Franchise Scaling Secrets and The ROI of Mastermind Groups with Ryan Casey – EP 158

Interview with Ryan Casey

Brian Preston

Franchise Scaling Secrets and The ROI of Mastermind Groups with Ryan Casey

Today on the podcast, I’m talking with one of my closest friends, Ryan Casey. Once a leading figure at Cutco with an impressive 22-year tenure and $40 million in sales, Ryan has since transitioned to the COO of The Lifestyle Investor business.

On top of that, he has also carved out a niche as a multi-gym franchise owner with Orangetheory Fitness. His studios consistently rank in the top 10% for performance, even amidst a crowded field of 1500+ Orangetheory locations.

After COVID-19 hit, many other Franchise owners expressed needing help training their sales staff. Ryan has since started sharing his methods to help small business owners prepare their salespeople and managers.

In this episode, you’ll learn:

✅ Ryan’s scaling strategies that propelled his Orangetheory gyms to the top, even in the face of Covid.

✅ A deep dive into the real-world financial gains and personal growth opportunities that come from active participation in a mastermind group.

✅ The crucial role that top-tier talent plays in the success and sustainability of any organization.

Featured on This Episode: Ryan Casey

✅ What he does: Ryan Casey is an investor, small business consultant, and is currently the COO of The Lifestyle Investor. Ryan opened an Orangetheory Fitness Studio in Bothell, WA, which finished top 10 in Orangetheory’s history at the time for opening members. He followed that up by opening Orangetheory Fitness Renton Highlands, which reached over 1,000 members in less than nine months. Both studios ranked in the top 20 out of 1500 OTF locations. Ryan lives north of Seattle with his significant other, KC, and their two kids. In his spare time, he enjoys primarily spending time with his kids, but also enjoys being a part of the Front Row Dads organization, Scuba & Free Diving, and traveling with the family.

💬 Words of wisdom:It’s more than the skill set. I think it’s the wiring that is the harder thing to change, to go from a saver to an investor, to go from somebody who is constantly chasing that next thing to like, hey, I don’t need the next thing. My life is great. That’s not going to impact my life – getting more money.” – Ryan Casey

🔎 Where to find Ryan Casey: LinkedIn

Key Takeaways with Ryan Casey

  • Ryan and Justin’s CutCo memories
  • Building a Top 25 Orange Theory gym
  • The true legacy of a Lifestyle Investor
  • There’s no growth without pain
  • Hire A+ Talent and get out of their way
  • Why Ryan’s gym business grew during Covid
  • It takes one good idea to change your life
  • People are the ultimate scaling strategy
  • How TLI members have bought back their time
  • Learning to stop chasing the dollar
  • The power of 1% improvements
  • The future of The Lifestyle Investor
  • Snag a free strategy session with Justin

Ryan Casey on 3 Key Criteria for Joining the Right Mastermind

Free 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

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Ryan Casey Tweetables

“We set a good culture. My parents and I, though, didn’t want to buy a job. And so, I think we do a really good job of hiring great people and then getting out of their way.” Click To Tweet “If every financial decision you made for the rest of your life was just 1% better, what would the return be on that?” - Ryan Casey Click To Tweet


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Read the Full Transcript with Ryan Casey

Justin Donald: What’s up, Ryan? So good to have you on the show.


Ryan Casey: Yeah, it’s good to finally be on here.


Justin Donald: We’ve talked about it for a little bit and how fun it would be to kind of tell our story, how we met and just the dynamic of working together and all the cool stuff you’ve done past the time when you and I worked with the same company. So, yeah, I’m just so excited to share your story and all the cool things that you’re doing in the world and all the ways that you’re impacting the Lifestyle Investor community.


Ryan Casey: Yeah, it’s been a fun ride.


Justin Donald: Well, we met back in 1998 or ‘99. No, it’s 2000. Did we meet in 2000?


Ryan Casey: Yeah, I think we met right before management there.


Justin Donald: Okay. So, we’ve been friends for, I mean, a long time, 23-plus years. So, it’s really fun for me when I think about who are my closest friends, who are the people that I want to do life with, and how can I get them involved in the Lifestyle Investor, especially when they don’t need to be, especially when they’ve got a thriving business like you do and you don’t need the money, but you love what we’re building. So, it’s an honor to have you on the team and acting as our COO and many days of the week as the CEO, probably most days of the week. And so, it’s just fun being able to work together.


Ryan Casey: Yeah, well, it’s been fun being a part of it before it was ever the Lifestyle Investor, that small little happy hour group that I feel very fortunate I was able to be a part of with those guys.


Justin Donald: Well, it’s funny because this was a total passion project and I didn’t have any idea where it was going to go. But I remember, Brad Johnson, our good buddy, was like, “Hey, man, I think you’ve got something here. This thing’s awesome. And I just can’t wait. Every week, I can’t wait until we get together. I look forward to this.”


And so, he’s like, “I think you should make it bigger.” And I was like, “You think?” And I didn’t know where it could go. I just knew I had fun, he had fun, you had fun. And look where we are today. Who would have ever thought that we would be branded as one of the biggest and one of the best masterminds out there of all masterminds? Very cool.


Ryan Casey: It goes to show you two have just kind of your attitude in the group we run with is turning something that’s not so positive because that all happened during COVID and finding the silver lining and hey, what can we do because of this? We’ve created something great out of it.


Justin Donald: Yeah, there’s no doubt. Well, you and I had a chance to work in Cutco together. We paid for college by selling Cutco. We moved into management, we ran offices, we ran divisions, had a lot of people doing things. At one point in time, the corporate company training was modeled on me and my videos, and they came and brought a film crew to record everything that we did from start to finish.


And then it was fun being able to hand that baton over to you as you were the next wave of kind of systematic implementation and really trying to create the SOPs for new managers and even veteran managers. So, that was really neat. And then we both kind of went our own ways after that. And I think it would be fun to talk a little bit about your journey.


