Lessons in Building Wealth with Sean Kelly – EP 202

Interview with Sean Kelly

Brian Preston

Lessons in Building Wealth with Sean Kelly

Today’s guest is Sean Kelly, an entrepreneur and founder and host of the Digital Social Hour, a podcast with 11 million followers.

In our conversation, Sean takes us through his rise to becoming a millionaire by the age of 24. He gives us a behind-the-scenes look at how he struck gold during the NFT craze, including the jaw-dropping moment he pulled in $2.4 million in just 18 minutes on a single deal.

But it’s not all smooth sailing. Sean opens up about the highs and lows of building wealth. He shares some hard-hitting stories about how the market crash in crypto nearly wiped him out and how that experience reshaped his approach to diversification, including the different asset classes he’s now focusing on to hedge his bets.

In this episode, you’ll learn:

✅ Sean’s story of earning $2.4 million in just 18 minutes during the NFT boom and selling his agency for $2.5 million at 60% profit margins.

✅ The importance of knowing your financial freedom number – the amount of money you need to live comfortably without financial worry and how to use this crucial calculation to build the lifestyle you want.

✅ How the ultra-wealthy diversify their investments across different asset classes, like real estate, stocks, and crypto, to protect their wealth and weather market fluctuations.

Featured on This Episode: Sean Kelly

✅ What he does: Sean Kelly is the host of the Digital Social Hour Podcast, known for its focus on self-development, that has 11 million followers. He is also the founder of JerseyChamps and has been involved in ventures like Environment and chibi.dinos. Sean’s podcast has ranked as the top podcast in the self-improvement category. He brings entrepreneurial insights and motivational content to his audience, reflecting his commitment to personal growth and business success.

💬 Words of wisdom: “I know a lot of people say they’re millionaires, but liquid millionaire in the bank after taxes, that’s what I consider a millionaire. So, that happened at 24, which is younger than average. And I really had to change my friend circles. I had to cut a lot of friends. And that’s the part people don’t talk about.” – Sean Kelly

🔎 Where to find Sean Kelly: Instagram | X | LinkedIn

Key Takeaways with Sean Kelly

  • Your circle of influence
  • Making $2.4 million in 18 minutes
  • Lessons from losing money
  • How to diversify like the ultra-wealthy
  • Discovering your financial freedom number
  • The patience required for masterminds

Inspiring Quotes

Some people join masterminds and they get pissed because there’s no immediate ROI. So, when I spent that money, I didn’t make it back for like two years, but I knew that the connections I would make there, I would eventually make it back. And now I made it back tenfold because I still work with some of the guys there that I met.” – Sean Kelly

Don’t Tip Uncle Sam When Selling a Business

Resources

Tax Strategy Masterclass

If you’re interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax

Strategy Session 

For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation

The Lifestyle Investor Insider

Join The Lifestyle Investor Insider, our brand new AI – curated newsletter – FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider

Rate & Review The Lifestyle Investor Podcast

If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, Stitcher, Castbox, Google Podcasts, iHeart Radio, or wherever you listen, so future episodes are automatically downloaded directly to your device.

You can also help by providing an honest rating & review over on Apple Podcasts. Reviews go a long way in helping us build awareness so that we can impact even more people. THANK YOU!

Connect with Justin Donald

Get the Lifestyle Investor Book!

To get access to The Lifestyle Investor: The 10 Commandments of Cashflow Investing for Passive Income and Financial Freedom visit JustinDonald.com/book

Read the Full Transcript with Sean Kelly

Justin Donald: What's up, Sean? Good to have you here.

Sean Kelly: Good to be here in Austin, in your hometown, man.

Justin Donald: Yeah. Hometown, home studio. I love that you're here. I love that you recorded a couple of days here in Austin. I know we talked about me coming to Vegas but this worked out great.

Sean Kelly: Yeah. I'm glad I came and I got to meet the people around here, got to experience the culture, and it was great.

Justin Donald: You know a lot of people. I was blown away with how many people are on your list that quick when you set up a couple of days here. You know some big hitters.

Sean Kelly: Yeah. Ten people in two days and 850 episodes in a year and a half.

Justin Donald: Wow. For those of you that are not familiar, Digital Social Hour is one of the top-rated, top downloaded podcast, period, out of all podcasts. Where do you rank now? I mean, I know it's always ever-changing, but.

Sean Kelly: Yeah. It changes daily on Apple Podcasts or anywhere from number 1 to 5 in our category. And then overall, anywhere from I think our highest has been 75th. And right now, we're like 140.

Justin Donald: Okay. And what's your category that you're always a leader in?

Sean Kelly: Self-development but we started off as marketing because that was my main goal with the podcast at first. But honestly, I got bored of just talking money. That's just one part of life.

Justin Donald: So, give me an idea of like what it was in marketing that you uncovered or like why you felt like that was a great niche to start in.

Sean Kelly: That's how I made my money. So, I sold my marketing agency in the crypto space and that's what I knew, and that's what I was comfortable talking about. But after 100 episodes of marketing, I mean, I only talked so much marketing before I start to hear the same story over and over. And from there, I dived into other topics which I find interesting.

