The Learning Leader Show With Ryan Hawk
The Learning Leader Show With Ryan Hawk

The Learning Leader Show With Ryan Hawk

Ryan Hawk

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Leaders are learners. The best leaders never stop working to make themselves better. The Learning Leader Show Is series of conversations with the world's most thoughtful leaders. Entrepreneurs, CEO's, World-Class Athletes, Coaches, Best-Selling Authors, and much more.

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670: Mike Deegan - Building a Championship Culture, Mudita (Joy for Others), Systems Thinking, Curiosity = Love, Getting Out of a Slump, and The DNA of Great Teams
JAN 12, 2026
670: Mike Deegan - Building a Championship Culture, Mudita (Joy for Others), Systems Thinking, Curiosity = Love, Getting Out of a Slump, and The DNA of Great Teams
Go to www.LearningLeader.com to learn more... This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My Guest: Mike Deegan just led Denison University Baseball to their first College World Series appearance in program history. He's been named Coach of the Year in back-to-back years and is the all-time winningest coach in school history. In this conversation, Mike shares how he uses Mudita to build culture, how to help people get out of slumps, and why discipline and consistency are superpowers. Key Learnings (in Mike's words) Mudita is a vicarious joy. Can I be happy for another's success as if it's my own? To me, that is like the secret sauce of life. Obviously, in a sports team, not everyone can be the star. One of the biggest misconceptions is that the star rotates. Yeah, you need a superstar to compete at the highest levels, but to win, you're going to need pinch runners, you're going to need the guy laying a big block. It's going to take everyone. It's really celebrating everyone's contribution. In recruiting, I ask parents: Can you be happy for another kid's success as if it's your own? If your neighbor gets a new car, are you happy for them? Or do you say, "Oh, I wish. I bet his parents bought that for him." There are just different ways to show up for people, where you can just have joy. By pouring yourself into others, especially in sports, I think it frees you up to perform your best. Envy is a natural feeling. I don't want anyone to feel that envy from me. I think what we're saying is that envy is a natural feeling. Wanting to do great yourself, those are very natural, and I want people to live in that space. But can we just stop it and be a little bit more intentional and just celebrate what other people are doing well? Spot the good first. As a consultant, there are two ways you can do things. One is to find the negative, and that's really easy to do. But I try to go and spot the good first. There's plenty of time to nitpick later on. Find some opportunities to help people grow. People love to talk about themselves. My wife is very quiet, a great listener, and people love her. She has a million best friends, and no one knows it because she doesn't talk a whole lot. She just listens. If you can just listen and get people to talk about what they're passionate about, it's a life secret. You can tell when someone's really passionate about what they're doing, and you can tell when they're on the fence because they speed up when they talk, they get a little excited. Curiosity is a great way to show love. If you approach it from envy, we don't unpack the cool story. But if you lead with curiosity and not envy, it unpacks everything. I do think it takes a level of self-awareness and comfort in your own skin. How to build self-awareness: Read, write, and get around wise people. If you read a decent amount, if you write (and that was my forcing function, to actually write and put thought to paper), and then get around wise people and just have conversations, I think you'll start building out the awareness of who you are and what you value. A systems thinker builds frameworks that outlast individuals. It's someone who can build out frameworks that are built to put people and the organization in the best spot to win and be successful. It's a framework that outlasts individuals. Coaches may leave or players may leave, but if you have a system built out that it can sustain losing certain individuals, because things are cranking and you can repeat the work. You can do iterations and quickly test if you're getting closer or further from your goals. I almost try to talk people out of coming here. The most underrated thing in our recruiting is when they sit with me, I almost try to talk people out of coming here. I'll say, "Hey, what's the main driver?" If they say playing time, I'm like, "Hey, that's great. That's an awesome goal, but I wouldn't come here for that. We're going to play our best players. But that's not why you come to Denison. You come to be a part of something bigger than yourself, and there are all these other places where you're going to have a much better shot at that." I'm always listening in on what they value and trying to challenge it. Almost get people to self-select out. The better your culture is, you can take chances on people. It's like Randy Moss and the New England Patriots. Tom Brady was an alpha, and you could bring people in and take a risk and see if they can conform to the culture a little bit. When you have things in place, our locker room was phenomenal. People would say, "Hey, I don't know, this kid has some red flags." I'm like, "Red flags, like he's a serial killer? Or like red flag,s like he's super competitive?" The locker room would take care of a lot of that. If there's something built out that you feel pretty strongly about, I think you can take in some of these high-risk, high-reward people because they can't damage the culture like you would think they can. Early on in that tenure, I was very, very careful with this. But now we can take some chances on people if the DNA is right. The lack of seriousness pushed people out. When I took over, I'm the opposite of the guy I played for. And every time someone quit, I would just say thank you. And I meant that too because we were going in a certain direction. There was talent. It needed more seriousness. We had enough talent that it was going to allow us to compete at a conference level. I think it's amazing when you can just put boundaries and guardrails and point people in the right direction. We just provided a little structure, a little discipline. The DNA of great teams: Roles, sacrifice, discipline, leadership, joy. Everyone has a role and to beat objective expectations. When good meets good, you have got to understand that every role is essential to the cause. Status goes away. Second, we're in this together. There's no prima donna. I think that's what happens with championship teams. For us to compete on a national level, our guys do miss out on a lot. Grades may suffer. There are trade-offs with this thing. Then I hear discipline. Discipline and consistency is a superpower. The people that I see that really excel in the professional baseball world they seem to have a maturity about them at a much younger age. And that comes with discipline and consistency. Then leadership. There's going to be someone that's navigating the ship. In my beautiful world, it would be where that person's not an egomaniac. They're not