Ryan Casey: Yeah, sure. Well, I mean, you were kind of the pioneer. I remember at a meeting and I think you told me, you’re like, “Hey, I might not be here next year.” And I was like, “What? What are you talking about?” You’re at the top of your game. And I knew you had been investing in mobile home parks a little bit and I’d gone for some other stuff, I mean, the whole life insurance and some other strategies we’ve talked about.


But I was so shocked that you were walking away from a great income. But then, I mean, it totally made sense. And that was one of the things where I really got serious about my investing. I was always a good saver, mediocre investor. I just throw out in mutual funds and pick some stocks and yada, yada, the normal stuff.


So, I got serious about, you know what? I really want to find an investment where my skill set can impact the return. And so, I kind of had that thought going. And then one day, I was playing basketball with my brother and he fouled me really hard because he can’t keep up with his older brother. He has to foul, right?


And so, I hurt my shoulder and I hurt it to the point where I couldn’t do a pushup, I couldn’t do anything. And I’ve never liked working out, never liked going to the gym. I’d play sports to stay in shape and I couldn’t do it. So, summertime, put on some weight. And finally, I get the little flier thing that’s Orangetheory, three free workout, whatever. And I’m like, I call him up. I’m like, “Hey, I can’t even do a pushup. Can you work with me?” That guy, “Sure, no problem.”


And I went and it was fun, it was great. I never had something, like workout was planned for you, and coach was there to kind of modify. And our coach was great because she’d say, “No, don’t do that. I know you have a hurt shoulder.” And so, that was really cool. And yeah, I ended up dropping a bunch of weight and loved the workout.


But then the key was I saw them open their second one while there was only one in the state at that time, and I saw them open up their second one and the whole process of it. And that’s what we did with Cutco. It’s like open up an office, train the manager, and manage it through somebody else. I was like, “Oh, this will be like having another office in the division.” And so, they got in, saw how much it was and like, I probably want to bring on partner.


So, I found the best business partners I know which are my parents, and my mom and dad were retired. And we have very complementary skill sets. My mom loves the admin and stuff that would just give me a headache. And my dad, facility maintenance and the buildouts, he was just instrumental in that. And we went on and that was probably the best sale I’ve made. It was convincing them that it was a good idea though. My dad is very risk averse, and opening a business and fitness, oh, he’s like, “I don’t know.”


Justin Donald: Well, it’s nice you get a little one plus one plus one equals five or equals ten, where you just have some economies of scale, some different geniuses and superpowers that combine in a way that is totally aligned. And I love that. I mean, I love when I can have those partnerships that go to the moon because you work well together. You have different skill sets. You totally can run different aspects of the business at a much higher pace than if you were doing all of it. But you’re also more gifted and skilled in certain areas. So, I love that you’re able to do that, and with your parents, I admire that relationship and that cool opportunity. Most people never get a chance to do that.


Ryan Casey: Now, it’s been so cool. There’s so many things after it. I have three little ones. And so, they still come up every other week. We visit each studio, they stay the night. A lot of times I can get date night there. On the night, they stay, and then every third time, we’ll send one of the munchkins home with them and they get some good grandma/papa time. But they’ve had a lot more grandkid time because of the business, which has been something where integrating your lifestyle with your business, it’s been really good. It’s been a good perk.


Justin Donald: Oh, I love it. Well, we talk about Lifestyle Investor all the time, and what does that lifestyle look like? What is ideal? It’s different for everyone. And I love the moves that you’ve made that are important to you and to your family. So, I just think it’s awesome. And I think it’s worth noting that you have two of the top performing, two of the top 25 most profitable studios out of all of Orangetheory Fitness, and we’re talking over 1,300 locations just in the US alone.


So, I mean, like what a lot of people don’t get is that you didn’t ever have to step into the role as COO with Lifestyle Investor. You were making great money. You still are making great money, not counting anything from what our brand pays you, but it’s cool that you got to opt into it. And you tried some other things, too, in the interim when you said, “Okay, well, I’ve kind of got this Orangetheory Fitness thing unlocked. I don’t have to work, but it’d be cool to figure out what is next.” And I’m curious what that process was like for you. And I don’t know if we want to get into the story, but I feel like I had really put some pressure on you to get you in to run it because I knew you’d be amazing, but you were kind of in a time and space in life where you’re like, “Hey, I don’t really need to do anything. I kind of just want to chill.”


Ryan Casey: Well, there is a lot of in and outs of how I was doing because my dad, I mentioned, was very conservative, so we took very little debt for Orangetheories and we paid them off fully before we ever took any distribution. So, that was at the end of 2018. So, I said, “You know what? I want to see how this goes with one full year of working my full time at Cutco and having both of them going. So, let’s see how it goes.”


And 2019 was awesome. I was able to do Cutco, running it through somebody else for the most part. Orangetheories were great. It was a lot of fun. And so, the fall of 2019, I’m like, “I’m going to leave at the end of the year. This is going to be it.” Casey and I, in partnership, we said, “2020 is going to be the year of fun.” We had five or six trips planned out. Our second youngest at the time, he was three or four months old. So, I would be able to travel for free with him. And he’s easy to take on the plane at the time. And then, so in January of 2020, I left my full-time job of 22 years because the fitness studios were going well. And I live in Washington State. And so, we know what happened two months later, and that’s when COVID came. So, it’s like, I didn’t see that one.


Justin Donald: Horrible timing. It literally couldn’t have been worse timing, Ryan.


Ryan Casey: And financially, for 2020, that’s correct. It couldn’t have been any worse financially for that single year. But I knew that, I just kept telling myself that I need to be able to put, I have time freedom now. I don’t have my job this year. The Orangetheories aren’t doing anything. They’re closed for a year. So, I need to make sure I’m using my time the right way.


