Confidence Classic: Chase Failure, Build Courage, and Go After What Scares You with Ryan Leak

0:00Way too often we pre-calculate failure and this abort mission all together. We literally talk ourselves out of our own dreams every single day. They're predicting, according to my assessment, I will fail. Therefore, I won't even try. You can't sell a book that you don't write. You can't get people to listen to a podcast you won't record. Even this morning, it was like, hey, are you going to do a book tour? I'm like, well, what if I go to a Barnes and Noble in New York and nobody shows up? No, like you got to put yourself out there. I think the difference between people who are successful and people who don't get all that they want from their life is that successful people were willing to go sit in the bookstore and be by themselves.

0:38I'm on this journey with me. Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. I'm ready for my close-up. Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to. So these bonuses are a great way to help you find the ones you may have already missed. I hope you love this one as much as I do. Hi, and welcome back. I'm so excited for you to meet my guest today. Ryan Leak is an executive coach, bestselling author and motivational speaker that gets to inspire over 50 ,000 people every month and train over 20 ,000 leaders every year.

1:24He's widely known for two documentaries, The Surprise Wedding and Chasing Failure. Ryan is also the CEO of the Ryan Lee Group LLC that is a leadership development firm in Dallas, Texas. They have the privilege of working leaders and teams all over the world from NBA teams to Fortune 500 companies. Ryan, thank you so much for being here today. Yes, it is my privilege to be here with you. Okay, so I get a lot of DMs. You're an incredible speaker. And guys, just a little behind the scenes, a very good friend of both of ours, Jordan Montgomery, who you know was on the show earlier. If you haven't heard that episode, go back and check it out.

2:03Introduced us on text. And in typical fashion, I'm being sarcastic with people. I didn't even know Ryan. I didn't know who he was yet. And I'm saying, gosh, Ryan, you're not even active on this thread. You better be on the PST time zone because this is pretty lame of you. he hits live video on his camera and is literally about to take the stage in Atlanta for Chick-fil-A in front of thousands of people. And I was eating my words. So all I want to say is this man takes the biggest stages in the world and speaks more than anyone. So Ryan, so many people DM me all of the time asking, how do you get into speaking?

2:44How does a speaking career even materialize? And And I know we were talking about it a little bit off air, but can you give us that backstory on how you ended up where you are today? Yeah, for sure. You know, I grew up in the church and my dad was a pastor. I just thought my dad did a great job of just adding value to people's lives. And he got to he was so involved in the community. And I just was so mesmerized that people would come together every single Sunday and hear him talk. And I thought, man, what an awesome way to impact somebody's life. And you don't use stages to beat people up. I think you use stages to encourage people and build people up.

3:19And so I just kind of enjoyed it. And I just kind of had a knack for it. And I was pretty comfortable in front of people. And I just tried to work on my craft and just serve people and trying to add value as best I could. I started speaking at a bunch of churches around the country. One day, an executive from a, what was the name of that company? They were a credit union. They said, hey, will you come and just do our staff development day? And I was like, sure. And so I did. I'm a proponent of give your best to the opportunity that is in front of you. Not the opportunity you want in the future.

4:00No, the opportunity that's in front of you, you're given an opportunity to speak to 10 people. Go crush it with those 10 people. you will never crush it with 10 ,000 unless you crush it with what's in front of you so I just tried doing that every single week whatever opportunity I was given I just tried to give my very best to it I remember getting invited to to speak at a conference in Atlanta in the event planner say hey you got seven minutes and I felt disrespected by that I felt like seven minutes I'm flying all the way here just for seven minutes like really but then it was just like no dude give your best to seven minutes crush the seventh like this dude had never heard of you before and you have you have to kind of own that like some people it's like you're a household name in their household but then and their neighbor has no idea who you are and so you got to have I think a self-awareness in that and so I went and I just tried to to grand slam that seven minutes and And when I did, he called another friend who had me speak to 45 ,000 people six months later.

5:05He said, hey, I just had this guy speak. He did something in seven minutes I've never seen before in my life. And so I always encourage people, give your best to the opportunity that's in front of you. You never know who's watching. You never know who's in the crowd. You never know whose kid is in the crowd. You never know whose mom is in the crowd. I just consistently try to give my best in whatever room I'm in. It could be a boardroom. It could be an arena. It could be a church. It doesn't matter. I just try to give my best. And it's helped me build a pretty great career. There's a great Abraham Lincoln quote that I'm sure I'm going to botch, but it's something like this.

