Ric Elias - The Art of Living Well - [Invest Like the Best, EP.388]

0:00 I know firsthand how complex the tech stack is for asset management firms. And seemingly every new tool and data source makes the problem even worse, adding more complexity, more headcount, and more risk. Ridge line offers a better way forward, one unified platform that automates away the complexity across portfolio accounting. Reconciliation, reporting, trading, compliance, and more, all at scale. Ridge line is revolutionizing investment management, helping ambitious firms scale faster.

0:25 Operate smarter and stay ahead of the curve. See what Ridgeline can unlock for your firm. Schedule a demo at ridgeline.ai. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best. This show is an open ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money. Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolosis.com

1:00 Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of positive some. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.

1:29 Guest today is Rick Elias. Rick is the CEO and co-founder of Red Ventures, which has a portfolio of fast growing digital businesses like Lonely Planet, the Point Sky, Bankrate, and large investments in a variety of other businesses across industries. He began Red Ventures in the year two thousand and has grown it. to a global company with thousands of employees. Rick walks us through the early struggles that have led to a now flourishing investment platform, but mostly this episode is a master class on cultural values and philosophies that transcend mere financial gain.

1:59 We discussed the difference between living good and well, the power of forgiveness, and compounding more than just your capital. Rick's story is one of resilience, humility, and grace. His story about being in the front row of the plane that Captain Sully landed in the Hudson is singular and moving. Please enjoy this great conversation with Rick Elias. So just before

2:19 We came in here. You and I did something together on stage. And then I was talking to Carlos on your team. And he asked me whether or not And how I prepare for these things.

2:31 And I told him the truth, which is that In some literal sense I don't prepare, I don't sit down and think about them right ahead of them. But in some other sense I prepare all the time. because I end up talking to people that I'm most interested by and curious about and have met before usually like you and I have met before.

2:47 And that the only thing I prepare is the first question. And I usually do that about five minutes ahead of time. But I hadn't done that. And so I actually asked Carlos to give me the first question that I'll ask.

2:59 This first one comes from Carlos, but I love it. You cheated. So I'm using it and I cheated. I like it. Carlos' question in mind. Is What is the big dream? My big dream

3:11 is to live in a state of well being Most of the time. And to s have a sense of lifelong satisfaction when The end comes. So it's really very internal versus

3:25 something that gets accomplished or left behind. We're gonna pick That apart in detail. But go down one level. Sure. What is the

3:34 Red Venture's big dream. We've been on this journey for twenty four years. Then in one sense it feels like we're about to Go on a on another ten year. journey of reinventing ourselves.

3:46 Right ventures over time, hopefully Becomes a place where A lot of this Whatever success we've had gets put back into the system. So more of a full circle versus

3:58 A full line to the right or to the left. Or down, but I still think that We're years or decades away from that. Can you

4:06 Tell us what it is. I ask that in the stupidest, simplest way I can for a reason because It's pretty hard to figure out what it is from the outside. On purpose. I know on purpose, but I have to ask. Maybe the best way to ask is how did it begin?

4:22 The easiest way to understand it at a high level. You can think of ourselves as a Operating private equity. platform with permanent capital. hyper focused on the digital world.

4:35 With different business models. under the belief that culture really matters and that if you use that as the connective tissue inside of the portfolio companies You can get some level of alpha vis vis vis companies being separate. And today we depends on how you want to count, have about fifteen different companies inside of the portfolio. All over the place between

5:00 Europe, Brazil, Puerto Rico, and then our core businesses here. Inclusive of a big join venture with you know the healthcare and so forth. So if we go back to the very beginning. Something worked. You and your team were awesome investors.

5:14 or transpotters or operators or some combination of those things probably Maybe some luck sprinkled in, which is true for all of us. How did it start? What was the Origin story. Look.

5:26 I think we're more lucky than sprinkle luck. I've always believed that. And I've if I look back in our journey. Dan and I started this company in January two thousand. Dan and I worked together before this at a company called Send In C U C. And we really started with two principles in mind.

5:43 One was let's build a company we w wanna work for. And Dan and I are not typical. We're very different. In hopefully good ways. But we both are of the same opinion that life is to be lived with enjoyment and that we will wanna work at a place

5:59 Or build a place that we will wanna go work every day so we never have to work. True definition of being an entrepreneur. And then the second one in I think we said it at the time without really understanding it. Which was a company that would at last us.

6:12 And even though we will want to do this for a long time, Dan retired about a year ago. a company that would outlive those. What I have come to realise is It will outlive. Us. Through the people that get trained.

6:25 In our platform. not as a company itself. And then many of the businesses hopefully are here for decades to be. But that really were our basic principles. So when you start with that The business plan was completely flawed. We raised two million dollars from our friends. This is the frenzy of January two thousand. This is before the first internet bubble implosion.

6:45 Raise money on three PowerPoint charts on the dumbest of ideas. Basically a paper based search engine. where we were gonna help online companies use offline media and By November we had a hundred and seventeen thousand dollars left, no revenue. And this crazy thought of like I will never attend my reunions. 'Cause all the capital came out of my business school friends and

7:09 I'm a proud guy. I'm like I can't So we literally just hunker down, hustle, sold. marketing program, sold anything anybody to hire us to do consulting things. And we knew a lot about direct marketing at the time and for a couple of years just muscled our way through it. In two thousand and four, we had enough money to pay our investors back.

7:31 And we said, look, and we made a commitment to you. Here's your money back times ten percent. But we're done. If you s keep your money in here is at your own risk and I hopefully hope you take the money back because that burden of taking someone's money. Was a lot. And in oh four, oh five was when Google was becoming

7:48 The de facto aggregator of intent. They had this rule where you could not double serve as a brand. And we started thinking, wow, brands are gonna need somebody to kinda help them defend themselves in this environment that's aggregating intent and customer acquisition is the life being of all budgets and is actually a line that is not in the operating budget, it's in the revenue budget. So there's a lot more leverage.

8:10 And we literally said, Let's go try to figure that out. over the first couple of years build a core tech where We can map. a couple million toll free numbers to an online experience and give you a phone experience that was quasi personalized by how you navigate it online.

8:26 So we could go to any brand and say We can outconvert whatever you're doing. And this notion of take your agency, take your call center, take your internal operations, we can all convert them by thirty percent. If that's not true, don't pay us. But if it's true. Give us a piece of the upside, don't pay us as an agency or a service provider.

8:45 And that became kind of the first unlock and call it two thousand and six to two thousand and ten. And from there there's a cemetery full of skeletons of bad ideas and We went our way through it and lo and behold, come from two thousand and ten to now, and this is where we are. What was the first thing you ever bought? What business was the first business you ever just bought outright? First meaningful thing we bought.

9:09 Where we literally broke the bank. We had a pristine balance sheet. was bank rate. Bancreta at the time was one point four billion dollars and It wasn't worth that. Before we bought Bancrate.

9:20 We bought an asset in financial services that it was a tiny asset where we said, let's go and prove that we can actually Use that asset. in Google and Pay Church and SEO and really start doing what we did in telecommunications.

9:34 Using someone else's brand, using our own brand. In financial services. We did really well. And we're like, Okay. Let's put all our chips in the middle of the table.

9:42 And Bankrate was our first big acquisition at the time. We don't credit cards.com, the Point Sky, Bancrate and a bunch of other miscellaneous assets and it was our first Okay, we're in the big leagues now and we have a lot of debt. There's quite a lot of glossing over going from Two million dollars paying back your investors to a billion and a half dollar acquisition. This is a big anymore. But I'd love to dig into some degree.

10:04 What would you credit your early operating success with. Obviously you got to that scale. on in an unusual way with not a lot of outside backing and control of your own destiny and permanent capital and all these things.

10:17 So if you think back on that specific chapter. What was going on? What were the things you were doing or the way you were doing those things that made it possible? It's a strange story. Survival. To some extent. When you spend the first four years two little kids, both of us

10:33 Not taking any money. Humility. understanding that this could change easily. Early on, we would meet with our eighty employees, call it two thousand and seven and eight, and we were now making millions of dollars to profit and I will say oh enjoy this. These are the good old days. Some day this will then It was this constant belief that

10:52 This was a moment in time and if team work as hard as we worked the last three years. This will end. So a lot of it was like we were relentless. And one of the things early on is For whatever reason. We have never competed against anybody.

11:08 I never thought that our competition was somebody else. And we've really never competed And maybe it's because of our near death experience as a business sorely against the fear. Of something. We always thought look. If we can compound our performance a little bit every month.

11:24 And our business model gave us the fruits of that. It was all performance based my um deals. We got addicted to this notion of Incremental performance just becomes really virtuous for us.

