Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS]

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Ric Elias is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guy, Bankrate, and large investments in a variety of other businesses across industries. He began the business in 2000 and has grown it to now a global company with thousands of employees. Ric walks us through the early struggles that have led to what is now a flourishing investing platform, but mostly this episode is a masterclass on cultural values and philosophies that transcend mere financial gain. We discuss the difference between living good and well, the power of forgiveness, and compounding more than just your capital. Ric’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 very moving. Please enjoy my conversation with Ric Elias. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by WorkOS. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit WorkOS to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @joincolossus ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:00) Meet Ric Elias (00:02:49) Chasing the Big Dream (00:05:38) Understanding Red Ventures: Origin and Evolution (00:10:25) Operational Success and Company Culture (00:25:30) Reflections on Money and Personal Well-being (00:28:49) The Difference between Good and Well (00:32:55) The Hudson River Plane Crash Experience (00:42:37) Reconnecting with Puerto Rico and Reviving the Basketball Team (00:45:07) Underdogs to Champions (00:48:09) How to Build Trust and Culture (00:52:29) Reflections on Leadership (00:56:12) The Role of Confidence and Courage (00:59:38) The Value of Family and Friendships (01:01:57) The Pursuit of Purpose Over Profit (01:06:52) Recruitment and Company Culture (01:10:07) Reflecting on Success (01:14:33) The Importance of Pace and Speed (01:16:23) Other Business Philosophies (01:23:17) The Kindest Thing

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Patrick O'Shaughnessy?

  Vanta automates compliance so your team can spend less time on security reviews and more time getting customers. Vanta cuts audit prep by 82% and gives you instant up to date proof of trust without all the manual work. So you can close deals faster and with less friction. Customers report a 526% return on investment and more than 16,000 companies use Vanta, including Ramp, Harvey and Snowflake. Get started with $1,000 off at vanta.com/invest. RidgeLine is the first end to end system of record with embedded AI for investment management firms running portfolio accounting, reconciliation, reporting, trading and compliance on one unified platform. Firms are moving off legacy technology and on to RidgeLine

• 0:45Patrick O'Shaughnessy?

  because of how far ahead RidgeLine's AI features are compared to anything else in investment management software. I've been hearing from a lot of investment managers about AI and they fall roughly into two camps with some unsure where to even start and others convinced that they can build their own order management system over a weekend. The reality is that running an investment firm will always require governance, controls and a single source of truth for your data and no amount of AI enthusiasm changes that requirement. RidgeLine is built on exactly that foundation, which is why I believe that the firms that come out ahead in the AI era will be the ones running on RidgeLine's unified platform. If you're serious about your firm's AI strategy, RidgeLine should be part of that conversation and you can request a demo at ridgeline.ai.

• 1:32Patrick O'Shaughnessy?

  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. If you enjoy these conversations and want to go deeper, check out Colossus Review, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus Review along with all of our podcasts at joincolossus.com.

• 1:57Speaker 01

  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 Sum. 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.

• 2:26Patrick O'Shaughnessy?

  Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of One conversations with N of One people. My 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 2000 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 masterclass on cultural values and philosophies that transcend mere financial gain. We discuss the difference between living good and well, the power of forgiveness, and compounding more than just your capital.

• 3:09Patrick O'Shaughnessy?

  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.

• 3:23Patrick O'Shaughnessy?

  So just before 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. 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. 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. This first one comes from Carlos, but I love it.

• 4:06Speaker 02

  You cheated.

• 4:07Patrick O'Shaughnessy?

  So I'm using it and I cheated.

• 4:08Speaker 02

  I like it.

• 4:09Patrick O'Shaughnessy?

  Carlos's question and mine is, what is the big dream?

• 4:14Speaker 02

  My big dream is to live in a state of well-being most of the time and to have a sense of lifelong satisfaction when the end comes.

• 4:26Speaker 02

  So it's really very internal versus something that gets accomplished or left behind.

• 4:33Patrick O'Shaughnessy?

  We're going to pick that apart in detail, but go down one level.

• 4:36Speaker 02

  Sure.

• 4:37Patrick O'Shaughnessy?

  What is the Red Ventures' big dream?

• 4:40Speaker 02

  We've been on this journey for 24 years. Then in one sense, it feels like we're about to go on another 10-year journey of reinventing ourselves. Red 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 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.

• 5:10Patrick O'Shaughnessy?

  Can you 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.

• 5:20Speaker 02

  On purpose.

• 5:21Patrick O'Shaughnessy?

  I know on purpose, but I have to ask. Maybe the best way to ask is, how did it begin?

• 5:26Speaker 02

  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 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 a vis these companies being separate. And today, we, depends on how you want to count, have about 15 different companies inside of the portfolio, all over the place, between Europe, Brazil, Puerto Rico, and then our core business is here, inclusive of a big joint venture with United Healthcare and so forth.

• 6:12Patrick O'Shaughnessy?

  So if we go back to the very beginning, something worked. You and your team were awesome investors or trend spotters 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?

• 6:30Speaker 02

  Luck. I think we're more lucky than sprinkled luck. I've always believed that. And if I look back in our journey, Dan and I started this company in January 2000. Dan and I worked together before this at a company called Sendin CUC. And we really started with two principles in mind. One was, let's build a company we would 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 would wanna work at a place or build a place that we would wanna go work every day. So we never have to work. True definition of being an entrepreneur. And then the second one, and I think we said it at the time without really understanding it,

• 7:14Speaker 02

  which was a company that would outlast us. And even though we would wanna do this for a long time, Dan retired about a year ago. A company that would outlive us. What I have come to realize is it will outlive us through the people that get trained 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 $2 million from our friends. This is the frenzy of January 2000. This is before the first internet bubble implosion. Raised 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.

