From Gimlet Media, I’m Alex Blumberg, this is Without Fail, the show where I talk to athletes, artists, entrepreneurs, visionaries of all kinds about their successes and their failures, and what they’ve learned from both. 

<<MUSIC OUT>>

ALEX: I was recently talking with my co-founder, Matt, about this thing that sometimes happens lately. So you know, our company, Gimlet, is four years old, but we’ll still find ourselves in positions all the time, where we don’t quite know how to act. 

<<MATT: Yeah, I think a lot of, I’ll walk into a lot of situations I’ve never been in in the company and be thinking like oh what is a leader supposed to do in this situation, how is a person in my role supposed to behave.

ALEX: I do the same thing. My god. Cause you don’t, you’ve never done it before. You’ve don’t have really a role model and so you’re like what do I do here. 

MATT: Right. 

ALEX: And I find myself thinking should I be doing this in a way that I’m not doing. When I lived in Chicago I also used to think a lot about what would Michael Jordan do.

MATT: Like in the context of your life? Like how would Michael Jordan edit this radio story?

ALEX: Yeah, but I would think like, now that’s a winner. I want to be a winner. What would he do? I’m not even joking. 

MATT: One of the things that I do think about in situations is, I think about ski racers. If you watch ski racers, in like a big downhill where you are taking like big huge turns at like 60 to 80 mph. And you know the course. And what they do is they visualize the race. And so you’ll see them actually by the start gates, they are wearing skin tight clothes, it’s freezing cold. They are completely alone and exposed up on a windy mountain. And they’ll be standing in the snow, their knees are bent and they’re, you can see them visualizing in their head here’s how I’m going to take this turn, and here’s how I’m going to take that turn. Because they’ve done it so many times by visualizing they are able to make it real. And that I do a lot. If I have a big situation I’m heading into, like a big meeting or a difficult situation I will envision how it’s going to go multiple times so I can be prepared for all like what could happen.

ALEX: I didn’t know that about you.

MATT: Yep.

ALEX: God, four years. Still learning things about each other.

MATT: But then, so I’m often prepared for what may happen, but the drawback is that I’m not that open and present to what else could happen and I don’t get that emotional, I’m pretty much like there’s this turn and that turn and this turn and that turn as opposed to being open to what other turns there could be. 

ALEX: Living in the moment.

MATT: Living in the moment.

ALEX: Yep.

MATT: Do you think sports is a metaphor for life? 

ALEX: Umm. Well I’m not sure. I’ve often thought not. But I did have a conversation which we are about to play on this show with someone who made me think in certain places it may be a metaphor for life? I talked to Andre Iguodala you know the basketball player for the Golden STate Warriors, world champion. And he was also a sports is a metaphor for life skeptic. But then his mind was sort of, he came up with a way that it actually is. And we got to talking about that and I became convinced. 

<<TAPE: There’s the buzzer. There’s a new dynasty in the NBA. The Golden State Warriors champions once again, back to back titles.>>

Alex: Andre Iguodala’s team, the Golden State Warriors have won the championship 3 of the last 4 years. They’re routinely called one of the most dominant teams in NBA history. Their star players Steph Curry and Kevin Durant are cultural icons, on TV commercials for brands like Nike and Under Armour. Their jersey’s are some of the NBA’s best selling. The arena where they play in Oakland sells out every game. 

And Andre, while not the face of the team, has been called the super glue. He was the Most Valuable Player of the 2015 championship, putting him in elite company with Michael Jordan, Larry Bird and Kobe Bryant. 

Andre is also one of the sports world’s biggest investors. He took an early interest in it, and has made investments in companies like Apple, Tesla, and Facebook. He hosts a big tech summit for athletes. 

And he and I had a wide-ranging conversation where we talked about what it’s like to play for a team where everyone loves you. And what it’s like to play for a team where everyone does the opposite of loving you. And we got to a definitive answer on the question that Matt and I had, are sports really a metaphor for life? And I actually learned a real live management lesson that I will keep with me forever. 

