Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Alex Rodriguez (AROD) on Investing Lessons from Warren Buffet, How a Meeting with Magic Johnson Changed His Approach to Business and The Single Best and Worst Investment Decisions he has Made and Why AROD Is Not Buying More Real Estate About this episode Alex Rodriguez is a businessman and the Chairman and Chief Executive Officer of A-Rod Corp, a broad-based investment firm that bets on world-class startups and partners with leading global companies across the real estate, health and wellness, technology, and sports & entertainment industries. While best known as one of the world’s greatest athletes (a 14x MLB All-Star and a 2009 World Series Champion with the New York Yankees), for more than 25 years, Alex leads a team of experts building high-growth businesses and is co-owner of the Minnesota Timberwolves. In Today's Episode with Alex Rodriguez 1.) From MLB to Business MVP: How Alex made his transition from one of the world's greatest athletes to the world of business? What does Alex know now that he wishes he had known at the start of his business career? What is Alex running away from? How do his insecurities drive him? 2.) Lessons from Magic Johnson and Warren Buffet: What are some of the single biggest lessons Alex has learned from his time with Warren Buffet? How did Magic Johnson impact Alex's approach to business? What is Magic Johnson's framework? How can others use it as a blueprint for their career? 3.) Alex Rodriguez: The Business Builder and Investor: What has been Alex's single biggest investing hit? What did he learn from it? What has been Alex's single worst investment decision? How did that change his approach? Why is Alex not buying real estate currently? How does he view the future of real estate buying? 4.) Alex Rodriguez: The Father and Son: How did having two daughters impact Alex's approach to business and life? What have been Alex's single biggest lessons from seeing his single mother operate? How does Alex reflect on his own relationship to money? How has it changed?
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 I think I learned from Warren a few things. He always talks about sticking to your circle of competence. Note number two, he always talks about buy the best and forget the rest. And then he always talks about separating emotion from investing. Being a great investor, companies, stocks, they don't care about your emotions.
0:19 Harry Stebbings? I mean, I am excited for the show today. It is not every day we welcome one of the greatest athletes of all time to the hot seat. Alex Rodriguez joins us in the show today. Alex is a 14 times MLB All-Star and is a 2009 World Series champion with the New York Yankees. And in the world of business, Alex is the chairman and CEO of A-Rod Corp. And is co-owner of the Minnesota Timberwolves. This was an amazing discussion with lessons from Warren Buffett, Magic Johnson, incredible investing lessons, both from wins and losses. But before we dive into the show today, you've heard me talk about Coda and how Coda is the doc that brings it all together. Well, it helps your team run smoother and be more efficient. I know this because Coda helps me. At 20VC, we do so many references before each show and that leads to a ton of data.
1:03 Harry Stebbings? It needs to be easy for everyone on the team to access and draw from. Coda makes this a dream. And so here's how Coda can help your team run smoother and be more efficient. Coda allows your team to operate on the same information and collaborate in one place by putting all of your data in one centralized location, regardless of format, eliminating roadblocks that can stop your team in their tracks. So you'll never need to ask, where are the latest project updates? Anyone know where the performance stats are? This is what slows down productivity. And with Coda, your team can operate on the same information and collaborate in that one place to get across the finish line faster. Help your team run more smoothly, more efficiently with Coda. Get started for free by heading over to coda.io/20vc.
1:45 Harry Stebbings? That's coda.io/20vc and get started for free. And speaking of tools we cannot live without, Angel List is fast becoming the center of the venture ecosystem. So for startups, Angel List reduces the friction of cap table management, banking and fundraising all in one place. Teams can focus on scaling and let Angel List handle the rest. Thousands of startups have moved their cap tables to Angel List in the past year. Angel List also supports large Venture funds and their teams with an automated software first approach and the best customer service in the industry. Fund managers can focus on making great deals while Angel List handles reporting, taxes, compliance and more. What's more, with the recent release of Angel List Network Banking for fund managers and investors,
2:26 Harry Stebbings? your deposits are secure with the most trusted banks for maximized FDIC coverage and mitigated single bank risk. If you're ready to scale your startup or fund with the platform at the center of it, visit angellist.com/20vc to get started. And finally, Brex. Since its founding, Brex has been committed to helping startups launch and scale faster at every stage of growth, from MVP to IPO. Today, Brex's all-in-one financial stack is used by one in four US startups and counting. I get to speak to founders all day and I know how crucial it is for them to have the right financial stack. Brex gives you fast access to a high-yield business account where you can safely store and move your cash while getting up to six million in FDIC protection.
