Chris Seveney explores the concept of long-term real estate investing with Jonathan Greene. They challenge popular notions of quick financial freedom through real estate and discuss the importance of patience and strategic thinking in building wealth. Chris and Jonathan, both experienced investors, share insights on the value of W-2 jobs, the pitfalls of chasing trends, and the benefits of steady, long-term approaches to real estate investment. They offer a refreshing perspective on building a sustainable real estate portfolio, emphasizing the importance of relationships, continuous learning, and adapting to market changes. This conversation provides listeners with practical advice on navigating the real estate landscape and developing a mindset for long-term success.

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Building Long-Term Wealth Through Real Estate With Jonathan Greene

Welcome back, everybody, to another episode of the show. I have a special guest. I am joined by Jonathan Greene, who hosts the Zen and the Art of Real Estate Investing podcast. If you have not listened to it, I strongly recommend you go out and listen to it. He had me on it, too, so I can pitch that as well. Jonathan is in real estate. His focus is mainly company streamlined properties. Jonathan is a big advocate on BiggerPockets where he and I go back and forth on some conversations as well. I wanted to have him on the show.

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Jonathan, how are you?

Jonathan Greene’s Real Estate Journey

I’m doing great. Thanks for having me on the show. I appreciate it.

No problem. Why don’t you take a brief minute? You’ve been in real estate for 30-plus years. You’ve seen the last 2008 debacle and probably the 2001-ish tech boom-bust thing as well. I’ve been in five years less than you. Why don’t you share people a little bit more about you?

Thanks for having me on the show. I was fortunate. My dad was an attorney, as am I. He didn’t like being an attorney, so all he did was real estate. Since my parents were divorced, I would see him on the weekends and all we would do was look at real estate from the time I was one. We’d go to yard sales. He’d make offers on every house at the yard sale. We’d look at dumps.

We’d get the foreclosure list from the county records, which was the way before the internet, and we would get access. A lot of times, I was small, so I could climb through the windows. This is old-school. This is how we used to do it. The lists were there. We knew they were vacant. There weren’t even old-school lock boxes then, so if they were not open, you’d go in. I would get in, go around, and open the door. That’s how I got started.

Realistically, I’ve been looking at properties for pretty much 50 years. Over the years, once I turned 18, I started to invest on my own in my early 20s. I had owned a lot of properties because of my dad before. He had always been taking me around. I knew tenants early because we owned a lot of rental properties. He taught me about landlording and why we did it, so I was very advanced.

I went into a career in law, still doing real estate on the side, and then eventually, I got into real estate full-time. I got my license years ago. I built big teams on the on-market side. I’ve continued to invest, but I’ve never been a high volume investor. I’ve invested mainly in single families across my life. I’m getting more diversified as I have more time to wind it down in this back half.

I know you have workshops and stuff for people to share education with them and tell them the good and the bad within investing. One of the things that is overused a little bit is the term, to me, financial freedom. People within real estate are like, “I’m going to, in three years, go buy all these rentals and be financially free.” Most people A) Don’t know what that means, but also, the reality is that 99.999% of the population is not financially free. It’s a dream like winning a lottery. I’m curious about some of your takes on that with the meetups and everything that you host with people.

The Myth Of Financial Freedom In Real Estate

The first thing that comes to mind is that people aren’t chasing financial freedom. They’re chasing time freedom. You can get time freedom for a lot less finance than you expect if you know how to do it correctly. There’s part of the modern investor that’s very smart and more streamlined than we were, but what they’re missing is they’re very short-term focused.

People aren't chasing financial freedom; they're chasing time freedom. You can get time freedom for a lot less finance than you expect if you know how to do it correctly. Share on X

Even though they think they’re going to be time-free, it could only be temporary. If they’re invested in a bunch of bad doors or bad investments because they wanted to scale the number of doors, which people are excited about, and those doors are bad, they might think that they’re financially free until there’s a loan call on one of their big 100-unit multifamilies and then they’re in trouble. It’s a little bit different.

