Accelerating Growth with Tax-Free Profits and Investing in Relationships with Scott Ryan – EP 104

Interview with Scott Ryan

Will Duffy - Roths for the Rich

Accelerating Growth with Tax-Free Profits and Investing in Relationships with Scott Ryan

Today, I’m speaking with Scott Ryan. Scott is the Managing Partner for Terra Rossa Investments, which is an active investor in fixed income, debt products, real estate, blockchain, VC, and later-stage tech. Scott oversees deal origination, due diligence, acquisition, and liquidity for the company. Additionally, he is the fundraising manager for Lotus Domaine Fund 3.

In this episode, Scott shares his early beginnings as an entrepreneur, going from making 6-figures as a tennis coach to starting, scaling, and selling 3 tech-based companies—one of which landed him an 8-figure exit! 

In our discussion, you’ll learn the biggest investing mistakes Scott made after his big exit (and how to avoid them), the power of relationships, and the strategies Scott leverages to earn more, while avoiding long-term capital gains tax.

Featured on This Episode: Scott Ryan

✅ What he does: Scott Ryan currently serves as Managing Partner in Terra Rossa’s family office. Terra Rossa is an active investor in fixed income, debt products, real estate, VC, and later-stage tech through our Lotus Domaine Fund 3. Scott oversees deal origination, due diligence, acquisition, and liquidity for Terra Rossa. Additionally, he oversees Lotus Fund 3’s fundraising manager to raise the necessary capital. Specifically, he works with entrepreneurs and innovators with proven world-changing products and technologies that – when scaled – can be more profitable and have a significant impact on some of the biggest challenges we face. As a partner in Terra Rossa and a GP in the Lotus Fund, he works with these respective teams to put innovation back into the hands of the lower middle market, later-stage enterprise software companies. Before his work with Terra Rossa, Scott founded, built, and sold several tech-based companies for more than 25 years, and his expertise is forging partnerships and business strategies to accelerate growth in innovative and disruptive technologies.

💬 Words of wisdom: I think money is a byproduct of working hard and getting in front of the right people and always trying to better yourself” – Scott Ryan

🔎 Where to find Scott Ryan: LinkedIn

Key Takeaways with Scott Ryan

  • Why Scott pushed through his comfort zone from a young age and how that helped him earn six-figures teaching tennis to IBM, Lockheed Martin, and Motorola and later do business with Richard Branson.
  • How he went from working in his brother’s company to starting his own business and landing an 8-figure exit.
  • Learn how Scott made success inevitable by networking with people that eventually became his mentors and partners.
  • Scott’s strategy on buying companies with between $5 and $10 million in revenues that allows him to pay fewer taxes and avoid long-term capital gains tax.
  • Money doesn’t buy happiness. Learn why Scott schedules time for activities that fulfill him and does them with people that he loves.

Scott Ryan | Focusing on Health, Wealth, & Relationships as a Lifestyle Investor

Scott Ryan Tweetables

“How you do anything is how you do everything.” - Scott Ryan Click To Tweet “At the end of the day, no one on their tombstone says, I wish I’d worked another day or made X number of dollars more. So, I think that work-life balance between health, wealth, and relationships is key.” - Scott Ryan Click To Tweet


Rate & Review The Lifestyle Investor Podcast

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

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

Connect with Justin Donald

Get the Lifestyle Investor Book!

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

Read the Full Transcript with Scott Ryan

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


Scott Ryan: Thanks so much for having me, Justin. I really appreciate it.


Justin Donald: This is cool. We’ve been talking about this for a while and we almost did this recording when we were in Europe last. And in fact, we should probably talk about this epic trip. You and I have done our fair amount of traveling. We’ve done the BVIs which is cool, a little bit of Necker Island hanging out there, get in time with Richard Branson. And most recently, we went to Monaco for the F1 race, specifically in Monte Carlo, the capital, which is just an unbelievable city. So much cool stuff going on there.


And the race was incredible, like three days of cool experiences, each one different. And if you think about that and you think about how amazing that is in itself, and then on the back end of that, we did a week in Bordeaux. So, I mean, it was just a one-two punch. What were your thoughts? I mean, was that pretty epic of a trip for you, too?


Scott Ryan: Yeah, it was. And I think it’s something that we planned for about six months. We had Mario, who is kind of a well-known sommelier, who put that trip together. And he really went first class. I mean, it was one of the more experiential trips I’ve been on in something that I went in knowing nothing.


