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Cameron Herold
Hey, it's Cameron Herald, the host of the Second in Command podcast. Before we dive in, there's something you need to know. If you're a coo, VP Operations, or you're in any role where you're the second in command to the CEO, the COO alliance is the place for you. If you're the integrator to the visionary, you're going to want to join us. The COO alliance is the world's leading community for the second in command. We've had over 500 members like you join from 17 countries to grow their skills, connections and confidence. You'll get the tools, friendships, and a 10x guarantee to ensure that you get your money's worth. Go to cooalliance.com to learn more and see if you qualify. You can even book a free call with our team to ask questions. Now, let's jump into this week's episode.
Ryan Casey
I think two things that really I learned with Cutco is I was a shy kid. So much to the point that when I came home and told my dad, hey, I'm going to go sell knives, still to this day Now, I was 17 when that happened. To this day, I've never seen him laugh so hard because, like on the floor laughing that this shy kid was going to go in people's houses and sell knives.
Cameron Herold
No.
Ryan Casey
But so playing off that, the two things I really learned was one was the personal growth. That was the first time where they really encouraged it. And I saw how there was a direct correlation with the more I grew, the more I made, the more I advance. And that was motivating to me. And so that really got me down that personal growth track.
Cameron Herold
Welcome to the Second in Command podcast produced by the COO alliance and brought to you by its founder, Cameron Herold. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made them the chief behind the chief. And now here's your host, Cameron Herald.
All right, we got a great episode right now. This is actually the CEO of a friend of mine, Justin Donald, from Lifestyle Investor, Our guest today is his coo, Ryan Casey. Ryan is a really solid entrepreneur and a sales expert with a background in leadership and business growth. After earning his bachelor his business management degree from the University of Washington, he spent 22 years at Vector Marketing, which is Cutco. He kind of blew that organization away leading high performance teams and generating over $40 million in sales, which is pretty crazy because when he was 17 years old, his dad laughed at him for even taking a job With Cutco, he then entered the fitness industry, launching two Orange Theory Fitness franchises, ranking the top 10% of over a thousand locations. His Bothell Studio in Washington was named the top performing studio in 2023. He has been the COO for lifestyle investor, which is a financial education company helping entrepreneurs achieve financial freedom through passive income. And under his leadership, the company expanded to three masterminds and growing a free community. He also lives in Seattle with his partner Casey and their three children. He's also a member of John Vrooman's Front Row Dads. You're going to love this episode. You can also share this episode and you can watch it on our Second in Command podcast YouTube channel. We'll see you on the inside. Ryan, welcome to the Second In Command podcast.
Ryan Casey
Thanks for having me. It's great to be here.
Cameron Herold
Looking forward to this for a bunch of reasons. One, you work with a friend of mine, Justin Donald, who is the CEO and the founder of the organization that you guys built, which we'll talk about, Lifestyle Investor. Secondly, because you came out of the Cutco world and I have got way too many ties into the Cutco and vector marketing world with clearly friends like Justin. I was very, very close friends with John Rulin and Brad Wymart was at my wedding. Hal Elrod and I co authored the book the Miracle Morning for Entrepreneurs together. I've been bumping into you guys all.
Ryan Casey
Over the place everywhere.
Cameron Herold
Yeah. So I want to, I want to actually start with that. I want to go back and talk to you a little bit about your experience with vector marketing slash Cutco, and I want you to talk to us about what you learn with them because I've been exceedingly impressed with them and the organization and the people that I've met. So I'm either meeting all the amazing people and they've somehow sheltered me from all the losers, or they just didn't work with any losers. Like, can you talk to me about that company?
Ryan Casey
Yeah. I think two things that really I learned with Cutco is I was a shy kid. So much to the point that when I came home and told my dad that, hey, I'm going to go sell knives, still to this day, Now, I was 17 when that happened. To this day, I've never seen him laugh so hard because, like on the floor laughing, that this shy kid was going to go in people's houses and sell knives. No, but so playing off that, the two things I really learned was one was the personal growth. That was the first time where they really encouraged it. And I Saw how there was a direct correlation with the more I grew, the more I made, the more I advanced. And that was motivating to me. And so that really got me down that personal growth track. And the other thing was really how to start systematizing things is I. I'm not the person who walks into a room and I can just chat with everybody and super charismatic. But you had to learn how to build rapport to do your job. So. So what I learned, how to build rapport is, okay, how do I make this a system? I ask questions. What questions do I ask? I can ask them about the person that recommended. And that's how my brain normally works. I'm good with puzzles, I'm good with patterns and doing those types of things. So I was able to take something where a skill that might come naturally to somebody. How do I break that down to somebody who doesn't have that natural skill set and then teach it? So those were two of the big things I took away.
Cameron Herold
I really love that. I love the whole systemizing. But then I even love that you systemized rapport. I remember when I was doing college pro paint, that I was taught to build rapport as well. Right when you get to the front door of the person's home and they taught us to look for a painting or a picture, anything that would grab your attention and whatever that grabbed your attention, talk about it. It was like a sailboat. Oh, I have a friend who's a sailor or a dog. It's like, oh, my mom has a dog. Whatever it was that you felt you could make that connection about, it was enough. Was that kind of the same idea of what you would look for?
Ryan Casey
We actually had the five Ps, pictures, plants, paintings, people, pets. That was the same stuff. But where can you find commonality? And to me, I always try to find out, how can I do this? We were talking about school and grades earlier, a little bit of, you know, what's good grades? And to me, it was the what's the shortest path to an A? And that was always kind of how I attracted. In retrospect, that's not the best way to do. I should. How do I learn the content the best, right? But for me, it's like, what's the quickest path to rapport? And how can I replicate that? So for me, my question was always, oh, how do you know, Susie? Because every single person had that in common. They were recommended by somebody. So that was one single question that I could start. And once I knew, if I asked One thing I could easily start following up on those. So finding what's the lowest common denominator. What's the easiest path that makes something happen over and over again for me.