• 7:59Speaker 02

  And by November, we had $117,000 left, no revenue. And this crazy thought of like, I will never attend my reunions. Because all the capital came out of my business school friends. And I'm a proud guy. I'm like, I can't. So we literally just hunkered down, hustled, sold marketing programs, 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 2004, we had enough money to pay our investors back. And we said, look, and we made a commitment to you. Here's your money back times 10%, but we're done. If you keep your money in here, it's at your own risk.

• 8:44Speaker 02

  And I hopefully hope you take the money back. Because that burden of taking someone's money was a lot. And in 04, 05 was when Google was becoming 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 going to need somebody to kind of help them defend themselves in this environment that's aggregating intent and customer acquisition is a 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. 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

• 9:29Speaker 02

  by how you navigate it online. So we could go to any brand and say, we can out convert whatever you're doing in this notion of take your agency, take your call center, take your internal operations, we can out convert it by 30%. 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. And that became kind of the first unlock in call it 2006 to 2010. And from there, there's a cemetery full of skeletons of bad ideas and we went our way through it and long behold, come from 2010 to now and this is where we are.

• 10:07Patrick O'Shaughnessy?

  What was the first thing you ever bought? What business was the first business you ever just bought outright?

• 10:12Speaker 02

  First meaningful thing we bought where we literally broke the bank, we had a pristine balance sheet was Bankrate. Bankrate at the time was 1.4 billion dollars and it wasn't worth that. Before we bought Bankrate, we bought in asset in financial services that it was a tiny asset where we said, let's go improve that we can actually use that asset in Google and paid search and SEO and really start doing what we did in telecommunications, 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. And Bankrate was our first big acquisition at the time. We had on credit cards.com, the point sky, Bankrate and a bunch of other miscellaneous assets. And it was our first,

• 10:56Speaker 02

  okay, we're in the big leagues now and we have a lot of debt.

• 11:00Patrick O'Shaughnessy?

  There's quite a lot of glossing over going from $2 million paying back your investors to a billion and a half. Dollar acquisition.

• 11:06Speaker 02

  This is a decade.

• 11:07Patrick O'Shaughnessy?

  That I'd love to dig into some degree. What would you credit your early operating success with? Obviously, you got to that scale on an unusual way with not a lot of outside backing and control of your own destiny and permanent capital and all these things. 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.

• 11:32Speaker 02

  Survival to some extent. When you spend the first four years, two little kids, both of us not taking any money home. Humility, understanding that this could change easily. Early on, we would meet with our 80 employees, call it 2007 and eight. And we were now making millions of dollars of profit. And I will say, oh, I enjoy this. These are the good old days. Someday this will end. It was this constant belief that this was a moment in time. And if didn't 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. I never thought that our competition was somebody else. And we've really never competed.

• 12:17Speaker 02

  And maybe it's because of our near death experience as a business so early against the fear of something. We always thought, look, if we can compound our performance a little bit every month and our business model gave us the fruits of that. It was all performance based deals. We got addicted to this notion of incremental performance just becomes really virtuous for us. And that was our thing. Your strengths become a bit of your vulnerability. I think to this day, our DNA, thousands of people strong is incredible operators, really good optimizers, maybe not as great people doing high end product or experimentation and other things. Now we've brought in a lot of people to help do that and all of that.

• 13:03Speaker 02

  That is probably our core DNA of our adventures.

• 13:07Patrick O'Shaughnessy?

  I'm going to zoom back and forth a lot here.

• 13:08Speaker 02

  Sure, sure.

• 13:08Patrick O'Shaughnessy?

  Go all the way 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 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. You said there's more than a dozen companies in all sorts of places, but 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? How did that come to be? Because I think those are hard to establish.

• 13:48Speaker 02

  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, 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 2010. A decade of bootstrapped. When we raised 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. Meaning we have wonderful investors.

• 14:32Speaker 02

  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 going to go public or we're going to try to sell the business. For good and for bad, it's just giving us license to invest in things that others wouldn't. And back to the principle of a place we would want to work for. We decided that our culture was really going to become that string of DNA that will permeate around the whole company. And when you walk into our building, you'll see a series of belief statements written 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.

• 15:17Speaker 02

  And if those things resonate with you. 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 will evolve and will continue to evolve because the core belief is everything is written in pencil, which in itself is a bit disorienting at times. 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 24 innings of an incredibly interesting game. Not every inning has been perfect and that's part of what makes it beautiful.

• 15:51Patrick O'Shaughnessy?

  Which of those four beliefs, not counting that core one, is most on your mind these days?

• 15:57Speaker 02

  There's seven beliefs right now. We've added some, making every second count really matters because I think the world right now, those starting in a perch, which I think we are having advantage, but those are going to 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. 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 it in a lot of capacities. And I worry about, do we have that fight? Do we have that thirst?

• 16:40Speaker 02

  Do we have that fear of not being relevant in 10 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 going to 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 our leadership standpoint.

• 17:01Patrick O'Shaughnessy?

  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?

• 17:15Speaker 02

  There's no magic bullet. I think you've got to find people that.

• 17:18Patrick O'Shaughnessy?

  Want it.

• 17:19Speaker 02

  Want it. And then I think typically athletes or people that are musicians, people that have been coached heavily in their lives tend up doing well in environments like this because coaching is not criticism. It's like you're making me better. People that 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 skillset. You need people that really are in that mindset and mode.

• 17:46Patrick O'Shaughnessy?

  If I were to be annoyingly reductive about the Red Ventures stories, would it come down to you were just earlier and better at understanding how marketing was changing in the internet era than others?

• 18:02Speaker 02

  That would not be accurate and that would overinflate really what we did. We did not know we were earlier. Actually, I would argue that we were a little late. 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 work collectively better than most and we're hyper-competitive against ourselves. In our 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, 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,

• 18:46Speaker 02

  super talented kids that want to stay in this region and want to be in a place where they get trained, they get invested in, they are pushed on. They love coming here. We have insane talent coming here.