I think in Days of Thunder, they said, I’ve never raced a car, but I’ve watched it on TV. That’s kind of where I was. I just see Formula 1 on Netflix. I had no experience about Formula 1 and go to Monaco for your first Formula 1 race, like go to Wimbledon for your first tennis match. I mean, it’s a big deal. And so, it blew away my expectations. And that’s a big statement because my expectations were high.


But we were staying at Le Meridien, as you know, all the racers were staying there. LeBron James was walking around there. I mean, it was the most surreal experience. And then the race itself was pretty amazing. The guy who was supposed to win in the lead, Paul Ricard, I think his name is. He was supposed to win the race. His team brought him into the pits when his other teammate was in the pit. So, he ended up coming in fourth place, which just that mistake never happens. And he’s a native of Monte Carlo. So, it was a big upset, but really amazing time. And it was epic.


And then we flew private to Bordeaux. I mean, it was just like, I don’t know how it gets better than that. I mean, I go for it. I want to split those trips up because there was quite a bit of drinking over an eight or nine-day period. We felt obligated in Bordeaux to keep going. But what a great experience. Yeah, that’s up there with my very best trips in my life.


Justin Donald: Yeah, I would agree. And I just thought it was really cool. Not only did I get a chance to meet Carlos Sainz, who is one of the great Ferrari racers. And by the way, if you haven’t watched the Netflix episode, anyone listening or watching this, if you haven’t watched the F1, the Formula 1 Netflix series, it’s incredible. And that really kind of got me into stuff. And I really believe that has been one of the greatest single causes of the re-emergence of Formula 1.


And I’m not a race car guy. The show is just awesome. So, it was cool meeting him, he was at the hotel. And then another cool thing is LeBron James coming through. And I remember we were trying to lure him over to hang out with us because we know he loves Bordeaux and we’re like LeBron, we’ve got some extra Bordeaux with your name written all over it. And it was pretty cool watching him kind of head out. He went right by us and went to the dock because we had one of the docks that people use to go out to the yachts. So, that was a pretty neat experience too, wasn’t it?


Scott Ryan: That was amazing. I mean, it was second to none. We really did it, first class.


Justin Donald: And what also is cool about F1 is like we did these different locations, right? So, like for the practice, we were at the Roscoe’s turn which was so cool. So, you get to see the cars up close, but they slowed down considerably on that turn and then they ramped up right after. So, you get to see them coming in fast, slowing down, and then speeding up again. I mean, a lot of people say it’s like where the best action is.


And then day two where we got to watch the qualifiers, we were on the yachts. And so, there are these huge yacht parties, and we’re talking– I’d never seen this. I never even knew this was a thing. I knew that there were $100 million yachts, or in some cases, hundreds of millions of dollars in a yacht. We saw billion-dollar yachts. It’s been confirmed. I read a magazine article after it. And several things that confirm that there were several billion-dollar yachts. I mean, that is just absurd, right?


Scott Ryan: And they’re all there for that race. They really are.


Justin Donald: And then for the actual race, we are right above the start line. I mean, you couldn’t get better. Like our one, two, three punch was just epic. And I think anyone would be totally satisfied with a trip like that. But flying and the gorgeous plane that we took, what was that? A falcon. We fly in a falcon over there?


Scott Ryan: Yeah, it was like the Falcon 50, I think it was. Yeah. So, I’m not super up on planes. But the other thing I was just going to mention about the race and that third day when we were in the terrace, what was it called? The terrace is like Siena Terrace, whatever it was. Shanghai Terrace.


Justin Donald: Shanghai, that’s it.


Scott Ryan: Shanghai Terrace where we saw Michael Schumacher, Jr., wrecked and his car split in half right in front of us. It’s unbelievable. So, yeah, it was incredible. That was an incredible experience. And so was Bordeaux, I mean, and you’re a wine guy. We looked at all the first growths. There was Margaux, Lafite, Chateau d’Yquem, I mean, it’s crazy because the way those guys live and the vintners, the lunches that we had, it was just really amazing. I felt like an aristocrat. You know what I mean?


Justin Donald: Totally. Yeah. I mean, we went to the first gross. We went to Chateau Lafite Rothschild, Chateau Mouton Rothschild. I mean, those two were just exquisite. And then to finish the trip at Chateau d’Yquem with their president, the guy who’s running everything, who technically runs Chateau Cheval Blanc was so cool and he’s down to earth, interesting. He just hung out with the prince of Monaco right before us. And we got so much of his time. It was like a three, three-and-a-half hour meal. So, we did a tasting, and then on top of that, we did the meal with pairings. And he got into the library of the old stuff, which was really cool.