3:09 Harry Stebbings? Lately, it's been all too clear how important that is. Plus, you get high-limit corporate cards, easy expense tracking and automated bill pay. To learn more about the all-in-one financial stack for startups, visit brex.com/20vc. That's B R E X dot com slash two zero V C.
3:33 Speaker 00 You have now arrived at your destination.
3:36 Harry Stebbings? Alex, I am so excited for this. I heard so much from Mark Rory, your partner, before the show. So thank you so much for joining me today.
3:43 Speaker 00 It is my pleasure.
3:44 Harry Stebbings? Now, I always like to dive in at the deep end, Alex, and so we look at your incredible history and career, but I always believe we're a function of our history. But what are you running from, Alex?
3:53 Speaker 00 Yeah, I mean, I think for me, probably where my heart and mind goes to is, you know, dad leaving at the age of 10, when I was 10, and leaving my mother and my two siblings behind. And I was the youngest of three and I thought that was a pretty significant part of my life that kind of, for better or worse, had a huge impact in my life.
4:16 Harry Stebbings? How did that shape your mindset? Because that is such a significant moment very early.
4:20 Speaker 00 I didn't really get to unpack it. If you fast forward all the way to 2014, when I got suspended from Major League Baseball, the longest suspension for PD use. It wasn't until then that I had a real opportunity to dive into the deep end of the pool, turn the lens inward and met a guy, a doctor that really saved my life. His name is Dr. David. Unfortunately, he's no longer with us. He passed within the last 24 months. But he really changed my life and helped me unpack a lot of the things that happened due to that exit of my father when I was 10. And then more importantly, helped me rewire my brain. And I worked with him for more than six years extensively. I think that's where my brain goes.
5:03 Harry Stebbings? How do you think you changed as a result of that time working with him?
5:07 Speaker 00 Completely changed. I would say, Harry, that pre and post-suspension, I'm a completely different person, completely different person. And it starts with just appreciation, being grateful. The definition of winning and success is wholly different today than it was before my suspension. Before my suspension, I thought winning and success was exactly what I said, winning a world championship, winning a big contract, having nice cars or a nice house, dating beautiful women. What I understood post-suspension, post-Dr. David, was that I was completely out of my mind. And none of that is really winning and success. While it sounds nice and it's fun, success today is really built more around gratitude,
5:52 Speaker 00 others around me, winning, collaboration, being a present and loving father. Completely different.
5:59 Harry Stebbings? Do you have to practice that? Because I'm with you. It sounds wonderful and gratitude and, you know, appreciation. But when you're kind of in the grind, you're an athlete, Alex. I'm not an athlete. I know I look it, but I'm not. But I'm a grinder. It's not that easy to be like, oh, I really appreciate this and I'm so grateful for this. It's I want to win. But how do you actually bring it back to that today and ensure that you do remember that?
6:22 Speaker 00 I think it's really about priorities. And it's much easier, I would say, to say this in my 40s versus 20s and 30s.
6:29 Harry Stebbings? Because.
6:30 Speaker 00 The thought that I always share with my team is this whole idea that I see a lot of young people make this mistake where they go wide and shallow and they try to be experts at all things. And we always talk about at A-Rod Corp, narrow and deep. And what are the priorities? What are the two or three things that are most important to me personally, to my family, to my company? And you can be great, in my opinion, at 10 things. But if you work really hard at one or two of them, I think you can be great at. So it's priorities and really simplifying and slowing down to speed up.
7:03 Harry Stebbings? Can I ask, when you think about kind of where people are really great, those one or two things, I look for spikiness in people when I hire today, which is those one or two things. What advice would you have for me when you think about assembling great teams as a founder, as a CEO? What are your lessons on finding people's one or two things and bringing them together?
7:22 Speaker 00 I've been very fortunate, playing professional sports for over 25 years, that you end up with this experience where you have pattern recognition. Now, that's not enough. You're able to see really talented people who are hungry and gritty. But my partner Mark Laurie has taught me a lot about reading resumes. The key is the 10s and the 5s are easy to recognize. The 10s, you know, jump out of the page, and the 5s are people you're probably not going to hire. The challenge is when you have the 6s and the 7s. And if the 6s and the 7s have the gift of gab and are good people, they can trick you over a series of two or three interviews. So one thing I would say, hire
8:04 Speaker 00 slow, fire fast. I would avoid, even interviewing, as you read through your hundreds or thousands of resumes, I would eliminate hiring 6s, 7s, and 8s. And I would focus on just the best of the best. That way, at least you're in a pool of people that you want to hire, then it's just a matter of culture fit for you.