in front. They're just waiting for everyone to get out. The last thing is joy. People tend to enjoy what they're doing. They do it with a smile on their face. "Don't hire for when you think times are good. Hire for the person you wanna be around when times are bad because they're coming." An example of a great team outside of sports: The Chilean miners found roles quickly and stuck together. They had food for two days but rationed it out. They had a spiritual leader, medical guy, someone to keep them on task. Everyone had a specific role and they performed it. How you talk to your teammates is how you should talk to yourself. I had a conversation with a kid that I really admire on our team and I said, "Hey man, I never hear you talk to your teammates like you talk to yourself. Give yourself some grace." Being really hard on yourself can also be a cop out because there are ways to channel that. Sometimes people will say "I'm a perfectionist, or that's just who I am." Come on man. A perfectionist to me, they put an insane amount of work to earn the right to be. I think we use that term pretty lightly sometimes. Confidence is built through evidence. Ryan's self-talk before a keynote sounds like this, "What an opportunity to create some evidence." How to help a hitter get out of a slump: Simplify and control the controllables. When a player's in a slump, they're probably working harder than they've ever worked in their life. But I think it's almost like they're working aimlessly. So what I try to do is simplify. I had a hitter once, he's trying everything. I gave him one swing thought for two weeks. Just get the barrel to the ball. Don't worry about launch angle, don't worry about exit velo. Can you just put good wood on the ball? We're going to control what we can control. And slowly you start seeing some results and that evidence starts compounding and you get your mojo back. You gotta be intentional with your energy before high performance. As a coach, how you show up is going to be really, really important. I saw Texas A&M's coach say you have to be the opposite of what the moment requires. While everyone's excited, you need to be the calm. And then when the proverbial is hitting the fan, you have to be the one with optimism. Getting yourself in the right mental frame to handle high performance is required of a coach and a leader. Baseball teaches you to stay calm for three hours. You don't play baseball at 130 heartbeat. It's more of Can you get that thing down? And anything I do to increase it myself, I'm going against what it takes to be a successful player. People can think baseball is boring, but what you're seeing is people trying to stay calm for three hours. Does that intensity actually lead to results? It's just basic stoicism. Baseball is the ultimate controlling what you can control and releasing what you can't. I don't know if this next ball's coming to me, but what do I do now? I can control my breathing. I control my first pitch prep step. What can you control? And I would challenge you to think, does that intensity or that emotion, does it actually lead to results or not? If it's helping you be the best version of yourself, go ahead and do it. But sometimes that overstimulation, that over emotion, it's probably just putting a lot of anxiety on your people. Just regulate, stay calm and execute. What does the team need from you right now? I think a good analogy is a cornerman in boxing. My dad used to always say, Watch a cornerman in boxing because some people you gotta smack. Some people say, "Come on champ. You're the best. You're the best. You're the best." When you're walking out there, you're trying to think, what does the team need from you right now? What message? If I'm a mirror, what do they need to see? Do they need to see calm, they need to see reassurance? Are we playing a little timid and scared? And maybe you're trying to jolt them a little bit with some energy and some choice words. There's an intentionality to it. You're trying to speak some stuff into existence, even if you're making stuff up. You acknowledge it, and then you also try to point them in a direction for improvement. Life throws haymakers at you all the time. I think that's the greatest gift that we can give people through sports. Most of us experience adversity along the way. It's this unique ability to just keep moving. You reflect, you try to get better. You give yourself some grace, you move on. You just keep working through that process. As simple as it may sound to us, I don't think many people can get there. "Setbacks are temporary. I bounce back quickly." I write this down in my lineup card. You're creating evidence. It's something very simple, but I'm going to take a punch and I'll bounce back quickly. I think those are just good reminders in life. This happens. We're going to respond. Reflection Questions Mike practices Mudita by being genuinely happy for others' success without envy. Think of someone in your life who recently had a big win (promotion, new house, achievement). Were you genuinely happy for them, or did envy creep in? What would it look like to celebrate them more fully? He says "Don't hire for when you think times are good. Hire for the person you wanna be around when times are bad." Who on your current team would you want in the foxhole with you during a crisis, and what qualities make them that person? Mike asks himself before big moments: "What does the team need from me right now?" rather than just reacting emotionally. Think about a high-pressure situation coming up in your life. What will your team/family/colleagues need from you in that moment, and how can you prepare to show up that way? More Learning #217 - JJ Reddick: You've Never Arrived, You're Always Becoming #281 - George Raveling: Eight Decades of Wisdom #509 - Buzz Williams: The 9 Daily Disciplines Audio Timestamps: 02:11 Implementing Mudita in Teams 06:22 Curiosity and Spotting the Good 14:54 Recruiting and Hiring Philosophy 20:36 Building a Winning Culture 24:46 DNA of Great Teams 27:55 The Importance of Team Sacrifice 28:53 Leadership and Joy in Tough Times 29:42 Handling Adversity in Sports 31:06 The Role of Self-Talk in Performance 36:52 Staying Calm Under Pressure 42:26 Lessons from Sports for Life 46:12 The Value of Resilience and Bouncing Back 48:29 EOPC
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51 MIN
669: Oz Pearlman (Oz The Mentalist) - Overcoming Rejection, Getting the Reps, Always Following Up, Living with Gratitude, America's Got Talent, The Curiosity of Steven Spielberg, and Making Others Feel Seen
JAN 5, 2026
669: Oz Pearlman (Oz The Mentalist) - Overcoming Rejection, Getting the Reps, Always Following Up, Living with Gratitude, America's Got Talent, The Curiosity of Steven Spielberg, and Making Others Feel Seen
