen? And the likelihood of it happening is very rare. But, as being, I would say, the household, the father, and you know, the protector, provider, presider, if I can still run McCullers’ tagline there. For our family, it still falls on me or I feel like it falls on me, right? And so that pressure does. So I’m thinking of all these different things.

Something I’ve learned over the years is risk is always going to be there. You cannot eliminate risk. But you can make a really good educational guess based on what you know, and what other people who have gone before you know. And that’s where the power of the mastermind is. You don’t have to do this alone, you don’t have to. There are people out there like you and I who have gone a little bit further than a newbie. And then there are people who are out there who have done a lot more than you and I that we lean on. And the real estate investing community is one of those. I’m so amazed at how much people want to give back and help others get in the business. It’s incredible. Like, I don’t know why we do that. Because we’re basically training our competition, essentially, but we do. We help them. The biggest thing is identifying the risk, but then walking down that path and saying, okay, how big of a risk is it. We just made a change on one of our insurance policies. We had a $25,000 deductible on a million-dollar property. That’s not very smart. If your risk tolerance is very low, it’s very smart. But with the way the insurance prices are being adjusted these days, and going up, it doesn’t make much sense. Our risk tolerance, along with our partners risk tolerance, has changed a little bit. So, we bumped it up to $25,000, lowered our premium tremendously. And it’s just one of those things where, okay, it’s a million dollar property, there’s six of us, if we can’t come up with $25,000, if it’s not in our reserves, then there’s a bigger problem. You know what I mean? So, it’s about walking yourself through those stories of worst-case scenarios and realize that chances are they’re not going to happen.

WS:  Yeah, I know a couple of things that I had to think through when we were getting started and making that first big decision. Like that was like okay, if we do go bankrupt, which obviously, you hope doesn’t happen, but man, still what’s the worst that can happen? Even if we lost our home and everything, we still live in America. Most likely you still have a family member, somebody that’s going to let you sleep in the basement for a few weeks.  You’re not going to be like out under the bridge. I mean, most likely, more times than not. As you said, we just think the worst, and we dream, this big horror story up in our minds, and it just puts so much fear in us. I’ll give you an example, my grandmother, she’s 94. She’s always so fearful of me losing a bunch of money. And I bet, you know, she lived through the Depression. I mean, think back, when she was little, I they really had nothing, lived on dirt floors. I mean, it was really hard times. So, I try to share with her every once in a while when she says something like that.  I’m like, you know, even if that happens, which, obviously, we’re working our hardest to ensure that it doesn’t, and we understand our risks, all those things. But even if it did, I’m still starting back where I began before. You know, I still gained a lot and think about all the knowledge and the network and the people and all the learning that’s taking place, even if, the worst-case scenario happens.

JH: Yeah, one of the things about, bankruptcies always scared me until recently. And you know, it’s one of those things where if you embrace your fears, are they really that fearful? You know, are you really that afraid of them? And I keep telling myself that sort – what’s the worst that could happen if we ended up there? If we ended up there, and it’s not going to happen just based on one investment, it shouldn’t, right? And we’re to the point now where a lot of things gotta go wrong for that to happen unless I just can continue to increase my risk tolerance and then, I would wake up one day be like, oh, crap, what was I thinking? But that’s probably not going to happen based off of Mr. Conservative here.

WS: Well, what are the risks if you don’t try, right? If you don’t take this?

JH: Well, and this goes back to a part of my story, as well. So, May of 2020, May 1st of 2020, I know the day because I now celebrated it as one of the better – not up there with weddings, anniversaries, or birthdays – but one of the best days of my life. I got a call from my boss, and he said, hey, I hate to do this to you. But you know, with this Covid stuff, we’ve got to make some cutbacks. Unfortunately, you’re one of them. You know, that hit hard. I was not expecting it, totally out of left field. At that time, I was running a sales team. And over half the sales team got let go as well. So, they’re all calling me, hey, what are you going to do? What can I do? What are you going to do? And I was like, well, you know what, I’m not gonna do anything. What do you mean? How do you not have your resume already ready? I was like, well, first of all, we just had that conversation 30 minutes ago with my boss. Secondly, you guys know I invest in real estate and I said, I’ve been investing for a while, more comfortable now. You know, we’re comfortable to the point where I don’t think I’m gonna go back to the W2 world. At least that’s where my head’s at. And they’re like, how can you do that? I gotta find a job. We’d be a reference point. I said, yes.

