David Novak 0:04 

Welcome to How leaders lead where every week you get to listen in while I interview some of the very best leaders in the world, I break down the key learnings so that by the end of the episode, you'll have something simple you can apply as you develop into a better leader. That's what this podcast is all about. Today's guest is Hall of Famer and former world number one tennis player, Andy Roddick. Now you may remember him from his big personality on the courts, or from winning the 2003 US Open, or when he hosted Saturday Night Live. But these days, he's doing all kinds of other fun stuff. He's the CEO of the Andy Roddick Foundation, which supports kids in low income communities. He's co founded two companies, one in healthcare and another in commercial real estate. And if that wasn't enough, he's also launched sweetens co spirits and is out there making Tennessee bourbon. Can you imagine just pivoting from what you've known your whole life and jumping in headfirst into one new situation after the other? Well, Andy knows what it's like to feel out of place and uncomfortable doing something new. He asked lots of questions. He prepares diligently and he knows how to develop the right relationships. Now look, every leader finds themselves in new situations where we don't know the lay of the land. This conversation will show you exactly how to navigate them. The leadership lesson for today is don't be afraid to ask questions. Here's my conversation with my good friend, and soon to be yours, Andy Roddick.

Andy, thanks so much for taking the time to talk to me.

Andy Roddick 1:44 

I'm very happy. I'm a listener of the podcast. So I'm a little intimidated to be on I'm happy to be on. And I it's even more intimidating talking to a guy from Louisville about a Tennessee bourbon that you mentioned earlier. So I'll be humble, I promise.

David Novak 2:01 

I want to start with, you've launched this sweetens coke spirits. A Tennessee bourbon, you know, tell us the story behind the brand and and you know what in the world makes you think you could compete with the Kentucky bird?

Andy Roddick 2:16 

I think I'm just dumb enough to have tried to. You know, I was. There's a nine hole golf course outside of Chattanooga, Tennessee, called sweetens Cove, which is just a phenomenal addition to to the world of golf. It's, you know, there's no frills, there's no dress code, you come you can experience world class golf course architecture for a pretty affordable price. And we kind of stumbled upon this a business partner of mine named Mark Mark rivers, and he kept going back to this nine hole golf course. And I said, Is that Is that what we're gonna do? We want to be in the nine hole golf business. Is that Is that where he goes? No, I think there's a play past it. There was this tradition. On the first tee where in a show of fellowship, someone would have a sip of whiskey or bourbon or whiskey bourbon and, and they would leave the bottle behind. And so then the next person would do it. Obviously, this is probably before COVID. But But But anyways, at the end of the day, there would be these bottles and you'd mix it up and you would kind of finish around at the end of the day you would share. You would share whiskeys bourbons. And then after about a summer of that and drinking all sorts of nasty hot bourbon, I said, are we? Are we dumb enough to actually try our own and turns out we were we brought in an unbelievable distiller I call her a scientist, Marianne Yves, who blends our product guy. You probably know, Peyton Manning came on board as well. So it's been it's been a pretty fun process. And, you know, we're still a kind of a gritty startup, but we've had some fun.

David Novak 3:46 

Well, good luck with it sounds great. You know, Peyton sent me an email asking for some some shout outs for your bourbon and I will definitely do Kentucky you know, you know, Andy, I always like to kind of go back to the beginning. Could you tell us about your upbringing, and maybe a story about your childhood that that really influenced the type of leader you are today? Oh, gosh.

Andy Roddick 4:09 

You know, I'm not sure my my, my dad was a farmer from Wisconsin. You know, he was his father passed. So he was running his own own farm outside of Platteville, Wisconsin, it was a suburb of Platteville and Platteville is about 2000 people. So he was out kind of in the middle of nowhere, but very, very driven, hard worker moved around in the service ended up having it wasn't an original idea, but was attracted to this idea of a fast oil change. And so, you know, he ended up owning some Jiffy Lube properties, and that's what took us to Austin, Texas. But, you know, he was a he was a hard worker, you know, he said, Listen, you don't have to do everything we say but if you do choose to do it, do it, do it well and kind of commit to it. There was a lot of thought around hat playing and into dual sport as well as a team sport. And I know everyone likes to specialize early, but I think there was a conscious effort in our in our household not to actually commit too early to one or the other. Because my parents thought they actually taught different lessons, you know, in, you know, the individual athletics, you know, like tennis is more self reliance. And the others are how to be a good teammate how to be a decent human and kind of not make it all about yourself. So luckily, my parents were thoughtful about that,

David Novak 5:30 

you know, you came up obviously, fast track as a junior tennis player. What advice do you give parents raising kids in sports that have potential like you obviously did?

Andy Roddick 5:42 

Yeah, the question I get the most, and this this, it doesn't matter what the potential is, you know, you don't have to kind of have pro aspirations. But I get the question from parents, and it bothers me, I always get, how long should my my my child be playing every day? I said, as long as they are engaged, committed and happy. You know, I don't think it's a one size fits all, you know, calculation, and I'd say probably quality over over quantity. And I see that mistake made over and over which, especially in an individual sport, might lead to burn out a little bit faster.

David Novak 6:14 

You know, Andy, I want to hone in more on how you think about leadership. But first, it's us open time. And you won this grand slam event in 2003. Tell us something about the US Open, that you'd only know by being a pest champion.

