Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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Guy that ran the New York Comedy Festival, he's like, you know you're good. You're very good, right? And he goes, you know that's not enough though, right? You know you have to be great. And that is absolutely true in the comedy business where everybody wants to be a comic or everybody wants to be a great musician. Everybody wants to be a musician. Well, if you want to be a musician who stands out, who sells tickets, who can support himself and his family doing that thing, you have to be great. ...

And now, Escaping the Drift, the show designed to get you from where you are to where you want to be. I'm Jon Gafford, and I have a knack for getting extraordinary achievers to drop their secrets to help you on a path to greatness. So stop drifting along, escape the drift, and it's time to start Escaping the Drift.

right now. Back again, back again for another episode of Like It Says in the Opening Man, the show that gets you from where you are to where you want to be. And today on the show, look, we will always talk about being successful and reaching for that brass ring, reaching for the thing that's going to get you to that next level. But

My guest today is somebody that when I saw this come across my desk, I thought, what a great message to share with you guys, because this guy has it figured out that he can help you find happiness or believes you should be happy wherever you are on the journey, not just waiting to some mythical brass ring at the end to say, today, I'm happy. Our guest today is a comedian, a speaker, an author.

and the host of the Reasonably Happy podcast. Ladies and gentlemen, welcome to the program. This is Paul Olinger. Paul, how are you? What's happening, John? Thanks for having me. Yeah, man. Glad to have you. Where are you in the world right now? I'm sitting on the Upper West Side of Manhattan. I can see buildings on West 86th Street out the back window of our brownstone. Well,

Lovely. So I wish you could have come out to Las Vegas, but I'll take the second best, which is obviously having you on here. I look forward to having an excuse to come out and hang with you guys. You do. So I know that, look, you've done some amazing stuff reading the bio here and going through it. And I always like to think that success leaves clues. And I'm always interested in the nature versus nurture where I almost always start these interviews. So tell me about a young Paul Olinger.

Tell me about young Paul, the, uh, the, either the hero origin story or the villain origin story. Well, the, the, the nurture and the nature part of it is, I mean, I'm a product of my family. I'm one of six kids from a big Catholic family in suburban Atlanta, Georgia. I had two amazing, two amazing parents who were committed to their family and stayed together for 55 years until my mom passed away. Uh,

Um, and you know, I was always part of a gang. It was, it was, uh, it was a busy, crazy household. Uh, we, we weren't rich, but we had everything we needed. And, and, uh, you know, there was lots of people around and, and as crowded as it could be, I always knew I was part of something. And I, you, you, you wouldn't have put it in those terms when you were a kid, but looking back, you know, having been a part of that gang, you have a security, um,

built into you that people who don't have that maybe don't experience or at least as a child.

Now, when you say gang, is this like, are we talking about like little rascals? Like this is what you called your friends or is this a real gang? No, I mean like when you're one of six kids, you know, by the time I was the fifth out of six kids, you know, we were the Brady bunch, three boys, three girls. And we weren't unique at all in our Catholic church and our Catholic schools. I mean, you know, half the families had six kids or more. It seemed like

and you know, um, but when you get to high school, you know, when you, when you're the fifth kid, by the time you show up for your freshman year, you're like, Oh, you're one of the Ollinger kids, you know, which is you want to make your own way. But at the same time, the teachers know who you are, your older sisters, you know, tease you in the hall. They're there. Her friends are like, Oh, look at him. He's such a cute freshman or whatever, and make fun of you. And you feel like a complete loser yet on some level, it makes you feel, it gives you a

a safety net that was, I think that was a very big part of my childhood. You know, childhood dinners were, the dinner table at our family was very raucous. Whenever anybody would have, when one of my siblings would have a friend over to spend the night, they'd all like remark, good God, I've never seen a louder dinner table than what I just experienced with your family. My dad would go around and make everybody ask the guest a question. And then the guest would have to ask everybody at the table a question. It was,

It was, you know, it was sort of, it was like not, you know, it was like eight is enough for the Brady Bunch, but it was a very wholesome, positive way to grow up. We weren't perfect. We were dirty, nasty kids, but it was a positive environment to grow up in. That's an interesting thing you just said about your father having kind of a plan for teaching you guys how to communicate with each other. What did he do? What did your dad do? My dad was a nuclear engineer for Georgia Power. So he did...

environmental testing around nuclear power plants as part of the Georgia Power and eventually Southern Company System. So he was a nuclear engineer when Three Mile Island happened in whatever it was, 78, 79. And so it was a very relevant thing to do. But he's a brilliant guy. It's just not one of those jobs. And again, we had very stable upbringing, but it wasn't like he had money falling out of his pockets.