5:44Ask me to speak right now for one hour. I'll take the stage. Ask me to speak for 30 minutes. I need two days. Ask me to speak for anything under 10. I need months. It is so much more challenging to be incredibly concise and tight versus to get up and storytell. So that's really impressive that you were able to pull that off on the spot. I get asked to do all sorts of stuff. You know, I just, again, stay ready so you don't got to get ready. And I work with a lot of athletes right before games. And so you have a very short window of time to impact them and give them a thought that doesn't throw them off.

6:24but inspires them to play, but also gives them something to chew on about their life. And it's difficult, but I think it's a muscle that I've just tried to work on over the years. And I think the more you do it, the better you get at it. What are some of the things that you say to professional athletes before they're about to take the court at an NBA game? How do you encourage them or what words do you share? One of the things that I think is vitally important for a professional athlete, it could be a coach or a player, is got to have fun. Gotta have fun. Sometimes the check is so large, the media pressure, all of these talks around the sport, what it can do is actually suck the life out of what used to be how you got started was you went to a park where kids go and you have fun.

7:14now you're a businessman now you're a businesswoman now it's it's your job it's a career and sometimes the person that's paid the most has lost their passion for the sport so what i try to do is bring them perspective to say hey just so you know uh did you know you get paid to play a game tonight it's amazing like we can't lose sight of that and there's just times where I'm getting ready to speak where I'll say that to myself like did you get paid to talk today that's insane it's remarkable like do you know like there are people who work all year long to get paid what I could get paid to speak one time it is absolutely absurd but I just I always have to just step back and just go, man, we got to enjoy what we do because we can't take it for granted.

8:11We worked so hard to get where we are, but you can go to so many conventions, so many conferences and read so many books and listen to all these different podcasts on how to get success. There's not many resources that teach you how to enjoy it once you get it. And so I just, I love to tell an athlete right before a game, hey, enjoy the fact that you get paid to play a game that kids play in parks. Don't forget to have fun in the midst of all that is going on. And ESPN is not real life. Okay. Like your life is here right now. Enjoy it. And I just try and give them a little bit of perspective in that because I just remember even being an athlete myself or so many games I had, it was like the pressure of the world was on my shoulders.

8:57And I look back and I go, I didn't enjoy it enough. I love that you just shared that you were an athlete because that takes me into the best story that is really the foundation of chasing failure, which I would love your first book, Chasing Failure. How falling short sets you up for success. If you could get into that amazing. It's literally mind blowing. I still can't even believe you did it. It's so incredible. Yeah. So I played college basketball at B3 ish school. The ish is that it wasn't fully D3. Our D3 status was pending the years that I played there. And what we were in the NCCAA, which stands for National Christian Collegiate Athletics Association.

9:39So I like to tell people amongst Christians, I'm really good at basketball. Church League MVP is how I like to see myself. But I had never pursued the pros. Me and my wife, we went on the Queen Latifah show because of a surprise wedding, which is a whole nother thing. But my wife told her friends she thought it would be cool to get engaged and married on the same day. Had no idea what that meant. So I guessed, planned a wedding behind her back over the course of two years. That's a viral wedding story documentary on YouTube. Because of that, we got to go on the Queen Latifah show. On the Queen Latifah show, my wife and the Queen surprised me by getting me connected with the late, great Kobe Bryant.

10:19And Kobe comes on a video, says, hey, Ryan, heard about this fabulous wedding. that you had for your bride and just wanted to return the favor and invite you out to Staples Center to come hang out with me and the Lakers. I passed out on Cleveland Thief's couch and I had three months to prepare to meet Kobe. And I was thinking like, man, I've never actually like tried to really go for this professional basketball thing, but I've always like, I would go to games and I would be like, man, he should have went left, man. He should have went right. Like I always had this idea, like I could do their job better than they could.