Scott Ryan: Something like an ‘83 Chateau d’Yquem. It’s crazy.


Justin Donald: Right. And their chef is a 3 Michelin star chef that cooks out of Chateau d’Yquem and it’s just absolutely life-changing for anyone that is a wine lover and connoisseur like we are. And I know that that was high on your list because this is, I mean, we’re talking about the wine that like Thomas Jefferson and George Washington drank. There’s so much history. You’re a history guy. Weren’t you a history major like…


Scott Ryan: That’s right. University of Texas, a history major.


Justin Donald: There’s so much history in this chateau, like the greatest chateaus in the world or wineries. In France, they call them chateaux. And Chateau d’Yquem is the only Grand Cru Superieur. It’s like the first gross, it’s like the high– it’s the only chateau that has its own level or category of ranking.


Scott Ryan: Well, Justin, I thought it was also amazing. Each barrel has 300 bottles of wine. You run the numbers and you’re like, this is one vintage. One year is $200 million. And it’s really hard to process that. And these companies, I mean, they’ve been in business for 200, 300, 400 years. I mean, 300 years, 400 years, it’s hard to really think about how long that’s been going on, and they’ve been generating that kind of revenue for that much time. So, yeah, it was impressive. It was a history lesson for sure.


Justin Donald: Yeah. I mean, we were looking in some of the cellars, and by the way, some of their library of stuff is like they have wine back in the 1800s in their library, which is so cool. But just when you look at the barrels and you see what’s there, I mean, we’re talking about hundreds of millions of dollars of wine just sitting in these chateaux.


And then it’s like year after year after year after year, you create this reputation. And in France, it’s different because Napoleon basically said, hey, these are the most impressive first growths. They basically said these four are the originals, and then Chateau Mouton Rothschild kind of squeezed in there in the 70s. So, there are five that kind of– they just are now forever going to be like the greatest wines. But what’s cool is finding the wineries or the chateaux right next to them instead of them being like $1,000 to $2,000, in some cases $5,000 a bottle, you can get the chateau right next to it where it’s maybe $100, $150 a bottle.


Scott Ryan: We got those, too. Remember Lynch-Bages? And we drank some amazing wine. That was a great experience.


Justin Donald: Yeah, Chateau…


Scott Ryan: I don’t know if I would do it on the heels of Monte Carlo, where we were drinking champagne all day every day. Yeah, it was a lot of fun.


Justin Donald: Yeah, Chateau Pichon Comtesse, which is right next to Chateau Latour, and then Chateau Giscours, I thought was incredible out there, and Margaux. So, just epic. For any of you wine lovers, get to Bordeaux. Just an epic trip.


So, let’s get to talking a little bit more about you, Scott. You’ve had a lot of success. You’ve worked in a lot of different places. You’ve got a lot of expertise. I’d love to kind of hear your story, like how you got to where you are today. Obviously, you went to school at the University of Texas. I definitely want to dig into why you chose to move to Puerto Rico, but let’s hold on to that. Let’s hear your story and then dig into some of the specifics there and…


Scott Ryan: Yeah, so real fast, I was a history major at UT that prepares you for virtually nothing. I had a minor in economics at Spanish. No, I moved right into sales, but I’ve considered myself sort of a lifetime learner and try to identify problems to solve because that’s where I think you can add the most value.


And so, even in high school, I spent two years in a tennis school, a place called Nick Bollettieri Tennis Academy. So, I was kind of an entrepreneur at a young age. I remember my brother Chris calling me, saying, “Hey, I was playing with Agassi and Jim Courier, and all these guys.” He’s like, “Are you going to be a professional tennis player?” I was like, “Absolutely not, but I think we can make a bunch of money teaching tennis.”


Both Chris and I went– he’s two years older than me. We went to the University of Texas and we taught to IBM, Lockheed Martin, Motorola. And we made, between the two of us, six figures over summer, real money in 1980, $7. So, we were able to pay for school that way. And that was a lot more rewarding than if we had been on the tennis team.


At Bollettieri’s, I figured out there was a way to teach 10 people on a tennis court, generate real income. And I’ve kind of followed that my whole career. When I was in college, I moved to Spain and I studied at the University of Salamanca, and then I moved to Barcelona and got a job there. I stayed there for a year and a half, generate income, and just put myself in. Just like Bollettieri, it’s very uncomfortable situations and pushing to try to do better a little bit each day.


