How To Achieve Your Lifestyle Design

Podcast episode (How To Achieve Your Lifestyle Design) hosted by Mark J. Podolsky with Scott Todd and guest Deray Olaleye. Deray recounts leaving a Big Four accounting job, buying his first rental (3BR/2BA single-family for $165,000 that initially cash‑flowed ~$250/month), later moving into small multifamily (including a 4‑plex) and ultimately focusing on creative financing and small multis/singles. He worked at a private equity hedge fund managing $26 billion after being fired, used mentorship to accelerate learning, and stresses decisive action ("decide" → kill off alternatives). He proposes an individualized 7-question assessment (hosted at beforethemillions.com/newbie) to match investors' goals, time, and resources to a real‑estate vehicle. Core strategies discussed: owner/seller financing (including subject‑to) and assignment-based approaches (wholesale and tenant‑buyer assignments) to acquire properties with little/no personal funds. Hosts debate niche focus vs. diversification, emphasizing being "an inch wide and a mile deep." Resources/takeaways: beforethemillions.com (newbie assessment), Mark’s landgeek training/Flight School (16-week course via landgeek.com/training), and promotional offers (free $97 Passive Income Launch Kit for reviewers).
Questions this video answers
$165,000
Approximately $250 per month
A private equity hedge fund managing $26 billion in assets
Small multifamily (including a 4‑plex) and then small multis/singles with creative financing focus
beforethemillions.com/newbie (beforethemillions.com newbie)
Chapters
Hey, it's Mark Podolski, the land geek with your favorite niche real estate website, www.thelandgeek.com. i'm super excited for today's podcast guest. But before we talk to our guests, I'd be remiss if I didn't properly introduce my co hosts. You know you love them. Scott Todd from Scott Todd.net landmodo.com you're automating your Craigslist and your Facebook postings. Posting domination.com thelandgeek learn anything about anything. Investor ninjas.com Scott Todd. How are you, Mark? I'm great. How are you? I am intimidated because I feel like I'm really going to screw up deray's last name, even though I've been practicing it for, like a minute. So our guest today is Deray Ola Leah.
Perfect. Perfect. There you go.
And if you don't know about Dre, he is a real estate entrepreneur and business coach. He mentors overwhelmed and unfulfilled employees in the professional world through the process of creating and building a lifestyle business through real estate investing, so they can escape the rat race and live a life of their design. Dre, welcome. How are you, Mark?
I'm doing amazing. I'm so happy to be on the show. I can't wait to perhaps add some value to your listeners.
Yeah. So let's just rewind the tape and talk about before you started making millions, which, by the way, is a pun because you do have the website before the millions.com and I was on that podcast. How did you become the lifestyle entrepreneur and real estate professional that you are today?
Yeah, I love it, Mark. And, you know, I want to take it back for you. But first and foremost, I do want to do want to touch on the fact that you said, I am a lifestyle entrepreneur, and that is indeed the case. But we are still before the millions, Mark. And the premise of before the millions is, is really walking through an individual's journey, whether it's my journey or a guest on the podcast similar to yours. Mark, your journey. You walk through your journey before the millions and getting to where they ultimately achieve their lifestyle design. And for me, lifestyle design has always been the number one goal. Right. I know that yet. And still there's so much more growth. There's so much things to be had. There's so much things to be done, but lifestyle design has always been the number one goal. So I created a plan back in college, or a little bit after college, as a disgruntled employee, a big four employee at an accounting firm. I created a plan to escape the rat race in about two years. And the only way I was able to do that, Mark, is by replacing my passive income, by replacing my active income with passive income. Okay? That was the only way I was able to do that. So oftentimes, I mean, I fast forward till today and I'm working with clients who are making 3, $400,000 a year and, and every single month they're broke. I have clients who are making 75 grand a year and they're living their ultimate lifestyle design. They're traveling the world, they're doing what they really want to do, and they're successful in their own eyes. And Napoleon Hill had a quote that success is the constant realization. Success is the constant progression of a worthy ideal. So success in everybody's eyes is very different. But for me and my tribe again, before the millions were really just predicated on that lifestyle design aspect. So again, that was always the goal for me. And I remember being a disgruntled employee working about 60, 70 hours a week at a big four accounting firm and I hated it. I absolutely hated it. And this woman, I call her my guardian angel, she gave me this little purple book. And as you know, that book changed my life and everybody's life really. But it got things in perspective for me. It made me buy my first investment property. Having no prior real estate experience as far as being an investor made me buy my first investment property in the next 30 days. And for some reason back then I didn't like, now I see it like with myself and with my clients, like I see, like, you need to be able to ready, fire, aim. Like, you need to be able to have the foresight to know that you're going to make mistakes. But back then, for some reason I kind of knew that. Most people know that real estate is a wealth generating vehicle. Most people know that. Most people have heard the quote, you know, 80% of millionaires have done so through real estate. And although all the quotes that are out there, most people can't conceptualize it for their own lives, so they don't really take the action. And I knew that if I were to take that action, Mark, whether or not I failed, that's why I did it so fast. I was like, dude, this is about to be the worst deal ever. I don't care because I've already made a decision. And when you decide on something, you know, the root word of decide is ide. And that literally means to kill off. So like pesticide or genocide. So when you make a decision, when you actually decide, there's no other option. So for me.