• 18:56Patrick O'Shaughnessy?

  My sense is, and I'd love to just like pick any example you want, that frequently you would buy a new company and the performance of that company would go up a lot after you owned it.

• 19:08Speaker 02

  Correct.

• 19:09Patrick O'Shaughnessy?

  Can you pick one story and in some detail describe what it was when you got it and what you did and how it changed?

• 19:17Speaker 02

  You think about the core of what Red Ventures was, and it still is to some extent. It's a B2B platform on basically doing customer acquisition, performance, marketing, growth. Like at the end of the day, when I sit down with a CEO, I say, 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, 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 either a new CEO or a crisis

• 20:02Speaker 02

  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 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 basketball player batting average. Taking a company and if we bought it at 10 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's just one of those, but we can take any funnel

• 20:47Speaker 02

  where there's heavy data, heavy experiences and use our technology to basically yield a lot more out of the same flows. That has happened time and time again in every asset we bought.

• 20:57Patrick O'Shaughnessy?

  This was the 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 it 10 and pretty quickly you effectively paid for. So why aren't there 10 Red Ventures? Like, why aren't there 10 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. I've looked.

• 21:34Speaker 02

  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. And 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 shop in an industry or two. Some of them better than us at certain things. Some of them go the brand, okay, I'm going to build my own consumer brand versus building a much better middleware. And others, I'm going to do it really deep here and then I'm going to sell it to somebody. So I think a little bit of this is incentive structures.

• 22:10Patrick O'Shaughnessy?

  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?

• 22:23Speaker 02

  Compounding of a lot of things. A lot of three percents on each other quickly are 20%. But here's what's really interesting, Patrick. That you could argue is maybe 50% of our business. The business that we're super excited about in the UK, we own a true software business that powers 80% of all the real estate agents. We own a data business that nine out of 10 banks 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 marketing. So we took this B2B business, ended up saying, wow, we can do this and buy assets to do this ourselves.

• 23:06Speaker 02

  And the value is now we get all that richness of data 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 head, we're like, 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.

• 23:25Patrick O'Shaughnessy?

  When you see a new company or a new team or something, what gets you excited? Like, what is your taste?

• 23:33Speaker 02

  To buy?

• 23:34Patrick O'Shaughnessy?

  Yeah.

• 23:35Speaker 02

  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 going to unlock something and are going to motivate 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. 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 going to really sell you something and not really be committed to whatever the transition period is, multiple years or whatever else, that's really, really important. Understand the motivation of the seller. And what we've done really well is when we've engaged with somebody that we really understand the why.

• 24:20Speaker 02

  The second thing is I like places where you can win in multiple ways. So when you make a single bet, it's like, okay, I'm betting this happens and we have to compound growth at 20%, but if we don't compound growth at 20%, 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. 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 or other value that brings. And because of our cultural alignment, you can get that out. A lot of companies can't 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.

• 25:05Patrick O'Shaughnessy?

  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?

• 25:19Speaker 02

  If I don't really think the person is generally a good human being, doesn't have to be like me or whatever, I'm turned up because that will reflect on the things that I won't be able to see. 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, 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.

• 26:04Patrick O'Shaughnessy?

  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 18 years between us. I'd love to kind of go category by category 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.

• 26:28Speaker 02

  Money is a tricky thing because money corrupts 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 miss 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 your kids. It affects what you're going to 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.

• 27:13Speaker 02

  Or 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 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. One of the things back to this point of thirty-nine and fifty-seven, I was big into time and I have all these principles around time and how do I think about compounding time and all these things that are kind of 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.

• 27:57Speaker 02

  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 drained my energy, it's like, you know what? I'm not doing that again. Or wow, I love my energy with this person in this situation, then you lean into that energy, right? So I'm very thoughtful of today. It's like I just want good energy in my life.

• 28:19Patrick O'Shaughnessy?

  As someone that just tweaked my lower back, likely due to my rising age, how have your views on your body changed?

• 28:26Speaker 02

  I think the body, it's like heart. Heart disease starts in your twenties, it doesn't show up into your fifties. And hard 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 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. I want to 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.

• 29:10Speaker 02

  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, 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 in balance and all those things. Can you draw the contrast between good and well? That's my favorite new thought. I think in life, things are good, like people are, 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 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 in what I realized.

• 29:54Speaker 02

  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. 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. If you think about well-being, it's really two different words. Because they're connected when we say them, that 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 couple those two words, well, is actually that feeling that you get of peacefulness inside,

• 30:34Speaker 02

  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, that 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. 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 at myself. And then being is the one that I find so interesting. We were talking about goals and no goals and the value of goals. And think about another one. It's like we spend all our time doing things. We have to do list. Everything is a do.

• 31:18Speaker 02

  Society rewards us for accomplishing things, for 450 podcasts, for this and that. That's doing. And what you realize 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. You're doing it because you feel connected to whatever it is. And it's really hard when you spend 110% of your time doing to find the muscle and find the space to start being. And well being is a place where you feel really settled inside and you spend the time you want just feeling connected to whatever you want to be connected to.

• 31:58Speaker 02

  And you suspend all this societal bullshit that we give so much power to, that manipulates the way that we think the world wants us to show up. 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 10, 20 years is die peacefully will be understanding that I became super clear on how to live life the way that I think my soul was intended to live.

• 32:24Patrick O'Shaughnessy?

  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 are thinking about this?

• 32:34Speaker 02

  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. 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. A little bit of this, you gotta decide what it is, but it can't become you. You can't put that inside of you. And I think we're all in some struggle and some journey to find our connection to ourselves. And crisis usually reveals that.