Well, I'm guessing with six siblings, right? Like that had to have instilled in you, like, I got to hustle a little bit. I got to speak up if I'm going to be heard. I got to stand up. That's 100% right. And I think it made me a very earnest person. It made me very hungry to find

for attention, you know, I mean, but to be my own person and have something to say and, and distinguish myself from my, you know, my older brother and my, and my family in general, you know, when I was a freshman, my brother Cole was a junior in high school. And for the first year of my high school experience, I just,

all I had to do, I just heard the girls, the beautiful girls at my freshman homeroom table talk about what a great looking guy my older brother was. And I was like, that's the last thing I want to hear. Right. So, you know, and I shared a room with him until I was a sophomore in high school and he was a senior. So, um, a lot of, a lot of closeness, a lot of competition that eventually, you know, not now my, my brothers and sisters are very, very good friends. And, um,

Yeah. You should have just gone the designer imposter perfume route. Like if you like it, like he's unobtainable because you're a freshman, but if you like him, you can have, you can have me. Yeah. You can have the. Paul's available. That's right. That's right. Well, I'm really close. Paul was available to them, you know, but when I got my braces off, maybe I, you know, things, things start to improve a little bit. So. Yeah.

My son's about to get his braces off, so I'm sort of like, oh, man, I wonder what's going to happen to him in the next few months. He's right at that point where he's about to break out. Well, let's ask this because, yeah, braces is a huge deal. I have one kid, my older son, right? He was in and out of braces in what seemed like five minutes. My daughter is on like year three of this siege with braces. And poor thing, man. She is –

She's a freshman in high school now. And she's like, when am I getting these off my face? So finally, I started asking my wife, I'm like, are we paying by the month with this? Do we need a second opinion? What's going on? So expensive. So let me ask you this, your older siblings, did you have any overachievers that made it very difficult for you?

Well, my brother was a very my old, my immediately older brother. You know, we had the benefit. He was fourth. I was fifth. We were only 18 months. All the youngest, the youngest four of us were all 18 months apart. So we were very close in proximity and in age. He was a very good student.

Um, he was a very good basketball player. Um, and so that was the immediate, you know, person I wanted to outshine. So I wanted to do better than him. So he was a captain of the basketball team. I wanted to be the captain of the football team, lead role in the play, head of the student government, all that kind of stuff. And I, and I ended up doing all that. So, um,

I was motivated and I think, you know, I think there's also part of this thing that, you know, you want to achieve because I wanted to get good grades because I wanted to know that I was okay, you know, and that's part of the thing that I've been exploring in the last five, six years with the podcast is to say, you know, we chase these things in our life, money, accomplishment, fame.

recognition, because we want to feel okay. We want to know that like, hey, I'm doing what I'm supposed to be doing. Look at my bank account. Look at my six pack abs. Look at the outward signs of success because they are indications of inner peace, but often they are not. And so that's the thing I've really been trying to unpack and explore on the podcast.

Yeah, I love that. When did you, so after, where did you go to college? I went to Rhodes College in Memphis, Tennessee, and then I ended up going to business school at Dartmouth.

Okay. So that's a great education, obviously, which led you to be, I think you were one of the first employees at Facebook or one of the first key kind of. I was, I was, I was like 250th employee at Facebook. Um, so still pretty early. And if I'd been smart, I'd have stuck around another few years and, um, we'd be talking on my yacht right now, but you know, I, I, I was very, very fortunate to get there when I did. And I, I worked with a lot of good people before I worked at Facebook. I was very fortunate to

be an early employee at a company called launch.com, which eventually got bought by Yahoo. And, and it was in the relatively early days of Yahoo and like phase two of Yahoo after the.com bubble burst and the company came back and rebuilt itself in kind of like internet

2.0. And, and that was a great, I worked with so many excellent people at both of those companies that sometimes it's hard for me to, to muster empathy for people. Cause I don't know what it's like to not work with great people. I've been just really, really fortunate my entire career to be surrounded by outstanding peers and mentors.

