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My guest: Brad Stulberg is a bestselling author and leading expert on sustainable performance and well-being. He's written for The New York Times, Outside Magazine, and The Atlantic, and his previous books include Peak Performance and The Practice of Groundedness. His latest book, The Way of Excellence, is great. Brad's writing combines cutting-edge science, ancient wisdom, and stories from world-class performers to help people do their best work without losing themselves in the process.

Notes:

Never pre-judge a performance. When you're feeling tired, uninspired, or off your game, show up anyway. Remember the Beatles scene—they looked bored and exhausted, but Paul still wrote "Get Back" that day. You don't know what's possible until you get going.

Discipline means doing what needs to be done regardless of how you feel. As powerlifter Layne Norton says, we don't need to feel good to get going... We need to get going to give ourselves a chance to feel good. Stop waiting for motivation. Start moving and let the feeling follow.

Audit who you're surrounding yourself with. The Air Force study is striking: the least fit person in your squadron determines everyone else's fitness level. If you sit within 25 feet of a high performer at work, your performance improves 15%. Within 25 feet of a low performer? It declines 30%. Your environment isn't neutral... Choose wisely.

Treat curiosity like a muscle. It's a reward-based behavior that gets stronger with use. When Kobe said he played "to figure things out," he was tapping into the neural circuitry that makes learning feel good and builds upon itself. Ask more questions. Stay curious about your craft.

Excellence isn't about perfection or optimization... It's about mastery and mattering. It's about showing up consistently, surrounding yourself wisely, and staying curious along the way.

To the late Robert Pirsig - one of the greatest blessings and joys and sources of satisfaction in my life is to be in conversation with your work. He's the author of Zen and the Art of Motorcycle Maintenance— "gumption is the psychic gasoline that keeps the whole thing going."

Arrogant people are loud. Confident people are quiet. Confidence requires evidence.

The neural circuitry associated with curiosity is like a muscle: it gets stronger with use. Curiosity is what neuroscientists call a reward-based behavior. It feels good, motivates us to keep going, and builds upon itself.

Kobe didn't play to win. He played to learn and grow. Kobe Bryant said he didn't play not to lose, and he didn't even play to win. He played to learn and to grow. He said the reason he did that is because it's so much more freeing. If you're really trying not to lose, you're going to be tight. If you're really trying to win, you're going to be tight. But if you're just out there to grow, you're going to be in the moment. When you're in the moment, you give yourself the best chance of having the performance you want.

The word compete comes from the Latin root word com, which means together, and petere, which means to seek, rise up, or strive. In its most genuine form, competition is about rising together (Caitlin Clark's story against LSU).

Love: The Detroit Lions had just won their first playoff game in 32 years. Following the game was a scene of pure jubilation. During a short break from the celebrating, the head coach, GM, and quarterback all gave brief speeches. Which collectively lasted about 2 minutes. During those 2 minutes, the word LOVE was repeated 7 times.

Homeostatic regulation -- Sense it in the greatness of others and when you're at your best. What Brad calls "excellence."

Surround yourself with people who have high standards. When things don't go your way, when you're inevitably heartbroken or frustrated, it's the people around you, the books you read, the art around you, the music you listen to, that's the stuff that speaks to you and keeps you going. It keeps you on the path even amidst the heartbreak.

Process goals work better than outcome goals for most people. If you're an amateur, you should be process-focused. When I train for powerlifting, I don't think about the meet that I'm training for. I think about showing up for the session today. If I think about the meeting, I get anxious, and my performance goes down. But if you're Steph Curry and you've been doing your thing for 20 years, you can think about winning the gold medal because your process is so automatic. For 99% of people, focus on the process.

"Brave New World" turns fear into curiosity. When you walk up to a bar loaded with more weight than you've ever touched, there can be fear about what it's going to feel like. If you go up to the bar with fear, you're going to miss the lift. If you're convinced you're going to make it, you'll make it, but your nervous system knows when you're lying to yourself. The middle ground is curiosity. Instead of saying "that's heavy, it's scary," I say "Brave New World. I've never touched this weight before. I have no idea what's going to happen, but let's find out." It splits the difference. I'm hyped, I'm giving myself a chance, I'm not lying to myself, but I'm also not scared.

Curiosity and fear cannot exist at the same time in the brain. There are seven pathways in the brain defined by affective neuroscientist Jaak Panksepp. Two of those pathways are the rage/fear pathway and the seeking/curiosity pathway. These pathways cannot be turned on at the same time. They compete for resources. It's a zero sum game. You cannot simultaneously be raging and curious. You cannot be terrified and curious at the same time. If you get into a mindset of curiosity, it's extremely hard to be angry or terrified. By being curious, we turn off the fear deep in our brains and give ourselves a chance to perform our best.