So, initially, I was thinking, years from now, I’ll be able to look back and say, “Because of COVID, I’m here. And if COVID didn’t happen, I wouldn’t have been at a good place.” And then some stuff was just lucky. I didn’t plan that you were going to start doing the investor happy hour, little calls that you did. I stumbled upon meeting Erik Van Horn, and that’s where I started doing the franchise stuff and then meeting Ryan Levesque in that little happy hour group, saw his online coaching and said, “You know, that’s something I’ve always wanted to learn more about” and gotten involved in his programs.


But it wasn’t always fun because, first, we’re like, “Oh, this is great, a little vacation.” And then COVID kept staying. We’re like, “Wait a second, first round of PPP.” So, we used our first round of PPP to pay our coaches significantly more than what that– remember, they had the federal retention, so they got an extra 600 a week. So, we had to pay them more to where it’s worth not sitting on their couch and we weren’t allowed to take any revenue. So, we paid out our PPP because we were thinking the most important thing for us is to retain our members.


To retain our members, we need to give them some value. So, let’s pay our coaches, do online workouts, and we’ve used almost our entire first round of PPP on this. And we went through about June. And then we’re like, “Oh, my gosh, we don’t have any more money left and we still can’t collect revenue and we have no sign of reopening.”


Justin Donald: And by the way, I should chime in here because to give perspective on how bad it was in the state of Washington and other states, but yours was one of the worst, I own an Orangetheory Fitness studio with some partners and we literally closed down for two months. That’s it. So, our total time closed, I don’t even know if we hit two months, it was right around two months. But you guys were closed for the craziest long amount of time, and I felt so bad for you guys.


Ryan Casey: Yeah. One studio was closed for 358 days. The other studio, we worked some creative spacing. And one, we were able to open for a couple of months in September, and then they closed down everything in November. So, both studios were closed for about a year. And then we were at 1,200 and about 1,170 members going into COVID. When we reopened that March, I think the opening number was 300 members.


Justin Donald: Wow. I mean, it’s a great reminder to do business in the states where they like you, where they have business-friendly laws. I mean, there’s a lot to learn from this. And some of this is like, there’s nothing you could do about it. But for those that are thinking about, hey, I want to start a business, I will tell you that the state you’re in matters, the city that you’re in, the location that you’re in. So, pick your location wisely because it matters probably more than most people realize.


Ryan Casey: Yeah, it was frustrating in July when 900 Orangetheories were open and the West Coast wasn’t, and you saw them, but we made some big moves. And the way we handled it, I think, is what put us back in a position of strength again because not everybody who had those member counts has gone back up to those upper levels. Fitness, in general, it’s been more challenging than it was pre-COVID. But I think because of how our staffs, and I really have to give a lot of credit to our staff, they were amazing in both studios because of how they handled it, that’s what’s brought us back up to those top spots.


Justin Donald: Yeah, I think that’s amazing. And it’s great to see what you’ve been able to accomplish there. And I’m curious like, why do you think you are a standout with Orangetheory Fitness? Why do you think that you have gotten results that are far above the norm and you’ve got retention, you’ve got member counts that are off the charts?


Ryan Casey: Yeah. Yeah, our studio is actually number two in the country, one of the studios, and the population is 40,000. It’s not anything huge. We’re a half hour outside of Seattle. It’s not like a super fancy area, but it’s just a great community. I’d say initially, we did it. We set a good culture. My parents and I, though, we didn’t want to buy a job. And so, I think we do a really good job of hiring great people and then getting out of their way.


We give a lot of autonomy to our managers. When we show up for our meetings, that’s how can we support you? What’s going on? Tell us what’s happening. Okay, what do you need from us versus okay, I need these 17,000 reports and make sure you’re doing that? I trust my managers to use their time wisely because they’re the ones who are in the business day after day. I’m not in there day after day. They know way more about the little intricacies on where they’re spending their time. So, I think that was kind of set the stage.


Also, a sales background, and that’s what I did for a while during COVID, I just started training other franchisees in sales because that’s what I did with Cutco. And when you work with small businesses, nobody goes to work for a yoga studio or a fitness place because they love selling. Most of the people working there hate selling, but they love yoga or fitness or whatever it is. So, just being able to frame sales in the right way. So, it’s like funny because people bring in somebody, they’re like, “I’m going to bring the sales trainer to teach my people how to sell.” And they’re like, “Here, I’m the sales trainer to help you.” And as soon as you say that, they’re already like, “Well, I don’t want to be a salesperson.”


So, we helped a lot of franchisees and all sorts of different industries during that time. But post-COVID, the biggest thing that helped us take off was that most studios were down a third of their member count. So, when they came back out, they say, “You know what? I’m going to offer a third or maybe half of my classes.” Coaches were paid on a sliding scale, so they were saying, “You’re going to make half of what you are making because we have less than half of the member count.”


And we did the opposite. Instead of looking through a financial lens, we said, “What is the most important thing?” The thing that makes boutique fitness tick is member count, recurring members in that community. So, I’m like, “We want retention.” If we want retention, they come for our coaches and our staff. So, instead of offering, even though we had 25% of our member count, we came back with a full 80 classes.


Justin Donald: Wow.


Ryan Casey: Well, today, most studios run 45 to 55 classes. So, we ran 80 classes, which makes no financial sense. But that way, we were able to give the amount of work to all of our coaches, and even we paid our coaches 75% of what they were making when we had full studio and then we gave them a compensation model where as our member count grew, they would get back to that full compensation.


Justin Donald: That’s smart.


Ryan Casey: And now, there’s zero chance we would have been able to afford that either. But if it wasn’t, I mentioned Erik Van Horn, I got involved in his Franchise Mastermind. And this is why I love masterminds is because masterminds, you’re like, “Well, what’s the point of the mastermind and the whole focus? And what’s the structure and all this stuff?” But really, it just takes one little thing. And my one thing was learning about ERC credits when they came out.