Andy Roddick 6:31 

Oh, gosh. I guess that, I guess that feeling? I mean, my relationship with the US Open is, has been a long one. I know my mom, you know, bribed me one year with my grades where she said, if you did well enough, we're gonna go to the US Open. And that was in 1991, which was also the year that a guy named Jimmy Connors made that epic run to the semi finals and basically turned, you know, it wasn't Arthur Ashe stadium then. But what is what used to be became Louis Armstrong turn that into a little bit of a rock show. And so as a nine year old, I was inspired. I'm like, This guy can control the entire mood of a crowd by playing well and emoting a little bit and it absolutely blew my mind created a love affair. And, you know, from from those days of being let the last person into the stadium and being way high up, you know, 12 years later, it happened for me. And it was, I promise you, I didn't take it for granted. You know, when

David Novak 7:23 

you won the US Open, I know, you had to be euphoric. You just mentioned that it was an incredible experience. To some people, you know, when you get to the top like that you became number one, they actually get down in the dumps a little bit later, you don't get a little depressed. How about you have any impact like that on you? Or you just keep on the high? Oh,

Andy Roddick 7:42 

the only thing that gave you the press was that I got him Federer came along. No, I didn't really I didn't really get down in the dumps too much. You know, there was a certain level of pressure that as I already used to, because the very beginning of my career, there was a there were a couple of long shadows, that made it virtually impossible as far as expectation, you know, Andre peed the tail end of Connors neck where we had kind of such an a sense of entitlement in a great way, because I kind of grew up during this, you know, fan entitlement phase. But at that point, I guess I was kind of already used to expectations a little bit. You know, so my stress points came from trying to problem solve against guys that, that were just better than me, as opposed to from from any outside influence.

David Novak 8:29 

Well, speaking of that, and you're obviously a hall of favorite yourself, but you've beaten each of the players that would be on what some would say would be the Mount Rushmore of tennis, you know, Roger Federer, Nadal, Djokovic, you've beaten all these guys, what single biggest thing? Did you learn about what it takes to be a leader from each one of these guys,

Andy Roddick 8:53 

they do it in a different way. You know, Roger, is it's almost like he's the leader as far as an ambassadorship and that doesn't get bestowed upon you until you actually have the results also, but an absolute gentleman, he's the only guy that I've seen who is considered amongst the greatest in his sport that doesn't have that like burning intensity, right? You want the Jordan documentary back, and it's it you know, he punches a teammate during practice and he's just got this like beast inside of him that he can't control but he's able to kind of control it and it manifests itself in greatness, Roger, you know, I asked him about this one time when I was on your side of the microphone. He goes I don't know he goes in and this is something that blew my mind and it's why I'm not as pure there are many reasons why I'm not as good of him but this is one of them I said you know you don't have that thing that that intensity that you know that we see in Kobe that we see in tiger that we that we saw it you know, I see in Jordan, and he goes I don't know I hear these guys always talk about the fact that you know, I hate losing I hate losing. I hate losing. I don't like losing but I like winning way more than I hate losing. And I was like that's so simple in Knowing because it's because you're actually able to execute on that thought it sounds great, but I wasn't able to execute on that thought.

David Novak 10:07 

What about Nadal, though

Andy Roddick 10:10 

one of the most humble guys you'll ever meet, goes about his business. So it doesn't matter that he's won 1200 matches and 13 French opens, he goes, he literally goes into the first round of the French Open going, I could lose today, and he has that kind of like, doesn't matter what you did yesterday, today is a different story. And he said it for a long time. And I didn't really believe him. And I think I do now. You know, I actually think he respects the process. He respects his opponents, he knows he's still playing against the best in the world. And on an off day, you know, he has this kind of like, admirable insecurity about himself. And I think that's the right way to put it. That kind of makes any alien for me, I'm going gosh, I wouldn't want slamming was number one for a cup of coffee. You know, why should I have an ego about anything when this guy kind of takes his lunch pail and his hard hat to work every single day? So I thought that was very admirable. And you know, it hasn't changed over time. How about the jockey that he has his unbelievable ability to kind of, you know, I think there's a divide, you know, he doesn't like the fact that Roger and Rafa get all the adoration and the fan support, and kind of instead of winning, and I think he uses it as motivation. He's able to kind of turn the tables on certain narratives. And, you know, early on in his career, I was guilty of saying, you know, what, if you get this guy into a tough match, you know, he retired against me one time in Australia because of the heat and kind of had the reputation for for pulling the ripcord a little bit early. And I never would have bet my entire life that he would be one of the guys that you look at. And, you know, earlier this year, he took off his legs out from him, at Roland Garros at his home court. And he's become the guy, the guy that comes back from two sets to love down later on that French Open and, and play six hour matches and is able to recover. He really took that point of criticism, which I still think is accurate, and turns it on its head changed his diet changed everything about it, he's able to kind of take these little points of criticism, which I actually do believe he's sensitive about, but then turn them into strengths. And I wouldn't have bet you know, the he would have had this career and it's hard to actually make a statistical argument against him being the greatest now with the numbers that he's putting up. You know, a lot of the people that make an argument for Roger refer as it stands currently, it's not finished, you know, they're they're all still playing, but it's because Oh, I like their style better. I'm like, well, that's a preference that doesn't that doesn't equate to numbers. And so Novak has has gone far above anything I thought was possible. He's He's amazing to watch.

David Novak 12:45 

Well, who do you think is gonna win this year's? This year's Open? Who's your pick? I

Andy Roddick 12:49 

don't know that I would pick against Novak on any court in any situation right now. You know, as proven by that match against you get the Rafo at his home court, and then take care of business to win the friendship and to complete the career slammys Now I've done it twice. Which, which Robin? Roger roger haven't done so I think he's my favorite against any human on the planet anytime, anywhere right now.

David Novak 13:12 

You know, after Pete Sampras retired, you carry the torch for us tennis for a long time. And you said that America's men's tennis was your biggest responsibility. Explain?