Practice curiosity in lower-consequence situations first. Curiosity is like a muscle. If you're about to do something absolutely terrifying and you're really scared and you say, "I'm just going to be curious," you know you're lying to yourself. You have to practice in lower-consequence situations first. When you, as a paren,t get really upset with your kid, try to be curious about their experience. Watch your anger calm down. When you as a leader, have a board presentation where you're feeling anxious, try to have that mindset of "Brave New World." When you're an athlete going into a big game obsessing about what could go wrong, try to be really curious instead.

The best competitors have emotional flexibility. As a competitor, you would know that in the confines of the game, you're not singing Kumbaya, you are trying to kill them. Then you have the emotional flexibility the minute that game ends to respect them as a person. That is the best way to compete. That's when our best performances happen. It's not either/or, it's both/and. It's playing really hard, giving everything you can for the win, seizing on your opponent's vulnerability, at the same time as having deep respect for them.

You don't have to be miserable to be excellent. There are people like David Goggins or Michael Jordan who seem motivated by anger and a chip on their shoulder. But Jordan would put his tongue out like this primal expression of joy when he was about to dunk. And Jordan won all his championships while being coached by Phil Jackson, the Zen master of compassion. There are the Steph Currys of the world, or Courtney Dauwalter (best ultra marathoner to ever exist), or Albert Einstein (total mystic who had so much fun in his work). There are two ways to the top of the mountain. For 99.999% of people, you end up performing better with fun and joy, and you have so much more satisfaction, which contributes to longevity.

The best leaders take work seriously but laugh at themselves. The best leaders I know in the corporate world, they take the work so seriously. They are so intense. But my God, do they laugh at themselves and their colleagues and have fun.

1. Brad says, "The things that break your heart are the things that fill your life with meaning." What are you currently holding back from caring deeply about because you're afraid of getting hurt? What would it look like to step fully into that arena despite the risk of heartbreak?
2. The Air Force study showed that sitting within 25 feet of a low performer decreases your performance by 30%. Honestly assess who you're spending the most time with right now. Are they raising your standards or lowering them? What specific change could you make this month to shift your environment?
3. Brad uses "Brave New World" to turn fear into curiosity before big challenges. Think of something coming up that makes you anxious. Instead of trying to convince yourself you'll succeed or dwelling on the fear, what does it feel like to approach it with pure curiosity: "I've never done this before. Let's find out what happens."

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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:

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.

1. 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?
2. 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

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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.

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.

1. 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?
2. 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?
3. 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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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.

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.

1. 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?
2. 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?
3. 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.

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.

1. 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?
2. 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?
3. 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

Two Great Ice Breaker Questions:

1. What's a compliment that someone has given you that you've never forgotten about?
2. 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.

1. 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?

2. 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?

3. 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?

#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

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: Angie Hicks, co-founder of Angie's List (now called Angi). She started the company at just 23, going door-to-door as a self-described introvert and non-salesperson, and turned it into a national platform trusted by millions. During our conversation, we discuss what it takes to lead with authenticity and build lasting impact.

Key Learnings

Lead by listening and showing up. Whether it's knocking on doors as a 23-year-old or meeting employees during office hours as CEO, Angie reminds us that being present, paying attention, and seeking feedback is the heart of leadership.

Focus on people and learning. Angie's career filter is simple: Do I like the people I'm working with? Am I learning new things? If yes, keep going. If not, it's time to reconsider. Excellence isn't just about results. It's about the environment and growth around you.

Take your work seriously, but not yourself. Confidence, humility, and authenticity go hand in hand. Angie shows us that you can be ambitious and driven without losing sight of the human side of leadership.

From Angie...

My co-founder, Bill Osterle, came to me when I was a senior in college and said, "Hey, I've got a crazy idea. Your parents are gonna hate it. But why don't we start a business?" I talked to my parents, talked to my friends, and then I ended up talking to my grandfather who was incredibly conservative. He grew up in the Depression, very fiscally responsible.

"What do you have to lose? You're 22, your parents aren't going to let you starve, and you're not trying to support a family, so why don't you try it?"

I was so taken aback by his response that that comment was probably what pushed me over the edge. I think young people can do this a lot, as we tend to overthink decisions. Sometimes people see things in you that you don't see in yourself, and you've gotta have a little faith. What better time to have a little faith than when you're young and carefree?

Work hard, and things will come your way.

We started in 1995. It was an offline world. We started as a call-in service and a monthly newsletter. The first name of the company was Columbus Neighbors. We left it like that for a year, and people just didn't get it. They thought the newsletter was the list. We decided to do a rebranding nine months in. We had two options: The List or Jackie's List (Jackie was the mother of one of our investors who knew everybody). At the last minute, Bill said maybe it should be Angie's List. "She does answer the phone."

Going door to door was hard. There was a lot of crying, I will be honest. I was selling something that wasn't concrete. "Hey, so when you need a plumber, you're gonna call me and I'm gonna help you find a plumber. And then when you hire someone, you're gonna tell me about it." I viewed it as a numbers game. I need to knock on so many doors every day, and that's just what I'm going to do. Hopefully, if I stay on my pitch and I knock on enough doors, I will sell the right number of memberships. If I was selling one or two memberships a day, that's great. No business was gonna be built on me selling one or two memberships a day, but that's where we were.