What were you in those early days with those companies? I mean, you're coming out of Dartmouth. You've got an MBA, I'm assuming, where you went to B school there, yes? Yeah, I came out of business school in 1997. And I was like, I had told jokes that I'd never done comedy before in business school, where I went to business school because I was very practical. I wanted to make more money. That's what I wanted to do. I didn't know. I couldn't tell you exactly what I wanted to do.

But when I got there, I was like, I saw Dartmouth at the top of my resume and I'm like, I can get in most doors now. Right? And the truth be told, I could have gotten in most doors if I had just willed myself into those doors without those things. But what's nice about a credential is you get three things with a fancy education. You learn some stuff, hopefully.

you get the name brand credential and you get a network and the network is very helpful. It just, it just gives you an advantage to help open some doors. Right. And your network is probably the most powerful thing you can invest in as a young person. Right. And it's, it's paid off for me over and over again throughout my career, both in business and even in comedy. And so, so when I got to Dartmouth, I was like, well, I can really do what I want to do. What, what excites me? And, and,

all I could say was I loved, and this was in 1995, 96, right? I was like, I love reading magazines. I love going to movies. I love TV. So I want to be in media. And I tried to get into those industries, but I had no experience. And I thought, well, what the hell? Nobody has any experience in the internet. Surely somebody will hire me there. And I got, I got in and, and, and,

The economy was so good in 1997 that these guys couldn't find anybody to hire with any experience in the advertising industry. And if they could, they wouldn't have hired me. And a few years later, when I had some industry experience, I wouldn't have gone to that job. So we were perfectly inexperienced. Matched at the time. At the right time, it was a perfect match for us.

And I just happened to meet some of the greatest guys that I could have met at that point in my career who became mentors and did a lot for me over the next years. But I ran the New York sales team, the ad sales team for launch.com.

from 1997 until the thing blew up and then i was out in la and then yahoo kind of brought us into the fold and and i stayed on the ad sales team at yahoo for a long time too i mean some of that that's got to be so here you walk into a job even though you even though you've got the dartmouth pedigree walking into a job that maybe you know is in an industry you don't know a whole lot about that's got to create a tremendous amount of pressure did you feel

any type of, I mean, I don't want to say imposter syndrome. You just went that came out of B school, but did you feel a lot of pressure on yourself to perform quickly? Yeah, I did. I mean, you know, I didn't know what I was doing. I had never lived in New York before. I'd never worked in advertising before. And what I'd sold was, you know, I, I basically talked my way into this job because I,

I was like, okay, I raised money in my college for three years after graduation. I sold ads for the Dartmouth, the business school student paper. I was like, I sort of like, you know, wove this, this story that I could sell. And by the time I got to the interviews with the launch guys, I was so clear about what I wanted to do and the kind of people I wanted to be with.

that I ended every interview when I was like, if there's any reason you don't want to hire me, I want to talk about it right now because I want this job. I want to be a part of this company. I want to be a part of this industry and I want to see where this goes.

So I talked my way into the job, but I still didn't have any, I still had no idea what I was doing. And probably nine months or a year in my boss sat me down. I'll never forget this lunch. Good buddy of mine to today still, but he sat me down and he said, look, man, if you don't start closing, we're going to fire you. And it was at the restaurant at black rock, which was the CBS TV headquarters on six, six Avenue in New York city. And he basically threatened to fire me. And that night,

It was a Friday and I went home and my girlfriend at the time came over and I told her what happened and I opened a bottle of champagne with her. And she's like, why are we celebrating? I was like, because I'm going to give it everything I have. And it's either going to work or it's not. But I'm going to go all in. And we had some champagne. And the next morning I got up and I went to the office and I started working, you

you know, 80, 85 hours a week, because why not? I was, I was single. I had no kids. My, my, my roommate at the time was working on wall street. He was working a hundred hours a week. My girlfriend was a consultant. She was on the road four days a week. I had the time to work.