So, without further adieu, here it is, my conversation with Golden State Warrior Andre Iguodala.

Alex: When when did you realize I'm a good athlete?

Andre: When I was a good athlete...I knew that at a young age.

Alex: How old. How old do you know?

Andre: I don't know 7, 8?

Alex: How?

Andre: Because I was like good at every sport. It just came natural. Like I played shortstop. So you get on the balls in baseball. Right. Played quarterback and receiver in football. One hand catches, I could throw the ball. The soccer team actually wanted me to be the goalie, in high school and I was like.. I'm not doing that. 

Alex: Andre was so good at so many different sports...that it took awhile for him to realize just how great he was at basketball.  But eventually he caught the attention of big division one schools, and then, the NBA. In 2004, after a breakout season at the University of Arizona, he entered the NBA draft. 

<<TAPE: Good evening ladies and gentlemen and welcome to the NBA draft at the theater at Madison Square Garden in New York City, home of the Knicks and the WBNA Liberty>>

He was 20 years old. And the way the draft works, for non sports fans. It’s just like on the playground when you are picking teams for dodgeball. Each NBA team takes a turn. The person who gets picked first, that’s the best player. You wanna go as close to number 1 as possible. Ideally in the top 10. Unlike playground dodgeball though, not everyone who wants to play gets picked. Each year, many many players looking to go to the NBA, they go undrafted. Andre though, he was projected to go pretty high.

Andre: I was projected like anywhere from three to like six. 

Alex: So everybody’s telling you you are going to go high.

Andrew: Right. So we get to like seven I haven't got picked yet. So I'm like man. You know someone sets the expectations for you and you don't know what to expect. It was like are you a bust? You know I'm saying like I had crazy thoughts like am I'm not going to get picked. 

Alex: Really. 

Andrew: Right. You know so Toronto comes at 8, cameras on me, and that's how you know you drafted to the cameras come on you. And I'm like Toronto? I didn't work out for Toronto. And there’s all that stigma of being in Canada, so I'm like nervous like no way. But Rafael Araújo was behind me. No one knows that name, but he was behind me and the one who got picked so. So then I get picked.. 

<<TAPE: With the 9th pick in the 2004 NBA draft, the Philadelphia 76ers select Andre Iguodala from the University of Arizona>>

...and then I don't know how to feel. It’s like did I go too late? You know what type of questions am I going get. When you get picked you go on stage shake hands and you see the draftees are talking to interviewers and reporters right there and its live. There's a live feed right there too so you can hear yourself. So as soon as I get done and I do a little interview, I heard Dick Vitale. 

Alex: Legendary announcer Dick Vitale.

Andre: He pops up. He goes crazy I can't believe the Sixers picked him. This guy’s a bust. 

Alex: What? Oh my god.

Andre: Right, right. So Dick Vitale went crazy, he broke down my states,  only shot 19 percent from three, just athletic, no basketball game. Right. 

<<DICK VITALE: Iguodala, couldn’t dominate on a collegiate level. I love his athleticism, but he averaged 12 points a game in a fast paced game with Arizona, shows you the thinness of this draft when the guys a lottery selection and he can’t dominate in college>> 

Andre: Funny thing is I ran into, I hadn’t spoke to Dick Vitale, two years ago I ran up to him. And I know he doesn't remember. 

Alex: Yeah. 

Andre: Came up and apologized.

Alex: Oh really. 

Andre: That was crazy. 

Alex: Are you kidding me?

Andre: He's like sorry I got you wrong, I'm like you remember that? That was 13 years ago. I thought I was the only one who remembered it. But I didn’t bring it up to him, he just approached me. I was like that's pretty cool. 

ALEX: It was cool when the apology came, but back on draft night, 2004, it was really confusing for Andre, and something of a harbinger for what was to come on his new team, the Philadelphia 76ers. See, the Sixers, they’d been coming off a pretty good run, consistently going into the playoffs and even making the finals, behind their beloved superstar, Allen Iverson. But Iverson, everyone could tell, was nearing the end of his career, and all eyes were on the 76ers new draft pick, Andre Iguodala to be the new superstar of the team. And Philly, it is a tough place to play. A huge sports town. They are passionate about their teams.