Sometimes you have to do the hard stuff. Sometimes you have to do the stuff you're not good at, and you have to figure out ways to work around it.

Because no matter what you do in your career, there's gonna be stuff you don't love. I broke it down by like, I'm gonna do it for these two hours. I'm a believer in the you can do anything for a year philosophy. I could do anything for an hour a day. So you have to kind of disconnect and treat it that way, as this is like taking my medicine. But you do win every once in a while. And it is fun when you win. It is fun when you sell something. The day Patty gave me her church directory was the best day ever.

You gotta celebrate the little wins as well in life.

Starting a business is a long journey. It is more of a marathon than a sprint. There's usually not this burst of momentum where everything rolls your way. It's building blocks along the way. If you don't celebrate those little wins and you only focus on, oh, I'm not gonna be happy until we're at 10,000 members, that could be years. You need things to keep you going every day.

Patty lived near Bill, so she kinda liked him too, but I think there was a little bit of entrepreneur in Patty. Patty needed nothing from us. She had lived in Columbus her entire life. She had renovated a 1920s house. All she was able to do was give. She knew everybody. But I think she just loved the spirit.

You don't know whether that's door seven, door one, door 57, you don't know.

But there is typically a breakthrough. Staying true and persistent, you know, there probably weren't a lot of women starting businesses going door to door in 1995, and Patty was like, look, she's got some gumption. She's tackling a business that in many ways is a man's world. Construction is a man's world.

Whether that's starting a business or finding the right boss, or finding the right position, that same lesson is the same. I talk to young people, I say, Hey, you can do marketing anywhere. There's any company you can do marketing. When it comes to me... Go where you're gonna be with somebody who believes in you. That's gonna invest in you, because that's actually what's gonna change your trajectory.

It's not the name on the company that's gonna change your trajectory. It's actually who's got your back, who's coaching you, that's going to make the biggest difference.

The next inflection point for me was when we opened in Cleveland the year after that. It was the first market we had opened from scratch. I remember I went one morning and picked up the newspaper, picked up the Plain Dealer at the bagel shop across the street from my office. And there it was, our little two-by-three ad that said, "Tired of lousy service" with some clip art. I was so excited. I was like, This is amazing. We're in Cleveland. This is gonna be so great. And then I remember telling Bill, "We're gonna get so many calls." And he's like, "We're gonna get so many calls." And I don't think we got any calls that day.

The transition from individual contributor to leading others was a horrible transition. It's actually really hard. I tell people that all the time because if you think about who do we promote in companies, we promote really strong individual performers.

The skills that make us really good individual performers do not necessarily make us good leaders, managers, et cetera, because it's actually a whole different skillset.

I was that overachiever kind of controller, let me just do it type person. You have to actually train yourself to not do those things because no one's ever going to be successful and learn if you're just over there stepping in. The early days when I was young and trying to manage people, not good. Not good at all. I ended up leaving for a year and a half to go to business school. I was pretty burnt out on the business, and I probably would've left the business had I not gone. It gave me a chance to reflect on where I've been and step back. Now I understand, I'm not in the pressure cooker. I can see where I've mistepped.

I left when I was 25, three years in. The business had gotten big enoug,h and we decided to bring in a CEO because the 22- 23-year-old was kinda like, maybe we need some leadership here. My co-founder joined full-time at that point and came in as CEO. I joke around, I'm like, take a break. I was still keeping the books.

The TV commercial was a hundred thousand dollars, which I had to convince our board on. I was like, look, either we try this or we just close Cleveland because there is no scenario here that we're gonna build a business with door-to-door sales at the rate we're moving. We basically took everything on Cleveland, which was $100,000. I would've been devastated had it failed. People started calling. I was so excited. Then all of a sudden it just kinda went bananas. You realize there's a lot of people with this problem. Doors slammed in my face at that point, not as much of an issue. And then we ended up being in Boston and Washington, and a bunch of other cities. Every time we'd go to a city, I'd fly in, and I would open the paper, and I would get all happy.

The TV commercials themselves were funny because I can't do anything for fun anymore without seeing myself in the commercial.

I did the first one, and they're like, listen, we're just gonna, we're not gonna tell anybody. It's just gonna go on, you know, we're just gonna do it really quietly. I was like, great. Okay, fine. And then it kind of took off. I had young kids at the time. I wouldn't let us advertise on kids' shows. There was never us on Disney Channel or Nickelodeon because I didn't want that. But the kids would see me on TV. You know, they would see me doing interviews. It happened for them at such a young age that they just kind of thought that's what parents did. I remember one of my kids coming home in middle school and being like, I can't believe you didn't tell me you were famous because it was finally, the friends had grown up enough that they were like, you know who her mom is, right?