Cameron Herold
So I want to talk to you about the lowest common denominator in a second. I love that you said that. Really what you should have done was learn the content. For me, the shortest path to the A. I had a brief affair with one of my teaching assistants and she, she gave me the copy of the law final that was definitely the shortcut to the. But you can't systemize that. Most of the.
Ryan Casey
I was not as dedicated to the A as you are.
Cameron Herold
The only A I ever got. Talk to me about the. The. The. The lowest common denominator. What does that mean to you? And looking for. Is it kind of like the. The basic, easy to implement systems?
Ryan Casey
Yeah. And I don't know if that's the best phrasing but you know, going back to Cutco, we primarily worked with young adults and they were 1099. They're not paid to show up. And most of them didn't come wanting sales. They might have been intimidated by sales. So in order for you to teach a group of people simultaneously and have them be successful, you had to teach. Okay, what can I teach? Where every. It's going to be applicable to everybody. I don't want to lose half my audience because I'm teaching. Here's the absolute best way. And then you're losing half of the group. I can teach. Just because something's good doesn't mean I need to teach it right now. And so what do. What does the whole group need at the moment? What's something I can say that will apply to everybody to get them to the next step and then keep looking at it that way?
Cameron Herold
Yeah, I used to say that to, to write a great system you have to be able to put it on a post it note. And if you can write it down in a post it note, you're thinking clearly. And then I also used to say that we had to. We used to call it Bob Proofing. We had a franchisee in Buffalo whose name was Bob. He was our very first franchisee. And much later on he never would have been awarded a franchise. He didn't have the skills that we then started to require. And he was in a tough market. He was in a blue collar Buffalo where you got a little bit of snow in your background right now. But Buffalo, they'd have eight feet of snow in February. I'm like, what kind of A system would work for Bob in Buffalo with 8ft of snow in February because if Bob can do it, then, you know, somebody in the best market can crush this thing. So I like that you think that way. Cutco also is really famous for referral based sales and they didn't do real door to door marketing. You weren't out knocking on doors as much as you were generating referrals from each person you were talking to. Can you give us a couple of the takeaways there? Because I think you guys are probably the best in the world at generating referrals.
Ryan Casey
Yeah, I mean, one from day one, you know, you depend on and you know, because then the alternative is going back to your initial list which most of our representatives, they, they appreciate that. Okay, I get to practice with some people I know, but eventually I want to move on and feel like I'm, you know, growing my lead base and not have to find another aunt to go find, you know, to show and so that you knew that if I didn't get referrals, that was it. So that was a skill set that was harped on. That was, you know, you know, one of the key pieces that they needed to memorize and get down before they go out. That was the one thing we'd have them memorized before they leave. Initial training, everything else, you know, they're looking out of the manual and stuff. But that thing, I'm like, hey, can you memorize this today? Cause it wasn't that long. And then also I think it just set up the sale that we wanted. Like it all is cohesive. Like, you know, if you're getting recommended, that means they enjoyed your service. It, they enjoyed the process of it. And that's one of the things. I don't know if we'll get into the orange theory stuff, but like now we've kind of reversed that to where how can we have a sales process to where we're generating referrals where before it's like, we know we need to get referrals. I like to think of it both ways. You know, where I want the sales process and not only sell, but if we do it in a way referrals should be easy and should be happening organically. And then also, hey, if I know I'm depending on referrals, how am I going to plug that throughout the sales process? So you're looking at it both ways there.
Cameron Herold
Okay, So I like that they actually kind of socialized it with you and explained why it's important. And it gave, kind of gave you the fear that if you don't figure this stuff out, you're going to kind of be struggling. But teach us, give us the what did you memorize what was. Because I'm sure you still remember it today. What was this? The little. What were the lines that you said in the first phone call? What were the lines you said at the front door? What were the lines that you said when you were sitting with them? What were the lines you said at the end of the sales cycle? Can you kind of give us a couple of little step by step takeaways out of the manual from back then that people can use or learn from?
Ryan Casey
So the first was just on the initial phone call. It's you don't know me, but you know so and so. Oh yeah, they. I was just over talking with them the other day and they thought you might be able to help me out with something I'm doing or it's nothing scary. You were making a little fun. But also just from the first point of interaction, it's. You were recommended to me. This is planting the seed. And then throughout the presentation, I'd always looking for those commonalities. Oh, do you know so and so down the street too? Yeah. I was also recommended to go see her. I was recommended. How many times can I say recommended throughout the thing? So by the time I get to the end, I'm going to ask you for recommendations you already know. Big one I used to teach our reps is during the rapport building part, you want to be Sherlock Holmes where you don't start the presentation until you can already list at least 10 people that you know they can recommend to you. You're looking at Billy's pictures and you're like, oh, so your son plays baseball. How long has he been doing that? Do you guys have like the snacks and the parents all get together afterwards? How long has he been on the same baseball team? I'm like, okay, there's five or ten parents there. You know, how long have you lived in the neighborhood? You guys have a big parties, you do it. And so we. I would teach my reps where you're not starting the demo. So when you get to asking for referrals and they're like, I don't know anybody. You're like, what about the seven people on Billy's baseball team that he's played with for eight years? What about the five neighbors who are always over here? What about the ladies you play pickleball with every Thursday? You know, specific thought builders there.