Justin Donald: Yeah. That's really fun. So, you sold a company. And by the way, I would like to point out, you became a millionaire at age 24. You're only 27 right now, a multimillionaire. Really impressive. I'd love to hear a little bit more about that.

Sean Kelly: Yeah. I'm in between millionaire and decamillionaire. So, next goal is decamillionaire and then centimillionaire hopefully in my 30s. So, that's my financial goals. But yeah, millionaire at 24 liquid. I know a lot of people say they're millionaires because their business does revenue but liquid millionaire in the bank after taxes, that's what I consider a millionaire. So, that happened at 24, which is younger than average. And I really had to change my friend circles. So, I hang out with a lot of older people and how to cut a lot of friends. And that's the part people don't talk about.

Justin Donald: Yeah. And when you say that, it's not that they're bad people but, in a certain sense, I feel like I've experienced this. I'm still friends with a ton of people I was friends with way back when but I had also friends that I found their influence pulled me down more than lifted me up.

Sean Kelly: Yeah. And it's not intentional on there. And that's the sad part. Through your friends you grew up with and that's great but at a certain point, if you're hanging out with them all day and subconsciously you're picking up on their tendencies.

Justin Donald: That's right. Jim Rohn always says that you're the sum of the five people you spend the most time with. And so, be intentional with who you're spending time with. Like, are you spending time with people that are playing the game of business and life and wealth creation at a higher level that have values that you embody that you're aligned with but you can learn from, right?

Sean Kelly: Absolutely. And when I came to Austin, you and Brad Weimert were the two I spent the most time with this trip, and that was intentional.

Justin Donald: Well, I'm so glad that you're here and we've got a chance to hear the first part of your story. So, really impressive that you became a millionaire so young. You know, for me, I always tell people my story is interesting because before I was ever a millionaire, I was financially free. So, millionaire came later. Financial freedom was first. I had covered all my expenses with passive income so I didn't have to work. I bought my time back, I owned it, and then only after that when I had surplus income and I started investing that into other deals, other things, did I become a millionaire. And so, I had a different path than most. And most people think that in order to be really wealthy, you have to be a millionaire.

No. In order to be really wealthy, you have to own your time. Being rich is having a lot of money. Being wealthy is having a lot of time or owning it, controlling it. And I think that's an important distinction.

Sean Kelly: Agreed. And also, being a millionaire doesn't hold the same value it did when you were my age.

Justin Donald: That's right. That's right. We got some inflation. I mean, I don't want to take away anything from a 24-year-old becoming a millionaire though. So, I mean that's big time to me. You made another point that I thought is a very important point, which is you had $1 million liquid in the bank, meaning your true net worth and I know you just bought your first home here two days ago, which is really exciting, or three days ago now, right?

Sean Kelly: Yeah. I think we closed on Tuesday. I don’t even know.

Justin Donald: So cool. I mean, I love it. So, two days ago. That's so awesome. Now, net worth is going to be your assets minus your liabilities equals your net worth. And for most people, they over-inflate their net worth. Like, my experience has been when someone says, "Oh, my net worth is whatever it is,” it's always higher than it really is. They're not factoring in the liabilities. They're not factoring in the debt on their company or they're overinflating the value of their company or something. So, I like the simplicity of yours. You're like, "No. Money in the bank. I'm a millionaire because I got a million plus dollars. It's liquid.” So, that's true millionaire.

Sean Kelly: Yeah. Money in the bank, crypto, maybe real estate. You could count it depending on how complicated it's structured but, yeah, I don't like when you count the business equity because not a lot of businesses are liquid. You can't really sell a business easily overnight.

Justin Donald: That's right. And most people inflate it so much that it's just not real. So, if you were to sell your business, someone else wouldn't pay for what you think most people think it's worth, you know? So, that's the greater indicator. And so, for me, anytime someone says, and remember in Lifestyle Investor, everyone has to really disclose a lot of their financial information to be able to get in because we have to vet to make sure that someone is the right fit. And also, that financially it's a good move. Like, we have people that would come in and pay 55K to be part of our mastermind that financially have no business doing it. They should not be doing that.

And so, we have to be able to say, "No, timing is not right now. Maybe later.” So, we do need this. So, when someone applies, it's a deep dive and we have people say, "Hey, I've never shared so much of my personal financial information before.”

Sean Kelly: Yeah. Their own wife probably doesn't even know.

Justin Donald: That's right. In many cases, I mean, that's what people say. Like, they've never shared this with anyone. I'm always, number one, shocked and surprised but, number two, I'm like, "Oh, wow.” Well, I'm glad I could bring you into this space where you're able to do it because how on earth are you going to be able to make it to the next level if you can't talk about it, or if you're choosing not to talk about it, if it's too taboo of a topic to talk about?

Sean Kelly: A lot of families operate that way. It's like a shameful topic. Yeah. It's unfortunate.