So what did you kill off then, when you decided?
I decided that I was 100% going to be a real estate entrepreneur. I was 100% going to be an investor. I never wanted to have a day job ever again in my life. That's what I decided to kill off.
So I didn't kill off the rat race.
Yeah, yeah, yeah. And I didn't care about the fact that it may be the worst deal ever. I knew that I was going to take that experience. I was going to take everything that I learned. I was going to take my connections, my resources, I was going to take all of that and propel that to a second good deal. So I went into it thinking it was going to be terrible. Mark, guess what? It wasn't bad. It was actually a really good deal. And that was all because I decided to get started. And I think that's the biggest message right now. I mean, just kind of opening this up. And I know you probably have a few questions. That's the biggest message right now. Just kind of from what I shared.
No, I love it. I love it. And let's just pick on Scott Todd, because he has a similar corporate background. And so, Scott, you probably weren't as intentional with the word decide as Dre, but what are your thoughts? What deray just said. You're on mute, by the way.
Sorry.
I think that the.
I think that the interesting thing is that one of the things that he said was that he decided that he was going to do a deal, right? Like, he decided he was going to go do this deal. It wasn't necessarily the best deal. He's like, I'm just going to go do it. I'm going to learn from it, okay? And that's a lot of times what we talk about. We talk about that quite often is too many times people, they don't take action because they want everything to be perfect, right? Like, there's no perfect. I don't have the time. I don't. You know, my family life isn't the best. This and that. Life is never perfect, okay? Like, you got to just take the action, go do it. And guess what? If you fail? Well, then guess what. You learned a lesson. Okay? It could be an expensive lesson, but you learn the lesson, and you're going to be okay. Oftentimes, the deal will turn out a lot better than what you actually think that it would. And then for that, you'll get more success. Success breeds More success.
Right.
And I think that's the, that's really the secret there.
So Jerry, that leads us to what was your first investment and what are you currently investing in now to build your wealth, to build your passive income?
Yeah, my first investment was a single family home was a three bedroom, two bath and it was $165,000. It was cash flowing about $250 a month when I closed on it. And immediately after that I started, I bought a few more single families and I started heading into the small multifamily space. So I bought a 4 Plex and I had a few life events such as being on the verge of being fired, which is what started this in the first place. That really changed my perspective on how fast needed to get out of the rat race because I got fired from my big four accounting job and only had a few rentals and I was just like, dude, like I don't have enough passive income. I started a businesses as well that same year. Rich dad, poor dad. I started eight businesses and they all failed. I didn't, I had never started a business in my life. I didn't know about the marketing cost that went into each business and the roi. And I was just like, dude, this is insane. So they all failed. So anyways, I talk about this oftentimes on my podcast in many places. But I was in a position where like things were hitting the fan. Like I got fired from my job, I only have a few rentals, all my businesses are failing. What's next? I remember it may have been enriched at poor dad. I remember a specific paragraph where he talked about, instead of going to pay, you know, 30, 40, 50 grand to a college in tuition, why don't you go work for a company that pays you that money to learn? Mind you, I've already graduated from college. I was working at a big four accounting firm. So I learned the accounting side of real estate. I learned how to look at things in arrears, but I didn't yet have the financial backing, the financial expertise to really be able to analyze deals at a high level. So my very next job after I got fired, I worked went to go work for a private equity hedge fund based out of New York, managing 26 billion in assets. And I was like, dude, like I'm working in funds, I'm printing investor reports. Like I'm right in the thick of things. My next transition after what just transpired is to go into the apartment space. So I went into the apartment space, got a mentor, lots of learning lessons, Lots of learning lessons. And again, I know we only have 20 minutes, and I would love to go through those, but lots of learning lessons. Ultimately, I came back out and realized that the niche, not only for me, but also the people that I train and coach, the niches, the small multis and the single family space, and really just going after creative financing deals. So, long story short, that's kind of where we kind of came back and ended up. And it's been a beautiful process knowing that if and when I get back in the apartment space, my motivation and my goal is to be a passive investor rather than a syndicator through the lessons that I learned.
