Transcript of $33,000 a Year: What Ultra-Wealthy Entrepreneurs Pay to Keep Learning New

fail fast and take risks, I didn't really find that was so much lived. I think because we're an organization, our base is an entrepreneurial spirit. We've got the freedom. I can pitch almost anything, and if I get the buy-in, just the freedom and the ability to try things really quickly, to make decisions quickly, it's not going through all these layers of process. I love that part of it.

You don't win by following the playbook. You win by rewriting it. 700 episodes deep with the people who actually built something real. No theory, no fluff, no shortcuts. This is Right About Now with Ryan Alford. Hey guys, what's up? Welcome. I'm Ryan Alford, your host. We say if it's radical, we're covering it. Well, I like to say every day is a holiday. That's why we got Lisa Holliday here, the Chief Experience Officer of Tiger 21. What's up, Lisa?

Hey Ryan, so glad to be with you.

Lisa, I know you served in a lot of different roles I know we're going to talk Tiger 21, but maybe let's set the table for our audience. Let's tell everybody a little bit about Lisa.

As I shared, uh, during the pandemic, like a lot of people, I decided to go live where I like to vacation. I headed back to beautiful South Carolina, have great family, community. So life is good. See, I live up to that last name, Ryan.

I know you do live up to it, but I think you're being a little bashful, or you've done some big things. I see on the resume Mercedes-Benz, Marriott. I was in the big brand world at one time and then moved back to South Carolina. We still work with some big brands. It's fascinating kind of looking at your professional journey. It's kind of the who's who's of brands.

It didn't start off that way, Ryan. I studied, I thought I was gonna be an English teacher and then decided pretty quickly, student teaching, that that wasn't the career path. Bounced around a good bit, went abroad and thought I'd try out being a Shakespearean actress. And clearly that didn't work out for me. Came back to the States and really approached finding my career path by trying out just about anything and everything that sounded interesting. And when I landed at Mercedes, That's when I figured out the career path for me and how much I really loved brands and understanding what motivates consumers to have brand love. How do you build brand love? And really experiential marketing, bringing humans together to connect in person. Thanks to the pandemic, figuring out how to do that virtually too. Mercedes was really probably the most pivotal career for me and stayed there for 10 years. A recruiter called me about the opportunity at Marriott and I have a bit of wanderlust. I love travel. Joining a global brand and leading 5 luxury brands for that iconic hospitality company was pretty amazing. After 8 years there, a recruiter called me about the job at Tiger 21.

Jumping over a small organization and with an entrepreneurial spirit just really, really appealed to me. And obviously very, very different than being with large brands. I've been there 3 and a half years building out a new department. It was a new executive role in a brand new department and building it out during the pandemic was interesting and challenging, but also an incredible opportunity. I love experiences and brand building. It's one of my passions.

And it's interesting because when I think now the modern definition of branding with the way social media and even the pandemic, like the interplay of all these things, it really is the pinnacle when you can blend the two things. And that's really how you do branding now. It's so hard with mass media being different. When you could reach, when everybody's attention was just on TV, you didn't have all these screens and other things, you could kind of bring the brand to life. People were paying attention, you have a focused audience. But now everyone's so distracted. These worlds of experience and branding, I feel like, have melded together. In a lot of ways.

100%. You know, it's back in my early career and branding was, what's the TV spot? What's the tagline? What's the radio ad? God, I'm gonna date myself.

You know, I ran newspaper ads, Lisa. I was in '01, just sending out to 8,000 newspapers versions of PDFs.

The space I've been in most of my career has been the luxury space, and that's always been a different type of target consumer to reach. With this specific target audience and a lot of target audience, I go back to, I was mentioning how much I love my Clemson Tigers. There's nothing like the experiential part of being with a group of humans who are all cheering for the same team. And that experience is gonna do much more than any direct mail piece or anything else. That's why I believe so much in the experiential part of bringing people together in community. And if, you know, not to keep going back to the pandemic, but when you're relying on that as a marketing mechanism and all of a sudden that's taken away from you, that was a pretty interesting challenge to think about how you maintain and continue to build community and connectivity among humans. And your team. We haven't even gotten to how do you keep an engaged team internally to make all those things happen.