Justin Donald: Well, money should not be taboo. Wealth creation should not be taboo. We need to learn about it. We need to be around others that are doing it. And we need to be good stewards of our wealth and teaching other people how to do it, right, like passing it forward. So, whenever someone puts their net worth in my head like I've joked about this before on the show but in my head I'm like, "Okay. It's 50% or whatever you said.”

Sean Kelly: Yeah, divide it by two.

Justin Donald: That's it. I mean, to me, I think that's probably as accurate as you're going to get. Maybe some people inflate it more, but that's my number. And by the way, some people maybe they're real exactly what it is but I never trust that. Liquid in the bank, that's different. You can see it. So, talk through the sale. At any point, did you think maybe I shouldn't sell? Or were you just gung ho the moment you knew that you had the opportunity to be a millionaire to net a million on a transaction were you like, "All right. Let's do it because I can reinvent myself and do something else”?

Sean Kelly: Dude, it was a crazy year. So, what happened was I call it the beginning of the NFT hype. Do you remember this year?

Justin Donald: Oh, yeah.

Sean Kelly: So, I launched my own, which was before I started the agency. That did 2.4 million in 18 minutes, and half of that was net profit to me. And then I started that agency probably a couple of months after that and in six months we did $1 million.

Justin Donald: Wow.

Sean Kelly: With insane margins. It was like something crazy, maybe 60% margin. And then we sold that company in six months.

Justin Donald: And are you willing to share the sales price?

Sean Kelly: Yeah. I think I've said at 2.5 million.

Justin Donald: Okay. So, congratulations, first and foremost. From a taxable standpoint, was there anything you could do to mitigate those taxes, or did you just have to pay a big chunk?

Sean Kelly: No. And that's why I talk to you at the mastermind about this. I paid it all in full. I have no strategies, had no one in my corner. That's the problem when you're young and you don't have connections, I think. So, I didn't know better.

Justin Donald: Yeah. And this is the power of being in the right circles, in the right masterminds, in the right communities, being around people that have been there and done that and can advise and can help. Because as we know in the Lifestyle Investor community, tax strategy is just a playbook. And if you don't run the playbook, then you're not going to have a good play. If you run the playbook with the best people out there, world-class practitioners, you can pay little to no taxes legally, morally, ethically. It's all by the letter of the law. And I always say you don't want to tip Uncle Sam. I'm okay paying my fair due but you don't want to tip Uncle Sam. I don't feel like they're good enough stewards of our money to want to tip them.

Sean Kelly: That was a big learning lesson because while I was dealing with that, I put all the money in crypto into Celsius.

Justin Donald: Oh, man.

Sean Kelly: So, not only did I have to pay taxes on that, I didn't even have the money because I lost it on Celsius.

Justin Donald: Oh no.

Sean Kelly: So, I was still on payment plan up until a few months ago. Celsius released like 30% like two months ago. That's it, man.

Justin Donald: That is. That's a big lesson.

Sean Kelly: Yeah. It’s huge.

Justin Donald: Did you put all 2.5 there? Well, I guess it’s less of less taxes.

Sean Kelly: And then what happened was so I put 1.2 in there and then crypto crashed. So, it was already down like it went down with maybe 400K at one point but, yeah, I lost it all pretty much.

Justin Donald: Wow.

Sean Kelly: So, that was a big lesson and I think I was too careless putting it all into one platform. I should have spread it out more.

Justin Donald: Yeah. I mean, the lessons that we learn around investing when we actually lose money are the best lessons. So, in the moment, it's horrible. In the moment, the default is I want to blame someone, “Who can I blame? Who messed up?” instead of taking ownership, right? I've been there. I've done that. But later on, once you get past that blame and you say, "Okay. Let me be a big boy. Let me put on my big boy pants,” and recognize I made the decision to do this. I made the decision to invest. It is a loss, but what are the lessons learned? I think that's really important. And for me, I've learned the best lessons, the biggest lessons from losses, from losing money, from painful experiences.

Sean Kelly: Absolutely. Yeah. I like to share my losses, too. I think it's important. So, that was my biggest loss. My second biggest loss was in forex. Have you had any forex experience?

Justin Donald: I've not done anything in forex. Yeah. I don't do a whole lot on public equities and public markets. You know, I've had a lot of friends that have done currency trading and some have done well and some have really gotten crushed.

Sean Kelly: Yeah. I mean, here's what sold me because I was into AI. It was an AI trader. I would trade automatically and get you like 5% to 10% a month, which is crazy if you compound that.

Justin Donald: Yeah. That's outlier performance right there.

Sean Kelly: Yeah. So, it worked for like maybe seven, eight months straight and my portfolio was up to nearly $1 million. And then one day I lost everything, every single thing.

Justin Donald: That's so tough.

Sean Kelly: Isn’t that crazy?

Justin Donald: It works until it doesn't but that's the thing. Like, the long haul is such a tough thing and being able to take wins and pull.

Sean Kelly: I barely cash out anything. That was a huge mistake. I got too greedy. And one bad news day is all it took to wreck that AI.

Justin Donald: Isn’t that crazy?

Sean Kelly: Yeah, just one bad news.

