From Broke to $20M: Real Estate & Podcasting with Wyatt Simon

Getting sent home from work for forgetting a belt sounds petty until you realize what it represents: a life run by rules you didn’t write. That moment helped push real estate investor Wyatt Simon away from the corporate path and toward building assets, cash flow, and the kind of freedom most people only talk about.

We dig into how Wyatt went from broke to owning and operating a $20M+ vertically integrated real estate portfolio, and why the BRRRR strategy (Buy, Rehab, Rent, Refinance, Repeat) can be a practical on-ramp for investors who want to scale without waiting forever. He shares the unfiltered side of real estate investing too: deals that drag on, rehab budgets that blow up, and the painful lessons that become expensive when you try to learn everything alone.

A big theme is the “learning tax” and how coaching can shorten the curve in real estate, business, and even podcasting. Wyatt breaks down how documenting his journey on social media led to consistent inbound questions, and how he turned that demand into a coaching program that helps students take action faster. We also talk podcast guesting as a modern communication strategy, including what makes a show worth your time, why specialists beat overloaded general VAs, and the red flags that signal a low-quality interview.

If you’re trying to build wealth, grow a real estate portfolio, or use podcast guesting to expand your brand, you’ll leave with a clear framework: build a cash machine, then invest into cash flowing assets. Subscribe, share this with someone who needs a smarter path, and leave a review with your biggest takeaway.

Connect with Wyatt

LinkedIn: https://www.linkedin.com/in/wyatt-simon/
Website: https://wyattsimon.com/
Book: https://www.amazon.com/Your-First-100-Units-Investors-ebook/dp/B0D9SQKGFK

Transcript

Welcome And Show Format

Carl 0:04

Welcome to Communication Connection Community, the Podcasters Podcast. This podcast takes a deep dive into modern-day communication strategies in the podcasting space. We chat with interesting people who make the podcasting and speaking spaces exciting and vibrant. We also dive into the podcasting community with news, updates, latest trends and topics from this ever-evolving space. Let's dive into today's episode. You know, for most of us, we go to school, we get an education, we get a job, and we think we're going to stick in that job, and that's going to be our career and live happily ever after. Does it ever really happen that way, though? Our guest today is a washed-up basketball player, turned investor. Yes, Wyatt Simon owns and operates a $20 million plus vertically integrated real estate portfolio, and he's mastered the burst strategy, why it helps folks ditch their nine to five jobs and transition to multifamily freedom. He's a member of the City Light Church and the author of Zero to 100: a real estate investor's guide to scaling a rental portfolio. He is also a sought-after podcast guest, and we are so glad to be speaking with him today about his journey, not only into real estate and into business and also into coaching, but into podcasting as well. Wyatt, welcome to the podcast.

Wyatt 1:34

Carl, thanks for having me on, man. Excited to be here.

Carl 1:36

I am so thrilled you're here. I know a little tiny bit about real estate, but I would love to learn a few things from somebody who certainly has lived in it. And full disclosure, you just hit a milestone birthday. Is it okay if we say that? I'm old. You can say it. Is it okay if we say you're 30?

Wyatt 1:56

Feels strange. I worked hard in the 20s, man. And so it feels like a turn of a milestone. Kind of starting to slow down a little bit and enjoy some fruits.

Corporate Misery And The Belt Story

Carl 2:05

Slow down in your 30s. It's funny because as a broadcaster, turned podcast coach and trainer and running an agency, I think my career as a broadcaster was just ramping up my 30s. And here you are going, starting to wind down, chill out, sit on the beach. Kudos to having painted or created a path to freedom for yourself. Let's talk about that though, because I think for a lot of individuals, when they come to the podcasting space, they think that this is going to be the vehicle or the tool that makes them an instant success overnight. And you know what? That rarely happens. Of all the things you could have done in your 20s, what led you to real estate? And was it actually in your 20s, or did this happen sooner?