So, we had them in real time in 2021. We weren’t paying somebody 20% of the ERC to go get it for us or whatever. Our payroll took care of it. It was a small fee, like less than 100. I don’t think it was even 100 bucks or whatever it was. And that gave us the money to afford to bring back our full staff. So, from March to July, we went from 300 to 700 members in both studios, and then it’s just been up from there.


Justin Donald: Yeah. So, if you look at a return on the investment of that, I mean, that’s like, you’re talking thousands of percent here because it was, what, a tuition fee to get into the mastermind. It only took one concept. And this is what I love about any type of mastermind coaching relationship. I think a lot of people look very linearly at it and don’t look at the bigger picture of it just takes one connection, one person, one mindset shift, one technical/tactical item, one strategy shift. I mean, it just takes one thing, one concept, and that can be the game changer that not only covers the mastermind for that year, but for 10 years.


Ryan Casey: Yep, very much. And the thing is a lot of those keep going, like we have recurring. There’s no way we would have been out our member count. We would be at a lower member count because of that. So, every single month, I’m still profiting from that one decision because that’s what helped us get up there so fast.


Justin Donald: That’s amazing. So, yeah, Erik brings so much value to his community and I’m glad that he was also one of the early people in the Lifestyle Investor. And when I think about the early days of the happy hour with Brad Johnson and Shawn Sparks and you and Hans Box and Dinesh Gauba, Ryan Levesque, I mean, this was the original crew, and we had so much fun. We did so much stuff. And who would have ever thought this thing would blow up and become the juggernaut that it is where we’ve got 135, 140 members and we’re offering about 20 times more stuff every single year? In some instances, every single month, it feels like than what we ever did in the beginning.


And I remember thinking, gosh, I need someone to help me run this. And I know the exact someone because I know all of your strengths, Ryan. I know you so well. We’re friends. But beyond being friends, I’ve seen you in a business setting. I’ve seen your genius as it unfolds in all the operating companies and all the different businesses that you’ve been part of. And so, I knew we had to get you in a position where you could help us scale properly and really bring some clarity to what we were doing, bring clarity to the message to even communicate effectively, like what we have to offer. But it took some arm twisting at first.


Ryan Casey: Yeah, because it was December 2020, you just kicked off the mastermind and I was kind of helping in the background. But December 2020 was dark. It was my last month of my payout from my previous job, so no future revenue on the timeline, no second round of PPP, Washington still not open. I’m like, “I don’t know what I’m going to do next month when the rent checks start coming in.” But luckily, PPP came in, Washington opened, or we got news that we could open, but I didn’t want to take it when I needed it, right? Because I’m like, “I want to be able to do this on my own. I don’t want help with it.” And I wasn’t sure what my responsibilities would be coming back there as well.


Justin Donald: Well, I also kind of wanted to help you out. Like part of it was, I know you don’t have the money coming in that you once had. Why don’t we create a win-win situation where you can really help us out here and get things set up properly, but then I can pay you?


Ryan Casey: Yeah. And I was like, “No, I don’t want. I got this.” I had to prove that I can do it. And that’s why I did the sales training as like, I like helping people, but it was more about something that if I needed to scale, I could, because I wasn’t going to go get a job and say, “Hey, I need a job for five months. And once my Orangetheories are back, I’m piecing out,” right? So, I remember telling you, “No,” I’m like, “No, I’ll help, but I don’t want the full responsibility.” So, it took a little bit more nudging.


Justin Donald: Well, I’m glad that it all worked out. And I think we had an experience where we were kind of figuring out, do we want to bring someone else in? Is that the best move? And then it’s fun because I knew you always wanted to do it. There’s probably a little concern of do I want to entangle friendship and business? Am I going to do as well as I think I can do?


And for me, I’m pretty hands off. I mean, for anyone that’s ever worked with me or anyone that knows me, I’m probably the biggest macro manager. And for someone like you, I think you’re going to thrive in that because there’s no management. I mean, we’re teammates and we plan everything together and it just makes it a lot more fun. And I’m just so glad you’re on the team because our business, this incredible brand, the brand was great from day one because we had the right people. But when we started scaling and having so many people applying, I mean, we couldn’t keep up with the demand on the application side. And early on, I was doing all the interviews, right? I was screening everyone. I was saying no a ton, like I felt bad.


Ryan Casey: You don’t do a good job of saying no either.


Justin Donald: I’m not. I am not.


Ryan Casey: You did for the mastermind, which I know is not something you enjoy, saying no.


Justin Donald: That’s right. But I had to protect the integrity of the community. I wanted to be very careful because there are a lot of communities out there where they accept everyone. And so, when you come in to find value alignment, you got to weed through a lot of people that may not be aligned or may not be at the level or scale that you are hoping for that you’re trying to get to, to find maybe one or two people that really can help you elevate. I wanted to have the opposite. I wanted to have every single person can help anyone else elevate because they’re all playing the life and business and wealth building at an incredibly high level.


But they’re also humble and they’re not flaunting their success, but they’re also curious and hungry and want to grow, like they haven’t arrived. So, that’s important. And to me, having that infrastructure was key, and being able to plug you into the role of kind of running the day to day was everything because we have streamlined so much, we’ve created systems that we didn’t have. I mean, I do feel like in the beginning, we were just kind of flying by the seat of our pants, whereas today, I mean, we’ve got a well-refined machine that’s operating. Thanks to you.


Ryan Casey: Well, I mean, you do such a great job at getting value. It’s hard to keep up with you. I remember at one point, you’re saying, “I don’t know if we’re going to be able to maintain getting enough guests, and our waitlist for people to present to the mastermind goes out months.” So, it’s tough to decide. We don’t want to do 10 calls a month to overwhelm our people. So, it’s opposite problem. That just goes to show for you connecting and how much you just really are always about giving. And that’s why I join.