Go to www.LearningLeader.com for world-class notes This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: Oz Pearlman is the greatest mentalist in the world. After leaving Wall Street to pursue his craft full-time, he's performed for Steven Spielberg's family, for Nobel laureates, and Fortune 500 CEOs. He ran a 2:23 marathon and holds the record for most laps around Central Park in a single day. With five kids and 250+ performances a year, Oz has mastered the art of reading people and understanding what separates good from world-class. Key Learnings (In Oz's words) Doug Anderson is the magician who got me into magic. When I was 13 years old, I went on a cruise with my parents. I got pulled up on stage and took part in a magic trick. (The sponge balls) After the trick, my dad and I started creating theories on how the trick worked. The people in every industry who make it to the top are the ones who are kind and respectful to others. As soon as you stop thinking that you can learn from others, you start dying. What is the recipe for success? It's getting through the tough times. When I walked up to someone at a restaurant, and I'm 14, and I have a very fragile ego, after three tables in a row at differing levels of rudeness go by, "Dude, get outta here, man. Like, I don't wanna see this," it hurts. That's a painful thing to experience. I had to learn a defense mechanism very quickly because carrying that pain, pain turns into anger. When I get to the next table, I'm angry at the next group, even though they haven't done anything wrong to me. I realized to get my goal, I needed tougher, thicker skin. Deflect the rejection onto someone else. Create separation between you and rejection. I created what I would call an agent in my own mind. When you're in showbiz, the conversations you don't wanna have, your agent has for you. I'm a 14-year-old doing restaurants. I don't have an agent, so here's what I decided. When they don't like me, they don't know me. They don't know Oz Pearlman. They know this guy Oz the magician, who walked up to them. Maybe my tricks aren't good enough. Maybe my approach wasn't good enough. Maybe they had a bad day at work or their kid's sick. I made it less about me, and I was able to deflect all of that pain and hurt to this other person. The fear of rejection is worse than the rejection itself. Once you experience rejection a few times, it's not that bad. It's like dating. It's a numbers game. You'll probably not meet your spouse on the first try. You gotta meet a whole lot of other people to realize what you like best in the person that hopefully ends up spending your life with. "Never let someone else be in charge of your destiny." When I do a gig, I don't wait for someone to go, "Oh man, that'd be great. Let me get your business card." I go, "Amazing. Let me get your number and your info. I'll have someone from my team call you." My team is you, me, myself, and I. There's no team. But it sounds fancier. Fake it till you make it. Branding is so important. When I went on America's Got Talent, I made a conscious decision to separate myself from the guy from the year before. (Matt Franco) He won. I thought we were too similar. I had to do something unique or do something better than anyone else. That's when I branded myself as a mentalist and not a magician. Mentalism is much harder than magic to practice. Magic can be practiced in front of a mirror until you get almost perfect at a trick. Mentalism is near impossible to practice at home without an audience. It's like comedy. You can't tell jokes to a mirror and find out if they're funny. You need the audience to do it. Charm takes the sting out of so many things in life. It allows you to win people over quickly. What is charm? Just the ability to smile, to make someone laugh, to be vulnerable in a certain moment. That's a skill that's developed, and if you study it well, you can develop it quicker because everyone thinks it's natural. What I've learned from comedians: It's the purest form of entertainment that exists. You, the audience, and a microphone. I think you start to get a feel for timing. Where to pause, what's funny, how to get people on your side. With a heckler, there's a very fine line between punching down and offending your audience versus having them on your side and laughing with you at someone as opposed to laughing at someone. I'm a slightly more exaggerated version of myself when performing. The volume is turned up a little. The charisma is turned up a little, the ability to joke around, but it's me. I think that resonates. Walking into a room smiling, having no hesitation, connecting with somebody, remembering their name, giving them a compliment. Such easy, low-hanging fruit, separates you from 90% of other people if you can do them consistently and effectively and genuinely. "That's why he's Steven Spielberg." The Steven Spielberg lesson changed how I see success. I did Spielberg's dad's 99th birthday. At the end of it, Steven beelines to me and I'm ready. I thought I'd get 30 seconds. He talked to me for upwards of 20 minutes. He just asked question after question after question. When I left it was like a blur. I didn't ask Steven Spielberg a single question about Jaws, Close Encounters. I had all these things I wanted to ask him. I'm like, man, I totally screwed that up. But over time, the lesson got through to me. It wasn't about me. It wasn't what I was gonna ask him. It was about him. It was learning what makes him tick. No matter who you become, if you can make the other person feel like they're a star when they meet you, they will always remember that memory. Try to deflect. If people ask you questions, answer, but ask them something about themselves back that no one's asked them. Make them feel seen and heard. Make them feel like they are the star of your movie as well. Little things add up to big things over time. If you were to ask my kids what do I ingrain in them all the time? Gratitude and being polite. One of my secrets to success has always been being very polite. "Please, thank you. Always." Write a thank-you note. When I was doing bar mitzvahs, birthday parties, I realized early on, when people are throwing a party, it's very stressful. The person hosting doesn't always have the greatest time. They're so worried about everyone else. Create memorable moments. I would take a selfie with the bar mitzvah kid. I found this online service where I could instantly upload the photo. I would always give a compliment that was specific. I'd send these cards to them on Monday. The parties are usually on Saturdays. It would get there Tuesday or Wednesday. To this day, 15 to 20 years later, I'll get emails when I'm on TV from people being like, "I just dug up this card from 17 years ago. You were at Benjamin's Bar Mitzvah, and now he's 30 and has a kid of his own." Takes notes | Write everything down. In today's day and age, there's a power in the human touch that still exists. Take notes, write stuff down. I'll leave a gig, I'll write some stuff down, I'll remember it. If I run into that person again in a month, in a year, in five years, I can literally look at my phone. It's literally like a mentalism trick to reveal that information to people even though they gave it to you already, because it shows you took the time. Some of the biggest things I've ever landed backtrack to small moments. ESPN, the thing that brought us together can backtrack to a Bar Mitzvah 18 years ago where I first met Adam Schefter. The first seed was planted, and I had to keep watering it, watering it, watering it. Small plant, small plant, until it grew into this thing. Now look at all the things that came from all the things I've done with ESPN, where Adam Schefter originated them. You are interviewing for your next job every single day. You have no idea who might be in the audience. You