8:26 Harry Stebbings? You mentioned Mark May, your partner, one of the most skilled resume readers I think I've ever met. He did mention to me that you're one of the most skilled dealmakers that he's ever met and negotiated. Can I ask, what does great deal making look like and mean to you? You mentioned how your definition of success has changed. What does great deal making mean to you?
8:44 Speaker 00 Well, I think it's empathy and compassion, really connecting with the seller or the buyer and really understanding, I don't think, Harry, you can make a good deal with a bad guy. That's number one. Number two, I do believe in this concept of win-win. If I'm trying to make a deal with you, Harry, and I don't understand that you live in Chelsea in London and you're this great athlete and things are important to you. I need to know what are the things that are important to you? And understand what are the three most important things with this transaction that mean the most to you? And I'm going to start there. But if you have 10 things that are important to you, it's hard to meet all 10. But I can certainly focus on the top three. And I think working from there and then working backwards is really important. But also being a good listener.
9:28 Speaker 00 I think so many people are busy with, you know, running their mouths. I found that the greatest entrepreneurs and the greatest negotiators are people that are good listeners. And then try to work out a structure. Sometimes the price is not negotiable, but sometimes terms are. Sometimes the price is negotiable, but terms aren't. And if you just go full speed ahead and you don't understand the rules of engagement, I think you're not giving yourself the best shot.
9:52 Harry Stebbings? I know it varies by situation, but would you say you are a head or a heart person when it comes to decision making?
9:58 Speaker 00 I think back when I was, if you go back 10, 15, 20 years, definitely heart. I think today I'm a combination of head, heart and just some common sense.
10:08 Harry Stebbings? What was the best deal that you did when you were flat? And what did you learn from doing that?
10:14 Speaker 00 The best deal or one of the best deals that we've done here at ARO Corp. Is we bought a third of a business called Petro's Pace almost five years ago. And we bought a third of the company and it was a lending brokerage business that was ESG and green. And it would lend to real estate owners and it was a great substitute to mezzanine debt. In a world where in mezzanine debt you pay mid teens, you were paying perpetual space money about five or six percent. Of course, this was before the Fed has raised rates tremendously. And so if you're looking at a loan that is not personally guaranteed, it's half the price of mess debt and it's green. It makes the world a better place. I really liked it. I love the two founders. We backed them.
10:59 Speaker 00 And then this year we sold it to Apollo for almost, you know, 12 times.
11:04 Harry Stebbings? What was the worst deal?
11:05 Speaker 00 I think the worst deal came around the financial crisis in real estate. It was around oh eight. We acquired a beautiful, beautiful portfolio of about a thousand apartment units. We paid around $60,000 per door. It was right around Yankee George Steinbrenner Field in Tampa. It was a beautiful portfolio. It was the right assets. It was the wrong timing. And what happened was we woke up about two weeks later with the crash and the assets were worth probably $40,000 per door. And we owed 42,000 per door. So we were underwater. That was probably the worst. Thankfully for us, we had enough capital to negotiate with the banks.
11:47 Speaker 00 And we ended up selling that like five years later for about 75 a door.
11:51 Harry Stebbings? That's a worrying moment. In those worrying moments, I find it very reassuring to have bluntly mentors who've been there, done it, seen it. You have some of the most exceptional mentors Mark was telling me. He told me Magic Johnson, he told me Warren Buffett, John Gray, Barry Sternlicht. I wanted to unpack lessons from them. If we go to Magic Johnson, what's he taught you? And how have you changed having learned from him?
12:16 Speaker 00 I love Magic Johnson and he is a very dear friend. He was my hero and Harry, what Magic did for me is he gave me hope. In my neighborhood, you did not have a lot of role models that wore suit and tie every day to work. There were a men of color. And then when you go into having a Hall of Fame basketball career and then taking that to a Hall of Fame career in business, the first thing he gave me was hope. Cause I said to myself, boy, if Magic can't do it, why can't I? That was very important. The second thing he did for me, as we then became very good friends, I had a very important meeting with him that he taught me framework. And he basically gave me his floor plan on how he took Magic Johnson,
13:00 Speaker 00 the Hall of Fame iconic basketball player, to a Hall of Fame iconic businessman. And this was in a course of a three-hour dinner that we had in L.A. near Rodeo Drive. We went to a steakhouse. We had a back room. Lon Rosen, his longtime partner and agent, set this meeting up. And it was a 30-minute meeting. It lasted around three hours. And years later, I asked Magic, I said, Magic, I am overwhelmed. I was so nervous to ask you, but I have to ask you now, why did you give me three hours when it was a 30-minute meeting? And he said, Alex, you're the only athlete that I've sat with that came in with a notebook and had like nine pages of notes. So I felt I had to cancel my other engagement and I wanted to really lean in and try to help you
13:43 Speaker 00 because I thought you were really sincere and present.