It’s like, I don’t know if we want to get in to the story that made me finally nudged, but it was, had some consultants in and they’re like, “Well, this is the way we should do it.” And I was like, “Okay.” I wasn’t quite sure and I saw the first couple of weeks. I’m like, “You know, we really need somebody who’s in the mastermind who understands it and really cares for it, who’s going to be kind of making those decisions.” And that was kind of the final straw where I’m like, all right, I cared too much about how the group was run because it had been so impactful for me. The only complaint about the group and I echo that is that it didn’t start earlier because it would have saved me a lot of money on some other investments I got into if I had better deal flow at the time, right?


Justin Donald: Yeah. Yeah, 100%. I mean, it’s interesting because you did have an experience that maybe wasn’t as positive when it comes to learning how to invest. And I don’t know if you want to get into that story, but I think it would be pretty relevant to a lot of our listeners, to those watching us here, too. If you’re not careful with who you’re trusting with investment education, you might end up in a very highly speculative arena that just doesn’t have the returns and a lot of promotion and a lot of fluff that ends up not being reality.


Ryan Casey: Yeah, and I’ll mention it quickly, but primarily because of the lessons that came out of it and how it’s helped us shape our mastermind. But I got involved in an angel group and it’s a successful angel group. It’s an angel group, so you have to be in hundreds of investments to really have the return. And I didn’t have enough capital to invest hundreds of investments as a single investor right there. So, you got into a few things and it was all about learning, but it was angel. So, they did what most angel investments did. And I still have a couple in play and most of them have fizzled out within four years.


And so, with your book and I should have just been talking with you more, but knowing those, I would have done things totally differently as far as the amount of capital I was allocating for that. And I love how we, when we do invest in something angel or venture, the way we’re able to diversify and de-risk with some of the funds that we work with is incredible. But what it got me thinking about is that group, even though it was in person, I wasn’t really connected to anybody. I still have a couple of people I talked to, but I was one of the younger people in the group and there just wasn’t that same connection where that curiosity you meant, everybody kind of knew stuff and there was kind of the clicks, the ROI definitely wasn’t there. I lost money on those ones.


And then impact, and the impact was good. I learned from my mistakes, but the impact came from making mistakes in the group, not from the lessons of the group. And I did learn some good stuff on evaluating and things. But it really just shows you, with our group, we’ve really taken those things of you did such a good job from day one, the right people, the right community. You would never guess our members are worth, what some of them are worth when you were just talking on the phone. No, there’s no dumb questions being able to ask questions and help other people and give. So giving, some of them were more than giving with their time. They probably should protect even more.


And then ROI, you’ve done a great job with that. And I think that was one of the pivots when I came in, as so many people had come in in the group. But then when we really looked at it, you and I were saying, “Hey, after hearing all these stories where people are really making the biggest ROI, were the connections from the group?” I mean, we had so many people exit company. It was last year with 23 people exit.


Justin Donald: 23, yeah.


Ryan Casey: And for them to be able to network and how it’s structured and here’s how the PE company is going to come in as 11th hour and do all those stuff and to be ready for that, I mean some of those people were saving seven figures just from being able to network with some of those other people. We’ve had people that have acquired businesses, we’ve had people that have started businesses together, people that have started businesses with some of our strategic partners that will pay off in 10 multiples of what the mastermind fee was, right?


Justin Donald: Yeah, 100%.


Ryan Casey: And then the other ROI we’ve got into is the tax strategy one.


Justin Donald: That’s right. And by the way, one of the things I think would be really fun to do, we’ve talked about this a lot, which is what is the criteria that you want for a mastermind? There’s certain criteria that is important when considering what mastermind to join. And by the way, I’m a believer that everyone should find a mastermind to get involved in. There are different levels, there are different tiers, there are different niches, but I think everyone should have a peer group and a community that is playing the game of life at the level or above the level of where they want to be and then have the opportunity for you as you grow and get better, to be able to mentor those that are coming in that are newer.


And so, when I think about masterminds in general and this isn’t for the Lifestyle Investor Mastermind, I’m thinking the criteria that I want to see because for me, I’ve joined, I mean, I’m part of eight different communities, mastermind communities or groups. And I love each of them for the things that I think that they’re great at. But one of the things that I realized is it’s hard to find everything I’m looking for in one group. And so, I wanted to get clarity on what that looks like and try and find that group. And I could never find it.


And so, part of the impetus in starting the Lifestyle Investor was that these criteria were so important to me that since it’s not out there, I’ll just create it and will see if it attracts the people that I think it could attract, right? So, if we’re talking, so why don’t we get into some of the criteria that we’ve discussed as being, like the three key criteria?


Ryan Casey: Well, I think too many people look at just the topic, right? I want help with my business. Where is the business mastermind? So, that’s the one I’m going to get into, and what you’ve mentioned are the difference. What really makes the mastermind are the people. So, that’s challenging to find out on just an interview. So, knowing somebody who is in, getting recommended by somebody else, getting to talk to members before you can get in, those are all great ones.


But the people in the community are generally where the value comes. It makes me think of, we hit 50 members and we said, “Should we go to 100?” And we said, “Yeah, let’s do it.” And when we went to 100, it was infinitely better because there was more smart, amazing people and there’s more people engaging because the mastermind was never just about you. You do a great job facilitating and bringing in guests and introducing people. But it’s not just the Justin Show. There’s so many amazing, smart people. But you did a great job curating from the beginning, and because you did that at the beginning, now it’s kind of self-perpetuating. It keeps attracting the right type of people.


Justin Donald: Well, the collective genius of the group is far smarter than any single person, way smarter than me. I mean, yeah, it’s funny. Sometimes people join thinking they want to learn from me and realize really fast that this group, that they want to learn from everyone in their area of expertise because everyone has been very successful at a high level in some industry space or niche.