have no idea, but you give it your all every single time. One time, Adam Schefter was in the audience. Intelligent people are often the easiest to fool. When intelligent people watch what I do, they're confident in their ability to figure it out. They think they're smarter than the average person, so they start looking for solutions. But that overconfidence creates blind spots. They're so focused on being right about how they think it's done that they miss what's actually happening. The more you think you know, the more vulnerable you become to being fooled because you're operating from assumptions rather than staying open to all possibilities. Reflection Questions Oz created an "agent in his mind" to deflect rejection away from his core self, making it about "Oz the magician" rather than Oz the person. What mental separation could you create to handle rejection or criticism more effectively in your professional life? Oz emphasizes that intelligent people are often the easiest to fool because they're confident in their ability to figure things out. In what areas of your life or work might overconfidence be blinding you to what's actually happening? Oz sends handwritten notes with specific compliments and a selfie to everyone he performs for. What's one relationship in your network right now that could be strengthened with this level of intentional follow-up, and what specific compliment could you give that person? More Learning #525 - Frank Slootman: Hypergrowth Leadership #540 - Alex Hormozi: Let Go of the Need of Approval #510 - Ramit Sethi: Live Your Rich Life Audio Timestamps 02:43 Oz's Career 04:48 The Art of Mentalism and Magic 08:22 Early Career and Overcoming Rejection 17:45 Branding and Success Strategies 22:59 Authenticity and Charm 27:25 Building Trust Through Honesty 27:53 Developing Genuine Confidence 28:36 The Power of Preparation 29:22 Learning from Failure 31:24 Connecting with Influential People 34:27 The Importance of Politeness and Gratitude 37:05 The Art of Follow-Up 42:27 Handling Nerves and Anxiety 43:23 The Magic of Mentalism on Ryan 51:55 EOPC
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54 MIN
668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel
DEC 29, 2025
668: Brian Kelly (The Points Guy) - Building a Media Empire, Crafting a Big Vision, Relentless Leaders, Hiring Well, Scaling Up, & How To Win at Travel
Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Brian Kelly is the founder of The Points Guy, which he built from a side hustle blog into a travel media empire that he sold for $28 million. At 42, he's now an angel investor in 15+ companies, including Bilt (valued at $11 billion). In this conversation, he shares lessons on manifestation, selling too early, building yourself into the brand, and why vulnerability beats wins in interviews. Key Learnings (in Brian's words) In 1995, I was 12 years old, and I was great with computers, so I started booking all of my dad's travel for work. He'd pay me $10 per booking. Then it turned into points, when my dad showed me all the American and US Air miles he had. "If you can figure out how to use all of them, we can go on a family trip." And the rest is history. That was my first real, oh wait, this points thing is amazing. Points were a way for us to live a fabulous lifestyle. I grew up thinking we were poor, but I really wanted to live a fabulous life. My parents were very humble and did not spend money lavishly. For me I always wanted to travel. When I was a kid, I would spin the globe and be like, This is where I'm going. I would actually research Oman. Somehow genetically, I got this gene of I need to be rich and travel the world. I used to call Mercedes, get all of their glossy pamphlets for all their new cars, and I would cut them out and stick them on my wall. Manifesting alone won't make you wealthy, but visioning helps. I do believe being able to visualize what it looks like and taste it and get close to it helps you take the smaller steps to actually achieve it. When I think of my investments, I actually envision what they're gonna be. I envision that they're multi-billion-dollar companies. I believe it unlocks a level of pushing you to reach these mini steps that you can't see throughout the process. I started The Points Guy in 2010, but there were already Titan bloggers. I for sure felt imposter syndrome, but I saw that what they lacked was creativity. Points and miles are very clinical. Very few people were translating that for an audience. I knew I had an opportunity. I'm in my twenties, living in New York City. I'm gonna explain what everyday people need to know. Building a media brand became my moat. No one else in the points world was doing media. Doing media's frightening. While it was scary going on TV the first couple times (I almost fainted), I knew that each time I did it, I got better. That was the moat I would build. I would build The Points Guy into a brand more so than any of the others who had come before me. I saw from the beginning to double and triple down on that strategy of building something that's more than just a blog, but a lifestyle that people want to achieve. "I made a million bucks in my first six months of just blogging, but using affiliate links." In 2011, within six months of learning about affiliate marketing, I made six figures a month using the credit card links in my blog. I was still working at Morgan Stanley. My mom was like, this sounds too good to be true. You can't leave Morgan Stanley. I was making like $300,000 a month in affiliate. Meanwhile, at Morgan Stanley, my salary is $70,000 a year. But it didn't pay right away. My parents actually lent me $10,000 just to pay my rent. I remember where I was in Madrid when that first Chase deposit of $490,000 hit from months of back pay on the blog. I sold for $28 million because I thought the industry would collapse. When Bankrate offered me $28 million in May 2012, I kind of had this negative mindset over where the industry was going. About a hundred blogs started when people knew they could make money on affiliates. Most bloggers have zero business sense. They were writing stuff like, "Cancel your Amex, cancel your Chase, cancel, cancel. Then get new cards." I saw this really bad business sense, very shortsighted greediness. I'm watching this thinking they're gonna pull the rug. Do I regret selling? Yes, the company is way more than what I sold it for. But at the time, you always have to remember what the landscape was. We're coming out of the recession. There were still a lot of weak indicators. Building myself into the brand gave me leverage. I had a three and a half year earnout. Over that time, the business really started to grow, but then I realized, well, I am also the business. So, the more press I did, when I negotiated with that parent company to stay on, they paid me a lot of money and still a cut of the business to grow it as CEO. It's kind of crazy to think 13 years after selling, I'm still here. But because I built myself as a core part of the business as The Points Guy, I've been able to stay on with less risk, getting paid well to do what I love. I'm more of the brand visionary, the consumer person. I'm very much an ideas person. When we're speaking with our longtime clients or pitching new ones, that's really where my special sauce is used