WS: That’s too scary. 

JH: Yeah, it’s too scary. And quite frankly, I was like, you know what, you’re right. It is pretty scary. I don’t want to find myself in this situation, again. Talking about those scary first steps continues to happen. It took me about a year and a half to really stop looking for another…I put on that face for those folks at the moment I was there. I was like, you know what, this is what we want to do. And then as we transition because it was a six-figure job, right? One of the things when I got out of that, you know, my wife came to me to say, hey, now that you don’t have – it is like five minutes after I told her what had happened – great! now we can go travel. You know, because she’s been wanting to travel. Like, can we let this sink in just for a minute? Let’s figure out how we’re going to pivot financially and whatnot. And so it took a year for me to warm up to it. But that’s kind of what we’re doing now. We’ve been traveling for the last year. As a matter of fact, June 18 of 2021 is when we left our house. We’ve been back two months in the last year. I’m in a hotel room right now. We’re just doing the whole Airbnb, hotel. We had an RV that we lived in for about six months. But yeah, it is scarier not to do something and just to rely on that one stream of income source. Because I would have been like those other folks who most of them, I have checked up on them because I was pretty close to my team. They’ve job-hopped, they’re on their second or third opportunity since in two years. 

And here I am, I’ve probably closed more deals in the last two years. We think through that before I say that and than I have in the two years prior to that when I had a W2. And we’ve done it all remotely, traveling around. You know, we’ve hit up the East Coast pretty hard in the last year, and it’s just been incredible. We wouldn’t be able to do that if we haven’t made that first scary step and which led to the next scary. The first scary step being buying our first $25,000 property. The next big scary step is buying another duplex, and then the next big scary step was, let’s GP a deal. We don’t know anything about apartments. I don’t like asking people for money or you know, helping them ensure they see this is a way for them to earn money. I don’t like that whole conversation. I can underwrite a deal. I don’t like talking to people about their money. Because growing up, you mentioned your grandmother, growing up in my household talking about money was voodoo. And if you didn’t have the cash to pay for it, you didn’t need it. My dad still drives around town once a month to pay his utility bills in cash. Now, I’m glad he’s getting out. But man, he doesn’t own a checkbook doesn’t own a credit card.

WS:  Well, yeah. The problem is if you’re never willing to take any risk, nothing changes for you, right? I mean, you’re stuck in this grind or in this place you’re in and you have to be willing to step out. You’re definitely not going to succeed further than where you’re at now. Or maybe where your friends are if you’re not willing to do something different than everybody else. I want to shift gears just a little bit, Jay. I know you host a mastermind or have been a part of a number of masterminds. I have as well. And so, I think the listeners, and you said this before we even started recording, a lot of people don’t really understand what a mastermind event is, or what happens at a mastermind or why they’re so important, or how I even find one. And so, talk through that a little bit. You’re more experienced in masterminds and especially hosting one. So, talk to the listeners a little bit about what is a mastermind and why should I even pursue being a part of something like that.

JH: So, Napoleon Hill, who I credit, has been the godfather of mastermind. He gave us the definition, it’s two to three people coming together, a minimum of two to three people coming together to talk about and engage on a like-minded subject. I think this last part is probably the most important – engage on a like-minded subject in a positive manner. So, masterminding is just a group of people who get together. Now there are ideas on the best format, or whatnot, but they’re kind of all over the place. When you go look for one, I was looking around and trying to find one for me. And so by nature, my personality type, I’m an introvert. Now I’m growing out of that, losing the W2, and traveling around, kinda starting to grow out of that a little bit. But, I did not want to meet people in person, I had worked remotely for 10 years before I got laid off. I was very comfortable behind the camera and a keyboard. That’s what I wanted, and I couldn’t find one. So, that’s why I started the one I host now. But part of me telling you that is, masterminds’ structures are kind of all over the place, right? And the pricing of them is all over the place. And so you made this comment earlier when we’re talking about this, that you travel enough, so you don’t necessarily want and you’re not in a mastermind currently, or whatnot. There are masterminds where you have to go maybe either once a month, or once a quarter to a destination where you’re going to sit in a conference room with other folks and you’re going to hash things out. There are also ones that meet maybe on a weekly basis just in your town. 