I don’t know that I was ever in search of financial freedom. My dad came from nothing, so he built everything on his own. I was very fortunate. He helped me get that way. I never looked at money the way that people do. It wasn’t because we had money. It was because my dad set me on a path to really focus on how to earn money from money.

People are chasing all sorts of different things because of social media. When people are saying, “I want to be financially free,” the first thing I think of is the FIRE movement and all of the scams that went along with that. It’s not real. It’s more like a social media frenzy. People have forgotten to dig into old-school techniques that you and I both know about. There are people who still read Rich Dad Poor Dad and get motivated. I don’t know if I would follow what Rob Kiyosaki is saying, but when you read that book, you’re like, “This is doable.” It’s about how you’re going to do it and the why behind it.

FIRE, for the people who are reading, is Financially Independent, Retire Early. I viewed it as COVID was a big factor in that because everyone was working from home. The government gave everyone money. The All-In Podcast I listened to had a good conversation about UBI or giving people certain money. They used COVID as an example.

When that happened, all you did was create bubbles of people buying NFTs, Bitcoin, and everything else. People are not good with their money because everyone wants that instant fame. The FIRE movement got people because of inflation. Real estate popped so high that it was like, “You need to get into real estate.”

Something similar is that I have a business, and I run it. Do I want to make money? Yes, but I don’t do it for the money. I could go back out and get a W-2 job and make more money than what I’m probably doing, managing my business as I get it running. We talked about this in the past. Everyone wants that get-rich-quick scheme. My show is called Creating Wealth Simplified. It doesn’t say it’s simple. I try and simplify it for what you should be doing. One of those is thinking long-term, not 12 months or 24 months. It is thinking 12 or 24 years down the line.

One last thing I’ll add about what you mentioned is the number of doors. I’d rather have 1 door that’s doing really well in a nice area and 5 doors that probably cost the same as that 1 in a place where I wouldn’t walk around at night. People are like fishermen. It’s like, “How many fish did you catch? How many doors do you have?” People are bragging about how many doors they have. People I know who have the most doors, you have no idea how many doors they have.

The Pitfalls Of Short-Term Thinking

I agree. People used to ask me how many doors I had, and I would say, “I don’t know. What are you qualifying as a door? If I own 10% of something, I only own 1/10 of each door. Are you doing the math on that?” It didn’t make sense. My dad was an asset hunter, and that’s what I call myself. I like a lot of different things, but I always judge the asset. I don’t crunch spreadsheets too complicated. For flips, I run a spreadsheet. If I’m looking at syndications, someone’s done the spreadsheet for me. I’m looking at, “Is this a strong asset to add to my portfolio?” like I would look at stocks. I look at everything, startups and things like that. It all boils down to what you started that part with, which is short-term thinking.

Probably about 50% of the people who are in search of financial freedom are lazy. No offense, but that’s what they’re after. They’re after something easier. You’re not usually going to get rich if it’s easy. It’s not that easy. You can win the lottery. Guess what? 50% of lottery winners are out of money in a year and go bankrupt. It’s not the money. It’s how you make the money and how you keep the money. It’s not even really about how you save money.

My dad was frugal. People called him cheap. He liked houses and cars, but then he would get his pants at Caldor. That’s his thing. I didn’t want to get my pants at Caldor. I like to get other stuff at Caldor. There’s a lot of advice out there that would say maybe you should get your first property. It works to never go to Starbucks and make your own coffee, but you’re not going to get rich by not going to Starbucks. You’re going to save money and maybe have a little bit more for your first investment. If you do that your whole life, that doesn’t get you rich. Compound interests and compound mechanics get you rich. You can only get that from appreciation, buying things, and trading them along the way like we have. You have to take some losses along the way. Hopefully, not big ones, but that’s how you learn.

Real wealth comes from compound interest and appreciation, not from saving money on coffee. Focus on building assets and making smart investments rather than penny-pinching. Share on X

First, Kaldor is a blast from the past.

I love that place. That’s where I got all my toys.