Justin Donald: Public markets are very unpredictable. Private markets can be, but they react a lot slower. So, there's time. You can make decisions. Maybe it's not as liquid. So, liquidity could be tricky, whereas it's more liquid in these public markets. But for me, the outlying alpha that exists, the above S&P 500 performance just exists so much greater on the private side, on the alternative investment side. We talked about this on your show where if you look at all the reports, all the people that compile information from the most successful, wealthiest family offices in the world, but specifically also in the US, you'll find that between UBS, JP Morgan, Goldman Sachs, KKR, I mean, all these groups, and there's a bunch of others that just aggregate not banks, but other groups that will aggregate private office or family office data, they're generally between 49% and 59% in alternative investments because the performance of those to the risk is greater performance to less risk.

Sean Kelly: Right.

Justin Donald: And their public equities, their stock market portfolio exposure is a much smaller percentage. Usually, it's about 15% to 25%. So, that is an interesting, fascinating thing. And that's also influenced and swayed me in the way that I look at things, the way that I kind of evaluate deals. But I've learned a lot of lessons on both sides, on the investing in public equities, investing in private equity. The thing that I'm really proud of, so I've made tons of mistakes, but I've made very few repeat mistakes. And that to me is that's the key because I'm learning lessons every time. And I'm finding ways to get better, to get smarter. And my goal is to help educate people in my community on the same thing. How do we get better? How do we get smarter together?

Sean Kelly: I love that. You just talked for three hours about your seven losses out of 140, which is crazy because you barely had any but you're even focusing on those with your community, which I love.

Justin Donald: Yeah. It's been a really exciting experience. I mean we, knock on wood, have had a tremendous amount of success. Our deals are going well, trending well, or finished well, as a general rule. And it's just a small percentage. It's less than 5% of the deals that we have done. It's actually less than 4% of the deals that we've done, that either, A, have gone bad or, B, have hair on them and could potentially go bad.

Sean Kelly: Yeah. And that wasn't even your fault. It was COVID, you said, for most of them.

Justin Donald: Yeah.

Sean Kelly: So, you did what you could.

Justin Donald: That is right. I mean some of them, it's like there's nothing you can do. You can't impact what's going to happen in the economy. You can't foresee that. Sometimes it's mismanagement. Usually, it's mismanagement. Sometimes it's fraud. That's rare but it happens. It exists. And a lot of times it's just market timing or a combination of all those, right? And so, I think we've done a good job of playing on the safer side of things, deals that if they go bad, you can't lose everything. If they go well, you can make an outsized return but also doing things that are more sure things versus the speculative early-stage type of investments. You know, we really try to follow what the family offices do, which is 1% of net worth being exposed to these really high-risk type of deals, angel deals early, early stage seed round, pre-seed round type of deals.

And then the law of numbers should kick in. So, if you're going to do that and if you're going to play the venture game, most people recommend 4% to 10% of your net worth in venture. But that's where you're going to be investing in a fund that has many companies and most will probably go bad but you'll get a handful that really get the performance of the fund and earn the return overall.

Sean Kelly: Venture got hit hard, right, recently with the valuations I saw, especially in tech.

Justin Donald: Yeah. I think tech's getting hit hard, you know, venture as a whole. I mean, there's definitely niches in venture that are totally fine but, yeah, I mean most markets got hit pretty hard. I mean, some real estate markets did, some didn't. I mean cap rates for sure have changed and as interest rates have but, yeah, I mean this is it. It's understanding the seasons. And there will be more of these seasons and it's understanding how to perform best in the season you're in and do the best you can to predict or see the signs of the seasons to come.

Sean Kelly: Yeah. But the skill you've developed is great because even during recessions, you can still analyze deals and make money.

Justin Donald: Yeah. The goal is to find either, A, deals that are so far under-market, it's really hard to lose money and, B, recognize the trends of what's happening right now. Right? So, what is going to be mainstream that is just trending today? And what can you be on the early side of that wave on without subjecting yourself to too much risk?

Sean Kelly: Right. That balance.

Justin Donald: Yeah. So, I think that's really, really important.

Sean Kelly: Absolutely.

Justin Donald: So, yeah, it's interesting though, in investing, and you've experienced this too. We'll talk about some of your investments. Like, you learn because you have money in like you have skin in the game. Well, now all of a sudden you pay attention, right, when you got some money in the deal. When it goes well, it's really easy to kind of be like, "Oh, man, I'm really good at this.” And so, the lessons aren't as rich. It's almost like ego gets in the way of lessons. So, what I try and do is at any point in a deal, I've got this tracker that tracks every deal that I do. And I will like anytime there's a learning lesson, I just go to my tracker. I plug it in for like lessons learned. I got a tab and we've got a mastermind member, Dave Allred, that also does this. And he's got lessons learned. He does this at the end of every deal. And I like doing it at the end but I've learned stuff in the middle of these deals, too, that I want to capture that I'm worried with all the 400-plus deals, I'm going to forget some.

Sean Kelly: That’s a lot.

Justin Donald: So, I got to capture it now.