And in 2006, two years into Iguodala’s tenure in Philly, Allen Iverson was traded. And the press they zeroed in on Andre. Demanding that he fill Iverson’s shoes. And letting him know every time he didn’t. 

A typical headline: “Is Iguodala overrated?” or “Reliance on Iguodala defies logic.” Headlines called him a “little dipper” and “second fiddle.”

Andre: I could hide behind Allen Iverson my first two years and I was a big kid. Like I like to joke around and have fun. It was like you play too much. I been hearing that my whole life. I like to have fun and joke around. When he left it was like you know the main guy takes all the blame. 

TAPE: <<He gets a D. Andre Iguodala. I’m telling you. He is not making no big plays. He disappears. 

… The Sixers are promoting him as this is our star player this is the guy that is going to take us to the promised land. He’s not that guy. 

...Why does he think he’s Kobe Bryant when he’s not Kobe Bryant...

...Overrated I mean I like Iggy but he’s not a number one option. He can’t manufacture his own shot. To me. He doesn’t shoot well.>> 

Andre: Like I was fighting against them every night.  // 

Alex: Them being the media the fans or both?

Andre: More so the the media.  // You know you trying to prove them wrong and it's like wait why I'm trying to prove you wrong? I’m trying supposed to prove the other team wrong. So every night I was going against them when I was going against the other team. You know what I mean?

Andre: I had a game my teammate Reggie Evans was like man you got your teammates are open dog. Pass the ball you shooting too much. And I never shot that much. Like I was never the guy who shot too many shots. But I was playing against the media. I was like, man I'm getting 30 tonight.

Alex: Because you're tired of getting hammered in the media for not getting enough points? 

Andre: Right.

Alex: Yeah, that’s bad. 

Andre: So I'm like, so I'm like yeah and I'm yelling at Reggie like man, we going to lose they're going to blame me so I'm just trying to make sure we win.

Alex: Really.

Andre: I was, in Philly. It's like you got to win. So I was like trying to win. 

Alex: Right. 

Andre: So that it kind of shaped everything that you did. It could shape your life 

Alex: It's funny now when you're mentioning that like if like it's something I've heard before it just sort of clicked with me when you were saying it's like how public your job is. Right? Like you you don't, I don't have anybody watching me do my job on a day to day basis. And if they were they'd be like wait why, why are you watching that YouTube video right now you should be like you know if you're like preparing for this meeting or whatever. You know what I mean. If somebody was like just watching me every single second while I was doing my job like and then writing about it? Like that's crazy.

Andre: But then someone will say well that's what you get paid for. 

Alex: Right. 

Andre: And some athletes are able to tune it out and make some great. At the same time some athletes are able to lock into it and hear it and use it. And it’s great. But then the opposite some guys will block it out and it bothers them still because it’s still right there and some players are looking to it too much and it affect them.

Alex: Was there was there like a moment that you think back on in Philly that was like the absolute like where it was just like, this was my worst moment here.

Andre: I used to get cursed out a lot like a street like walking down the street. 

Alex: Are you kidding me? 

Andre: Yeah, it’d be funny. I thought it was funny.

Alex: Give me a time.

Andre: I was Richard McBride, my high school teammate. He came out to Philly for the first time. And he was going come to a game, we gonna hang out. So I'm telling Richie McBride like if somebody says something to you just be cool. He's like what? What you mean? And I'm like man, we lost last night. So it's going to get kind of hectic.

Alex: He's like what. This is your town right?

Andre: Here's what I left out. He was with his then girlfriend so she wanted to go to a museum. So he like, bro we going to the museum. So we do some sophisticated. And we ain't going to get cussed out at the museum. Bro, we going to the museum. I know this but we got to walk because we like downtown. So we got to walk. I'm like somebody says something just be cool.  