13:46 Harry Stebbings? What was the secret to his framework? Because it's clearly worked so well for him and for you, but respectfully, it doesn't work for everyone. You are very few people who've succeeded in the way that you have in this business and making that transition. What was his framework and what has worked from it?
14:01 Speaker 00 There was three things. He said, number one, you have to find the best people in the world to come work with you, end of story, and don't compromise that. They won't expect that from former athletes like us. He said, number two, lean into your superpowers. Mine is basketball, yours is baseball. So go out and be the best baseball player you can. And when you have an opportunity, it'll continue to do television work when you're done playing so you can stay connected to the next generation of baseball fans. And thirdly, he said, come out and do these kind of things, Harry. Go out and speak to the Goldman Sachs, the J.P. Morgans, the private equity community, and stay connected and stay informed and continue to stay in front of the smartest minds and continue to practice what you preach.
14:44 Speaker 00 So those three things, I wrote them down in my notes and I've tried to execute those over the last 25 years.
14:51 Harry Stebbings? That must have been such a cool lunch.
14:54 Speaker 00 It was a dinner. It was a dinner.
14:56 Harry Stebbings? I mean, that's a, that's a fun one. Warren Buffett, I mean, Warren Buffett is most, you mentioned kind of the private, I believe, it's most of our heroes. I grew up on Warren and Charlie's lessons. What have you learned from Warren?
15:08 Speaker 00 Pulse.
15:09 Speaker 00 Warren's the absolute greatest and I've had an opportunity more than a handful of times to sit down with him and spend five, six hours in a day where he's literally going over all my books, looking all over the real estate and just really giving me feedback. I think I learned from Warren a few things. He always talks about sticking to your circle of competence. That's always been really important. I think number two, he always talks about, you know, buy the best and forget the rest. The saying that he says is, I'm better off buying a great business for a fair price than a fair business for a great price. And that's, that's been true so far in my career. And then I would say this one I would share with you is, he always talks about like in sports, separating emotion from investing. And the same is true for sports, baseball, basketball, anything.
15:57 Speaker 00 And what he means by that is being a great investor, companies, stocks, they don't care about your emotions. He always talks about emotion. Great investors usually have their emotions in check. So those are three things that I'm enjoying sharing with you today.
16:13 Harry Stebbings? When, when I look to your portfolio, which your team kindly sent over before, the one thing that's staggering is the breadth from the real estate to the kind of venture and P investments to everything in between. There's a lot. How do you think about prioritization and where your spiky self is? Where are you best in business? You said that you're best clearly baseball, but now you're a business leader. Where are you best in business?
16:35 Speaker 00 I think if you take a step back to when I started my business career about 25 years ago, early on, I wanted to have it like a pyramid where at the very bottom, I would try a bunch of things and put some very small bets, 50, a hundred thousand dollars in a number of companies that I wanted to, A, get a good return, but B, get a fair understanding of the business, of the space, of teamwork. And that's what exactly. Has happened over the last five years. We've really kind of worked this triangle where we're we're only doing things that we're passionate about, that we understand really well, that we have a competitive advantage, and where we can bring real, real value to the founders.
17:17 Speaker 00 What that looks like today at A R Corp, we do two things. We do sports and we do real estate. Sports, I've been doing for my entire life, pretty much. And real estate, I'll tell you, when I was seven years old or so, I always thought about, you know, real estate, because we were lifelong renters. We always rented. My mom had two jobs. I always dreamed about trading places with the landlord. And then sports, I was playing baseball. So if you could go, if you now cut forty years later, when I'm forty seven, I'm doing exactly those two things, real estate and sports, and are thrilled to to be in those spaces.
17:52 Harry Stebbings? Oh, I mean, you look incredible for forty seven. Clearly, the facial moisturizer is working. But I do have to ask, you mentioned switching places from the renter to the landlord. Now you're the landlord of most of America. I've been looking at the portfolio. How do you think about your relationship to money? How do you embrace your relationship to money today? And how do you think about that?