Rich Dad Poor Dad And Early Moves

Wyatt 2:45

We'll start with why real estate was interning. So I played college basketball at a super small college called Done. That's where uh 5'11 white guys play basketball, just so you know. They gave me a scholarship and I went to the middle of nowhere in Nebraska and played ball there. But anyways, while I was working there, I was interning at a place where I had to drive 45 minutes, wear a full suit and tie to work. And I talked on the phone to farmers, selling them ads. And we sat in rows and your manager sat behind you, and it was just like straight out of the 60s, just bureaucratic and I hated corporate. I just hated sitting in that desk feeling like I was wasting my life away, being forced to wear a full suit and tie for no reason. And there was one time where I actually, my boss tapped me on the shoulder and said, Wyatt, we need to talk. Like, oh no. She takes me to the back room and she says, Where's your belt? I looked down, I forgot my belt. And she sent me home that day because I wasn't wearing a belt. And that was just one experience of many that just made me know I didn't want to work in corporate the rest of my life. Because of that, I read a little book, Rich Dad, Poor Dad. I don't know if are you, have you read that book?

Carl 3:49

I haven't read it, but I'm very familiar with it. Yep.

Wyatt 3:52

So after reading the Purple Bible, as they call it, it talked about how assets can make money for you while you sleep, so you don't have to work for money. And that was a light bulb moment for me. I gravitated, I wanted to do that, but the problem was I didn't have any money. I was totally broke. And so I was like, okay, how do I buy real estate without hardly any money and scale a portfolio? And so after learning like stuff like we talked about in the BRRRR strategy, it's allowed me to start to scale a portfolio. And from there, now I don't have to wear a full suit and tie, but shirt, doing this interview.

Coaching Through Documenting The Journey

Carl 4:24

And you don't have to wear a belt if you don't want to either. Which is it's funny that you mentioned that because when I was in high school and my first bit of college, I worked in a fast food restaurant and we provided our own uniform pants. Most places now they provide the whole uniform. So we had to provide our own uniform pants, and they had to be navy blue, and you needed to have a belt. And same thing. If you didn't have a belt, you were sent home. And in some cases, it's like sent home, go get your belt, come back on shift, work punch out. So it was crazy that we, you know, there was a world that we lived in back then and not too far back for you, where it's like, oh my goodness, you don't have a belt. And it's like you've committed a crime that is punishable only by going home. You know what I mean? Clearly made a huge impact in a way that has led to where you are today, which is not only being very successful in your own journey as an investor, but you're also helping individuals in a coaching space become more successful in the real estate space. How did the coaching piece come into play? Is it just through the matter of already doing it? You want to help other people?

Wyatt 5:31

Great question. So, I mean, as I grew a rental portfolio, one of the best things that someone ever told me, I was at a mastermind maybe five years ago at this point, and I was very early in my journey, but I was at a mastermind and they said, Hey, everything that you do, just post it on social media, just post something showing like the action you're taking, documenting your journey. And so when I would go offer on a house or when I'd go fix up a house, you know, the before and after pictures, stuff like that. I wasn't doing a ton of volume. I did two properties my first year, three properties my second year, six properties my third year. And then I did 25 properties the year after that. It just started to scale. So I had post a little bit. People had gotten to know me as the guy that was doing real estate on the side. And eventually, you know, I started posting when I started doing 25 deals a year plus, people started to see it and I would do monthly recaps, and that brand presence started to grow. And so then everyone to answer your question, it's like everyone started asking me, Hey, how are you doing this? How are you doing this? And so eventually it was like, okay, I can't get, I physically can't go to this many coffees. It's just not gonna work. And so I was like, okay, how do I help people in a broad aspect by creating something that can answer all these questions that I keep getting? And that was why I created the coaching program. Since then, we've got 22 students have bought over $8 million worth of real estate. It's awesome helping other folks build their portfolio and get freedom for their family, like security.

Carl 6:53

I think that's the big thing is when you're helping other people and they can, it's not just about saying, hey, do this, it's helping them and being the guide. But you're right, you can't do 25 coffees in a week and expect that's going to allow you to, you know, not be tired and probably floating from having too much coffee, you know, too many coffees, just can't do it. And congratulations for doing that too, because not the coffees, but the coaching. Because I learned a long time ago that, and it doesn't matter what business you're in, it also doesn't matter if you're a podcast host or podcast guest, hosting for sure, and having a podcast, you should have a coach or some type guidance system that's helping you through the process because, and I'll speak from the podcasting perspective, but I'm assuming it's very similar in real estate. There's a right way, and there may be more than one right way to get to the end result. And then there's maybe a way that takes a little bit longer and maybe is riddled with a bunch of mistakes that you can avoid if you just have the right coaching and training and system or patterns that help you to get to that result or that level of success.