Andy Roddick 13:26 

Well, I had a, you know, I was a fan way before I was a player of any note. And, you know, I thought it, you know, I knew it probably wasn't possible, based on my ability. And based on the track record of the guys that came before me. I knew it probably wasn't possible to live up to those expectations. But it was my responsibility to keep you know, American tennis fans engaged. I knew that I could, I could sell out a session. You know, if we're in Indianapolis, I need to do everything possible to make sure that we had you know, butts in the stands that they had a good time take care of my responsibilities afterwards. So what I what I couldn't match with talent mobility of the guys that came before me and us tennis, I knew I had to try to make up for it and other ways. And I was aware of that. And, you know, I think that's probably what I was referring to as far as a responsibility. You retired

David Novak 14:13 

literally on your 30th birthday. And believe it or not, I used to be a huge tennis fan love to play myself, for I turned the golf, you know, but like the rest of the tennis world, you know, I was shocked. I said, How could you be doing this to his van we'd love written for you why surely?

Andy Roddick 14:32 

The answer is I don't know. I I literally the day that I retired, I think I held a press conference around four or five in the evening. I decided that morning. And that was I just won my first round of the US Open the day before and I woke up and I was just I was analytic questions. My arm was hurting. You know, why are you doing this? Do you still believe and this is probably the biggest one Do you still believe with the state of your shoulder health How unbelievable every No one else is, do you still believe you can get through these three guys, best of five over the course of two weeks. And I think if I was honest with myself, I'm not sure if I believe that. So I didn't want to risk it feeling like work for the first time in my life. And I had other things that I was certainly interested in. I was a pretty selfish person when I was playing, and I kind of had to be. But I think I wanted to be a better husband, I think, you know, I wanted to spend more time on the foundation, there were certainly business interests that I was already involved in and other things that I was certainly interested in. So I think it was all of those things. But I decided in a course of about two hours with a conversation with about five people that morning, and then retired that afternoon.

David Novak 15:47 

Well, so let's, let's shift gears, and let's talk about what you're doing in some of your other venues today. Tell us about the Andy Roddick Foundation and and why and and when you started it,

Andy Roddick 15:58 

I started a version of it. I actually one of my idols, you know, the coolest thing is when your idols live up to the expectations that you have for them. And that was the case with with Andre Agassi. I used to kind of bumble around with him. And if he needed someone to play, you know, if he had a date to play an exhibition in Houston and needed someone to beat up on he would fly me in when I was 17 years old. And but the best part about that, for me wasn't getting beat up on but it was the travel time in between, right. So if we had to go from Houston to Louisiana that night, I had, you know, an hour with Andre where I could kind of drill down and, and ask all the questions. And one time we were on that we were on a plane and I asked him what his biggest regret was. And that's a loaded question with Andre, because he's been very upfront about, you know, his struggles throughout his career. And his, his book is probably one of the best, most honest accounting of, you know, kind of an iconic athlete that I've been I've ever read. But he said he didn't start his foundation early enough. And that was good enough for me. So we did our first event in a parking lot with a net in it. And I think we raised a couple 1000 bucks. And that felt good. And now fast forward to the current version of it, where we serve close to 80,000 kids a year through our direct service programs in our our lat network, which would be I guess, in business, it would you would have acquired, you know, 29 other different properties that focused on the out of school time space. So we are we are a leader in Central Texas. And you know, we were named the best out of school time program in the country a couple of years ago, just in time to have to shift gears with not being able to be with our kids in person. So it's been it's been amazing. There have been many, many, many people who have given their time and efforts to let us fundraise, because the belief in an idea and it's been, it's probably been the best part of of my life so far. Oh,

David Novak 17:49 

good for you. I think that's fantastic. And we talked about Sweden's code. Tell us about your other business interests and the process that you've used to decide what you're going to focus on?

Andy Roddick 18:01 

Yeah, so the basis for all of it was our I have a commercial real estate business that I started in 2008 Basically, the world was turned upside down. I was lucky enough to be sitting on some liquidity for my tennis career. And everyone was kind of anxious for for liquid cash there were deals to be had. So we basically just bought what we thought were quality buildings started off started off mostly in bank buildings and have since kind of pivoted to you know, Starbucks, Lowe's Home Depot's, you know, in 12 Different states, and it's the most boring business, it would bore you to tears, David, it's, it's so you buy quality buildings, you sign long term leases, you know, cap rates of five to 7%, you can borrow up against 2%, and you play the middle and hope that your buildings go up over time. So that's probably the basis for everything. And then I've, you know, luckily as, as I've met, smart people throughout the years, I've gotten to learn about you know, different things. So on the angel side, I've been pretty, pretty aggressive since since I retired, and, you know, lucky enough to have a couple of hits, but you know, I kind of always follow the motto, my, my dad from his farm outside of Platteville. He said, If you surround yourself with smart people and ask a lot of questions, you'll you'll be alright.

David Novak 19:20 

Now speaking of asking a lot of questions, you know, you moved from tennis, you get into business, even if you ever had any anxiety or or just issues yourself in terms of really dealing with, you know, having the courage to ask the questions that you need to ask to get to

Andy Roddick 19:35 

know I certainly I certainly feel like I live through impostor syndrome daily, you know, so, but I think, you know, you know what, I think Humans inherently have this built in thing where they they want to help as long as it's presented the right way and they know that someone's being earnest. I can tell you, you know, you gauge the room you don't, you know, fire off questions. Within 10 seconds of meeting someone, but if the relationship is is there, I think people appreciate it. And I guarantee it every person that I've asked a question to have someone, give them advice had mentorship on their way as well. So I yeah, I think at first, and I think that's a big, big value for people that aren't necessarily trained or from the business world is always asked, and if there's something you don't understand, you know, if someone's speaking a different language, because they're really good at whatever they do, and they speak in kind of slang terms, don't be scared to just say, Stop, what does that mean? You know, you can you can ask once and look dumb, or you can kind of be done every time. It's said, from there on out.