and not in the day-to-day. People are not mind readers. In 2020, I had this breakdown where I thought I would actually leave. I went to the owners, and I was like, I just can't do it anymore. They said, "Brian, we've been waiting for you to say that. You don't need to be CEO. We have plenty of smart people." It was this aha moment. I think in life we often think polar, black or white. That's advice I give to people. Whether it's your parent company, your boss, your mentor, people are not mind readers. While there is risk to leveling with someone and saying, "Hey, this role is just killing me," more often than not in my career, the more vulnerable I was, the more it turned out to be such a blessing. Check Your Spam Email Frequently: In 2011, I was featured in the New York Times, but the email came to my spam email. At that time, the narrative that points were dead, blackout dates, etc. I was the only blogger putting a positive spin on points. And I tried to do it in an informative and fun way. I'm 6'7", so putting my personal angle on my travel reviews had a huge impact on being the face of this industry. As a founder, I was a tough boss because it was so personal. If I look back at my time as CEO, I still took it very personally. I do take the integrity of this site. As we expand, we can't forego quality. In hindsight, I didn't highlight enough of the wins. I would focus too much on mistakes. That's advice I would give if I could do it all back over again, to just be much more positive reinforcement over negative. Founders need someone who can check them. You need to have someone around you, a leadership team, someone that can check you. I didn't have that for a very long time, and that's my fault. Making sure you have good people on your team that can be honest with you, and you create an environment of inviting that feedback and not freaking out when they give it to you, is important. I know I would be a much different CEO today if I did it again. Stop BSing in the interview process. Too many people take jobs not knowing what is going on whatsoever at the company. Far too many senior executives walk into positions and they're like, oh wait a minute. I like to be brutally honest in the interview process. Truth-telling is the beginning of having a great relationship because I want you to understand exactly what's in front of you. If you don't want to take it, that's so much better than hiring a senior exec and six months later, you just lost a year. Stop telling me the wins. In the interview process, stop telling me the wins because anyone can make their job look successful. "Oh, 200% ROI, this, that the other." In an interview, you're not gonna be able to fact-check any of this. We all know people can cherry-pick the data. It's really just diving deep into vulnerable moments about their leadership, the challenges as leaders they had with their teams. I'll tell them my challenges when I was CEO. I want people to be real and allow me to understand how they think, the type of leader they are. Charismatic people can trick you. The problem is that very charismatic people can trick you easily. I've been blinded by a great interview, especially when you're exhausted as a CEO and then someone's bantering with you. You're like, oh, that was fun. But I've hired plenty of people who are all talk. I don't want personality hires. I'm the personality. My engineering team, I really need people to ship updates. I still wake up in the middle of the night asking if my bills are paid. I still have imposter syndrome about "is this crazy what I've built?" It's for sure not about the car, but I will say investing in a home that's beautiful and makes you feel really good is important. For a long time, I was traveling a lot. I never put roots down, and I always felt like I was in transit. Now I have this beautiful farm with animals and horses in New Hope, Pennsylvania. It takes my blood pressure down immediately. Angel investing has basically become an addiction. In 2020, I opened up a space where I decided I wanted to have kids even though I was single, and also started investing and advising in relevant companies. The first one was Encore Jane, who was building Built, a credit card loyalty platform for renters. I'd always thought, how cool would it be to earn points on rent? I said, You're crazy, but if it does work, it'll be massive. Built is now at $11 billion valuation. I'll make more money now, probably on Built than I will at The Points Guy, which is wild to me. I have probably about 15 other companies I put my personal money in. I love it because I can help advise founders on everything I've done, and help open doors. Using that to build wealth has become an addiction. Relentlessness is what I see in leaders who sustain excellence. I am amazed at Encore's ability to push. If he's got 10 major things impacting his business, most CEOs will start with one or two, put the others on the back burner. He will relentlessly push for excellence. I don't wanna work for Encore, but to be in the room and strategize, every time I leave a meeting with him it keeps me fresh and active. Find mentors, not just companies. For recent college grads, find people, even at a company where you might not see your future. Find someone at that company that you connect with. If you're looking for a job, interview until you find that hiring manager that you feel is on an upward rise and that you can learn from. We often focus too much on the line of work or the company. Stop focusing on that and look at that manager or the CMO whose organization you would join. If they've done amazing things, get in right away and start networking. Put time on the CMO or CEO's calendar. Be bold. Every senior executive loves to see people come in with eagerness to learn. Show up and do extracurriculars at work. Go to the lunch and learn with the senior executive and actually get face time with them. Make sure they know your name. Those are the things that matter because when it comes time for compensation and reviews, the senior person may not work with you day-to-day, but they're like, oh yeah, that's the person I really like. They are a future leader. That's how you get ahead. Even if that boss leaves to another company, they might take you. Reflection Questions Brian says manifesting alone won't make you wealthy, but visioning what it looks like helps you take the smaller steps to achieve it. What specific vision do you have for your future that you could make more tangible (like his Mercedes pictures on the bedroom wall)? How might making it more concrete change your daily actions? He emphasizes that in interviews, he wants people to stop telling him the wins and instead dive deep into vulnerable moments about their leadership and challenges with their teams. If you were in an interview tomorrow, what's one vulnerable leadership moment you could share that would demonstrate how you think rather than just what you've accomplished? Brian realized he needed to tell his parent company, "I just can't do it anymore" as CEO, and they responded with relief, offering him a better role. What conversation are you avoiding right now because you assume the answer will be no, when the other person might actually be waiting for you to speak up? More Learning #525 - Frank Slootman: Hypergrowth Leadership #540 - Alex Hormozi: Let Go of the Need of Approval #510 - Ramit Sethi: Live Your Rich Life
