The Investor Community That Teaches You How to Build Wealth & Freedom with Ryan Casey – EP 263

Justin Donald: What's up, Ryan? Good to have you back on the show.

Ryan Casey: Yeah, it's been a couple, what, a year or two since I've been on. Excited to.

Justin Donald: I know. Well, I'm excited for today's session because it fits perfectly with kind of what's going on in the world. I think the number one thing, I mean, people are just constantly asking me, "What's next for Lifestyle Investor? And what's new? And what's your vision of the future?” Just all these things related to what you and I are doing together. The team has grown so much. I can hardly keep up with all the things that we've done. So, I figured, why not bring the guy who's running the show, Ryan Casey, back on so we can kind of talk about and walk through all the things that we're doing, kind of where we were, where we are, where we're going, and maybe highlight some of the cool things that we're building out right now. So, glad to have you here.

Ryan Casey: Yeah. It feels like every few months, something happens that's just really amazing that makes us look back and say, "Wow. Can you remember back when it was just this big or whatever, what's happening with trips and events, all sorts of cool stuff?”

Justin Donald: Totally. I'm always kind of like pinching myself, like how do we have it so good? Like, how have we built such a cool thing so quickly? Because this type of community, I mean, it generally does not grow as strong, as fast, as robust as we've done it. I mean, even other people in the mastermind space are like, "You guys are an anomaly.” What you've been able to do, how you scaled, the number of members, the quality of members, the impressiveness in such short order. And so, I feel really blessed and really blessed to have you on board to help us kind of usher in a new era. It's funny, like I think back to your big joke, like, “Justin, when you started this mastermind, it was held together with duct tape.” And that's the truth because it was me in the beginning.

And then we brought on an executive assistant for me who's grown. And people that know Tee love Tee. She's transitioned into our Operations Manager. But for the first few years, it was just her and I kind of holding this thing together. And even earlier days than that, I remember I shot you a text and I was like, “Hey, I've got some friends that were doing these little happy hours. We're drinking some good wine and talking about it, and then talking about deals that we're doing, vetting them together. Do you want to join?” And it was just like four or five of us. I think you are number five or number six. And that's really kind of where things got going. I remember thinking, "Man, I'd love to have you involved in a greater capacity.”

And you're kind of like, “Hey, I've got enough on my plate. I've got these two Orangetheory Fitness studios that are two of the top in the country. I'm spending time there.” You were building out a sales training program at that time, and I couldn't get you to commit, but you wanted to be involved, right? You were like the OG member that wanted to do a little more and didn't just want to be a member. And I think there was a tipping point when I brought on an EOS team that really just didn't fully understand our culture, our dynamic, the way we are building it. And I remember I don't think I sent you a text. I think you sent me a text and you're like, “Hey, man, if we can move on without the team, I'm ready to step in.” So, I'd love to hear your thoughts.

Ryan Casey: Awesome to meet with you. I'm like, “I need to fly down.” But, yeah, when I first got the text, I'm like, "This is great.” I had just left my job, and then COVID happened, so my Orangetheorys were closed. So, I'm like, “I'd love to talk shop with investing.” And then when you started it, wanted to be involved, but I'm like, “I just want to help. Let me just do a little bit.” And it wasn't until kind of that point where, okay, you need somebody who's under. It was about two years later. You've been running it for two years. And it was such an amazing group that I really feel like you needed somebody who was familiar with the group to keep the great things happening, but grow it, also grow the way you wanted it to grow.

Because initially, you're the Lifestyle Investor, and then all of a sudden, you have a job. “I need to get an EA. What do I do with these thousand Google Docs?” Which was the opposite of what the whole book's about. So, when I got in, I knew, okay, I know we want to grow it, but I know we don't want to send you on a road show and be speaking everywhere. Like, how can we grow this and make sure we're all living the Lifestyle Investor life? For the people, that's our top core value with our staff is, hey, we need to be Lifestyle Investors too. There's no badge of honor for grinding on our staff there.

Justin Donald: Yeah. Well, I'm glad that we brought you on board because you've really built a lot of the systems, the protocol. You've helped us measure things. I mean, when we talk about the structure, you've built so much around the structure. So, what would you say you're most proud of, and what has changed?

Ryan Casey: Yeah. I think that was something I wanted to add is to have some kind of flow, have some kind of expectations when people are joining. Because really it was, “Hey, I heard this awesome guy on a podcast and I read his book and I want to get proximity with him and invest in the deals that he wants to invest in.” And that was kind of the first couple of years. And one of the challenges is we had such a diverse group. We had people that are hiring W-2s. We had people that just had a monster exit. We had people that are operating their business at a high level but want to step out of the day-to-day. So, it was really tough to say, “Hey, here's the path for all of you to take, even though you're in totally different positions.”

And I think we finally cracked a lot of that, and I can get into it a little bit with you. If you've been listening to the podcast, you've been on any of the recent webinars, you hear a lot more about allocation. You hear a lot more about investment criteria. We've always been big on due diligence, but we have much more of a structure. We created the Vetting Deals course for it. So, now when somebody comes in, instead of jumping on their first deal and writing checks, most of our members don't invest anything for their first two or three months. They know their first few months is, "Okay, let me look at what my current allocation is. Let me look at how the wealthy are really investing,” and you do such a great job of sharing the info and sharing.