I just thought of this, like when you said it, when you brought up the Clemson analogy, I think it's a really good one. It's branding. If it does its job, you do create fans. Fandom is a really interesting parallel with branding because college sports and football being so big in the States, you have these natural tie-ins and natural built-in stuff. But for brands, including Mercedes especially, You're trying to build fandom at the end of the day. And they are. People are passionate about cars. How do you bring fandom around brands and other things? It's even fascinating as I think about it.

That's what our roles are. I used to use this example at Mercedes, and luckily we had great product. But somebody has a bad product experience because so much of the car and automotive brands are about the product itself. And I think our jobs as marketers and brand builders is how do you build love so that even if somebody has a bad product experience, they have such an affinity for your brand that they're going to stay with you. loyal to you. And at the end of the day, that's what you're trying to drive is that loyalty.

Absolutely. I've been on my soapbox recently with some of my posts, especially in the business realm, about that very thing of performance marketing and building mousetraps. All a mousetrap does is kill the mouse. It saves the cheese and kills the mouse if you aren't building for the long-term return. Because someone buys one time, it's great, but you need that lifetime value. You need customer loyalty. It works both ways. I have started a book called They Have Lifetime Value, I Have Lifetime Loss. And it's the lost art of customer relationship management. That's on my list.

That's a good one. Part of the big project I've worked on at Mercedes that I took with me, and it was a big part of what we built out when I first joined Tiger, was the journey your consumer takes with your brand. At Mercedes, it was our clients. At Ritz-Carlton or St. Regis, it was our guest journey. And now at Tiger 21, it's our member journey. So what are really thinking strategically, not just hoping they'll happen, about what are all those touchpoints along that journey? Hopefully a member that is coming in and just joining us in this first year, 10 years from now, we're going to be thinking, okay, what's their journey now that they're a 10-year member, a 15-year member, a 20-year member, but really plotting those points and how do you drive that engagement along their path with you?

Yep, you got to be intentional. As I like to say, hope is not a strategy.

You and the quotes today.

Yes. Hey, I'm a quote guy. I think I spend so much time on Instagram. I want to get to Tiger 21. But before we get there, you're the Chief Experience Officer. We've talked about this, we've kind of been going dancing all around it. I think for people listening, it's a fairly new title in the last 5 to 10 years. And for many people, they may not have even heard it that often. Define what that means.

At Tiger 21, it means curating everything our members will experience. And for us, it's across 3 different pillars. So our pillars for our members, our value proposition to our members is we're going to bring you opportunities to learn because we're a peer-to-peer learning organization. How do you learn from each other? How are we curating those learning opportunities for you? It's access. How are we providing what we call those only at Tiger 21 moments? The surprise and delight opportunities. We were just in Nashville with members last week, and we took them to a recording studio where they were able to experience what it would be like if you were an up-and-coming country musician recording your songs, which was really, really special. We followed that up where each member that participated received a copy of the recording. Unfortunately, it wasn't the original recording. So the, the up-and-coming artist did an original song of hers, and then she covered a Chris Stapleton song, Parachute. Everyone got her cover of that song. So So you're not only having the access to that special opportunity, but then we're doing something to help trigger that memory again, and hopefully that leads to loyalty.

And then the third pillar is connect. I don't want to say that's the easiest one. It's in many ways the most important one because that's what's getting to the community opportunities. How are we providing opportunities? And I'm talking a lot about the in-person because that's the sexier part, but it's the app. So how are we providing opportunities that it's super easy for you to connect with a member that's Maybe right now in Dubai and you're in California, you have a reason to try to connect. It's across those 3 pillars that I focus on. And really it's about driving retention. Once a member joins the organization, what are we doing to make sure they find value in the experience and they'll stay with us?

Yes. I'm sitting here like nodding mentally and all the things you're doing going, this is how you market in this day and age and how you keep clients. And I'm also going, damn, I'm supposed to be on to Nashville. I've got some country music artist friends. I'm actually going to see them in a few weeks. Dang, I want to go record a song. Not me, but this a special song just for me. I'd want that experience. That's cool.