I became a little more closed off in my personal life as I became more public. Kids deserve to grow up in a world where they get to be kids and not have to deal with that stuff. In our little town, people were like, Oh yeah, she just lives here. And it became not a thing. It became more relevant to me when I was traveling.

I started doing office hours. I did it on Fridays leading into the lunchtime, which, let's be honest, was probably one of the squishiest times of productive work. I was with a group of CEOs the other day, and I actually suggested, just try a little. It doesn't have to be a big thing. Just try a little and see where it takes you.

The meetings were anything. It was career advice. What should I do? They might have ideas for the business. Hey, we should go into this line. I remember talking one day to our head of legal, and I was like, you know, I don't get open-door media requests anymore. And she kind of chuckled, and she said, That's because you have them all the time.

You allow problems to come to you before they're big problems, so they become less of a thing.

I'd rather people bring their concerns internally first and listen to 'em and address 'em when you can. They always come internally first, whether it's from an employee, whether it's from a customer. It's just how we handle those things as to whether they blow up into something bigger. I always tried to give them something in return. They come to talk to me and I'd introduce 'em to someone who would help. I'd open a door for them.

To this day, I still love talking to customers. I think we live in a very digital age, and I feel like we don't talk to one another very much. People like people. They need to feel heard and have things resolved. I took that office hours idea, and now I do it with customers, so any pro can sign up and talk to me. Gives me a chance to understand, get a pulse on what's going on.

The people on the front line are the ones who are making your brand.

The marketing team might make some great social posts and some great TV ads. But many times, the people who are manning the phones or your chats are the ones that are leaving a more lasting impression on your brand than anything else. How do you bring the voice of the customer into the organization? Not everybody in our company is a homeowner. How do you make sure they can understand the customer? What's life like as a small business owner, as a pro? What's it like for a homeowner when something goes awry on their worst day? How do I bring those stories to life?

I had to convince myself that it was a good use of time. Busy people who have lots of responsibility are active doers, overachievers, to sit back and talk and listen feels like, Okay, am I moving the needle? It feels a bit too squishy. That's why I would treat it just like some of the other things. I will give it an hour a week. Let's see what happens there. I could see the payoff. I can't go spend 30% of my time doing this, but there is a portion of time that I do dedicate.

Feedback is a gift and something you should seek out. But yeah, it doesn't always feel great. One of the hardest pieces of advice I got came at a time when we were actually trying to do a transaction. They said, "You have an executive presence issue." And I was like, what? They said, "You're too nice to everybody. It doesn't help the company." I can't tell you how much that comment just killed me. But then I went out and got an executive coach, and I reflected on it. In many ways, it made me a better CEO. I learned that I could be me and I could still be nice and I could be kind, but there are moments I have to be clear.

When I'm looking to promote someone or hire someone, knowing your stuff is super important. You don't want this person, who says, I'm the one who always knows the answer. You want someone who can learn from their team. I spent most of my career running marketing, and marketing moves fast. Some of the youngest members of the team are teaching me more things over the years than even some of the more seasoned marketing people. How are you constantly having a view about learning and staying smart in the trade?

The ability to just be a good partner or work with people is important.

Your job's not to come in and knock down walls. It's actually to build relationships because you can't do everything yourself. How are you at building cross-department relationships?

My advice to recent grads: One of my favorites, take your work very seriously. Be good at what you do. Don't always be looking for that next thing that you gotta go tackle. Do what's in front of you first.

Don't take yourself too seriously.

You come out, you're like, Oh, I have all of these credentials. I should therefore be able to do these things. Sometimes the envelopes need stuffed and we might all do that together. So don't take yourself too seriously. We're gonna do this together.

Be open to feedback and to helping others. Don't be afraid when people suggest things that seem totally counter. I think sometimes we get too rigid in our plans. I use Angie's List as an example. I was supposed to be a consultant. I was supposed to go be a business consultant, but then Bill comes in and says, hey, what about this? I could have easily been a business consultant and had a nice life. But I chose that door. A lot of times, people get a little too narrow in their focus and miss opportunities. So stay open to that.

For me, it's all about the people you work with.

Working with people that you're learning from, that believe in you, that's all that matters. I overindex there. People ask me, how are you still doing this after 30 years? I ask myself two questions, and if I can answer yes to those two questions, I'm in. If I answer no, I'm out.

The two things are: Do I like the people I'm working with, and am I learning new things?

When you're as long in your career as I am, you have to dedicate time and effort to learning new things so that you don't become that person that is like, we do this because we've always done it this way. Which I think is just like the worst line ever.

1. Angie's grandfather asked, "What do you have to lose?" when she was 22 and hesitating about starting a business. What decision are you currently overthinking that you might need to just take a leap on while you're young (or young enough) and the risk is manageable? S
2. She says the skills that make us really good individual performers don't necessarily make us good leaders. If you've recently been promoted or are leading others, what specific "doer" habits do you need to let go of so your team can learn and succeed?
3. Angie stayed at Angi for 30 years by asking herself two questions: "Do I like the people I'm working with?" and "Am I learning new things?" How would you honestly answer those two questions about your current role? If the answer to either is no, what does that tell you?