And so I just started putting in the hours and I was like, if I'm going to fail, I'm going to go out swinging. Right. And so, and go figure it started working out. Yeah, no, this is okay. I'm fascinated by this story. This is, this is really interesting because do you think it was lack of effort? Cause you said you went to 85 hours a week. So you were probably just kind of doing whatever you were doing before. Was it effort or skill or a blend of the two?

And if you can think back, what did you do to sharpen the knife? How'd you get better in your skillset? Because look, I don't care. You can, you can put all the effort if you want, but if you don't develop a skillset and whatever you're doing, you're never going to be good at it. Well, you know, there's a lot of things that were going on. You know, I didn't really have, I didn't really have a focused person telling me what, showing me how to do what I needed to do. I don't think. And, um,

And I think what I needed to do was just not take no for an answer and not allowed myself to be ignored. And at that point in my life, I was like, you know, I had nothing to lose. I was completely naive about how little I knew.

And all I know is I wanted to succeed. And so I just started going like, all right, I got real focused about, here's the scoreboard. Here's all the leads I have. Here's all the people I know. Here's who the people can connect me with. And I really started working that network. And I had friends that...

you know, I went to business school with who were now in marketing, I would call them, I would call friends of theirs. I would call, you know, people who graduated four years before me and say, you don't know me, but you know, I'm doing this thing. I'd love to talk to you. And if you can't tell me, you know, if you can't help me right now, can you point me in the right direction? That kind of thing. Like I just really started prospecting much harder than I had. And the thing is, man, like

it's, it's, it was easier to do then than it is now when I'm selling like my own thing. Right. I really believed in my product. I really liked what we were doing. We were on the cusp of the, of, of technology and music in like 1998, 99 when things, you know, we were, we,

We were becoming Pandora or Spotify before there was even broadband to the home. And so we had a great idea. We had a great vision. It was just way too early. Now, being early is also being wrong. I get it. But I was really passionate about it. And I just started proselytizing.

the gospel of it and people could sense my commitment and my passion. The guy who is the Senior Vice President of Marketing at Tommy Hilfiger called me after I pitched him and he said, I want you to come work for me.

And, and I was like, I don't know anything about fashion. He's just, I just, I like your energy. I want you to come. And I went and I interviewed a top with Tommy and I just was like, you know what? I, I, you know, and I talked to Tommy Hilfiger in his office about like Keith Richards and, you know, like fashion and Rolling Stones. And it was really, really cool. But I wanted to be a part of that gang. I wanted to be a part of this, this, this gang that I had joined, um,

There's that word again, gang. The team I had joined at launch and I stuck around and I benefited from that. But

I don't know. I just started working in a way that most people would find to be irrational. But, you know, when you're 28 and you don't have kids and you're single and like, what else are you going to do? Yeah. But I think, I think even then, like, I think your upbringing showing through right there, because I think you were probably, you left your tribe at home and, and that side of it's always been appealing to you even in business. Yeah.

I mean, look, as humans, we always seek a tribe, right? But I just can't imagine. Like, I had two older sisters. We were all three years apart. So, you know, the one I'm fairly, you know, growing up as kids, yeah, I'm sort of close to the one because it's three years. But my older sister was gone to college by the time I was, you know, she left early. But, yeah, dude, I can see how that need to be in a tribe for you would be more important almost than a financial opportunity. That's cool. Yeah.

Well, they weren't mutually exclusive. I mean, I was also hoping to make a change there. And that wasn't the gig that paid me for the first. The first gig that paid was at Yahoo. When Yahoo bought launch, they just kept us alive. We had gone through the busting of the dot com bubble like everybody else. And when Yahoo bought us, the company had laid off four fifths of the employees, and I was lucky to make the cuts.

