Ep. 59: Ryan Leak on Why You SHOULD Chase Failure (Part 1)

In this episode, David sits down with Ryan Leak, Speaker, Author, Executive Coach, and Podcaster, to discuss why you SHOULD chase failure.

Buy David’s NEWEST Book “Trusted Leader”: https://amzn.to/3luyqf1

Ryan’s Bio:
Ryan Leak is a speaker, author, executive coach, and podcaster from Dallas, TX. He’s known as the ultimate risk taker from two documentaries, one being the Surprise Wedding where he proposed to his wife and married her on the same day after he planned the wedding for two years. The second documentary is called Chasing Failure that displays his journey of trying out for the Phoenix Suns. He speaks to over 50,000 people a month and trains upwards of 12,000 leaders a year from C-Suite Executives to professional athletes.

Ryan’s Links:
Website: https://www.ryanleak.com/
“Chasing Failure” by Ryan Leak: https://amzn.to/3ru3dw2
LinkedIn: https://www.linkedin.com/in/ryanleak/
Instagram: https://www.instagram.com/ryanleak/
Facebook: https://www.facebook.com/ryanleak
Twitter: https://twitter.com/ryanleak
YouTube: https://www.youtube.com/channel/UCqoJtQgM2gMlGf8BaZIZglw

Key Quotes:
1. “What’s so bad about failure?”
2. “Failure is the common denominator of the most successful people in the world.”
3. “You gotta miss some shots to make some shots.”
4. “Your calendar will determine the trajectory of your life.”
5. “You gotta spend money to make money.”
6. “We long for routine.”

Links Mentioned In The Episode:
“Chasing Failure” by Ryan Leak: https://amzn.to/3ru3dw2

Buy David’s NEWEST Book “Trusted Leader”: https://amzn.to/3luyqf1

David’s Links:
Subscribe on Apple Podcasts: https://apple.co/36AXtp9
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Follow David on Twitter: https://bit.ly/2BEXgla
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Show Transcript

David Horsager: Welcome to the trusted leader show it’s David Horsager again i’ve got a special guest an amazing gentlemen you’re gonna have some surprises in store today but welcome to the show Ryan Leak.

Ryan Leak: Man what an honor it is to be here i’m really looking forward to this conversation.

David Horsager: Likewise, well you know a little bit about Ryan, many of you might know him he speaks all over the world, he affects maybe 50,000 or more people a month, he is an executive coach he’s an author he’s a filmmaker he you know we have so many mutual friends.

David Horsager: This is finally have a little bit more intimate intimate connection but there’s no surprises about you, we just got to.

David Horsager: get out of the way if anybody seen the documentaries both of the phoenix suns and also tell us, just a quick.

David Horsager: Quick quick story about this marriage proposal you proposed and got married the same day.

David Horsager: After two years of planning.

David Horsager: yeah get into your book and how that even aligns with really who you.

Ryan Leak: Are but tell all of that.

Ryan Leak: Well, when me my wife or native native for five years you’re 30 I or Tele French thought would be cool to get engaged married on the same day, I had no idea what that meant, so I guess it started planning a wedding behind her back June 7 2013.

Ryan Leak: get down on one knee instead of manda we marry me, she said yes, I said just getting we marry me today.

Ryan Leak: And we opened up this lounge room door and about 85 of our family and friends are standing in there with the sign that said today rolled in the dress hair stylist makeup artist.

Ryan Leak: Everything that you would need to get engaged and married on the same day, but that, on YouTube about four months later, went viral guys to do.

Ryan Leak: a bunch of TV shows, and you know, led to a bunch of fun stuff which actually is how we actually even got the book chasing failure because we want to clean the TV show.

Ryan Leak: And on the TV show my wife surprise me by getting me connected with the late, great Kobe bryant and I was like oh my gosh what is happening right now, and so colby invited me out to staple Center.

Ryan Leak: To just come hang out with the lakers and I played college basketball was an all American.

Ryan Leak: At a D3 ish school why I say D3 is is because our D3.