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.

"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.

1. 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?
2. 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?
3. 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?

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: David Adelman is the CEO of Campus Apartments, founder of Darco Capital, and co-owner of the Philadelphia 76ers. During our conversation, we discussed how losing a basketball bet at age 11 changed his life, investing his bar mitzvah money in real estate, becoming CEO at 25, his grandfather's Holocaust survival story, and why it gives him perspective on struggle, embracing failure, the trade-offs of building something excellent, and what he looks for when hiring leaders.

"Why not me? Why not now?" David's mantra cuts through all the overthinking and excuses we make. When he saw other people building national real estate portfolios, he didn't wonder if it was possible—he asked why he couldn't do it. Stop waiting for permission. Stop waiting for the perfect moment. Ask yourself: why not me? Why not now?

Make mistakes, just not the same one twice. David doesn't expect perfection from himself or his team. He expects learning. Fail fast, fail forward, but don't repeat the same failure. That's not growth—that's negligence. Embrace the suck, but evolve through it.

David's grandfather survived the Holocaust after his wife and children were murdered. He escaped, joined the resistance, and rebuilt his life from nothing. When David thinks about that, he says: "No matter what, I don't know struggle." That's perspective. Most of what we call struggle is just discomfort. Understanding that doesn't make your challenges disappear... It makes them manageable. If your grandfather could survive the unthinkable, you can handle the hard day in front of you.

At age 11, David challenged family friend Alan Horwitz to a basketball game and made a wager. Horwitz didn't let the kid win, and David lost his basketball, football, and baseball glove. To get them back, he had to go to Campus Apartments every Saturday to sweep sawdust and stack lumber. This losing bet became his entry into a billion-dollar career.

At 13, David gambled his $2,000 bar mitzvah money by investing it with Horwitz in a building at 45th and Pine Streets in Philadelphia - a property his company still owns today. By age 17, he bought his first solely owned investment property.

David was accepted into Temple University Beasley School of Law but chose to become a Property Manager at Campus Apartments instead. At age 25 in 1997, he became CEO of Campus Apartments.

His grandfather, Sam Wasserman, was captured by the Nazis in 1942 and taken to the Sobibor concentration camp, where his wife and two children were immediately executed. Wasserman escaped during an organized revolt, joined the resistance, was wounded in battle, and was cared for by a woman named Sophie, who became his second wife. David said, "I feel a deep connection to him and what he went through. It's more like a sense of duty to honor him."

David says, "I bet on jockeys, not horses. I ask, 'If the thing fails, would we support them again?' To be clear, a lot of our [investments] are going to fail.' He learned the hard way: "Friends would say, 'Here's a deal, put in X amount,' so you know, it's $250,000 or $500,000 or $1 million. I realized very quickly that it's probably a money-losing prospect to just invest in a friend of a friend's idea or because someone at your country club is investing in it."

"It's called working off your debt." I literally lost everything to my "Uncle" Alan in 30 minutes when I was 11. My baseball glove, football, basketball, even my bank book. Every Saturday, I had to stack lumber and sweep sawdust to get one item back. Two years later, at my Bar Mitzvah, my parents asked if I wanted to give my gift money to my grandfather, who was good at picking stocks. I said no, I want to give it to Uncle Alan and buy real estate. At 13, I drove around with him, picked the biggest building he owned, handed him $2,000, and became a partner.

My grandfather was in Poland with a wife and two kids when the Nazis rounded him up. There were two lines. One for men, one for women, and children. He never saw his wife and kids again. He escaped from the Sobibor prison camp, became a freedom fighter, got shot, and was in a hospital recovering when a woman checking on her brother saw this lonely soldier and went over to check on him. That was my grandmother. My mother was born in a displaced persons camp after the war.

"No matter what, when I'm getting the crap kicked out of me in business or anything else, I don't know struggle." I think about my grandfather and what he went through. "That guy knew pressure and made it through the other side. So I have to stop being a little bitch about it and lean in."

Uncle Alan always said, "Whatever you do in life, it shouldn't feel like work." I have never said I'm going to work. I say I'm going to the office. Now, am I tired sometimes? A hundred percent. Did I miss a lot of stuff with my kids? Absolutely, and I have deep regret over that. With success and money comes a price, too.

Becoming a CEO at 25. "Why not me and why not now?" I live my life by this mantra. In the 1990s, no one was doing student housing at large scale nationally. I saw this white space, and I'm like, fuck it, let's do it. "I'm not afraid to fail. And I think if you're not afraid to fail, it's a freedom."

"Embrace the suck." Not everything's gonna be fun. Some things are hard. But sometimes when you push through them, you get to another side. Sometimes you don't, and pulling the plug is okay if it's not working. I've gotten good at understanding that a business might be a great opportunity, a great idea, at the wrong time.