And then there’s also like the one I host which is completely virtual. So, we meet on Zoom, we’ve got over 20 different virtual calls a month. And it’s just getting around like-minded people who are going to not only give you ideas of what to do next but keep you accountable. That’s the biggest thing, the accountability. The way we structure our calls, we talk about big wins, we get everybody excited, we’re also starting to figure out that that produces a lot of shiny object syndrome. Getting somebody to come in and talk about how successful they just closed this self-storage facility and the returns and how the one that closed a couple of months ago was producing returns. So, everybody starts shifting to, oh, man, I gotta check out self-storage. And then somebody comes in and talks about multifamily investing and the returns they’re getting on it and the capital they’re raising and like, oh, man, I gotta get me some multifamily. 

So, you got to be careful with that. You got to be really solid on your goals so you don’t get that shiny object syndrome. But we talk about big wins. And then we have just a Q&A session. Q&A session basically, we ask a question, anybody who answers has to answer based on their experience. It’s not they’re answering well, I read this in a blog post, or I heard this on a podcast, no offense, Whitney. But, when you’re in the mastermind, whenever you’re in the confines of the mastermind, there is no answer that starts like that. And members call you out. I will call people out. People have called me out. So, tell me more about your experience. I didn’t know you’ve done that before. And like, you’re right, I have not or you’re right, it let me walk you down that path for a minute. 

Then we ask for some accountability items. So, next time we meet, one of the first things we talked about is hey, how did you do? Aren’t you committed to doing this thing last last time we met, did you do it? And there are people who will show up sometimes 15, 30 minutes late to one of our calls because they get to the call time, they’re like, crap, I didn’t do my thing. I gotta go do my thing. Because I’m not showing up to the call empty-handed, you know what I mean? So it’s one of the things that accountability is key. And the other thing I mentioned is price. So you’ve got like location, you’ve got the format and then the price. I would encourage everybody to join one that is going to stretch you just a little bit financially. Everybody’s situation is different on what they can afford but something that’s gonna stretch you a little bit financially because you’re going to take it that much more seriously. If I join a gym membership, and it’s going to cost me $1 per month to join, how many times do you think I’m gonna go during that month?

WS: You’re gonna forget about that dollar?

JH: Probably not a whole lot. But if it costs me a hundred bucks a month or whatever, I don’t know what gym memberships are these days, I tend to do just push-ups and sit-ups and play around with the kids. But you know, let’s just say it’s a hundred bucks a month, then I’m gonna get reminded every month when I check my bank statement, I should have been worked out and chances are the next day I’m probably gonna go work out. So, join one that’s going to stretch you just a little bit financially. And also make a commitment. Is it a year commitment? Is it a six-month commitment? Three months? Whatever the case, because personally, I found out when I can set parameters like that, then my mind gets in a different place. Because then my mind goes, okay, well, this is just a business trip. This is just a business project. I’m going to do this for three months, six months, or a year, and then I’m going to reevaluate, come out on the other end of it and see if it’s something I want to continuously do.

WS:  I couldn’t agree with you more. I mean, as far as this the value of being a part of a mastermind. I have been a part of the number, and I’m still part of some now. I don’t have the time to start my own or have my own mastermind at the moment as we were talking about beforehand. But, I couldn’t agree more. And it’s worth the expense. A lot of people see the big price tag, and many are $25,000, $50,000, even $100,000, you know, or more, per year. And you kind of grow in them, right? I mean, you grow, been a part of masterminds, and then it’s like, after a while, okay, I’m kind of ready for the next level of mastermind or the next group. For a while, you want to be. For a while, you maybe the least experienced person in there. And you’re helping people and as you’re growing, you’re helping, helping, helping, helping, and then you want to be a part of other groups too where other people are continuing to be ahead of you. And so I love that you said, just the accountability, like-minded subject in a positive manner. I mean, we all need that and the accountability in a positive way, as well. I love that. And even though what you said, only answer from experience. That’s interesting to think that way because that’s gonna change who answers and even the depth of probably their answer. I mean, you’re gonna get so much more quality of an answer because it’s like, okay, I have done that and this is what happened, as opposed to, like you said, I read this in a blog. Maybe there are times that’s helpful, but in a setting like that, with people that are so experienced, hopefully, you have somebody that’s actually done this thing that you’re struggling with. So, that’s incredible. And Jay, we’re gonna have to switch to a few final questions but couldn’t agree more about masterminding and hope people will seek that out. Even if it’s like you said a virtual thing that’s once a month or weekly or something where you’re engaging with other people who are holding you accountable in a positive manner. So Jay, do you have any predictions for the real estate market over the next six to 12 months? Anything that’s standing out to you, as far as, hey, because of this thing I’m buying or selling or anything like that?