11:36 And that was our thing. Your strengths become a bit of your vulnerability. I think to this day. R DNA. thousands of people strong is incredible operators.

11:47 Really good optimizers. Maybe not as great people doing high end product or experimentation and other things. Now we brought in a lot of people to help do that and all of that. That is probably our core DNA of our adventures.

12:02 I'm gonna zoom back and forth a lot here. Sure, sure I'll go all the way to back to today. I show up today and I've not seen anything like this. We're on a massive campus. There's thousands of people here. It feels like a

12:14 Self contained world. And It is physically, literally, it's a self contained world. And it has a very specific, coherent vibe to it. Which makes me wonder about culture.

12:27 You said there's more than a dozen companies in all sorts of places, but it it feels like this is one company and one team just walking around. Maybe say a bit about how you've designed and What it is. What am I feeling?

12:39 How did that come to be because I think those are hard to establish. I am wonderful at explaining the world looking backwards. We were talking earlier today. I can give you the greatest story, which I will in a second. But I'm not really sure that when we set out to do this

12:55 This was the original plan. This is just The ability to Iterate and pivot and iterate and change and all of that. One of the real unique things, look, we didn't raise outside capital until two thousand and ten. A decade of bootstrap.

13:11 When we raise capital, we didn't need capital. We didn't need it for anything. We did it. Because Our employees wanted a little liquidity and investors were wanting to buy in. So as a result, and in general ultimately we ended up in a structure where we have permanent capital.

13:26 Meaning we have wonderful investors. General Atlantic was our first investor, still a great partner. Silver Lake came in five years later, also equally a great partner. But the notion that we don't have a clock that we don't have a photo up moment where we're gonna go public or we're gonna try to sell the business. For good and for bad as just giving us license to invest in things that others wouldn't. And back to the principle of a place we will want to work for.

13:51 We decided that our culture was really gonna become That string of DNA that will permeate around the whole company. Mm When you walk into our building

14:01 You'll see a series of belief statements random on a wall. And our belief was look, we can't teach you values. We can't teach you things that you learned at home, but we can tell you what we believe. And if those things resonate with you

14:15 Then you may want to work here. And then when we do performance reviews, when we do evaluations of things, when we anything we do, we come back to okay That is kind of our framework. The beliefs evolve. And we'll evolve and we'll continue to evolve because the core belief is everything is written in pencil.

14:31 Which in itself is a bit disorienting at bad times, and it can be other things, but Look, this is all a game. At the end of the day. We've been really lucky to play twenty four innings of an incredibly interesting game. Not every inning has been perfect, and that's part of what makes it beautiful. Which of those four beliefs, not counting that core one, is most on your mind?

14:51 Distress. There's seven bullies right now. We've added some Making every second count. really matters because I I think the world right now

15:00 Those starting in a perch, which I think we are having an advantage, but those are gonna be incredibly nimble. and willing to adjust and adapt at a whole new wave of Innovation coming. It's what matters. And one of the things that happened during Covid is our operating rigor diminished.

15:18 I'm not sure that is For us alone, but this notion of working less intensely in the office, less together. There's some very good positive things that come out of that in a lot of capacities. And I worry about do we have that fight? Do we have that

15:35 Thirst do we have that? Fear of not being relevant in ten years. I don't think the people that show up today and look at this beautiful campus feel the same hunger we felt when we didn't know if we were gonna make it. It's a circle of life. But how do you instill a desire of people wanting to go do something for their growth for their own good? It's a really interesting challenge in kind of a leadership standpoint.

15:56 Have you found anything that does that effectively for the marginal person that shows up? And has A much bigger foundation to build on top of than you did originally. Whether it's an incentive structure or an attitude or a way of operating. Is there anything that works? There's no magic bullet. I think you gotta find people that Wan it. Wan it.

16:15 And then I think typically athletes or people that are musicians, people that have been coach heavily in their lives. end up doing well in environments like this because Coaching is not. Criticism. It's like you're making me better. People that

16:29 are super curious, I think right now to be successful in the next five years, you almost have to be willing to re-underwrite your skill set. You need people that really are in that. Mindset and mode.

16:41 If I were to be annoyingly reductive. About The Red Venture stories. Would it come down to You were just

16:50 Earlier and better. at understanding how marketing was changing. in the internet era than others. That would not be accurate and that would over inflate really. what we did. We did not know we were earlier. Actually I would argue that we were a little late.

17:06 We were late to mobile. We're trying not to be late in AI. But we're also afraid to be too early. I think we bet on ourselves. We

17:16 work collectively better than most. Um We're we're hyper competitive against ourselves. And in life a lot has to do with picking the right competitors. And I always joke that if this building, this campus was in Silicon Valley.

17:29 It will be irrelevant. This region is something. I love that saying that you can either be the tail of the lion or the head of the rat. So we get great talent because all the schools around here super talented kids that wanna stay in this region and wanna be in a place where they get trained, they get invested in. They are Pushed on.

17:48 They love coming here. We have insane talent coming here. My sense is and I'd love to just like pick any example you want that Frequently you would Buy a new company.

17:59 And The performance of that company would go up a lot after you owned it. Correct. Can you pick one story? And in some detail describe

18:08 What it was when you got it and what you did. And how it changed. You think about the core of what Red Ventures Was And it still is to some extent. It's a B to B platform on

18:21 Basically doing Customer acquisition, performance marketing. Growth. Like at the end of the day, when I sit down with a CEO, I said, Look I can help you grow and you only pay me if that's true. It's not the hardest sell. Every CEO needs growth.

18:35 Especially. And we bring tech operators, data, we bring a bunch of tools that are really hard for you to replicate. And it's easy to measure. that we provide incremental growth versus what you would do yourself. And so It's usually is the rejection of the organization that makes it hard. So the timing of this conversation has to be

18:55 either a new CO or a crisis or a situation, a business that is usually performing pretty well, or feels like they're in a good spot will not want to engage with us in that sense. So By virtue of our value proposition We have this ability to take anybody's Customer flows.

19:14 And using all our capabilities. Make it better. So We haven't batted a thousand, but we have had more of a quarterback completion rate than a baseball player batting average. a taking a company and if we bought it at

19:27 Ten times. Within two years it was Four times. And that gave us a lot of conviction. to a point where probably we overplayed our hand on our last acquisition. Right. So it just

19:39 One of those, but we can take any funnel where there's heavy data, heavy experiences, and use our technology to basically yield a lot more out of the same flows. That that has happened. Time and time again in every asset we bought. This was the

19:54 supposed promise of private equity that you would buy stuff and make it better. And then resell it. I think in many cases, if you're cynical about it, like that really doesn't happen. Like there's more financial engineering that goes on than actual operational improvement. And obviously what you're describing is like unbelievably valuable if you can buy at ten and pretty quickly you effectively pay four. So why aren't there

20:14 Ten red ventures. Like why aren't there ten firms that have this specific expertise. That are just really good at this function. that buy things and make them grow. It feels like I'm missing it because there aren't.

20:28 I've looked. Tell me how someone gets paid and I'll tell you how they behave. And most people that Are in this space. are here to grow something to sell it to somebody else.

20:40 Um what we've been able to prove is we've been able to do this across Seven or eight different industries. We've had lots of really good competitors show up in an industry or two. Some of them better than us at certain things.

20:52 Some of them go the brand, okay, I'm gonna build my own consumer brand. versus building a much better Middleware? In others I'm gonna do it really deep here and then I'm gonna sell it to somebody. So I think a little bit of this is incentive structures.

21:05 If you had to describe how you got so good at this function. Is it just iterative? learning? Is it stacking lessons on lessons? Is it a heavy data focus? What is it that makes someone good at the thing you do so well? Compounding of a lot of things.

21:20 A lot of three percent on each other. quickly are twenty percent. But here's what's really interesting, Patrick. That you could argue is maybe fifty percent of our business. The business that we're super excited about in the UK, we own a true software business that powers Eighty percent of all the real estate agents. We own a data business that nine out of ten banks.

21:41 Use to do all their valuations. In the US we're Really excited about the mortgage space and what we may do as a mortgage lender. We have taken this operational chops now. And are doing lots of different things that are not performance market. So we took this B to B business.

21:58 ended up saying, Wow, we can do this and buy assets to do this ourselves and the value is now we get All that richness of beta. To take to our B2B business. So I can go to somebody and say, look, I have a ton of consumer intent data, but then we're saying, look, this chops apply to anything. So Using the private equity We're like

22:15 We think we can do this in other places and with fairly good success we've been able to prove that we're good operators. When you see a new company or a new team or something. What gets you excited? Like what is your taste? To buy.

22:29 Yeah. We really like the bets we're leaning into right now. So we're trying to figure out things that are kind of be augmentative to the bets we have. that are gonna unlock something and are gonna mode us in some ways, give us a capability, give us something that is unique and different but When I sit down, a couple of the things that I think about without thinking about.