David Novak 20:41 

That's good point. You know, what you learn end playing tennis at such a high level that you bring into the business world,

Andy Roddick 20:49 

that I shouldn't have the same temperament.

David Novak 20:54 

You get a break and racket everyday.

Andy Roddick 20:57 

A little a little too often. I don't think there's there's a substitute for actually putting in the time. You know, you couldn't lie to the tennis ball, it knew whether or not you've been putting in the hours. And I think, conversely, if I'm going into a meeting, and I'm unprepared, I think that's very obvious. So I think preparation is key no matter what you kind of what world you're you're in. And preparation is largely a choice also. So I was certainly aware of that in tennis. So I always have this thing whenever I'm talking to young tennis players, but I think it applies to business, there's, there's gonna be things that are out of your control. But if you get 100% of the decisions, right, that are well within your control, you'll be fun.

David Novak 21:38 

You know, a lot of leaders go through struggles, whether they have what it takes to perform at the highest levels. Did you ever wonder about that? In tennis, which you are obviously great at? I mean, did you ever have any issues? You know, working through that?

Andy Roddick 21:52 

Oh, sure. I had, you know, my biggest point of jealousy with, you know, someone like a Sampras, who I used to watch and was a hitting partner for him and Davis Cup team, or Roger was I had to, I felt this I had this insecurity where I felt like I had to, on a back court, you know, tucked away at a venue somewhere, practicing the day before the tournament started, I felt like I had to play well, all the time. In order, you know, I couldn't play terribly on a Sunday leading into a tournament, and then just know that I was going to play well, on Monday, sometimes it happened. But I didn't have that kind of gift of of confidence. You know, then I finished like a two hour Grind Session where I'm beating myself up and it's probably why I retired at 30. Also in Roger Stone going but then I would kind of walk past Roger and you know, he's losing six to to some guy rank 500 in the world, all the while knowing he was going to be just fine on Monday. So it wasn't the Wimbledon finals. It wasn't, you know, the other tournaments, the lopsided nature of of our professional relationship. It was how easy it was for him day to day just knowing that it was going to be there when he needed it,

David Novak 22:58 

you know, and he one of my mentors, as was the late John Weinberg, who had at Goldman Sachs. And he said that was success either grow, or you swell. And you became number one in tennis at the age of 20. And, and even now, okay, I mean, you're unbelievable business person, starting new new brands, you know, you're married to supermodel you know, you got two beautiful kids, you know, how success really affecting you? And do you ever have to kick yourself in the ass to not get a little bit too cocky?

Andy Roddick 23:33 

know, if you're, if you're cocky enough, that just means you're not, you know, surrounding yourself with the right people, I don't think I don't think you need people nodding their heads on with whatever you say. And I probably don't need to tell you, our children are five and three. So if I'm ever feeling, you know, a little too proud, you know, I looked down and realized I get dominated by something that's two feet tall. So you know, it also like anything, any, any, any success that I've had, there's, there's a million people out there that have have have done more with less opportunity. So you know, it's always I think being being proud is fine. I think being aware is important also.

David Novak 24:14 

Absolutely. You know, and, and you were top 10 In tennis, nine straight years, you know, what do you think? As you look back at that and what you're trying to do today, what do you think is the key to sustain success for for that kind of leadership?

Andy Roddick 24:31 

You know, in my mind, I think that my best quality as a tennis player was getting up off the mat the next day, right? If if I took it on the chin, you know, that sucks, you know, and I kind of failed famously on on some big stages, but I'll be damned if I wasn't gonna be out there two days later, getting in my reps again. You know, maybe that wasn't healthy, maybe maybe their process should have taken a little longer but I do think there was something to having pride in getting Back to work. I was I was pretty good at that, that that's probably largely where the top 10 stuff came from

David Novak 25:13 

you know, common wisdom today is that leaders should play to your strengths. How do you think about managing strengths and weaknesses?

Andy Roddick 25:20 

That's it's such a good question. In I don't know, I think, I think what you know, is important, I think what you don't know, is probably more important. I've, unfortunately, I've seen a lot of people who have had success and in a phase their life, and they maybe feel as if, because of that, they can be experts at anything without actually putting the time into to learn and kind of go back to the drawing board. And, and, and be humble again, you know, so I, in my tennis career, I knew my server is going to be there, I knew I didn't have to spend as much time on it. I knew, it's like the one control mechanism that I knew if I put time in and kept my shoulder healthy, it was going to be there. So in tennis, I had to fill fill the holes a little bit more, I had to work on movement, my backhand was I still can't have a talisman back. And so, you know, so I knew that I had to plug those gaps in, I was able to maybe take less attention away from my serve. But in business, I think it's the other way. You know, I think they're definitive strengths. But, you know, I need to reach out and leverage contacts and ask questions. When I don't know, I actually think, you know, at a certain point, I probably play to my strengths a little bit more and spend more time on them.

David Novak 26:35 

We all face competition. How do you go about preparing to take on the best of the best, which you did? Many, many times?

Andy Roddick 26:43 

Yeah. I don't know. I'd love to come up with some huge answer here. You it's, for me, it was just a matter of being consistent with the work. You know, a lot of people will I saw a million players, they say I've been, I've been working so hard for two months, and then lose first round, they like See, I told you that hard works. Nothing. I'm like, you always have to be ready, even if the moments not ready for you. And a lot of times it wasn't ready for me. But sometimes it was in so it was less about like, kind of building towards one thing or kind of over overvaluing one result one way or the other and really being consistent and being ready. You know, for the moment.

David Novak 27:20 

When did you realize Andy that Federer was superhuman?