And those are hard to create, those money-can't-buy experiences, especially when my target audience are ultra-high-net-worth individuals. But I love the challenge of that, you know, striving for excellence. And no matter who you are or how much money you have, one thing none of us can buy more of is time. How do you really create value with people who are giving their time to you? And not just giving, but paying you. It's a super important obligation to deliver, but it's also It's such a privilege.

Let's talk Tiger 21. Let's get a real clear definition for our audience about what Tiger 21 is, what you guys do, just the overall organization.

We're a peer-to-peer learning organization or community for ultra-high net worth individuals. Most of our members are entrepreneurs or executives, leaders. Most of them have built a business and had a liquidity moment, and they are looking for other members to help them navigate the challenges and opportunities that come with that. The core part of the experience is members are placed in groups of 12 to 15 individuals. So a group and a professional facilitator, what we call chairs, facilitates a monthly group meeting. That's the core part of the experience. What I work on curating are all the opportunities in addition to that core group meeting, whether it's events I mentioned, whether it's trips, whether it's learning opportunities, whether it's their digital experience, both online and in the app, and then the recognition opportunities. What are we doing when a member first joins? What are we doing And when it's their 5-year anniversary, their 10-year anniversary, really, how are we making sure they love Tiger 21 and their experience with us? It's super cool.

Talk to me about— it might not be connecting the dots of what the group adds to one another, how that tide raises everyone.

Personally, I'll tell you my why for joining Tiger 21 when I interviewed was if I can come in and lend my talent and my resources to help individuals who have the financial resources to really make the world and their communities a better place, then And that seems like a pretty great thing to contribute to. People often think, oh, are they coming in to learn how to make more money or invest more wisely? That's 100% part of it, but it's also about family. It's also about philanthropy. It's also figuring out your what's next in this world and how can you continue to contribute. And what happens in those group meetings is really connection and being able to talk about anything and everything and having a level of trust and support from other individuals that's really beyond comparison. Also, you have to really think about the type of individual that would have achieved the level of that success they've achieved, but still believe that they have so much to learn. And not only do they want to learn, they're willing to pay $33,000 a year to be part of a community that is supporting that. It's a different type of person that's going to make the decision to join Tiger 21.

I think I know the answer. It's different because YPO is like young professionals and this is kind of more established, but there is some connective tissue in the type of what we're talking about here, isn't there?

100%. And that's the organization most people usually would compare us to. We don't consider YPO a competitor. We do have some members who belong to YPO and belong to Tiger 21, but it is a different value proposition. YPO is much, much larger than we are. We sometimes say more the graduate school after YPO.

Yeah.

Being in these really small, intense groups just lends itself. And it doesn't mean, obviously YPO forms great connections for those members and there's room for both. The peer-to-peer learning space has really grown a lot. It grew a lot, especially during the pandemic because people were wanting and looking for even more connections when they felt so disconnected.

Yeah, other than sharing stock tips, I do need a few of those. Are they getting advice? Are they coming in maybe still active in a business and looking for real board of directors, but not literally? But you've got obviously confidentiality, so you don't have to worry about that. You've got all those things which I've really liked reading about Tiger 21 that you could just feel safe and you're around like individuals. But are some of these people active in maybe another venture or business and getting insight and recommendations in that?

100%. Our member age range, just to give you an idea, because I think that's the other thing really special is just the diversity of our memberships. Our youngest member is in their early 20s. Our oldest member is in his late 80s. It's a range of perspectives. And you can imagine when you think of that age range, not everyone has sold their business and thinking, okay, now what's next? There are active executives. There are individuals who've sold their business and are thinking about which opportunity is next and what do I want to do next with my life? But yes, there's plenty of our members who are still super active. in their business and running their businesses and creating opportunities in their community and opportunities for their family.

Yeah. Where did the name come from, Tiger 21?