22:48 So I really try to understand what is this person's motivation. I've bought enough things and been around enough things that ultimately It's not what they're telling you, it's really what they want. If they're gonna really sell you something and

23:01 not really be committed to whatever the transition period is, multiple years from whatever it else, that's really, really important. Understand the motivation. of the cellar. And what we've done really well is when we've engaged with somebody that we really understand the why. The second thing is I like places where you can win in multiple ways.

23:20 So when you make a single bet. It's like okay, I'm betting this happens and we have to compound growth at twenty percent, but if we Don't compound growth at twenty percent, but we also are able to use the data for this and we can build a model for that and we can connect that to everything. Then you can say a bunch of point sevens added up end up being Two and a half, three times something.

23:38 That's the value of the platform is that you can look at these things and sometimes these assets have a lot of insurance into the platform other value that brings. And because of our cultural alignment, You can get that out. A lot of companies can do this. If it runs like a traditional portfolio or a private equity portfolio because the companies are not connected at the tech layer. like we are or at the cultural layer like we are.

24:00 In the first part of that equation, that's the motivation of the seller. What are some of the most common reasons that you would decide not to? partner with someone, let's say even if you loved the thing, the business. What would be something that Would scare you away.

24:15 If I have on Really think the person is generally a good human being. Doesn't have to be Like me or whatever. I'm turned off because that will reflect on the things that I won't be able to see.

24:25 So I'm trying to get a sense of is this a good human being? If the person on the other side If I sense that they're running away from something Versus running towards something? They know something I don't know. So I'm very beware of why is it? Why now?

24:41 Why us? Why this price? I'd rather pay a little more on something that people want than steal something. And one of the things we do is once we lock in on something, Patrick, we've never retraded on anything. Our word really matters, and I think ultimately I expect that to be the case on the other side. Once we lock in, we go for it.

25:00 One of the most interesting set of things that you and I have talked about is the ways In which your attitudes towards certain things change. Between my age and your age. So it's eighteen years between us. I'd love to kinda go category by category.

25:13 And have you reflect on how your views have changed. from my age to your age on some topics everyone cares about. So the first one is money. Money's a tricky thing. 'Cause money.

25:27 society and most people basically have set up that More is better, more is better. And we measure things in money and value and the value of your company and the value of your business. And in reality. If you focus exclusively on money, you missed

25:43 The journey. You miss what this is all about. After a certain amount of money, and everybody's a little different, but it's a lot less than people think, it doesn't really affect your lifestyle. And at some point, it affects how people. Treat you? And it affects

25:56 Your kits. It affects what you're gonna do with it, your responsibility with it, it affects all of it. I think money is one of those things that it's a privilege to have. But if you're not careful it can change you.

26:09 Or it more importantly, it can make you so addicted that you spend the rest of your life accumulating something. That is worthless beyond a point. We trade all our time. For money. That's what we're doing. We work our butts off.

26:22 For money. And at some point If you keep doing that, you'll end up realizing That you completely missed the point. And that when you make enough money, you use that money to give you back your time.

26:33 one of the things back to this point of thirty nine and fifty seven. I was big into time and That's why we have all these principles around time and how do I think about compounding time and all these things that are kinda weird, but In the last couple of years I realized that Time is actually a subcomponent of something more interesting or more important, which is our energy.

26:52 I only want to invest my energy in things that give me multiple currencies back. And I'm very aware of my energy. If I'm with somebody and I feel like I drains my energy. It's like, you know what, I'm not doing that again. Or wow, I love my energy.

27:07 with this person in this situation, then you lean into that energy, right? So I'm very thoughtful of today is like I just want good energy in my life. As someone that just tweaked my lower back, likely due to my rising age. How have your views on your body changed? I think the body it's like heart. Heart disease starts in your twenties.

27:26 It doesn't show up until your fifties. And heart specifically, for example, there's nothing you can do to reverse it, you can slow it down. We abuse our bodies because we can take it. But once you get into Forty five, fifty, fifty five. The same thing that's happening to your thinning hair or to

27:44 Whatever it is on your body. It's happening to your organs. It's happening to everything. You and I are both friends with Peter or Tia, but I really want to live. Really well.

27:55 I wanna age as well as I can given the gene code I got. And for that I need to take care of myself. So I'm probably fifty pounds lighter than I was when my kids were born. And it's been a five pounds a year for the better part of ten years. I want to enjoy my life at the end.

28:11 But not for any other reason. I don't want to be the healthiest guy in the cemetery either. I think life is to be enjoyed and balanced and all those things. Can you draw the contrast between good and well? That's my favorite new thought. I think

28:23 In life things are good. Like people oh I'm good or business is good and all these things and that's okay. That's a reflection of externalities or what's happening in the world. I've been through some.

28:35 pretty difficult personal things in the last couple of years. And I have found the notion of people will ask me how are things Uh they're good. And I'm like, I'm I'm lying. They're not good. They're horrible. They're actually really, really not good. And what I realized, but even though they were not good. I felt well. I felt well because I was dealing with all the circumstances in the best way I could.

28:59 And I was finding a tremendous amount of Insight and peacefulness. in that growth that I was having on how I was showing up and I realized, wow. This is what the part of well being comes from.

29:11 If you think about well being It's really two different words. Because they're connected when we say them, they we think about it as one thing. And if you look at the definition of well being, it makes no sense. It's like double talk. But if you sti couple those two words

29:25 Will. Is actually that feeling that you get a peacefulness inside, that connection to your soul, that sense that you are showing up the way you want to show up, that you're in control, that you're your own best friend. Yeah.

29:38 No matter what's happening in the world. Nothing. can change that feeling inside. And that to me has been the biggest realization of the last two years. It's like I am really well.

29:50 And I am well because You know what? I'm kind to myself. I like my life. I do the best I can. I screw up all the time, I laugh on myself. And then being is the one that I find

30:01 So interesting. We were talking about goals and no goals and the value of goals and Think about another one is like We spend all our time doing things. We have to do list.

30:12 Everything is a do. Society rewards us. for accomplishing things, for four hundred and fifty podcasts, for this and that, that's doing And what you realise when you get to my age is like Being, it's like a much better state of mind. Being is a place where there's nothing to do, where you're actually doing things for no reason at all.

30:32 You're doing it because you feel connected to whatever it is. And it's really hard. When you spend a hundred and ten percent of your time Doing. To find the muscle and find the space. To start being and well being is a place where you feel

30:47 Really settle inside and you spend the time you want, just feeling connected to whatever you want to be connected to. And you suspend all the societal bullshit. That we give so much power to. That manipulates the way that we think the world wants us to show up.

31:03 So to me this is like a really interesting journey and I think I'm Early in this journey. My hope is in the next ten, twenty years just die peacefully we'll be understanding that I became super clear on how to live life.

31:17 The way that I think my soul was intended to live. How would you assess A peer group, let's say a group of financially successful people that appear on the covers of magazines or something. How many of them are well or thinking about this?

31:30 I don't know many people that are well. I think everybody's on a journey. But You and I know a lot of people that are in those magazines. And it's not that they don't have well moments and it's not like their good is a bad thing either. But it's just really hard for our egos.

31:44 It's really hard for what others may say of us, it's really hard for society's value to put on us. Not to affect us. And the fact that you're in the cover of a magazine tells you something. Vanity is life's greatest sin.

31:58 Little bit of this, you gotta decide what it is, but it can become you. You can't put that inside of you and I think we're all in some struggle in some journey. To find our connection to ourselves.

32:10 And crisis usually reveals that. And that was to me the big transition for me is this crisis is giving me a perspective of like True. appreciation of the really nice things you and I get to do every day. The rest will come and go.

32:25 You were in a very high profile crisis once. In the plane that Sully landed on The Hudson River. I think in the front row seat. Can you describe the last five minutes of that experience?

32:35 The experience I think was three and a half minutes. So I should say I think it like little. Look, it's the greatest gift one can get. It's the greatest gift to know that you're gonna die. Were you certain of that? A hundred percent certain. It was either I'm gonna Blow up.

32:52 And that will be a lot better than breaking into pieces in January fifteenth in the Hudson River in New York and freezing in forty seconds. If g we're given those two options, I think blowing up is better. And then you have ninety seconds to say goodbye to your life. With no suffering. Zero suffering.

33:09 And then On the other side of this No one dies. So you can talk about it and celebrate it and understand it at a time where our country was in incredible crisis. We were coming out of the financial crisis of well wait.

