Navigating Life’s Toughest Moments: Ryan Leak’s Lessons for Business and Beyond

by | Jan 16, 2024

Ryan Leak, an acclaimed speaker and coach, brings a fresh perspective on leadership and generosity. In this insightful interview, Leak shares his journey and how he empowers others to unleash their potential. He delves into his philosophy of generosity, not just financially, but in kindness and support, illustrating its transformative power in both personal and professional realms.

Leak’s forte is guiding individuals and leaders to recognize and nurture their potential. Through candid conversations, he offers invaluable insights into building meaningful connections and leveraging generosity as a tool for change. His approach transcends traditional business practices, highlighting how empathy and giving can reshape leadership.

This episode is a profound exploration into the dynamics of leadership and generosity. Leak’s compelling narrative underscores the significance of viewing potential over performance and how this mindset can revolutionize personal growth and business success. His stories and wisdom inspire a rethinking of success metrics, emphasizing generosity and impact.


“Every single day, I wanna put courage inside of people to be able to do things they never thought they could.” – Ryan Leak

“I’m trying to make as much money as I possibly can, just for a different reason. So we have the same drive, but we just have a different purpose.” – Ryan Leak

“Hey, I am not on this planet to get something from other human beings. I am on this planet to give something to human beings.” – Ryan Leak

“There’s a lot of, it’s interesting, like, you know, the first part of this episode, we’ve talked a lot about generosity, but there is, I think that’s the result you get when greed is at the center of your business.” – Ryan Leak

“You don’t need to have mine, but you do need to have yours. And make sure it’s not your parents. And make sure it’s not your bosses. Make sure that it’s yours.” – Ryan Leak

“People aren’t pawns on a chessboard to you, you’re not making moves, but you’re genuinely interested in people and serving them.” – Ryan Leak


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Dr. Jessica Kriegel: Here we are with Ryan Leak. My first and favorite question is always, what is your why?

Ryan Leak: What is my why? You know, I think when I wake up in the morning, I think that there are so many people navigating so many things. They’re navigating pain, they’re navigating insecurities, and I think I have the gift of encouragement. And the whole idea behind encouragement is this idea that you are putting courage in somebody. That’s how I think of my day. Every single day, I wanna put courage inside of people to be able to do things they never thought that they could ever do in their life. And sometimes that’s starting their own business, sometimes that’s forgiving somebody that hurt them. But I think I’ve been given a gift to give people the courage to pull off things they never thought they could. So that’s my one.

Dr. Jessica Kriegel: You know, I love that being your why, because that’s what you do for me. I’ve been the person that you’ve put courage into. And, you know, it’s not every day I get to interview someone on this podcast that is not just someone I look up to, but someone that I call a friend. And you are someone I call a friend. And what I love about you and what I would say about you and have said about you to anyone that listens is you walk the walk. You’re a keynote speaker who walks the walk off stage.

Dr. Jessica Kriegel: And the story I will tell to the audience to get a sense of how you walk the walk. I mean, we met when we were both keynoting at the same event in Chicago. And we just chatted in the lobby, hey, nice to meet you keynote speaker, keynote speaker. We exchanged a few interesting stories and then we stayed in contact. And a few months later, you called me, your career is bigger than my career. I’m just gonna put that out there, right? And so you called me, well, whatever, you called me.

Ryan Leak: Yeah. Yeah.

Ryan Leak: I don’t know about that, but yeah.

Dr. Jessica Kriegel: And you said, hey, just thinking about you, wanted to know if there’s anything that I can do for you today. That was the purpose of your call. That doesn’t happen in the business world. It doesn’t. I mean, it happened once with me with you. I have started doing it to people because it inspired me so much, you know? But that’s remarkable because especially in the world, the keynote, everyone is trying to get something from everyone else. And I have this sense that many people in business, I call them,

Dr. Jessica Kriegel: The wanters, you know, there are people that want something that are trying to network to get something who are always looking over your shoulder to see if someone more important is behind you. And you’re not that. So I had to brag about you for a minute, brag about me getting to be your friend. So here’s what I want to dig into today. You’ve done so many things right you’re a filmmaker, you’re an author, you’re a keynote speaker, you’re a preacher and

Ryan Leak: Mm. Oh, that’s very kind of you. Yeah.

Dr. Jessica Kriegel: The thing I wanna ask you about of all the plethora of topics we could talk about is how you marry, this was one of the first things I asked you about, being a preacher, being a man of God, and speaking to corporate leaders, and how you intertwine those two things or not the boundaries of appropriate workplace conversation and your beliefs. I mean,

Ryan Leak: Yeah. Yeah. Yeah. Sure.

Dr. Jessica Kriegel: That’s complicated, right? Do you feel like that’s complicated? You make it look easy.

Ryan Leak: I feel like it used to be more complicated.

Until I just gave myself permission to essentially just be myself. And what I get to do in the church is I get, I have what I like to call a PhD in pain because I get a front row seat to people in their darkest hour. When people are having the worst time of their life, whether they’re a Christian or not, they look for somebody like me with faith. And so.

My phone is full of some of the saddest text messages, people in their worst of times. And I can’t tell you how many times I’ve been out with my wife. I can’t tell you how many times I’ve been on vacation with my wife. I’m just like, oh, bae, look, what happened to this person? Or this person’s getting divorced. Or oh, they lost a child. Or their husband left them. Or just the worst of the worst of the worst. And it’s like, and I get the ability and the opportunity to encourage those people.

Well guess what? Those people have jobs.

Crazy concept, crazy. So I just started owning it. I just started letting corporate America go, I actually know what your people are dealing with that they’d never tell you about. I have the ability, even through our executive coaching practice, my corporate unique gifting is I can get just about anybody to tell me how they’re.

Dr. Jessica Kriegel: No.

Ryan Leak: And so I’ve just leaned into it in the sense of, this is who I am, I don’t want you to hide who you are. I’m not gonna hide who I am. Ultimately, companies around the world have paid me to deliver a keynote. So that’s exactly what I’m going to do. I’m gonna deliver a keynote. I’m at the highest level that I know how to. I am consistently tweaking.