Leechmere, as well. Lechemere was good. I liked Leechemere. Leechmere was my favorite. I probably asked half my team if they’d ever heard of Kaldor or Leechmere, and they all looked at me like I had six heads. You mentioned that, and part of the problem, too, is on social media, everyone’s always posting, “I made this much on a meme stock. I made this much on real estate. I’m arbitraging rentals. I’m doing this.”

An interesting story I’ll share is that I’ve been cleaning up my CRM database. I hadn’t done it in probably 3 or 4 years. We primarily invest in notes. I have conferences from 2018 to 2022 and I have 2,000 names. I sent people an email, “I’m checking in to see if you’re still interested in the space. I’m cleaning up my database.” More than 25% of those emails got kicked back. Meaning they’re already gone. My response rate is under 10%.

What that shows me is that I don’t disagree that a lot of people who chase certain things are lazy and are trying to get rich quickly. Also, a lot of people don’t know what they want to do, so they’re like, “I’m going to try this.” They never really focus on or try to learn what they’re good at, and then they’re going out and spending $1,000 here and $1,000 there on all these different courses, thinking one of them is going to bring them the holy grail.

Do you know what they do? They keep buying new courses because they think the courses are going to do the work for them. That’s not how it works. They’re expecting this DIY thing to pop and all of a sudden make money. That’s a problem. There are a lot of gurus out there. We’ve talked about this. We talk about it on BiggerPockets. I still submit to almost anybody that in any class that you pay for, mentorship, or coaching program, the materials are going to be at least decent. If you do what they say and meet the other people in that thing, even if you overpaid for it and you don’t think it’s worth it, you can make it worth it.

The reason why people fail in coaching and mastermind is because of user error. It goes back to them being lazy. They thought if they spent $50,000 for FortuneBuilders, FortuneBuilders was going to walk them through the holy grail and they would do a flip for them. It doesn’t work like that. Everybody who’s gone through masterminds will tell you all the relationships are in there. They don’t talk to the person who ran the mastermind anymore. They talk to the 10 people who also paid $10,000 because they had skin in the game. Those people are doing deals together.

 

It’s built all around the same thing. Social media looks attractive. People are talking about things. People are getting baited into buying things. Some people are good salespeople. I’ve bought courses or masterminds and not finished them, but I don’t blame it on them. I blame it on me or I tell them, “This isn’t for me. I don’t like people that much.” Sitting around on a Zoom call, if I’m not running it, I find that I’m not going to learn that much, but somebody else can. You have to build the relationships outside. You’ve been in it a long time and so have I. We both know it’s about relationships. The more relationships that you have, the less “work” you have to do to get deals because you’re always working on deals because you’re building relationships.

 

I 100% agree. A perfect example is I took a course on some LinkedIn stuff and I have not done a thing with it. Am I upset that I paid $200 for this course? I’m more upset that I paid for the course and haven’t done anything with it because I intended to do it. It’s very similar. One thing you touched on with some of these courses that I think about a lot goes back to what you said. When you were a little kid or younger, there wasn’t the internet. There wasn’t like, “I can go pull a list from PropStream or whatever.” There’s an online newspaper. You’re getting a newspaper, looking at public notices to see what’s going on for foreclosure sales, or knocking on doors to figure out what’s going on.

There’s so much information on the internet and it’s good and bad. I say that because people who hustled had a competitive advantage back then. I still believe they do because even though people will subscribe to PropStream, and I’m using PropStream because we use it, they’ll go pull and do a mailing to everybody. They’ll do one mailing, like, “I spent $100, $200, $500, or $1,000.”

It’s the same principle.

That’s not trying. Are you picking up the phone? What are you doing to get more deals? It goes back to what you said about networking. Who are you networking with? Who are you talking with to grow your portfolio?

Think of it based on our experience knowing each other from the forums on BiggerPockets. We’ll both hop in on a forum where someone will post something that says, “Wholesaling sucks, I can’t get this business going. I sent out 100 letters and I didn’t get a response yet.” It’s like, “When did you send them out?” They’re like, “I sent them out three days ago.” It’s like, “You already quit? You have to send letters for six months  to even get a sniff.”