Andy Roddick 27:24 

Early? Very, very, it wasn't it wasn't really much of a secret. You know, I've never seen someone who's kind of one, two or three slams be viewed the way that he was that that early. I remember there was a there was a it wasn't a sports century thing that I did. And I remember Cliff Drysdale commented on it. And he was there. I think Roger had one. Two slams at that point. And he goes Roger Federer, he goes, he might be the best I've ever seen. And you don't really say that about someone who's won two slams or two majors. And so I think it was pretty apparent very early that he was he was a little bit of different gravy.

David Novak 28:04 

And uh, you are well known for saving countless match points. And you even played the longest match in history 77 games versus Federer at Wimbledon reborn with this mental toughness, or did you actually work on it?

Andy Roddick 28:20 

No, I think it was just trying to get through one point. Try not to vomit before the next one, and then just be on with it. And I just repeated that for about 13 or 14 years.

David Novak 28:29 

Well, how do you not vomit? I mean, seriously, you how do you not vomit? What did you do? Did you have anything that you did that you that made you tough?

Andy Roddick 28:40 

So again, I can't give enough credit to preparation but actually being in the moment I was, I was big into rituals. So I used to get made fun of the locker because I'd always go to the towel, I would do a thing I kind of would repeat the same process. And for me, it was it was a nice reset, you know, you do something great crowd goes crazy. Maybe you react and then there's that moment of like, reset, okay, back in the moment. And I think kind of having that reset button, whether it's, you know, in business and you have some ritual to kind of take it down a notch or reset to go back up. I think that's actually super, super important. You know, I think there's value and letting the mind play tricks on itself sometimes.

David Novak 29:21 

Now, you had a number of tennis coaches in your career. Looking back, who do you think was the best and why?

Andy Roddick 29:27 

Gosh, there's there. Okay, one I'll say like I was lucky enough to, to sort of kind of pick the brains of some absolute legends. Brad Gilbert was, was amazing. from a tactical standpoint, the way he saw the game and the way he was able to kind of analyze and very kind of basic terms, made everything very simple. And when I was young, I probably needed that a little bit. Obviously, Jimmy Connors was my coach for a couple of years and you know, Uh, Jimmy could tell me the same things as other people. But like, it's Jimmy Connors. And when he looks at you and says something, you feel like your soul is glowing, right? Like he feels like it just, it's just heavier and, you know, to be able to work on footwork and what I needed at that point in my life and improve a backhand and how he was kind of motivated again, and we actually did a podcast last year and I, I said, I got a lot of joy out of bringing you back to the game and having you kind of compete in a different way. And, you know, he kind of said, you know, some of those without doubt, that made me very happy. Larry's to think he was amazing. He's, you know, probably the most, you know, under the radar coach, he's coached for number one players, you know, and he was what he was amazing at was a lot of guys. A lot of coaches coach a certain way or a certain type of player. You know, someone used to come to the net a bunch, so they'd like, you know, Sampras and Roger and the people with certain toolset, you know, Larry has coached, you know, a five foot nine Chilean guy who got to the number one who's a lefty, who stays back and Marcelo Rios, Johnny Mack, who's obviously insane. me who's not much better. Fernando Gonzalez, another Chilean, but a big Husky guy, you know, so you're getting Kafelnikov Crazy Russian, you know, so he has an unbelievable ability to see the kind of strategy through your eyes as opposed to what makes him comfortable. And I think that that takes a special kind of talent to kind of get out outside of themselves. If that means being more effective as a as a coach,

David Novak 31:34 

how you coach people. Now, what's a one on one coaching session? Like, oh, gosh,

Andy Roddick 31:38 

I don't I don't really coach at all. I have some players that come through. And I think it's less to do with with technique or anything else, I think you'll see a lot of young players when they're making that jump from juniors or you know, I guess in golf, what would be, you know, the web tour into kind of the pro tour. I think there's, you know, an unnecessary thing where you hyper analyze everything, right? Like, oh, gosh, these guys are so great. I'm like, No, you're sir, you're serving 128 to, you can run as fast as they can, you're in your own head, you're trying to play too well, let's calm it down. And let's simplify, let's, let's, let's, let's, let's get three great things out of this session. So I think the ability to kind of have someone who may have played at a certain level, just kind of calm everything down, take it simple, do the work, do your stretching, put good things in your body, make sure you get your sleep, let's take it down to a base level. If I if I have a kid or an aspiring Pro, for two or three days, I think just kind of those mechanisms that maybe they can take forward, where they're not just typing out about everything is probably how I can be beneficial and kind of a short sample size.

David Novak 32:47 

Your life is obviously been incredible. If you literally became a pop icon. You appeared on Letterman, Leno, Ellen shows, you know, how would you describe the the end Andy Roddick brand, and how are you evolving,

Andy Roddick 33:04 

I don't try to evolve it. It's weird, because that was that was all pretty front loaded. And we talked about my responsibility to the game of tennis, but also I knew I had to do a lot of that stuff, because you know, contracts expire a certain place. So the first five or six years of my career, I was pretty ambitious with with, you know, in pretty calculated with what I wanted to do. And now it's kind of next to nothing. You know, I do a little bit of Tennis Channel from from our house, but a lot of the stuff I do now isn't isn't really isn't real front facing because it doesn't have to be if there's a way to add value, you know, by kind of getting out in front of things, and I certainly am happy to do that. But it's certainly not something I seek out daily. How did