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51 MIN
667: Nick Gray - How to Host World-Class Events, Why Leaders Need a Personal Website, Writing Like You Talk, Mastering Introductions, the Viral Tokyo Trip, & Adding Value Before Taking It
DEC 22, 2025
667: Nick Gray - How to Host World-Class Events, Why Leaders Need a Personal Website, Writing Like You Talk, Mastering Introductions, the Viral Tokyo Trip, & Adding Value Before Taking It
Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Nick Gray is the author of The Two-Hour Cocktail Party and founder of Museum Hack. He's mastered the art of hosting events that strengthen networks and build genuine connections. In this conversation, he shares practical systems for hosting gatherings, why every leader needs a personal website, and lessons learned from his viral blind date trip to Tokyo. The Learning Leader Show Key Learnings Two Great Ice Breaker Questions: What's a compliment that someone has given you that you've never forgotten about? If you could teach any class about a topic that you're an expert on, what would it be? The power of a network is real: As a leader, you're probably hiring people regularly or looking for investors. By hosting simple, lightweight meetups or dinner parties, or happy hours once a quarter, you can strengthen your network, build it, and keep those loose connections or weak ties warm. Mix professional and personal contacts: For me, a really boring event would be all work people. Look for occupational diversity. If you're hosting a work event, invite some other random folks who you know are gonna be good conversationalists and add to the energy. Don't reach for the top shelf first. Most important advice for leaders: do not invite your most impressive contact to your very first happy hour or meetup. Your first party should be for your neighbors, the parents of kids at your school, those LinkedIn connections, high school buddies you haven't seen in a while. Your first party should be a comfortable meetup for 15 to 22 people that you host at your home with just cocktails, not a dinner party. Then slowly, once a quarter, you'll be adding more people to it and filtering your list. Collect RSVPs to ensure attendance. New hosts are absolutely terrified that nobody will arrive. As long as you get a minimum of 15 people to show up, your party will generally be a success. Use platforms like Partiful or Mixily (not Paperless Post or Evite) to get people to RSVP, let them know what to expect, and send reminder messages. Ten days before, send a reminder message hyping up the party. About a week before, send another reminder message with a little dossier of who the attendees are. Write something little: "Ryan Hawk hosts a podcast. He wrote a book. He lives in Ohio. Ask him about the ski trip he went on with his family." This serves to make anxious people or socially awkward feel like they're welcome and they have a conversational access point. Practical hosting tips on event day: Label your trash cans and your bathrooms. As people arrive, greet and welcome every single person, and make them a name tag. Write it out right in front of them, first name only. Do not pre-write your name tags. Force collisions through structured activities. Your job as a leader is to go through life collecting the interesting people that you meet and helping them meet each other. Can you become a connector? One way to be a connector is to host these meetups and force the collisions. Lead two or three rounds of introductions at your meetup. Make a little announcement 30 minutes after it starts: "There are so many interesting people here. I want you all to meet each other. We're gonna split into small groups. It might seem silly, but I promise the purpose tonight is for you to talk to as many new people as possible. We're gonna split into small groups of three or four people, and you're gonna go around and tell your life story in two minutes." End on time, especially for weekday events: Host from 6:30 to 8:30 PM with a hard stop on Tuesday or Wednesday nights. People appreciate having an end time because they have responsibilities. Having that end time makes them more likely to RSVP yes and actually attend. "I get more compliments on my party ending on time, and they leave with a positive experience, so they want to return for another." Why every leader needs a personal website. If you have a blue check verified on Instagram, if you post at least once a month on LinkedIn, you probably need your own personal website. It's proactive reputation management. People are out there searching for you on Google and on ChatGPT. It may not happen every single day, but it probably happens every week. Whether it's parents of your kids at school, whether it's new employees, people are googling you. You want to have a personal website to put your best foot forward and make a good impression. Carrd.co to create a simple homepage or cloudflare to set up your domain name. Keep it simple: You don't need a Gary Vee type page. Your page can look like a Google Doc. Feed these large language models your story and bio. My website is plain text, simple homepage. I used to have a fancy design site. Now I'm like, dude, it doesn't matter. 80% of my visitors are on their cell phone and just want to read some text and have some links. The tweet from 2024 that changed everything. The viral Tokyo blind date trip taught me I was ready to share my life with someone. I ended up meeting my wife a couple of months after this experience because I realized I was ready. From a business perspective, one of the most interesting things while that was happening and for about a week afterwards: anyone would accept my phone call. My callbacks were instantaneous. My dial to answer fast. People were reaching out from everywhere. I was like, whoa, is this what it's like to be a celebrity? "I came back to Texas after the trip, ready to truly settle down and find a relationship and meet my now wife." Write like you talk: The best book about storytelling is Storyworthy by Matthew Dicks. Don't try to write a LinkedIn post that says "I'm happy to announce." Would you actually say that to someone? No, you wouldn't. Say it like you talk. Advice on Blind Introductions: Use a double opt-in intro. Reach out to one person first, "Hey, are you taking new clients before I connect you with a friend?" Get both parties' permission, separately - then send the email. Give yourself a Free Day: Dan Sullivan suggests one free day a quarter from work. Make it a weekday, and even get a burner phone so you can't check your work text/emails, so you're completely disconnected from work. The keys to being a great host/MC: Priya Parker does such a great job talking about the theory of being a good leader. The host that doesn't do a great job is the one who's too cool to care. Give explicit instructions to people. You are a ring leader for an event, and you're in charge of everyone's energy levels and keeping the show on the road. Add value before taking value. Never send someone a message, "I'd love to pick your brain," or "I'm looking for a mentor." That is take, take, take. Think about how you can add value first. When you add value first to people, it's some sort of law of reciprocity. They're