My keynotes every single day, constantly, because I’m addicted to getting better. I’m not trying to be better than another speaker. I’m trying to be better than Ryan was yesterday. And so in that, I’m trying to deliver a very high quality service to an organization or two leaders. And inevitably when that organization admires the work that I’ve put into my.

Ryan Leak: That’s where they ask questions like you do. So tell me your why. What gets you out of bed in the morning? And then I’m able to share my faith. I was speaking for a well-known retail chain and a lady walked up to me and she said, I don’t even know why I’m telling you this, but here it is. My son has an incurable disease.

Ryan Leak: I don’t know why I would share that with you. I haven’t shared that with anybody here. I said, I know exactly why you’re sharing that with me. She said, why? I go, because I talk to a God every day that specializes in incurable diseases. Can I pray for your son?

And so I prayed for her son in a book line. People were like, that was amazing. It was like.

Ryan Leak: What else do you do with incurable diseases? What do you expect me to do? And I mean, executives are like, dude, that was incredible because who’s gonna come and pray for their team? That’s not what they paid me to do, but that’s what was asked of me in that moment. This is a woman that just wants her baby to be better. And so I’ve just found that in my keynote, I don’t lead with it, I lead with my craft.

Dr. Jessica Kriegel: Hahaha!

Ryan Leak: Being excellent at what I do. And inevitably faith conversations typically always come up. And if you Google me, it’s gonna be really hard to see that I’m not a Christian. It’s just, this is what it is. If you’re YouTube and you’re gonna find like a thousand sermons, it is what it is. But what I try to do is I try to make every keynote that I do, not about me, it’s about.

That organization. And I’ve just found that when you do that, if you are a believer, it’s amazing what they will make space for when you put them first and serve them well.

Dr. Jessica Kriegel: So what do you need encouragement around? What is your challenge? What’s the thing that weighs heavy on your heart?

Ryan Leak: I mean, you and I have talked about it before. I think it’s all of the other ancillary products that go around a growing speaking business. I think the elephant in the room with speaking businesses is that they don’t last forever, and they’re very difficult to scale. So you’re always having to figure out what are going to be those offshoot products that you’re able to, I guess, upsell a company, which is really not my style at all. But…

but thinking about the future of my business and what that looks like. And so that those are the things that I’m always trying to navigate in, I guess you could say, needing courage.

Dr. Jessica Kriegel: Okay, so here’s my biggest question and the thing that I probably think about more than any other thing. You know my story, I was a lifelong atheist. I had a spiritual experience that brought me to my knees, literally, and in a moment I became a believer and I didn’t know what I believed in because I had never been to church. So I thought, okay, there’s definitely something out there. I went to divinity school. I went to a different church every Sunday for a year and a half and I read the Bible.

Ryan Leak: Yeah. Yeah. Hmm. Shit.

Dr. Jessica Kriegel: And that was quite interesting to read the Bible because I just, I was shocked to learn that making money isn’t exactly like the goal, right? According to Jesus. And I kind of felt like I had this existential crisis that began and never ended, which is how can I be someone in the world trying to make money, trying to help?

Ryan Leak: Wow.

Dr. Jessica Kriegel: People make money, keynoting at corporations, helping CEOs drive results through culture, sure, but ultimately we’re trying to drive results for capitalism. And yet that’s kind of the opposite of the point. And I don’t know how to, I still every day wake up and think, what am I doing? Is this okay? How do I be in a world that feels opposite of the thing that my faith is pulling me towards? How do you consolidate or integrate those ideas for yourself?

Ryan Leak: Mm. Sure. Yeah.

Ryan Leak: What a phenomenal question. So one of the things that I don’t…

I don’t always lead with, but if you were ever in a coaching relationship with me, you will find out some of the value systems of how we do business. And so for our business, we don’t measure success. I say our business, really our life, if, if I’m honest, we don’t measure our business by revenue or income. We actually measure our business by giving.

So every single year we don’t have revenue goals, we have giving goals. And these giving goals are astronomical. And it goes up significantly every single year. In fact, our CPA and accountant calls me every few months and says, are you sure? This is what.

You want to keep doing it. Our tax people were like, are you sure this is what you want to be doing? And so as every single time I said absolutely, without question. And what’s funny is, is over the past few years, my speaking career has taken off, which I’m incredibly grateful for. But if you really want to know my secret sauce.

It’s really our giving took off. But our giving took off before the speaking.

Ryan Leak: Now I know that, everyone else around me doesn’t know that, but the minute we said, hey, we’ve always lived by giving goals. My wife and I, we’ve been married 10 years, but our giving goals, I wouldn’t even say that they were small. They were definitely more than average, but the minute we started eyeing six figure and seven figure giving as goals, our business drastically changed and…

I, so that’s how I truly balance my inherent belief systems that are very much rooted in a lot of scripture and what I do for businesses. I was talking about my fee because obviously we have to have those conversations all the time with different engagement. And I was at the talk with the church the other day.

And was talking to them about my church speaking fee, which is a very, very awkward conversation. But it’s gotten less awkward because what I told them was I said, hey, this is my fee, but just so you know, we’re gonna get it all lit.

It’s like, yeah, it’s more than you’ve ever paid for a guest speaker and I get that. However, we’re gonna give it all, all the way anyway. So all ministry money that we get is gone. I mean, we just give it away. And lots of business money too, but it’s just that, that’s, so it’s, yes, while we are trying to grow things and get better and grow revenue, essentially as most businesses are, the reason we’re doing that is so that we can only just give more and more and more and more and more. And so, generosity is at the crux of how we balance both worlds.

Dr. Jessica Kriegel: I mean, how do I make every CEO be like you?

Ryan Leak: Well, I mean, that’s part of what we, and it’s, because it’s amazing. I sit with people that make way more than I do.

Dr. Jessica Kriegel: Teach. Yeah.

Ryan Leak: And then they asked me some of the questions, you’re like, so man, so how do you do your business? I go, well, we kind of have opposite businesses. I’m trying to make as much money as I possibly can, just for a different reason. So we have the same drive, but we just have a different purpose. And so, but then I begin to tell stories of the different organizations that we support and the things that we’re contributing to the world around us. And

Dr. Jessica Kriegel: Mm. Yeah.