Ryan Leak: status was pending the years I was playing, and so we were in not the nc double a we were in the ncc double eight which stands for for national Christian college athletics association, so I like to say, amongst Christians.

Ryan Leak: I was really, really good but I never I never pursued the pros and so getting ready to meet Kobe i’m thinking man I gotta I gotta go for this and I just realized the odds were stacked against me and then I was gonna fail.

Ryan Leak: And then I woke up the next day and said but what’s so bad about failure, I mean isn’t this the common denominator of the most successful people in the world, so let’s give it a shot, so that is, that is how chasing failure, the book was birthed and that’s a little bit about me.

David Horsager: that’s a great start and you’ve got two amazing kiddos and amazing wife, but your whole you know if I look at your life and what you’re about.

David Horsager: you’ve done some amazing things, but it is marked by this risk taking this willingness to.

David Horsager: Face failure and I love what you say in the book even.

David Horsager: Basically, the the own the people you admire the people you love the people you look up to they all failed, and yet we’re all sitting here thinking we want to get around the failure we want to and you kind of make this this point of let’s chase failure if we want to be like that.

Ryan Leak: Absolutely you just I think we all if let’s say we’re a songwriter we all want to write a hit song you only want to write hits but you got to write some bad songs to get a hit song.

Ryan Leak: You got to miss some shots to make some shots I mean it’s all a part of solid part of the process, no matter anybody in this world that wants to do anything.

Ryan Leak: They have to try things and I think the last.

Ryan Leak: Three years somebody said this to me, the other day, they said i’m not sure if i’m ready for my junior year of Kobe and I just thought has it been that long it really have but i’d like to say, the last three years.

Ryan Leak: i’ve really taught us that if you’re not innovating if you’re not thinking outside the box, you may not survive in this marketplace that that we work in because things are constantly changing and most people don’t like change and cove at 19 did not ask us for permission.

Ryan Leak: And so I think people now more than ever.

Ryan Leak: have to be willing to try something and take some risk.

David Horsager: How do you how do you do it, so you know you took a risk your wife said yes oh lovely story I get to be on a little queen latifah show.

David Horsager: You take some risks.

David Horsager: You know there wasn’t a huge downside, with getting a try it with the sons, even though you didn’t make the.

David Horsager: team right.

David Horsager: hello, even though it’s amazing right but, but now, what are you doing to chase failure now, what are you doing you’re going.

David Horsager: To be you know executive coach to pro athletes and you’re getting to speak in some of the biggest platforms in the world.

David Horsager: yeah what how are you chasing failure now.

Ryan Leak: Well, you know it’s The funny thing about I think all successful people not even just myself is we give the illusion.

Ryan Leak: Of highlights, we give the illusion that we never have down days that we never get rejected that no one is telling us no, there will never be a published list of guests you’ve requested to be on your show that told you know.

Ryan Leak: it’ll never happen.

David Horsager: Right.

Ryan Leak: or any show no one publishes that yeah I get to speak at some really, really great companies, I have a speaker’s bureau is great they pitched me to 230 companies this year well sure 10 to 15 said yes, but what do you think keeps me up at night.

Ryan Leak: Right those other you know, so you just think about all of those other 215 that that i’m just going what what what did I do wrong.

Ryan Leak: What what what what’s wrong me and so as far as like me and my team go.

Ryan Leak: we’re always chasing failure always trying new things we we came up with this thing the other day called insta documentaries and we were like can we do 62nd documentaries for instagram and so.

Ryan Leak: We budgeted out film the whole deal and it looked great it sounded great the script was just bad and I wrote it and so it’s not me you’ll never see it, but we tried it.

Ryan Leak: Does that make sense, like we were trying to figure out ways to create helpful content that adds value to people’s lives and so.

Ryan Leak: This Friday, we are going to the studio we booked for four hours and a little bit right before I got on this podcast I the the head director is like hey So what do we do on Friday I went great question so really great question.