It's cool seeing how it changes year to year and where the shifts are happening and why those shifts are happening. And then saying, "Okay. Well, for my personal goals of becoming a lifestyle investor, what would be the right allocation for me?” And then building out their own investment criteria and then starting to look at a much narrower group of deals that would fit that.

Justin Donald: Yeah. And I think also just helping people understand what I like to do is synthesize the data that is out there and what the wealthiest people are doing. So, when you think about the billionaire class, the single-family offices, and I have plenty of data on multifamily offices as well, but there's a difference between single-family office investment portfolio, investment thesis, and multifamily. So, to describe the difference between the two single-family offices, usually billionaires, multifamily offices are usually multimillionaires, but usually at like the $50 million or $100 million net worth starting point. And so, I like to democratize that type of content, so that it is understandable, it's implementable, for our community.

And so, that's what you're talking about like your investment criteria, your asset allocation, and then even deal flow. I know we'll jump into it, but in the beginning, it was kind of like, “Hey. these deals look cool. I'm investing my money in it, and maybe others are interested versus building actually a robust system of like more institutional-level, institutional-grade type of diligence. I think it's important that we wanted to pivot, right? We wanted to go like, how do we make smarter decisions? How do we do less FOMO? My wife's big on JOMO, the joy of missing out, and she's a total contrast to me, where I've spent most of my life in FOMO or shiny object syndrome. Like, how do we get better long-term results, right?

Ryan Casey: Yeah. I think, well, you just sharing that JOMO, about Jen saying, has really impacted the mastermind, where the first couple of years I remember hearing people like, "Ah, I really wanted to get into that.” And now I hear people like feeling good about saying no. They're like, "Oh, that was great, but you know what? It didn't hit my investment criteria.” They're still investing plenty, but I think it's also changed the type of person we've attracted. I think the first couple of years of the mastermind, we had a lot more people who were new to alternative investing. And now, as people hear more, they say, "You know what? I've been investing, but I need to up my game on my due diligence.” And I love what we're doing with the due diligence side. So, I want to go there because I want to up my game on how do I vet these deals personally and learn how to do that.

Justin Donald: Yeah. Well, I'm excited. We're going to spend some time there, and I actually think we should break down the four different groups that we have, the three main masterminds, and then we've got an open community, but let's start with Lifestyle Investor. That is our flagship product. It's what everything was built on. It's the foundation of everything that we've done, and there's kind of a trickle-down effect from there in every other group, right? But there's nothing that is as robust or as comprehensive as the investment opportunities, the tax strategies, the member experience for the Lifestyle Investor mastermind. So, where are we investing right now in member experience?

Ryan Casey: Yeah. And so, the Lifestyle Investor Mastermind is just over five years as it was really almost six now, with some of the beginnings, startings with it. But as far as the member experience, one of the biggest changes has been how much we are investing with the due diligence. The early couple of years diligence was mainly you, and then starting to reach out to your network, which is incredible of, "Okay, this is a real estate deal. Who do I know in the real estate space?” That still hasn't changed, but what we've done is now we're putting about $250,000 to $300,000 additional into our due diligence. So, we have some AI tools from a couple of great groups, but we have an in-house real estate person, and we have an institutional-grade process for some of our private equity ones, which is not cheap.

Justin Donald: It's not cheap.

Ryan Casey: But we have a great partnership. They've loved working with us, so they've actually changed how they work with us versus how they work with most of their clients. But these are the types of people where they're investing hundreds of millions of dollars. And our members are able to get access to that with much, much lower minimums, which is really cool.

Justin Donald: And reduced fees. I mean, we do a great job of having reduced minimums, reduced fees, and oftentimes even some preferred terms, like some better returns, better class of investment share. So, I think it's really neat. I mean, first and foremost, most people don't get access to them. But secondly, they certainly don't get access at these terms. But I think it's notable to say that we're spending at or upwards of $300,000 a year on our due diligence. And I want people to know that because I don't know any other group, any other mastermind, any other investment community that's actually doing that. That, to me, is really important that we can be kind of like a standalone in that category for the way that we diligence and really kind of having that institutional-grade systematic approach to vetting deals.

Ryan Casey: And that's two of the reasons why I see people coming into the mastermind. I think every member has, I've heard say, "If I had been here, I would've been invested in some of those deals that I did in the past that have not gone down.” And most of them aren't going to spend $300,000 on due diligence themselves, but that's going to save them from writing some bad checks. The other thing you mentioned, though, is we're very different from most groups, is that you can't pay to play. Somebody has a great deal. They cannot pay us to present the deal. It's the opposite, right? We make them pay to go through background checks. They have to pass diligence. And when somebody invests with us, we don't make a dime off their investments.

We are an annual fee. That's how we make our money, right? Where there are some groups out there that are like, “Hey, let us teach you how to invest, and we also have a fund that we make a huge carry on,” and it's biased. And so, even our sponsors, we have some great sponsors that have deals, but we have them present. We like their deal, we like who they are, and then those people are then invited to be a sponsor, where they get access, where they can come to some of our events and be around our members. We don't take money. You can't pay us to put your deal in.

Justin Donald: I think that's a great distinction because most groups in the industry, that's exactly how it is. It's pay to play. And then I think you know that there's always a bias where if you can make money on someone else's money, you're always going to promote those types of deals. And by the way, you see this in the institutional realm anyway. Like, all these, you make money on assets under management or you make a carry or you get some sort of a kickback because you're a wealth manager that is offering deals, there's some sort of fee that you're getting to have those deals on your platform, we wanted to be the opposite of all that.