much more likely to want to help you out or do something in return. Advice for new grads in the AI era: AI and new tools are eating into the ability for companies to hire low-level employees that do grunt work. Learn how to use the tools themselves. Work with small businesses and entrepreneurs where you can make a difference. Develop a writing practice: Matthew Dicks has this activity called Homework for Life where every night you write down some note, some anecdote, something that stuck out for you. It gives you ideas about things to write about. Use AI as an editor, not a writer: Don't outsource your thinking to AI. Use the tools, understand how to use them, but don't outsource your thinking. It'll spit back something decent, but you don't want to outsource your thinking, especially as a leader. Reflection Questions Nick says your first party should be for neighbors, school parents, and LinkedIn connections you haven't seen in a while (not your most impressive contacts). Who are 15-20 people in your life that fall into this "comfortable but haven't connected recently" category that you could invite to a simple cocktail party? He emphasizes "add value before you take value" and never says "I'd love to pick your brain." Think about someone you want to connect with. What's one specific way you could add value to them first before asking for anything in return? Nick hosts events once a quarter to keep weak ties warm instead of trying to have individual coffee meetings with everyone. What's one relationship-building activity you're currently doing inefficiently that could be replaced with a group gathering? Additional Learning #663 - Priya Parker: The Art of Gathering #545: Will Guidara: Unreasonable Hospitality #430 - Matthew Dicks: Change Your Life Through The Power Of Storytelling Audio Timestamps 02:06 Icebreakers and Personal Stories 02:55 The Art of Hosting Events 08:27 Practical Tips for Successful Gatherings 20:16 Mastermind Events and Personal Websites 25:36 The Importance of a Personal Website 26:47 Crafting an Engaging Bio 29:27 The Viral Tokyo Trip 37:04 Living an Interesting Life 41:57 The Art of Hosting and MC'ing 44:50 Advice for New Graduates 46:35 The Power of Writing and Storytelling 49:07 EOPC
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51 MIN
665: Pat Lencioni - Five Dysfunctions of a Team, Fear-Based Success, Working Genius, Anticipating Objections, and The Hidden Cost of Proving Yourself
DEC 8, 2025
665: Pat Lencioni - Five Dysfunctions of a Team, Fear-Based Success, Working Genius, Anticipating Objections, and The Hidden Cost of Proving Yourself
Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Patrick Lencioni is the founder of The Table Group and a bestselling author of 14 books, including The Five Dysfunctions of a Team and The 6 Types of Working Genius. Behind his achievements (valedictorian, straight A's, business success) were childhood wounds that drove him to prove himself. Key Learnings "I think I'm really good at anticipating people's objections." I think about what they might be thinking and what I need to put out there. Whether talking interpersonally, giving a speech, writing a book, or on a podcast, I like to think about what the other person might be objecting to. Lean into empathy. I always felt like I needed to prove myself in order to be successful and to feel safe. That's not healthy. "When people tell you they got straight A's and were the valedictorian, the student body president, and got accepted to all the schools they wanted to get into, there's a wound there." Based on my personality type, I shouldn't have done all those things, but it was out of the need to prove myself. Which wasn't healthy for me. My parents had a hard time being affirming because of their own lives. It wasn't until I was 55 years old that a friend who's a psychologist said, "You, my friend, have childhood wounds you've never dealt with." I got good Christian counseling and realized that the way I grew up, I wasn't supposed to grow up that way. It's common in athletes & CEOs to feel like they haven't done enough. They need to do more. "You're a noun, not a verb. You are enough, and you're not defined by what you do." Great achievements come out of fear, but "true greatness is best when it's only in the things that you're meant to be great at, and that you're doing it out of freedom and passion and love, not out of fear of failure." I remember seeing Tiger Woods on the Tonight Show when he was four years old. He was being groomed to be a golfer when he was four. It's best in life when we discover who God means us to be, then we do the things we're supposed to do and we're okay with not being good at the things we're not supposed to. Are we too affirming now as parents? People who are pretty darn good at everything it's usually because they're doing something out of fear. When I was a kid, my parents came from World War II and the Depression. It was like, hey, you got a roof over your head. There was a lot of suffering, and they weren't really attuned to that. Now we are hyper worried of our own kids suffering. No, suffering is actually good. They need to know they're loved and safe, but they're not gonna be protected from what is necessary for their development. The mistake I made was, oh no, I don't want them to feel like I did. Thankfully at my age, I'm now interacting with my mostly adult children and explaining to them what I did wrong. The Teammate Trifecta - How should we use it?: When I wrote The Five Dysfunctions of a Team right after 9/11, I thought, "That's the book on teamwork." Then we realized you need The Ideal Team Player (humble, hungry, and smart) to hire people that fit on teams. Years later, we came up with Working Genius: Are they in the right seat? 3 steps to building a team: Don't let people on the bus if they're not humble, hungry, and smart. Make sure you have them in the right chair based on their gifts. Then teach them the Five Dysfunctions. Pat's Two Working Geniuses: Invention and Discernment "Invention means I love to come up with ideas out of nothing. Discernment means I love evaluating things, curating things. God wired me to do that kind of thing." When people say, "Pat, we have five minutes, and we need a new idea," I just take a deep breath and smile. One man's trash is another man's treasure. Every new idea I've come up with has been in the field, working with people. I asked Jim Collins, "Jim, you do all this research with data. I go into a room with leaders and just think, What's going on here?" He said, "Pat, that's just as valid as what I do. That's called field research and face validity." What is Pat terrible at? Finishing things. People say, "Well you finished 14 books." And that's because I had the help of others to make me finish those. I got a 4.0 in high school. That wasn't my personality. I went to every class in college, never blew off classes. My personality is the kind that should blow off classes that don't matter. But I was so afraid of failing and disappointing my parents and teachers that I did anything they asked. That was not natural; that was fear-based. Can we use fear as useful fuel? "You can use it in the short term, but if you're doing it in your life, no." "We should celebrate what other people are better than we are at things. We should literally