Cameron Herold
Wow.
Ryan Casey
And it because Half of it is just laziness I make. I told them I'm like, the main reason you're not getting. You know what, the biggest reason why you're not getting a lot of referrals is because the amount of work it takes to pick up the pen and move it back and forth and as opposed to not doing anything. That's really it.
Cameron Herold
Well, no, you just Audrey shucks over the key, which is the Sherlock Holmes component of you were doing the digging to find out the five or ten you were going to talk about later before you started pitching the product. And I think so often salespeople go in with the sole mind of I'm selling the product. Then at the end they try to do some networking for referrals and they don't have anywhere to start. That's really genius, by the way. Like, I actually wrote it down on a post it note to talk to my sales team about Sherlock Holmes first. That's the nugget that I haven't heard from anybody inside of Cutco yet. I mean, I've spent too many hours with too many of you guys. You're the one that gets it right there. So that was. That was a huge nugget. Funny you asked me about, about Orange Theory. I had breakfast two days in a row two weeks ago in Dubai with the former COO of Orange Theory, Griff Long. I don't know if you ever. Did you ever know Griff when he was there back in the day?
Ryan Casey
No, not.
Cameron Herold
He might have been before you or I don't know. But. But he. Anyway, we were having breakfast over in Dubai. Really? Really smart guy. He was on the podcast about five years ago with me, so I'll have to get you his episode. But you were a franchisee for Orange Theory for a couple of years. One of their currently. Oh, you still are. Okay, so walk me through some of those lessons because I think there's going to be some stuff there around systems as well.
Ryan Casey
Yeah. That, you know, we, we bought our franchises in 2015. My parents were my partners. And 2016, we opened our first one. And at that point Orange Theory had a lot of things dialed in. Their sales process, though, was here's a spiral notebook. That's how you track who's coming in and how you keep track of your sales. And God, there's no sales training on there. So that was which I didn't care. I'm like, this is great. I have that Cutco background to put things in. It was a little shock getting used to the W2 stuff at a point. Sometimes it was nice because I can just go higher for positions like I can hire a manager where when you're a cutcoat, you have to start at a bottom rep and you've got to develop them into managers. So there was some differ. It was just overall good experience doing the pre sales. The hard part of the marketing, you know, getting out, doing the door knocking and other ways to drive business. When you're not 100. The nice thing about referrals is, or the tough part about referrals is you only work on referral with the business. It's like, wow, I have all these different ways that we can go try to generate leads. So that was, you know, learning curve and getting creative and getting out of the comfort zone. I was still back in the day where they'd put the orange suit on, you know, and.
Cameron Herold
But have you. Have you lost the art and the kind of skill of generating referrals or do you still incorporate those in OrangeTheory? Have you gotten lazy and just relied on marketing now? I'm curious where your head is around that stuff.
Ryan Casey
You know, that is, that is. I'm more passive in my orange theories where I'm not in there more than a couple times a month. And it's. It's not something we're executing and I feel like we did probably do a. Probably a better job than most, but it's still not something that we're executing at the highest level where there's not that same dependency from the sales team where I have to ask for these, I have to. And it's that point of comfort. But we try to implement the same types of things of can you get the Sherlock Holmes and get a couple people recommended. Usually more around accountability partners and things like that of who could be people that are doing and mentioning recommendations at the beginning, asking on the phone who do you want to bring in for a guest? And then at point of sale, you know, what's in it for them? That's a big point in getting referrals. It's not just, hey, I need referrals, it's why. How does it benefit you to give me a referral? Right, that's how you want to frame it. So it's a, hey, people come here to hit goals. One of the easiest ways to hit goals is have an accountability partner who should be in here working out with you. Write down a couple, we'll give them a free workout so they can try it out. But for that to get executed consistently, it doesn't happen as Much as as we'd like, there's not the same motivators as Cutco. It's all on me, my income, how easy it is going to be for those phone calls. I don't want to sit for five hours calling the same small list over and over. I want to call for 15 minutes because I can cherry pick my very best leads and be done. So I'm very motivated as an independent contractor for cutcode to get the very best leads and as many of them where you front desk person at Orange Theory. If I don't get any leads, it's not as big a deal for me on there. So that, that's a tougher nut to crack for us.
Cameron Herold
That's interesting for sure. I'm going to ask you one more question about your, your kind of Cutco experience before we dive into lifestyle investor and talking about your, you know, working relationship with Jason, the CEO who's also out of the Cutco world, or Justin. Sorry, not Jason. So when your dad laughed at you when you were 17 and you kind of describe it, you laughed as you were saying it, but it must have really hurt. How did you get over that? Or did you use that? Or did you just know that he was laughing but loved you and was going to be there? Like, can you walk us through the mindset and then the growth from that? And do you still, do you still leverage any of that today? You know, when customers or suppliers or banks, you know, say no, it can never happen, do you still dig deep?
Ryan Casey
Yeah. My parents have always been extremely supportive and I knew they would do what they can to help. And they're also great devil's advocates where, you know, I might be hyped on something and say, I don't think this is a good idea. They were fine with it. They're like, go for it. But I'm the weird type of person where I'm much more motivated by a naysayer than encouragement. So I was pissed when he was laughing. Mike, you've been telling me for two weeks to go get a job, finally go get a job, and you're laughing at me. I'm like, all right. And then they didn't think I was going to do well. And like, that's the best thing you can do to motivate me is challenge me and don't, you know, don't believe that I'm going to end. It wasn't. And my parents believe in me. All they sky's the limit. But they just didn't think that was the right fit. They're like, well, you do your best, but I don't know if that's, you know, that's the right thing for you. It was funny after a week, it was back when this is late 90s, where you could call zip code or area code, area code. It would charge long distance. And so I'd always have to check in with my manager. And I'm like, this is going to cost a fortune. I'm like, dad, how about you buy me a cell phone? How about I get a cell phone and that way I can call? And he's like, hey, I'll tell you what. Let me see that promotion list. And it was like, three promotions up with 6,000. He's like, if you hit that, I'll buy you the cell phone. You still have to pay all the charges. And it didn't take me very long, and I knocked that thing out, and it was kind of like, all right, here we go.