Ryan Leak: Where where we’re going to we’re going to try some stuff we’re going to film a lot.

Ryan Leak: What will come out of it is still is still tbd but that’s that’s what i’ve been doing my whole life i’ve just been jumping off of the diving board and teaching myself to swim so even with my internal team on the book side of things, was you know we said hey.

Ryan Leak: We need to hit New York Times that’s the goal we’re going to hit New York Times here’s what here’s what here’s what happened, David it was like.

Ryan Leak: Everyone on my team elevated their game everyone started bringing their a game, because the goal was higher, so the book comes out.

Ryan Leak: We we sell more than enough to hit New York Times, you can pull the numbers, you can see how many I sold that week versus the books that were actually on the New York Times, but.

Ryan Leak: I doubt the New York Times, is going to remove Matthew mcconaughey for Ryan league at this stage in my career and so, so we did not hit New York Times and and I was that was a bummer for me, because we we put a lot of energy, a lot of resources and to make that happen.

Ryan Leak: But again, my message of chasing failure is easy to write tougher to live.

Ryan Leak: And we hit USA today, so my friends are like trying to celebrate me they’re like do USA today that’s awesome i’m like no it’s not.

Ryan Leak: it’s not awesome they’re like what’s wrong with you come back to the real world and i’m like you’re right, and I think that is the point of saying hey we’re.

Ryan Leak: we’re going to take a bunch of risk to try some things and and we’re going to we’re going to see see where the where the chips are the chips fall because at the end of the day, it’s all risk.

Ryan Leak: it’s all risky I mean I think some people think oh I don’t wanna I don’t want to take a risk, because what if I fail and it’s like well doing nothing is also risk.

Ryan Leak: yeah it’s.

David Horsager: Much more in that camp, I know it’s good to have people alongside me that you know pause think through stuff, and all this, so we don’t I bought a company one time lost everything in two weeks for our family have just written for my first.

David Horsager: daughter was born and.

David Horsager: You know I learned a lot about what we talked about around here, trust and.

David Horsager: Because I was so quick to trust, people often but there’s there’s all those things.

David Horsager: Create our journey, give us depth and and I would rather be with people that are sure I am I know i’m a little bit that way.

David Horsager: What is it ready fire aim, you know, but I liked him the movement does build momentum does build momentum it’s not always the right answer, certainly, but it’s one of them, I want to talk about a couple takeaways from.

David Horsager: This book and I want to get to what you’re working on next.

David Horsager: Because I don’t really excited about that i’m thinking about that.

David Horsager: And and but but let’s talk about this quick there’s a whole lot of nuggets in the book if you don’t have it chasing failure, it really gives this.

David Horsager: Not just permission, but encouragement exhortation to like you know what you want to be better you’ve got to chase failure first but let’s let’s actually a couple things.

David Horsager: The the idea of motivational speakers saying you know what what is it good never.

Ryan Leak: give up like this never give up.

David Horsager: ish right true statement.

David Horsager: But what about these five questions.

David Horsager: You talked about um.

David Horsager: You know who wants to be a millionaire five questions you need to ask yourself to count the cost of your dream.

David Horsager: yeah tell us about it.

Ryan Leak: So I think it’s important that.

Ryan Leak: You know, whenever it is that whatever it is that we’re trying to accomplish one, we need to know why we’re doing it, I mean some people want to do it just because they either want to be famous they want to be admired by.

Ryan Leak: A certain group of people, or maybe they want to be rich, you know, whatever their reason may be, I think you just need to have a good reason, a good why.

Ryan Leak: And I think when most people think of the word million million is sort of a gold standard for everything, a million downloads million customers a million dollars a million million million million well.

Ryan Leak: When you think about it, it looks great from a distance until you talk to people who have a million followers That means they also have a million opinions.

Ryan Leak: And also means that they they could have a million critics, I mean there’s so much that comes with anybody that achieves anything anything million, you know you look at professional athletes and.