Wyatt 7:59

Absolutely. I call it the Learning Tax. The learning tax is gonna be there, whether you like it or not. And on everything, everything in life, it's got an exponential curve once you learn it. But that learning tax is right up front where you feel like you're making no progress, and a lot of people quit in that learning tax or they run into hurdles, like you said, and then they quit. You can get through it on your own and struggle. Like for real estate, for me, it was my third deal. I went 11 months, it was supposed to be two months. I went 11 months, it was supposed to be $20,000 a rehab, it was 68. It was just like I did all the mistakes you can imagine. And eventually I made it through. But then I got into multifamily and I couldn't afford to have the 3x oopsies in the multifamily space when the zeros were bigger. And so, what did I do? I hired a coach, I hired a consultant. I've spent over 150,000 just on private consulting to help me build the portfolio that I did to shorten that curve. And so what I've learned is you can pay for it one of two ways, the hard way or the consulting way. And I will that the rich pay down their learning curve and shorten their time by paying for it.

Carl 9:04

I could not agree more. And I think we've all been in that space where we've made mistakes along the way. I know I did. I remember when I started my business, I was a part-time business doing speaker training. And I thought second year, I'm going to be, and again, I was really low numbers and really limited beliefs as in how I could grow a business. But I thought, you know what? I'm going to have this many coaching sessions and I'm going to make $50,000 to $75,000 a year, too, as a coach without a coach. It's just basically saying, I'm a speaker trainer. I know what I'm doing. I can speak. I'm in radio. I'm in Toastmasters. I know how to do all this stuff. What do I need a coach for? Rude Awakening, basically. As I'm sure that you and maybe some of your students even have said, you know what? I didn't realize that I could have saved myself a lot of headache by getting the coaching and training. It's not even the coaching and training, it's the guidance. It's the "You want to shorten this? I can show you how to shorten it." And I think we share a brain when it comes to that, being able to shorten the cycle. I've chatted with people who have this goal about wanting to be a podcaster and they've been thinking about it for two years. They finally launch a show, they launch with seven episodes and they think that that's all they need to do. And why aren't they a huge success? Not realizing that an overnight success usually takes a little bit longer, number one. But number two is if you want to shorten that cycle, it is the coaching, it is the training, it's also the connections that you're making along the way. It's the right information. And I'm assuming in the real estate space, too, when you're talking about investing, there are many ways to do it. And sometimes we don't understand the easiest way to do it or the most efficient way to do it.

Wyatt 10:42

Absolutely. And it compounds. Like the sooner you can shorten that, the sooner you get to the exponential route. Where, like initially for me, it took me 11 months to flip a house to lose money on it. That was fun. But that's 11 months of my life that I helped save my student, my first student, or not my first student, but one of the students recently, he just a month ago, he bought his, he just sold his first house. For me, it took me six months to find my first house. It took me another 11 months to complete the rehab. And then I lost 40,000 on it. For him, he took he paid mid-school amount of coaching. And within his first three months, he bought a house. Within the next three months, he rehabbed it and sold it. And he made $48,000 on that house and paid me a fraction of that. He made over $40,000 with a coach in six months. I lost $40,000 in 11 months plus six months. So 17 months. And now he can repeat this, right? He can do this again and again and again because now he knows how to do it. So that's the power of it.

Why Podcast Guesting Builds Awareness

Carl 11:46

That rinse and repeat, I think, is very important as in the coaching system. I have a coach who says, "I want to do this, do this, do this, rinse and repeat." Five-step or six-step, even seven-step process that it's just repeat this. You know what? There might be tweaks along the way. Education is always going to be a learning process. That's why they call it education. But what you know today could change a year from now. And it can be based on the economy, it could be based on regulation, it can be based on, I mean, if we were having this discussion back in 08 when there was a housing crisis, it would have been a completely different conversation. And if we had this conversation pre-COVID, it would have been a completely different conversation. It's interesting how they and things change, things evolve, mortgage rules, lending rules, everything evolves. And staying on top of that and being able to be that help, I was gonna say hope, but hope too, and also help for individuals who definitely need it. Let's talk about the podcast because you've come into this podcasting space. And what was it that led you, of all the things you could do to evangelize what you do? Why did you choose a podcast or podcasting in general as a guest?