Cameron Herold
I love it.
Ryan Casey
It was great.
Cameron Herold
I love that you kind of recognize some of that internal driver. When people say, it'll never happen or I can't do it, that becomes kind of, you're driving fire. So now, all of a sudden, you got a transition going. You're operating the two franchises still, but now you're also the COO for Lifestyle Investor and working with Justin. How did you find out about the opportunity? What was it about the opportunity that intrigued you? And why do you think he said yes to bringing you on board to being a coo?
Ryan Casey
Well, I'll try to go quick, but the backstory is that I left Cutco in January of 2020 because the fitness studios were going good. I have young family. I had young kids. At the moment, I'm like, you know, what, am I making more money from Orange Theory than I am with Cutco? I'm spending more time in Cutco, though. What am I doing that for? So I have kids I want to spend time with. I leave two months later, Covid hit. Gyms are shut down for a year. So now I don't have a job. My businesses are shut. Justin calls me up and says, hey, I'm doing an investor happy hour. There's five of us. We're talking about deals every Friday. So I started on there, and that group, from five to 10 to 15 to 30 people, launched the mastermind. And he said, hey, I could use some help. Can you help me a little? I'm like, I'll help you a little bit, but I don't want to. Don't want to do a lot So I helped him a little bit as a member and I was basically just a member who would help with some of the backend stuff. It just blows up. It gets to the point where it's almost 100 people in the Mastermind. He's managing it with an EA and a thousand Google Docs. He brings in an EOS implementer. They say, you need an implementer. They all said, ryan should be the implementer. And I said, no, I don't want to do it. Like I can get it. I just, I don't want to be working. I left the job. My orange theaters are back up and actually running now I have income. I don't want to do it. And they also happen to be fractional COO roles. So they came in and within two weeks realized that for what we wanted to do is probably to have better. It was probably better to have somebody internally that knew the lifestyle investor ecosystem versus the outside. So I flew down and told Justin, I'm like, okay, I don't want. I want. I love what we're doing. Two years the mastermind had been operating. I love what we do. I don't want it to be messed. Here's the deal. Like we're both in Front row dads as well. So I said, my kids are in school nine to three. That's when I'll work.
Cameron Herold
Yes, I have a group coaching program for CEOs. And the beauty of my group coaching calls is you actually get to ask me questions on every call. You're not just listening to other CEOs. Drop me an email Cameronameron herald.com for more information.
Ryan Casey
I still have to go do my orange theory stuff during that time, you know, a couple times a month here, what do you say? And he said immediately, yes. And that's when I was like, shit, I should ask for more money. But he was on board. And you know, him being front row dads, we totally value family and none of us want to grind. That's not. Wasn't. This is a project that got out of hand. So that was the start. That's how I got the position.
Cameron Herold
Love that. I just had a call last week with John Roman from Front Row Dads, the founder of Front Row Dads. Great guy. So he and I met at a crazy little festival a couple years ago. So lifestyle investor you kind of mentioned to me earlier didn't start as a business. It started more as a passion project as a way to kind of educate some people. Justin, had he written his book, he must have just coming out right yeah.
Ryan Casey
So he started the Mastermind before the book came out. And so he started the happy hour calls in March of 2020 while he was in the process of the book. The Mastermind launched in September of 2020. The book came out in January of 21.
Cameron Herold
Okay. And so when did it turn from the passion project into the business then, do you think?
Ryan Casey
More when I came in. And so, and that's what the job was. You know, he wanted to have more structure around it. He, he, this was supposed to be fun for him. And then he built this job for himself because the Mastermind grew. And, and so that's, that's when he, we said, okay, well how can we. I mean, when I came in, it was still Justin Donald dot com. I'm like, well, let's make it lifestyle investor dot com. And that's one of the first of many small changes we're going to do to build this out as a brand that's not totally dependent on you, although it still really leans on him just because people love him and love his insight. But that's kind of the mission is to slowly remove the company's dependence on him for the company to flourish.
Cameron Herold
Can you speak to that a little bit about the benefits of having kind of the founder led company, the iconic founder, and then when you need to move them out to build either a business that is sellable or a business that is more valuable or a business that can just scale without them. Can you speak a little bit around that?
Ryan Casey
Yeah, I mean, when it's small, it's fun. You know, you get that bent. Obviously it takes a special person to build something out of scratch like that. I mean, many people would wish, hey, I wish my passion project got out of hand and grew into a $6 million business or whatever it is. Right. So it's fun to be along the ride and he's doing things that he really enjoys. And it's fun to be working with people who are doing what they love to do. Right. They're in their zone of genius. They're getting to do those things. But as we start growing and getting detached, then it becomes challenging. That transition period of like, okay, I want you. He's instructing his team to run with this and then all of a sudden we run with like, wait, wait, wait, why don't we do this one? Well, because you told us to run with it. And he didn't tell me to do that at the beginning. That's not how I would have done it. So you get some of that going in Justin has particular tastes about different things and especially like we'll do an event in Austin. Only half the team lives in Austin. So he's like, wait, we should do it at this restaurant or whatever. And so it's tougher to know exactly what they want when they start stepping out. And especially COO or CEO, they're not the COO of systems person. No, they're like, they go off their ideas and stuff. So that's hard to communicate all of that to your team.