Ryan Leak: And then it’s like, oh, well, maybe our family should start doing that. I’m like, maybe. But when people ask me, hey, man, what’s the number one thing that I should do if I want my speaker to take off? I always chuckle because I think, I don’t know if you’re really going to like my actual answer. Because I think they’re thinking, well, if you just work on your craft and if you just work on your storytelling, I’m like, no, just.

Dr. Jessica Kriegel: Right. Give it all away.

Ryan Leak: Dude have such a heart of generosity. And I truly believe beyond the monetary value of what we give, I think the generous spirit that my team carries, the generous spirit that I carry with my clients contributes to people going, I think you should have Ryan Lee. And he was a phenomenal communicator, but you gotta meet this guy. Like you’re gonna enjoy just talking to this guy. He’s so kind, he’s so, you know.

Dr. Jessica Kriegel: Hmm.

Ryan Leak: All of these different things that all stem from a heart of generosity. It stems from a thing of saying, Hey, I am not on this planet to get something from other human beings. I am on this planet to give something to human beings. And so whether it’s time, whether it’s money, whether it’s a talent or a gifting, I think it’s important that, you know, at our company, you work for Ryan, you better be a giver.

Dr. Jessica Kriegel: Were you always like this? Did you have a transformative experience or were you raised like this?

Ryan Leak: So, have you read the whole Bible, or you just started, like what haven’t you read? Uh-huh, okay.

Dr. Jessica Kriegel: That’s a great question. I’ve read the whole New Testament. I’m like halfway through the Old Testament right now.

Ryan Leak: Okay, great. We’ll have another offline conversation about what you’re gonna get into, which is gonna be really awesome. So in Acts, Jesus is quoted, we don’t know when he said this because it’s not in the four gospels, but in Acts, Jesus is quoted in red, if you have one of those Bibles that goes from black and red and all the red is what Jesus said. In red, in Acts, you’ll see this phrase that Jesus is quoted as saying, it is better to give than receive.

Dr. Jessica Kriegel: Okay.

Ryan Leak: I read that one day and I thought, I don’t know, because I like receiving stuff.

Dr. Jessica Kriegel: How old were you when you read that day? Okay.

Ryan Leak: I don’t know, I was probably eight, maybe nine, you know? I was just like, I don’t know, I don’t know, we’ll see. But I just thought this is going to be one of those scriptures and verses that I really put to the test. And let’s just see what happens. I had a youth pastor who, he made $50 a week. I knew it because it was like the joke at our church about how…

Dr. Jessica Kriegel: Mm.

Ryan Leak: He would take $5 of his 50 and buy me lunch once a week.

Ryan Leak: And that impacted me. I thought, here is this person who is not wealthy, rich by any stretch of the imagination, but this person is degenerate. And I thought, I wanna be like that. So…

Ryan Leak: Yeah, I just, at a very, very young age, I started practicing this generosity thing. And I can, I made a living testament of the words of Jesus. It is far better to give than receive. I was speaking for Delta the other day, and this guy sees me walking off the stage. He says, dude, that was remarkable. I said, man, thanks, man, I appreciate it. He goes, but man, what I really want from you is those shoes you got on. And I said, man, he said, Jordan 1s. I said, Jordan 1s, man. I said, absolutely. I said, hey man, here’s the deal. If you’re a size 13, consider them yours. He goes, well, I am a size 13. And I said, all right. I grabbed my suitcase, took off my shoes, handed them to him.

Dr. Jessica Kriegel: Yeah.

Ryan Leak: Put on my running shoes that I had in my bag. And I said, hey man, what’s your name? My name’s DeMarcus. We started just chatting about it because are you really giving me your shoes? And I went, they’re just shoes. They’re just like, I’m on the planet to give. And one of the VPs of Delta, he called me like a week later, he goes, there’s this story going around.

Did you give a guy your shoes on the way out? And I went, I mean, he asked for them. I didn’t offer, he asked. I said, sure, you know, it’s just, so it’s like, but I would have given away a pair of shoes when I was 16 years old. Like that’s actually not that new. I truly believe it’s better to give. That story is better.

 Than if I would have said, hey, guess what? I spoke at Delta and they gave me a pair of shoes. You go, okay, must be nice. You’re a speaker and people like giving you stuff. Okay, but the other stories are just so much better. It’s actually inspiring. You kind of go, man, is there some stuff I can give away? And then you think about the stuff you’re not giving away. You’re like, why am I holding on to it? So I don’t know, call me crazy.

Dr. Jessica Kriegel: Right. Okay.

Dr. Jessica Kriegel: But so you’re not crazy, but let me ask you this because I’ll just speak from my experience. I think people are listening right now and they’re probably like, that’s cool, right? I should be more like that. And I have experienced being someone that for years, I mean, when I was an atheist, when you don’t believe in a higher power, you think you are the highest power, right? So you think you’re the center of the universe and that you can manage.

Ryan Leak: Haha Uh huh.

Ryan Leak: I don’t know, wow.

Dr. Jessica Kriegel: Things that you’re in charge. And I actually went to this seminar that was all about you are the writer, director, and producer of your movie. So that gave me the idea that I was really in control, right? And that is what a lot of manifesting stuff gets misunderstood to be, that really you can create anything if you just think about it hard enough, right? But I remember thinking when I was in that kind of a, when I was that person,

Ryan Leak: Mm. Yeah.

Ryan Leak: Mm. Wow. Wow.

Dr. Jessica Kriegel: And I will say that when I was that person, because I am different now that I’m sober and I’ve got three years of sobriety coming up in a few days, yeah, it’s awesome. It’s different, it’s real different because before I thought humility was something I should really try and get more of. I should try and get more, I wanted to get more humble, right? And so I would listen to someone like you talk and I’m like, yeah, that sounds great. Let me get some of that humility.

Ryan Leak: Hmm. Let’s go.

Ryan Leak: Mmm…you. Yeah.

Dr. Jessica Kriegel: And then you can’t get humility. It’s not how it works, but I didn’t have the understanding, the ability, I didn’t have the faith. I didn’t have whatever it takes to be humble. It was a desired trait. And it wasn’t until I got sober and my, you know, in the 12 steps, you have to do a lot of service. They just…

Ryan Leak: Yeah.