Sean Kelly: Yeah.

Justin Donald: So, I do think that's important, but my best lessons, bar none, have come from losing money.

Sean Kelly: Wow. 400 plus deals. That's incredible that you're able to manage that many.

Justin Donald: Oh, it's crazy. And for a while, I did it myself. Now, I've got a team, and that is helpful. I mean, I don't know how I could do that myself.

Sean Kelly: That's crazy, dude. Congrats on that. So, was the goal just to scale that?

Justin Donald: Yeah. Yeah, I enjoy it. You know, this has become a hobby, a passion project, and we've gotten good results. And so, I want to be able to teach people what that looks like. You know, the track record has been really good. And again, I want to knock on wood because anything can change, deals. I mean, I fully recognize that more deals are going to go bad in the future. You can't, like, understand everything. You can't know that everyone's a good actor or a bad actor early on. So, as an investor, you're going to experience everything. You're going to have deals that go well. You're going to have deals that go poorly.

You're going to have deals that you lose everything. You're going to have deals that you only get a partial return of your investment. You're going to have deals that return nothing, but at least you get your money back. You know, you’ll have deals that they told you is going to be a 15% IRR, but you only get 8%. You're going to get a little bit of everything. And the goal, the key here is don't put your emotions in front of logic. Don't get bent out of shape when you lose money. Don't get out of the game because of it. Learn from those lessons. And emotions are going to slow down your ability to like think and process. And generally, they're not going to lead to good results.

Sean Kelly: Right. Yeah. With my house, for example, like I waited two years to buy it because everyone was saying the market was going to crash. It never crashed. And I'm curious what percentage of your investments are real estate because they keep saying it's going to crash but like I don't see a drop in Vegas. I don't know about here.

Justin Donald: Yeah. I mean the family offices, the wealthiest people in the world generally are somewhere between 15% and 25% in real estate. I got started in real estate, so my portfolio is probably a little more heavily weighted real estate. I'm probably sitting around 35%, 40% real estate, so I may be on the higher side of that but I also am on the lower side of public equities just because I have found better returns on the private side. I have personally done much better than if you track the S&P 500 return over the last 10 years, 15 years, 20 years. I mean, right now we're on a tear and things look good but if you balance it out over the long haul and even over 30 years, for example, like 30 years, I've been investing for just under 30 years.

And so, if you look at it for that time frame, my private alternative investment portfolio has by far outperformed my public portfolio or even it's largely outperformed even just an S&P 500 index. So, for me, I've just slowly whittled away from my public exposure. But I'm not against it. I still have a few stocks. I still have Berkshire Hathaway so I can go to the meeting.

Sean Kelly: Oh, you get invited to meetings?

Justin Donald: Yeah. As long as you own, yeah, I mean, there are ways to go even if you don't own the stock but if you are a shareholder, then that is your ticket in the door.

Sean Kelly: That’s cool. It's almost like a mastermind.

Justin Donald: It is. Yeah. I mean, really cool experience. In Omaha, I got a chance to do it. Actually, luckily, I got a chance to do it before Charlie Munger passed.

Sean Kelly: Oh, wow.

Justin Donald: Or I go last year, so I was able to. Not this year but last year. So, that was good. And getting a chance to check out Omaha was pretty cool.

Sean Kelly: Nice. I got to get out there one of these days.

Justin Donald: Yeah. So, tell me about crypto now. I mean, it sounds like you've had some losses in that space. Are you still bullish there? Are you still heavily invested? What do you think of Bitcoin?

Sean Kelly: I mean, Bitcoin, Ethereum, and I did it really well with Solana. So, Solana I got in super early, and Ethereum I'm up a lot because it was down to like a thousand I think last year, right?

Justin Donald: Yeah.

Sean Kelly: So, it's already back up to 3K plus and it was at 4K earlier this year. So, yeah, Ethereum and Bitcoin I feel like you can't really go wrong in my opinion.

Justin Donald: I agree with that. And I would say for sure I feel that way on Bitcoin. So, for me, my exposure on crypto, so the wealthiest families once again if you go back to these reports, a lot of them aren't even in crypto but the ones that are generally are at about 1% of their net worth in crypto. I know more of the progressive family offices and some of the younger people that have family offices that have made their wealth at a younger age, like you. And a lot of them have just really scaled over time. Some of them are 5% or 10% of their net worth in it.

Sean Kelly: Wow.

Justin Donald: But most are really in that 1%, maybe 2% range. And so, that's kind of what I've modeled. And of that, I'm 90% Bitcoin, 10% Ethereum or 9% Ethereum, 1% moonshots.

Sean Kelly: When you are making your first few millions, were you 100% in one industry? Because that's where I'm at. So, I made all my money in crypto. So, now I need to diversify. But still, like 80% of my money is in crypto, you know what I mean?