Ryan Casey: Yeah, it’s fun, fun highlighting all the different members and sitting down and having that conversation. There’s some genius that you don’t know immediately. And when you sit down and talk with them like, “Oh my gosh, this person’s brilliant.” I’ve been able to sit down. First time you get to explore some of these conversations.


Justin Donald: That’s right. So, the right people, the right community is kind of like that first criteria. What about the second criteria?


Ryan Casey: I would say, a clear path to ROI.


Justin Donald: And when you say ROI, just a return on investment.


Ryan Casey: Yeah. We want to see how your money’s coming back. Now, that can be different. We’re both in Front Row Dads. I love that. That’s not a monetary ROI, although we’ve partnered with a lot of different people because it’s nice doing business with people who have those same values.


Justin Donald: That’s right.


Ryan Casey: And that’s what I knew. And we had that conversation of like, “Okay, I will come on but only because I’m working during these hours as those were all the kids at school.” I knew that something you would appreciate because you’re in Front Row Dads and have that. But most people invest in a mastermind because they want to better themselves and there should have some type of return. I want to get my business here. I want to get my finances there. I want to get, whatever it might be. So, I think a clear path in understanding where it’s laid out before, right? You know, there’s multiple ways. Okay, here’s how it’s going to happen.


Justin Donald: Yep, 100%.


Ryan Casey: That makes it easy because it’s an investment.


Justin Donald: And some of that return on investment is growing yourself to the capacity that you can make these moves, right? So, it’s investing in yourself, investing in the education, in the relationships, in taking the time to learn what everyone does and maybe how their superpowers can combine with yours. So, yeah, there is a monetary ROI that I think is important to focus on. I also think that there’s a business ROI that we can group in there and say, “Hey, that’s important to focus on.” But I think the ROI on the return, on you, your education, your level of understanding, complex topics, I think that’s huge.


Ryan Casey: Yeah, I think you could almost make that the third one is just the impact, like the non monetary impact of, in our group specifically, I think of buying time back seems to be a common thing. We have hiring W-2s. We have business owners that are in the business that want to get outside of the business. We have people that have exited businesses, but the common theme is kind of buying that time back, and now, what they’re able to do with that time. We have people that are being across the country and people who have left their W-2 and people that have sold the business are now working a fraction of the hours that they were working before.


Justin Donald: Yeah, I mean, they’re truly lifestyle investors. They have bought their time back. And it is so cool to see. I mean, I do think that impact piece is really important. So, from that criteria, obviously, people and community that stands on its own, having a return on investment. And by the way, sometimes that return on investment could be one year that is worth 10, 15, 20 years. I mean, we got one of our members that said, “Oh, yeah, this is worth a lifetime membership because of what I got on this one nugget,” right? So, it doesn’t have to be as linear where it’s like, well, I put in X dollars, and now I’ve made X dollars plus whatever else.


Ryan Casey: I did a few interviews. I still do one here and there, but we’d have people that are like, “Well, if I got to make that back on the return on my first year.” And I’m like, “This is probably not the right fit.” You’re not going to make one investment in cash flow. First of all, the investment is longer than one year. But it’s having that longer term thinking bigger impact or the people that were interested in the group.


Justin Donald: That’s right. And for me, I had financial freedom once and that was one of the most rewarding feelings that I ever had. But it only happens once, like you achieve, I mean, I guess in theory, you could lose it and do it all over again. I hope that never happens, but I know I have the skill set to do it. But when I think about it, it’s like I celebrated that. That was really a special time, but it wasn’t long until I was ready for what was next.


And what I love on the impact piece is watching people regularly have and find and create financial freedom in their lives. And you get to see the impact because you know their families, you know their spouse because their spouse is involved, you know their kids. We’ve got a bunch of people that have brought their kids to several of our events, which is really cool. So, yeah, it’s super rewarding. And I do think that that impact piece is important.


And I also think that for most people, it’s really easy to make money, right? The different amount may vary, but you can find a job, you can make money. I think from there, most people are not very good at managing money, right? You are a great saver. That’s like foundational, number one level. You got to be good at saving money. But most people are not good at saving. They’re not good at investing, right?


And then you have a very small percentage of people that are good at multiplying money. And I think that’s where people, once they get that foundational skill of managing money, saving money, allocating towards different things, then multiplying, that’s where you get around people that are really good at it and play it at a higher level. And then, that next level is making money count. So, there’s a certain point where we don’t need more consumerism, we need to help the groups, the organizations, the less privileged, those that are fighting for freedoms that not everyone out that they should have, that they don’t have, right?


And so, all those to me kind of roll under that impact. And finding the right program for you, I think really matters. What group, what community has the criteria in the value set that is the most important to you that’s going to resonate at a high level, right?


Ryan Casey: Well, you mentioned those skill sets of investing, but it’s more than the skill set. I think it’s the wiring that is the harder thing to change, to go from a saver to an investor, to go from somebody who is constantly chasing that next thing to like, hey, I don’t need the next thing. My life is great. That’s not going to impact my life getting more money. But there’s another way I can impact.


And I feel like you have to be around the right people to change the wiring, just learning this. You can’t just go learn investing, right? And then all of a sudden, now you’re a good investor. There is some mental shifts about learning investing and that wiring. And it’s much easier to do when you’re around people that think that different way that you want to be thinking.


Justin Donald: Yeah. Well, you’ve done a good job of bringing clarity to kind of the value prop of the Lifestyle Investor Mastermind. And I’d love to hear even some of the big changes that have happened from last year to this year because it looks completely different in a very positive way because of all the things that have been added to the community for features and for benefits and perks and whatnot. So, I’d love to hear you talk a little bit about what’s changed, what has been upgraded.