I love it. Scott. Todd, what's your big takeaways?
Well, I mean, I think there's so many, right? Like, there's so many things, so many different ways we could take this thing is that, you know, I think that. Okay, first, Mark, just the thing that was on my mind. Rich dad, poor dad comes up again, right? Like the book that. We had talked about this on another podcast. Here's Rich Dad, Poor dad again with his. With his infinite wisdom. And I think that the reality is that a lot of times people, they struggle to. Again, they struggle to take action, right? Like, they're not happy where they are. For me, one of the things that I thought was really cool about my corporate job was all the stuff I got to learn, right? Like, that is one of the cool things that I like. And honestly, it's one of the things that I never really thought I would miss it, but, man, do I miss it. Like, larger companies, they do have access to state of the art training technology, right? Like, you have access to good training and you don't even realize, like, when your boss says, oh, you got to go to this training class, like, oh, no, not again. But now looking back, I'm like, man, I wish I could just go to one of those good, good training program. So leverage it, right? Like, while you're there, don't just look at that. You're there for the. For the paycheck. Figure out what you can learn about the place that you're at. Like, figure out what you can learn about the industry. Figure out what you can learn that you can take with you. And, man, that's going to make you just even more rock solid and bulletproof.
Yeah.
I love the way Dre leveraged the mentor to smart cut his growth and his learning curve as well. So, Dre, what advice would you give? Given all the life experience you've had and investing experience you've had, you know, let's just pick on that poor guy, the Procter and Gamble cubicle right now that wants to get out of the rat race. What would you say would be a really viable strategy to start thinking about your escape route?
Yeah, I love that. And I've been asked that question probably hundreds of times in the past three or four years. And last year, I finally decided. I was like, you know what, Mark? I need to create something where people can just run through an analysis of themselves, forget about what I do, forget about what Mark does, Forget about what BiggerPockets does and all our advancing strategies. Let's figure out what's possibly best for you as an individual. So I created an assessment, and it literally just asked seven questions to the individual. And those questions are questions like, what do you want real estate to provide in your life and why? And then by when? Right? Because I wanted to escape the right race in two years if I want. If I love my job and I wanted to stay there for the next 30, 40 years, I may invest in a very different fashion or manner than somebody who wants to escape the right race in two years. So ultimately, asking those types of questions will help you narrow down exactly where and how you should get started. Also, what's your experience? What's your education level? Again, I was working for a big four accounting firm. I worked to work for a private equity hedge fund. Can you. Do you have that same experience to jump into a similar space? And if not, how much time do you need? Right. If you want to be a developer, how much? What's the learning curve as opposed to what your goal is? So asking the question, asking the inward questions. Right. I think that many. We. We've saw through the test of time that all vehicles in real estate pretty much make money. There's a millionaire, if not dozens of millionaires in every single niche and every single vehicle. So take money out of the equation really quick. These vehicles make money, and they will work if you work it. Big emphasis on if you work it, they will work. Right? Eventually. But if you take money out of the equation and you put the onus on yourself and what you want and what you have and what your resources are, how much time you will then dedicate. Again, if you don't have a whole lot of time to dedicate, but you have some money to dedicate, you hate your job. Maybe invest passively in an apartment building. If you have a whole lot of time to dedicate and you're short on resources, maybe you go door knocking, Maybe you Try to do a few wholesales. Right. It's all dependent on your situation and your goals. If you could ask yourself some of those thought provoking questions, I think that'll help you get a better footing on how to get started in real estate.
Yeah, I love that answer, Scott. Todd, what are your thoughts?
Well, it is true some people have more time than money and some people have more money than time. So, like, figure out which one it is that fits you and then go out there and use it. Right. Like, if you have more time, well, then go find people that have more money, get the money that you need to do the deals that you want. Just do a deal, for Pete's sake.
Yeah, 100%.
Yeah. When I go on podcasts, I'm super arrogant about it. I'm not, as, you know, open minded about Dre, like, well, it just depends on you. I'm like, no, this is the best passive. Right?
That's what you should do at the same time. But I'm just like, everybody's circumstance is different. I'd love to everybody to kind of do creative financing like I do. I think that it's an amazing way to get in with none of your own money, none of your own credit. You don't have to work with a bank, you don't have to work with an investor. But at the same time, you have people who have money to put to use and they want to, you know, get a return on that. And, you know, so there's, there's different positions for everybody. But I totally agree. I am biased towards what I do 100%.