I've heard many times I'm crazy, A, for not having a fund and, B, for not taking a carry because of how much money we could make. But I wanted to be the one place that really eliminates that bias. And people know that I make money only because my money's in the deal. You make money only because your money's in the deal. That to me is the cleanest.

Ryan Casey: Yeah. It's not for lack of offers because now I have to take all those calls.

Justin Donald: That's right.

Ryan Casey: Not so much saying yes. So, I'm the no guy. If you get a call with me, be careful.

Justin Donald: And something else I think that's really cool that's changed are the events that we're doing, and I'd love to talk a little bit about that because…

Ryan Casey: Where would you just get back from? I mean, you've only been home a few days, right?

Justin Donald: That's right. Yeah. I just got back from our Japan Lifestyle Investor trip. We spent time in Tokyo and Kyoto, and a small little stint there in Osaka at the end, but it was just a world-class trip. One of our Lifestyle Investor Mastermind members, Stephen Backholm, put it on and did an incredible job. He put on the Mexico City trip that we did last year, where we hit up, same thing, like we hit up all these Michelin star restaurants, hit up all these world famous cocktail bars. So, in Japan, I don't know, we hit seven, maybe eight Michelin-starred restaurants. We hit up the number 18 cocktail bar in the world. That's at the Four Seasons, where we stayed in Tokyo, and just had an incredible experience.

Ryan Casey: Did you have Wagyu at least once or twice a day?

Justin Donald: So, literally, 10 days straight, I had the Japanese A5 Kobe Wagyu steak, and most days I had it twice. It was so good. Of course, I did a ton of sushi, but my favorite food I've ever eaten is Japanese, just top of the line, A5 Wagyu. It is so good.

Ryan Casey: Oh, delicious. Well, we've had some trips. We have Napa actually coming in a couple of weeks, so I'll be going to that. KC's, actually, it'll be her first trip, Lifestyle Investor, coming as well.

Justin Donald: That's going to be fun. Last year was one of the highest-rated, most exciting trips that we've done, so much so that we've turned it into an annual trip with Mario Matavesco, my personal sommelier. We just love Mario.

Ryan Casey: Oh, he’s got such great connections that people love him, and where we can get access to is incredible there. So, I'm looking forward to Napa. So, we do a few of those trips a year. We do a couple, two or three, where it's trips, usually seven to 20 people on those. We also have quite a few member meetups where I don't think I've ever seen a post catch fire in our portal as much as when I said, “Hey, if anybody likes golf, just put golf, and we'll tag you golf, so that way you can see which members golf when you're traveling.” And within five minutes, there's a third of the group on there. So, I know we'll have some more golf outings there as well.

Justin Donald: Yeah. We've got the Asheville event. We've got the horse racing event. They're doing the second one at the Birmingham Track. That's getting set up. We got the helicopter and hogs hunting event in February. I mean, we're putting on some pretty cool things, and that doesn't even count, like all the smaller group trips where last year we did Hong Kong and Taipei City in Taiwan, and we're about to do Dubai, in Qatar. And so, just so excited for the travel and the life experiences.

Ryan Casey: Well, with the travel group we're having to present the open community next month, I think, we'll probably see a lot more travel on the horizon there from smaller groups putting together.

Justin Donald: Yeah. I mean, one of the member perks is having a concierge travel company that is really inexpensive but does incredibly good quality work. I've been working with them this year and have been blown away, and I've tried out a bunch over the years, and this group is just next level. So, I'm excited for another member perk to be supporting travel and lifestyle, and experiences with friends and family.

Ryan Casey: That should be launching probably around the time people are hearing this podcast.

Justin Donald: That's right.

Ryan Casey: The other events that have really been, those are smaller trips but are our live events. So, two years ago, we said, “Hey, let's do a live event in person.” And we did our tax course there. We did a one-day event. We had Garrett, we had Codie Sanchez there, and we had 40 people, small, intimate. And we said, "Well, let's do this a couple times a year.” And this last year, we sold out both times. We had to expand. We were planning on 70. We expanded 1 to 100. The other one, we said, "We know we're going to go over, so let’s…” I think we had 135 people there. And those were cool because we allowed paid tickets. I think we cut it off at 25. Both events, 25, and then the rest of them are members, members, and guests.

So, our members get to go for free versus the paid tickets, $5,000. And most of the people that go to those events, they then want to join the Mastermind after they see kind of what the events we put on for our members.

Justin Donald: Yeah. And when they get to a chance to meet the people, I mean, I think it's such a great way because not only do you have guests that are potential candidates for the mastermind, because everyone's vetted ahead of time, right? They're pre-qualified, they're interviewed, so they can feel it out. But then you have the members that get to feel out, “Hey, do we like these guests? Are they going to be a good fit?” And so, it really works well all the way around.

Ryan Casey: Yeah. And member feedback has just been great from those events, where more members want to come. It's getting to the size of the retreat.

Justin Donald: That’s right.

Colin Boyd: So, it's great. Anytime we get our members together, I think after the retreat last year, we had this group of members the night after, or is that the last night? And if you hadn't known better, you would've thought that it was a 25-year, 30-year high school reunion. And I think almost every member there was in their first year. That was one of either the first or second time that group had met in person, and it really warmed your heart to see how much the people connect.