Ryan Casey: Yeah, sure. So, I mean, we talked about the happy hour that we did, and that was all based on deals that we’d look over pitch decks and then we’d review the deals. And then pretty soon, we had. Should I start over on that? Yeah. Well, it all started with the deals. Okay , So, when we’ve gone back to the happy hour, the mastermind started by doing deal review, right? So, we would look at deals, and eventually, we had the deal sponsors on. So, a lot of the first mastermind members were there because deals were the the main driver. And then we’ve had very few people not renew, especially in the first couple of years there. And so, I talked to a few of those people. What happened is they were just there for the deals when they allocated their money, then they stopped paying attention.


I’m like, “Oh, my gosh, there’s so much other stuff going on.” And so, I wanted to make sure people are really aware because the people that, like we mentioned earlier, having the impacts, we’re in different areas besides the deal. Now, we had people that were growing their passive income through the deals, which was great. It’s still a part of the ROI. But we mentioned the connections is the first one.


The education alone, how many people I’ve talked to have read your book and say, “Oh, I think about things differently now when I look about investing”? But when they’re engaged into the mastermind for a year, it will change the way they make every financial decision for the rest of their life. So, you think of what’s the compounding effect, if every financial decision you made for the rest of your life was just 1% better, what would the return be on that? Whether it’s saving money, making money, investing money, it’s a financial decision. They’re learning that.


The tax one was big. You’ve done a great job of surrounding us with some great experts, many who’ve been on the podcast. But when you’re a member coming in, there’s just tax strategy here, here, here. So, we made this tax strategy tracker. Now, it’s up to 50 strategies. And it was great because the first time we had it, we had Jeff Soha on and I said, “Hey, here’s the new deal. I know you’ve been on before, but here’s our list. You need to cover something that is not on the list yet.” And he sent back. He’s like, “You guys have every, like, how am I supposed to do this?” But we made him work and we had another 10 strategies on there.


And so, now, when a new member comes in, we’re like, “Okay, here’s, we get their goals.” We are talking about goals, investment criteria, and asset allocations. We have so many members that come in and they’re so excited about the deals. They’re like, “I haven’t seen this and that before.” And we’re like, “Whoa, whoa, whoa, whoa. Slow your roll. What’s your goal, first of all? Let’s get that investment criteria up so you’re not making emotional decisions.” And then really looking at what’s your allocation now. How do you really think about the world over the next five, ten years? And you bring in a lot of great assets and a good economist and state-of-the-market speakers to say, “Where do I want my asset allocation to be?”


Now, all of a sudden, that cuts through all the noise and it makes it a lot easier to make those decisions. But it’s great to bounce those off with other people. And then, finally, I guess the fourth ROI is the deal flow. So, connections, education which is a long-term tax strategy, which is nice because it hits that dopamine. You can get it within 12 months there and then the deal flow. So, those are the ROIs that we really focus on with our new members there.


Justin Donald: Yeah, I love that. And I think it’s important. Most people don’t have an investment criteria, so they don’t have a list of why they should or shouldn’t invest in things and they make emotional decisions, as you mentioned. I think most people haven’t even figured out what their goals are. They’re just maybe doing what other people are doing or copying other people. And I think it’s important to get clarity on what’s important to you. What would be an epic life for you? And what does that look like? What does that include? And how does that break down on a monthly basis? And how do we figure out how to get to financial freedom based on your monthly costs to live the lifestyle you have today and lifestyle that you want to live, right?


And from the standpoint of asset allocation, it’s so funny. People come in and they join and they have no clue what their asset allocation is. And so, it’s funny when we’re like, “Well, what do you want it to be?” And they’re like, “Well, I don’t know because I don’t even know what it is.” So, we’ve got to help them figure out what it looks like. Most people are so lopsided, they’re so heavy in one area and it’s not well balanced.


But I think if you look at the wealthiest people in the world and I look at data all the time from the wealthiest families, the family offices that run all the financial aspects, wealth creation for billionaires and centimillionaires, all the wealthiest people, and it shows clear as day that they are well diversified across a bunch of different asset classes. So, most people think that the majority of wealth is created in the stock market. It’s actually not. And most wealthy people really only have between 15% and 25% of their net worth in public equities and another 25% in real estate and 25% in private equity and 25% in everything else. And how that breaks down between cash and, I guess, cash and cash equivalents and fixed income and private credit and all the different things. But I think it’s important to address and assess those things. And most people don’t even take the time to do it. So, that’s like move one. Foundationally, we’ve got to figure out where we are and where we want to go. So, I love that.


Ryan Casey: Yeah. And it’s different than just looking at a report because anybody can either pull up a report or pay for some of those reports you share. But a retail investor is not a Harvard endowment fund, right? So, it’s not just looking about where things are allocated, but why and the thought process and then how does it apply to you because you’re going to be a little different. Like, your personal asset allocation, I know what it is. It doesn’t match those, but it matches your skill set and it matches the whys of all of those other big institutions, right?


Justin Donald: That’s right. That’s right. And what else? Are there other things, differences, perks in the newest year of the mastermind?


Ryan Casey: Well, we started in 2020. So, everybody was sitting home at a laptop, and we did an event kind of by accident in 2022 and everybody loved it, just one day. We have our annual retreat, which is Epic, and that’s coming up in December. I missed the first one because we had the birth of our third child just a few weeks earlier. So, last year was one of the first times I’d met a lot of the members in person. So, it was so much fun. And everybody’s there. But we’re like, “We need to do this more often.” So, we’re like, “We’ll do quarterly meet-ups.” And we’re talking now in October, I think we’ve had nine of them.


Justin Donald: That’s right.


Ryan Casey: So, with two more days scheduled this month, so we’ll probably hit well over a dozen and that doesn’t count the informal ones where any time somebody flies in Austin, they’re like, “Hey, I’ll be in Austin for this weekend.” All of a sudden, there’s 12 people at a dinner because we have so many people there in that Texas Triangle. It’s awesome.


