The Learning Leader Show With Ryan Hawk

Go to www.LearningLeader.com for 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 Jimmy Wales is the founder of Wikipedia, the free encyclopedia that anyone can edit. After his daughter Kira's birth faced medical challenges and he couldn't find reliable information online, Jimmy launched Wikipedia in January 2001. In this conversation, Jimmy shares why extending trust before it's earned creates better outcomes, how to deal with bad actors, and the seven rules for building things that last. Notes: Key Learnings (in Jimmy's words) Wikipedia launched 20 days after my daughter was born. When Kira was born, I realized that when you go on the internet, and you've got a question like, "what is this condition my daughter has?"  It just wasn't there. There were either random blogs or academic journal articles that were way above my head. Kira was born on December 26th, and I opened Wikipedia on January 15th.  Nupedia failed because of the seven-stage review process. Before Wikipedia, we worked on Nupedia. We recruited academics to write articles. You had to send in your CV showing you were qualified before you could write anything. We had very slow progress. I was on the verge of giving up. This top-down approach with a seven-stage review process before you publish anything that's no fun, and nobody's doing it. We let anyone edit and figured we'd add structure later. We thought we'd have to figure out who the editor-in-chief of the chemistry section is. You're gonna have to have some kind of authority and hierarchy. But I thought, let's just not have too much structure for as long as possible.  "It's fun. You could be the first person to create a page." There was a point in time when you could write, "Paris is the capital of France". That's amazing. It's not much of an encyclopedia article, but it was fun. It's like, oh, we can just start documenting whatever we know. People started just doing all kinds of stuff. The magic is when you come back and see others improving your work. You could just write a few facts down and hit save, and it's not very good yet. But you'd go back a few days later and see somebody dug in, and they added more information. That element has always been really important. Is it fun? Do you enjoy the activity? Do you meet interesting people? You spend one afternoon, you add a few facts, and then you think, you know what? The world's just ever so slightly better. Trust is conditional, not naive. Out of every thousand people, probably a small handful are gonna be really annoying. But it's really rare to have somebody who's actually malicious. The idea of assuming good faith, as we call it in Wikipedia, is extending trust first before it's been earned. It's conditional. You extend that friendly hand of trust. And if the person proves themselves to be super problematic, then you have to deal with it. To get trust, give trust.  Most people are decent. It also creates an environment where trustworthy behavior is rewarded. As a boss, wouldn't it be fantastic if you said, I'm going to go off and do this other thing, but I just trust my people are so good, they're gonna crack on with the work? Sometimes they'll make a call I would've made differently. That's okay. They're smart. Sometimes they're going to get it better than I did. "You haven't earned my trust." When somebody looks you dead in the eye and says, "You haven't earned my trust," that's destruction. It's the opposite of building a culture where people can thrive.  Extending trust works in parenting, too. When teenagers say, "Well, it doesn't matter what I do, they're going to think the worst anyway, so I might as well do the bad thing." That's really unfortunate. As opposed to saying to your teenager, "Yeah, you want to go out and stay a little later than before. I want you to do that. I trust you, but you gotta do it the right way." You give that trust and believe me, they come home right on time because this is my chance to actually nail this. Give your children an opportunity to live up to building trust.  When trust is broken, you can rebuild it faster than you think. Frances Fry is a Harvard professor who had a huge job at Uber when they had an enormous crisis of trust. People say once you've broken trust, that's it, you can never get it back. But is it really true? No, it's actually not true. She thinks companies can rebuild trust faster than you think. A teenager who's broken a rule can rebuild trust pretty quickly. And our job is to let them rebuild that trust.  The eighth rule is walk the walk. The rules of trust aren't just a lot of good words. You actually have to walk the walk. If you say "I screwed up" and you own that, but then you go back to being the same as you were before, you're not going to rebuild trust. But if you walk the walk, people will see that.  Airbnb rebuilt trust by walking the walk. Really early in Airbnb's history, someone rented out their apartment and came home and it was absolutely trashed. Airbnb handled it very badly. They were stonewalling. In this era, that's often the wrong advice. Not saying anything just means it goes viral. So they ripped off the band-aid. They said, Look, we screwed this up. They started requiring ID's for people renting apartments out, ID's from customers, and substantial insurance for owners. They walked the walk. Transparency doesn't mean sharing everything; it means sharing the process. If people can see your workings, they can see what you're doing and how it works, it gives them assurance in the process. It's about judgment calls. What would be helpful for us to share so people can trust the whole process?  If you think people are fundamentally rotten, you can't work with them. It's very easy when we look at the state of the world to be downtrodden, cynical, and don't trust anybody. If you think people on the other side of you politically or people at your workplace are fundamentally just rotten people, then you're going to have a hard time listening to them. You're going to have a hard time understanding where they're coming from. You're not going to do the right things that make sense to people. Which hurts all of society.  When you've been beaten up by life, change the channel. If you work somewhere where your boss doesn't trust you and your coworkers are all backstabbing freaks, it's time to change the channel. Every night, you should be trying to find a better position. Your number one criteria in looking for that next position is finding somebody who you think is a proper person to be your manager. Think of it as you're interviewing the company just as much as they're interviewing you. When you give trust, you attract trustworthy people. When you become known as a person who gives trust before it's earned, you magically attract trustworthy people. It's kind of cool how it works. Will you get burned every once in a while? Maybe. But you attract the type of people that you wanna be around. Curiosity is the ultimate love language. Get out there in the world and be curious. Asking people questions and being genuinely curious about their stories and learning about them and asking follow-up questions is a great way to show love and to connect with people. When you find yourself in a curiosity conversation where everyone's asking and learning, and they're head nodding and into it, there's nothing better. That's human nature connecting. We are born to connect and collaborate with others. It's quite easy and natural for people to fit into whatever culture is around them. We naturally like to work together to build something good. We're social, and we like to be social. We collaborate to build experiences together. A party with only yourself is not a party. Do what you love, even if it takes time to get there. One of the things that I think is really important is do what you love, do something that you really care about. Oftentimes for young people, there's this struggle between here's the thing that I really want to be doing, and here's the thing that's going to make me some money. Work really hard to find a way to put those together.  Reflection Questions Jimmy says extending trust before it's earned creates better outcomes, but it requires not being naive when someone proves untrustworthy. Think of a situation where you're withholding trust. Is it because of actual evidence that this person is untrustworthy, or are you bringing baggage from past experiences with different people? What would it look like to extend conditional trust in this situation? If you're in a leadership position, honestly assess: are there team members who feel you don't trust? What specific actions could you take this week to demonstrate trust before they've "earned" it in the traditional sense? More Learning #605 - Seth Godin: The Power of Remarkable Ideas #598 - Sam Parr: Bold, Fast, Fun (Founder of The Hustle) #645 - Ryan Petersen: Take Action - From Crisis to Solution Audio Pod Timestamps 02:07 Jimmy Wales' Early Fascination with Encyclopedias 04:28 The Birth of Wikipedia 07:35 The Trust Factor in Wikipedia 12:04 Managing Bad Actors on Wikipedia 15:28 Personal Reflections on Trust 27:05 Setting Reasonable Boundaries for Teens 28:18 Rebuilding Trust After It's Broken 32:37 The Importance of Transparency in Leadership 36:50 The Power of Positive Purpose 39:06 Practical Advice for the Trust-Broken 43:01 Connecting and Collaborating with Others 45:17 Career Advice for Young Professionals 49:41 EOPC

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

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

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

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