18:12 Speaker 00 Look, money is obviously a necessity. We always say we got to keep our lights on and all of that. But my relationship with money has changed over the years, because what money allows you to do is to have, you know, more time. The most important asset we have in our lives is our time and the ability to spend time with those that you love and respect the most. For me, those are my family, my daughters, and our team here at A R C. But money doesn't care about me, it doesn't care about you. And so I found that when I really worry, think about process and not results, both in baseball and in business and investing. If I have the best team and we're collaborating together and we have a very sound process and we're laser focused, I would make the bet that in the long run, maybe not in the short run,
18:56 Speaker 00 but in the long run, the success and the capital and the resource will follow.
19:00 Harry Stebbings? What's the hardest thing with process, Alex?
19:03 Speaker 00 I think it's discipline. It could be mundane, it can be boring, it could be. We spend a lot of time here in coaching. We have a lot of young, talented people. We like to develop our young talent, just like we do in sports. We take a lot of things from the sports world and bring them to our world here. Coaching, sympathy, compassion, all those things are important in leadership. The ROI on that is tenfold. I think if you spend the time on the front end, I think the back end is pretty sweet.
19:28 Harry Stebbings? You mentioned that kind of the transferability of skills and mindset from sport to business. I think the one that's really interesting for me is when you're down, when you are losing in either. What is the mind talk that encourages you not drop your head, not lose confidence? When you think back to days in sport and today, what do you tell yourself when you're down and you're losing to get yourself back on even?
19:51 Speaker 00 I think there's a few things when they're not going in your favor. Some of the things you gotta do is just slow things down a little bit. Continue to be grateful and appreciative. And this is hard when things are going bad, right? But you take a step back and say, I live in this great country. I'm healthy. I have family and friends that love me and respect me. And if you take it all away from from me, everything should be just fine. So just a little bit of gratitude always helps. And then I would double down into your health and wellness. Really making sure that you're having enough sleep, you're drinking enough water, you're well rested, you're getting your exercise in. Because the more you invest in yourself, the more you're able to deal with real challenges. I think that's kind of been my my way.
20:33 Harry Stebbings? Ah, do you believe in work-life balance?
20:36 Speaker 00 Yeah, I do. I do. But I mean, sometimes there's times where you have to sprint. And sometimes it's more of a marathon. But you have to be able to have the experience, the team around you, the strategy. That when it's go time and Mark, Laurie, my partner, talks about sixth gear, you have to go to sixth gear. But then it's okay to actually enjoy some of your success. To be able to have fun in the culture, to be able, we play music here at the office. Because we want the office to be a place where we celebrate each other. We work hard, we push each other, we keep each other accountable. And like sports, when people mess up, we have an environment here that is safe to mess up. Because we're not trying to, we got you. What are the lessons?
21:19 Speaker 00 Just like in sports, we lose two in a row, we're gonna get to practice and we're gonna fix this. But we're gonna fix it collectively as a team, not to embarrass you, but to help each other out. Because the better the team is, the better we're gonna be as a company.
21:31 Harry Stebbings? How do you create an environment of safety where you do have that, but also not an acceptance of continuous losing? You know, if a coach loses 10 games in a row, we might need to cut him. But you want him to try. How do you create that balance?
21:44 Speaker 00 Yeah, I think it starts at the top, right? We talked about higher and slow. And then it's cultivating that talent. How do you create an environment? I think it starts with a leader. And the leader has to be able to stand up and say, hey, I take full accountability. This is on me. And the more vulnerable you are with your team, it creates an environment where they feel safe. That doesn't mean you have to spill your guts in front of everybody, but it means that at times there's challenges. And to be able to come to your senior report person or to someone like myself, you want to have that culture. You want to have that trust. I've had coaches, heading coaches, managers in baseball, that I knew they had my best interests at heart. And because of that, if they said jump, I would say, I'll high. And I would do it without thought.
22:29 Speaker 00 The opposite, Harry, is also true. I've had coaches that I felt they had my worst interests at heart. Anything they told me, I questioned. So when I take that thought process to the business world, it's exactly the same thing. The first thing that people, that you have to think about is, Harry, if you and I work together, do you really think that I have your best interests at heart? If the answer is no, we're done. So building that trust early, building that bridge is vital.