33:22 This country was in a low place looking for a story. So we were really lucky that we had the most incredible pilots. on that seat that day, that in many ways, and we can talk about him, he been preparing for that moment his whole life. He was a gliding instructor. Later on I've gotten to know him really well and

33:40 You say you're only a pilot when you lose an engine. Otherwise you're just managing the autopilot or whatever the inputs in the computer. And that day it was a New York whole day. I was coming home to Charlotte My biggest concern was landing and coaching my son's basketball practice. And as we take off, there's a large explosion in the plane.

34:00 Bam! half asleep as you're taken up. You realize I look at the flight attendant and I'm in one D, so I can see the flight attendant. There's nothing in their face. Just like annoyance of like there's gonna be uh whatever because we turn the plane right away again. Nothing is happening.

34:16 Smoke is coming in. You can hear the engine struggling, but you think we're just gonna go back landing. We're not that high. Probably three, four thousand feet high. And then all of a sudden Sully gets on the microphone and says, This is your captain. So he identifies himself and he says three words. The only three words she said, and this was the moment.

34:34 He says, Brace for impact. The movie is actually very true to a lot of it, especially to this. But at that moment I look back at the flight attendant, Patrick, and

34:43 Then all of a sudden it's complete terror in her eyes. She's like, Holy cow, in training, this is we are not landing at an airport. I don't know that, but I can see her eyes and I know that that's what it means. And the great gift of that day was ninety seconds to literally say It's over. I am sitting there going like oh my goodness.

35:03 It's over. Not only is it over and then some people you may have a a near death experience of a second or Two seconds. This is a minute and a half. to basically sign off. From life.

35:14 And that's for me been super formative. Previous to this last year and a half. It was a real moment of kind of resignation like And lots of things happen from How have I dealt with

35:28 spiritual b beliefs from that time all the way to how it did impact my life. And I did that Ted Talk. Not knowing that it would ever get published. But by the way, it was the greatest gift I give myself because people talk about it. And it's a reminder of me of a promise I made my to myself that day, which is I was not gonna let that experience

35:46 Some day I want it to be a part of me, not something that Happen to me. I try to live very hard, but very consciously of the gift I got that day. Can you remember sequentially what went through your head?

35:59 In those ninety seconds. Yeah. When I think about it and I think about it now more evolved. But time behind is A lot of it had to do with the immediate emotion that I felt was just Oh no, it's over.

36:12 It's this sense of real regret. that it's over and there were so many things I had left undone. It all changed in an instant. Life changes in an instant. We all have had friends that things have happened to in an instant. And

36:27 I think in our evolution We're unable To process that. 'Cause we would have never left the cave. If we felt that, right? So there's this

36:36 concept called hedonic adaptation. that we will adapt to whatever situation and that's what life is about. We have adopted this thing. And that was for me This notion of gosh. when the plane landed, I'm I am gonna live.

36:49 With intense purpose every day. I am gonna ask for forgiveness the moment I do something wrong. I'm gonna drink. My best wines whenever the person is there. I'm gonna say I love you. to anybody I love. I am going to try my very best.

37:06 every day to try to like not regret. not doing or saying something. And that was wonderful. So I live out loud, so to speak. 'Cause I know it's gonna change in an instant. Tomorrow, maybe that instant and

37:18 I'm not having that regret if it happens. The second thing that I thought about it was like You go into super human, right? Your adrenaline is shooting, you're in survival mode, you're gonna die. There was this sense of

37:30 Almost embarrassment. Of how much I had allowed My ego. to be who showed up in the world.

37:38 how much I had spent energy being wrong by people. Or being more or less than better or worse than How much my ego played a role in how I showed up every day.

37:52 And it was this notion that You know what? I hate it. I hated what that meant and that I didn't realise that that was a mask. That I was putting on. And that I didn't need to have that mask on. That eagle started with

38:05 Okay, where does that come from? And for me, Patrick, was a lot of learning I have this moment when the plane is gonna crash. We talked about religion a bit today and I don't share this a lot. I don't know how people take it, but

38:16 I asked myself. Okay, do I buy? Insurance. I can ask for forgiveness. I was raised Catholic. I can ask for insurance right now.

38:26 And for sure, if there is such a thing, and I was not I'm not a practicing Catholic, or wasn't at the time a practicing Catholic. I am not because I'm not a hypocrite. I may be all flawed in many ways, but it's not that and it just seemed feel natural to me. And what happened as a result of to me after that, after just

38:44 saying, Hey, this is who I am. Is I let go of all guilt. Not that I don't take responsibility, but the forgiveness happened to myself at the moment. It's like I no longer Had this notion, and I think guilt drives

38:58 a lot of our ego. A lot of our comparison set, a lot of this notion of having to be right. versus choosing to be happy. And look, this is not a perfect journey and at times your ego gets caught up in this and your ego gets in the way. Trust me.

39:13 Compared to when this happened. I am Incredibly Incredibly lighter. I don't want to die and I don't want the ego to be the one that shows up every day.

39:24 And as a result, the problem that what happens when you have tremendous forgiveness for yourself. One. Your conversation with yourself changes. You become incredibly kind. You become a lot more light.

39:36 But you then find forgiveness in everything. I am super, super forgiving. And to me true forgiveness, and there's many definitions It's when you forgive when the other person Doesn't apologize. 'Cause the forgiveness comes from love.

39:50 And comes from a language of accepting the humanity of all of us. That was to me super liberating. At the time it was come on that's a regret. All of this were regrets. And maybe the last one as this plane is about to crash and you know, when you fly you can count down when we're gonna hit the water and you're like, Okay Please blow up kind of thing. I really had this thought is wow.

40:12 I was not scared. And I thought it would be super scary. And I was certain. And the feeling was actually sadness. The feeling was

40:21 Somehow. I had Miss my opportunity. To leave my mark in this world. I had not focus on whatever my purpose was meant to be.

40:32 I was so busy Accumulating. Doing the things that society asked me to do. uh I have forgotten that I actually

40:41 can leave this place, this world a little better than I Found it. for my existence and to me that's the only meaning of light. And that manifested itself on like my kids. I really

40:52 Justify myself being A light. five percent of the parenting my wife carried the Load and she did an incredible job. But I

41:00 feel like oh I'm doing this side of the equation and she does that side of the equation and I was like I've changed. Dramatically. My relationship with my kids right now is fantastic. Because I realize that that to me is my purpose.

41:13 But my purpose. Is also this business. I am here twenty four years later and as engaged as I am because I believe that this place is a place of good. Is a place of good where you come here.

41:25 You get invested in, you get trained, you graduate, you do go great things. And hopefully you do it in a way that Is honorable and ethical. And purposeful. I believe that all this random success I've had.

41:37 Because it's more random than not. It's an opportunity to actually put it back into the system in ways. I'm reconnecting with Puerto Rico in the most beautiful ways. What a privilege. It's my purpose. To put it all back in.

41:51 So for me, life has become really, really simple. That was kind of my last ten years until the last two. Until the next challenge comes. That's what life is about. The contrast of our challenges is what makes our growth.

42:05 Feel meaningful. You've teed me up. Please tell the entire story of turning this basketball team in Puerto Rico around. Oh that's a nutty story. Really? We're gonna go there. Little bit of context.

42:17 Yeah. Hurricane Maria was I think it's seven years coming up now, six or seven years from After Hurricane Maria. If you're Puerto Rican. You're

42:26 Really love your island. And I found this really interesting. A lot of people ask me, Oh, are you Puerto Rican or you're American? I'm like I am both. I'm not a percentage. I'm a hundred percent both. And I'm really happy to be both a hundred percent. I get two things out of this. Um

42:40 But like many other Puerto Ricans that were in the mainland and had some resources, you felt compelled to help. We raised a bunch of money and flew a plane full of stuff. And I took a lot of my friends, we got them four by fours and we got into the mounts and we were delivering baby formula and medicines and all those things and feeling really good about ourselves. our eagles were super healthy that we were saving

43:02 Nothing. And I got back on the plane coming back and I'm like, I am such a hypocrite. I literally have been looking for an opportunity to reconnect with my island. I'm here today and I'm feeling really good because I deliver boxes. It's like if you're really, really gonna do something, this is the moment.

43:18 So I came back and Organize our comps team and they always get scary because I have an idea is code for like oh no. And because a lot of them are bad ones. But I said I have an idea. And we made this massive pledge that we were gonna move Puerto Ricans back, that we were gonna create real employment in Puerto Rico, that we were gonna pay US salaries that we're gonna train people on fast forward a journey. And we have five companies in Puerto Rico with hundreds of employees disrupting banking, disrupting media.

43:46 Really a phenomenal and it's a movement. It's not even a company. All the CEOs A little bit of a different orc design there than we have Here or in the UK And it's been beautiful. I reconnected with my island and I left Puerto Rico or I didn't go back after college.