Wyatt 12:50

Well, I knew I had to bring awareness. I can't help anyone if no one knows who I am. The podcast space in general, I use as a platform to get in front of people so I can help them. Like I spoke at an event for 100 people, and that it was so easy to help people when you're in an event room. And I said, okay, I don't want to travel across the nation doing events. But now on podcasts, on social media, on just videos in general, you know, you're getting thousands of views every single day. That's bigger than an event, you know, for 100 people. And I thought an event for 100 people was pretty cool, right? But it's it's not even comparable. You know, I'm 10Xing that. And so the podcast platform was a really cool way for people to get to know me that maybe don't know me. And then they can start to see, "Hey, can I help you? Or hey, can I just help someone without even monetizing it?" Like, can you learn from my mistakes and apply it to the podcast space with you or other learning curves that you can shorten it?

Carl 13:42

I think the nice thing too about leveraging this platform is you're building relationships that you didn't know about before. Like you say, you can go to events, but be they real estate focused or business focused or whatever, and be a speaker or be an attendee. And to your point, do you want to do that 52 times a year or more?

Wyatt 14:02

Trying to slow down, Carl.

Carl 14:04

Well, you know, now that you're 30, you have to slow down. You really do. But seriously, do you want to do that at this point in your life and your business and your you know career where you've taken it? Probably not. And we're in a time now where your generation, if I can say that, and I say this with a bunch of respect, they're not looking to travel coast to coast and attend these events. So how are you going to reach them? Radio and television, though they're not dead, they're struggling. So a podcast makes sense, be it audio, video, both. I mean, you're still making those connections that you wouldn't necessarily have. Let me ask you this though, because you've been at this for coming up on a year. How's the journey been for you? Have you found that it's been a great success? And I do have another follow-up question after that, but but how's the podcasting journey been for you up to this point?

Wyatt 14:51

Full disclosure, I've been a guest only, guest only as I've gone through this to grow the brand a bit. And as I've been growing the brand, it's been like everything. You go through ups and downs, like inconsistency, because I do have other businesses that are my main sources of income. This is kind of a side deal. It's been inconsistent as I've appeared on podcast guests, and then as I've built the systems behind the scenes for our editing team to take this and run with it, and our VAs to reach out and actually connect and schedule podcasts that are worth the time to be on, like this one. There's ups and downs. I've definitely been inconsistent, but I'm excited as we build it, like everything to get there faster.

Systems And Specialists For Guesting

Carl 15:29

Any aha moments that you've discovered along the way that maybe you didn't realize coming in as a podcast guest?

Wyatt 15:36

So one thing, yeah, one thing is I have overloaded my VA to be more of a generalist than work with an agency or a coaching platform or a podcast guest platform that is a specialist. I looking back, I would have done it different. I would have just hired a specialist that can chop up content and get podcast guesting and have a coach that just knows where to be, when to be. That would have been the smarter move than me taking my VA that had very little video editing experience, teaching him the ropes and going through all of that. But that was the longer, the longer way to do it.

Bad Podcast Fits And Red Flags

Carl 16:10

I do think, too, and to that point, now you're looking at this from a guesting perspective, but even if I can just but parallel this too, there are a lot of hosts out there that will do the same thing. They'll leverage a VA or an assistant that isn't the agency. It's not, they're not the professional. They don't have that. I mean, again, not toot my own horn, but 25 years in radio broadcasting, I know what sounds good. And I also know from a content creator and specialist, I know what looks good and I know what doesn't look good. And having those eyes and ears on it makes a huge difference. It's kind of like, I don't know about you, but I was a music student when I was younger. And I thought when I was, not that I went far with piano, but when I was playing piano, I'd play piano, play piano. I'm thinking it's perfect. And then my music teacher, my piano teacher, which she wouldn't rip it apart, but she'd say, "It was good. But what about this? Just to make it sound more melodic and with dynamics." And it's like, okay, well, that's something that the average individual isn't going to catch. Or they need the they again, they need the training, they need the coaching, they need all of that to just like what you're doing in your real in the real estate space to do that. So good point with that. But certainly I'm glad it's working for you. I'll ask you this question: any horror stories that you want to share or something that crept up that you weren't quite sure if you were going to recover from it. And again, it's podcasting, it's meant to be fun, but any, and again, not to tell tales out of school. And if not, that's fine. But any that you go, "I wasn't expecting that from a show." And if I hope it's not this one, by the way, but anything, anything that made you go, huh, be aware of that next time.

Wyatt 17:44

I will say there was a show that it was just a giant pitch for me to join their whatever. And so, and thick accent, very difficult to understand, and their background had like TVs that were just running digital ads in the background the entire time for like their stuff. Not only was it very difficult to even get through the interview because they barely spoke English, but then it was just a giant waste of time. Those were kind of some of the struggles. And then from there, we have tweaked what we what I will appear on and what I won't.