22:55 Harry Stebbings? Penultimate one, you mentioned that kind of best interests at heart. I'm a little bit concerned about the future of the sports industry because we see this flood of PE capital coming in, respectfully largely from our dear friends across the pond in your wonderful nation into English football. But buying English football clubs and just buying sports franchises. And it's kind of, sport is becoming such a business today, unlike ever before, which has its pros and cons. How do you foresee the next few years in terms of the business of sports franchises and where the opportunities are in your mind?
23:27 Speaker 00 I think you have to thread the needle, Harry. I think what's beautiful about sports, it's the great passion, these progressive owners over the years. I can just tell you here about America. When you think about Dr. Buss with the Lakers, when you think about George Steinbrenner. With the New York Yankees, Al Davis with the Raiders, Robert Kraft, Jerry Jones, Jerry Reisdorf, so many great ones. You have this heart and passion connected to the franchise, which connects with the fanbase. You think about what Jerry Reisdorf has done with the six championships with Michael Jordan. Jerry and Michael were very much tied at the hip. It would be different if it was Michael Jordan tied into Blackstone. It just doesn't have the same feel, and I think Blackstone is the greatest of the great.
24:09 Speaker 00 But if there's a combination, Harry, where you can still remain and keep the Robert Krafts, the Jerry Joneses, the Bus family still involved in the forefront. And because these franchises have exploded in enterprise value, then I think it's a good mix because you get the capital from the institutions, but you still get the passion and the follow through from the Robert Krafts of the world.
24:32 Harry Stebbings? What do you think that looks like in five years' time? How do we see sports franchises evolve? And what does that landscape look like?
24:39 Speaker 00 I'm not sure because if you asked me that question five years ago, I would have been completely wrong of where we are today. The truth is, in the middle of COVID and this, you know, direct to consumer and what's happening to the regional sports network deal. Five years ago, while some people saw some of it, I think someone would be lying if they said I forecasted everything. I think we've seen more changes in the last five years than we've probably seen in the prior 30 years. I think the same is going to be true here in the next five years. A lot of this enterprise value is driven by television, by the national television deals. So it'll be interesting what that landscape looks like in the next five, 17, 10 years. But I do think that there's going to be a world where it's going to be a lot more franchise, direct to consumer.
25:23 Speaker 00 And that means with the way you watch the sport, how you interact with players, how you interact with buying merchandise and everything in between.
25:33 Harry Stebbings? Is there anything you're worried about when you look at the sports franchise landscape and how it could evolve?
25:37 Speaker 00 I always think about the fanbase and we can never. By the way, my same concern, Harry, about sports is my same concern about real estate. I have to think about my mother. And my mother was someone who had two jobs and we come from. Very modest economic background and we cannot forget about my mother. My mother is a figurehead for someone who can't afford her apartment or someone who can't afford to come watch their favorite sports team. We have to always make sure that we have enough to make sure that we don't eliminate ninety nine percent of our fan base, which is someone that has to consider affordability.
26:15 Harry Stebbings? Do you see the unfairness of life now? I was having a chat to a friend of mine, he's a billionaire hedge fund manager last night, but I was like, interest rates rise, everyone poor, their mortgages go up and we sit here with a ton of cash going, this is great, we're getting five percent now, just the rich just get richer. And I came from nothing too, and I'm like, God, it is unfair.
26:34 Speaker 00 Yeah, it is tough and you have to think about, you know, the local couple that both of them were professors or teachers at the local high school or junior high and the local nurse. And if you have a mortgage and you're a homeowner and you have a five year fix and you have a balloon payment in five years and all of a sudden you go from two percent to eight percent, you can no longer afford that house. If those are things we have to consider as leaders, as government, you have to think about the people that cannot afford these type of movements because they've gone through all their expenses, they've gone through all their liquidity. Most people have four or five thousand dollars in their bank account. So how do we create a world that helps that person?
27:15 Harry Stebbings? Final question before we do a quick fire and you've mentioned your girls several times. I've heard you talk about them before. How did becoming a father impact your mindset towards performance, business and how you operate?
27:27 Speaker 00 Well, I think with my background and dad leaving when I was ten, ever since I was eleven, twelve years old, I remember thinking to myself and making a promise that if I ever had the privilege to be, become a father, that would be my number one responsibility to be a present father and raise, you know, a son or girls. I happen to have two daughters, eighteen and fourteen. That's my number one priority in life and I do believe in today's day and age, probably at every day and age, the most important responsibility we have in this world is to raise, raise our children and everyone talks about fixing the world, but I think it starts at home. It starts at the Dinner table is starts with putting the phone away is having a conversation. And this thing is really important because I see where 95% of kids quit their sport on the ride home with their parents.