David Novak 33:47 

you think about endorsements? And who you hooked up with? Yeah,

Andy Roddick 33:53 

a lot of it was you know, obviously, there's a big financial element of it. But yeah, I wasn't real good at, at selling a product that I didn't really believe in, I never really had and, you know, if I want to be able to use it, if I was going to endorse it, I wanted to be a fan of it. I wanted to you know, I think people can can sometimes tell us if people are genuine or not, I felt like I was you know, genuine for better or worse. A lot of times it was worse in press and stuff but I wanted to obviously a good partner I wanted to be very, very clear about my responsibilities and the answer honestly, if I thought that I could do them without interfering with with with tennis, and kind of that sort of focus because it all falls apart if you don't kind of keep that that block in place. And then if I was actually a fan and a user of the product or could be

David Novak 34:46 

great you know, you developed a lot of wealth at an early age and and you're known for managing your money well investing your wealth and in real strong fashion. What advice do you offer others on this front? Start early. And

Andy Roddick 35:00 

the biggest thing I hear when I'm when I'm talking to now my my friends have gotten a little bit older, but it's like, well, it's easy for you because you, you, you know, you were lucky enough to have and so that's fine. But like on a pro rated version, if I'm investing 2%, it's kind of there's still a drawdown, there's still a number that you need to be strategic with monthly. It's not just like on a whim, I'm going to invest in this, like it needs to be consistent. And disciplined over time, I was lucky enough to be taught that by by my business mentor very, very early, but the thought that I can't do it just because I don't, there's a prorated version, and it's, you know, of what you can do and, and starting early is one of the biggest factors and it's, it's, it's certainly changed a lot for me.

David Novak 35:43 

You know, Andy, you're known for having a wicked sense of humor. And you even told Letterman that your booming surf was was your go to just like his top 10 letter? List. I love that top 10 list. And I loved watching some of the stuff that you did on YouTube. It's great, you know, how do you how do you think about your humor?

Andy Roddick 36:01 

I don't I don't. I think it's it's funny. I think, in a lot of apps, I got actually got to ask about this. When I worked at Fox Sports for a couple years, when they started this fox sports, one network. And we had this roundtable and it's like, well, you know, you were so outspoken. You know, in a lot of that they were basically the top of the conversation was do athletes ever really tell us anything? They have to be protected? I said, Yeah, but that's not fair. Because, like, if I said something, and it was, you know, polarizing or funny or not funny, or someone want to get mad at me about it, I actually only had to account for me, whereas you get someone who's the leader of an actual team. You know, let's take someone who's been on your podcast, Tom Brady says something 70 Guys in his locker room have to answer for what he said. And that would modify me. So I think I had the ability to be outspoken because I kind of had ownership over what the what the scar tissue would be from, from whatever I said, and frankly, I think a lot of times people mistook made the mistake of taking honesty as humor, you know, I was kind of just tried to answer straight away in a straightforward fashion. If you did

David Novak 37:11 

you know what good any leader learn from hosting Saturday Night Live like you did? Gosh,

Andy Roddick 37:19 

when you suck at the rehearsal right before the actual show, go to the corner store and get a couple of beers and then go do your monologue. More truth? Yeah, exactly. And that's absolutely what happened? Um, I don't know, I think there's, I think there's value in putting yourself in uncomfortable positions, you know, going there and having the writers in that room and, and, you know, seeing the talent and not trying to kind of control it too much. But putting yourself out there listen, I, I do well, I do horribly. I think there's value that you can pull from, from that experience. And I was certainly never, never scared to kind of get outside of my comfort zone. But that SNL is intimidating. I'll tell you that. That is it's a pretty scary thing.

David Novak 38:05 

You're definitely out of your comfort zone for sure. That way. You know, obviously today with everything that's going on, and every leader is focused on diversity and social justice. How do you think about it? And how do you think tennis has created social change over the years? Well,

Andy Roddick 38:23 

listen, I I think if there was there were icons, as far as what would be a Mount Rushmore from, from sports, you know, we would have a lot of the players in that conversation from, you know, Billie Jean King, and what she did for a quality of, of the economy and the tennis economy and, you know, Arthur Ashe, and what he stood for, and someone that doesn't get talked about enough for her decision making in the 80s was Martina Navratilova, which, you know, at that time to one defect from, from Czech, and then to come out before it was it was even a common narrative was unbelievably brave, and she doesn't get talked about enough but then you, you pay it forward to what Andre has done. You look at what Roger has done with being you know, a lead UNICEF ambassador for a long time and then building his own schools and the I always say that I was very lucky to get caught in the in the right vacuum. You know, tennis has always stood for it. I feel like they've been been leaders in sports for equality. So I feel I feel lucky to come from that universe.

David Novak 39:36 

You know, Andy, you chose not to defend your Dubai title. And it was it was $2 million in prize money. You said you're not going to play tell us why. Well, there

Andy Roddick 39:46 

was there was conflict at the time. You know this with with Israel and there was a female player named Shahab here, who wasn't allowed to go compete and I just thought that was pretty unfair, I think I think sports should be something that's that's unifying. I think there's there's value in, you know, I was friends from with people from all across the world, differing views on a lot of topics. But there's still ability to find common ground. And I kind of felt strongly about that I didn't feel good about going there. And benefiting from a tournament that was making a decision that I largely disagreed with. You know, I didn't know, Shahar at the time. It's not as if I was, you know, backing up. A friend of mine, it just seemed like it was the right thing to do. And, frankly, the attention I got was was a little embarrassing. I don't think that's why I did it, either. That was before Twitter where you could kind of, you know, grandstand with the the press of a button. You know, so, I don't know, I just, I just it didn't feel right to me.

David Novak 40:51 

And speaking and finding common ground. You know, I saw somewhere that a player at one point criticized you to the press after a match. And you supposedly called him afterwards and challenged him on it, you know, so many people are afraid of productive conflict. I mean, it was, is that something that you find easy to do? Or did you do that? Is that a true story?