Ryan Leak: No.

Dr. Jessica Kriegel: Beat it into you from day one, you need to go serve. Your sponsor is constantly telling you to go do things for others. And you’re like, what are you talking about? I’m trying to get sober right now. Why are you telling me to go clean this person’s house? I’m trying to stay sober, right? And they’re like, yeah, go clean her house. Go drive her to a meeting because when you serve, you get out of yourself and then it starts to all click. And now humility became a gift that felt like grace. I was given.

Ryan Leak: Bam. All right.

Dr. Jessica Kriegel: The gift of humility eventually, but it wasn’t because I wanted it. So for the people who are listening, who are like, it’d be great to get me some of that generosity, right? Or who don’t have it intuitively in them. How do you get that? How do you become that is maybe the better question. How do you coach to that?

Ryan Leak: Yeah. Yeah.

Ryan Leak: Yeah, I think it’s just like anything else in terms of you gotta have goals. And so if you’ve never been philanthropic, let’s say, make it a goal this year to give a hundred dollars to something, something bigger than yourself, a hundred bucks, I’m willing to bet that.

A lot of the people listening today probably could do $100 a month. Well, now we’re at 1200.

Ryan Leak: And let’s just say you’re in one of those positions where if you’re honest, you might be able to afford 1200 a month. Do you see what happens? But most people are like, I’ll give a million dollars once I have a million. This is like, no, if you won’t give a hundred, you won’t give a million. Like a generous heart will follow you wherever you go.

Dr. Jessica Kriegel: Mm-hmm.

Ryan Leak: A greedy heart will also follow you wherever you go. And if you’re not good at managing $100,000, you’re not going to magically get better at managing a million dollars. It’s all just math at the end of the day. And that’s really how we grew in our giving. It was, we started just using different language. We can’t do that. Can’t or won’t.

Dr. Jessica Kriegel: Mm.

Ryan Leak: We’re talking about ability or we’re talking about desire. And I think anybody listening right now can make a decision to say, all right, this is the kind of person I want to be. You get two choices in life, I believe. You can be the kind of person that says, I want to make six figures. It’s wonderful.

Or he could be a kind person and say, I wanna give six figures.

Two completely different kinds of people. And growing up, it was like, if you made six figures, you were somebody. Not in my world. In my world, it’s like, there’s actually a gathering of philanthropists that you have to, there’s a giving benchmark. And some of those people live off of 10% of their income and hit that benchmark.

Dr. Jessica Kriegel: Mm-hmm.

Ryan Leak: And there’s some people that are billionaires and that benchmark isn’t even 0.1% of their net worth. But that room is full of people that have a heart that says, we are not here for us. We’re here to help other people. And so I think anybody can make that decision. I think anybody can make the decision right now that says, you know what? If I want to be a different person, regardless of your religious beliefs, regardless of your upbringing.

Regardless of what you’ve been taught about money, regardless of what you believe about business, I think anybody can wake up tomorrow and go, I’m going to budget who I would like to be in the future.

Ryan Leak: Part of our budget. It’s a part of our budget. This is who we’d like to be in the future. And so that could be, you could sponsor a compassion child where you are supporting a child’s food and clothing in another part of the world. And there’s a nonprofit organization called Compassion who’s known and reputable for this type of thing. You can do that for $38 a month.

If you want to be generous, you can be. But if you are just in this to make a name for yourself or build up your brand or whatever, again, I don’t actually think that there’s anything wrong with that. A lot of great friends that do that and do that well. But if we’re talking about having a truly meaningful life, one that is generous, one that is

full of humility, I think it goes from making it all about what you and what you can get, to what you can get to leverage, to be able to help other people.

Dr. Jessica Kriegel: So what is your perspective on the state of work today and what you’re seeing with the increased unionization? There was a New York Times article that just came out about doctors and pharmacists revolting because they’re feeling put upon.

Dr. Jessica Kriegel: By the healthcare administrators that are their overlords that are disconnected from the patient and yet telling them how to run, which is the same experience that the baristas at Starbucks are having that the manufacturing frontline workers at Ford are having. I mean, union activity is growing because people are feeling oppressed by corporations and corporations are reeling trying to figure that out. What is your viewpoint on that? What do you think when you see those headlines?

Ryan Leak: You know, I think…

There’s a lot of, it’s interesting, like, you know, the first part of this episode, we’ve talked a lot about generosity, but there is, I think that’s the result you get when greed is at the center of your business. And so there are so many decisions that are made in every industry that it really comes down to money and control.

And power, there’s very few industries that are truly pure in that manner. One of the healthcare systems, the largest one in Texas that I get to speak for a couple of times a year, one of the questions I ask each of my clients on a pre-event call is I say, hey, is there any unique language you want me to use when speaking to your organization?

I want to make sure that I speak healthcare in a way that relates to the audience. And I also want to make sure that I’m referring to things the way that they would. So for example, with this particular healthcare system, they don’t refer to the people in their hospitals as patients anymore. They got rid of that language. They call them customers. And the reason they said that they did that is they said, patients…

when we did that, it made the doctors and nurses the center of attention. And the world revolved around the doctor, but customer put us all in the frame of mind of we want to give a great customer experience, customer service, patient service, like nobody, nobody really uses that, that terminology. And so they refer to them as customers and they really want to give them the best possible experience. And so.

Ryan Leak: That’s an example of one good story, I would say, of a whole system saying, hey, we’ve got to look at things differently and we’ve got to make some adjustments. But when you start peeking behind the curtain of a lot of businesses, ultimately there can be a very, very…

a strong sense of greed that I think impedes good business in the sense of saying, hey, how can we serve our customers at the highest level? And obviously, I don’t think the whole world is greedy, but I think when I see headlines like that, I think, well, yeah, that’s what you expect to happen.

Dr. Jessica Kriegel: Do you feel conflicted about being part of the system?

Ryan Leak: Sometimes. Yes, small yes, primarily no.

I think that the system needs bright lights. Like sometimes there can be the, let’s revolt against the system and let’s take them down. Well, guess what? They’re not going down. They got way too much money. I promise you, this is not gonna happen. You’re not gonna win that court battle. You’re not gonna win, like they’re gonna settle off or you might get a check, but bro, you’re not winning that battle.