And we got to Yahoo and then Yahoo slowly started to come back. And I was very fortunate to be able to benefit off of that. Can I ask about that? Because I think there's with right now the economy doing what it's doing, there's a lot of people, especially here in Las Vegas, the casinos are laying some people off, trying to consolidate for their shareholders and turning good reports.

you know, I've never, luckily I I'm chronically unemployed. I pliable. I've always kind of been my own guy. I have, I've never been in a corporate setting where a layoff was a probability or even a possibility. What advice would you give to somebody as somebody that's navigated those waters? What advice would you give to somebody to, to keep your chin up or how to avoid the ax or whatever? Well, I, I was very fortunate to not

not, uh, get the ax, but I could feel the breeze on my, on my neck, you know? And, and, you know, the first, what happened from like 98, what happened in 98, 99 was all this money was flowing around and companies were hiring people. They were growing way too fast. They were hiring people that it was kind of like, you know, the people doing mortgages in 2007 when it was like, you know, anybody with a heartbeat could be a realtor or, um, you know, it's still that way.

Well, being a mortgage business, well, you know, this market's probably, you know, making it a little harder, right? So what a downturn does is sort of gets you back to right size. And so, you know, the first round of layoffs, it's like, well, those people probably weren't the right people to be here in the first place. But then like the second and the third round, you start going, oh, man, we're letting some good people go here. Like nobody is safe. And if there had been another round of layoffs, I wouldn't have made it.

Right. Like it was, it was down to like family members. So, so it was, you know, so the, the, but, but you know, what I think I saw was that people, people's attitude was the differentiator in many cases, people that were like doing their everything they could to succeed and,

even if they weren't the most talented people and I would count, I mean, I'm a talented guy. I work hard, but like, I think my hard work kept me around more than my talent did in some of those interviews or some of those layoffs. And so I think that attitude and, and hard work,

I don't, you sound like an old guy whenever you say something like this, but like, I think it's an underappreciated asset in today's world where, you know, you, you do see some of the rhetoric around younger generation and you're like, I don't hear a lot of people talking about like willing themselves to succeed. You see a lot of these posts on Instagram about, can you believe these banks are making their employees work a hundred hours a week? And I'm like, yeah, I can. That's, that's how they,

that's how they find out who's committed and who's not is it right well it's i mean is it is it unhealthy can be um you know but there's a lot of jobs that aren't investment banking out there waiting for you so like if that's not the gig for you go do something else go find something that you really love that is sustainable for you i don't think anybody

you know, goes into bank, anybody who thinks the banking is a, you know, a job for a 40 hour a week job is going to be wildly disappointed at some point along the way, you know, the, in the senior partners, these are guys that cancel vacations because there's a deal that pops up and they got to come home from Europe, leave their family there. And that's why they make $5 million a year.

And if you don't want to do that, go do something else. Now, I'm not doing that. No, no, but I think there's a job out there for you where you can be you.

It is my firm belief that ever since COVID, there's just a level of apathy that's run through everything. I mean, in every industry. It doesn't just have to be investment banking. Everybody wants to find a way to make a million dollars online and not have to actually put forth any effort. That's the new dream. Send me the job link because I'd like to do it.

Yeah, well, I always laugh with my wife. Apparently, you know, being here in Vegas, you look around, apparently there's some magic meeting where they just give away free money and we don't get invited to it. We actually have to work for her. Oh, they do. They do give it away. They do give it away. But it's it's you know, you have to put up collateral or you know, you're paying 21% interest and at a certain point, you know, you got to pay the piper.

And, and, and so look, look, I'm doing exactly what I want to do today. And I know we'll get to that, but I'm not making a million dollars a year. I'm not making, I'm making, you know, very, very little money. So it's a trade off and I've earned the right, I've earned the right to be able to do it.

But I also have to forego living like some jet setter lifestyle that we'd probably like to live if I was making, you know, a million bucks a year. I'd be, I'd have a net jets card if I was making a million bucks a year, but let's get a long way from that. Yeah. Let's, let's get to that. So was there a, was there a moment in your career and obviously your professional life where you were just like, look, I'm just burnt. I'm just cooked. There's gotta be a better way. Cause I'm just not finding what I need. Yeah.