When building something…If you aren't willing to make sacrifices earlier in your career and build that foundation for the future, being an entrepreneur might not be for you. I made choices to miss things with my wife and kids. Were all those things I missed worth it? Probably not. My daughters are 21 and 23 now, and I missed a lot of their early growing up. Four years ago, I apologized to my older one, and she said, "You know what, we remember this dad more than that dad." "It's never too late to make a change."

After you've done okay financially, it has to be about something else. The guys and women I roll with—"it's not about money. You either are wired to get up and work hard every day and do it, and it has to be about something else." It could be about providing opportunities for the people who work with you, or solving complex problems, or creating a business you're excited about.

"I don't think I'm the smartest guy in the room." You have to be open to learning. I continue to want to learn about other people's businesses. If I meet somebody, I'm like, tell me about that business. If you have that inquisitive mind, some guy tells me he's in the widget business, and I'll think of ten things they should try to do.

"I am never too embarrassed to say I don't know something." When we were selecting architects and contractors for the arena, I spoke to owners of the newest stadiums. Just lessons learned about the process. When I mentor kids, I tell them most people are afraid to say "I don't know" or "I don't understand." "If you're embarrassed for looking stupid, isn't it worse if you don't know what you're doing down the road because you didn't ask?"

"People don't know how to listen anymore. People wait to talk." They don't listen. When I have dinner with my youngest daughter, I hand her my phone so I won't be on it. I want to be there, I want to be attentive. Why are you wasting time meeting with people if you're not gonna listen to them?

"Make lots of mistakes. Just don't make the same one twice." Try hard. Don't be afraid to put yourself out there. The worst thing that happens is someone says no. I met my wife in a bar, literally in line for pizza. Turns out she was the school teacher two different women had told me I needed to call. The funny part is my buddy was talking to her best friend. He married her, I married Hailey, and our kids are best friends.

When it comes to sales. "Don't bullshit people. That's my number one goal." People can tell. Even at an early age, I had the humility to say I don't know everything. Here's my business plan, here's why I think I can scale Campus Apartments across the country when that wasn't being done.

When I'm hiring or promoting leaders, I look for three things. One is trust—I need to trust them. Two is creating an open line of communication. Three, "I don't think you're a successful leader or CEO if you're not willing to listen." There are a lot of dictator type CEOs. That's not me. Some of them work. "I don't manage from fear, I manage from bringing in opinions." For me, it's about having people who, in their individual swim lanes, are better at those jobs than you are.

The DeSean Jackson situation taught me about leading with curiosity. He made some anti-Semitic comments, and people came to me saying we need to cancel him. "Before I get there, I actually just want to find out what his intent was." The things he said were based on him being uninformed about the hurtfulness of those words. Not only was he willing to understand that, but he said, "Can you take me to your Holocaust memorial and actually educate me?" He came with his mom, no press. "It would be nice to take a moment before you're ready to convict somebody and actually have a conversation."

When I'm looking at investments, I really have to understand the product. I joke, "Do my kids at least understand it?" Number two: Who's the founder? People matter. I ask myself, if this thing goes bad, and as long as the guy's not a crook, would I invest with them again?

"I have to be more than just money in the deal." I like knowing when my influence and input can help make a difference. I think it's strategic thinking, introductions, and being a sounding board. The hardest part about being a founder is that they're afraid to tell investors bad news. "Bad news doesn't get better with time."

Advice to young professionals. "Try to get noticed for the right reasons." Show up and go to work. Go get coffee when you see your boss's boss there. Don't be afraid to introduce yourself. Ask lots of questions. Be the person who says, "Could you explain that to me?" Folks in my position really respect that. "Don't be afraid to put out a bad idea."

I hate working from home because I think people are screwed by the opportunity to interact with people and better their career and learn things. You're robbed of chance encounters, of overhearing conversations, of learning by proximity.

We're building this arena in downtown Philly, not taking any city capital, and doing good things for the city. We came together with Comcast who owns the Flyers. "It's gonna be the best live entertainment venue in the world, located in Philadelphia." We're opening in 2030 with a WNBA team. For those counting Philly out, you're wrong—we're doing great shit here.

• David's grandfather survived the Holocaust, which gives David a profound perspective on what real pressure and struggle actually look like. What experiences in your own life or family history could you draw on to reframe the "struggles" you face in your work or personal life?
• He lives by the mantra "Why not me? Why not now?" and says that not being afraid to fail is a freedom. What opportunity are you currently overthinking or waiting on "permission" for? What would change if you asked yourself those two questions right now?
• David regrets missing parts of his daughters' childhoods while building his businesses, but his daughter told him, "We remember this dad more than that dad." Meaning it's never too late to make a change. What relationship in your life needs you to show up differently, and what's one concrete thing you could change this week?