44:02 Because he was too small. That little highland. And I'm falling in love with the island because it's too small. And you actually can do something, right? And We're involved in like rewriting laws that are good for the island or helping entrepreneurs and investing in things. And I'm finding insane purpose on this. I love Charlotte. I love Puerto Rico. I can be both. So I can see myself just being a part of that and helping people that need either courage or capital.

44:26 Or conviction. To go to something bigger. And it's this beautiful movement call forward seven eight seven that we just are all a part of and it's authorless and all of that. Well, it's part of that. Now that's preamble to this thing. I love all that. Oh my high school buddies and we were all we still all get together and we're that age again and We all love hoops, and the inside story is I always love hoops more than they love me.

44:51 I was pigeon toe. I'm super tall. I really uh almost never made any good team. I was always in the B team. I sometimes made the C team. That was really horrendous, but As I grew into my teenage, I got better and I started working at it and it became like one of those things where I recognize effort to Growth and reward and I got better and better and better in

45:14 I literally was the last cut of a semi pro team my senior year in high school. Um The assistant coach was my high school coach. So maybe that's why I was the last cot and not the first cot, but I was there and I belonged. And then I got was getting paid like a hundred bucks a week. I was a professional. And I loved it. And by the way, it was the best thing that happened to me because then I went and study and I that's when I left for the US. But I've always loved the game and I love it here. Sit next to the Hornet's bench. I'm good friends with like five coaches in the NBA that I talk to all the time. I know oh I know everybody. It's a language for me. It's one of the most beautiful language, language. College basketball, I know all these guys and I love it. And there's no currency other than love.

45:51 And so my buddies are like, Man, the league in Puerto Rico's so good. We should buy a team. I'm like, I need one more thing, like I need a root canal. Zero point zero chance. And they're like They're like, Come on, man, we can afford it. We can afford it. Come on, we'll we'll do all the work and and we will go drinking and like All right, go look if there's a team we can buy. Like Bad Bunny owns a team, Rosuna owns a team, and Molina owns a team. And it's like it's really bad, it's really good basketball. Yeah, but super competitive. And I'm like cheese, and then all of a sudden we found a team. And then all of a sudden the team is too far. I'm like, I'm not driving an hour and a half for a game. It has to be in San Juan. I'm like setting the most incredible boundary. So they found a team that we can move to San Juan. And we got play at a little volleyball court for three years. Well, the Bill is a court and it's the worst team has never made the playoffs.

46:39 Decent enough guy, but he couldn't afford the team, so we ended up buying the team. We bought it a year ago. And I'm like I have no time. I'm not doing anything. It's been the greatest for you.

46:50 Fast forward tomorrow. So that team has never made the playoffs. There were three polls at the beginning of the season. We were ranked twelve. Eleven and twelve. There's twelve teams in the league. Like we were the easy game in everybody's schedule. Fast forward. We are playing game seven.

47:07 Of the finals. Tomorrow night. And it's been The craziest, most fun ride. And you know what I realized, Patrick?

47:16 I had never own a toy as an adult. A toy where you literally do it for the pleasure of it. And the connections, the ability to bring f a philosophical approach to this, the relationships, running it in a very different way, investing differently. The biggest compliment is our best players all came through the in the middle of the season not winning the final, say, This is my favorite team I've ever been a part of. And it's all culture.

47:43 At the end of the day, Patrick. We all wanna belong. to places that we feel connected to. And the magic of organizations is understanding that. And in this world.

47:54 We are so disconnected from so many things. People no longer belong to civic groups or churches or all of this. in the ability to create connections. Look, this town is going crazy. Win or loss, it did lose, it doesn't matter. It's like I so good. Like if you go through the year

48:12 Go back to your calendar and say, What are the things that I'm gonna remember? Ten years from now. You'll be shocked how few they are. If you're lucky you have Six seven.

48:22 usually experiences Usually things that Are either surprising and it involves different things. And it's a really good exercise to do because you're like, Okay, how do I do more of those? Yeah. I need to design that into my calendar. I tell you I have like three of them that are gonna show up at the end of the year, including

48:37 Two nights ago when we're down ten with two and a half minutes. Game six on the road. We send it to overtime. We go to double overtime and we win. I can't sleep the whole night. I have a leadership meeting. Yes, they Which I am completely Exhausted for and it was the greatest thing ever. So it's pretty good. So tell me what you did.

48:55 How did the culture change? What is the culture of the team? Like I went and asked everybody, And don't shortchange yourself. Like someone told me that You called and we're talking in the locker room to every player one on one. You are involved. This is not something that you're just phoning in. I've been in Puerto Rico nine times and I can literally go hold down for two games and run back, so I just give so much joy out of it.

49:17 It's just uncomfortable to talk about but okay, just to give you a little bit. The first practice we show up, all these players are looking at like okay, a new owner players don't trust owners. They get treated like merchandise, they get lied to, they get all this stuff.

49:32 They're very skeptical. So you can't show up and say, Hey, we're gonna build a culture of this and that and the other. So I showed up and said, Look, there's literally three rules here. We are gonna invest in you. So that you can make more money out of your career here or anywhere. And here's what that means.

49:49 We put in a full weight room, we put a bunch of staff. They're looking at us like a little bit like incredulous. It's like we're gonna do this. Number two is We're actually not gonna care. about

50:00 A goal teams have goals. You know, this is someone saying Franchises have systems. We're gonna build a system and we're gonna play in a certain way and we're gonna do certain things. And then

50:10 There's nobody that is above the team. So this is a team first and all of that and we've extrapolated a lot of this and We sign a big free agent. I think it was two or three days later we fire him. Because he was a jerk.

50:22 Culture's what you tolerate. It's not what you preach. My best player. We suspend it. And never told anybody because he was not behaving in a way that was culture fest. He begged to come back. He's the most amazing teammate. This guy says I've never been part of a team. These kids get treated like whatever. So

50:39 Great teams. Great teams in anything in life. It is Team first. 'Cause most places are player first.

50:47 Exceptional teams that where they exceed their expectations where where we are we are like the eighth best team. Not the second or first best team. Is when there's teammates first. This guy's The love that they feel for each other

51:00 It's beautiful. And the great thing about teams, back to community. It's like Once you are part of an experience like that. The team will end.

51:08 You will be teammates for life. And that to me is the beautiful part of all of this. Regardless how the story ends, and this may have been our lucky season, we may never make it again. It does not matter. No one there's a saying in Spanish No me puedes quitar lo bailado, nadie me quita lo bailado, que quiere decir you can never take away the songs I've danced.

51:28 We go to the games, all my friends are sitting in the French role. Like it is literally a reunion of high school there, and it's just beautiful. This is beautiful. Towns are so passionate. It's crazy the love that they have for the game. There's a parade on Saturday to celebrate our championship. I hope we win. How could I watch this game? Okay. It'll watch it.

51:48 There were like fifty thousand people on YouTube in the US watching the last one. Incredible. Oh man, I hope you win. But it doesn't matter, like he said. It doesn't matter. It's a game. There's no winning. We won already. It lets me jump. Back to our list.

52:01 Thirty nine to fifty seven. On Leadership. And I was thinking about this as you were talking about Sully. And how to characterize him.

52:10 And he seems like an incredibly Quiet, humble professional. I don't know. If he would call himself a leader, I don't know what that means. Lots of good sounding definitions about it.

52:21 But rather than ask you like to define it. or versions of it that you've seen. I'm actually more curious in how you think It's changed for you in that eighteen year period. It changes a lot.

52:32 I'm surprised at how many things I was convicted of. That I've changed my mind on. Part of it. Maybe chemical. Part of it maybe experience.

52:43 Part of it is you realize at the end of the day What is it that matters and all that? I think leadership First of all Title is not leadership.

52:52 Role is not leadership. Other people decide if you're a leader or not. It's not something that you have, it's something you earn. And I think that's something that you gotta take really, really Personal. Now, that doesn't mean that they're that good leaders are not like to respect it.

53:07 And they're respect it for being consistent, being clear, being fair. giving, being all the things that matter, kind and all this different things, but leadership to me is It's a way you show up every day. And it starts with personal leadership. I don't think you can be a leader in the world if you don't have control of yourself.

53:24 You don't really understand yourself and then It's an imperfect art and uh you're constantly growing and learning and We had a staff meeting yesterday in the morning, you know, that thing was fantastic and in the afternoon How didn't show up that great? And I was exhausted from that silly game and I was sure for you. I was like I got in the car like ah that wasn't my best performance and then I laughed and then

53:46 I'll own it and move on. Leadership a lot of is how you show what it is to be human. lot of leaders feel like they have to pretend to be Perfect. And look, we all have insecurities, we all have challenges.