Dr. Jessica Kriegel: Right, corporations always win. Yeah.

Ryan Leak: And so for me, I’m like, it’s not if you can’t beat them, join them, but there is something about having enough influence to have a seat at the table, to be able to share the story I just shared with you. And go, well, hey, I built my business by giving. And then you’re on a board and people start looking around going, you do what?

Dr. Jessica Kriegel: Yeah.

Ryan Leak: Yeah, just imagine how much money we would have to make to be in that kind of position.

And just imagine if, because there are some organizations that say, we will match your charitable donation up to 20 grand. If you give it, we’ll give it.

I said, just imagine what your people could pull off if they were inspired. And I felt like their work mattered. Oh, and oh, by the way, if you aren’t paying attention to younger generations, that stuff actually matters to them. And so having a seat at the table to be able to share those things is important. And so sometimes I think in our aggression and in our belief system, we can get so frustrated.

Or angry at the system that we lose our influence to be able to impact or influence the system. As a person of influence, I really do consistently consider, is this a hill I wanna die on today in light of the influence I wanna have tomorrow? Not from my followers on social media, but thinking about the amount of influence that I can have in boardrooms with C-suite executives, because of my posture.

They are more likely and open to hear from somebody like me that they have gained respect for and knows that I’m going to do my business with the highest level of integrity that I possibly can. So I’ll take that bet any day. So I’m very much a long game thinker in that way of just going, hey, let’s not get so wrapped up in 2024.

Ryan Leak: That we forget about the 2025 will come and so will 2026. And in light of what we wanna accomplish then, we might wanna think about what we’re saying and posting today and thinking about how we can really add value to the world around us. So those are some things that I often think about, but I rest pretty well at night knowing that when any organization gives me their platform for an hour and a microphone and some slides, I think. One of the things that I do in one of my keynotes based off of my latest book, Leveling Up, is I make the whole room answer the question, what’s my definition of success?

It’s my definition of success. I always say the keyword is my, because if you’re not careful, you will inherit someone else’s definition of success. And perhaps you might get really good at it. And one day you’ll wake up and realize you’re living out somebody else’s dream. 

Ryan Leak: And in that moment, I begin to share my personal definition of success. And I always say this, I say, you don’t need to have mine, but you do need to have yours. And make sure it’s not your parents. And make sure it’s not your bosses. Make sure that it’s yours. I am extremely proud of the work that I get to do in corporate America. And when I talk about that question, I put up a picture.

Of my son. And I talk about how a major part of my definition of success is that the people that know me best respect me the most. Because I would hate to have a career where strangers clap for me all the time, but the people that actually know me go, well, if you only knew the real one. I would hate that. And so I am very proud of my definition of success. And sometimes I’m able to share that we measure.

Dr. Jessica Kriegel: Mmm.

Ryan Leak: Success in our organization and in our family by what we give, not by what we get. So in those moments, while I might see greed in the room, I’ll do that at sales conferences. And the event planner’s kind of going, come on, ramp them up to get more, get more, get more, get more, get more. I gotta come in and go, I mean, I really do want you to win. I do. I really, really do. I just…

Dr. Jessica Kriegel: I’m going to go.

Ryan Leak: I just feel like I’d be doing you a disservice if I didn’t make you pause and ask some serious questions about what we’re all doing and why we’re all doing it. Why are we all working so stinking hard to impress strangers? I don’t understand.

And so I have been given the permission to talk about some of these things in my corporate engagements. And so I, um, so I feel proud of the work that we’re able to do.

Dr. Jessica Kriegel: Last question before we go to the callers. I’m writing a book right now about how to get people to give a rip, you know, like how do you get people to care? And that is a question we get the most often from leaders is how do I get my workforce to care about the goals that we have? And

Ryan Leak: Sure.

Ryan Leak: Yeah.

Dr. Jessica Kriegel: There’s a lot of talk about show them how they connect to the goals. And once they can see the way that they’re making an impact in the company, they’ll care more. But that’s not a given. Just because you show me how the work I do is going to impact the goals doesn’t make me care about the goals. And there’s a whole start with why. And, you know, we’ve been talking about starting with why since Simon’s next TED talk 20 years ago, and it’s not getting better. So how do you get people to care or do you? Is that the wrong question?

Ryan Leak: Cheers. Yeah.

Ryan Leak: I don’t think it’s the wrong question. I think in my line of work, I’m always looking for ways to inspire people. I think there is a lot of conversation in our line of work around performance. And if someone is not doing good, how do you put them on a performance improvement plan? How do you get them to hit their metrics? So on and so forth.

Ryan Leak: I like to bring in a different word that starts with the letter P. I don’t like to just sit on the performance conversation. I love having a potential conversation. It’s a fun conversation. So instead of us saying, hey, your performance needs to improve. It’s us going.

Hey, can I tell you something? I really see your potential. I see something in you. I see you being able to lead because there’s two kinds of mindsets. There’s an hourly mindset. I hope I get a dollar more an hour. And there’s salary mindset. Somebody that has enough confidence to be able to walk into a room and say, hey, you need to start paying me $20,000 more. It’s a completely different mindset.

To be able to look somebody in the eye and go, I think you could run this place someday. And for you to be able to do that, here’s the gap between where you are and where I think you could be. And I’m in your life to help you reach your ceiling. And sometimes to lift the ceiling on what you can do. It’s a completely different conversation than get your act together and your performance needs to improve. And so I love.

Having conversations with people about their potential. And here’s the interesting thing. They may not care about the work that I need them to do, but I’ve rarely met a person that didn’t care about their own potential. You start to see the wheels turning to go, okay, here are the steps of what you can become and here’s what I see and I’m gonna give you a shot. I believe in you. 

Ryan Leak: Do you know what employees can do when they’re believed in by their leader? When a leader is able to look them in the eyes and say, this is what I see in you. Most people that even work for great leaders are still trying to figure out where they stand with that leader and what they see in them. So when it comes to getting people to care, I don’t think it’s that you’re trying to get them to care about their their drop. I think you’re trying to meet them where they’re at what they already care about, which is ultimately their destiny. And so showing how, hey, how this is part of where you’re going. You give it your best tier, we’ll determine if you can handle what’s there. And so I think that those are some things that can help somebody, I wouldn’t say help them care more, but I think it is something.