Yeah. Well, there's two kind of inflection points. I made some money at Yahoo, but I'd always still had this thing in the back of my head. I want to be a stand-up comedian. And in 2004, I got to meet some people who were going to connect me with a way to be a stand-up comedian in LA. And I moved out to... I left Yahoo because I had money in the bank and I was still single. Thanks to Yahoo, I paid off my student loans and I put...

plenty of money in the bank, many years worth of expenses in the bank. And I was like, I'm going to go do standup comedy. That's what I'm going to do. And I, and I moved LA, my then girlfriend, now wife followed me shortly thereafter. And I did standup comedy every weekend for two years hosting at the improvs in orange County. Um,

and it was, it was, and I did, I had no idea how good that gig was while I had it, but I was doing the thing I really wanted to do at the mall. You're talking about the one at the mall. Yeah. The Brea, the Brea and Irvine improv. Now these were the old, both clubs have been, um, torn down and replaced since 2007 when I left, but I was doing that every weekend. And,

I was opening for David Tell, Kevin Nealon, Norm MacDonald, like legit big time headliners. Well, let's back up just a little bit, right? So here you are, you're MBA from Dartmouth and there's this burning feeling to be a standup comedian. So that's correct. What, what was it like? Like what about that? Like what? I don't know because it's the, it was the, it's the narcotic feeling you get when you make a room of 300 people wet their pants at the same time.

There's nothing like it. There, there is no, there is no high I've experienced like, um, like, like making a whole room of people laugh at the same time. It's, it's narcotic. And when did you, when did you know you wanted to do this? And when did you know you had an interest in it? When I told jokes in business school to a talent show, I just made fun. I co-hosted a talent show at business school and I made fun of my friends for 12 minutes and the room was just busted up. And, and it was like, oh, that's what I want to do.

That's what makes me special. And it was, this was, you know, pre, um, this is almost pre-internet. I mean, it was early, early, early in the internet and it was, you know, pre-social media today. Everybody wants to be a standup comedian. So like having this idea to be a standup comic wasn't,

you know, and, and to be somebody with a Ivy league NBA, like that was unique today. If you go on Instagram and look for, you know, Harvard NBA comedian, you'll find a dozen of them. I guarantee you. Was it last night? I heard last week, Conan got the Mark Twain humor prize. And well, he's a Harvard undergrad, but he was at the Harvard Lampoon. I mean like, and there's, you know, there's, there's hundreds of Harvard Lampoon graduates in the entertainment industry, but, but,

But yeah, so I wanted this. I had this idea in the back of my head and it was what made me special. It was also plagued me from a career management standpoint. I mean, you know, if I really was dedicated to the media business, I'd, I'd be doing something. I'd, I'd be running some big media property today, presumably if I hadn't blown myself up, but yeah,

So I went out to LA and I was doing stand-up comedy every weekend and for two years. And I was terrible when I got out there. I'd done maybe 30 comedy shows in my life. And then I'm opening for Daniel Tosh. It was brutal. But I got much better. But after two years, I got engaged to my wife and I was like...

I think I need a steady job. You know, I was doing really well in media and now I'm making, you know, not good money and the future is very uncertain. And it wasn't like I was such a natural that people were like, dude, this is your thing. You know, I mean, I was the funny guy in a business situation, but I wasn't like the funniest, like the improv. They're like, yeah, you're all right. Yeah.

Yeah, you're the best golfer at your club, but you're not going on tour anytime soon. Well, yeah, right. I mean, and it's great. It's great to hang out and golf and be a fun person to golf with. But if you want to make a living golfing, you got to come to Jesus on that, right? So that's when I started thinking about getting another job. And the phone rings one day, and it's a buddy of mine from Yahoo who said, would you be interested in joining this small social media company called Facebook? And I was like,

Yeah. And I told my wife someday this company could be as big as MySpace. And that was my big insight. Right. And of course it became a thousand times bigger. And I was fortunate to be on, on that ride. Uh, when I got there, there were 250 employees. When I left, when I left there were maybe 4,000.

And so it grew by 16X in that time. The audience, the global audience grew from like 25 million a month to like a billion a month. And of course, now it's over 3 billion. But I got to the point in 2011 where I was like, they asked me to move to Palo Alto from LA where I was running the West Coast sales team. And I just didn't want to do it. My heart wasn't in it. And that's that time where...