JH: I stopped making predictions on what the market was. Number one, because I was so wrong all the time. And what I figured out is, we focus on very specific markets. Sometimes, those markets are affected by the big macro stuff that you see on the news, if you ever read the news, I don’t anymore. I’ve kind of unplugged off TV news. I’ve had a sabbatical for like 15 years, and I’m so grateful for that. But, I used to read the news a lot and I don’t do that anymore just because it’s all agenda driven. I’ll see people who will post something about and they’ll grab a little piece of information and try to apply it to the entire masses, and the entire masses accept it as this is going to happen in my backyard. More than likely it’s not. You know, we’re focused on some very specific markets. And we see what’s happening with those markets. We saw what appears to be a shift from a seller’s market toward a buyer’s market. About two months ago, we started to see the shift happen. We paused. We’re essentially paused right now, kind of pumping our brakes to see what happens next. 

We still underwrite deals, we still look at opportunities. The way we’re doing that as we underwrite opportunities now. We’re underwriting at what I anticipate is going to be a higher interest rate, if we were to close in 60 to 90 days. So, we still gotta make sure we’re hitting that. But what I’m finding out is because we’re doing that our prices are lower. I don’t do all the deals anyway. But it’s almost like, I don’t want to say the market leader, but almost the leader for certain individual sellers, to kind of burst their bubble and say, hey, this is not what it’s worth. Here’s what it’s worth in today’s market. And so, we’re just kind of taking a pause from all that. Just kind of letting things settle down just a little bit, also aligns with what our travel schedule does a little bit, too. So, I kind of stopped because one of the things that I realized is folks invest for different reasons. 

There was a lady in my mastermind, she came in and she introduced me to the phrase – tax flow. And I’m like, what is that? Are you saying cash flow? And I’m just not hearing, she goes, no, tax flow. She goes, my husband makes so much money that we need to buy properties so that we lose money for our tax benefit. And I was like, what? She and I had this one-on-one 30-minute conversation going into that. And that made me realize that I don’t know why it took that for me to realize this but not everybody invests for the same reason. For me, to make a market prediction or something like that, not everybody’s in the same market, it just sounds like you know what, I just need to stop doing that. Because I can sit here and say, this is what I think and I may eliminate an audience member because they invest for different reasons. 

WS:  Sure. Now, I just met you personally but I mean, some people are like, oh, no, I’m not buying anything. You know, because of this, or no, I am buying. So, there are a lot of different ways. Anyway, you’ve heard people think about what’s happening right now and if it affects their market or not, as you said, but I agree about the news and they breed so much fear into everybody. It would just keep you all upset if you watched almost any of those. So, anyway, Jay, what’s your best source for meeting new investors right now?

JH: It is through the mastermind, matter of fact. And this is another thing, we haven’t touched on this, but partnerships that develop out of any mastermind. I’ve seen some masterminds give back to the mastermind structure, some of them require you to partner with them on a deal. Or if you find a deal while you’re part of the mastermind you have to bring it to the mastermind first. And mine is not like that. But partnerships have happened naturally, numerous times in that. It’s almost like a filtration process. You get into the mastermind, if there’s an application process to get in, you can assume that other members have done the same thing. So, you get into this idea of, hey, we’re all kind of cut from the same cloth. I just need to get to know these people a little bit better to figure out if we’re actually going to do a deal together. That’s kind of where I spend most of my time, because we’re growing. I used to have this idea of owning thousands. We had thousands in our Facebook group at one time. I switched off of Facebook to get away from the news, again to a more private community, and we’ve got less than 200. But the conversations are very intentional.

WS:  Yeah, so much better. It’s relationships, right? You’re with the same people more often, you’re building tighter relationships than just say a one-off conference. Or, maybe go to two, or three conferences annually. But, you see these people often enough to really understand what they’re into or how you can help each other. Jay, what are some of the most important metrics that you track?