• 33:16Speaker 02

  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.

• 33:29Patrick O'Shaughnessy?

  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?

• 33:39Speaker 02

  The experience, I think, was three and a half minutes. So I think you're like little.

• 33:44Patrick O'Shaughnessy?

  The whole thing.

• 33:46Speaker 02

  Look, it's the greatest gift one can get. It's the greatest gift to know that you're gonna die.

• 33:52Patrick O'Shaughnessy?

  Were you certain of that?

• 33:53Speaker 02

  A hundred percent certain. It was either I'm gonna blow up and that will be a lot better than breaking into pieces in January 15th in the Hudson River in New York and freezing in 40 seconds. If you were given those two options, I think blowing up is better. And then you have 90 seconds to say goodbye to your life with no suffering, zero suffering. 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 an incredible crisis. We were coming out of the financial crisis of, wait, this country was in a low place looking for a story. So we were really lucky that we had the most incredible pilot on that seat that day that

• 34:36Speaker 02

  in many ways, and we can talk about him, he'd been preparing for that moment his whole life. He was a gliding instructor. Later on, I got to know him really well and he would say that you're only a pilot when you lose an engine. Otherwise, you're just managing the autopilot or whatever the inputs in the computer. In that day, it was a New York cold 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. Bam. Half asleep as you're taken up, you realize, I look at the flight attendant and I'm in 1D so I can see the flight attendant. There's nothing in their face, just like annoyance. It's like this is gonna be whatever, because we turned the plane right away and

• 35:19Speaker 02

  nothing is happening. 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 identifies himself and he says, three words, the only three words he said, and this was the moment. He says, praise 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 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 90 seconds to literally say, it's over.

• 36:04Speaker 02

  I am sitting there going like, oh my goodness, it's over. Not only is it over, and then some people you may have a near death experience of a second or two seconds. This is a minute and a half to basically sign off from life. 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 in life. And lots of things happened from how have I dealt with spiritual 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 gave myself because people talk about it.

• 36:45Speaker 02

  And it's a reminder of me of a promise I made to myself that day, which is I was not gonna let that experience. Someday, I wanted to be a part of me, not something that happened to me. I've tried to live very hard, very consciously of the gift I got that day.

• 37:00Patrick O'Shaughnessy?

  Can you remember sequentially what went through your head in those 90 seconds?

• 37:04Speaker 02

  Yeah, when I think about it, and I think about it now more evolved with time behind is a lot of it had to do with the immediate emotion that I felt was this, oh no, it's over. 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 I think in our evolution, we're unable to process that because we would have never left the cave if we felt that, right? So there's this concept called hedonic adaptation that we will adapt to whatever situation. And that's what life is about. We have adopted this thing.

• 37:48Speaker 02

  And that was for me, this notion of, gosh, when the plane landed, I am gonna live 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 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, because I know it's gonna change in an instant. Tomorrow, maybe that instant. And I'm not having that regret if it happens. The second thing that I thought about it was like, you go into superhuman, right? Your adrenaline is shooting. You're in survival mode. You're gonna die.

• 38:33Speaker 02

  It was this sense of almost embarrassment of how much I had allowed my ego to be who showed up in the world, how much I had spent energy being wronged 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. And it was this notion that, you know what? I hate it. I hated what that meant and that I didn't realize that that was a mask that I was putting on and that I didn't need to have that mask on. That ego started with, 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.

• 39:17Speaker 02

  And I don't share this a lot. I don't know how people take it, but I ask myself. Okay, do I buy insurance? I can ask for forgiveness. I was raised Catholic. I can ask for insurance right now. 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. And I said to myself, 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 didn't feel natural to me. And what happened as a result to me after that, after just 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.

• 39:58Speaker 02

  It's like I no longer had this notion, and I think guilt drives 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, 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. 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, but you then find forgiveness in everything.

• 40:43Speaker 02

  I am super, super forgiving. And to me, true forgiveness, and there's many definitions, is when you forgive when the other person doesn't apologize. Because the forgiveness comes from love 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 as 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 going to hit the water, and you're like, okay, please blow up kind of thing. I really had this thought is, wow, I was not scared. And I thought it would be super scary. And I was certain. And the feeling was actually sadness.

• 41:23Speaker 02

  The feeling was somehow I had missed my opportunity to leave my mark in this world. I had not focused on whatever my purpose was meant to be. I was so busy accumulating, doing the things that society asked me to do, that I have forgotten that I actually 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 life. And that manifested itself on like my kids. I really justify myself being a light. Five percent of the parenting, my wife carried the load and she did an incredible job. But I felt like, oh, I'm doing this side of the equation and she does that side of the question.

• 42:08Speaker 02

  And I was like, I've changed dramatically. My relationship with my kids right now is fantastic. Because I realized that that to me is my purpose. But my purpose is also this business. I am here 24 years later and as engaged as I am because I believe that this place is a place of good. It's a place of good where you come here, 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, because it's more random than not, is an opportunity to actually put it back into the system in ways. I'm reconnecting with Puerto Rico in the most beautiful ways. And what a privilege.

• 42:52Speaker 02

  It's my purpose to put it all back in. So for me, life has become really, really simple. That was kind of my last 10 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 feel meaningful.

• 43:11Patrick O'Shaughnessy?

  You've teed me up. Please tell the entire story of turning this basketball team in Puerto Rico around.

• 43:18Speaker 02

  Oh, that's a nutty story. Really? We're gonna go there. Little bit of context.

• 43:23Speaker 02

  Hurricane Maria was, I think it's seven years, coming up now, six or seven years. After Hurricane Maria, if you're Puerto Rican, you really love your island. And I found this really interesting. A lot of people ask me, oh, you Puerto Rican and you're American. I'm like, I am both. I'm not a percentage. I'm 100% both and I'm really happy to be both 100%. I get two things out of this. Um, 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 in four by fours and we got into the mounts and we were delivering baby formula and medicines and all these things and feeling really good about ourselves. Our egos were super healthy that we were saving nothing.