Justin Donald: Yeah, I love that. And some people will come in and they’ll do a self-study, whereas other people kind of want to get involved in all the live events, all the live things that we do. But it’s fun because we now have over 500 hours of content in our learning library, which is fun. And people can kind of research the topics that they want to learn and and get great at that. And I love forming partnerships with other groups, too. We’ve got a bunch of big names that we’ve done some cool partnerships with, some on the health side doing discounts.


Ryan Casey: That is free bloodwork this year. That’s one of the longevity clinics that we have, really excited about the software or the financial software that is not going to be cheap. But because we’re early, we’ve been able to negotiate it free for all of our members, which is very exciting. The free trust analysis with some of our advisors there. People love the group, so they’re willing to give a lot for the group, which is nice. We have some great connections now.


Some of the other things we’ve added there, we just filmed our tax course, which I’m really excited because one of the reasons why we’re doing this podcast and I’m excited about future member podcast because not everybody is going to be in the mastermind. It’s not going to happen that way. We’re capping it anyways.


But there’s so much value that happens in there that we want to be able to share more. So, I’m excited for your member podcast that will come up. I think of Ryan Williamson, the testimonial he just wrote, it’d be great to get him on there, but some of the courses we’re doing where almost anybody can do it. So, you want that piece of Lifestyle Investor tax strategy that’s coming out soon. Whether or not you’re in the mastermind, you’d be able to get that, more live events. We’re working on some Justin AI so you can talk with Justin and we can feed all the sources from all the wisdom, both an internal one for the mastermind and a public facing one. So, we have a lot of cool things in the works.


Justin Donald: Yeah, I love just the idea of grabbing hold of AI and using that to fine-tune and strengthen what is already a really fun and cool experience and program here within our community. So, that’s going to be a lot of fun, and obviously, do more of the trips, more of the assessments that we’ve built.


Ryan Casey: Quiz is coming out.


Justin Donald: Yeah, talk about that. That’s going to be awesome.


Ryan Casey: It’s an investor blind spot quiz, but basically, just the quiz itself is very educational. What will happen when you look at kind of the multiple choice? We get into tax strategy, we get the asset allocation, deal flow. A lot of the first two or three answers, you’re probably where you’re going to say, “Yeah, I’m one of these three things and you’ll see.” Then there’ll be another option.


And a lot of people say, “I didn’t even know that is a thing. I didn’t know that that was an option for tax strategy or whatever it is.” And so, just actually going through the quiz is very educational, and then it kind of pinpoints, hey, here’s where, and then we have free resources, they get sent out. So, that’s all free. The quiz funnel will be coming out.


Justin Donald: That’s fine. Yeah, we’ve got a bunch of free event, free content. In fact, one of the cool things that we just did recently, we’ve, for the first time ever, run a non-member Lifestyle Investor live event. That was really cool. We brought in Garrett Gunderson and Codie Sanchez and a handful of other people, but just friends of the community, people that speak often to our community about buying businesses or about growing wealth or about utilizing life insurance in unique ways. And so, I loved how that event went. And I think because of the success of the event and really the feedback that we got from those that joined, that we’re going to be doing another one of those and maybe we end up doing that once a year.


Ryan Casey: Yeah, well, we have to plan it, you and me, here. There was so much positive feedback. We’ll have to do another, at least one next year for sure. It was nice keeping it small, though. It wasn’t like 1,000 people on it. We had 35, 40 people, like perfect-sized groups. So, I think we’ll do something maybe a little bit bigger, but I don’t want to have it, hundreds and hundreds of people.


Justin Donald: I agree. Yeah, I like capping everything we do. I think that that’s powerful for the community, have events that everyone can attend, have some events that are smaller so that way people get to know each other. It doesn’t feel so big for some of the one-day experiences and some of the overnight stuff. And then I’m also excited just to keep our group small enough that everyone, even nonmembers, if we do another one of these events, that they get to know each other well by the end of it. That’s awesome. Well, this has been a ton of fun. Any last thoughts that you have that you want to share?


Ryan Casey: Yeah, I would encourage you, if you’re in the podcast, look at some of the other stuff. We actually have a different mastermind that I’m stepping in and helping run there. Final thoughts? If you’re a podcast listener, I’d definitely take advantage of the free strategy session one because it’s free, but you’ll just hear about everything that we have because we have free options, we have free content for doing those. Then there are some courses, and then a lot of people know the Lifestyle Investor Mastermind. There’s another mastermind that’s a different tier price level that Justin twisted my other arm, and now, I’m jumping in and helping out with that one. But it’s a little bit lower price tier that a lot of exciting things are going to be happening in that mastermind as well.


Justin Donald: Yeah, Tribe of Investors. We had so many applicants that they’re great people, they just weren’t the right fit for Lifestyle Investor yet. In time, they likely can be and we hope that they graduate to it. But we saw the demand was there and thought it’d be really cool to kind of roll a new one out. And this one has taken off as well. So really, really fun. Where can people go for a free strategy session?


Ryan Casey:


Justin Donald: Wonderful. Well, I hope that you’ve had some fun tuning in with Ryan and I today. Ryan, it’s always a pleasure to hang. It’s always so much fun connecting and talking about life, talking about business, talking about just the journey that we’ve had together. And I love working with you. It’s so effortless. So, I just want to thank you for all that you’re doing publicly. We would not be where we are without you and without your creative ideas, your innovative ideas. And I’m excited for the future because we’ve got a lot in store, I mean, a ton of stuff we did not share. But I’m really looking forward to those that are the right fit and find this to be a community that is right for them.


So, for everyone tuning in, I love wrapping up every week the same way that I do. I’ve got a question. This question to me is important because as the Japanese Kaizen mantra or saying goes, it’s this idea of taking one step forward or getting one degree better or just finding a way to have any sort of improvement from one day to the next. And so, I love closing out every podcast episode that we do, asking one simple question of you, what is one step that you can take today to move towards financial freedom and living the life that you truly desire on your terms, so not by default, but rather by design? Thanks, and we’ll catch you next week.


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