Something powerful and inspiring when someone is showing up to their job every single day, consumed with not, how am I doing today? But consumed with, you know what? I want to reach my potential. And oh, by the way, because this leader saw something in me, I feel like I don’t want to disappoint them. Like they believe in me. Maybe they believe in me more than I believe in me. And so today I’m going to try and live up.

Ryan Leak: To the potential that they see. Let’s just see if they’re wrong. So it’s just a completely different mindset that I think you can equip employees with when you start having potential conversations instead of just performance conversations.

Dr. Jessica Kriegel: Amen, because that’s what culture partners, I sold my business to culture partners in 2021 because that’s what they were about. Their mission, their why is our why is to unleash the power of culture, to inspire people and businesses to reach their full potential. It’s not to drive maximum performance, although that’s what ends up happening as an outcome of reaching your full potential. So, I love that. Okay, so we have a couple callers. Let’s…

Ryan Leak: Yeah. Yeah. Yeah.

Ryan Leak: Sure. Absolutely.

Dr. Jessica Kriegel: Go to them and see what questions they have for you.

Dr. Jessica Kriegel: Wonderful. What’s your question?

Ryan Leak: I think that the way that you overcome perfectionism is, you’re not looking for perfect, you’re just trying to look for better. If you’re waiting, perfect is unrealistic. It’s just unrealistic. If you’re waiting for it to be perfect, well, you’ll never do anything. You’ll never get started. But here’s what I tell people all the time. You cannot improve the thing you refuse to start.

Your podcast can’t get better if you don’t record episode one. Your book can’t get better if you don’t at least put together an outline. Like you got to get started. I’m working on a book right now called how to work with complicated people. Where the outline was two months ago versus where it is today. It’s almost a completely different book, but we’re able to make it better every single day because we got started. It’s not perfect. I don’t know that it ever will be.

No, no, it drives me crazy is being the author of two best selling books that have typos in them drive me absolutely insane.

Dr. Jessica Kriegel: Do they really both?

Ryan Leak: Both. And I found both of them while reading the audio book, and I was infuriated.

Dr. Jessica Kriegel: Thanks for watching!

Dr. Jessica Kriegel: Hahaha

Ryan Leak: I was infuriated and at the same time I was liberated.

Because funny thing is, is most people aren’t going to read my book out loud. And these typos are very, very difficult to catch unless you’re talking out loud. Because 35 people who are proofreading all read these books and they didn’t catch it. And neither did I. I’m not mad at them. But once I was reading it out loud, me and the audio engineer were like, that doesn’t make any sense at all.

Dr. Jessica Kriegel: Yeah.

Ryan Leak: And he’s looking at me like, but you’re an idiot. Put it in a book. I’m like, I know. So, but it’s liberating. It’s, apparently, this is what I’ve heard, to hit best sellers list.

Your book doesn’t have to be perfect. I didn’t know that.

I didn’t know that. And here’s the funny thing, in Chasing Failure, I talk about typos. And, no, I talk about typos and I said, hey, and don’t worry if you find a couple of typos. And I said it as a joke in the book.

Dr. Jessica Kriegel: Chasing failure.

Dr. Jessica Kriegel: Do you talk about typos where the typo is?

Dr. Jessica Kriegel: It’s almost like an Easter egg.

Ryan Leak: But now it’s like, it ain’t a joke. I meant it to be a joke, but now it’s a real thing because they’re a typo. So, yeah, you can’t perfect the thing you refuse to start. So I think it’s the focus, the focal point should be around getting started and progress every single day. And then I think one day you wake up with something that I think can add value to the world around you and it will, it’ll never be perfect.

Dr. Jessica Kriegel: I love it.

Ryan Leak: I sent a proposal off to someone the other day for, it was like a $50,000 proposal for a whole rebrand for the company in Rochester.

Ryan Leak: I got their name wrong on the front cover page. Yep, yep, yep. Her name is not Lauren, it’s Laura. And I knew that. And everywhere else, the name was correct. Everywhere else, the name was correct. But, you know, just that front page, the one she got was, that was a great first impression. It was awesome. I love it. But nope.

Dr. Jessica Kriegel: Did you get the deal?

Dr. Jessica Kriegel: Did you get the deal? Ha!

Ryan Leak: And nope, shocker, right? Who would have thought? But here’s the deal though. I mean, it was one of those things that one, we didn’t need, it was something brand new. It was actually out of the purview of what we normally do and we told them that. And so we had a great conversation about it and whatnot. But honestly, again, I infuriated it myself at first, but then liberated to go, you…

Dr. Jessica Kriegel: Amazing. Shocker! This guy.

Dr. Jessica Kriegel: Yeah.

Ryan Leak: You and I were talking about this the other day. We were like, hey, we don’t do video in our keynotes. Why? Because too many production people have screwed it up.

Well, how did we learn that? How did we learn that? You get burned on stage.

Dr. Jessica Kriegel: Been burned. Getting burned on stage and trying to tap dance through the audio video error. Brutal.

Ryan Leak: You, yes, it was brutal, but we got something that most speakers don’t have experience.

And so some people were like, dude, that was rough. I’m like, yeah, but I got the rough and you did it. And so the next time rough happens, I’ll be ready.

Dr. Jessica Kriegel: You know, it’s funny, I’m, people have, you know, I’ve had the kind of career or whatever life that a lot of people have spent. The question I get asked a lot is like, how do you do it all? How do you get it all done? Or how do you fit it all in or whatever? They’re trying to understand how I’m able to accomplish all the different types of things I’m working on at any given time or within one year. And the answer.

Ryan Leak: So. have that question for you too. Yeah.

Dr. Jessica Kriegel: Yeah, it’s like you just keep doing the stuff and you see what happens. Like the example is we were in Mexico on vacation and I go to an AA meeting in Mexico that’s by the hotel and I sit down and this guy walks in with this amazing little black Labrador and he just is exuding love and I’m a black lab lady and I haven’t had a dog in many years and I just knew that dog was my dog the second it walked in.