What’s Next For The Business

Carl 18:18

Lesson learned on that one. I can't say I've seen that one. I've seen people use branding monitors for obvious reasons, but not as a as a ticker tape saying, and we got another one now, and not turning it into a pit. Kudos for you for recognizing that. From a business perspective or even from a podcasting perspective, whichever you want to speak on, and feel free to speak on both if you wish. What's laying ahead for you? What's laying ahead for Wyatt over the next, let's say, let's say two years?

Wyatt 18:46

I'm really excited about where we're going. I have we're pacing for seven figures. So for the first time in my life, I've built a company that is going to produce seven figures next year. That's our wholesaling business. And so one of the biggest unlocks, again, I've got a coach that's helping me with this. One of the biggest unlocks is when you hire an A player and they can just take over and they can start generating revenue. So we're really excited to pair what I'm doing with another A player that's going to come on our team. And it's not like I haven't done that. Like I have eight full-time employees, the property management company is running by itself, you know, managing $20 million worth of real estate. But I'm really, there's no like that's all reoccurring revenue. So it's just there's no sales guy built into that. I've always been the sales piece. Once I hire out the sales piece in the wholesaling business, now it's just like at that point, I really am not doing too much anymore. And I'm excited for that. Where we're going with it is we're going to have two key people in each position. So that way we don't have to wait on just one person quits or doesn't work out. Now we're going to have two people in each position. Excited for where the world's going to be on that front. And then in the meantime, for the podcasting, just going to continue to guest appear on people's shows and just teach what I'm learning and uh share any kind of value I can have. If people want to build a portfolio and grow a brand, I mean, there's no better way than real estate and podcasts.

Where To Find Wyatt And Closing

Carl 20:05

And I couldn't agree more, my friend. Congratulations on the success up to this point and where things are going. And I certainly encourage you to keep guesting on those shows and building that brand. And again, congratulations on taking podcasting on with energy and excitement. Stick with it. I think you'll get a great deal of use out of it. And I think you're obviously enjoying it or else you wouldn't still be doing it. So, how can people connect with you though? What's the best way for people to learn more or get in touch with Wyatt?

Wyatt 20:37

Yeah, so the best way depends. If you just want to just hear more about me and see more of my story, go to Facebook. Follow me on Facebook, Facebook Wyatt Simon, W-Y-A-T-T-S-I-M-O-N. If you want free resources and you're like, hey, "I actually want to invest in real estate", then go to my website, www.wyattsimon.com. I've got a ton of free resources and guides on there. You can also join my newsletter where I will add value to your inbox for free every single Thursday morning.

Carl 21:05

Thank you so much for your generosity. And we'll make sure that those links are shared in the show notes so you can connect with Wyatt. I will connect with you too, Wyatt, so we can continue to build out our relationship. So thank you so much. Before I let you go, though, I'll give you the final thought.

Wyatt 21:19

I'll give you this. If you're sitting here and you're like, man, financially I'm not where I want to be, here's the framework to get there. You got to create your cash machine and then invest it in some kind of passive generating thing like real estate. Create the cash machine that could be a high-paying job or a business and then invest it in real estate. That's how to win at life.

Carl 21:39

Wyatt Simon, thank you so much for being my guest today.

Wyatt 21:42

Yep, thanks for having me.

Carl 21:43

And hey, thank you for being a part of the show today. So glad you could join us. Believe it or not, I can't work this magic by myself. So thanks to my amazing team, our audio engineer Dom Carillo, our sonic writing genius Kenton Dobrowolski, and the person who works the arms. All of our arms, actually. Our project manager and my trusty assistant Julovell Tiongco, known to us here simply as July. If you like what you heard today, let us know. You can leave us a comment or review or even send us a voice note. And if you really liked it, we hope you'll share it with your friends and your colleagues. If you don't like what you heard today, well, please feel free to share it with your enemies. And if you know of someone who would make a great guest on the show, let us know about it. You can get in touch with us by going to our show notes where all of our connection points are there, including the links to our website, LinkedIn, and Facebook as well. And if you're ready to be a guest on podcasts or even start your own show, let's have a conversation. We'll show you the simplest way to get into the podcasting space and rock it. Because, after all, we're Podcast Solutions Made simple. Catch you again next time.