Cameron Herold
How have you and Justin decided who's got what roles and responsibilities? How have you kind of delineated where he. What sandbox he's going to play in and which ones you're going to play in?
Ryan Casey
Yeah, it's changed over time. When we first started, I was thinking, you know, well, I'll never be the one who's vetting the guest to come onto the, the mastermind of speakers because I just don't have that financial knowledge that you do. And here I am. That's what I do. I've been doing that for over a year now. And so it started with anything that is in his like the deals, the financial topics he's bringing in, the speakers, they still come from his network like that. As great of an investor Justin is the thing he's the absolute best dad enjoys the most is connecting with people. And so such a great connector. So he still will give everybody but now they kind of. We have more of a system. They're like, okay, here's the queue of people we want on. And he always has veto power of like, hey, I want them on now versus the two or three month wait that we, you know, we're usually scheduling two or three months out. But he's still very involved in the deals. We basically try to put people in the position where that person's the only person that can do that in the organization to the level of expertise that we want. I'm not going to be able to pick the deals we want to the level he can. But I'm at a point now where I can select a better guest because I'm more in tune with the members and what they really want than what he is. So although he can give me the types of guests we want, the people, I'm going to be the one that's selecting them because I know what chatter is going on within the group and what topic will be more appreciated at the moment.
Cameron Herold
Okay, makes. That makes a lot of sense too. So then your day to day right now or let me just go back a Bit Tell us a little bit about the clients that you look for for lifestyle investor. What's that client look like? What was your kind of avatar be for a client? And then can you speak to who your competition might be in this space?
Ryan Casey
Yeah, for the main mastermind we have three types of people we really work with. We have the high earning W2s who don't necessarily want to do their career for another 20 years. Want to have an optionality of maybe after 5 or 6 years I want to change paths and have my income taken care of. We have active business owners who want to exit that business, maybe from selling it or maybe from just putting an operator in place and being able to be more passive. Then we have people who have exited a business and they're really wanting to allocate capital with the same level of expertise that they ran their company at, but they haven't allocated capital for 20 years like they had run their company. And so that's where they come to learn. And so you know, we have net worth range from 3 million to 300 million in the group. So that that's who we generally are working with. What was the second part to that competition?
Cameron Herold
Would it be the Tiger 21s of the world? Is that kind of or is that different?
Ryan Casey
Yeah, you get some tiger 21s that's more localized. So and that's generally 10. I think they might even bumped it up to 20 million. So we have a little lower barrier to entry on some of those than a tiger 21. But you know, we get, you know, go abundance. You have tiger 21, there's a few of them. The thing is, is when you get to that high price point, it might not be a direct competitor, it might just be how much that person's allocating for their personal growth or the groups they're going to be a part of that is ends up being competition. So it might not even be topic related.
Cameron Herold
And yours isn't necessarily CEOs is it? You could have a CEO, you could have a high net worth individual that's a physician or something, is that right?
Ryan Casey
We do get a lot in the medical community. So yeah, there's no specific type of career, no specific type of entrepreneur. It's more the tying factor is everybody wants to buy back their time and they see passive income as a vehicle where hey, if I had all my lifestyle expenses covered, how would that change my life? How would I now interact with my business? How would I make decisions differently for my business? How long would I continue to work in my W2 or what time could I allocate to my family or my passion projects versus the requirements I have.
Cameron Herold
For my career right now and buy back your time. A great book title from Dan Martello is another friend of ours. When you mentioned passive income is the core of lifestyle investor around real estate investing, is any of it related to crypto? Is any related to stocks and related to tax vehicles? Like what's the kind of core of it all?
Ryan Casey
Yeah, we don't have one specific asset class. So initially it started with I read Justin's book I want to invest in the deals and Justin's investing with. But then people came in and that was their investing criteria. If Justin's investing and I want to, that's a terrible investment criteria. So really when I got in, we shifted that away of it's not just investing with Justin. The goal of the mastermind are connections, education, tax strategy. That's where our fastest ROI comes from for our members. And then deal flow and deal flow not in hey, I want to invest. What Justin's investing in deal flow is and we spend $300,000 a year on vetting the deals that we even put in front of the group. So most of our investors aren't going to spend that. So they've already had to jump through some hurdles before they even start their due diligence. But then we're going to teach you how to do due diligence. We're going to teach you how to look at your goals, from your goals, build out your investment criteria and then from your investment criteria figure out what asset allocation makes sense for you. So when you mentioned which investments, we do all of them, right? You know, we have private equity, we have credit funds, we have real estate, we have different subsets of real estate. There's a lot of chatter and we'll have some guests every once in a while come on about active. Like maybe I want to buy my own mobile home park like Justin did or maybe I just want to take the total passive route and invest in a fund and just be totally passive. So we kind of COVID all of that, but we look at the well rounded. How do you build it within a an asset allocation that's going to protect.
Cameron Herold
You and grow and okay, so I like that it's everything. I'm curious on how your fee structure works. Is it just the annual fee that you're getting? Are you putting deals in front of people and you're getting a percentage of the carry, or are you taking equity in deals and then having these people come in with additional money. What's the different revenue streams that you have?