28:12 Speaker 00 If there's parents out there, one of the reasons why I think I made it to the major leagues, the gift and the curse of not having a father and having my mother work in two jobs is I never had this, you know, win at all cost when you're, you know, a 10, 11 year old boy. So for the parents out there, I would say be really thoughtful on how those conversations go after practice or after dance. It shouldn't be like, did you win? Did you get an A? Did you do this? It should be like, you know, what are the most enjoy? What was the most enjoyable part of your day? Did you work hard? Did you prepare? Did you enjoy? It shouldn't be about results, results, results. That creates a lot of anxiety for young people. And I think the gift and the curse of not having dad around, I think that was one of the main parts where I think I did have a, a long, you know, fruitful career in baseball.
28:57 Harry Stebbings? How do you engender the same ambition and hustle in your girls when respectfully they're brought up in different financial environments to, to how you were brought up in?
29:05 Speaker 00 I think it's less about what you say and more about what you do. Rachel, who's sitting here next to me, has been working with us for years and I love her for a lot of reasons, but one of the main reasons I love her, she's really fair and tough with my youngest daughter, Ella. And Ella comes home and complains like, oh, Rachel's being this and this and she's not being fair. And I go back to Rachel, I said, Rachel, congrats, you just got a bigger bonus. Because that's exactly what my daughters need. They need people that are straight, that are real. Because, you know, fortunately and unfortunately, they didn't grow up how we grew up. So the more, in a weird way, the more they lose and the more they can learn from those lessons early on, the more people can be straight with them and not BS them, the better they're going to be.
29:50 Speaker 00 So Rachel's helping me and Cynthia become even better parents.
29:54 Harry Stebbings? Listen, we're going to do a quick fire answer. I say a short statement, you give me your immediate thoughts. So dead or alive, you can have dinner with any person. Who's that person and why?
30:03 Speaker 00 I, I would say Jackie Robinson because Jackie was a four sport athlete out of UCLA and he was obviously the first African American. So in many ways he, he broke. The barrier for all of us and I would be curious what courage it took for him to play baseball such a high level, be a champion and deal with so much hate.
30:20 Harry Stebbings? What have you changed your mind on in the last 12 months?
30:23 Speaker 00 I think our strategy on continuing to buy real estate assets, I've basically put a pause on everything and we're sitting back and just watching and seeing where the Fed goes with interest rates.
30:34 Harry Stebbings? Purely because of the interest rate environment or?
30:36 Speaker 00 I think there's still a disconnect between buyers and sellers. Buyer sellers still think their asset is worth 10 bucks and we think is worth three. When that closes, eventually they'll call you and say, I'm ready to sell now for eight. And then we'll say, okay, we're not ready yet. And then they'll call back and say, okay, we're ready. We'll sell it to you for five and we'll say, we're not quite ready yet. And eventually they'll call and just say, okay, we'll take the three and then we'll say, okay, well, wire the money. We know the, we know the asset and we're ready to go.
31:02 Harry Stebbings? Go slow to go fast. What most painful lesson that you've learned that you're also pleased to have gone through?
31:07 Speaker 00 I think the suspension, my suspension for PD use, you know, Rob Manfred suspended me, the commissioner for, for an entire season. That season allowed me to, I really think lessons learned, taking full accountability. My therapy with Dr. David really set me up nicely.
31:25 Harry Stebbings? You're a really rude question. You were so good. Why do that?
31:29 Speaker 00 I think that's something that it was a really silly, dumb decision. And that's kind of part of the therapy, right? That I kind of, today I am a changed person. I would never do that. What was most rewarding for me, Harry and I've come to the place where I've forgiven myself. The most important thing that I think about my baseball career is what happened at the very start when I was 19 and what happened at the very end in my last season. At 19, I came second in the MVP to Juan Gonzalez and I was just a skinny lad. Hit 358 and won a batting title. And then as a broken down guy at 41, playing for the Yankees after two hip surgeries and two knee surgeries,
32:12 Speaker 00 I won the MVP for the team, hit 33 home runs and brought them back to the postseason. So Harry, to your point is when I think about, I don't need. Any of that stuff because at nineteen and forty one, I had two of my best seasons, completely clean and in a great frame of mind. Makes you go back and go, boy, why was it, what a knucklehead. But you know what? That mistake now sets me up for the back nine of my life. And I've never been in a better place, happier, more grateful. And if it cost me the Hall of Fame, I have no one to blame but myself. But if it can help the next generation avoid some of the mistakes that I've made, then ultimately there's, there's a lot to play for.