JH: So, when we’re looking at a new market, one of the first things that I look at is population growth. So, if we’re looking at any asset, it doesn’t matter if it’s multifamily, short-term rental, we’re on a short-term rental kick right now. I say that and then I also stayed up to midnight, underwriting a mobile home park or two mobile home parks. And while I’m doing that, I get a text from a broker who knows I invest in this one tertiary market and says, hey, are you interested in the 78-unit, so after we hang up, I’m going to call him and get the details, because obviously, I’m interested. But population growth is probably the biggest thing because I want to make sure, where I grew up, the town that I grew up in, was really supported by two big industries. There was a steel industry there, and Goodyear actually had one, at its peak, it was the largest tire plant in the world. It was actually in Gaston, Alabama. Since then, the steel plant closed down about ten years ago. You can see what’s happened to that side of the town and then you can see now Goodyear’s closed down probably about five years ago. You can see that trend continuing to happen. And so just having personal experience with that population growth is one of the things because homes aren’t increasing value, folks aren’t keeping them up. I mean, you know, the economy grows when transactions exchange, our money change hands through transactions. So, if people are don’t have the jobs, transactions aren’t happening, values not happening, and growth is not happening. So, population growth is one of those things. That is the key indicators that we look at. 

And then we’re also cash-on-cash return, IRR. When it comes to multifamily, those are some of the key ones that we look at. The population growth is the biggest one. Here’s a little tidbit that a lot of people don’t know of. I found this out, this tertiary market that I focused on, I’m afraid to even mention it because I’m like, a lot of folks don’t come and play here because they look at it like I don’t want to invest in that little small town. But if you look at is one of the resources I use for that. If you look at this area, their population growth from 2010 to 2020, it actually shows negative. But here’s the thing, one of the biggest employers, there is one in the state of Alabama’s biggest jail systems. So, one of the biggest prisons is located near this town. And during the last 10 years, the state of Alabama decided to carve that out and not include it as part of the census of the town. So, there are like 1500 inmates that it looks like just disappeared from the population. It wasn’t a huge negative number. So, there is, some growth is happening. I don’t know, this was one of the things where if you get your finger on the pulse, and you really get down in the details, you can find some opportunities and find some places where the competition is less, I should say.

WS:  Interesting. So, you see a negative and it’s like, what caused that? You did dive a little deeper, and it’s like, okay, it was like a clerical thing or just clerical decision really, more so than like something happened and people left. 

JH: Yeah, they annex it out. So, it was more of a clerical administrative task.

WS:  What about any personal metrics? Like, make sure I’m exercising this much or I track how much I benchpress? How many phone calls I’ve made today, or I don’t know?

JH: I don’t exercise a whole lot. So last year, I went through 75 Hard with a lot of my mastermind. I think there’s like nine of us that went through that in the mastermind who said hey, we do virtual happy hours every now and then. We got some drinks in us and we got to talking about man, I need to be in better shape. And next thing I know, I’m signed up for the 75 Hard routine which is Andy Frisella’s 75 days straight of 45-minute workouts. One of them has to be outside, you have to stick to a diet and you have to read ten pages a day and you have to drink a gallon of water a day. I lost about 30 pounds doing that. And so, I still do some of this stuff, but I don’t track it. I don’t do anything. I rely more on time blocking. And you know, like for instance, you asked me hey, do we want to re-record this whole thing? I’m like, man, my schedule. I wished we just sticked to it because my schedule is so packed because when something comes up for it’s time blocked, then that’s where my focus goes. It’s been an interesting shift, because I used to be a total metrics guy, hey, if I make 50 phone calls, then I’m good and I might have that in a time block. But as long as I’m following that time blocks, and there’s days where the kids or scenarios happen, just get off of it. But, I have found that instead of putting pressure under myself to say, I’m gonna make 50 phone calls a day, or get up and go work out, it is more or less, hey, what’s in my time block for right now. And I hate having those time blocks free because I don’t know what to do. I just struggle.

WS:  Do you have an assistant? Or do you set out those time blocks, or somebody does that for you?

JH: I set it out myself. I don’t think I’m big enough to where I need an assistant yet. But I also struggle with delegating. You know, there’s probably some counseling I need in that area of my life. But I do it all myself right now.

WS:  I’ll tell you now, but you need an assistant. You need an assistant even if it’s just a few hours a week, to change your life, somebody to help you out. What’s the number one thing that’s contributed to your success?