Andy Roddick 41:15 

It was it was a it was actually someone I'm friendly with now, is Rogers coach Yvonne Lubitsch. And, you know, and listen, I'm not going to pretend like I wasn't, I wasn't going to run, rub people the wrong way, with with the way I went about my business on court. At the US Open, I was going to use the crowd to my advantage. There were there was no doubt about that. And, you know, he went in and said some things that I thought were, were an assumption, you know, maybe would have been better served to have that conversation behind closed doors first. You know, it's certainly his prerogative, but I just kind of want to make it known that it wasn't appreciated, I wasn't going to respond in time. But that didn't mean that I wasn't pretty pissed about it. You know, so. And we, I think it's easier to kind of, you know, maybe have that conversation, eventually the dust settles, and maybe there's a level of respect for having had that conversation. And then, you know, we were fine. Yeah, we were, we were friendly later on. So, I don't know if it was because of that. But, you know, I certainly felt like, I would like to hear it directly from him. And, you know, you know, and a lot of times what's portrayed to me, you know, they, you know, they wanted that conflict. So I just wanted to make sure I was fully understanding of what was said, and what was meant, well, a lot of

David Novak 42:29 

people avoid that kind of conflict and trying to, you know, get to get to a level playing field again. So, it's not easy to do. Yeah, and, you know, and you, you, you have a huge social following. In fact, we actually exchanged some direct messages over Twitter. That's how we started to get to know each other. And I understand that you actually applied for a job over Twitter during it, tell us about it.

Andy Roddick 42:53 

Well, you know, early, early days of COVID, I'm watching, I'm watching tennis channel, and I don't do any, any sort of commentary I didn't. Because I kind of promised myself that I didn't want anything to completely control my geography again. So, you know, going and commentating Wimbledon isn't an option, if you're not willing to travel for two weeks at a time during the summer. So that's kind of where it has always been. But there was certainly an opportunity when I was, you know, watching reruns on Tennis Channel, and they were doing, you know, top 50 lists and top 100 lists, and I was like, I could, I could do this. So I kind of just threw it out there. And, you know, I'm still kind of working on on a, on a very casual basis for both sides. And it's been fun. You know, there were there was so much negative that came from, from the last year and a half, but one of the positives was kind of reigniting a love affair with with tennis and being able to kind of mix it up and talk about it. And you know, what you're seeing behind me is the exact same setup I have on tennis channel, so I get to do it from my office. So it's kind of a perfect scenario that came from you know, kind of shooting a random shot on on a social medium.

David Novak 43:59 

Nothing ventured, nothing gained. Right, you know, you know, I understand that slipped into a little more serious note here that you actually saved a lot of people or some people in a in a hotel fire. Tell us about it. And when did that brush with? Get teach you?

Andy Roddick 44:16 

Yeah, yeah. It's it's weird to talk about you don't want to you know, it's it's, it's not something to celebrate. There were we were in it was in Rome in 2004. I had gotten there the night before, and I woke up I think it was like four or five in the morning. And there was a lot of smoke and and haze and I could smell it before I saw it. And so I wasn't sure what it was I'm like, is there something electrical going on? Is there some sort of you don't you don't go to like your mind doesn't go to instantly to like the hotels on fire. So I opened the front door to kind of I was gonna walk to the lobby or just get out or just kind of see what the deal was and just a plume of black smoke came in so that's concerning. And so I closed the door. put like a wet towel underneath it just so it wouldn't come in. And then I walked out and I had a patio. And where I was staying, I was on the sixth floor, the seventh floor was a half floor. So the firetruck ladders couldn't get to the seventh floor without kind of overshooting. So the people on the seventh floor would basically stuck so we basically just Jimmy wrecked an operation with couches and different things where they could jump from the roof on the seventh floor down to the sixth floor where I was you know, there's some luckily it was there's a group that spoke English it was a tourist group from from Minnesota, but then we were able to kind of get them to where the the fire ladder could reach unfortunately, people died from from that floor. And so it was a it was a pretty traumatic experience. I went back to get my stuff later that day and it's all just covered under about an inch of set. And so it was it was it was pretty intense it was it was very unfortunate. It but it's in a strange way it's we come from these worlds where we have a lot of acquaintances and you don't know how deep those go and tennis is you think it's like that and then something like that happens and by the time that I got down I was I think I was the last one down out of the hotel I'm getting goosebumps thinking about it but all of the players who were there knew that I wasn't down yet and all this stuff and so it's just you become a family very quick even players you've never talked to before you again you share that common ground and while everyone was was certainly devastated it was it was a humbling moment to see the the amount of care that people had I can

David Novak 46:34 

only imagine you know Andy you know it the row Masters on a critical match point. The lines been called your opponent's serve out but you knew it was in and you showed the umpire the clay mark that hadn't reversed the call and you end up losing the match as I understand it. Why did you do that? What is what in it? What's in you that made you do that? A lot of people just say hey, they missed it that's the way it goes that sport

Andy Roddick 47:03 

Yeah, I this one gets celebrated more than it should to it that it was the wrong Mark I think the umpire would have figured it out. Eventually when they came to look at it there was a pretty obvious Mark I truthfully I thought I was still going to win there we go. But But I didn't and so you know it would have been a it would have been a something that no one ever talked about again had I actually won the match I think I think that I think the fact that I choked like a dog and lost an hour later probably added more to that story.

David Novak 47:44 

Oh my god this has been so much fun for being and I want to have some more with the lightning round of q&a Well okay. All right. What three words best describe you

Andy Roddick 47:54 

she's kind I think fair and impatient.

David Novak 48:01 

What's something about you that few people would know?

Andy Roddick 48:05 

That I'm probably a lot nicer away from the court the way they know me I don't really act the same away from the court that I do on the court.