celebrate what we suck at." If we have two kids and one's creative and the other's disciplined, we tell the creative one to be more disciplined and the disciplined one to be more creative. No. We have to say, understanding that you're not creative is good for you. That's not who you're meant to be. The hardest thing about being a parent is constantly asking yourself, "Am I pushing them too hard or not enough?" The hardest question you ask yourself as a parent is, "Am I pushing my kids too hard or not hard enough?" This question also applies to yourself. In Working Genius, should I work on my working frustrations? The short answer is no. Working Genius is all about knowing what you love to do. Enablement and Tenacity are my working frustrations, and so many of those things fall into parenting. I'd say to my wife, "Hey, Laura, let's outsource some of these things." Out of fear and guilt, she said no because she felt like she'd be a bad mother. Outsource the work you don't enjoy, and when you have to do it, try your best and don't feel guilty with the result. The electrical company turned off our power for not paying the bill. We need to accept our deficiencies and need to be able to laugh at the things we're not good at. Ryan's Learning Leader Team: When your whole team has Tenacity as their working genius, your team loves to finish things. You will never be flaky. You might stick to something that needs to be changed way before it needs to be. In my company, we're always up for a change in plans, but not great at following through. If your team doesn't have Wonder and Invention, force yourself to borrow from others outside the organization to get new ideas. The Five Dysfunctions of a Team Vulnerability-based trust changes everything in teams. Eric Spoelstra uses Five Dysfunctions with the Miami Heat. He started when they acquired LeBron James. He said, "I don't know what offense we're gonna run this year, but I know we're gonna use the Five Dysfunctions." I love it in basketball, especially because you see them on the court. When people can be so vulnerable that they can say it was my fault, or I need help, or I'm sorry I was kind of a jerk yesterday at practice, it changes everything. But when you have a player who doesn't admit when they made a mistake or who blames everybody else, the ceiling of that team being great is so low. Humble, Hungry, Smart has been a great tool for athletic teams. I define it: no ego, it's about the team (humble). Hungry means I go above and beyond. Smart means I have emotional intelligence. I have the team members say, "Which of those three is your lowest?" It is crazy how people will call out. The goalie said, "I'm not smart. I yell at guys on the field, and I demean them. I gotta get better." Another kid said, "I need to be hungrier. I don't do the workouts at home." Pat phrases it this way when meeting with athletic teams. "Okay, everybody, look around at your teammates and think about the thing they want to get better at. If you want to be a good teammate, when you see your teammate doing the thing he just admitted he wants to get better at, you need to call him out on it." Once people start to have that language, it's amazing how they're coaching each other. And if as a coach yourself, I think you should tell people, "When I was a player, this was mine." They're gonna go, hey, if the coach admits that, I'll do it too. For leaders with Enablement & Tenacity as top geniuses, how do they avoid burnout? You have to be willing to start with "I am prone to burnout if you guys aren't aware of what's going on." The people with enablement and tenacity will say, "I'll just do it," and then they do. We had 12 employees and only one had Tenacity. We said we are going to kill her because every time we have to get something done, we're gonna say, "Jackie will finish." When people have enablement and tenacity, they and everybody else need to say, let's not abuse them. How do we assess a company in a short amount of time without focusing on their financials? When I go into a company, I find out what their meetings are like. If there's no disagreement and they're not exhausted at the end of a meeting, that's a red flag. If good people are leaving an organization, that's a massive red flag. I like going around and checking interactions. Is there an intensity with people together? Or are they alone and quiet? Also, keep an eye on customer reviews. What are the customers saying? There are two extremes of humility problems: arrogance on one end, and lack of confidence on the other. I first identified humility as a problem when I saw a CEO who didn't care about his company's results, but if he went on TV and answered questions about why they didn't meet their numbers, he would make jokes and make others laugh. If he was happy from that versus getting the results they needed, that's an issue. What specific traits do leaders need to have to get hired? A leader has to simultaneously believe they are no more important than the people they lead. They also have to accept the fact that their behaviors and words ARE more important than others in the company. "The one thing the leader has to do is break the tie." This past Friday, I was in a meeting trying to deal with a strategic issue between two great people. I dropped a curse word and said, "Listen, I'm pulling the CEO card right now. I don't do it all that often, but since I am the CEO, this is where we're going." Because I don't pull it every time, people are glad to have a CEO that will do that. If you're doing it every time, you lose credibility. Advice for young professionals: I wrote a book called The Motive, and what I say to leaders when they're young is: make sure your motive for being a leader is about sacrificing and suffering for others. "I want to help this organization, or I want to be the kind of person that takes on more than others for their good." Leadership is a lonely and selfless thing. It's wonderful, but the personal economics of leadership are not good. If you don't sign up for that, don't be a leader. Too many people say, I want to be a leader. And if you really scratch below the surface, they'll say, I think it would make me feel important, I'd get attention, maybe I'd make money, I'd have power. When that's your motive for being a leader, you're not gonna be a great leader. Reflection Questions Pat says people who were perfect students (straight A's, valedictorian, student body president) often have childhood wounds driving them. What in your past might be driving your current achievements? Are you operating from freedom and passion, or from fear and the need to prove yourself? He teaches his kids' sports teams to identify which of Humble, Hungry, or Smart is their lowest, then hold each other accountable when they see teammates struggling with that area. What would you identify as your lowest, and who in your life could you invite to call you out when you're not living up to it? Pat says the motive for leadership should be "sacrificing and suffering for others," not feeling important or controlling what you work on. If you're honest about why you want to lead (or why you currently lead), what's really driving you? Would people who report to you say you're other-motivated or personally motivated?
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54 MIN