It’s that classic diagram that you can see Adam Grant posted a lot as well as Liz and Molly. It’s a person pushing a rock up a hill. They always get it halfway. If they push a little bit more, it will go over, but they always quit before and then the ball rolls down. To do it again, you have to start all over with the big rock. I’ve always been the opposite. I keep pushing until it’s over.

Sometimes, I decide, “I don’t really want to do this career.” I was an attorney, then in the art world, and then I was full-time in real estate. I like doing stuff. When we were talking in the beginning about FIRE or Financial Independence, Retire Early, I had no interest in retiring. If I retired from a career, I would go and do something else. What am I going to do all day? I like working. I like trying to make money. I like looking at systems. It’s fun, so I have no plans of retirement. I may switch careers again, but that’s the fallacy.

For most people who retire from blue-collar careers like firemen and policemen, there is a high suicide rate for all those careers because you have no purpose after that. You retire at 55, or when government employees have to retire, they don’t know what to do. Not everyone wants to go to Florida, sit around, and play golf. That’s okay for a week, but what are you going to do for the next 25 years? I want to be busy.

It’s the same with me. This is where a lot of people confuse FIRE with entrepreneurship. Not everyone can be an entrepreneur, and not everyone should be an entrepreneur. It’s, “How do I get out of the rat race or the W-2 but also better set myself up? When I do want to retire or leave my W-2, what do I do?” Most people, when they leave their W-2, you’re right. They go to work and do something else because golf or pickleball will get boring or their spouse will want to strangle them because the person is home and bored all day long.

There’s a stat that the highest rate of death is the year after you retire. You lose that will sometimes. For me, it’s the same thing. I’m not golfing every day. I can go golfing. I’ve got my path of what I want to do, but I enjoy what I do. I’ve been in real estate. I love real estate. Maybe someone will eventually fix my brain, but who knows?

Challenging The “Escape The W-2” Mentality

Think about the broken W-2 mentality, which is everybody who’s in forums because we are always there, so bring them up. People who are saying, “I want to get out of the W-2,” are 22. How are you ever going to be lendable? W-2s are great. Honestly, I’m  53. I’ve been an entrepreneur since I left the government many years ago. Sometimes, I think maybe my next move is to go back to something that’s more full-time because it’s steady. I can work remotely. I still run my hours. What’s wrong with W-2? It’s great. You know what you’re going to get. Your weekends are free most of the time.

These people are like, “I want to get out of my W-2 so I can get a 4-family,” and then they don’t realize you have a job times ten because you have to be available 24/7. Your weekends aren’t free of plumbing breaks. The mentality is, “I watched on social media that person’s driving a Lambo from a four-family.” They’re not. It’s leased. They don’t have money. Those doors suck. It’s a C-plus door that is going to be a C-minus because they don’t do the CapEx.

That’s why older school people like ourselves are really important. We know they don’t always like advice, especially my advice, because I’m very straightforward. If they don’t get that, that’s participation things or participation trophies. If you don’t have someone in your life who tells you, “That’s a stupid idea,” you’re going to make bad decisions and you’re going to lose all your money. You’re never going to get to where you want by getting yes from all your friends.

I 100% agree. It’s interesting, the whole W-2 mantra. When I look back in my twenties, I was not close to being mature enough to own real estate. I owned my own property, but I didn’t even take care of it. I was lazy. I was immature. I was at a W-2. I was working for a great company. I don’t like using the term militant, but they were disciplined. That was everything they did from systems and they paid very well, but they also had the best people. I learned from some really smart people. The owner is a billionaire, and he was probably one of the most respected people in Boston when I was up there.

When I came down to the DC area, I worked for a local real estate developer who’s one of the most respected townhome and single-family developers in the area. I was doing multifamily. I started working for a family office that owned a lot of real estate and had a great reputation. When you see and get to interact with people who have A) A lot of money but a lot of power and control, not only how to learn something but how to deal with people and situations, you can’t learn that at 22 on your own.