And then also, I met amazing people at Bollettieri’s and in Spain who became mentors of mine because I had to seek out my own mentors. And as you know, we basically vacationed on Necker Island before. I consider Branson a mentor of mine. I raised some money for Virgin Unite. I’ve been blessed to go there seven, eight times. I’ve been to Ulusaba, his place in South Africa.


And so, just really, I’ve been able to meet some incredible people. And as you know, it’s not just meeting Richard. It’s meeting all the people on the island that become confidants and comrades and mentors because most of them are more successful and experienced than I am.


But when I graduated UT, I became a tech guy by trade. My first company, basically, I worked at was my brother’s company, and I went out and started my own thing. I’ve had three exits, I guess, four, three of them good. And my third one was my biggest one. And it was an eight-figure exit, June of 2016.


And then I started investing. And I’m about halfway through your lifestyle investor, maybe a little more than halfway. And I was that guy, I was the 60/40 split guy, load up my 401(k), just go, go, go, and very little experience in investing, especially in private equity which was troublesome because when I sold my third company, I had some money and I started investing with some of the guys in Tiger 21. My brother was heading up some of the groups. That’s how you and I met.


And I didn’t do very well. I bet big on smaller deals. I didn’t have a strategy. I would do a cash flow, monthly cash flow deal, but I was mostly doing equity, kind of playing the long ball, and I wasn’t negotiating any kind of bonuses or sidecar deals, like you talk about or you using investment moneys from insurance or other investments to pay for investments. I just wasn’t doing that. I was making bets, like you talk about lending people money at 0% interest and I hope in a prayer that I’ll get some back in five years.


So, I made a bunch of mistakes and I decided to go get my securities licenses. So, I went and studied for that. I have no math skills, so that was real work for me. And so, I ended up passing, thank God, about three of them, that I needed to raise capital in the private equity space. And that’s kind of what I started doing, really more looking for deals. But when I would uncover a deal, I would bring other people to the table.


So, I created kind of a placement agency. And one of the deals I bet big on, and I lost a couple of million bucks actually in an income deal. So, again, I learned that, number one, I need a strategy. And what I also learned by dealing with a number of ultra-high net worth people, I found out a lot of family offices and ultra-high net worth folks had access to deals that I didn’t have access to.


So, they had access to certain asset classes that I didn’t have access to. The minimums might have been too high or whatever the case is. But they also had access to folks in the know that could identify good management teams. So, I started really sort of investing with some of those folks that I considered quite a bit smarter than me. And that’s really what led me to where I am today.


I met a guy named Christian Mack, who’s my business partner now, but when I met him, he had kind of an institutional-grade fund, million dollar minimum. They had done really well, fund one and fund two. We can talk a little bit more about that. But I met him, and it started to check all the boxes.


I’m a tech guy by trade. He’s got a tech fund. It’s not VC. It’s later stage so it’s a growth fund, but it’s smaller than traditional private equity. So, it’s these hip pocket deals that family offices, by and large, get to see. And I saw that deal and I was like, I think I can raise money for you.


So, we started our journey. We met in a mastermind, similar to the one you run, a different mastermind. We met in one and we started talking, and they had raised about $20 million from their GP, which is a big investment of $150 million fund. They’d gotten $12 million from fund two to roll over and they were trying to raise money. They had just exited fund two in December of 2020, had like a 2.5 exit, got a 36.5 net return. And I wanted to invest in fund three. And that’s how him and I started working together.


Justin Donald: That’s cool. What an awesome story. And by the way, for anyone watching and listening to this, I have done an interview with Scott’s partner, Christian Mack, so check that one out. And then I’ve also done an interview with Scott’s brother, Chris Ryan. So check that episode out as well. So really cool, really fun.


So, you had mentioned family office, and anytime someone mentions a family office, I feel like it’s really good to kind of define what that is. Everyone kind of defines it a little differently, but it’s all generally the same idea. But how would you define a family office? For those listening, they’re like, what does that mean?


Scott Ryan: Yeah. So, family offices, when you get to a certain amount of wealth, I mean, I look at it as a math problem, right? So, let’s say you’re paying a registered investment advisor, an RIA, let’s say you give them 10 million bucks and they’re going to manage your money, they’re going to charge you 1%. You’re going to pay about 100 grand.