So we went to the Museum of Anatomy, like of the body. It was dope. We were walking down the street and this dude walked past, and saw me and just f you mother-f-er like you sorry mother-f-er. He was like he was like yo what he was like yo man was really good with these people? And then I got a couple of scowls. He was like yo man. Like I thought you were joking like he just start laughing. He was like man, we had this thing where I'm from we call it that we say that's league like man as league. Like that's crazy to the highest level. He was like man that's league, we just got cursed out two times today.

Alex: What do you feel like when that happens? 

Andre: I was used to it at that point. It happened so many times. 

Alex: So you just like. 

Andre: Yes. It was like alright man, I love you too. So there's an interesting dynamic with the Philly fans. It always gets out that I said this a tough place to play and then when I go there they're pissed at me. But I always say this as well as that I needed that. You know I needed Philly to kind of mature and grow up and it turned me into a businessman.

After the break, how Philly turned Andre Iguodala into a businessman, and how turning him into a businessman got him a championship. That’s coming up after these words from our sponsors. 

<<BREAK>>

Welcome back to Without Fail and my conversation with NBA player Andre Iguodala. When Andre Iguodala says Philly turned him into a businessman, a lot of that has to do with the fact that in Philly, he met his business partner, Rudy Cline Thomas. Rudy was running a business management company for some NFL and NBA players, including one of Andre’s teammates. Andre and Rudy met, hit it off. Had long conversations about basketball, fashion, tech. They geeked out over finance and Rudy became Andre’s financial advisor. 

Andre: So I've got Standard and Poors like Dummy to Investing. Read through that learned about large cap small cap, mid cap blah blah blah. I got an e-trade account and started investing in companies. And Rudy was helping me with it. Then I was like Apple. That's when the iPhones first started coming out, getting an iPhone one, iPhone two. You know the iPhone two plus, you start getting the iPad and then I read an article if you had all of the Apple products that you've bought. Say you have six Apple products and that totalled, I don’t know, three grand. If you took that money and just invested in Apple over the same period of time, this how much money you would have made.

Alex: Right. 

Andre: So it was around that time, you start seeing you know this is how you invest in startups. Because you see Apple stock you see like when did Apple hit the market. You're like who invested in Apple back then and how much is that money worth now? And I was like who would know to invest it back then? 

Who would know? Who even were the people who knew about these companies when they were just forming? And how could Andre become one of them? How could Andre move from being one of the millions of people who trades Apple stock on E-trade to becoming one of the handful of people who is able to invest in the next Apple. He knew Silicon Valley was the place for him to go to learn all about that. He had done some start-up investments, but he know to get really deeply involved, to make big moves, he was going to have to move to the Bay Area. And so, when he became a free agent, and he reached out to the Golden State Warriors. 

And Andre said, at first the Warriors weren’t interested. They couldn’t afford him. But then, his agent worked out a three team trade and in 2013, Andre found a new home at Golden State, where he was able to play for a new team and pursue his new interest, start-up investing.

Andre: And then Rudy e-mailed like every VC and..

Alex: And you're saying what?

Andre: We would like to sit down. I'm a new member of the Golden State Warriors. Really interested in the tech space, want to know how it works. Willing to do the groundwork, just want to get some access to how things work, maybe take an internship. So we went to Silicon Valley sent all those emails out, we got a couple of responses. I sat down with one company and the guy was like, I’m telling him the back story he's like stick to your E-trade account. Like that was all he said the whole meeting he was like stick to your E-Trade account but you know appreciate you guys inviting me but I don't think this is for you, it was like..

Alex: What do you think that meant?

Andre: Well you learned that this like that billionaire’s boys club is real. Like you know they keep people out for a reason. I don't think any of them were malicious and like no I don't want you to come in here because you're black. Right. But there's just more so I was an athlete. Right now you athletes you know, you guys this is different, like this is hard work. You don't see me coming over there playing basketball. Like Evan Turner. 

Alex: Fellow basketball player.

Andre:  Yeah Philadelphia. Unfiltered. But he was like he knows a rapper there who always hits him up like come up hoop with us come play basketball. He was like man I'm not playing basketball. This is like one of the top rappers out right.