There was one company I did work for. Between that, everyone had been in a company for 25 years. This was in the early 2000s or mid-2000s, but everyone was from the ‘80s mix. There was no technology and no advancement. Everyone was so used to doing things their way. To me, I didn’t learn anything. As an outsider, you come in and you’re like, “You should do this and that,” and they’re like, “This is the way we’ve been doing it for 20 or 25 years.” When people knock that whole W-2 or say, “I want to be out of my W-2 by 25,” to me, you can easily disagree with me on this, but build a great real estate portfolio while working a W-2.

That’s when you’re the most lendable. It’s when you keep scaling up your W-2 to make more. My first job was with the government for $25,000. It was 1997. When I got out of law school, it was $25,000 for the government but I steadily kept making increases. Guess what? I never paid a medical bill for eight years when I worked for the government. They had the best insurance on earth and I steadily kept getting increases.

We’re looking at things with a longer flow, but people are chasing the wrong things. One thing that I think of all the time is when I worked for the government, and we were all prosecutors, we would all go out to lunch every single day. We were always busy. We’re walking to court. We’re walking here. I was getting exercise. Now, I’m sitting in my office all the time. I go outside and walk because I’m smart, but it’s not the same for me.

You have no camaraderie if you go out on your own at twenty and you won’t go to real estate meetups. You better know people. You’re not going to know anything unless you have friends doing the same things as you. You don’t have to pay for the mastermind in coaching. You can find it out in the world. W-2 is the best for camaraderie. I’m still friends with a lot of people that I was lawyers with. It was a great time to be young and working. It’s weird to me that people are trying to scale it. I love entrepreneurship, but also, how are you going to be lendable? What’s going to be your background so you can get money from other people later? You’re going to pay two times as much as the rest of the W-2 employees have to pay, if not more.

There are courses out there that would teach you to do it subject-to and then get them to seller finance back. You don’t need any money to buy real estate.

I’ve said this so many times. The majority of people who do subject-to or seller-finance deals have money. That’s why they have leverage to do seller finance and sub-to. Pacing strategies are great. I’m not going to do subject-to. I would do seller finance. I’ve done it. I’ve sold things on Seller Finance. You have leverage when you have the money in the background to do it because then you can say, “I’ll pay you more.” That’s seller finance. You’re like, “I can pay you more. No problem, but I’m going to take the terms for myself.” You can’t negotiate that when you don’t have money. What are you bringing to the table? Nothing.

It’s interesting because in our fund, for cashflow purposes, we’ve done some short-term loans to people. One of my mantras in giving people money is I don’t give people the money they are begging for or who need it. Meaning, they have no money and this deal is dead. It’s more of, “I have the money but I’d rather keep it where it is versus go through all the hassle of getting it.” I’m okay with paying you 10%, 12%, or whatever that case may be, especially over a 6-month period because it’s easier.

Some people say, “They could get a bank for 8%.” If you’re worth $5 million and you borrowed $500,000 from somebody for a year and at 8%, you’re $40,000 and at 12%, you’re $60,000, that $20,000 to them is a convenience fee. That is the way they look at it. It’s a complete convenience fee of, “I will pay for the convenience of dealing with not having to go through a full bank and taking 90 days.” We still do everything, like underwriting appraisals and everything along those lines, but it’s a much simplified process that requires you to speak with 1 person, not 27 people in a loan department.

Exactly. That’s a relationship thing. If you lend to somebody who has no money, that’s called a crisis. That’s a housing crisis because they were giving away loans to people who really shouldn’t have gotten loans. No offense to them. I’m glad they got them, but they couldn’t pay them. That’s the whole problem. I’d much rather lend somebody who has the money and I know they have the collateral to do it. That’s smart recovery.