Ryan Casey
So the revenue stream for the Mastermind is one fee and that's it. So we have some courses and other stuff that we get revenue from, but from the Mastermind. We don't make a dollar on anybody's investments and that's really important to us. Justin's been asked many times to create a fund because we eventually we put so many deals forward that most investors aren't going to be invested every deal. So they'd say, Justin, can you just do a fund? And then we can just invest in the Justin Donald fund. And he's never wanted to get close to that because in order to do that you're going to have to have some compensation to make it make sense. And then all of a sudden we're biased in what deals we're putting forward, so we don't do that at all. And even in our sponsorship program we have sponsors that'll help pay for retreats and things. Nobody can buy their way in to pitch a deal. So the sponsors we work with are people who have already previously come into our ecosystem that we really liked and worked with and have passed vetting will offer sponsorship to those specific people versus go chasing dollars for sponsors.
Cameron Herold
Interesting. Yeah, it seems like there's been a big trend around communities putting together these rolling funds and having their kind of members put money into the deal. And it feels to me like there is a conflict of interest. Is that kind of your thoughts around it as well?
Ryan Casey
Yeah, I don't want to bash anything, but it's just the structure is faulty because it leads to different motivations. Like you have Evergreen Fund, you have more people that want to join it. Well, you've already allocated to the certain deal. So now I have this new money that I have to find deals for. So now I might have to open up my buy box of things that I necessarily might not necessarily would have put in the fund originally, but now it's grown so much that I have to allocate for that and I. It's just we don't want to have to deal with any of that. They'll leave that to the professionals of.
Cameron Herold
You know, I'm doing some deals on Angellist right now. I've done about 12 in the last 12 months on, you know, open AI and SpaceX et cetera. But I noticed that the groups that are putting these deals forward are putting in sometimes fairly small amounts into the deal because they're making all their money on the carry. The percentage of money that they raise. So you guys really are just there more advisory and networks and the connections for people instead of. And is it because of a fiduciary issue or is it just. It's just an easier model to stay clean on?
Ryan Casey
Yeah, it's just. That's the, the goal is just to help people with that. Like we're again that Justin didn't start this company to make a ton of money. I mean the company does well but we, we don't. We want to. The main point of Justin doing this was the connections and the people. And if we want to keep that community and those connections right. We have to do right by those people and set it up in a way that's going to benefit them first. And that makes it also going back to referrals and things like that that makes it easier for all of those things.
Cameron Herold
Do you think it makes it easier for you to find clients because you're not putting the deals in front of them that you're going to make money on? They actually really feel like you have their best interest at heart.
Ryan Casey
Oh, and the group category right now, there's always a level of skepticism to begin with. So when you start putting a carry on thing then that, yeah, I feel like that would make it a lot harder and that's not something we want to deal with. I think our appreciate that they know we're not going to be making money off deals we don't like. The money doesn't go through us. We say we give the connections to the vendors and they connect directly with them there. So on one end it makes a little tough to track stuff. It's kind of self reporting when we try to see how much invested in different funds. But we feel it's a lot cleaner that way.
Cameron Herold
I know you said early on that you became a real self driven learner. That that was something that Cutco kind of reinforced for you. Can you speak to some of your growth now over the last few years and what are you focusing on growing currently?
Ryan Casey
Yeah, I mean One thing with 2020, it was, it was a rough spot. I'm in Washington. So Covid was different in Washington than it was in a lot of other places across the country. Especially you see 900 orange theories open in July of 2020. Ours didn't open up till February 21st. So I just kept telling myself, you know what? I want to be able to look back and say, you know what? I wouldn't be here if it wasn't for that Covid year and have here be way better than what it would have without Covid. And I was thinking initially that's probably going to take like five or 10 years, but here I am a couple years later and I feel like I'm in a great spot. And some of the things that I joined Ryan Levesque's coaching program, I'm not an online marketer. I don't know any of that stuff. But you know what? All of those things I learned before I went into the CEO role and now I look back and I'm like, wow, that was so valuable because I know what to do when I'm vetting different marketing vendors and I can have really in depth conversation with our marketing and direct because all these things I learned from that group. So we've always just been staying involved. Justin is so kind with. We were coaching with Michael Hyatt, so I would get to sit in on those calls. And Michael is just brilliant man there. So getting to learn from him. We coach with him for a couple of years. I just recently joined Stu McLaren's mastermind, impact mastermind and so all about seven to eight figure membership group. And most of them are a little different than us. They're, you know, our price point's 55 grand. We have over 100 members. And most of their were more like 70,000, $70 a month price point, but they have 6,000 members. But I love those differences because that's where some of the ideas where you never would have thought of come out and you can mix and mingle them there.
Cameron Herold
Yeah, I almost call it ideas having sex. You take an idea from Stu's group, an idea from Ryan's group, an idea from Michael Hyatt's group, and those three ideas have a little idea, baby. And it's exactly what you're looking for. So something, something you touched on, you know, when you did. And by the way, the, The Orange Theory Coo, his name was Griff Long. He was episode 92 on our Second Command podcast. And I'll actually link it in the show notes. I'll send you a copy of the link in the chat here because you can listen to it later. You might want to listen to his. The learning that you were doing back when you were doing the Ryan Levesque stuff around marketing was probably because you were running Orange Theory. You wanted more marketing expertise. Is that right? Or was it just more random growth? It was like, hey, I just want to go learn this stuff.
Ryan Casey
Random growth. It was, what could I start? I was looking at how to do Facebook ads and then I got A call with Eric Van Horn and he's in the franchise world and he was like, well hey, tell me about your range theories. And I told him where we're at and he's like, how'd you get so many members? I'm like, I just teach our people to sell. So he's like, other franchisees need to hear that. So we did a sales little boot camp and that went well. So I didn't have anything going. I started doing a franchise sales training course during COVID and so then I would. But I had actually started Ryan Levesque stuff before that. So I'm like, oh, here's something I can now apply it to of you know, I'm learning the skills first and then saying okay, now where can I go apply this? And that Sales training came up.