10:53it but I'd never actually done anything about it and so in getting ready to meet Kobe I said I'm gonna get back in all American d3 is shape and I'm gonna go for it I started playing a friend of mine who had just got cut from the Chicago Bulls and he beat me every single time pretty easily I'm 6 '3 205 pounds he's 6 '5 about 245 so there was a pretty big gap between us and I was like man just forget this dude like you're you're not gonna make it in the league just go meet kobe take a picture like a normal person and just go home and i thought man that was pretty fast like you had a one percenter idea like being an emba and you gave up on it in like 24 hours that's like giving yourself a failing grade on a test you refuse to take like how do you know you're gonna fail unless you actually try way too often we pre-calculate failing and just abort mission all together we literally talk ourselves out of our own dreams every single day.

11:53And so this was a day where I said, I'm going to actually talk myself into it. And so I started asking people, you know, what would you do if you knew you couldn't fail? And so when I asked that question, it was like, well, hey, I'd be in the NBA. So I meet Kobe and I say, hey, I'm doing a documentary called Chasing Failure. I'm actually going to ask a lot of people, what would you do if you knew you couldn't fail? And I'm going to go for something that I think I'll probably fail, but there's only one way to find out. And that's for me to try. So I say, I'm going to be in the NBA. And he's like, yeah, do it.

12:19And I was just It's like, nah, dude, that's the wrong answer. You were supposed to tell me how hard it is. You were supposed to tell me about 4 a.m. workouts. You were supposed to tell me about the nutritionist. You were supposed to tell me about the politics of it. But no, he just stuck with the Nike slogan, just do it. And so I did not know how to get into the NBA. For people that don't understand how the NBA works, it's the National Basketball Association. It's not a church league. There's a protocol. You need to go to Duke, North Carolina, play overseas. You need to have an agent. You need to go to the combine.

12:50There's a protocol. They're not really looking for motivational speakers to join their team to boost the morale of the squad. Like, that's not a thing. So I did the thing we all do when we don't know what to do. I Googled it, and I found the public relations emails for every NBA team, and I just started emailing them one by one, saying, hey, you got a bunch of fans across the city that are afraid to fail. I don't think they should be. I think they should embrace failure. I think you should embrace this idea enough to let a complete stranger work out for your basketball team. I'll probably fail but what if I don't my name's Ryan Leak I'm 6 '3 205 pounds looking for failure and I had sinned it felt illegal I was like Ryan what are you doing this is crazy and then the Celtics throw me back and they're like hey this is a great story it's just not for us I was like that sucks man Ryan this idea is so bad they won't even let you fail at it like this is terrible like what are you thinking but then I thought did the Celtics just email you back like this is amazing.

13:44Like I'm going to make a documentary about being told no by all 30 NBA teams. This is going to be amazing. Like what can we learn from no? And so I always encourage people, you want to take notes on every single rejection because there's a lesson in there. So they weren't actually even giving me a rejection. They were actually giving me NBA language that I didn't have before. So I started changing my pitch every single email. Fifth email goes out to the Phoenix Suns. They're like, hey, we love this idea. Come on Monday. I was like, Monday? What? Are you serious they said yeah bring your camera crew i was like camera crew got no camera yeah yeah yeah you know like we'll we'll be there first thing monday board it so i called my homie chuck i said hey man let me hollish for a second we ain't talking a little bit we need to go to phoenix he's like what we're going to phoenix for i said don't ask questions just trust me it's gonna be awesome so i got a two-day workout with the phoenix suns and i made a whole documentary about it and it's called chasing failure spoiler alert I failed and so now I get to teach people all about all of the lessons that I learned from failing in Phoenix and at one point the drills are basically like hey you're gonna take 20 shots our guards make 18 out of 20 that's the NBA standard I was making like 15 or 16 out of 20 so again I'm good but they're great I fit in but that's the problem.

15:07NBA players don't fit in. They stand out. They're outstanding. They are absolutely remarkable. So I, at one point I'm looking down at the court, I got my head down. I'm feeling shame. I'm feeling embarrassed. Like, man, like you're not good enough. And I look down and I see this logo and it's the Phoenix Suns logo. And I asked myself, Ryan, how'd you get here? Because there's a lot of places you could be. And I realized chasing failure took me further than chasing success ever did. Because it got me way out of my comfort zone and landed me in an NBA practice court. I'd done a lot of things in my life up until that point, none of which landed me on an NBA practice court.