54:00 And to me leaders is showing the way of Humanity of How to do growth and how to care for others and How to do things that matter.

54:09 This is a very strange question to ask an extremely successful business person. Do you like business? I Love. The game of influencing.

54:20 I'm very influenceable. I listen to your stuff and I'm influenced by it. Today we had a great conversation and I'm like I am the evidence so The business of making money? Fine. It's a score that is kinda silly. The business of bringing people together to a common goal or to a purpose.

54:38 To compete? to try to figure something out to struggle to fall. To not be sure. That's really fun. So I think to me business is just a

54:48 platform for those elements to happen. In my house. My older sister's super smart. So I was never gonna be the smartest. My younger sister's a great athlete.

54:59 So I wasn't gonna be great out. My brother's super handsome. I showed up literally in my house. I'm like, I am never gonna win anything in my own house. So I gave up really early this. Like I look at there's a lot of incredible entrepreneurs that are doing incredible things and inventing incredible things and I don't feel neither envy Nor anything. I feel like that's their thing. This is my thing. It's a weird question, never been asked Do I love this system? My default answer would have been of course.

55:24 'Cause I sold avocados on Streetlight when I was eleven. But what I really liked was being independent. I'm not really sure that business was what I wanted. Yeah. What was the key to selling avocados? Getting them really cheap at the farm and then you know, low cost provider. Exactly. You described earlier we were for fun going through our decades and

55:44 Trying to label the decades a little bit with like a word or two. You said for your thirties that courage was the word. Yeah, it's an interesting word. And that for your twenties it was confidence.

55:54 Can you describe why courage? I found that so interesting. Actually wanna on the answer confidence because confidence goes into courage. Yeah, I think you need that confidence. So look, I'm twenty. I'm a sophomore in college. I don't know much English. I'm an accounting major, so I don't have to speak. I'm in a really cold place in Boston. I feel weird. I dress different. I speak different. I act different. I'm Puerto Rican.

56:16 And actually that was really good to feel that I'm working all sorts of jobs. I drive a limo, I do the things that people do in college and like And for me, I graduated, I'm like, Okay, what am I gonna do? My dad was an OBGYN, so I couldn't go back to his practice. I was like, okay, and I ended up in Japan. And I go to Japan and I'm like, holy cow, there's no internet, there's no anything. I struggle. I was lonely. I figure out a way to take a six month assignment, stay two years out with general

56:42 Electric at the time. And all of a sudden I'm like, I should just apply to Harvard Business School. They're not gonna take me, but You know what, who knows? And that's the only place I apply and all of a sudden I forgot I apply, I get a letter. It's like do you remember a class of ninety for I'm like, Holy cow, they met me in So I'm like whatever, twenty six, and I get to hire thinking I'm definitely not gonna make it.

57:00 I'm gonna be one of the ten percent that fills the screen. I literally spent my first month Smarter, smarter, yeah, dumber. Smarter, smarter. I'm trying to figure out. And I realized like, you know what, everybody's the same. So I got confidence like I could compete in any level. I can compete in college. I can compete in Japan. I can be okay, I can figure it out, I have tools. And I got a lot of confidence and I finish business school and everybody was going to McKinsey or investment banking. I'm like, you know what? I've always kind of listened to a different radio station than most. And I always knew I wanted.

57:30 To run a business, start a business. I wanted to be independent. I have a story, my grandpa someday I'll tell you, but that was my vision to be independent. And I was like, I'm gonna learn. A professor told me, If that's what you want, go and learn on someone else's nickel. And that's what I did, and that's where I met Dan. That's where I met Brenda, my wife, and you know, at thirty Which is to change a decade. So that's when like little I got married and basically we started the business. So the twenties was the place where I like look, I belong anywhere. I'm not better than anybody, but I'm not worse than anybody. And to this day I show up and like held these meetings and I kinda laugh. I'm like, How in the world did I end up in this room, I'm sure sometimes

58:04 That happens to you right out, Joe. I start singing my hate one of us, it's not like the others. It's just everybody's the same. No one above, no one below. So the thirties A little bit of this is We struggle, we struggle in there m losing all this pregnancies was really, really hard on our marriage and we were this close

58:24 So quitting and going down a path of building our family in a different way took it a lot of courage and not quitting the business took a lot of courage and borrowing money from my dad to live for a couple of years after we depleted the little we have took a lot of courage and Hustling our way. every day for a long time convincing people like I was like holy cow ignorance is a bliss

58:48 And necessity is actually A really driving factor. See, it wasn't until forty that I would say, Okay We're gonna be okay even if it's at a level that is Not good enough.

59:01 I build a lot of courage. I'm like, you know what? I'll go for anything. With a little look and The right people around you, anything can happen. Can you tell me about your grandfather? I never met my grandpa. It was my dad's dad.

59:11 By all accounts he was much older than my grandma. Is Lebanese. came to Puerto Rico on a boat when he was a little kid. There was an epidemic. The boat was going somewhere else, stopped in Puerto Rico, pushed everybody out of the boat. He ended up

59:24 growing up partly in Puerto B in Lebanon, Christian Lebanese, and then he came back in his twenties to Puerto Rico and became one of the most successful People that the stories of my grandpa was like twenty servants in the house, one of the big mansions, and he was basically hit corner of the market for all vegetables. Imported everything, set the price, stories of predatory pricing, beautiful like this crazy stories of

59:47 all the things he was. I again I never met him. There's a lot of this um mythology. Which I understand. But what was really interesting, I think in his fifties he got Alzheimer's, really early Alzheimer's. And all of a sudden the government realized he never paid his taxes. Or a lot of his taxes.

1:00:03 I imagine he's like looking that money belongs to me, not to the government. So they took everything away. So my dad and his teams went from like the wealthiest Ten families to nothing. And to this day my dad pays for anything cash. That was so riveting. So we will have these family dinners and big Hispanic Lebanese families. There's thirty people at the table, right? You're the little kid and inevitably

1:00:25 The story will always go to my grandpa. And the stories were always like this incredible guy who was Bigger than whatever, and then they always ended in a murmur. The shame of how the family ended and I saw my grandma tell the stories and everybody and I think I was a little kid and I didn't realize this until much later.

1:00:42 And it's interesting the stories. And by the way, it may be a story I'm telling myself. That's okay, it helps me. It's amazing the the things that we carry in our lives. So I show up And I realized that a lot of what I've been trying to do, I'm super close to my dad, super close to my mom. I just really want it.

1:00:59 them to feel proud of our family. I wanted to do what my grandpa did. But do it in a way that Well ethical and my family could be proud of my grandpa. Through the work that I was doing.

1:01:12 Um I only realize this when I was with my dad and he goes, You are just like your grandpa. I was like, holy shit. It picked me. I think pick this. It's like this is a random roulette. They're just

1:01:23 It's the gene pool of I got my grandpa's gene of being a merchant. Fast forward a number of years. And you and I were on a walk. And you said something to me.

1:01:32 Which was something to the effect of Be careful about The relentless pursuit of more. Thinking of that in contrast to the story you just told.

1:01:40 Yeah. Maybe Say a bit more about That idea. Hit me kinda hard.

1:01:46 society sets us up on a trick. Although this is a mirage. Every time you l get to a peak, you'll see higher peaks. There's nothing about a peak that matters. Sometimes it's overset about the journey and this and the other. It's that inner peace. It's that sense of well being that really matters.

1:02:03 How many days of your life? Do you have a sense of calm and peacefulness and purpose? And your in a good place, you feel like your energy is in a good place to me, that's what really matters and

1:02:14 The pursuit of more robs you from that. You can't take it with you. It becomes a responsibility the more you have and I tell this to a lot of our employees when They're leaving and I said, Okay, great, you're ready to graduate. I'm for you.

1:02:28 But when they're replacing happy with happier. That's when they get in trouble. There's no such thing. I have a fun exchange. An employee came in and I was Ah you're back great. We have a bunch of boomerangs. It's silly how many boomerangs we have.

1:02:41 And I'm like, you're back as again. I jokingly said, Hey, the grass wasn't greener. He goes, No, I like this brown. It's true, everything is a little brown. I've Stop pursuing more. That's why Anything I do from here on out with my Capital

1:02:57 the return on the capital. I don't invest any more on funds. I don't invest in anything. I don't want to compound capital. I know that sounds like opposite of what you would ever think. I want to use my capital to compound other things that matter to me. So I'm using my capital in Puerto Rico to do things that really matter to me. This whole notion of purpose.

1:03:14 my original purpose is through my kids, is through my friends, is through my community, but like then I am incredibly privileged. to broaden that purpose to things that Are good for society. That's all that matters. Mm-hmm. Capital for capital what?