Ryan Leak: There are some of the only people in the world who salaries are plastered all over the Internet and people look at that and try and like put it in their face and go Look how much money you made this year and it’s like.

Ryan Leak: yeah dependent on the state that they live and they might get half that maybe you know, and so you think about.

Ryan Leak: Man it’d be great to make $40 million and being an MBA but you’ve never written a check for 17 million to the irs because that’s what a lot of athletes have to do and so.

Ryan Leak: So the question that I really pose to people in the book is going, are you sure you really want to be a millionaire are you really sure.

Ryan Leak: That you want to be as successful as you think you might want to be, because your relationships change the more success that you have.

Ryan Leak: People feel like you owe them access that your phone number should be given to thousands of people and how do you do that, how do you who do you respond to.

Ryan Leak: You have to build a team that means you get to be a good leader, there are lots of things, on the other side of.

Ryan Leak: of being a millionaire so till we out we outlined some questions that we think are very important for people thinking about their goals you know, one of the one of the biggest questions.

Ryan Leak: Is you know how do How do people that I view a successful whether they’re a millionaire or have a million downloads or a million subscribers whatever it is, how do they spend their time.

Ryan Leak: What what what is what is their schedule in my executive coaching practice I tell people all the time.

Ryan Leak: Your calendar will determine the trajectory of your life, what are you spending your time doing if i’m sitting with the C suite executive i’m going.

Ryan Leak: You might think your job is to put out fires, but if that’s all you do you’ll never move this ship in the direction you actually wanted to go, so you are in control of your schedule, it is not dictated.

Ryan Leak: by everyone else around you or the problems, so we have to build leaders to be able to help solve those problems so you’re you’re not achieve firefighter you’re the CEO.

Ryan Leak: And so, so and I think about the disciplines that are required at that level sometimes it’s the resources that you need to you know the old adage, the first thing I heard about businesses get spend money to make money and most people aren’t willing to do that.

Ryan Leak: They they want things to be easy, they want a successful person to glory without their grind.

Ryan Leak: They want their they want a successful successful persons destination without having to wait in line at all.

Ryan Leak: And so I think behind the scenes of any successful person you hear some stories that you go you never posted that on instagram you never I never saw that to eat, I never saw that story.

Ryan Leak: And so I think, overall, the question that I think all of us should be asking whenever we admire somebody whether it’s on our phone or somebody we actually know, I think we should be asking the question, what does it cost to be you.

Ryan Leak: What what is.

Ryan Leak: What what what don’t people see and and I think that that’s a very, very important question that we should ask.

David Horsager: That jumps in to really maybe we’ll go back and forth you a little bit, but some of the new work that you’re.

David Horsager: Working on and probably inspired with some of your Executive coaching and everything else is self leadership and.

Ryan Leak: Thinking about.

David Horsager: How do you lead yourself, well, I want to ask you, first because I asked us to almost have everybody, because I, at least I have found.

David Horsager: yeah i’m doing well and in others, that I respect that those that are leading others.

David Horsager: yeah both have the opportunity to to be a part of the lives of presidents of countries and companies and and and yet we’re flying a load and i’m thinking about things I did well and things I regret from as my four kids are moving on first one in college this year and thinking through.

David Horsager: How would I do this, how am I going to do these this next season.

David Horsager: Because.

David Horsager: If you’re on a couple hundred flights, a year and you’re doing all the things you do, how are you leading yourself well.

Ryan Leak: yeah you know it is a.

Ryan Leak: it’s attention to manage I like to say, and there are some month I just take off.

Ryan Leak: I don’t do anything.

David Horsager: Is that systemized i’m gonna jump in here a little bit is that.

David Horsager: A system like I always do that or I just like oh I don’t have work so i’ll take this month up, I mean.

David Horsager: How do you.

David Horsager: yeah is that a sabbatical every year for a month is that, how do you do that, I know, Ken blanchard studies that, basically, you know here, he is.

David Horsager: A unit, you know, and I know people that are at that should not be talking to anybody anymore.

David Horsager: they’re saying the same thing they were 40 years ago.