Justin Donald: That's so cool. Well, and it's fun because, for me, I think it's important that since most masterminds don't do this, is that your spouse can come to anything. I really want people to do that together. So, our year-end retreat, we usually have 90% to 100% member attendance. Most people bring their spouses, so it's 150 to 200 people every single year. It's a pretty big event. So, it's fun seeing these other live events that we added in that weren't part of the original mastermind, now becoming so vibrant, and people just loving being at them. And I think it's also good to kind of mention that our tax bench has gotten deeper, right?

I mean, one of our big ROIs for the Mastermind, and I would say the single quickest one, is tax strategy. You have the right tax strategy. You can cover your annual membership dues in a moment's notice with a single strategy or with a combo of two strategies. But not just that year, every single year. So, I'd love for you to talk a little bit about our bench there.

Ryan Casey: Well, that was, I think, one of my first projects when I came in. And this is what we're really trying to do now. We have more information than anybody would need to ROI for years. So, newer calls that are trying to focusing on what's the upcoming trends, and how can we filter the information to get things quickly. So, our tax strategy database of, I think, we're at 65, 70 strategies there has links to all the different speakers that have come in. We've just added a couple more strategists over the last few months. We're constantly looking to add top-tier tax strategies, and we get sent tax strategies all the time. You have your bench of tax strategists that will vet the strategy, and a few of them, particularly, I love getting Jeff's responses because he doesn't hold back, and he is like…

Justin Donald: He does not.

Colin Boyd: And so, when we do tax strategies, we're not looking for, “Hey, what's the gray area? I don't care. Can we get away with it?” No, we don't want anything to do with that. So, we have a good tax strategy bench that we're continuing to increase.

Justin Donald: We say no to most deals, most tax strategies, but I think it's important to recognize that the 65, 70 strategies that we have, most CPAs have never even heard of them. I mean, if they've heard of them, they've heard of maybe like three to five. So, I mean, these are strategies from tax strategists, from tax attorneys, from true like IRS like well-studied expert type of people, that is based on the tax code. So, it's not like, “Hey, can we pull a fast one?” This is like, no, this is outlined in the tax code. You can most certainly use it, and there's supporting case study to show that you can use it.

Ryan Casey: They pass audits, all of those. So, I think one that we just created our InvestmentCriteriaGPT to help people go through that process, creating their own investment criteria, the TaxGPT is going to be one of the next there. Kind of instead of, “Hey, just look through this whole list and see what applies,” asking the questions and helping people there. But now we have the resources to back it up. You're not just asking ChatGPT, and it's pulling off of the web. Actually, it worked with where you're at.

Justin Donald: Yeah. And I think it's important for us, we do a lot of world-class education. I want the best and brightest. And one of those categories is tax strategy. So, we like to have three to four people a year, tax strategists, coming and sharing tips and strategies and things that work that most people don't know about, but it's funny because even if we stopped and never did a new session ever again in Lifestyle Investor, literally we never had a single new education session, our members could ROI on the existing library that has over 700 hours of content, and they could just focus on filtering what they need, like what do they want to learn about? We've got all kinds of other tools that help decision-making around that, but I think it's really cool to have that type of a document library.

Ryan Casey: Yeah. Most of our members, you know, they spend a handful of hours a month, and they're really pinpoint. And then we have other members that come in, that's their new Netflix.

Justin Donald: That's right.

Ryan Casey: But, yeah, we got a lot in there. Do you want to transition to another group here we haven't spent time with?

Justin Donald: Yeah. I think it'd be fun to compare the difference between the Lifestyle Investor Mastermind and the Tribe of Investors Mastermind. I think both are incredible, and I think both it's really what's right, the right fit for the right person. But Erik Van Horn and I run the Tribe of Investors Mastermind together with you, Ryan, and we'll talk about the impact that you've had since bringing you into this group as really the main guy running the show. But the group has literally doubled in size since you took over, but people hear both names, right? So, what is the difference between Lifestyle Investor and Tribe of Investors?

Ryan Casey: Yeah. Well, I think that the Tribe of Investors was born at the SoDak Shindig, right?

Justin Donald: That’s right.

Ryan Casey: Where the Erik Van Horn's Franchise Mastermind met the Lifestyle Investor Mastermind at Darcy's garage there. We had a big event. And the essence of it where there are so many people that loved the Lifestyle Investor mastermind. They weren't quite there as far as it didn't make sense for them financially at that point. To backtrack a little bit, Lifestyle Investor is typically made up. We have about a third high-earning W-2s. We have about a third of business owners who are active business owners. And then we have about a third who they've had an exit, whether they've sold the business or they're running it passively, they're out of the day-to-day. We have net worth that range anywhere from a few $3 million to $5 million, but really $3 million, $5 million up to 500 plus, a wide range.

Where Tribe of Investors is more where it doesn't have that third category of people that had the exits. It's closer to 50/50 high earning W-2 or an active business note or running. Most of them, I say, would be a little bit newer to the alternative investment world and in that kind of $1 million to $5 million range.

Justin Donald: For net worth specifically?

Ryan Casey: For net worth. Yeah. One of my favorite sayings is that you should always be at least four years, your education should outpace your financial success by at least four or five years. And the Lifestyle Investor, that's spot on. There's so much stuff that'll help you today. But there's always somebody in the group that's higher up on the ladder than you, whether it's through passive income net worth, whether the knowledge and investing in a specific asset class. There's not just one ladder. There's many different ladders. So, there's all sorts of people that are ahead of you on those different spectrums.