Luckily, our founder, Michael Sonnenfeld, is still involved. He's the chairman of our board. He's very involved in the organization. Coming from legacy brands, I feel very blessed that we still have his influence. He had a liquidity moment and he wanted to create a group where he could have discussions about things that were happening in his life. And so he started it. Tiger is an acronym. We use obviously the acronym, but the meaning behind TIGER is the Investment Group for Enhanced Results in the 21st Century. And what started really as probably mostly an investment group has definitely evolved into something much more than that. But we do have plenty of opportunities for our members to learn about investment opportunities. There is a platform for that we just launched called T2One Invest. It's password protected. It's for our members only, but there's definitely that component. But there's also the components around your life, your travel, your family, family dynamics is huge. Really, really important piece of it.

That's great. You have an app, you mentioned that.

It's members only. Once you're a member, Ryan, you'd have access to the cool app and be able to engage. We're at right over 1,300 members in 45 cities and with 100 groups and growing internationally, which is super exciting to really have more of a global footprint and that global community for our members to network and learn from.

Yeah, I love that. That we're US-based or how global we're getting with the platform.

Growing globally, there's tons of opportunity, big focus. We focus on Singapore, the UK, Dubai. We're in London and Switzerland now, but there's obviously a lot of opportunity to grow globally. And then the majority of our members are in the US, and then we have members in Mexico, Canada.

Is there a home base for Tiger 21 with 45 cities? And is it just wherever you want to throw a party and get together?

Not exactly. I wish it was that easy to grow a group. Key is to have concentration of members in markets where you would assume we are. And then there's really interesting markets that popped up again during the pandemic. with so much movement among individuals who could pick up and move. But the key is we really need a strong chair. So that individual I mentioned that facilitates the group meetings, we really need a strong chair in a market. And then that chair works closely with us to grow that group. Headquarter-wise, corporate, we do have a base still in New York. We have a home office there and we have a base in Santa Barbara, but we went completely remote during the pandemic and we're planning to stay that way. My team is spread out all over the US. Oh, wow.

That's great. You got representation a little bit everywhere.

Yeah, 45 cities. I was bringing it up because it includes Zurich, London, Geneva, Vancouver, Montreal, Toronto, and then every US market that you would think of, we have a presence in, which is great. And it brings that diversity of thought to our members and to their group meetings and to us more broadly as an organization.

What's it been like? Mercedes-Benz, Marriott, gigantic corporate brands. And then Tiger 21. I'll draw this parallel. I worked on the largest brands in the world in Manhattan, done some of the largest campaigns on TV, then started my own agency. It's a fascinating parallel, likely for you, and not just from a budget perspective, but just team and dynamics. What's that been like?

It was one of the reasons, as I shared, that I accepted the position. I loved the idea to come in and help support an org. First of all, I believed in the purpose and the why of the organization. So That was first and foremost for me. I love the idea of challenging myself. It's interesting because I've kind of come full circle. I thought I was originally going to be an English teacher, and now I'm part of a learning organization. So it's different, but there's been a common thread through my journey, my personal journey, that I love to learn. Coming in and challenging myself to come in and not inherit somebody else's job that had already been doing it and their files and their team, but come in and build something from scratch really, really appealed to me. But it's hard.

Yeah, I mean, Mercedes-Benz, there's not a check you really couldn't write. And not, not that money makes it, but right, it doesn't solve everything, but it helps.

While I was there, I negotiated the Fashion Week title sponsorship, the US Open, the Masters, the naming rights for, at the time, the Superdome, Those are big sponsorship checks. We were doing product placement in huge movies and Iron Man product placement level. And then Marriott wasn't the same kind of sponsorship budget. Now I would say my budgets are quite, quite smaller. What is a big number to me now in my forecasting is quite different when I was at those big brands. But no, I love it. I haven't regretted it for a moment and there's still so, so much opportunity. But my favorite part, I mean, I get to be around these human beings who have come up with these incredible ideas. It's just a fascinating group of people and the members are amazing. And my team, talk about a privilege to come in and build out a team and hire the individuals and create that culture. That's the other part we really leaned into is what kind of culture do we want to create? And so much of that is starting with who you hire. I have just an awesome team. I'm so lucky to work with them every day and my colleagues.