David Horsager: and bringing up people like Ken blanchard who are at and they’re fresh and relevant and capable and wise still and I think part of it goes to every summer.

David Horsager: Basic is up at the lake with his family writing reading thinking and he does that, as part of his life but he’s got this system, every year, what, what do you think.

Ryan Leak: Mines August, as my birthday mom.

Ryan Leak: And my kids are getting ready to go back to school and that’s that’s that’s where I I typically retreat, I know that November in April, are always going to be what I call gauntlet months for me to conferences and.

Ryan Leak: People are always doing you know a lot of conventions and seminars and different things like that so November is even crazier than April, because everyone’s going their last meeting before the holidays so.

Ryan Leak: So I.

David Horsager: salute so let me just ask you, is it like okay hey here’s a quarter million dollars to do this project is that an absolute no in August, if I call you or is that a is that a well now we’ll shift around and maybe do this because we got that.

Ryan Leak: For quarter mil.

Ryan Leak: or quarter mil, we are sending out an extra week off in July, you know my view like there’s there’s.

Ryan Leak: You know, but, but again that’s what people don’t tell you about success, because you think Oh, I would never say no at that level.

Ryan Leak: But you’d be surprised when when you have to, and I think the reason it’s not so systematic is because, as you understand even more than I do, having older kids.

Ryan Leak: Is seasons change and kids are into certain things that you really need to be President, so this past summer my my son was in soccer.

Ryan Leak: But he wasn’t all that into soccer and so you’re measuring like How important is it for me to.

Ryan Leak: To be here, I want to be here i’m gonna do my best to be here.

Ryan Leak: But if that it can’t be here i’m not the I don’t subscribe to the you got to be at every single game every single event, but I do think that you have to be President, you have to be engaged in what’s happening in your kids lives.

Ryan Leak: It would be a shame if you are winning at work and losing at home.

Ryan Leak: And you know I say that.

David Horsager: yeah I absolutely agree with that, I mean, I want to be a hero at home and yet we’re called to these lives of trying to.

David Horsager: You know, in our in our world change trust levels and countries and cultures and worlds, and I do think there’s there’s actually a problem on the other side it’s not an out, but this problem of kids centric culture.

David Horsager: Where the.

David Horsager: Center I if you don’t miss the game you’re you know you’re a bad person or bad dad I think that’s the worst we one of the best parent well.

David Horsager: Actually, the book, there was some frustrating parts of it that I don’t agree with, but this one parenting book, I read, one of the key positive positives was your child is a welcome member of the family.

David Horsager: There are welcome members that they’re not the Center.

David Horsager: Here, and I think we can teach a lot of entitlement and host or things, everything is about them, I do not think I think my kids is that you are present, you are there you’re with me, you are you.

David Horsager: i’m at certain things I want to be at but i’m also texting videoing doing all these things to stay connected or trying.

David Horsager: to fit in perfectly.

David Horsager: I can tell you times i’ve done, I wish I would have done it differently, and all this, but I also am with you that i’m the mark of a great parent I know parents that are there every day they’re not connected to so.

Ryan Leak: 100% and I just I get to meet the adult.

Ryan Leak: That.

Ryan Leak: said.

Ryan Leak: One of two things either i’m successful in my career or I have a great relationship with my parents, because my parents read everything.

David Horsager: Right.

Ryan Leak: I never heard anyone say that but yeah we do have a cultural pressure to be at everything i’m just going, why is not a predictor of.

Ryan Leak: Future better relationship or future success now again complete absence is definitely a future indicator of something not being successful but I don’t think that that’s the that’s the intent and so So for me there’s their seasons, where August is a.

Ryan Leak: You know we’re not doing anything in August again Cohen it’s like hey will you turn on your computer into a virtual event for an hour sure.

Ryan Leak: But why not, but as far as like hey there might be a no travels and i’ll do that a couple of times a year actually where I didn’t know travel for two weeks, three weeks.