Andre: He was like. Now what if I go to studio start making beats and I'll call you and say hey man come lay a verse for me? You're not going to get on the song with me. So this is similar, you know what I mean?  It's similar it's like some of these guys like you don't see me trying to play basketball with you and going to the NBA. This is what we do. We take it seriously we're the top of what we do. So you know, you do what you do. It was more of that vibe then I don't want you around here.

ALEX: But Andre persisted, and eventually he found a guy at a big VC firm who taught him the ropes, introduced him to a bunch of companies. But still, Andre wasn’t getting access to the best deals. The companies that had the best chance to become the next Apple. And that’s the funny thing about Silicon Valley, the thing most people don’t understand. It’s sort of the opposite of what a lot of people think. People think startups, they have to convince investors to give them the money. And in many cases that’s the truth, that’s the way it was for us for example. But if you are a super hot startup, all that’s reversed.  Investors have to beg to be allowed to invest in you.

The thing is lots of people have money to invest. These hot startups are looking for investors with something else to offer, technical expertise, or a track record of helping build successful companies. And Andre, he didn’t have that much to offer, besides his money. But then, the Golden State Warriors won their first championship in 2015. 

Andre: Once you start winning championships you start getting access. I know one company wouldn't let me and I want to get in so bad it was. Wouldn’t let me get in. He was... As soon as we won a championship I got an e-mail the next day. Hey man we about to close. You want to get in? Can you make a video, Instagram video with the product blah blah blah. It was harder to get in then expected but we got our foot in the door.

ALEX: Today, Andre and his business partner, Rudy Cline-Thomas have stakes in about 25 startups, companies like Casper and the Players' Tribune. 

And along the way, Andre started winning basketball championships. So, he’s successful in sports. And he’s successful in real life. Meaning he’s perfectly qualified to answer an age-old question. Is one a metaphor for the other? Is sports actually a metaphor for real life. The answer, from one of the few people who actually knows..after these words from our sponsors.

<<BREAK>>

Welcome back to Without Fail and my conversation with NBA player Andre Iguodala. 

Alex: How much of success in sports does it translate. Are sports a metaphor for life? Or is it just sort of like it's it's own realm.

Andre: Ok so once I won the first championship and then you know you get invited you get access to all types of things and you get to speak in front of Fortune 500 companies. You learn to make a parallel from the championship to anything in life. So I joke with guys like man listen man if you win a championship, you could give a speech on anything in life. So you can do anything you want. So it is funny, but in all seriousness, like we made it look easy now but the people have no idea how hard it is when a championship like that. It is so hard.

Alex: What is the hard part?

Andre: Well everything has to align. Like you've got the right draft picks in place, you got to have the right timing. Like it's like a lifetime of work. That's what people miss. Everything is a lifetime of work that goes into this. 

Alex: Right. 

Andre: And then we had to go through really hard times.

Alex: What was the hardest part about winning that first championship in 2015?

Andre: So, I never got a rhythm the whole season until the finals. I was always out of rhythm I was like man I've been averaging 15 to 20 points my career and I'm struggling to get eight. You know it’s killing me. But we're winning but it's like man like we are winning but are we going to win the championship? Then it is like we get to Memphis in the playoffs and we're down 2-1. We we had this number 300 passes or more we will win like we knew that, 300 passes or more we've lost one game in the last four years.

Alex: Wow. 300 passes

Andre: Three hundred or more passes 

Alex: In a game. 

Andre: In a game. 

Alex: OK. 

Andre: So I remember being in a meeting I was like Steph, look man you're the best in the league, but our shots are coming after one pass or no passes and you making, you making most of them. But you know there's not making Memphis work, they are a defensive team.

ALEX: You mean, meaning you guys aren’t passing enough. You aren’t making those 300 passes or more a game that is your winning formula.

Andre: Right. And I told him like listen when you pass to me what you think I’m going to do. I’m gonna do something and give it right back to you. 

Alex: Was it scary to tell him that it was it like that, was it weird?