So, let’s say you get up to $100 million. Now, you’re paying them a million bucks a year. And so, at a million dollars, you start looking at maybe it’s time for me to look at a family office. Now, a family office, you’re going to have a couple of analysts. You may have four or five employees that are doing deal origination, underwriting, different analysis, but it’s going to probably cost you close to $1.5, maybe $2 million.


So, I think right when you hit about $150 to $200 million, when you’ve got that much money to manage, that’s when people typically go into the family office space. And all an RIA is a multifamily office, it’s a family office with multiple clients. So, that’s when you’re going to dedicate a team just to you when you’re about $200, $250 million. Some people do it at a lot higher number. Some people do it at a smaller number. It just really depends on what you’re comfortable with, but that’s when the economics seem to work out.


The family offices, Christian, my business partner, has his own family office. He had a big exit, as you know, a nine-figure exit in 2012, launched his family office in 2014, and he’s buddies with 90 other family offices. He created a portal, so they share deal flow. And he was the tech guy. So, consequently, that’s when he finally was like, I might as well just start a fund and have these guys invest in one because they’re running all their tech deals by me. So, that’s the premise. But that’s really what a family office is, and normally, it’s an ultra-high net worth person at like $250 million or above.


Justin Donald: Yeah. And so, you kind of have these different tiers, right? So, you’ve got, at the highest level, it’s a single-family office. It’s your own. They just manage your money. It’s your employees, and that’s their job. Every day, they show up and they manage your money.


And then you talked about a multifamily office. You talked about an RIA as an example of that. There are other organizations or other family offices that are dedicated to several members, several clients. So, it’s a multifamily office. So, instead of you footing the bill at a million to two million bucks, you’re splitting it with five, six, seven families, making it a lot more affordable. So, maybe you’re able to get into it for like $300,000 a year or something like that.


And then there are some groups that kind of do fractional family office type of things where you’re paying considerably less, but it’s not a full-blown shop, like when you hear a family office and you think of all the services that they provide. And basically, a family office generally is just going to provide everything that you need from an investment standpoint. Sometimes they’re going to have CPAs in-house, sometimes they’re going to have just people that can basically run anything that you need to run. They might have legal in-house.


Some people want to have all that under one roof versus kind of outsourcing and having a bunch of different vendors or points of contact. And then also, if you do have all those points of contact, a lot of the better family offices will quarterback that so they will be in contact with the attorney, with the CPA, with any other attorneys that may be involved. And there’s a…


Scott Ryan: Yeah, it’s not unusual for family offices to engage multiple wealth managers in multiple different groups. I mean, that’s not unusual at all. So, it’s really what works best for you, but typically, that family office comes in at about $100 million to a quarter billion. If you’re going to do a single-family office, that’s going to start to make good business sense.


Justin Donald: Yep. Very cool. So, let’s talk about some of the other strategies you have on tax saving because I know you moved to Puerto Rico for a reason. At one point, you were living in Texas, right? You were going to the University of Texas in Austin here, where I live. And then…


Scott Ryan: I launched my companies in Dallas. So, I had exits in Dallas. I still have property there. I moved to Puerto Rico. So, when I hooked up with the Lotus guys, Lotus were a fund three, as I said. They do some interesting tax strategies. We have an 8% prep that’s in corporate dividends, so it’s long-term capital gains. It turns out in Puerto Rico, if you’re here for 183 days a year, you pay zero capital gains.


I generate quite a bit of my income with discretionary bonuses by hitting targets, milestones, and whatnot. So, I’m an earner in that regard. Well, in Puerto Rico, you spend 183 days a year, you pay 4% income tax. So, it’s really strong. I mean, the only thing I know better than that, you can go to the Caymans and places like that, a 0%, or Singapore or whatnot. But then you have to denounce your US citizenship. And I wasn’t ready, I wasn’t interested in doing that.


This is really the best deal where you’re still in America, I’m on the Eastern Time zone, which is fantastic. Our headquarters, we’ve moved from Newport Beach to Austin, Texas. And one of the things we do when we buy companies, we buy under what’s called a QSBS model. So, we buy under what’s called qualified small business stock. It’s a structure where, if you buy companies less than $50 million in revenue, we’re normally buying $5 to $10 million. You buy less than $50 million, you hold for five years. There are no long-term capital gains. So, some great tax strategies around what we do at Lotus, like the 4% income for me is the real winner. And that’s great.