• 44:08Speaker 02

  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. So I came back and organized our comms team and they always get scared because I have an idea. It's code for like, oh no. And because a lot of them are bad ones, but as 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 and fast forward a journey. And we have five companies in Puerto Rico with hundreds of employees disrupting banking, disrupting media.

• 44:51Speaker 02

  Really a phenomenal and it's a movement. It's not even a company. All the CEOs, a little bit of a different org 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 because it was too small, that little island. 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 or conviction

• 45:33Speaker 02

  to go do something bigger. And it's this beautiful movement called Forward 787 that we just are all a part of and it's authorless and all of that. Well, as part of that, now that's preamble to this thing. I love all that. All my high school buddies and we all, we still get together and we're that age again and we all love hoops and the inside story is.

• 45:53Speaker 03

  I always loved hoops more than it loved me. I was pigeon toe, I'm super tall. I really almost never made any good team. I was always in the B team. I sometimes made the C team. I 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 recognized effort to growth and reward. And I got better and better and better. And I literally was the last cut of a semi pro team my senior year in high school. And the assistant coach was my high school coach. So maybe that's why I was the last cut and not the first cut. But I was there and I belonged and then I was getting paid like a hundred bucks a week. I was a professional and I loved it.

• 46:34Speaker 03

  And by the way, it was the best thing that happened to me because then I went and studied and that's when I left for the US. But I've always loved the game and I love it here, sitting next to the Hornets bench. I got good friends with like five coaches in the NBA that I talk to all the time. I know, oh, I know everybody, but 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. And so my buddies are like, man, the league in Puerto Rico is 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. They're like, come on, we'll do all the work and we will go drinking. And they're like, all right, cool.

• 47:14Speaker 03

  Look, if there's a team we can buy and like Bad Bunny owns a team, Rosuna owns a team and Yadi Molina owns a team. And it's like, it's really bad. It's really good basketball, but super competitive. And I'm like, like teasing, then all of a sudden like 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 could play at a little volleyball court for three years while they build us a court. And it's the worst team has never made the playoffs. This is 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 joy. Fast forward tomorrow. So that team has never made the playoffs.

• 47:58Speaker 03

  There were three polls at the beginning of the season. We were ranked 12, 11 and 12. There's 12 teams. We were the easy game in everybody's schedule. Fast forward, we are playing game seven of the finals tomorrow night.

• 48:15Speaker 02

  And it's been the craziest, most fun ride. And you know what I realized, Patrick? I had never owned a toy as an adult. A toy where you literally do it for the pleasure of it. And the connections, the ability to bring 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 this in the middle of the season, not winning the finals. Say, this is my favorite team I've ever been a part of. And it's all culture. At the end of the day, Patrick, we all want to belong to places that we feel connected to. And the magic of organizations is understanding that.

• 48:57Speaker 02

  And in this world, we are so disconnected from so many things. People no longer belong to civic groups or churches or all of this. And the ability to create connections, like this town is going crazy. Win or lose, it didn't lose, it doesn't matter. It's like, I so good. Like, if you go through the year, go back to your calendar and say, what are the things that I'm going to remember 10 years from now? You'll be shocked how few they are. If you're lucky, you have six, seven, 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?

• 49:35Patrick O'Shaughnessy?

  Yeah.

• 49:35Speaker 02

  I need to design that into my calendar. I tell you, I have like three of them that are going to show up at the end of the year, including two nights ago, when we're down 10 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 yesterday, which I am completely exhausted for, and it was the greatest thing ever. So it's been awesome.

• 49:58Patrick O'Shaughnessy?

  So tell me what you did. How did the culture change? What is the culture of the team? Like, I went and asked everybody, and don't sure change yourself. Like, someone told me that you called and were talking in the locker room to every player one on one. You are involved. This is not something that you're just phoning in.

• 50:14Speaker 02

  I've been in Puerto Rico nine times and it's like I literally go all down for two games and run back. So I just get so much joy out of it. It's just uncomfortable to talk about, but okay, now I'll give you a little. The first practice we show up, all these players are looking at like, okay, new owner. Players don't trust owners. They get treated like merchandise. They get lied to. They get all this stuff. 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 others. 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. We put in a full weight room. We put in a bunch of staff. They're

• 50:56Speaker 02

  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 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 there's nobody that is above the team. So this is a team first and all of that. And we've entrapalated 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. Culture is what you tolerate. It's not what you preach. Our best player, we suspended 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

• 51:41Speaker 02

  been part of a team. These kids get treated like whatever. So great teams, great teams in anything in life, it is team first. Because most places are player first. Exceptional teams that where they exceed their expectations where we are, we are like the eighth best team, not the second or first best team, is when there's teammates first. These guys, the love that they feel for each other is beautiful. And the great thing about teams, back to community, is like, once you are part of an experience like that, the team will end, 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

• 52:21Speaker 02

  never make it again, it does not matter. No one, there's a saying in Spanish, nadie me quita lo bailao que quieres. You can never take away the songs I've danced. We go to the games, all my friends are sitting in the friend row, like, it is literally a reunion of high school there. And it's just beautiful. It's just beautiful. The 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.

• 52:48Patrick O'Shaughnessy?

  How could I watch this game?

• 52:49Speaker 02

  It's on YouTube, actually.

• 52:51Patrick O'Shaughnessy?

  Okay.

• 52:52Speaker 02

  Eight o'clock. It is. There were like fifty thousand people on YouTube in the US watching the last one.

• 52:56Patrick O'Shaughnessy?

  Incredible. Oh, man, I hope you win. But it doesn't matter, like you said.