1:03:28 You're never gonna be Beezos or whoever else. Like that's a silly game. You flip something around. On me earlier today that was really interesting around this idea of like ninety ten in a conversation.

1:03:40 Where I think maybe you and I are both tend to really be curious about other people and ask a million questions and very often finish a conversation having only spoken ten percent of the time or something like that. Which I guess I've always thought is like a nice thing to do for somebody else, like be Genuinely curious about them.

1:03:57 Like to think I'm that way. But you had a different perspective on this. Can you explain that? Look. Somebody that is looking for love, the best thing that you can do is ask a lot of questions because people love people that

1:04:08 Listen to them. You can ingratiate yourself. Surely to somebody who says oh well How good. It was wonderful. It's because you talked a lot about yourself. That's it.

1:04:18 One of the beauties of true friendships. is allowing the other party to feel that they can love you back. And I tell you the story of a dear friend of mine. one of my best best friends it's like my first

1:04:32 best friend in the US. His name was John Woods. He passed A number of years ago, John was a little older but still kind of in college with me, was someone who worked in a study And one day, many years later, I have dinner with him in Boston and his wife is also a great friend of mine, and she goes back and asks him a bunch of questions about me and he had no answer. He literally called me the next day. Dead serious. This is one of the guys that was like

1:04:55 Most fun, jovial guys. He calls me to fire me. As his friend. I was in his wedding party. He was in my wedding party. We're like brothers. And he wasn't kidding. At first I thought this is really I just saw you last night. We drank two bottles of wine. We like literally told each other we love each other. And you're firing me the next day?

1:05:12 And he said, You are the most selfish friend I have. I think. You just talk for ninety percent of the time. I just I bought dinner. I like what else can I do, right? Niggas.

1:05:23 You don't Ever let anybody else love you back. And you'd suck all the love out of every interaction. Because that's how you feel good about yourself. And I don't want to be friends with somebody who is not.

1:05:36 Able. to be a receiver. And it was Holy Cow.

1:05:42 At the time I'm like wow, this guy went noony and then the more I thought about it, the more true it is. I used to be in the place I always picked up every tap. That's selfish. letting people in, your true friends, I now share my struggles the last two years. I literally Wait, I would I would because

1:05:59 In part. What I was doing was Letting them love me. By me loving them, right? It's like it's this language of trust. It's the language I'm like I'm very open with people that I trust. 'Cause it's what friendships are about.

1:06:11 And that's how we get helped. And I think a lot of people are out there feeling lonely, feeling like I can't share well If there's somebody out there that you think loves you, give'em a chance. To love you back. How do you recruit people here?

1:06:23 Like just shaking hands and talking to some people. Couple hours ago. You get this incredible sense of Excitement to be here. Front footedness.

1:06:33 So what are you looking for in The people that you bring To red ventures. I think part of that Is who you bring here, so I think you're making sure that

1:06:44 People are comfortable with the way we operate. If you need certainty, if you need predictability. If you need to be the star of the team, if you have all this stuff, it's not gonna work. But we recruit so many young people, which that's really usually not the case. I compare it more to Charlotte, one of the things I love.

1:07:03 about Charlotte is it's probably one of the greatest places to live. Not just because of the weather or the airport or whatever. It's because people are super nice. People here drive nice. And whatever else. You take a New Yorker and you move into Charlotte, and within a month they're saying good morning to you. So the culture of Charlotte is what People come in and because you feel rude, you go to the third coffee shop in a week and you you walk in and they say good morning and you're like, What do you want? Right? And what you realize that that's culture.

1:07:31 So in here ultimately people behave in a way. So when you walk in You're like oh These are the norms on how you behave here, and all of a sudden becomes like ah. This is how I fit in.

1:07:43 And it becomes The way that we operate with each other. We take our work really seriously, not ourselves. There's a ton of humor. We do a lot of things. We have tons of sports, we have tons of stuff just because It's all interconnected.

1:07:57 If you think about The investing side of your brain or world. I kinda have the same stupid question I have about investing that I did about business. In some sense you seem like someone that's just intuitively good at this. Like yeah, you buy the avocados for a twentieth of the price you sell'em, like you make money. But do you have like an investing philosophy? Cause part of what you've done is like allocate a lot of capital.

1:08:17 Yeah, some Very basic way, like you're an investor. I'm curious. What do you think makes you good at it? And what you like about it.

1:08:25 I love To bet I hate to gamble. And I think life is about Understanding odds and edges and risks and this whole notion of

1:08:35 Can you win multiple ways also applies? On the other side. When I look at a business model If the business has Three variables.

1:08:44 For it to work. I will never invest in it. There's some great businesses that need three barriers, but they're gonna need a ton of capital, a ton of luck. They're gonna have to figure some stuff. If the business has two variables Then you're compounding the risk, so you better be fairly certain that one of those variables

1:09:00 you have high confidence on and the other one you have some visibility. And if the business has one variable and you have an inkling, lean right in. So a lot of this is just decompose risk. of what you're investing in. And it applies to everything. So it's both the multiplier and then the discount.

1:09:15 that you would apply to an intuitive decision. And when we see something We're like, Okay, that's worth the bit. But understanding that when you're betting you're gonna lose some. And if you're I think if anything

1:09:28 You need to have bad bets to be able to be a good better. Otherwise you're just taking fastballs eighty five miles an hour down to play. What episode Of Redventure's history.

1:09:40 Do you look back on with the most pride? We all have revisionist history. It's funny because we're getting a lot of momentum back and a lot of things are happening that are on the positive side, but Still there's this sense of Man, this are not the same days that it used to be.

1:09:57 And of course they're not. Everything Danny Meyer, a good friend of both of ours, says they cultures are like sharks. They have to keep swimming to survive. And to compare it to something first. I don't think the past is always as good as we remember it being. But the reality is that there was a moment in our journey where I remember

1:10:15 leaving a big company event here on campus and it was like a magical night and we had this like incredible energy and I got in the car and I'm like It just cannot get any better than this. To see couple thousand people just completely pulling in the same direction, trying to do something, and it was just felt like unity you couldn't

1:10:35 It was like lining in a bottle at a moment in time. And it was a moment in time. You felt it today. This is a magical place. There's a magical culture here. But comparatively, so probably when we're compounding it thirty percent for like five years in a row and were just success after success. It was like wow.

1:10:53 We're really good. Reality is we were really lucky when it we were really good. It was a matter of when that we needed to do it. I'm kinda very excited for the next five years. I spent a lot of time listening to your digestion of AI, but I think A. I'm really gonna change A lot of our businesses Some of the traditional ones, but even our

1:11:11 partner business or client business gonna really change and some of our assets. So I think the next five years may be the most exciting ones. And we're either going to get run over or we are going to play in it and we'll see. You described this evolution from the early days of performance marketing focus into businesses all over the world that do lots of different things. I know healthcare is one space that you're really interested in. We don't have to get into the specifics of the business, but if you want. Talk about what In that world.

1:11:36 seems like an opportunity and interesting to you. It does seem like such an important space and that's a very different world than the world you started in. We owned A bunch of really interesting assets. We own a bunch of assets that created a lot of both data and

1:11:51 Consumer's path. But you realize that those are kind of narrow businesses that exist for a period of time. We did this J V with United Healthcare who their CEO under Whitdy is a fantastic See, you're a fantastic human being and His view is that

1:12:07 the healthcare company of someday of the future, five, ten years from now, will be very much consumer driven, consumer led. And they need to be making that investment today because they are really good in the health plan side. They're really good in the provider side. They gotta get really good in the consumer side. And he is like, There's no way a company this big will ever figure that out. So I gotta find a clean environment where I can make sure that we're both investing, but I need the tech. I need the people, I need the alignment of incentives. So we did a long term partnership to go build this.

1:12:40 And it's been great. First year was typical Put two organisms together and Our joke was like look. We don't want

1:12:48 Our size and your speed. That will be a dis so that you get we get Our speed, your size. And that team is doing incredible work and we have some big bets that we're making and the next couple years she'll play out, but we're preparing for a future whirl. Healthcare is counterintuitive. the money in healthcare in very specific pockets, if you really think about it, there's not a lot of value. that has been sustained because where the money is given the government's putting the thumb on their scale with Medicare and all this different stuff, it's just really tricky.

1:13:18 And I think Doing it as part of The best and biggest. healthcare provider and platform out there in United Healthcare was the best way to do it. And so what is the North Star for the product in that business? What is the thing you're trying to deliver? Ultimately you want a place where the consumer gets All the answers, all the connectivity.

1:13:38 access to do I qualify for this thing? Is it cover? Is it not? It is preventive. And you can see how AI will play a role in a very personalized way. So It's almost like a agent. For you personally around your health. That because of HIPAA and all this kind of stuff, it has to exist inside an ecosystem.