You were referring to before where you're like, I just don't want to do this. Isn't something that I want to keep doing, even though now I didn't know how big the company was going to become. And if I had, I probably would have stuck around because the, the amount of money I left on the table was, uh,

Yeah.

and to raise my children in an environment that I was excited about. And we went home in 2011. And what'd you do in Atlanta when you went back? Not much. Okay. So this is where I quit my job. I quit my job at 42. Some say I retired at 42. I didn't plan to stop working. I just was like, I'm going to stop doing this.

and meaning will find me. You can probably hear the sirens outside my street. Yeah, it's New York. Come on. The rough streets of the Upper West Side, man. Of course. Of course. It never stops. So I thought, you know, when I left my job, I was like, I'll figure it out, you know? But it's really interesting how easy it is to fill your day with lots of fun stuff that aren't work, you know? You work out. You get healthy. You travel. You read books. You spend time with your kids. You play a lot of golf. Like, life's pretty good until a certain point where you, like, wake up one day and you're like,

wait a minute, what, what am I doing? Who am I? I don't know how to answer the question. What do you do? Like, I feel like a loser. Like I'm very, very lucky, but I feel like a lucky loser right now. And eventually we'd have purpose. I had no purpose, no purpose. And eventually I even took another job I shouldn't have taken. I just sort of took a job that I thought would look good. And it wasn't, it wasn't a good fit. And it just,

Just wasn't, my heart wasn't in it. And so after a year of that, I said, I'm going to just, I'm going to, I, I've, I was, I was afraid, uh,

That is the word. I was afraid to try to do standup comedy again because I had failed. I had, I had quit. I didn't fail. I quit before. Just stopped. And I was ashamed that I like, what are people going to say? What would people that I worked with in the technology business think that I was going to go back? Did I look wishy washy, whatever. And of course, worrying about what other people think is the worst thing you can do. And so I just said, screw it. I'm going to write every day. I'm going to start going to open mics again. And this is in 2014 and,

and we'll see what happens. And so that's what happened. And I, and you know what, when you start, when you declare what you stand for, what you want to do, you eventually meet fellow travelers and you eventually find people who are gonna, you know, be your partners on the journey and you know, some way or be people that can, you can, you can help and they can help you back. And that's, and that's eventually what happened in Atlanta. And I started doing comedy again. I started doing a lot of comedy and,

um, got better. I've done, you know, every festival except for like the top two or three in North America. I've, you know, headlined around the country. I'm doing the thing that I want to do. I write every day. Um, you know, I've got a, I've got a, I'm, here's the thing, man. I'm very good at several different things. I'm a very good podcaster. I'm a very good comic. I'm a very good writer. Uh, and I'm a very good speaker too. I just did a great speaking event last week. Um,

I might even be great at speaking, but you know, as somebody, the guy that ran, the guy that ran the New York comedy festival, he's like, you know, you're good. You're very good. Right. And he goes, you know, that's not enough though. Right. You know, you have to be great. And that is absolutely true in the comedy business where everybody wants to be a comic or everybody wants to be a great musician. Everybody wants to be a musician. Well, if you want to be as musician who stands out, who sells tickets, who can support himself and his family doing that thing, you know,

You have to be great.

Very good isn't good enough. What you're looking for is my good friend, John Ashroff. Are you committed or are you interested? And I think everybody's interested. Hey, we want to put you on stage for 15 minutes. Everybody's going to laugh at what you say. I'm totally interested in that. You've actually got to go do the work to get good at doing it. Oh, I don't want to do that. Well, you know the old joke about the difference between committed and interested, right? Or committed and involved. What's that? Well, like you look at your breakfast plate, right? The

The chicken is involved. The pig is committed. And I think, you know, it's, what's, what's interesting is that kid at 28 years old, who, who was absolutely committed to his job because it was succeed or not eat, not pay your rent or, you know,

or go get some other job that you didn't want. Like, I think I'm seeing that that maniacal level of commitment really is what separates the people that are, that are breaking through in comedy from the people who are very good, but not breaking through. And it's, it's, it's very interesting to observe, you know, and these quick question while we're on the topic, who's the best?

Who's the best? Who's the best? Oh, my favorites are, you know, the, the Bill Burr, Dave Chappelle, um, you know, Gary Goldman is a genius.