Andre: Nah, because the way he is see. See Steph is like, man he's like as perfect as you can get to human being. It's weird. Like him and Grant Hill. You know I mean they come from great families don’t have egos, they work hard and they maximize their talent and so Steph and I have such a great relationship, it's easy to tell him something. There's no way to approach him but with respect because of who he is. So and it wasn't just him. Like Clay shoots quick, Steph take a quick shot. Draymond, he'll take a quick shot now. So you know it was it was a domino effect. 

Alex: It's like one of those things it's weird, because you guys know 300 passes you know.

Andre: And we'll go through 10 straight games two hundred and fifty pass and wonder why we 6 and 4 or 7-3.

Alex: How does that happen? Why does that happen? 

Andre: Just human nature. Yeah it's just human nature.. You got it you got a reel it back in and that's what takes having that type of culture that you have.

Alex: You know what else. Like actually I was a sports as a metaphor for life skeptic because I was like there's nothing in my life that has like I'm not doing what you guys are doing I don't have to make a split second decision with like five defenders flying at me. In fact, split second decisions in my life are probably bad. And like what works for me often is introspection and like trying to be like where where are my flaws, like slowing down. But like your story made me feel like oh wait there is something. And I noticed this tendency myself like when things are going wrong you have this tendency that like I got to fix it. We all become sort of Donald Trump, like I alone can fix. 

Andre: Yes. 

Alex: You know what I mean. I alone can solve. Yes. And like what you really need to do especially in those moments is like seek help. Go to your team. Because you can't do it alone.

Andre: Yes. I relate to that story more than anything. So people always say how’d you sacrifice being a superstar or on the brink of being a superstar, playing in the Olympics, making an all star team, to being a sixth man. I always say listen man you might be an engineer in a back room. You don't understand the impact you have on a company because some people are natural superstars. Some people want to be known for that. It’s like listen this is what I bring to the table man I want people to know that. And you keep giving him all the shine you keep giving him all the attention. And I've had CEOs come up to me and be like man I know this guy's really good. But I need him to just play the back role and not seek the attention right now I need him to just do what he does and there’s going to come a time when he can get it but it's just not right now. And he's thinking about leaving or he's getting attention elsewhere but he doesn't know, he doesn't know his effects because it's not out in the open. So I've given talks about like sacrificing for the greater good. Like taking a back seat so someone else can do their, get theirs right now. Then they take the backseat for someone else at the end of the day we all going to win. And that's what that passing thing is was like OK I give it out to you. You do your thing right now. I know you don't give it back. I’m gonna give it to him. And then when we're all we're all threats that's when we are our best. 

<<music>>

Alex: Life, there’s your sports metaphor.

<<music>>

Thanks so much for listening to that conversation with Andre Iguodala. 

Next episode of Without Fail.

Someone who saw a big problem, and set out to fix it, by himself. 

ALEX: So we went from 4 million students having access to 40. That’s almost 90 percent of students in America now. And it’s basically all because of you.

    EVAN: Well I wouldn’t say it’s all because of me.

    ALEX: I know you wouldn’t.

    EVAN: We’ve had a lot of help. There’s a lot of people who made this happen.

ALEX: There’s a lot of people, but none of them got the ball rolling. Like if you hadn’t gone on this mission a while ago, I think it’s safe to say we wouldn’t be anywhere close to where we are today.

    EVAN: Yeah, I think that’s fair.

Who is this guy? And what problem would likely still be unsolved if not for him? That’s coming up on the next episode of Without Fail. It’s a crazy story. 

Without Fail is hosted by me and produced by Sarah Platt. It is edited by me, Nazanin Rafsanjani and Devon Taylor.

Peter Leonard mixed the episode. Music by Bobby Lord. 

If you like Without Fail -- leave us a review! It helps other people discover the show. And speaking of helping other people discover the show, are you doing your part? Do you like listening to the show, do you enjoy it? Share it with your friends. Tell them about it. Don’t just keep it to yourself.

As always, thanks for listening.

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