And the other thing I’ll share with you, a lot of people don’t know this, is if you start– at the University of Puerto Rico, a super strong school from a financial analyst perspective, from a software development perspective. So, there are plans for us to build a Puerto Rico office here. And what happens is the government will subsidize employees’ income by 30%, so they’ll get a 30% rebate. And the Puerto Ricans, the natives that stay here and work for an American company, they also pay 4% income tax. So, they get the benefit of our tax so we can get a fantastic supplemented office here in Puerto Rico that can benefit Lotus.


Justin Donald: Yeah, that’s cool. And I heard you say that you’re moving your headquarters to Austin, which I’m thrilled about. In fact, you’re looking at buying a place in Austin. And I just had the opportunity to meet the developer and take a look, walk the property on your behalf, take some pictures, some videos, make sure that it checks out. They’re not trying to overcharge, and it’s in a brand-new building, I mean, literally, it’s in downtown and it’s one of the coolest locations. They just completed it.


So, like, literally as we’re speaking, 100% of the units have been sold and the first move-ins are moving in right now as we’re talking. And what a cool spot. I’m excited to have you as a neighbor because this is literally four minutes from my house.


Scott Ryan: Yeah. And this was a strategic move for us. I mean, obviously, you are the number one reason we were coming there, Justin. But from a Lotus perspective, there’s a group called the Capital Factory that I know you’re very aware of down there. And we have a business advisory services group that supports Lotus called Trellis. We just hired a guy named Brett Paulson. And you’ll hear that on the podcast.


But Brett’s one of the big mentors at Capital Factory. Capital Factory’s invested in 500 to 600 businesses. They’re an incubator that becomes a channel for us for deal origination and acquisitions. So, that’s really key. And we’re within walking distance to the Capital Factory and we’ve signed a lease where we’ve got office space there. So, we’re super excited about that.


And I got to say, I’ve raised a lot of money out of Austin, Texas. And I think the reason is, is there’s a really strong financial services background in that town. People understand that space, they understand tech, they understand software as a service. It’s a really unique model. And the Capital Factory fits our mold because those deals are hip pocket deals. So, these are deals that haven’t been picked over by the West Coast and the East Coast. So, they’re right in our wheelhouse, and we can get a really good value from an acquisition perspective. So, we’re super excited about it. And the apartment’s cool, too.


Justin Donald: Oh, I love it. Well, this is going to be a lot of fun. I’m sure there are going to be a lot of parties and hangouts to be had. I know that I was talking with Mario Matavesco, the sommelier of Terra Rossa, who’s already doing some fun wine events here, which is great. I got a chance to participate in a couple of his wine events here. And for those of you that are listening, that are like, hey, I’d love to learn more about that.


For our Lifestyle Investor Mastermind, we’re figuring out a time and a space to be able to do something like this. And for some of my friends just here locally in Austin, where we’re going to do just literally an epic wine tasting with wine that’s off the charts, that’s hard to get. I mean, in some cases, virtually impossible to get. So, that’s going to be a lot of fun. And I know you’re going to be involved in many of these things. So cool.


So, moving forward, I think there are some mantras that you live life by, some words of wisdom that you’ve picked up, and maybe just a cadence that you walk through life with. I’d love to hear kind of your backdrop and your thoughts on just health, wealth, relationships, the most important things that for you make your world go round.


Scott Ryan: Yeah, well, I think one of the things I’ve struggled with in life is the life-work balance. And that’s something that, with this opportunity with Lotus, I was 85% traveled before I moved to Puerto Rico. So, I’ve been to the Middle East four times. I was in Bahrain. In Saudi, I was in Jeddah, Riyadh, Dammam. In the UAE, I was in Abu Dhabi and Dubai, just got back from Muscat, Oman. So, those are taxing trips because you’re talking about 15 hours. I was flying from Dallas direct on Emirates. It’s a 15-hour ride. And it takes you a couple of days to sort of acclimate.


So, I try to move every day. If it’s in a hotel gym, that’s okay. If it’s a heavy walk in the morning or something like that, but I try to move every day, and that’s been important. It’s really hard to focus on nutrition when you’re traveling, so that’s just something that box doesn’t get checked very well because you’re eating local fare, whatever the case is, and you’re entertaining. So, that’s challenging.