David Novak 48:15 

Your biggest pet peeve

Andy Roddick 48:19 

people who are kind of unaware right if if four people are trying to get like through a door or something and someone standing in the door having a conversation with a friend I just think like the inconsiderate nature of stuff like that drives me insane like it just did the kind of being unaware you know, leaving your car somewhere blocking someone and stuff like that drives me absolutely nuts.

David Novak 48:40 

Do you have any hidden talents?

Andy Roddick 48:42 

I have zero talents

David Novak 48:47 

your favorite song of your pal John Legend.

Andy Roddick 48:50 

Oh gosh. Let's see. All of me is obviously the all of me. I know what's his most famous one. I like it just because it's about Christie and we know her and it was it's my favorite one for him because it you know, he was already an Award Grammy Award winning on it, but it kind of launched them into into a different stratosphere. So I think for it's probably not my favorite song like personally, but it's my favorite song overall, just because, you know, it'll be the one that's played at a wedding. 30 years from now.

David Novak 49:23 

Favorite sport besides tennis and your biggest accomplishment in it.

Andy Roddick 49:28 

Oh gosh, I love golf. We know that. I think we have a lot of common friends in the golf world, but I don't have many accomplishments. I've played the I played the Pebble Beach Pro and three times I haven't made a cut. I'm not sure I've won a member guest ever so it's still searching.

David Novak 49:48 

I'm the leader you admire most?

Andy Roddick 49:50 

Oh gosh. That's a huge question, isn't it? Anyone who's who's done something that they thought was right but for or that wasn't easy to do. So I think of whether or not you, you know, agree with why these people did things, but the fact that they were able to kind of give up something for themselves to do it. So you look like at a Nelson Mandela, you look at, at at a Muhammad Ali, you look at people that did the hard thing, because they thought it was right at at a certain level of self sacrifice, right? If you make a stand and you have everything to gain from that stand, it's great. When you have everything to lose from that stand, I think it's probably even more impressive,

David Novak 50:28 

you know, based on what you're doing today and what you've observed. You know, what three bits of advice would you give to aspiring leaders?

Andy Roddick 50:38 

Communicate? I have a friend of mine, who is company notes, he always writes sit on the floor, if all the chairs are taken, sit on the floor and have a smile. And I always I always think that one and then we already covered it. But don't be scared to ask questions. That's, that's those are the probably the three biggest things.

David Novak 50:57 

I love to sit on the floor. That is a great way. You know, it's one of the reasons why I love doing these podcasts is picking up little tidbits like that. That's fantastic. You know, last but not least, tell us how you balance all you have going on with your wife, Brooklyn, your two kids, you got a lot of things, you know a lot of different things, you're investing in starting new brands, etc. How do you balance it all? What's your what's your guideposts

Andy Roddick 51:22 

organizing as far as schedule helps, you know, using the calendar your to your advantage? You know, I know if I'm in a certain city and I can get two days of work done, I would much rather stack those days. Full every Monday I clear out my inbox. That's that's, that's a big one that keeps you from kind of procrastinate, you get into a little bit of a routine and be available. call people back when they call be accountable. But do it on your time. You know, I after 730 At night, if you need to talk to me that badly. That's when I can talk because my kids are down. So kind of having having boundaries but still in the realm of availability I think is important.

David Novak 51:59 

Is there any question that I haven't asked you that you wish I would ask?

Andy Roddick 52:05 

I don't know. That's, that's That's your job. I feel the back of my knees are sweating with some of them. So I don't think

David Novak 52:13 

you're a podcaster yourself. So maybe I might have missed one though. I

Andy Roddick 52:16 

think you were very thorough and well researched.

David Novak 52:21 

It was obviously a lot of fun. And Andy, I want to thank you so much for for taking the time to have this conversation. And it's been great to get to know you and I look forward to teeing it up with you. I like to play people who say they never win. I'm not sure I believe it. But you know, it'd be nice to I'd like to win sometime myself.

Andy Roddick 52:41 

I'm your guy. I'm your guy that no problem.

David Novak 52:45 

Great. Thanks so much.

Andy Roddick 52:46 

I appreciate I love what you're doing. I'm a listener. And this is an important conversation about leading, I appreciate you.

David Novak 52:59 

That was so much fun for me, because I'm such a big Andy Roddick fan, on the court and off. And I'm a bigger fan after this conversation. I'm so impressed with his honesty and his hard work and how he has been so fearless about his retirement to jump into the world of business. And your journey as a leader, you're going to find yourself in unfamiliar territory to you're going to feel uncomfortable or uneducated or just outside your field of expertise. In those moments, we can't be afraid to ask questions, even if we think it'll make us look dumb. So let me coach you a bit and help you apply this insight from Andy into your life as a leader. This week as part of your weekly personal development plan, I want you to look for an opportunity to ask questions, you don't know the answer to put yourself in an unfamiliar situation. It might be an area of your business, you've always been a little bit intimidated by or new area you could expand into but you don't know enough about it yet. Or hack something completely different that's always intrigued you even though you know jack squat about it. Whatever it is, you got my permission to go out and ask a bunch of questions about it. Of course, like Andy, you've also got to prepare so that you ask the right questions. And you've also got to respect the time and relationship of the people you ask. But go out there and fearlessly ask questions you don't know the answer to. You're gonna find a whole lot of cool opportunities waiting for you when you do. So do you want to know how leaders lead what we learned today is the great leaders aren't afraid to ask questions. Thanks again for tuning in to another episode of how leaders lead where every Thursday you get to listen in while I interview some of the very best leaders in the world. I make it a point to give you something simple on each episode that you can apply to your business so that you will become the best leader you can be