Hard money lenders are looking at the property. When people think of hard money lenders, they’re like, “They all want to foreclose.” No one wants to do a foreclosure. It’s the worst. Who wants to go through that process and try to get it back? Hard money lenders in general have such a bad name because they think they’re charging more. They’re charging more because it’s a convenience fee. It’s what you said. You’re like, “I’m going to give you some of my money. Here are the points. Here are the rates. You haven’t done any flips. That’s going to be 13% in 2 points. Good luck.” We know the asset’s worth it, but we want you to succeed. It’s a win-win if we all succeed in this.

The one that scares me all the time is when people can’t sell a property, so they’ll seller-finance it to somebody who’s not qualified and they jack up the price. They’re like, “At least I’m going to get this much from this person.” I’m like, “How long are you going to get it from them?” They’ve got a 510 credit score and they got $27 in their bank account. Right.

You didn’t take a down payment for the seller-finance.

As we get to wrapping up, I always like to ask people this, whether it’s your own personal story or something else somebody’s told you. All of us have been around for a while. There are 100 pieces of advice we could talk about. What’s one that you like to talk about or a piece of advice to give to the audience regarding investing in real estate and trying to build some type of income stream?

Don’t Rush Real Estate: A Mindful Approach

I’d use my dad’s ultimate quote for me, which is, “Don’t rush life.” I would apply it to real estate. Don’t rush real estate. Everybody says, “Buy real estate and wait. Don’t wait to buy real estate.” That doesn’t mean that taking action is buying. Everyone’s in a rush, as we’ve been saying the whole time. They’re like, “I want to get from A to Z. I want to be a millionaire by the time I’m 21.” You’ve had one job at Chipotle. How are you going to do that? You’re only going to do that if you’re scamming someone. You can’t even hustle that hard. It’s not possible. You have to relax and don’t rush.

He always used to tell that to me when I was learning how to drive. It’s so in my brain. I would miss a turn and I would start cursing at sixteen. I was like, “Now I have to go turn around.” He was like, “What do you care? Where are we going? We’re going to Kaldor. Turn around. It’s no big deal.” That’s what’s helped me with my mindset over the years and it’s why I’m focused on the mindful approach to real estate investing.

Are there a lot of deals in my life that I missed out on? Yes. That’s okay. I can’t buy every deal. If somebody else does well in that deal, then okay. I’d rather miss one. I’ve had very few screw-ups. The market has been the only screw-up. I’ve never completely boned a deal on my own because I’m careful. That’s because I learned not to rush life and not to rush real estate. My price is my price. I’m a very tough negotiator because I was an attorney and all I did was negotiate for ten years straight. It’s like, “This is my price. If you even speak about another price, you’ll never hear from me again because I have no emotional attachment to real estate at all.”

One thing you mentioned, too, is I’ll use the term regret. For me, I don’t regret not buying properties. There were some that I was like, “I wish I would’ve bought that,” or, “I wish I didn’t sell that,” but it’s not like I think about it every single day. It’s the same thing with a significant other from high school or whatever the case may be. It’s like, “I saw him on Facebook.” It’s not like I’m sitting there sticking my head under a pillow and so forth.

It’s one of those things where you can’t change the past. You can learn from it. You keep pushing. I’m the same way. I continue to grow our portfolio wisely and take calculated risks on things. Most times, I like to think things go well. Sometimes, you’ll lay an egg, but overall, I’m not going to bury my head in the sand or go back in regrets. I see a lot of people like, “I wish I did this. I wish I did that.” I’m like, “Stop worrying about all that stuff. It doesn’t matter.”

It’s not going to change anything. It helped me to focus on being calm. I have always been self-aware, but I’ve become uniquely self-aware. I know what I’m good at. I know what I’m not good at. I know what I like. I know what I’m comfortable with. I’m going to focus on that. Regret will kill you. What are you going to do? One deal? Who cares?

There was an apartment in Brooklyn that I was renting when I moved back from Florida. I really should have bought it, but I had a lot of balls in the air at the time because it was 2009 and I was getting crushed on 2 properties in Florida because the economy played games with me. I’m fortunate I knew what I was doing, so I had a good portfolio that could withstand getting buried on a couple.