JH: Getting out of my comfort zone, and that’s such a huge blanket. I heard this quote the other day. So, we always talk about what I’ve said tremendously is that many, many times I’ve said, when you get out of your comfort zone, that’s when true growth happens. And I heard this quote the other day, kind of rocked my world, true growth happens when you’re tired of your own shit. I was like, wow, okay, I get it. But no, it is one of those things where you get fed up with something eventually, now, you’ve got the confidence and momentum to go forward.

WS:  Awesome. Yeah, you gotta get tired of it enough to make a change, right? To do something different. Yeah, instead of just getting the same thing every day. So, how do you like to give back,

JH: There are a couple of organizations that I’m involved with this year. It’s been a struggle for me to time block appropriately to get involved with them. But Operation Underground Railroad, in the work they’re doing in child and sex trafficking is huge. They’ve got a lot of big names that support them and I’m happy to do my little individual part. On the real estate investing side, I do some mentoring. Matter of fact, I had a phone call yesterday with a guy that I grew up with, and he’s now bought his first rental property. He gets talking about a mutual friend that we both grew up with, and who’s kept up with me a little bit more. And he reached out and said, man, I hear you’re doing a lot of real estate investing. I would love to talk with you. And so just having those mentoring sessions. At times, I feel that it’s not truly giving back because I get more out of talking to them than they probably do to the recipient. So, those are two things that I focus on. I’m tremendously selfish with my time. I don’t feel like I give my kids enough attention. And so we’ve kind of scaled back some of the giving and, you know, things that we’ve done working with different charities and different food drives and stuff like that, because it’s, I don’t know, I feel like I don’t spend enough time on my kids. Even though the life that we live, we’re essentially around each other 24/7. You probably hear him screaming in the background. My wife’s trying to get him out of the house so that we could do this, but you might hear him screaming because they don’t want to go right now.

WS:  It’s no problem, no problem at all. That’s part of having little ones. Most of us bribe them and the listeners and I have experienced that. And it’s a blessing. But as an entrepreneur, it is difficult to feel like you’re spending enough time at home. We feel so pulled into the business and the things we have to do. But it’s so easy to do that and forget about some of the most important things and they are the biggest priority. I would encourage you to look up a book called The Family Board Meeting.

JH: The Family Board Meeting, okay.

WS: It’s a very short book by Jim Shiels. I’m gonna have him on the show soon. I know him. He’s an author but he’s big into real estate. It’s short but it’s gonna lay out a plan for you to have really a purposeful, fun, but interacting time with each child individually. And it helps you to create some moments, especially for us as busy entrepreneurs. You know, it’s great when your child knows, hey, I may not see dad for a week or whatever it may be. But I know this time is coming. Yeah, he has set this time aside for me. And so anyway, I would encourage you and the listeners to look up that book. And I’m gonna have Jim on so we can talk more about that. Because as entrepreneurs, as you know, Jay, man, it just keeps coming at us, right? You know, it keeps coming and we keep trying to knock it down. All these things keep coming. We keep trying to punch them down. And we get so caught up in the fight that we forget about sometimes what’s most important. So, Jay, thank you again for being on the show. And I know you went through that next scary step. You talked about you and your wife newly married, that $25,000 property, you know, but what if we go bankrupt? We talked about that, the biggest plunge right you’ve ever taken at that time and you got to do it. We all have to do it at some point and it may be $2,000 for some, it may be $100,000 but man, you do have to take that first step and to make it happen. But then, you asked us, you talked about, what’s your biggest fear? Often it is bankruptcy but you know, even then, especially living in America, it’s not the worst thing typically, right? You’re gonna learn a lot. It’s not fun but, even you talked about masterminding and the importance of that. So Jay, thank you again for your time being on the show. How can the listeners get in touch with you and learn more about you? 

JH: So, a couple of, and this goes along with the mentoring thing. I actually have a calendar that I make available for everybody. You can find that at Virtual coffee is just one word. So, if folks wanted to schedule a one-on-one time with me, they can. If they want to find out more about W2 Capitalist, just go to And we’re on a lot of social media but we’re active on Instagram and LinkedIn and YouTube the most.



WS: Thank you for being a loyal listener of the Real Estate Syndication Show. Please subscribe and like the show. Share it with your friends so we can help them as well. Don’t forget, go to where you can sign up and start investing in real estate today. Have a blessed day.


Love the show? Subscribe, rate, review, and share!

Join the Real Estate Syndication Show Community:

Related Posts

Leave a Reply