But I think I’m doing okay in the health space. I invest a lot of money in the wealth space. And when I say, wealth, I’m talking about wealth of knowledge, wealth of experiences, in addition to those trips that I went on. Like with my brother Chris, we find Kilimanjaro when I was in my 30s. And every decade I try to do something really uncomfortable and a little bit epic to sort of push my comfort zone.


And I think it really helps because the people you meet on those trips can change your life. I mean, from a knowledge perspective, I’m sort of a voracious reader, I should say Audible guy because I try to consolidate my exercise and I’m in the middle of Lifestyle Investor right now. Also, I think I recommended to you Gap and Gain by Dan Sullivan, which I love. I’m a history major.


Justin Donald: Great book.


Scott Ryan: It’s a great book. I’m a history major, and so, I love David McCullough stuff, like 1776, John Adams, Brooklyn Bridge. Those are great. But I’ll also mix it up, like I like Scott Galloway. I like the Algebra of Happiness. I did Post Corona. I’ve got a drift in my library right now, which is latest, which I think should be strong. There’s one I recommend, History of Sketch Comedy with Keegan-Michael Key, which is a cool one. If I’m looking for something light, I’ll listen to that. But I also like, I don’t know if you know Peter Zeihan, the futurist.


Justin Donald: Oh, yeah.


Scott Ryan: Yeah. The End of the World Is Just The Beginning. He’s got it really interesting. It’s about a 30-minute podcast on the next five years. I don’t know if you’ve seen that, but…


Justin Donald: I have, yeah.


Scott Ryan: It’s very contrarian. And he’s sort of this Socratic thinker on how he throws down what I think is the opposite of what a lot of people are talking about, but it’s spot on. So, I like that as a history major, I think history to me is the psychology and philosophy of how people are going to behave in the future, typically. But I think, like we talked about, that’s wealth to me. And I think money is a byproduct of working hard and get in front of the right people and always trying to better yourself.


And after wealth and help, I think relationships is probably the most important thing. And by the way, if you don’t fill the health bucket, you’ll blow up your wealth and your relationships because you won’t be able to participate. And so, I think relationships, although it comes last on my list of stuff, it’s equally as important, just sort of from that tripod.


And for me, relationships, my brother and I talk about this thing called The Last Chat, and you can look at the last chat is, what’s the last conversation you’re having with your best buddy on your deathbed or what’s the conversation that your two closest friends have after you passed? And you want to check the box. Was I a good person, like deep down when no one’s looking? Was I a good person? Did I have good relationships, really strong relationships with people? And did I love and was I loved by others?


And if you can check those three boxes, I think that’s really where you’ve made it and you’ve made a difference on the planet. Those are kind of lofty goals and what have you, but they’re top of mind for me from a mantra perspective. So, when I’m making decisions, am I hanging out with the right people? Are these good people for me to be spending time with? And am I going to benefit them? Are they going to benefit me? And so, those are things that are really important to me from that perspective.


Justin Donald: Well, I love it. And I talk about this a lot in my book, where I think some of the keys to being a lifestyle investor are having that health bucket where you have strong health, and this is physical and mental health and spiritual health. I think those three are so important. And you talked about wealth, not just being about money because the vast majority of wealth isn’t about money, even though societally, it is.


But to figure out that component where you’re accomplishing financial freedom, that is a big thing. I don’t think net worth matters anywhere close to having the ability, like all day, every day, I would take a teeny tiny net worth, but having the cash flow to cover my life rather than what most people have is they have maybe a bigger net worth that they’ve been focusing on, but it’s illiquid. It’s this whole idea that you hear people kind of talking about how you’re asset rich but cash poor.


And I think most people live in this space where they don’t get utility from their investments. They might sound like they have a high net worth, but if you can’t do the things that you want to do, if you haven’t bought your time back, if you don’t own true freedom and autonomy and agency in your life, it doesn’t matter to me how much someone’s net worth is. I know people with huge net worth that are a slave to their business or a slave to the material possessions that they bought, or the mortgage payments on the 10 homes that they own.


But I would much rather have a more simplified life where I don’t have to worry about money. Money just shows up. It shows up every month. And whatever the expenses are, they get covered. And if I want to do something different or buy something new, I buy an asset that can produce that income. If I want to go take a cool trip, I want to be able to do it with passive income. I want to know that that was like a one-month distribution to go do that.


But I still have the asset that’s going to produce next month. And if I’m going to make a risky investment where I’m hopeful that there’s this outsized return, even though the risk is really high, it’s the whole 0% interest loan for an undetermined period of time in a high-risk asset that usually goes to zero, but you don’t know that for 20 years. I would rather do that from the bucket that has cash flow coming that’s all surplus above and beyond what it costs me to live.