Justin Donald: We’ve got a few people that are going to hit billionaire status probably in the next couple of years in Lifestyle Investor, and obviously, that's not the case for Tribe, but there's always someone ahead of you, right? So, there's always people to learn from.

Ryan Casey: Yeah. And so, in Lifestyle Investor, you might have a session where like that doesn't apply to me today, but now three, four years from now, I know that will be something that's on my radar and that would've never been on my radar if I wasn't in this type of setting.

Justin Donald: That’s right.

Ryan Casey: For Tribe of Investors, it's much more we're all in the same boat, we're all going through this together. So, the education is much more catered to let's make progress now. And then you have, we've already had multiple people that they're in Tribe for a little bit, now they're bumping up to Lifestyle. And so, that's more of Tribe is let's get you to that next level. We're all in the same boat there, and we can dial in the education a little bit more specific. As far as you want to get in like deal flow?

Justin Donald: Yeah. Let's talk about the difference in deal flow and curriculum, and everything, the experiences.

Ryan Casey: Yeah. So, the deals are the same deals. It's not the same amount of deals. So, a Tribe of Investors, they don't get a separate deal where a Lifestyle Investor doesn't see it. All the deals come through Lifestyle Investor. I love how we do calls on Lifestyle Investor, by the way, because that's one of the most educational parts is people come in. We bring the sponsor on. They do their presentation. There's open Q&A. That open Q&A is so educational where people are hearing, "You know what, I would've never thought to ask that question before.” I remember, a year ago, we got into, and it was an industrial deal, and we were talking about the insurance because it was an area that had heavy hail, and if it demolished the roof, what does the insurance cover, and how does that affect the…? Like, really nitty-gritty stuff that gets into that due diligence.

Justin Donald: Because we have members that are experts in insurance or in industrial or in that geography of the world or the US. It's incredible. And then the members are getting smarter and smarter. They have better investment criteria. The questions that they ask, they're learning from everyone else. So, every time we do a session, the questions are that much better to the sponsors. Like, to the point that we've had many sponsors that have said, "Wow, these are the best questions we have ever been asked ever by a group or a community.”

Ryan Casey: Yeah, and I was doing all of the onboarding until recently. And most members, when they come in, they're like, "Well, I don't know much about that. I'm going to be kind of bottom of the totem pole.” And it's funny to see them six and seven months later asking those questions.

Justin Donald: That’s so cool.

Ryan Casey: Those calls are all on the Lifestyle Investor Mastermind. Then what will happen is we will pass about half of the deals to Tribe of Investors, where they'll get the recording. And initially, when I came into Tribe of Investors, I asked, "Well, don't you want to have some of the live calls?” And a lot of them appreciated just the recording because they could learn from people there, or a couple of steps ahead. It had a little bit more repetitions with the types of investments. So, the investments, you do such a great job about negotiating minimums. Like, we get so many minimums, we're at 10% of what their minimum is. Sometimes even less than that.

Justin Donald: That’s right.

Ryan Casey: But we still have some that are a little higher minimum, 150K to 250K. Those ones usually don't go down to Tribe. And then you mentioned how sponsors gave a shout-out to our members of the questions they're asking. Another thing we get shout-outs from sponsors all the time is how nice it is working with our investors. They love our investors.

Justin Donald: Yes. They love our group.

Ryan Casey: Many of the investors are value-add, too. They’re knowledgeable, and sponsors can ask questions, and get great feedback, and help their whole process. So, what we often see is some sponsors will come to us and say, “Hey, we're already oversubscribed. I have a $2 million or $3 million, though, I set aside for your people. Do you want to put it in front of them?” And it's somebody we've worked with before. We like their deals. They've gone through diligence. Usually, Lifestyle Investor mastermind swipes that up, and that doesn't make it down to Tribe. But the rest of it, they get about half the deal flow, but same process. Same due diligence. We spend the same money on it. So, that's been really good. And those deals, along with Lifestyle, have continued to get a little bit more institutional, more diligence on them as well compared to what we're doing three, four years ago.

Justin Donald: Yeah. And what about experiences and even like, I guess, one thing I'll say is Lifestyle Investor has their own retreat. Tribe of Investors has their own retreat. They have access to the live events. That's first-come, first-served, right? Because we will hit capacity. We sell them out every time. And there's only so big that we're able to go or willing to go with the hotels here in Austin.

Ryan Casey: We don't want to run a thousand-person event, you know?

Justin Donald: That's right. But what's an example of, like, a right now Tribe of Investors topic versus a two rungs up Lifestyle Investor topic?

Ryan Casey: One of the big ones, like one of our topics for the retreat will be, for tax strategies, how do we negate W-2 income? That's a huge one that we're really going to dive into a lot there, and that happens in Lifestyle a little bit more. But in Lifestyle, we hear more like PPLI is a great example of that's not something that's usually going to be covered in Tribe of Investors, where Lifestyle Investor, that's something that's on a lot of people's radar, either immediately or in the next few years.