1:13:56 This is not gonna be able to live out tight. And this is the largest platform to do inside of. You mentioned speed. One of the very popular ideas in the West Coast and start up land.

1:14:09 is You could beat anybody if you're fast enough. What do you think is the role Of speed. in business.

1:14:18 We used to call speed and then We ended up tripping ourselves because we were like speed through perfection. Well, there's some stuff you need perfection. Or there are times where if you're all speed, you burn a team. So we talk about two concepts as a iteration of that. One is pace. 'Cause pace is sustained speed. You see this marathon runners who go out and win the first mile and never finish a race. So you gotta understand pace and how do you bring an organization and the other one is

1:14:45 Not sprints. It's You're almost running intervals inside of a race. So when you can buy pace and intervals. We got a big push for the next sixty days. There we got different things. I think that's the sustainable piece.

1:14:58 speed part of this. I'm not sure that's right, but that's how we think about it. 'Cause otherwise you end up either in a body shop or people get burnt out or to what end and again it has to be Manage and purposeful. I do think that reps really matter.

1:15:12 And the ability to do this faster is how you can build better models, is how you can build better product, is how you can get to differentiation and when we go to big companies and our business model at the core is a B to B business. What we say to them, look, we have A platform. That

1:15:28 Allows you to grow. Faster than you're growing. And we're willing to get paid, only that is true. And part of that is because we can iterate in ways that you could never iterate. And if you give us the right APIs and the right controls, we are industrial great security, industrial great everything.

1:15:45 We may be able to help you. I think that's the key to this is we're servicing big companies that have to deal with a lot more than we do. Are there other any other Philosophies. that we haven't talked about that you feel like govern

1:15:59 A lot. Of your own behavior. There's a lot. I'm a cheap philosopher. Lots, lots and lots. There's lots around We haven't talked about our commitment to

1:16:09 real social impact as an organization. And the work that we do in Charlotte is probably the most outstanding work we do. We just don't publish it. By the way, we also don't believe that Like Simon Perez used to say Press and awards are like perfume.

1:16:26 Nice to smell and dangerous to swallow. Right. And those things get you caught in the wrong things. But We're so imperfect. And so in many ways. Naive.

1:16:36 I joked with you, I'm like forest gump running a business. Not sure what it is, and who cares? And I work really hard and I care really deeply, but Do we just Put weight on things that don't matter. If a high integrity

1:16:49 Builder. Or to come study. This place per year really have access. With the intent of I'm gonna go spend a year studying R V.

1:17:00 Then I'm gonna leave and I'm gonna start a platform. What do you most Wish that hypothetical person would take with them. At the core.

1:17:10 Uh But I hope We leave as our legacy. Is Thousands of people.

1:17:17 that were better at what they're doing and did more meaningful work wherever they went. Because they were here. And I can't tell you the amount of emails I get from people saying, Holy cow. I did not know I was this good. Because now I'm not competing against

1:17:32 everybody that is this good, and I would have never been this good. If I had not been there. I think that's really cool. That opportunity. One of the great things about our country is the apprenticeship layer that exists between twenty and thirty when you leave college, which I think it's at risk right now with all this not coming to the office and everything else.

1:17:51 And I think in the world of new tech and technology and digital, we're one of those great apprenticeship places. That's great. Businesses understood the greater good. It's not. We're gonna be bigger or more profitable because that ability to train people is what allows for innovation to happen and

1:18:06 Changes to happen. How do you do that? Like teach me how to do that. Like if someone has a desire, you mentioned the investment you make in the team, the investment in the literal team in Puerto Rico. Clearly you're really intentional about What that means. to do things or set standards. And I'm curious what it is. Is it systems of accountability? Is it ways of thinking about the customers?

1:18:26 What is it that you're investing and doing to imbue that? Yeah. people here. Okay, brass tax way. It is

1:18:34 Fifty factors. That have to play in. This is like an orchestra. It doesn't matter what it plays, it just has to be in harmony. So there is no song that says this does that is like All the instruments.

1:18:47 Recruiting. Performance reviews. Career tracking. Training. Management.

1:18:55 experiences, rotations Accountability access. talks like today where you had all this constant investment in people in their Personal growth. And we don't have it right. And we don't have it right at times. We don't have it right for everybody. But it's this endless pursuit of holding our mirrors to ourselves and saying,

1:19:13 Are we doing the right things? And this is a little bit of my struggle. Employees here are loving coming to campus, but they love coming to campus three days a week. Um If you're thirty and you're balancing three things in life and you are really good at why you do that, you're perfectly fine doing that. You can do your job.

1:19:30 That way. If you're twenty four And you don't know too much. I feel like we're robbing you from the experience of what it really means to get trained in this decade. So when you're thirty And you have fifty other demands, aging parents, a bunch of other responsibilities, kids and whatever else, you can actually allocate your time differently.

1:19:48 So I'm really curious as to ten years from now. what this is all gonna look like because We can see it. And you take that at scale?

1:19:56 And I think it's happening everywhere. apprenticeship of layer in the US is not just Companies is hospitals. Take anything, any practice. Super interesting.

1:20:06 Do you feel like the architect of all those things, those fifty things? Like is that something you wake up on a Saturday? No, we have incredible people. No. If anything I realize that I tend to ruin the soup when I put my spoon in it. Because You get too much credit. when you're the founder and you power is really dangerous.

1:20:27 And for a long time I didn't understand it. Honestly, I don't feel like I'm anybody's boss. I just feel like I showed up here first. But you can ruin someone's day if you don't Say hello the right way or whatever because They're invisible.

1:20:40 the same way you can make someone's day if you show up in the same way you can Completely. A lot of time now I'm disclosed. Look, I don't believe this. I'm gonna say it out loud just to see what you guys think, because if I say it without a disclosure, it's like Rick say we have to do this. And then we wake up six months later, what are we doing? They're like, Oh, you said it. I'm like, That's a horrible idea. I can't tell you the amount of times that an extraordin like me that thinks out loud is like, Holy cow, it's like you have now like everything is disclaimed. Just like you disclaim this is not personal advice for investment. And we have tremendous talent. Like I look the woman that runs comps here is just world class.

1:21:13 A lot of the Team that sits in our People capital operations are fantastic. They're the ones that are constantly doing this. We talked a lot about how you

1:21:21 have changed your view on things in the last eighteen years. What are you anticipating will change in the next ten? What has you excited about? The next time. Look, my role is gonna change.

1:21:32 I don't intend to be committing this much energy to this one thing. That's may not happen for the next three to four years. Hopefully the percho adventure's existing. I may not. go to Facebook or or Meta and drive out of their campus and you see the sun microsystems on the back of the sign. It's a great reminder that someone is gonna paint our building blue someday.

1:21:53 And that's okay. But it was meant to be for a period of time, so Yeah, I really don't know. And I think the Next ten years.

1:22:03 I think AI is gonna disrupt Every workflow. Every interface Every platform Everything in ways that no one can predict.

1:22:14 You gotta be both Aggressive And thoughtful. Remember early in AI people are like, Oh, this is just like the internet, but it is Four years you know, for maybe not.

1:22:25 Maybe it's gonna take that long for real models to mature, for consumer behaviors to change, for platforms to really adapt. All the money that got made and you know this better than anybody, all the money got that made in the internet wasn't in the first wave. Yeah, maybe some of the infrastructure. Rick, it has been so much fun. to get this excuse to talk to you about what you built.

1:22:44 Maybe more importantly, your philosophy for building it. I think you know my traditional closing question. What is the kindest thing that anyone's ever done for you? Yeah, in Fernandes, I knew this question was coming. There's been so much, but instead of finding the one person, I'll tell you the thing.

1:23:02 in his forgiveness. I have been forgiven. By many people. Ultimately for being human. I've been forgiven f by my wife for not being as committed.

1:23:12 in terms of being at home in that first decade of our kids. I've been forgiven by my kids. For not being that present the first day could have. There's no manual to run a company. There's no manual to do acquisition. I made a million mistakes and the grace that you give somebody when you

1:23:28 Forgive'em. It's the most beautiful things we do as humans. So I am super grateful for the grace of forgiveness. And it's a great reminder that that's a power we have to give others. That is probably what I take with me.

1:23:40 Coming here has been a total highlight of an otherwise fairly chaotic. Summer for me. You've created something. really envyable and inspiring here. Thank you so much for having me and thanks so much for your time. Incredible honor to be on your show.

1:23:55 If you enjoyed this episode, check out Join Colossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning. You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.

What you see above is a preview of the first minutes. One unlock costs 10 credits and covers this episode forever: full segment and word-level timestamps on this page, plus .txt, .srt, .vtt and word-level JSON downloads, as many times as you like.