So you did bring up creative financing. So let's just define that for the listeners. And then what is your go to creative financing strategy as of today?
Yep. So I focus on two strategies. One is called owner financing or seller financing. And there's a few strategies that stem from that, like subject to. And then. So that's one strategy of actually taking down the property, and then the other strategy of not taking down the property but creating massive payouts for yourself is an assignment strategy. And I have two assignment strategies. One is a wholesale assignment strategy and the other is a tenant buyer assignment strategy. Both allow you to take down the property without any of your own funds. And depending on the condition of the property and the owner situation, you may try to pay half price for the arv or you might trade. You might be able to actually pay the going market rate. And that's a really neat thing that we're able to do with certain types of sellers and their Motivations. So those are the two strategies.
All right, Fantastic. Scott. Todd. Mark. Yeah. You have no thoughts on this?
Because what is our. What is our. I mean, he's talking my language, right? Like, owner. Owner financing. I mean, I know he's talking about, like, on the buy side, but, man, if I could owner finance our land that we're buying, jeez, that'd be a dream come true. And you can actually.
I mean, yeah, we. And we. Yeah, so we do employ that strategy. We just don't sort of use the term creative financing. We just say, this is how you finance.
Yeah, I mean, that's. That's. Mark, that's one of the cool things I think is about land, right? Like, we talked to a lot of people that are doing multifamily and stuff like that. And multifamily is sexy. I'm with you. Like, it's there, but, like, man, there.
Is definitely got more friends than us.
That's the thing. Like, but see that the whole deal here is that, like, what we do is so dang simple, right? Like, and I think it's simple, but it's. It takes work. It takes some work, right? And, like, what. What he's doing is a little bit more complex, but guess what? It takes work. The deals are bigger. The risks are bigger. You need, like, Mark, you and I both know, like, going to the bank and asking them for money to buy something is not any fun, right? Like, it is like pulling teeth. And I think that when I. When personally, when I hear these stories, like, you know, like, raising capital and, like, then I think about all this stuff. It's sexy, right? Like, it's flashy and I'm in. And then there's one thing that I think about. Go into the bank and tell them I want to buy this thing. And they take everything that you've done. They, like, rip it apart. Like Nancy Pelosi ripping through paper saying, no, no, no. And along the way, your credit's getting ripped up and everything, too. It just makes me sick. I'm like, I think I'll run back to land. Like, I gotta tell you, like, that's. That's where I really come back to land every time is all these other things look cool, but, man, just keep it simple, baby.
You know? You know, Mark was on the show, on my show, probably a little over a year ago, and I think about the fact that we've. We've produced over 140 episodes. And out of those episodes, I remember Mark's episode distinctively because it was a strategy that, you know, again, I hear all these strategies, and you guys probably do the same, but it was a strategy that was like, wow, this is. This is fascinating. This is interesting. Again, having already chosen my path, I already kind of stayed in my lane, but I always thought in the back of my head, like, what if? Or what would that look like? And recently, one of my clients, he started. He started a fantastic fashion finding leads on Facebook. He closed his first deal literally seven days after starting, and he got three leads, and one of his leads was a land deal. And he asked me, duray, what do I. What do I do with this? And I was just like, that's a good question. Like, so I have that question for you guys. Like, as an investor that knows nothing about land, when you come across a lead like that, because of the way that you're filtering for lease and because of the way. Because of the way that your funnel is built, should you get let go of that lead, should you recommend that lead, should you try to do a deal even though that's not your niche? What do you guys think? Especially when it comes to land taking over your podcast?
I just want question.
I'll tell you what I would do, right? Like, if I were him, if I were him, I would email me the lead and say, here you go. No, I'm just kidding. Like, I think, look, see, that's the problem, right? Like, there's the problem. Shiny object syndrome, okay? Like, you get something, it's not in your lane. You know, there's money there. So what do you do? A lot of times, people, they don't. They don't say no to it. Then they start exploring. Well, the next thing you know, he likes the land business. Okay, that's great. I want him to like the land business. But then at the same time, then he's half doing land and he's half doing the multifamily he's doing or whatever he's doing. He's half doing both things. He's doing none of it well. Okay? And now it's like, to me, and this is like a pet peeve that I have, is that I hear all the time, people say, oh, I'm a serial entrepreneur, man. I've got seven different companies going. Well, listen, man, you're not doing them well. Let's be honest with you, right? Like, you're not doing well. You know, like, do. Do one and then lay the track. Like, okay, like, you're doing this thing well, what can you do that. Parallels with it. That builds synergies. These Guys, I talk to people that are like, I'm doing this, I'm doing that over here. Like, you're not doing none of it well. So it's the same thing with real estate to me is like, if you're going to be a land investor, be the land investor. If you want to learn about land, but you're doing multifamily well, essentially, you're going to have to decide, like, which one are you going to do? Or you're going to have to be dedicated. Like, I've got teams over here that's running this thing now. I'm going to add in another revenue stream, but I'm not going to do it. I'm going to be the CEO. I'm going to get people to go do it.