More Learning From The Learning Leader Show

#126: Jayson Gaignard - Mastermind Talks

#273: Chip Conley – How To Be Wise Beyond Your Years

#476: Kat Cole - Reflection Questions, Humble Confidence, Building Trust

Time Stamps:

01:51 David Edelman's Early Lessons in Business

03:58 Investing at a Young Age

06:12 Family History and Holocaust Survival

09:53 Balancing Ambition and Family

18:17 Sustaining Excellence and Learning from Others

25:38 The Art of Listening and Being Present

26:16 Lessons from Childhood and Parenting

26:47 The Story of Meeting My Wife

28:23 The Importance of Taking Risks

29:52 Sales and Leadership Philosophy

30:54 Building a Nationwide Business

32:07 Hiring and Promoting Leaders

35:34 Handling Controversy with Compassion

38:15 Investment Strategies and Favorite Ventures

41:36 The Future of Philadelphia's Arena Project

44:05 Advice for Young Professionals

46:45 EOPC

Go to www.LearningLeader.com for full show notes

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My guest: Priya Parker is a master facilitator, conflict resolution expert, and author of the bestselling book The Art of Gathering: How We Meet and Why It Matters. Priya has spent decades facilitating difficult conversations in boardrooms, communities, and conflict zones. In this conversation, she reveals the mechanics of meaningful gathering and why most of us are doing it wrong.

A facilitator is interested in the life of a group. I think of facilitation as working with people who are interested in the infrastructure of three or more people who need to come together and are ideally changed for the better by what transpires between them. A facilitator thinks deeply about how to set up the conditions to increase the likelihood that transformation happens.

Great facilitators are obsessed with language. There's listening to make someone feel heard, but the difference between green facilitators and seasoned ones is an obsession and ability to hear, recall, and play with language. You have to understand what people are actually saying and be able to reflect it back in ways that unlock new meaning.

Understanding power is essential to facilitation. You need to know how decisions are being made, who is talking more than others, when to allow for that, and what your own relationship is to holding the group. When do you shut up? When do you pull people out? When do you push back? All of this is fundamentally about understanding power dynamics.

I'm a third-generation ostrich. On both sides of my family, when conflict arises, we stick our heads in the sand. Nothing to see here, folks. But I've cultivated the ability to hold heat. Even now, when facilitating a reckoning and the heat rises, my palms still get sweaty, I can feel my heart racing, blood rushing to my cheeks. But I've learned how to stay present with that discomfort. Counterintuitively, having deep empathy for people who want to flee makes me more effective.

"90% of the success of what happens in the room, and as a facilitator, happens before anybody arrives." This is what my mentor Randa Slim taught me, and it's absolutely true. The construction of the house happens before anyone gets there.

Dr. Hal Saunders changed everything for me. He was an American diplomat who served five presidential administrations and was part of the Camp David Accords. After leaving government, he realized that while governments can create peace treaties, people's perceptions of each other on the ground haven't necessarily changed. He trained me as a teenager in sustained dialogue, and I learned facilitation the way it should be learned—through apprenticeship. Even in his seventies and eighties, he always believed he had something to learn.

The first questions people ask you signify what they value. When I arrived at the University of Virginia, people kept asking, "What are you?" I learned quickly that they meant racially. My mother, an anthropologist, had taught me that the first questions a community asks reveal what matters most to them. Race was clearly very important there.

I made myself a conflict resolution facilitator. Growing up between two vastly different households—toggling every two weeks between a vegetarian, Buddhist home where the word "God" was never mentioned and an evangelical Christian home where we never ate before saying Grace. I became deeply interested in when and why and how people come together, what they think of as normal, how they create and change cultures, and how they come apart.

Your highest real estate is when people are together in the same place at the same time. Wasting time in the room figuring out what to say or do is actually wasting everyone's time. A huge part of preparing for any gathering is figuring out what the right conversation is for this group to have, and how to equip them to have it well.

Think of military pre-mission briefs. They're really good at setting mission objectives. This is the goal, this is what we're striving for. Then they debrief afterward to learn and do better next time. That same discipline applies to any gathering, whether it's a leadership retreat or hosting dinner at your house.

Every gathering is a social contract. You're creating a temporary constitution. At a dinner party, there's an implicit rule: bring a bottle of wine. People find out they've broken the constitution when someone says, "Wow, they didn't even bring a housewarming gift." We have all these implicit norms, and in diverse groups... Which is every group, not just racially, but people with different assumptions about how things work—you need to make the contract explicit.

Elizabeth Stewart ran a startup networking organization and wanted it to be a true community, not just a shark tank for pitches. She created a pop-up rule: you can't talk about what you're selling. No pitches. Super counterintuitive for a networking night, but it created exactly what she wanted... Trust and long-lasting relationships rather than transactional encounters. The rule signified what she was trying to create.

Using your power as a host means protecting your guests. You're temporarily equalizing people so they can coordinate group life. Gathering is fundamentally a coordination problem: helping people understand what the rules are, protecting them, and connecting them.

There are moments when you should surprise people. If a team is stuck in a 50-year-old institution that's always done things the same way, and they'll die institutionally if they don't change, maybe the purpose is to build their skills for discomfort and navigating uncertainty. In that case, maybe you don't tell them the full roadmap because the practice itself is learning to navigate the unknown.