What's been the biggest learning curve or not even curve, but just learning lesson that you've kind of had or epiphany going from large to small or been having different Different opportunities. You've got challenges, but you've got different opportunities because you can kind of impact more. That was always my thing a little bit when you worked at large brands. It's great. We do these things and it's like hundreds of millions of dollars. And it's, did we really move the needle? I think we did. And I feel proud. And then what you're doing now, the smallest things can have a big impact.

Agree. We were just comparing our events. I'll go back to the events because you can probably tell that's my real love and passion. We were just looking at what was being done before we built out this team and now what's happening both in person and virtual. By the way, I know people talk about, oh, Zoom fatigue. We haven't found that at The virtual events didn't go away because the pandemic did, or, you know, the pandemic COVID became just, you know, like getting the flu shot now. It's and for us, it's doing all the virtual stuff and adding all the in-person back in. But probably my biggest aha moment and learning moment, and you'll know this, big companies talk about fail fast and take risks. I didn't really find that was so much lived. I think because we're an organization, our base is an entrepreneurial spirit. We've got the freedom. I can pitch almost anything, and if I get the buy-in, Just the freedom and the ability to try things really quickly, to make decisions quickly. It's not going through all these layers of process. I love that part of it. Being able to embrace that and know that we actually mean it and can do it and we're not just saying it.

That's fun. Being an idea guy, I would love that.

If anything, we have to say, okay everyone, that's a lot of ideas. Let's prioritize and focus. Yeah.

Narrow it down. Talking to Lisa Holliday, the CXO, Chief Experience Officer at Tiger 21. Lisa, what do you like to do when you're not working?

Well, it depends on whether it's college football season. Part of why I moved back to South Carolina, I love being on the water, stand-up paddleboarding. I love to cook. That's probably my creative outlet outside of work. I'm a big nerd when it comes to reading. You probably even know the little library I go to. I got really into libraries again, so now I have a library card. It's so cool.

That is a little library. I know exactly where that library is.

It's a cool library. It is a great library. I'm so involved with my family and my friends, but I want to get more involved in the broader community now that I'm back back here and putting down roots. And travel. God, I can't forget travel. Love travel.

What's your favorite dish? You said you like to cook. Or a favorite dish. I mean, are we talking all over the board or specific cuisines?

I do love Mexican. That's probably my guilty pleasure. Nachos and a margarita. I like just about everything. I'm a Southern girl. Give me some fried chicken and collard greens and I'm good to go, Ryan.

Yeah, there's some good fried chicken around there too. A couple of those, uh, gas stations that you think that wouldn't be good have some pretty good fried chicken.

It's called Palmetto Cafe and it's about a mile from here, Ryan. If you haven't had that gas station fried chicken, you're missing out.

I've had it. I've had it. I love it. Lisa, it's been great talking with you. I know we could talk more and more and more. I know we could have some brand discussions, but where can everybody learn more about Tiger 21 and anything else you've got going on? Some of your social profiles?

tiger21.com is the public-facing website. Our members have their own special website and app, but you can learn more about it. Looks great. We just did a revamp. And then, yeah, for me, I'm on LinkedIn. It's probably the one business-wise. Lisa Holliday. I would love to connect with your audience. It's been such a pleasure, Ryan.

That's great. And that's Holliday with an A. H-O-L-L-A-D-A-Y.

Yes. H-O-L-L-A-D-A-Y.

There you go. Give Lisa a follow or a mention on LinkedIn. You can find me on Instagram @ryanalford, on TikTok @ryanalford, on Twitter @ryanalford. We had that blue check before you could buy it. We'll see you next time. Here's the truth. Information doesn't change your life. Execution does. So don't just listen to this episode and move on. Take the idea. Make the call. Launch the thing. Fix the problem. Build what you keep talking about building. For more, follow Ryan Alford on Instagram @ryanalford and watch or listen to every episode at ryanisright.com. This is Right About Now. Now quit waiting. Go win.