15:43And so now in hindsight, it's very interesting to think, number one, NBA teams don't give workouts to motivational speakers from convincing email. That's not how it works. But what I learned in Phoenix is sometimes they make an exception. And you'll never know if you're an exception unless you're willing. to send an email. The second thing that I've learned in hindsight from that whole experience, now that I get to work with about five different NBA teams is there's more than one way to be in the NBA. And I never, I would have never seen that or known that had I not been willing to, to go out there and say, Hey, look, let me, let me give it, let me give it a shot.

16:20So, so yeah, so that, that, that's the chasing failure story. That, that's what I try to help people get past some of their own barriers and try to help people get out of their own way. and so for you you no longer are stopped by fear is that correct oh i mean i deal with it all the time i just have to just as weird as it sounds glennon doyle says it this way if you can't beat the fear just do it scared so for me i'm just consistently doing a lot scared i just sign myself up for stuff that i can't do and i just like just go for it and if it flops it flops But I just kind of have that model of just like, hey, let's just let's just see what happens.

17:06And you won't know unless you decide to put yourself out there and try some stuff that you've never tried before.

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19:41Chime is not just smarter banking. It is the most rewarding way to bank. Join the millions who are already banking fee-free today. It just takes a few minutes to sign up. Head to chime.com slash confidence. That's chime.com slash confidence. Chime is a financial technology company, not a bank. Banking services, a secured Chime Visa credit card and my pay line of credit provided by the bank or bank na or stride bank na my pay eligibility requirements apply and credit limit ranges 20 to 500 optional services and products may have fees or charges see chime.com slash fees info advertised annual percentage yield with chime plus status only otherwise 1.00 % apy applies no min balance required chime card on time payment history may have a positive impact on your credit score results may vary see chime.com for details and applicable terms were you fearful writing the first book chasing failure oh my gosh so So in Chasing Failure, I tell a story about the first version of Chasing Failure.

20:37The Chasing Failure that's out with Thomas Nelson now, nicely buttoned up and whatnot, is the fifth version of Chasing Failure. So the first version, I self-published. It was like 60 pages. It was essentially the same story. Somebody watched the documentary. It was like, hey, I don't really like documentaries. Can you write it in a book? And I was like, oh, sure. So I self-published it, hit print on like a thousand and just like handed it out to my friends and people in my church. And somebody walks up to me and they go, hey, I hate to break it to you, but there's three typos in it. I'm like, oh, crap.

21:11So I fixed those three typos and reprinted. And then I'm speaking at one of the largest churches in America. And a woman walks up to me. She says, hey, there's about four typos in your book. Can I help you? I'm like, Jesus, what is wrong with you, Ryan? And you have no idea how many people proofread it, including me. So then we do a third version and we're like, hey, why don't we why don't we update it and like give it a new look and feel. It's been like two years now with all these typos. And then somebody was like, hey, can you add like some verses to it? Like I like it to be a little bit more spiritual.

21:40So I made a little bit thicker one and never even put that one on Amazon. So there's like four versions out there. My mom has every single version of Chasing Failure. And so I talk about typos in Chasing Failure because people have this idea. I'm not going to move forward until it's perfect. And I'm just like, well, guess what? Then you will never move forward. It's never going to happen. So I just decided I'm going to move forward with imperfection. So I'm reading the audio book, doing my own audio book for Chase Failure, and I find two typos. And I was livid. I was livid in the studio. But then I just thought, yeah, but in the book I write, hey, you might find two typos.

22:20Ironically, people haven't actually found them yet. I know where they are. But I actually have it. It's been out for 18 months and no one has actually caught it yet. And that's just me just maybe being super anal about it, whatever. But I am consistently every single day moving towards something that intimidates me. But it's good for me because that means I'm always learning and always moving forward. Well, I'll tell you that book, as you know, became a USA Today bestseller. And I mean, to have that level of success is incredible. It's funny. My first book, Confidence Creator, I self-published.