Scott Ryan: I love that. In your book, you have, I think it’s like lifestyle and then it notes like expenses lifestyle and then live your dream, right? Your dream is your trip to Bordeaux and Monte Carlo. That comes out of the cash flow bucket, which is good.


Justin Donald: That’s right. I mean, it was an expensive trip because it was an epic experience. And I think most people would have balked at the price of it, but that was just one of my monthly distributions. So, I don’t feel bad spending the money going on that trip because I have an asset that’s going to produce that same amount of income next month too.


And for me, I’m at a point in my life, Scott, where I care so much more about experiences than anything else, way more than material possessions. I want to go experience the world. I want to do so with my friends, with people that I love, with my family, with those closest to me. And I want to be in control of my time.


So, experiences are what people remember. They don’t remember material possessions nine times out of ten, but they’ll remember that one time you went to some epic trip or had an epic meal and had this great conversation. And that’s what I want. I want people in my circle to have great memories of experiences that they would never have on their own.


Scott Ryan: Yeah. I would add to that. They’re not mutually exclusive, meaning that trip alone, two of the folks on that trip are potential operating partners for us. There’s one guy on the trip. We’re looking at buying his company. So, you spend 10, 12 days with some really successful affluent people under common interests and really amazing experiences. Everybody breaks down barriers, and you get to know people, and there presents opportunities through that experience. So, I think that’s a really cool way to not only have an amazing epic time with somebody, but a lot of times, it evolves into business.


Justin Donald: Yeah, there’s no doubt. Well, I would love to know where we can find out more about you, learn more about Lotus Domaine, and just get a chance for people to, if they want to connect to be able to reach out.


Scott Ryan: Yeah, absolutely. What I’ll do is I’ll send you my contact information at the end of this podcast. You can throw it up and do your graphics magic that you do, and we can go from there, Justin.


Justin Donald: That sounds awesome. Well, very cool. Any last thoughts? Any last comments? Words of wisdom?


Scott Ryan: Yeah. I mean, I think one of the things that my brother and I live by is how you do anything is how you do everything. And so, getting up, showing– I think Woody Allen said 70% of success is just showing up. I think it’s 100% success is getting up, getting ready, getting dressed, make your bed, all the stuff that your dad told you. We do it all and show up every day, give 110%. And I think also the focus on that work-life balance, that’s something that I’ve incorporated now that I’ve moved to Puerto Rico.


The joke at Lotus was if you don’t come in on Saturday, don’t bother coming in on Sunday. And I think we’ve built a great team and we have some really good players that are mentioned in our podcast. So, now, we’ve spread that work and we’re scalable enough to execute the right way because at the end of the day, no one on their tombstone says, I wish I’d worked another day or made X number of dollars more. So, I think that work-life balance between health, wealth, and relationships is key. And that’s what my focus is. And you’ve helped me do that as well with your book, my friend.


Justin Donald: Well, thank you. I appreciate that. I appreciate your time. This has been awesome. And if you are interested in learning more about investments like this and learning from people like Scott and many others that I’ve interviewed, apply to join the world’s most exclusive mastermind, The Lifestyle Investor Mastermind, which is designed for helping people become savvy investors and to regain control of their time, to buy their time back, and to build their wealth, build their cash flow, build their passive income with deals that the public is never going to have access to, with terms that are preferred, with deals that are de-risked, with extra perks built in. So, if interested, check out


And I want to close this session this week like I do every week and that’s with this question. What’s one step that you can take today to move towards financial freedom and living a life that’s really on your terms, one that you truly desire, a life not by default or autopilot, but rather a life by design, your design? We’ll catch you next week.


Scott Ryan: Guys, thanks.

Keep Learning

Exiting Scribe, Investing in Hard Assets, and Building a Self-Sufficient Homestead with Tucker Max – EP 152

Interview with Tucker Max  Exiting Scribe, Investing in Hard Assets, and Building a...
Read More

The Secret Strategies of the Ultra Wealthy with Greg Smith – EP 151

Interview with Greg Smith  The Secret Strategies of the Ultra Wealthy with Greg...
Read More

Billion-Dollar Scaling Strategies with Michael Abramson – EP 150

Interview with Michael Abramson  Billion-Dollar Scaling Strategies with Michael Abramson In this episode,...
Read More