Justin Donald: Yeah. And I think it's dangerous anytime you're not committed in anything because if the tide changes, then it can really mess up net worth. So, I mean, most people make their wealth via concentration, but they grow and maintain. They maintain, grow, and really compound it, have the exponential growth through diversification. So, I did get my start in real estate. And so, at one point in time, I was almost, I was 90%, 90 some odd percent real estate. And I have scaled that back down to probably closer to 35% to 40%. And at some point, I may liquidate my whole real estate portfolio, but for right now, it's probably not the right time, not the right season.

But for the right offer, I mean, in retrospect, I probably should have sold the whole thing in 2021 or 2022. I got these crazy offers, and I should have listened to trying to remember who it was. It was Sam Zell, who's another mentor or hero of mine, someone I followed for a long time because he was early in on the mobile home park business. But I think he's the one that said that if you won't buy it, if someone makes you an offer and you wouldn't buy it for that, then sell it. So, I should have sold because these offers were crazy. These offers were like five times the basis I was in.

Sean Kelly: Damn. Five times? That's like unheard of in real estate.

Justin Donald: I really should have done it but that's all right. That's a great lesson where I let the tax tail wag the dog and instead of just selling, I said, "Well, let me see how I can mitigate the taxes I would pay.” And I went down a few different paths with a few different strategies, and I figured out ways to mitigate it legally and this would have been a great play. But at the time that I then had it figured out, those offers weren't on the table. The economy was changing.

Sean Kelly: Yeah. It was that quick.

Justin Donald: Interest rates were going up. Yeah. So, a regret of mine is I was too short-sighted. I should have just paid the tax. You know, it's too short-sighted and maybe there's greed there where it's like I wanted to keep more of it. I wanted to capture more of it. And then it just was trying to optimize and maximize more than was helpful.

Sean Kelly: Wow. So, you wanted to get fully out of real estate?

Justin Donald: It wasn't I wanted out. It was just that the offers were ridiculous. Just ridiculous.

Sean Kelly: Got it. Wow.

Justin Donald: Yeah. So, think about if you and I'll just use examples. I'm not going to use real numbers here but if you got into real estate and your own dollars are only $10 million or $20 million, but you could get 100 million, 120 million, 130 million on the way out, like it was a huge differential.

Sean Kelly: Yeah. So, you were up 10X.

Justin Donald: Yes.

Sean Kelly: Holy crap. On real estate, I've never heard of that.

Justin Donald: On many assets.

Sean Kelly: Yeah. That's incredible.

Justin Donald: Blended. Blended. Some were higher, some were lower.

Sean Kelly: Yeah. But for real estate that's literally unheard of.

Justin Donald: Well, on with real estate, what it is, I mean, I've been in the business for 15 years, right? I've been buying real estate. Actually, I've been buying for longer than that but I've been in mobile home parks that long. And so, what it is, is you're at a point where you can use 15% or 20% down to be able to buy these assets. So, you're using bank lending or other types of OPM, other people's money, to get these. And so, your skin in the game is low compared to what you can get. So, yeah, you got to pay off the debt on an exit but the ability to have a huge return at scale is pretty significant. You buy one property, maybe you can make a little bit. You buy 20 properties, well, now, all the groups that don't want to aggregate from 1 to 20 are in the game to buy your portfolio from you.

Sean Kelly: I love that.

Justin Donald: And they're willing to pay a premium because they don't want to do that. They're not going to invest that time and effort into it.

Sean Kelly: Yeah. That's cool. So, you're at the point now where you're just living off your passive income from all your investments.

Justin Donald: Correct. Yeah. And really, when I turn 37… So, I'm 44, I've just turned 44, what, two weeks ago. And when I was 37, that's when we achieved financial freedom. I probably had financial survival income at about 35.

Sean Kelly: Okay. Yeah, I want to get to that stage because I'm still working for my money like I still need to work. Yeah, I'm not at that point yet where my money can make… I would probably need 250K a year to say I'm free.

Justin Donald: Yeah. And by the way, it's great that you know that number because now that you know it, you can just start taking steps to get there. And I think that's great. Like, the first step for a lot of people as they accumulate some cash. Maybe they have an exit. Maybe they have a big windfall in crypto or something or some investment that they do, but they've got this starting point. And then from this point, you don't want to be like you got to be strategic so you don't lose the money which you've experienced this. Anyone who's invested is going to lose money at some point. That's just the nature of the beast. But the goal is to lose less times than you win and to lose smaller amounts than you win.

Sean Kelly: Right.

Justin Donald: Right? And then you win. You might lose a battle here or there but you don't lose the war. And so, I think it's great that you know your numbers, and then you can just put together, you know, I interviewed a number of people and one specifically in the Lifestyle Investor mastermind. I know we've talked about that with you. He said his first time he celebrated passive income was when, and you can go back and check out the Asim Hafeez episode but he said, “I covered my Netflix account,” like I celebrated because that was passive income that covered that. And then he just grew it from there, right? So, then it was like utilities, car payments, mortgage so on and so forth. And it just kept adding up deal after deal after deal.

Sean Kelly: I love it.

Justin Donald: But 250K sounds like a lot more money than it really is. I mean, let's break it down, divide it by 12 months, and it's a lot less.