To be a good real estate investor and to be careful with what you want to build is to meet a lot of people and learn what they did. We can have this discussion so it can help somebody that maybe we’ll never meet not step in the same potholes that we did. If that helps one person, this episode’s a win. Talking to you is a win. We’re friends, but we were friends in the forums for ten years.

What I would tell people is to stop watching social media so much as a learning tool and think of it as entertainment and learning in a bubble. I follow the people I know who bring real information. Other than that, I ignore the algorithm. I scroll through and find what I find. It’s tough out there. I was talking with my son. I can’t blame people for not knowing what to trust out there because it’s impossible.

Podcasts are a great way to learn because if two people can sit down and talk for 30 minutes to 60 minutes, you know they know what they’re talking about. There are no breaks. We’re not re-recording anything. You know people understand. If people aren’t going to show up ever and you’ve never seen them on a podcast or they can’t talk for that long, they’re probably BS-ing you about what they know.

As we wrap up this episode, how can people reach out to you?

I’d love for them to listen to my podcast, which is Zen and the Art of Real Estate Investing. That’s pretty easy to find. My handle everywhere is @TrustGreene. I’m pretty easy to find on social. I’m not someone who says, “We’ll give out my number.” I haven’t answered my phone in five years because it never stops ringing from people I don’t know. I’m easy to find for email on my sites. TrustGreene.com is my hub site. I appreciate being on. It’s good to talk to you again. I always have fun with you in the forums. We’ve been in those forums answering questions for people for ten years. Hopefully, it helps them, but if not, there’s nothing we can do about it.

One of the things that we both have a reputation for, good, bad, or indifferent, is we’re honest with people. I was in a forum and someone was like, “My HOA banned short-term rentals. What should I do?” I’m like, “Follow the rules.” Other people are like, “Do this. Scam them. Sue them.” I’m like, “Why? You’re going to lose. It might make you feel better by doing all this stuff, but accept the defeat, see if there’s a grandfather, and move on. Focus on what you can do to get into a long-term rental, not, “How can I try and screw over an HOA?” A lot of these HOAs and board presidents, and if you’re a board president, I apologize because I was on a board and in HOA in the past, they’ve got nothing better to do than to try and figure out who’s trying to skirt the system.

Your job is to stay ahead of the game and adapt to it as quickly as possible. That is short-term rentals. When you see the regulations coming, pivot early so you’re the first one to be at a 30-day stay. Be the first one to get grandfathered in. See if there are permits. When they start to do hotel taxes, be the first person because then, they’re going to love you. That’s what you have to do when you’re dealing with cities. Don’t mess with cities. I’ve gotten red cards on flips before. You have to play nice even when you don’t want to.

Be adaptable in real estate. When regulations change, pivot quickly. Be the first to comply with new rules and you'll stay ahead of the game. Share on X

Thanks for coming on. Thank you, everyone, for tuning in to this episode of the show. As always, make sure to leave us a like or review on your favorite station. Thank you all. Take care.

Thanks.

 

Important Link

• Jonathan Greene
• Zen and the Art of Real Estate Investing
• Rich Dad Poor Dad
• @TrustGreene – Instagram
• LinkedIn – Jonathan Greene
• TikTok – Jonathan Greene

 

About Jonathan Greene

Real Estate Thought Leader, Investor, and Team Leader. Coach, Podcast Host, Public Speaker, and Podcast Guest Expert.

Founder of Don’t Rush Life | Coaching.

Host of Zen and the Art of Real Estate Investing, The Art of Agency: A Launchpad for Realtors, Dad: A Parenting Podcast About the Role Fathers Play in our Lives, and Assemblage: A Podcast for Creatives Building Something Unique.<

Founder and editor of Assemblage, as well as the Medium publications: Assemblage, A Work of Fiction, Isolation, Know Yourself, Loose Words, The Death of Online Writing, and The Scales of Injustice.

Contributor to Medium, Thrive Global, Highlark, Sivana East, Bigger Pockets, and Inman.

Former prosecutor and criminal defense attorney, contemporary art gallerist and curator, university professor, and school mentor.