• 53:00Speaker 02

  It doesn't matter. It's a game. There's no winning. We won already.

• 53:03Patrick O'Shaughnessy?

  It lets me jump back to our list. Thirty-nine to fifty-seven on leadership. And I was thinking about this as you were talking about Sully. And how to characterize him. 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. But rather than asking 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.

• 53:35Speaker 02

  It changes a lot. 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 may be experience. 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. 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 good leaders are not liked, they're respected. And they're respected for being consistent, being clear, being fair, giving, being all the things that matter, kind and all these different things.

• 54:20Speaker 02

  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. If you don't really understand yourself. And then it's an imperfect art and you're constantly growing and learning. And we had a staff meeting yesterday in the morning, you know, I think it was fantastic. And in the afternoon, I didn't show up that great. And I was exhausted from that silly game. And I was short-fueled. I was like, I got in the car, like, ah, that wasn't my best performance. And then I laughed and then I'll own it and move on. Leadership a lot of is how you show what it is to be human. A lot of leaders feel like they have to pretend to be perfect. And look, we all have insecurities. We all have challenges.

• 55:05Speaker 02

  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.

• 55:14Patrick O'Shaughnessy?

  This is a very strange question to ask an extremely successful business person. Do you like business?

• 55:20Speaker 02

  I love the game of influencing. 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 evidence. So the business of making money, fine. It's a score that is kind of silly. The business of bringing people together to a common goal or to a purpose, 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 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, so I wasn't gonna be a great athlete.

• 56:05Speaker 02

  My brother's super handsome. I shut 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 business? My default answer would have been, of course, because I sold avocados on the street like when I was 11. But what I really liked was being independent. I'm not really sure that business was what I wanted.

• 56:36Patrick O'Shaughnessy?

  Yeah. What was the key to selling avocados?

• 56:39Speaker 02

  Getting them really cheap at the farm and then, you know.

• 56:41Patrick O'Shaughnessy?

  Low cost provider.

• 56:46Patrick O'Shaughnessy?

  You described earlier for fun, going through our decades and trying to label the decades a little bit with like a word or two. You said for your 30s that courage was the word.

• 56:56Speaker 02

  Yeah.

• 56:56Patrick O'Shaughnessy?

  That was an interesting word and that for your twenties, it was confidence. Can you describe why courage? That's so interesting.

• 57:02Speaker 02

  I actually want to answer confidence because confidence goes into courage. I think you need that confidence. So look, I'm 20, 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. 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 OB-GYN, 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 struggled, I was lonely. I figure out a way to take a six-month assignment, stayed two years, I was General Electric at the time.

• 57:48Speaker 02

  And all of a sudden, 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 applied, I get a letter, it's like, do you remember a class of ninety-four? I'm like, holy cow, they let me in. So I'm like, whatever, twenty-six, and I get to Harvard thinking I'm definitely not gonna make it. 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 finished business school and everybody was gonna McKinsey or Investment Banking. I'm like, you know what? I've always kind of listened to a different radio station than most.

• 58:32Speaker 02

  And I always knew I wanted to run a business, start a business. I wanted to be independent. I have a story of 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 the change of decades, that's when, like, literally, I got married. And basically, we started the business. So the twenties was the place where I was 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 I go to these meetings and I kind of laugh. I'm like, how in the world did I end up in this room? I'm sure sometimes that happens to you, right, Joe? I start singing my Hitwana, it's not like the others. It's just everybody's the same.

• 59:16Speaker 02

  No one above, no one below. So the thirties, a little bit of this is. We struggle, we struggle in there. Losing all these pregnancies was really, really hard on our marriage. And we were this close to quitting and going down the path of building our family in a different way. Took 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 and necessity is actually a really driving factor.

• 59:57Speaker 02

  So 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. I build a lot of courage. I'm like, you know what? I'll go for anything with a little luck and the right people around you, anything can happen. Can you tell me about your grandfather? I never met my grandpa. He's my dad's dad. By all accounts, he was much older than my grandma. He's 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 growing up, part of Puerto Rico, back in Lebanon, Christian Lebanese. And then he came back in his twenties to Puerto Rico and became one of the most successful people. The stories of my grandpa was like twenty servants in the house, one of the big mansions.

• 1:00:41Speaker 02

  And he was basically had cornered the market for all vegetables, imported everything, set the price. Stories of predatory pricing, beautiful, like this crazy stories of all the things he was. Like, I mean, and I never met him. There's a lot of this 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. And I imagine he's like, look, that money belongs to me, not to the government. So they took everything away. So my dad in his teens 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 would have these family dinners and big Hispanic Lebanese families.

• 1:01:25Speaker 02

  There's thirty people at the table, right? You're the little kid and inevitably. 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. 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 wanted them to feel proud of our family.

• 1:02:06Speaker 02

  I wanted to do what my grandpa did, but do it in a way that was ethical. And my family could be proud of my grandpa through the work that I was doing. And I only realized 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 it picked this. It's like, this is a random roulette. It's just, it's the gene pool of, I got my grandpa's gene of being a merchant.

• 1:02:31Patrick O'Shaughnessy?

  Fast forward a number of years and you and I were on a walk and you said something to me, 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.

• 1:02:45Speaker 02

  Yeah.

• 1:02:46Patrick O'Shaughnessy?

  Maybe say a bit more about that idea. Hit me kind of hard.

• 1:02:51Speaker 02

  Society sets us up on a trick. All of this is a mirage. Every time you get to a peak, you'll see higher peaks. There's nothing about a peak that matters. Sometimes it's over said about the journey and this and then the other. It's that inner peace, that sense of well being that really matters. How many days of your life do you have a sense of calm and peacefulness and purpose? And you're in a good place. You feel like your energy is in a good place. To me, that's what really matters. And 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 for you. But when they're replacing happy with happier, that's when they get in trouble.