Cameron Herold
Interesting. I've been on Eric's podcast as a guest, I think three times now. He runs a really good, good podcast on the franchising space. So what you're talking about I call just in case learning. I'm going to learn a bunch of stuff just in case I need it in the future. And then I also think about it as something kind of just in time learning. It's like I'm working on this thing, I need to learn this to get better at what I'm working on. Is there anything that you're working on learning right now that is tied to something that you're pro, you know, a project or something you're working on this month or this quarter?
Ryan Casey
I think for us learning how to do the like the marketing launches. So we've never done it, you know, that big build up like Amy Porterfield a launch and so something we're going to be doing this. We're going to revamp our passive income Masterclass. Currently it's $5,000 product but it's a, it's a four year old repurposed zoom meeting at no production value.
Cameron Herold
But the is really good.
Ryan Casey
Yeah, well the people they're willing to drop five grand on it. And it's also one of the reasons why we keep the price. What it is is because if you're paying $100 for it, you might not be the type of person where you're really going to ROI for it. If you're the type of person you're like oh I this sounds great and put you're going to ROI multiple times from it. But we're going to revamp that this year, do a big production value at some of our live events and then move the old topic as bonus content. But we've never done like a big launch thing. So that's one thing. Now the other stuff for me is just, just constant learning from the financial aspect. Like I've learned more in the last five years investing than my whole life. And I was one of the division managers in Cutco, would give the financial talk at the conferences and things, but just crazy. And I always tell our members that you should try to keep your financial education at least four or five years ahead of your success rate. So many people when they get money they're like, okay, now I exited my company, now what do I do with this money? Too late. Yeah, you got to be way ahead of your, you know, if you're on a high growth trajectory, you got to keep your financial education even ahead of that. And I'm sure that applies with all sorts of education. You know, I joined front row dads when I had 12 year old and it was nice to see around the corners as much as possible.
Cameron Herold
Well, I love that you're expanding with doing Amy Porterfield's courses on the product launch is great. Jeff Walker's stuff around the product launch formula is great. So you're doing stuff around content courses, you're doing stuff out of masterminds and then you're learning from within this organization. If you were going to go back and give the let's not go to the 17 year old, let's go to the 21 or 22 year old. Ryan Casey, some advice. What advice would you give the younger you that you know to be true today, but you wish you'd known when you were 21 or 22?
Ryan Casey
You know, I've been the type of person where I don't, I have good friends that I've had for a long time, but I like to stay within my social circle. I've never been the one like, hey, I want to go make new friends. And I did the same thing kind of with networking where within my Cutco circle As a young 20 year old, I knew all the top performers. I roomed with Hal Elrod when we go to conferences, we did. I knew all those guys, right. But I never looked outside of the Cut coaster. And you know, when I joined Cutco, my dad was an elementary school teacher, my mom was a state worker. And when I saw that a division manager in Cutco could make $250,000 a year, if I could ever get to that point, that would be all the money in the world. And when I get to my 30s and you start bumping shoulders with all these other people. It's like, man, they were just in a they had a higher ceiling opportunity. And I often look back and say, what would have happened if my mid-20s, I'd have gone to something that would had a higher ceiling. What would have happened? And now there's a lot of what ifs. But I'm really happy with the skill sets that I developed, the relationships I've built so I wouldn't change anything. But that is one thing that I guess about. So I think to answer your question, it would be to look outside those easy communities and the easy environment of how can I grow my network and learn from people that aren't doing the same thing I'm doing.
Cameron Herold
I love it. Ryan Casey, the COO for Lifestyle Investor thanks very much for sharing with us on the Second In Command podcast.
Ryan Casey
Thanks for having me, Cameron. It's a great time.
Cameron Herold
Really appreciate it.
You've been listening to Second in Command, brought to you by COO alliance founder Cameron Herald. If you enjoyed this episode, please be sure to like, share and subscribe to us on Apple Podcasts, Spotify and their other podcast streaming platforms. For more best practices from industry leading COOs, visit cooalliance. Com.
Second in Command: The Chief Behind the Chief with Cameron Herold
Episode: Ep. 462 - The Lifestyle Investor COO, Ryan Casey
Release Date: April 1, 2025
In Episode 462 of the Second in Command podcast, host Cameron Herold delves into an insightful conversation with Ryan Casey, the Chief Operating Officer (COO) of Lifestyle Investor. Ryan shares his transformative journey from a shy 17-year-old joining Cutco to leading a financial education powerhouse. This detailed summary captures the essence of their discussion, highlighting key lessons, strategies, and personal growth insights.
Ryan Casey begins by recounting his unconventional start with Cutco, a direct sales company, at the tender age of 17. Despite his father's initial laughter at the idea of a shy teenager selling knives door-to-door, Ryan found profound personal growth through the experience.
Ryan Casey [00:44]: "I was a shy kid. So much to the point that when I came home and told my dad, hey, I'm going to go sell knives... I've never seen him laugh so hard because, like on the floor laughing that this shy kid was going to go in people's houses and sell knives."
This experience ignited his passion for personal development and systematizing processes, laying the foundation for his future leadership roles.
Ryan emphasizes two pivotal lessons from his time at Cutco:
Personal Growth: Cutco fostered an environment that encouraged continuous personal development, directly correlating growth with financial success.
Ryan Casey [01:05]: "The more I grew, the more I made, the more I advanced. And that was motivating to me."