Justin Donald: Yeah, that's good. Let's talk about the Foundations Mastermind. So, we've talked about kind of the two bigger masterminds, Lifestyle Investor and Tribe of Investors. But we've rolled out Lifestyle Investor Foundations, which is our young adults program. And really, just like any of the other masterminds, there are the four ROIs, the four areas that members can get a return on their investment, plus there's a mentorship engine kind of built in. So, Foundations’ evolved a lot this first year. So, what has changed? And why?

Ryan Casey: Well, first let me say that I think the growth of the mastermind for Lifestyle, Tribe, everything, when we get compliments of, “Hey, the improvements are awesome,” almost all the improvements come from members' ideas. And that's one of the things that I've done the most is just create a feedback loop to, “Hey, what do you want to hear, and how can I implement it?” That's what I look at as my main job of because we have so many incredible people. I can't say yes to all the ideas. Most members know that by this point. So, Foundations, what we are hearing is people saying, “Hey, where was this when I was in my twenties? And is there anything for my kids?” So, that's why we created it.

And we had two members of Lifestyle, I think they're on their fourth year, Nick and Molly Pastermack, who are just amazing human beings, that they are very passionate about it. So, they kind of took that on, and I was helping, and we created the mastermind. We launched it last year. Nick and Molly, now, they got invited to go teach at their former university. They're so passionate about teaching the youth, so they're doing that. Nick's still involved. You'll see Molly pop in here and there, but I've kind of taken it over. And what we're involving is more of the mastermind members to come and sit in on some of these guests.

But basically, the four ROIs that we have for all of our masterminds, the connections is one. Well, with the Foundations group, we have people that are in their twenties that are now able to connect to Lifestyle Investor Mastermind people, right? Those are our speakers. They can get a scholarship to attend those live events, or they get, I think, 60% discount to attend the live events, and just that network. We initially thought it was going to be more kind of college age. We both have Cutco background. We're thinking, okay, those types of young adults. And what we found is most of the people joining Foundations are late twenties, early thirties, already making six figures. Some of them already have some good passive income. They have their first rental.

One of them had just bought a business their first year in Foundations, so she came in at like in the process, completed it with the help of Foundations. And Nick, I know played a big role there. And the younger people we're getting are the people that say, “I want to be in a group with those older twenties, early thirties that are business owners, investing in rental properties, have that passive income going.” So, the connection is just massive for that Foundations group.

Justin Donald: Well, I thought it was really cool when we ran our first event. First and foremost, the majority of the first wave of members were all kids of the Lifestyle Investor Mastermind members, right? They've been asking us for years, "Is there a program where we can roll this out to our adult kids?” And so, that's really the genesis for where foundations even began. But I thought it was so cool at the very first live event that we did for Lifestyle Investor Foundations, we had three young individuals, two of which were 18, and one of them was 21, and all three of them had their very first rental property. I mean, just so cool to see. I wish I had gotten a start that early.

Ryan Casey: Yeah. So, we will do calls like Garrett Gunderson's going to be our speaker next month, which will tie in with the third pillar there of tax strategy. But we will have members that'll sit in for some of the discussions so they can share their experience. We also have part of the portal where one of our Foundations members can say, “I'm looking for this type of opportunity.” And that goes into the mastermind section, so they get access to them, and then vice versa, where a mastermind member can say, “Hey, I'm looking for somebody who wants to learn this type of real estate, wants to have some sweat equity, could help me with this, maybe partner on a deal. And they can put that in the Foundations one. And we know these people, too. It's not just putting out to the, that we wouldn't do that in the open group yet, but that's a pretty cool benefit for the Foundations people.

Justin Donald: I love it. Yeah. What are the rest of the ROIs here for Foundations?

Ryan Casey: So, connections is the first one. Education is the second ROI. And for our current members, we say, “Hey, what if every financial decision you made was 1% to 2% better? Talking with people in their twenties, 10% to 50% better. The education has a massive ROI. The tax strategy's another one. The subject Garrett's going to be talking about is 10 to 12 tax strategies that are relevant for that group now. So, imagine saving 5,000, 10,000, 20,000 there. And then, instead of deal flow like the masterminds, it's deal evaluation. They get the $2,000 vetting deals courses in there. We're working on building their investment criteria. We already had one member who has said no to three deals that he said, “I would have said yes otherwise if it wasn't for that investment criteria.”

Now, it's too early to say what's going to happen with those deals, but he was very happy about that decision of saying, "No, there's the JOMO, the joy of missing out, coming out again.” Yeah. So, that's the deal evaluation. We also are building kind of a database of good first potential investments.

Justin Donald: Yeah. And did you mention the 25-year-old that bought a business is actually making 6K a month in passive income?

Ryan Casey: Well, those are two separate. So, we have one person that bought their business. She's doing amazing. But then we have somebody else who's hit a million net worth, $6,000 a month in passive income, 25 years old. They're both 25.

Justin Donald: That's incredible. I just love it.

Ryan Casey: He's actually on next week or this week.

Justin Donald: So, what's a concrete first step a Foundations member can take in month one?

Ryan Casey: What's really cool is one of our first members, Austin Oberbillig, was my former mentee at Cutco. He still lives by me. We kind of met. He loves getting involved in helping. So, he went through all of our recordings the first year, and we've kind of created this roadmap of here are the starting points. So, it’s just diving in and it's kind of ask a question, "Where are you at? Here's where you start.” So, I could spend half an hour on that, but I would just say our roadmap of the first year's worth of content.