Ryan Leak: Yeah. Yeah.

Dr. Jessica Kriegel: And I said, oh my goodness, I love this little nugget. What’s her name? What is going on with her? And he said, I just found her in the rainforest. Do you want her? I’m looking for her to have an owner. And I said, I fricking knew this was my dog. Yes, I want her. I totally want her. And then there’s the thought in my head, but wait a minute, can you actually make this work? How are you gonna get the dog back from Mexico? When are you gonna walk a dog, given how busy your schedule already is? You got a six-year-old and you live alone.

Ryan Leak: Yeah.

Dr. Jessica Kriegel: How are you gonna go for a walk with this dog when you’ve got the six-year-old dog? And I said, I’m not gonna worry about all of the what ifs. I’m just gonna start making progress on this dog thing. So I called Delta. Delta, can I get this dog back? How do I transport? What paperwork do I need? What size requirements? Anyway, I just kept going forward. And then in the end of the day, I couldn’t bring the dog to Sacramento because Delta didn’t allow it. He was too big, whatever.

Ryan Leak: Yeah.

Dr. Jessica Kriegel: So then I figured, you know, my mantra is that I’m responsible for the effort and God’s responsible for the outcome. So I made the effort, I just keep making the effort. And when something fails, it wasn’t meant to be. I get back home and I’m like, well, maybe I’ll get another dog. I’m thinking about it. The guy from the meeting texts and he’s like, seeing you with that dog inspired me so much. I have a friend who’s flying Air Mexico, which does allow traveling dogs.

Ryan Leak: Yeah. Yeah.

Dr. Jessica Kriegel: To San Francisco in a couple of weeks, do you still want the dog? It’s like the dog came to me because of the effort, you know? So I don’t really worry about the outcomes. I just worry about the effort and then things keep happening. And there are a thousand things that I started that didn’t get finished, you know, that no one knows about. And maybe that’s something. Okay, let’s go to the last caller for you.

Ryan Leak: Yeah. Yeah. Yeah. 100%.

Dr. Jessica Kriegel: Wonderful, Debbie, what is your question?

Ryan Leak: Well, I love Debbie. Debbie is a dear friend, one of the sweetest people you’re ever going to meet in life. And she has a very, very phenomenal question because one of the things that we have is a podcast called Followership. It’s the other side of leadership. It’s this idea that regardless of the kind of leader that you have, whether they are amazing, just good, average, bad.

You name it, the kind of leader that you have does not have to determine the kind of follower that you can be. Some people think, I work in a toxic environment, therefore I must be toxic. Well, no, I actually think that’s really bad math. I actually think you have a lot of power over who you’re going to be, and I actually think a person can have great influence on a team regardless of their position in an organization. I think one of the ways that you can…

Have influence and really stand out is one generosity. And I’m not talking about just giving money. Talking about somebody that is truly willing to go above and beyond for others. It is actually pretty rare. You can be generous in how much you care about that team. You’d be surprised how much influence you’ll have in somebody’s life just because you care about.

Ryan Leak: With saying, hey, let me tell you how I first encountered Ryan. He called me, no agenda, just to see if there’s anything he could do for me.

Uh, you may be the 20th person this year that has said, Hey, right. You know, you’re the only person that does that. Just the only person in my world that calls. I’m like, what’s up? I’m like, nothing. How are you? What do you mean? How am I? What do you, what do you, what do you do? Why? Because most of us have so many, um, relationships with agendas. And so it’s actually pretty rare for you to have.

But doesn’t have an agenda. So you’re just being nice, you’re just being generous, you’re just being kind. You do that in your organization. You’d be surprised by the influence that you have. Do that, be consistent in that for three, four years. You’d be surprised where you find yourself just from just showing uncommon care in your organization. That decides to be a person that doesn’t just ask people how they’re doing. Because 99% of people are gonna lie when you ask them how they’re doing. Because when you say, hey, how you doing? Good.

It’s your natural response. Good. Hey, how’s your daughter doing? She’s good. You say it before you even think about it. Be the kind of person that says, hey, how you really doing?

Ryan Leak: Huh, they don’t even know the answer until you make them actually go search for the answer. And now you have a real conversation. Now you’re being very, very intentional. Trust me, you do that long enough, you’d be surprised the amount of influence that you have in an organization and on a team and to be able to make really, really great changes just from being just a little bit different. And one of the phrases I love to use is, you only have to be a little kind to make a big difference.

Because most people don’t experience kindness on a daily basis. It’s pretty rare for them. And so some people think, I gotta go do this massive gesture to make a difference in somebody’s life. I’m like, actually no, I actually think you should get a little one because most people don’t experience a thoughtful card. Most people get a text on their birthday, happy birthday. I like to send videos. Like you’re a close friend of mine, hey, you get a video. And I spend a minute telling that friend what.

What they mean to me and the value they add to my life. I will say nine times out of 10 when I send a video, what they write back is, I got a lot of texts today. You’re the only video actor.

So I’m not patting my back, I’m just saying, I have figured out how to be different. But at the same time, it’s pretty normal in my world, but I think if you wanna continue to have influence, I think regardless of where you’re at on the totem pole, I think showing uncommon care, being a person that is truly generous, I think you could make a huge difference in your world and in your.

Dr. Jessica Kriegel: I have one more question before I ask you the last question. And I just, because I wanna share one of the most profound conversations I’ve ever had with you was a conversation about faith, which a lot of our conversations are about. And I was asking you how to, I asked you what your denomination was. I’ve still not found, I don’t wanna be spiritual, not religious. I wanna be religious, not just spiritual, okay?

Ryan Leak: Sure. Okay. Sure. Yeah.

Dr. Jessica Kriegel: But I can’t find the religion that fits for me because everyone says they’re the one, which is a fundamental misunderstanding of the unknowing that we must have as mere humans that aligns with my beliefs. So I keep searching, you know, I keep going to new churches all the time. And I asked you about this and you said, the first thing you have to do is figure out your fundamentals.

Ryan Leak: Uh-huh. Sure. Okay.

Dr. Jessica Kriegel: Can you share what your fundamentals are?