Systematizing Rapport: Recognizing his lack of natural charisma, Ryan learned to systematize the art of building rapport, turning a seemingly innate skill into a replicable process.
Ryan Casey [05:30]: "How do I make this a system? I ask questions. What questions do I ask?"
This approach not only enhanced his sales capabilities but also equipped him with scalable techniques applicable in various business contexts.
After a successful 22-year tenure at Cutco, Ryan ventured into the fitness industry, launching two Orange Theory Fitness franchises. His strategic leadership propelled his Bothell Studio in Washington to be recognized as the top-performing studio in 2023, ranking within the top 10% of over a thousand locations.
Cameron Herold [03:15]: "After earning his bachelor his business management degree from the University of Washington... Under his leadership, the company expanded to three masterminds and growing a free community."
This move showcased Ryan's versatility and ability to replicate his success across different industries.
Ryan's transition to the role of COO at Lifestyle Investor was serendipitous. Amid the COVID-19 pandemic, he connected with Justin Donald, the CEO and founder, through an investor happy hour. This collaboration rapidly expanded from a small group to a thriving mastermind community.
Ryan Casey [22:19]: "My kids are in school nine to three. That's when I'll work."
Balancing his responsibilities with Orange Theory, Ryan took on a fractional COO role, focusing on systematizing operations and scaling the mastermind community without compromising his family time.
A significant portion of the discussion revolves around Ryan's expertise in sales, particularly his method of building rapport and generating referrals. Drawing parallels between his experiences at Cutco and Orange Theory, Ryan outlines a systematic approach to sales that emphasizes consistency and scalability.
Ryan Casey [11:27]: "How do you know, Susie? Because every single person had that in common. They were recommended by somebody."
He introduces the concept of the "lowest common denominator" — identifying universal elements that can be leveraged to build connections and foster referrals, ensuring that every interaction is optimized for success.
Ryan elaborates on the importance of referrals in sales, highlighting Cutco's emphasis on referral-based strategies over traditional door-to-door marketing. He underscores the dual approach of integrating referrals into the sales process and ensuring that referrals occur organically.
Ryan Casey [09:23]: "One from day one, you depend on... the key thing that they needed to memorize and get down before they go out."
This strategy not only streamlines lead generation but also enhances the quality and reliability of prospects, fostering a sustainable sales pipeline.
As COO, Ryan plays a pivotal role in structuring Lifestyle Investor's operations. He discusses the challenges of transitioning from a founder-led initiative to a scalable business, emphasizing the need for clear roles and responsibilities.
Ryan Casey [24:29]: "We have to do right by those people and set it up in a way that's going to benefit them first."
Ryan and Justin collaboratively define their roles, with Ryan focusing on operational excellence while Justin leverages his strengths in financial expertise and community building.
Lifestyle Investor caters to a diverse clientele, including high-earning W2 employees, active business owners seeking exits, and individuals looking to allocate capital efficiently post-business ownership. The mastermind group ranges from clients with a net worth of $3 million to $300 million, positioning Lifestyle Investor as a premium financial education platform.
Ryan Casey [27:42]: "We have net worth range from 3 million to 300 million in the group."
The company differentiates itself from competitors like Tiger 21 by offering a slightly lower barrier to entry and a broader asset allocation strategy, encompassing private equity, credit funds, real estate, and more.
Ryan addresses the competitive landscape, noting that while Lifestyle Investor overlaps with groups like Tiger 21, it distinguishes itself through its comprehensive approach and lower entry barriers. The focus remains on holistic financial education rather than narrow investment criteria.
Ryan Casey [28:39]: "We have a little lower barrier to entry on some of those than a tiger 21."
This strategic positioning allows Lifestyle Investor to attract a wider audience while maintaining a high standard of financial guidance and community support.
Lifestyle Investor operates primarily on a single fee structure for its mastermind group, avoiding conflicts of interest that arise from investment-based revenue models. This transparency reinforces trust among members, ensuring that recommendations are unbiased and member-centric.
Ryan Casey [32:02]: "From the Mastermind, we don't make a dollar on anybody's investments and that's really important to us."
Additional revenue streams include courses and sponsorships, carefully vetted to align with the community's values and standards.
Ryan highlights the importance of continuous learning and self-improvement, drawing from various masterminds and coaching programs. This commitment to growth not only enhances his personal expertise but also contributes to the strategic advancement of Lifestyle Investor.
Ryan Casey [35:38]: "We coach with him for a couple of years. I just recently joined Stu McLaren's mastermind, impact mastermind."
By integrating diverse learning methodologies, Ryan ensures that both he and the organization remain at the forefront of industry best practices and innovative strategies.
Reflecting on his career, Ryan advises his younger self to expand his network beyond familiar circles. He emphasizes the value of diversifying connections and seeking mentors outside one's immediate environment to unlock higher ceilings of opportunity.
Ryan Casey [41:32]: "Look outside those easy communities and the easy environment of how can I grow my network and learn from people that aren't doing the same thing I'm doing."
This perspective underscores the importance of continual expansion and adaptability in both personal and professional growth.
Ryan Casey's journey from a shy knife salesman to the COO of a leading financial education firm exemplifies the transformative power of personal development, strategic thinking, and relentless pursuit of growth. His insights on sales, operations, and community building offer invaluable lessons for second-in-command professionals aiming to become the backbone of their organizations. Cameron Herold's engaging dialogue with Ryan provides a blueprint for aspiring leaders to emulate and excel in their respective fields.
Notable Quotes:
This comprehensive summary encapsulates the key themes and insights from Episode 462, providing listeners and non-listeners alike with a clear understanding of Ryan Casey's expertise and the strategic operations behind Lifestyle Investor.