• 1:03:37Speaker 02

  There's no such thing. I have a fun exchange. An employee came in and I was like, hey, you're back. Great. We have a bunch of boomerangs. It's silly how many boomerangs we have. And I'm like, you're back. And I jokingly said, hey, the grass wasn't greener. He goes, no, I like this brown. And it's true. Everything is a little brown. I've stopped pursuing more. That's why anything I do from here and out with my capital, the return on the capital, I don't invest anymore on funds. I don't invest in anything. I don't want to compound capital. I know that sounds like

• 1:04:08Patrick O'Shaughnessy?

  Sacrifices.

• 1:04:10Speaker 02

  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. 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. Capital for capital, what? You're never going to beat Bezos or whoever else. Like, that's a silly game.

• 1:04:37Patrick O'Shaughnessy?

  You flipped something around on me earlier today that was really interesting around this idea of like, ninety, ten in a conversation 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. Like to think I'm that way. But you had a different perspective on this. Can you explain that?

• 1:05:06Speaker 02

  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 listen to them. You can ingratiate yourself shortly to somebody who says, oh, how good. It was wonderful. It's because you talk a lot about yourself. That said, one of the beauties of true friendships is allowing the other party to feel that they can love you back. And I told you the story of a dear friend of mine, one of my best, best friends. It's like my first best friend in the U. S. 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 because someone who worked in those study. And one day, many years later, I have dinner with him in Boston and his wife is also a great friend of mine.

• 1:05:51Speaker 02

  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 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, oh, yeah, yeah, 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. And he said, you are the most selfish friend I have. I was like, you just talk for 90% of the time. I just, I bought dinner. I like, what else can I do, right? And he goes, you don't ever let anybody else love you back.

• 1:06:31Speaker 02

  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 able to be a receiver. And it was holy cow. At the time, I'm like, wow, this guy went lonely. 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 time. That's selfish, letting people in your true friends. I now share my struggles the last two years. I literally thought that would, I would, because 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 a language I'm like, I'm very open with people that I trust because it's what friendships are about.

• 1:07:16Speaker 02

  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 them a chance to love you back.

• 1:07:26Patrick O'Shaughnessy?

  How do you recruit people here? Like just shaking hands and talking to some people a couple of hours ago. You get this incredible sense of. Excitement to be here, front-footedness. So what are you looking for in the people that you bring to Red Ventures?

• 1:07:43Speaker 02

  I think part of that is who you bring here. So I think you're making sure that 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 going to 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 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,

• 1:08:28Speaker 02

  you go to the third coffee shop in a week and 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. So in here, ultimately people behave in a way. So when you walk in, they're like, oh, this is the norm somehow you behave here. And all of a sudden becomes like, ah, this is how I fit in. 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.

• 1:09:01Patrick O'Shaughnessy?

  If you think about the investing side of your brain or world, I kind of 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 20th of the price you sell them. 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 in 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?

• 1:09:29Speaker 02

  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 can you win multiple ways also applies on the other side. When I look at a business model, if the business has three variables for it to work, I will never invest in it. There's some great businesses that need three variables. They're going to need a ton of capital, a ton of luck. They're going to have to figure some stuff out. If the business has two variables, then you're compounding the risk. So you better be fairly certain that one of those variables 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.

• 1:10:12Speaker 02

  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 that you would apply to an intuitive decision. And when we see something, we're like, okay, that's worth the bet. But understanding that when you're betting, you're going to lose some. And if you're, I think if anything, you need to have bad bets to be able to be a good better. Otherwise you're just taking fastballs 85 miles an hour down the plate.

• 1:10:41Patrick O'Shaughnessy?

  What episode of Red Ventures history do you look back on with the most pride?

• 1:10:47Speaker 02

  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, these are not the same days that it used to be. And of course they're not. Everything Danny Meyer, 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 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.

• 1:11:28Speaker 02

  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, it was like lightning in a bottle at a moment in time. And it was a moment in time. You felt that today, this is a magical place. There's a magical culture here, but comparatively, so probably when we're compounding at thirty percent for like five years in a row and we're just success after success. It was like, wow, we're really good. Reality is we were really lucky. We were really good. And it was a matter of when that we needed to do it. I'm kind of very excited for the next five years. I spent a lot of time listening to your digestion of AI, but I think AI is really

• 1:12:10Speaker 02

  going to change a lot of our businesses, some of the traditional ones, but even our partner business, our client business is going to 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.

• 1:12:26Patrick O'Shaughnessy?

  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 Ken, if you want, talk about what in that world 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.

• 1:12:48Speaker 02

  We owned a bunch of really interesting assets. We own a bunch of assets that created a lot of both data and consumers path, but you realize that those are kind of narrow businesses that exists for a period of time. We did this JV with United Healthcare, who their CEO, Andrew Witty, is a fantastic CEO, is a fantastic human being. And his view is that the healthcare company of someday of the future five, 10 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 got to get really good in the consumer side. And he is like,

• 1:13:30Speaker 02

  there's no way a company this big will ever figure that out. So I got to 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 and it's been great. First year was typical, put two organisms together and our joke was like, look, we don't want our size and your speed. That will be a disaster. We're doing this so that 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 of years should play out, but we're preparing for a future world. Healthcare is counterintuitive. The money in healthcare in very specific pockets, if you really think about it, there's not

• 1:14:14Speaker 02

  a lot of value that has been sustained because where the money is given the governments putting the thumb on their scale with Medicare and all this different stuff is just really tricky. And I think doing it as part of the best and biggest healthcare provider and platform out there and United Healthcare was the best way to do it.

• 1:14:31Patrick O'Shaughnessy?

  And so what is the North Star for the product in that business? What is the thing you're trying to deliver?