Justin Donald: I love it. Well, Austin's done such a great job. I'm so excited to have him really helping lead the charge there in the Foundations’ community. I want to pivot here to the open community, though, because this is kind of the first step, I think, for most listeners, right? So, like, what if someone's, they're listening right now or they're watching this, but they're not ready for a mastermind. Maybe they're not quite ready to make that investment yet, or they don't have the time maybe. Where could they start?

Ryan Casey: So, we have the open community, and we'll post the link for that in there. But really, you can go to lifestyleinvestor.com/invite. And our mission has shifted over the last couple of years. First, we said we want to be the best investment education company. And I wanted to scrap the company. We want to be the best education community. That's what people love about the masterminds. And we get so many people say, “Hey, I read the book, and I went to talk to my neighbor about whole life investing in tax strategy and asset allocation, and they just looked at me like I was nuts. So, where do I go to talk to people about these types of things?” And that's what we created with the open community. It's totally free.

Actually, going back to Foundations, the Foundations event from last year, where we kicked it off, that's all free in the open community. The session we did, The Passive Income Roadmap, has been one of our most popular sessions. We've had great feedback from members. That's free in the open community. Best of whole life. We've had all these little sections that people have covered whole life. It's one of the things we get the most questions about. So, we've taken those sections out and we've made the best of whole life. That's free in the open community.

Justin Donald: So, what isn't in the open community so that expectations are clear? What is a mastermind only thing versus what's an open community thing?

Ryan Casey: Well, rarely are you in there. I think you did a webinar here or there, maybe a couple times a year. So, we do an education call maybe one a month, but you get me as the host instead of Justin, so you get the B team on there. But there are no deals. We don't present any deals. There are always people talking about deals and things, and there's a lot of chatter. But we won't vet a deal. We won't then present it to that main group. Those stay restricted for the mastermind, the tax strategy database, all the member perks. We have so many. We have longevity perks from different groups we work with. All those are reserved for mastermind members.

Justin Donald: Yeah, I think that makes sense. I mean, it's growing at an incredible clip. I think we're going to eclipse 2,000 active participants in the free community, in that open community. It's really exciting.

Ryan Casey: Yep.

Justin Donald: So, why do Lifestyle Investor Mastermind members send their friends there first?

Ryan Casey: Oh, well, that's one of the reasons everything we try to add is first filter is how can we make this a value add for our mastermind members first? And we got so many people where they would say, “I really think my friend would be good for the mastermind. I'm not doing a good job explaining it. Can you jump on a call with them, or can you do this?” And so, what we also want to do is, "Hey, let's create that open community. Our members can invite anybody, and they can kind of get a taste of what we do in the mastermind.” It's the same type of setting. We usually have a lot more people on calls because we have 2,000 people in there versus 100 plus in the mastermind. But we will share the topics, and the mastermind members will say, "Oh, hey friend, they're going to talk about the Big Beautiful Bill or scaling businesses,” and invite people in there.

Justin Donald: I love it. Well, I think we've got to spend some time talking about our biggest new project right now. We're in the process of writing a kids' book. It's almost done, but I want to talk about why that matters to the movement. And you've really championed building the next generation, right? So, help us understand what this kid's book is all about.

Ryan Casey: Well, I was reading a book to my daughter about financial literacy and things. She's eight, turning nine here, actually, at the end of the week. And this is good that she's hearing some of this stuff, and she's interested. She's looking for jobs and how to make money. But I'm like, we could do better. And so, that's been the project that we've really started at the beginning of the year. In the summer, we did a lot of work with it, and we launched it, kind of soft launch at the September event. Told people about it. There's a few changes we're making, but I'm so excited for it.

The journey is basically the Savannah, the main character. She qualified for regionals, needs $2,000 to go, and her parents are like, "No, we're not going to give it to you, but we'll help you show you how to earn it.” And she partners with the other kids, and there's a free parents' guide. There's a workbook with it. But it's a story. It's a story format versus just here are some bullet points on a financial principle.

Justin Donald: Yeah. And think it gives parents a simple way to teach money and investing principles and even scaling business principles early, right? We have the section at the end that's like, “Hey, two different paths. If you're a younger kid, try these things out. If you're an older kid, try these things out.” And so, I think our goal is to really appeal to every level, right? So, you've got Lifestyle Investor at the top, you have Tribe of Investors in the middle, you've got Foundations with the young adults. And now you've got a kid's book that appeals to kids that are 6 to 13-year-old for maybe that younger tier, and then like 14 to 18-year-olds for that older tier, with action steps. It's really a cool thing, and it's been fun authoring a book with you, Ryan, and having characters based on our, you know, the four characters are our four kids, which is so cool.

Ryan Casey: And it's a different financial book that I think a lot of people, there are some lessons people learn in their forties and fifties of the kids that, "Hey, it's not just grinding. Hey, we hit this big goal, but we don't feel great about hitting the goal. What's next?” And it's learning how to appreciate the journey, learning about gratitude, not just about how can I make more money? Some lessons that are Lifestyle Investor principles, not just the investor, but the lifestyle part of it, especially.

Justin Donald: Let's kind of transition here to some common early-stage mistakes. I want to talk about some of the top mistakes that we see, but I also want to talk about how our ecosystem helps prevent those mistakes.