Yeah, yeah.
Andre. I'll be honest, I rarely if ever agree with Scott, Todd, but on this point, I have 100% agree with. You want to. You want to be focused and you want. We're an inch wide but a mile deep. And I think when it comes to any investing strategy, just acknowledging this stuff, it might be simple. Like, our niche is simple, but nothing worth doing is easy. So added complexity is not going to make you any wealthier. If anything, it's, you know, splitting your attention is going to make you poorer in that sense. So, Scott, on a rare occasion, we should actually mark this. I agree with you.
We agree all the time. What are you talking about? You have me confused with Eric Peterson.
Eric Peterson I don't agree with. You know, when you get to my age, you just. It all blends and blurs.
So.
So, Deray, we're at that point now, the podcast, where we're going to ask you for another tip of the week. A website, a resource, a book, something else actionable for the art of passive income listeners to go improve their businesses and improve their lives. What do you got?
Hey, so I actually am going to recommend the resource that we talked about earlier when you asked about how do I get started in real estate, what vehicle do I choose? That resource is over at beforethemillions.com newbie n e w B I E. And it's not only a resource that gives you an assessment to fill out, but also you'll be able to listen to different podcast episodes based on the niches that you're interested in. Or one of the podcast episodes in the newbies guide is actually my episode with Mark specifically talking about land. So again, if you're interested in land, you will see that as an option there and you'll Be able to decide and decipher if that is a viable option for you. That's over at before the millions.com n e w b I e. Thanks, Mark.
All right, Fantastic. I love it. Scott Todd, what's your tip of the week?
Hey, Mark, what if you had. What if you had the ability to, like, wherever you walked around, you could have, like a megaphone in your hand, like, attention you need to invest in land. Like, that'd be pretty cool, right?
I might be one of the more obnoxious people in Scottsdale with that thing.
Listen, I'm gonna give you a modern day. I'm gonna give you a modern day mega megaphone. And it's this app, and the app is called you Louder. And it's like, I don't know if it's available on itunes or on Google, but it's definitely available in the app Store on Apple App Store. What's cool is you download this app and it connects with other people, other users nearby, and you could be like, hey, I lost my dog, or, hey, you know, you should invest in land. And it sends it out to their phones and it sends it out to their Apple watches. I mean, I can see annoyance city coming, man.
You Louder. Am I really gonna download this right now? Right? Look, man, are you gonna download this thing?
Don't you just want to go out there and, like, break it and convince them that this is a bad idea to the world by just turning this into the latest, greatest marketing platform?
I'm strongly not considering it, man. I'm strongly not considering Duke. Louder. It sounds like, oh, my goodness.
Is it really.
Is it really taking off?
I'm talking about it.
I don't know. It's. You know what? I might use this for my kids. Did you clean your room?
Oh, that's the trash out. That would annoy them.
Yeah.
Well, imagine if you could do it through video, though. Like, imagine, like clean your room and it goes right to them.
That would be good. My tip of the week is, you know, not as good as Scott's, but probably as good to raise before the millions dot com. Check out the podcast. Learn more. Certainly check out beforethemillions dot com newbie. I do want to thank all the listeners. I want to remind you that today's podcast is sponsored by flight school. Just go to landgeek.com training to learn more about how 16 weeks can literally transform your life. Start building that passive income and have Scott Todd as your Sherpa up the mountain of land investing. Also, please, dear listener, if you're getting value from the podcast. Do us three little favors. Subscribe, rate, review the podcast. Send us a screenshot of the review to supportlandgeek.com we're going to send you for free the $97 passive income launch kit course, as well as the latest course, how to double your money 30 days or less in wholetailing. All right, Scott, you ready?
I'm ready.
One, two, three. Let freedom ring. Not bad. Dre's like, I know they're gonna end like that. Maybe I should have come on the podcast.
I like that. That is awesome, Dre.
Thanks so much. And thanks for helping me with pronouncing Ola le. Yay.
Oh, we got it. Even better.
Oh, cocky. There you go.
I love it. Thanks for having me on. It's been a pleasure.
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