• 1:14:36Speaker 02

  Ultimately, you want a place where the consumer gets all the answers, all the connectivity, 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. This is not going to be able to live outside. And this is the largest platform to do it inside of.

• 1:15:07Patrick O'Shaughnessy?

  You mentioned speed. One of the very popular ideas in the West Coast and startup land is you could beat anybody if you're fast enough. What do you think is the role of speed in business?

• 1:15:22Speaker 02

  We used to call speed and then we ended up tripping ourselves because we were like, speed trumps 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. It's an iteration of that. One is pace. Because pace is sustained speed. You see this marathon runners who go out and win the first mile and never finish a race. So you got to understand pace and how do you bring in organization? And the other one is not sprints. It's you're almost running intervals inside of a race. So when you combine pace and intervals, we got a big push for the next 60 days. There we got different things. I think that's the sustainable piece, speed part of this. I'm not sure that's right, but that's how we think about it.

• 1:16:06Speaker 02

  Because otherwise you end up either in a body shop or people get burned out or to what end? And again, it has to be managed and purposeful. I do think that reps really matter. And the ability to do this faster is how you can build better models. It's how you can build better product. It's how you can get to differentiation. And when we go to big companies and our business model, the core is a B two B business. What we say to them, look, we have a platform that allows you to grow faster than you're growing. And we're willing to get paid only if 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 grade, security, industrial grade, everything. We may be able to help you.

• 1:16:51Speaker 02

  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.

• 1:16:57Patrick O'Shaughnessy?

  Are there other, any other philosophies that we haven't talked about? That you feel like govern a lot of your own behavior?

• 1:17:06Speaker 02

  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 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 Simone Perez used to say, press and awards are like perfume. 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. I joked with you, I'm like Forrest Gump running a business. Like I'm not sure what it is and who cares?

• 1:17:46Speaker 02

  And I work really hard and I care really deeply, but we just put weight on things that don't matter.

• 1:17:52Patrick O'Shaughnessy?

  If a high integrity builder were to come study.

• 1:17:57Patrick O'Shaughnessy?

  This place for a year, really have access with the intent of I'm going to go spend a year studying RV and I'm going to leave and I'm going to start a platform. What do you most wish that hypothetical person would take with them?

• 1:18:13Speaker 02

  At the core of what I hope we leave as our legacy is thousands of people 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 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 20 and 30 when you leave college, which I think it's at risk right now with all this not coming to the office and everything else.

• 1:18:55Speaker 02

  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 going to be bigger or more profitable because that ability to train people is what allows for innovation to happen and changes to happen.

• 1:19:12Patrick O'Shaughnessy?

  How do you do that? Like, teach me how to do that. Like, if someone has the desire, you've 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 is this? Is it systems of accountability? Is it ways of thinking about the customers? What is it that you're investing and doing to imbue that in people here, like in a brass tacks way?

• 1:19:38Speaker 02

  It is 50 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. It's like all the instruments, recruiting, performance reviews, career tracking, training.

• 1:19:58Speaker 02

  Management, 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, 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. And 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 that way. If you're twenty-four and you don't know too much, I feel like we're robbing you from

• 1:20:41Speaker 02

  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. 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, and I think it's happening everywhere. Our apprenticeship layer in the US is not just companies, it's hospitals. Take anything, any practice. Super interesting.

• 1:21:11Patrick O'Shaughnessy?

  Do you feel like the architect of all those things, those fifty things? Like, is that something you wake up on a Saturday?

• 1:21:15Speaker 02

  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. 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. 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 said we have to do this. And then we wake up six months later, what are we doing? There's like, oh, you said it.

• 1:22:00Speaker 02

  I'm like, that's a horrible idea. I can't tell you the amount of times that an extrovert like me that thinks out loud is like, holy cow, it's like you have now like- Everything is disclaimed, just like you disclaimed this is not personal advice for investment. And we have tremendous talent. I gotta look, the woman that runs comms here is just world class. A lot of the team that sits in our people capital operations are fantastic. They're the ones that are constantly doing this.

• 1:22:25Patrick O'Shaughnessy?

  We talked a lot about how you have changed your view on things in the last 18 years. What are you anticipating will change in the next 10? And what has you excited about the next 10?

• 1:22:35Speaker 02

  Look, my role is gonna change. 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 purchase of Red Ventures existing, I may not. Go to Facebook 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. And that's okay, right? It was meant to be for a period of time, so. I really don't know. And I think the next 10 years, I think AI is gonna disrupt every workflow, every interface, every platform, everything in ways that no one can predict.

• 1:23:18Speaker 02

  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. 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. Maybe some of the infrastructure.

• 1:23:44Patrick O'Shaughnessy?

  Rick, it has been so much fun to get this excuse to talk to you about what you've built, 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?

• 1:23:56Speaker 02

  Yeah, in fairness, I knew this question was coming. There's been so much, but instead of finding the one person, I'll tell you the thing. And it's forgiveness. I have been forgiven by many people, ultimately for being human. I've been forgiven by my wife for not being as committed 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 in the first decade. There's no manual to run a company. There's no manual to do acquisitions. I made a million mistakes and the grace that you give somebody when you forgive them is the most beautiful things we do as humans. So I am super grateful for the grace of forgiveness.

• 1:24:39Speaker 02

  And it's a great reminder that that's a power we have to give others. That is probably what I take with me.

• 1:24:45Patrick O'Shaughnessy?

  Coming here has been a total highlight of an otherwise fairly chaotic summer for me. You've created something really enviable and inspiring here. Thank you so much for having me and thanks so much for your time.

• 1:24:56Speaker 02

  An incredible honor to be on your show.

• 1:25:00Patrick O'Shaughnessy?

  If you enjoyed this episode, check out joincolossus.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.