Sean Kelly: Yeah. Because my mortgage alone is 12K a month. I don't have kids yet. So, if I have kids, that number probably needs to be higher. The food is like 5K a month and then travel and everything.

Justin Donald: So, if you're between 25K and 30K a month, let's just call it 27K, that's what you need to hit that lifestyle. By the way, it's a lesser amount for your survival income, right? So, what's the survival income? Well, your travel would be a little bit less. Your food would be a little bit less, right? So, maybe like you could live and get by at, I don't know, 75,000, 100,000. Not as luxurious of a life as you live today but a pretty darn awesome life, especially if you didn't have to work. Now, you hit that one first so maybe it's just figuring out how do you get to 7K to 10K a month, and then from there you get to how do you get to 27K a month. And it's a game changer because when earning money shifts and time spent like working for money when that shifts from a ‘have to’ to a ‘get to,’ it's a big difference. And I've found that my creative juices just started flowing.

Sean Kelly: Yeah, because it’s not forced anymore. Only things you want to do.

Justin Donald: That's right. That was very powerful.

Sean Kelly: Yeah. That's the goal. For every entrepreneur, that should be the goal.

Justin Donald: Yeah. Well, I'm excited about all the cool stuff that you're up to. You'd said, hey, you became a millionaire at 24. You're a multi-millionaire now. The goal here really soon is become a decamillionaire, which is 10 million plus. And then eventually, by your 30s, you'd like to be a centimillionaire, which is a 100 million plus.

Sean Kelly: Yeah. I want to hit 30, decamillionaire, and hopefully by 40, centi. I know it's ambitious, but…

Justin Donald: I love it. Got to have big goals to have big achievements.

Sean Kelly: But I listened on Sam Parr’s podcast. Some really smart guy said you only need about 50 to 60.

Justin Donald: Yeah. I mean, if you're doing it right, I mean, you should be able to, I would make the argument you could do it on way less than that. I mean, I think you could live a killer life on 20 to 30.

Sean Kelly: Okay.

Justin Donald: You just have to be smart with how your cash flowing those dollars, have the right, you know.

Sean Kelly: Well, with your investments, yes. He was saying 60 on 4% a year, but you're getting like triple that so, yeah, that makes sense.

Justin Donald: Yeah. So, that's cool. I mean, so that's another number. And by the way, once you get 50 million, you're like at that point considered an ultra-high net worth individual. So, sometimes you'll see that acronym written out, but 50 mil is that magic number. And then another category that you can put next that a lot of people are working hard, we got a bunch of people in our mastermind that are centimillionaire already, and they want to move to demibillionaire, which is 500 million and above.

Sean Kelly: Oh, I haven't heard of that one.

Justin Donald: So, that's the one right before billionaire.

Sean Kelly: Got it.

Justin Donald: And then really, once you get in the 100 mil, the centimillionaire, when you become a centimillionaire, you probably should start thinking about multi-family office. Some people say 50 million. I think it's probably more at 100 million. And then single-family office is probably more like the 500 million. Maybe you can make the argument 250, 300 million. I still don't think it makes sense.

Sean Kelly: Yeah.

Justin Donald: Because the salaries to run it effectively is minimum probably 3 mil a year up to 14 mil a year. So, I really think it needs to be at like 500 mil plus, maybe even closer to a billion.

Sean Kelly: If you maintain your numbers, you're going to be there, right, in my 20 years?

Justin Donald: Yeah. You know, it's not a goal necessarily. If I hit it, I hit it. What I don't want to do and I shared this a little bit on your episode on your podcast but I don't want to hit that number neglecting my family. So, if that happens and I become a billionaire, great but I'm going to make the choice of family and friends and experiences and all that. And if I don't ever hit it, that's okay. That's not the end all, be all goal to me. If I end up hitting it while putting time in with family, friends, experiences, travel, all the stuff that I want to do, then great. It's just not, you know, that number I know to become a billionaire drives a lot of people. That does not drive me. Owning my time really drives me.

Sean Kelly: Yeah. Because you could retire right now.

Justin Donald: Yes. Well, and I did for a year. I mean, we traveled the world for a year, spent a ton of time in Europe. I went to 13 different countries. I mean, it was an epic experience. But at the end of that year, I was like, "Okay. I need to do something like I'm ready for the next challenge.” And part of that next challenge was me learning and me growing in a few areas. And part of it was starting Lifestyle Investor, where I can teach other people the things I've learned. Let me teach you all the mistakes I've made so you don't have to copy them. You can just learn them vicariously through me and then, hey, let's learn some other cool stuff together.

Sean Kelly: I love it. Yeah. Can't wait to be part of it then. I'm going to apply later this year.

Justin Donald: I love it. It's going to be fun. Well, thanks for being on the show. I appreciate you being here. Any words of advice as we wrap things up?

Sean Kelly: Join a mastermind. I know we didn't really touch on that but, yeah, I'm part of three masterminds. I met Justin through a mastermind, and my life has changed through masterminds.

Justin Donald: That's right. You give a shout-out to our mutual friend, Jim Dew, since we met at one of his events. And I think the world of Jim. He's awesome and brilliant and smart and wonderful and so is his wife, Mimi. They're just amazing.