Making things explicit and transparent equalizes the room. Showing the roadmap is deeply beneficial, particularly to people with less power and knowledge. For newer people who don't know how things work, for people with other obligations like tending to an elderly parent or being a student athlete with fixed schedules, transparency helps level the playing field. But it may not always be your purpose.

Before you default to a dinner party, ask what you actually need. If the goal is to laugh hysterically and create memories with friends you don't see enough, a dinner party might not be the best form. Maybe you should play kickball in the park, stage a made-up pickleball championship, go to a morning rave, or take a party bus to a concert. We're so boxed into thinking about how adults must hang out.

When hosting dinner parties, keep the menu relatively simple. Increase the meaning dial and it decreases the pressure on food quality. Think about food that tells a story.

The invitation matters deeply. I could send an invitation: "Come enjoy my best attempts at Ruth's BLTs." My grandmother's recipe that takes me back to childhood. I tell the story in the email, narrow the expectations, and create a social contract. This is for BLTs. If you're a vegetarian, you can take out the bacon. And please don't bring your mushroom penne, not in this context. Then I ask: bring a story of a dish that takes you back to childhood. The whole night plays itself.

Magical questions are questions everyone in the group is interested in answering, and everyone would be interested in hearing each other's answers. It's a magical equation. It's subjective and relative to each group. My seven-year-old daughter once asked at dinner: "What's the naughtiest thing you've ever done that was worth it?" We laughed and shared for two hours. My son asked my elderly father: "What's the meanest thing you ever did to anybody before the age of 15?" That caveat, before age 15, temporarily equalized everyone at the table.

Testing and practicing are how you develop the muscle. I test questions on my team, I think through social arithmetic: what do these specific people have in common, what don't they have in common, what's the right level of vulnerability? I ask my community on Instagram and Substack to share their magical questions. Someone from Brazil sent me: "Would you rather spend 10 minutes on the moon or one year traveling through Europe?" It inspires heated debates in his friend group.

My favorite question for virtual groups: "What was the first concert you ever went to, and who took you?" People pause, then you see a waterfall of answers—Bonnie Raitt, Madonna, New Kids on the Block. Everyone's interested in seeing everyone else's answers. You realize who's here, you see there's someone behind everyone (my sister, my mother, my college girlfriend), and you increase the likelihood that people realize these are real humans.

Creating psychological togetherness on Zoom is my single most important skill. During the pandemic, I lost all my physical facilitation tools. I couldn't chase someone into the bathroom to convince them to come back, couldn't use my body to signal it's time to quiet down. I was just a little green square. Magical questions became my most powerful tool for creating psychological togetherness when people aren't in the same room.

Ryan's champagne question works because it's visceral and emotional. "We're meeting exactly one year from today and popping bottles, what are we celebrating?" That's not "what's your goal for the year." That's boring. You pop champagne for something that matters emotionally. It's a somatic, physical question that forces people to think big because you're not popping champagne about something boring.

The responsibility of gathering is about both connection and power. Particularly in work contexts, you can ask questions that are too vulnerable or that aren't appropriate. You need to protect your guests by ensuring questions relate to the purpose of the convening. Asking "what's a core experience from your early life that connects to why you do the work you do today?" helps people understand motivations without crossing lines.

Questions can open up the world. They're a sequence of words that, if you ask them in a specific way, can fundamentally change what's possible. Being genuinely curious and fascinated about people and their stories and life experiences will change your life. Full stop.

Writing The Art of Gathering let me articulate what deeply frustrated me about gatherings and try to convince other people it should frustrate them too. What's been beautiful is that people are starting to get fed up with mediocre gatherings and expect better of how we spend our time together. They're realizing we can change it with some thought, some temerity, some bumping around.

The pandemic made the book even more relevant. The paperback came out in April 2020, when gathering was banned, which was super awkward. But by taking gathering from us, we began to see it. We began to see that this thing we took for granted shapes our lives—how we wed, fight battles in court, host funerals, host galas. People started asking first-order questions: when and where and why should we meet, and who decides? That's a powerful question to be asking.

Anyone can gather. Many of the hundred gatherers I interviewed for the book identified as introverts, loners, people on the outside of things, people with social anxiety. As one person said, "I create the gatherings I wish existed in the world. And other people seem to like it."

• What gathering in your life, whether a team meeting, family dinner, or community event, would be transformed if you paused to clearly define its purpose before diving into logistics and form?
• Think about a group you're part of where people come from different backgrounds and assumptions. What explicit "social contract" or ground rules could you create to help everyone understand how to show up and what's expected?
• What's a magical question you could ask in your next gathering that everyone would be interested in answering and everyone would want to hear each other's responses to?

More Learning From The Learning Leader Show

#126: Jayson Gaignard - Mastermind Talks

#273: Chip Conley – How To Be Wise Beyond Your Years

#476: Kat Cole - Reflection Questions, Humble Confidence, Building Trust