32:52 Harry Stebbings? What one word would be on your tombstone, Alex?
32:55 Speaker 00 One word, oh.
32:57 Harry Stebbings? Like mine's persistence.
32:58 Speaker 00 I can't say team player because that's too, maybe collaborator. At least in my life, anything that I've done that's been horrific has been by myself. Anything that I've done that's been great has very little to do with me and really around the people that we've collected around the room to work as a team together.
33:13 Harry Stebbings? What do you want your legacy to be? What do you want to be remembered for, Alex?
33:16 Speaker 00 I think someone who is loving, fair and a, and a very good father.
33:21 Harry Stebbings? And then final one for you. If we do this in twenty twenty eight, five years' time, where are you and where's A R C?
33:27 Speaker 00 I'm probably right here at my office with the great team and hopefully with a world championship for the Minnesota Tim Bulls.
33:35 Harry Stebbings? Alex, listen, thank you so much for doing this. I so appreciate it and you've been fantastic to have on.
33:40 Speaker 00 Thank you, Harry.
33:42 Harry Stebbings? I mean, what an incredible and broad ranging discussion. I want to say huge thank you to Alex for putting up with my prime questions. If you want to see more from us, you can watch the whole video on YouTube by searching for two zero V C. But before we leave you today, you've heard me talk about Coda and how Coda is the doc that brings it all together. Well, it helps your team run smoother and be more efficient. I know this because Coda helps me. At twenty V C, we do so many references before each show and that leads to a ton of data. It needs to be easy for everyone on the team to access and draw from. Coda makes this a dream. And so here's how Coda can help your team run smoother and be more efficient. Coda allows your team to operate on the same information and collaborate in one place
34:23 Harry Stebbings? by putting all of your data in one centralized location, regardless of format, eliminating roadblocks that can stop your team in their tracks. So you'll never need. To ask, where are the latest project updates? Anyone know where the performance stats are? This is what slows down productivity and with Coda, your team can operate on the same information and collaborate in that one place to get across the finish line faster. Help your team run more smoothly, more efficiently with Coda. Get started for free by heading over to coda.io/20vc. That's coda.io/20vc and get started for free. And speaking of tools we cannot live without, AngelList is fast becoming the centre of the venture ecosystem. So for startups, AngelList reduces the friction of cap table management,
35:07 Harry Stebbings? banking and fundraising all in one place. Teams can focus on scaling and let AngelList handle the rest. Thousands of startups have moved their cap tables to AngelList in the past year. AngelList also supports large venture funds and their teams with an automated software-first approach and the best customer service in the industry. Fund managers can focus on making great deals while AngelList handles reporting, taxes, compliance and more. What's more, with the recent release of AngelList Network Banking for fund managers and investors, your deposits are secure with the most trusted banks for maximised FDIC coverage and mitigated single bank risk. If you're ready to scale your startup or fund with the platform at the centre of it, visit angellist.com/20vc to get started. And finally, Brex.
35:51 Harry Stebbings? Since its founding, Brex has been committed to helping startups launch and scale faster at every stage of growth, from MVP to IPO. Today, Brex's all-in-one financial stack is used by one in four US startups and counting. I get to speak to founders all day and I know how crucial it is for them to have the right financial stack. Brex gives you fast access to a high-yield business account where you can safely store and move your cash while getting up to 6 million in FDIC protection. Lately, it's been all too clear how important that is. Plus, you get high-limit corporate cards, easy expense tracking and automated bill pay. To learn more about the all-in-one financial stack for startups, visit brex.com/20vc. That's B R E X dot com slash two zero V C.
36:36 Harry Stebbings? As always, I so appreciate all your support and stay tuned for an incredible episode on Monday with the one and only Chris Pike at Pace Capital.
Previous 20VC: The OpenAI Memo: Why Invest? Is it too Late to Catch OpenAI? Are OpenAI's Models Truly Defensible? Does the Value in AI Accrue to Incumbemts or Startups - Application Layer/Infrastructure? What Happens with Regulation? with Vince Hankes @ Thrive Next 20VC: Why VC Subsidizes the Wrong Type of Business, Why Capital Gains Tax is Crazy, The Biggest Misalignments Between VCs, Founders and LPs, Why Business Model - Product Fit is as Important as Product-Market-Fit with Chris Paik @ Pace Capital Page updated September 29, 2026 · transcript and summary are machine-generated