Ryan Leak: And you know my son is now starting basketball, which is a whole different ballgame because it’s like hey are you going to coach i’m like.

Ryan Leak: I don’t know this this particular season, I told him hey I i’m not going to coach but I will be there with the whistle on the side and how about what practices and whatnot and he and a friend, are doing it after this winter.

Ryan Leak: And i’ll be able to make you know, most of the Games, but not all of them, and so you know every every season is just a little bit different.

David Horsager: What about this, what about routines that like daily routines for you to stay.

David Horsager: You know.

David Horsager: Some of the work you’re you’re you’re thinking about is self leadership, what do you health wise faith wise family wise, what are you doing every single day are there some routines you have.

Ryan Leak: I tried to take my son to school every single day, and we do a verse of the day I want his mind to be solid and.

Ryan Leak: You know i’d love to say that that’s always been a daily routine.

Ryan Leak: in Texas, he just started kindergarten last year, but in Texas you don’t have to go to kindergarten and because of the back and forth with hey you got to be home for two weeks and we just homeschool them so.

Ryan Leak: You know he’s only been at school now two months, so the routine routine changes and there’s so many different worlds that i’m bouncing in between, I think we long for routine, but one of them from me just as a writer and a speaker i’m reading and writing every single day.

David Horsager: something you do when you do that when you when you’re reading right when’s the when’s your best time.

Ryan Leak: It just it just depends, you know, and I talked about this in my next book is this trying to be this.

Ryan Leak: Well, rounded person and trying to score tend in every area, spiritually vocationally marriage parenting.

Ryan Leak: Health wise eating healthy working out, you know so yesterday I jumped up my son.

Ryan Leak: One of my friends, has a gym and shooting machine and his house and lives, you know 1010 to 15 minutes away and i’m like hey, can I start paying you didn’t just have a gym membership to go here.

Ryan Leak: And so, yesterday I felt like a really great routine and i’m like I think I could do that i’m going to try again tomorrow.

Ryan Leak: But, but then again in November it’s the gauntlet month I just don’t know that i’ll be able to.

Ryan Leak: And I think naturally i’ve always been just like a fit person my metabolism is pretty high as well, and so just being in my peak shape is difficult to do also while traveling and so.

Ryan Leak: I wish I had more of a routine, but I would say, the thing that is a staple in my life is my to do lists so every Sunday night or Monday morning I create a very.

Ryan Leak: Particular to do lists, that is categorized by all the different buckets that my life has from speaking from church to.

Ryan Leak: How many guys on that in a week.

David Horsager: How many how many things.

Ryan Leak: uh I can show it to.

Ryan Leak: 60.

David Horsager: And, and what percentage of wins of the 60 I know you’ve got something in the book about just getting a daily win, but what do you, what do you have for like what’s what’s likely out of those you can all these things you get 30 done.

Ryan Leak: uh So this was this is one from last week I got.

Ryan Leak: yeah I will say, by the end of the week i’m if I have 60 things on there.

Ryan Leak: Probably 55.

Ryan Leak: yeah probably going to defy and i’ll put some things on there, so, for example, at the beginning of October I said, you need to write all of your content for November before October so.

Ryan Leak: The reason I do that, so that in November, while i’m working a lot when I do get home, I can really be home and not really need to think about what I got going next.

Ryan Leak: Does that make sense, so yeah I tried to do some things ahead of time.

Kent Svenson: Hey it’s Kent Svenson, producer of The Trusted Leader Show here.

Kent Svenson: That’s it for this week’s episode. But make sure to tune in to next week’s episode for part 2 of David’s interview with Ryan Leak.

Kent Svenson: In it, Ryan gives us a preview of his 12 questions for self leadership

Kent Svenson: talks about the greatest tool for bringing about change in diversity, equity, and inclusion, and he discusses the importance of those in power giving access and opportunity to those who don’t.

Kent Svenson: You won’t want to miss next week’s powerful episode.

Kent Svenson: But that’s it for now. Thanks so much for being here. And until next time, stay trusted.

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