Ryan Leak: Yeah, that’s a great question. You know, I think when I say fundamentals, I think, you know, what are gonna be some of your fundamental beliefs about God, about the world, about how to treat people? I think you need a fundamental.

Ryan Leak: Steer you in a lot of different directions. And so I think having those ground rules, if you will, for your life to be able to say, okay, these are going to be some of my, we just use the word fundamentals, I really think their personal values is really what it comes down to, to be able to wake up in the morning.

Ryan Leak: God is a loving God, he’s not trying to punish me today. He’s a loving God, I can start there. I’m forgiven, I’m not gonna try and earn something from God today. Am I gonna get in God’s graces because we’re philanthropic? No, I’m in God’s graces because of what Jesus Christ has done for me. And so why is that a fundamental for me? It means every single day I don’t have to prove myself to anybody. And also I try not to use the phrase, I don’t care what people think about me. 

No, I actually do. In fact, when you say I don’t care what people think about me, you’re actually disconnecting from the people that actually care about you. And so, no, you do have value. What you say does actually impact me. But at the same time, what you have to say about me doesn’t control me. That’s the difference. And so, I think fundamentally, I wake up going, I don’t have anything to prove because God has given me everything that I need, something else that’s fundamental for me.

Ryan Leak: a high level of contentment. Contentment is like a cousin of generosity, I think. I think you need contentment to be able to be generous because I think you need to be in a place where you can say, I have enough.

I’m successful enough. I have enough because sometimes we will attach our identity to how much we get. But when you get to a place where you go, I have enough. I have enough influence, I have enough followers, enough money, I have enough accolades. I have enough. And yet I’m still, I’m hungry for more, but not for validation. I’m hungry for more because I love being able to impact.

A lot of people and God’s given me the ability to do so. Some other fundamentals around, you know, just how you treat people. I think that one of the questions I ask clients on pre-event calls is, who’s the best speaker you’ve ever had and why? And let me forget, I was getting ready to speak for State Farm and they said Doc Rivers, Coach Doc Rivers. I used to be a coach in the NBA.

A former coach of the year and be a champion. I said, yeah, you know, Doc Rivers, he’s known for these motivational speeches. So it’s like, yeah, of course you would say that. And they said, but let me tell you why he was their favorite speaker of all time. He says because he was agendaless, which I don’t even know that that’s a word, but they used it. He said he was agendaless. He was truly there just to serve us. He didn’t have an agenda and we all felt it.

Dr. Jessica Kriegel: Hmm.

Ryan Leak: And I thought that day, I said, I think that’s the story I want people to tell about me. Agenda-less. And he isn’t looking over my shoulder to see who else is in the room. No, he’s just looking at my eyes. And I’m important, and I’m VIP to Ryan. And…

Ryan Leak: I think that’s something that’s, when you have that kind of fundamental of like people aren’t pawns on a chessboard to you, you’re not making moves, but you’re genuinely interested in people and serving them and helping them. When our mutual agent told me about a new and up and coming speaker, and I immediately said to him, I said, hey, feel free to put us in an email.

I’d love to help him win in any way that I possibly can. And he’s like, and this is Don Jenkins, but he goes, he goes, you do that?

Ryan Leak: Sure. Like, what, like, and Don didn’t infer this, but I think this is inferred in our business. But that’s your competition.

Ryan Leak: A lot of events happening all around the world.

Ryan Leak: I hope they choose him. I hope they choose you. Like, we were at the same event. It wasn’t like that, well, is it gonna be Jessica or is it gonna be Ryan? Guess what, it was both. You’d be surprised how much space there is in the world. And so I’m not saying I’ve got no insecurity. I’m not saying that, you know, I’m always in just this generous spirit, but I just think fundamentally, just my overall belief system that-

Hey, keep giving, keep helping other people win.

Ryan Leak: You will eventually reap what you sow. So those are a few fundamentals for me.

Ryan Leak: Sure.

Dr. Jessica Kriegel: Okay, so thank you for agreeing to do this podcast with me. This is the first one I’ve recorded where I wanna go back and listen to it again because you dropped so many nuggets.

Ryan Leak: Of course.

Dr. Jessica Kriegel: I was like, I gotta write that down. It’s fantastic. So my last question is my favorite question, which is what is one thing that you don’t get asked in these podcasts and the interviews you do at the keynotes that you wish more people would ask you?

Ryan Leak: So funny.

Ryan Leak: Uh, what does it cost to be you?

Dr. Jessica Kriegel: Hmm. What does it cost to be you?

Ryan Leak: Yeah, I think that there is a perception of what we do that is sexy, that feels like overnight something happened. But I think I get so many messages about speaking, how to break into the industry, and how do you get connected with the industry.

But I don’t think people are asking the right question. I think they need to be asking more people in a position like yours, like, hey, what price did you pay to be where you are? What?

Dr. Jessica Kriegel: Yeah.

Ryan Leak: What did that mean for your motherhood for you to be where you are? What did that not just cost you? What did that cost your daughter?

I don’t think people are asking the right question. That’s the question I wish people asked more of like, hey, what did it cost your wife last year? What does it cost your children? What does it, what does it, what does it cost to make custom keynotes for organizations four days before the event? Like people just think, oh, you just do it. It’s like, no, that’s.

Dr. Jessica Kriegel: Mm-hmm.

Ryan Leak: That’s not it. I think successful people in general make their craft look easy. But it’s never easy. And at the same time, you’re not pulling out a violin that say, hey, woe is me. But I think for people that are aspiring to take things to the next level, sometimes I do think that they’re asking the wrong questions. They want to know nuts and bolts and how do I do this?

I think to take a quote from a mentor of mine, John Maxwell, he said, some of the best leaders and speakers and authors in the world will never know about because it was just too expensive and it was a cost they weren’t willing to pay.

Dr. Jessica Kriegel: Beautiful. Thank you, Ryan. It has been an absolute joy and such a privilege that you share your nuggets of wisdom with us today. And I am so grateful that you are my friend. Thank you for being you.

Ryan Leak: My pleasure. Absolutely.

Ryan Leak: Yes, I’m grateful that you’re my friend as well. It was a pleasure being on your podcast.

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