Ryan Casey: When I took over with Foundations group, one of the questions I got was, “Hey, what was your biggest learning thing from Lifestyle Investor that you wish you'd have known when we were our age? And it was creating a personal investment criteria. I think back to my twenties, most of the investments I made, and we did Cutco. I made $40,000 while I was 18, selling knives. We had some money to invest when we were young, but all of my investments came from recommendations of other people. What is my dad investing in? What is my division manager investing in? What are these people? What am I hearing about versus really diving in and learning in that whole like a mile wide inch deep versus an inch wide, a mile deep? If I had had a personal investment criteria, investing in bonds 18 to 20, I would've been in a way different position than I am now financially.

Justin Donald: Totally. It wouldn't be a random portfolio. It'd be an intentional portfolio based on people that have had a high level of success out there and data points of what the ultra wealthy actually do, right? Where they're putting their money,

Ryan Casey: And that's still a mistake that most of our members come in. That's the first thing they're doing is I haven't honed in on my personal investment criteria. So, that's one. Chasing shiny deals is a big one. Paying attention to asset allocation, having a balanced portfolio versus, “Hey, this is working. I'm going to put all my eggs in this one basket,” and then economy changes, and that basket is tipped upside down. Waiting until the end of the year for taxes as opposed to thinking we talk about there's, you know, real tax strategy is thinking multiple years out. What are strategies that you can put in place now, so when three years from now you're not saying, “Hey, how do I reduce this year's?” You already have most of it baked in.

Justin Donald: I love that. I think it's important that we're, throughout the year, going through tax strategies, every quarter kind of digging into that. And I think making sure that we're not investing right out of the gates, that we're pausing for 60 to 90 days. And just kind of wrapping this kind of section up, I think investment criteria first, deals second, right? Don't focus on getting into a deal until your investment criteria is done. And we have a lot of, and I feel like we do, you specifically have a workshop on it, but we do a great job equipping our members there. And you don't have to be a member to be equipped because we do a lot of this in our open community. And then secondly, if you can't write your nos, then you're not ready to say yes, right?

You got to know what you're saying no to. You got to know what you actually want out of a deal. Do you want cash flow? Do you want it to sit long-term? Do you want to get it back as quickly as you can? Do you want to recycle it? What type of risk tolerance? I mean, all these things we've got to figure out.

Ryan Casey: And so much of it just goes back to what are your initial goals. The whole point of investing is to get you in life where you want to be, right? So, you need to start with that.

Justin Donald: And real quick, where does AI fit into all that we're doing, but without losing our human judgment and human aspect of doing things?

Ryan Casey: Where we're trying to use AI is more to just simplify the process and keep it personal. So, like our InvestmentCriteriaGPT, you just don't plug in, “Hey, what should I invest in?” It interviews you, so it's getting you. How do you feel about risk, and how much time you want to spend, and what are your main goals? So, that's how we're kind of structuring our AI is more just to filter through the information than replace your thinking.

Justin Donald: That makes a lot of sense. Well, let's talk about what's next here. For different listeners, what are the next best steps that they can take?

Ryan Casey: I think the first thing is you and I had a big conversation about when the mastermind hit 50 people, did we want to expand? And when it got to a hundred, it was infinitely better. More people answering questions. The Ask for Help section in our circle account is my favorite section because it's a place where now that mastermind is a sounding board for any decision. And so, we've recently talked about do we want to expand past that, a hundred? And we've said, "Yeah, we want to go to more of that 130, 150 range.” So, for the mastermind, that's one of the growth. We're looking to grow that more aggressively than what we have, really ever, in the last couple of years.

The open community, like our big goal now, is to make this Lifestyle Investor movement. We'll have some merch stuff coming out. Tee’s working on that with some hats and shirts, and things like that. But really, how many people can we grow in that Lifestyle Open Community? The kids' book, how many conversations can we start creating at the dinner table with kids and families? And how many parents are going to be like, "Wait, what did you read? Tell me about that chapter. Well, it's a little shift in thinking there.” And how can, "Oh, shoot, this is what my kid's reading. How can I make sure I am setting the example for some of those decisions there?” We just want to keep growing and involving more people in the process.

Justin Donald: I love it. And I just want to challenge everyone listening and everyone watching to really make a decision on one of these four categories. Not all of them involve a financial investment. They'll all involve some sort of a time investment, but there's an opportunity, one, that doesn't cost anything. And then there are, depending on where you're at in life, there's three other tiers, whether it be for young adults, kind of the mid tier with Tribe of Investors, or our flagship offer, which is the Lifestyle Investor Mastermind. But I would just challenge everyone listening and everyone watching, pick one of these four categories, and move forward because it's going to help you take the next step.

And for those of you that think you're ready for the Lifestyle Investor Mastermind, I don't think there's a better place out there to help people build wealth, to help people become better, smarter, sounder in their decision-making, especially around investing, tax strategy, education on a myriad of different things, but then of course, deal flow, and creating passive income. So, Ryan, thanks for joining us. This has been awesome. People can always go to lifestyleinvestor.com to figure out more of what you want. You can go to lifestyleinvestor.com/mastermind, and that's where you can apply.

But I always like ending every episode with a question for our audience. So, in common fashion, what is one step you can take today to move towards financial freedom and really move towards living the life you desire on your terms, so, again, not a life by default, but a life by design? And what's one thing that Ryan and I discussed today that could kind of usher in a new era for you moving into financial freedom? Thanks so much for your time, and we'll catch you next week on our next session.

Ryan Casey: Thanks, Justin. It's been awesome.