Sean Kelly: Saved me a ton of money already.

Justin Donald: That's right. And they're really good at tax strategy. He was on my podcast as well. I'm sure he's on yours. I mean, it's just good to have a good tax strategy. And I put them in a top five category for that. And then you are in a really high ticket mastermind. So, sometimes it's funny like our 55K a year price point is really high for a lot of people. And that's intentional. We want to weed people out. We want the cream of the crop. And by the way, if that's not right for someone yet, that's okay. And we have a lower-tier mastermind. We have a tribe of investors that's half the price point but we are really selective with who gets in the Lifestyle Investor. And so, it's funny to me when sometimes people are like, "Oh, that's really expensive.” Yeah, it is but you get what you invest in yourself. You joined 100 million, which is a $100,000-a-year mastermind, right? I mean, that's really investing in yourself.

Sean Kelly: Yeah. And when I joined I only had 200,000 in my name.

Justin Donald: Oh, my goodness. You took half your liquid net worth.

Sean Kelly: And you got to be able to live with the fact that because some people join these masterminds and they get pissed because there's no immediate ROI, right? So, when I spent that money, I didn't make it back for like two years, but I knew that the connections I would make there, I would eventually make it back. And now I made it back tenfold because I still work with some of the guys there that I met.

Justin Donald: That's awesome. And that's what it's about. To think linearly, like a lot of people are like, "Well, I need to get the ROI, the return on investment.” And they look at it and they measure it sometimes by like the deals or what. You can knock the ROI out with tax strategy. Like, one good tax strategy can save you more than 55K. One good deal that you do can make you more than 55K. One good connection with someone can make you way more than that. And so, I don't like the linear look. I like that you have a bigger outlook where it's like, "Well, in time, that's going to pay off. And I don't need it to pay off right now. Whenever it does, it does but I know that I'm going to make that money back.”

Sean Kelly: 100%.

Justin Donald: That's for me like so now I went through and did an audit of all my masterminds. So, I run two masterminds and I'm in 14 so 16 total.

Sean Kelly: You’re in 14?

Justin Donald: Yeah.

Sean Kelly: Holy crap.

Justin Donald: It's ridiculous. I don't attend everything because I figured out that I can be selective with what I attend and I can get the value. So, mine range anywhere from 10K to 55K, right? And so, for me, I know in one conversation, one mindset shift, one actionable strategy, one networking situation, one right fit person, like I know that I'm going to get a return. So, I don't feel like I have to attend everything. I just need to be really proactive at the things I choose to attend.

Sean Kelly: Wow. I'm in two and that's already a lot for me, man. Fourteen is crazy.

Justin Donald: Well, I don't recommend that but what I do recommend is like putting all the time that you can into taking yourself and your education and your network to the next level. And you're obviously doing that. You've been successful at a young age. You're investing your time and your resources in your peer group, in masterminds and communities, in networking. And you have goals and they're laid out nicely. I love it. This is awesome. What a great episode. I feel like you have inspired a ton of people. You've inspired me. I was not where you are when I was 24 so well done. I think sky's the limit. And where can our audience learn more about you? Where can they find you?

Sean Kelly: Yeah. Instagram is probably the best. Sean Mike Kelly and then Digital Social Hour podcast is the show.

Justin Donald: That's awesome. Well, so great to have you here in person. Get some time, you and I, we're going to go grab some dinner now with Brad Weimert and just kick it a little bit before your flight home.

Sean Kelly: Can't wait. Thanks for having me.

Justin Donald: Awesome. Well, I love wrapping up every episode with one question for you, our audience. And that question is this: What is one step that you can take today, right now towards financial freedom? So, living a life by design, not like most people by default. What is one thing that you can take from Sean today and put into actionable steps in your life to move you in that direction of financial freedom? Thanks, and we'll catch you next week.

Sean Kelly: Peace.

powered by

Justin Donald is a leading financial strategist who helps you find your way through the complexities of financial planning. A pioneer in structuring deals and disciplined investment systems, he now consults and advises entrepreneurs and executives on lifestyle investing.

Keep Learning

The Power of Hosting Epic Events to Curate Relationships & Accelerate Wealth with Thanh Pham – EP 272

Interview with Thanh Pham  The Power of Hosting Epic Events to Curate Relationships...
Read More about The Power of Hosting Epic Events to Curate Relationships & Accelerate Wealth with Thanh Pham – EP 272

How Live Challenges Created Predictable Cash Flow and $100M+ in Revenue with Pedro Adao – EP 271

Interview with Pedro Adao  How Live Challenges Created Predictable Cash Flow and $100M+...
Read More about How Live Challenges Created Predictable Cash Flow and $100M+ in Revenue with Pedro Adao – EP 271

A Fresh Perspective for Vetting New Business Deals with Pat Flynn – EP 270

Interview with Pat Flynn  A Fresh Perspective for Vetting New Business Deals with...
Read More about A Fresh Perspective for Vetting New Business Deals with Pat Flynn – EP 270