22:53much like you i just said okay i'm just gonna write this book having no idea what i was doing there's three mistakes in the book i never thought to redo it by the way so kudos to you i just left them and thought you know what let my imperfections rock i'd always rather be the person that wrote the imperfect book than the person on her deathbed that said oh i never wrote that book that i had inside me never got it perfect right so to me i love that you had the mistakes and i also love that you've continued to evolve it. And that once it got to this level, that's when it completely took off. But that would have never happened had you never sat down and written that small first version.

23:31Oh, for sure. And, you know, it's interesting when we were first working on this latest version of Chasing Failure, talking with the publisher, talking with the team. And, you know, one day I just say, hey, it'd be great if I hit New York Times. Like, let's just go for it. And then here's what's interesting. everybody started working harder i'm like where was this at before like where y 'all been where are you you not now i get to a game now now that i now that i've set set our goals a little bit higher and i started working harder so that that was for everybody well we sold uh within the first two weeks i think we sold like 13 or 14 000 which is incredible which is enough to hit new york times In fact, first off, this is all public information.

24:18You can see how many units every book on the New York Times, you can see it. So I should have been number three week one and number six week two. You can literally see the numbers. So when a book comes out, it comes out and then you have to wait a whole week before all of the numbers come in. And so that whole week was just so nerve wracking because you're like, yo, we are we're going for New York Times. We have enough to hit New York Times. But it's like, are you a big enough name? Are you you know, there's a whole bunch of unknown boxes that you you have to check. And so when I get the email, it says, hey, you did not hit New York Times, but you hit USA Today.

25:12Yeah. And, oh, we're talking with the Wall Street Journal. We don't know why you weren't on their list because you obviously sold enough. I mean, we put like a six-figure marketing plan together. That worked. Like we did everything in our power to get the dub and we lost. And it's just like, oh, poor you. You landed on USHNA. I was going to say, Anne Ryan, how many people have come to you after reading your book to tell you their story of how they broke through fear and failure because of chasing failure oh thousands thousands of people i mean people i got people out there trying all types of stuff even stuff that even i'm like hey man i think you might have took the book a little too literally i don't know i i don't i don't know about that one buddy yeah you did that one that one oh i didn't say get a second mortgage okay i said explore it okay i said send them an email i like you you took going to look too far, but people are so resilient.

26:12People are so brave. I'm impressed with the emails that I get from people every single day. There are people that have just pitched movies, business proposals, book proposals, that have started podcasts and YouTube channels, all because they just did it scared. And I just, I'm so impressed with what they've done way more than what I did to play a part in that. But like there's a lot of brave people out there and there's nothing more rewarding than that. I'll never forget interviewing Sarah Blakely from Spanx and she explained her father every day when they would sit down for dinner would say, share your failures, tell me your failures for the day.

26:56And her family celebrated failure so much so it was ingrained in her that this idea of trying something new that she knew nothing about, it was very normal for her. Oh, of course I'm going to do this. Unlike 99 % of us who had been, you know, basically the messaging of you've got to be able to win. Don't do it. You'll look, you'll look bad. You're going to be judged. You're going to feel, you know, ashamed and cut to, you know, this woman becomes a billionaire by stepping into failure on the regular, which is entirely your message. It's, it's incredible for me to see how many of us, the majority are held back by failure.

27:34And I think a lot of people aren't as held back by failure, the fear of it. Me predict, like they're predicting, all right, according to my assessment, I will fail. Therefore, I won't even try. That's where I try to help people go, hey, you can't sell a book that you don't write. You can't get people to listen to a podcast you won't record. Even this morning, it was like, hey, are you going to do a book tour? I'm like, well, what if I go to a Barnes and Noble in New York and nobody shows up for this book signing. I'm like, man, I'm just sitting in parts by myself. It's just like, no, like you, you gotta, you gotta put yourself out there.

28:13I mean, you gotta have a plan too, but yeah, I think the difference between people who are successful and people who don't get all that they want from their life is that successful people were willing to go sit in the bookstore and be by themselves. They were willing to try the thing and fail, whereas most people would rather just acquiesce to the status quo and settle for mediocrity. I'll tell you, I settled for my version of mediocrity being in corporate America for, you know, 14 years and saying I have golden handcuffs. I've got to stay, you know, because this was my excuse, right? But it was because I was afraid of what else could be out there beyond what I saw in front of me and what I knew to be what I thought a truth.