Um, I just really admire smart comedy written by people who bring their own voice to the table. I think Bill Burr is, uh, Bill Burr is, is by far it not even close. He's my favorite because I love him so much because whether it's part of the act or I think it's genuine to him, he really does not give an absolute shit what you think about what he's saying. Yeah.

Yeah. And I think that's the level of detachment that you have to get to, to where you're like, look, I'm going to say, if you don't have that, then you're going to say what you think is going to be, they'll find funny. And audiences can smell that weakness. Let me tell you a Bill Burr story. I love that. So in 2005 or 2006, maybe, I was hosting for, I was starting to get decently good. And

I hosted for Bill Burr one weekend at the Ontario California Improv. Ontario's eastern LA. It's the Inland Empire. And we're talking one night in the green room, me and the middle comic and Bill Burr, and we'd gotten the topic of goals or whatever. And I said, well, what are your goals? And he goes, I want to be a great comedian.

And I said, you are a great comedian. At this point, he's working on his third special. He's working on the, if you ever seen the muffin smashing bit that he did back in like 2006 from a special, he was working on that that weekend. He was going to film it within a few months. And I said that I was like, you are a great comedian. He goes, no, I want to be one of the great comedians.

He's talking about Cosby, Carlin. Yeah, yeah, forever. He's talking about the pantheon. Yeah. Right? He's not talking about like, I want to be pretty good. He wants to be on Mount Rushmore of comedy. He's trying to get the job. Yeah, he wants to be on Mount Rushmore. And I remember just being like, oh, shit, man. This is the level of commitment that it takes to be the best. And I was both – I was like inspired and totally dejected because it's like –

You really have to have that if you want to be that good. So where are you on that scale? Where are you on that scale? You know where I am on that scale? I'm unfocused.

I am doing a lot of things very well, but I am not obsessive about one of them. And so I was having this conversation with my wife this weekend. It's like, I think, and to do this and to pick which one that I want to be absolutely committed to would, will require murdering two of my loves, which are, uh,

I don't know yet. You know, it's funny. I have a friend of mine that, you know, a good friend is that guy that calls you out when you need to be called out. And every time we talk about goals or talk about, you know, what we want to achieve, it's never what are you going to do or what are you willing to do to get there? The first question is always, what are you willing to give up to get there?

Yeah. Like what, what, what are you asking? Because you can't be, if you try to get to two places at once, you're not going to get to either. And that's always the first question. Yeah. The dog that chases two rabbits catches neither. No. Do you know who Morgan Housel is?

I don't. The psychology of money guy? The guy who wrote the book, The Psychology of Money? I know the book, but yeah, I don't know who he is. So that guy, he's been a financial journalist for a decade and a half or something like that. And then wrote this book that went on to sell, I think it sold like eight or nine million copies across all formats and across all markets. Gigantic book. You know, the average book sells like 10,000 copies, right? So this, he had this thing that stuck with me that was written in one of his articles, wasn't even in the book. And he said that,

to what is required to succeed isn't skill, it's scarcity. And so if you want to do something and be in the 0.1% of something of compensation of fame or whatever, you have to be incredible at something other people aren't incredible at. The world's got a million pretty good podcasts. The world's got a million

pretty good realtors. The world's got a million pretty good fill in the blank tennis players, athletes, artists are really good examples of that because their success is so public. You can make a really good living as the, you know, as the hundredth best accountant in New York city. You know, it's like,

In tennis or in golf, there's only one winner every weekend. And so what, what house was saying is like, you have to, you have to have something nobody else has, or you're going to, you're, you're going to be compensated commensurate to your uniqueness. And I think that's the thing to figure out, especially in a, in a category where there's a lot of people who want to succeed doing the same thing.

Do you see that in your world? Yeah. Well, so, yes. I mean, in real estate, which is what we are here in Vegas. And, you know, it's – how am I going to put this? It's – you just – you trade on reputation. Everything is reputation. And every deal gives you an opportunity to improve or diminish it.

And the better you, the elite people in my business, I don't think are any better at marketing properties. I don't think they're any better at writing, especially now in the age of AI, of writing descriptions or brochures or pamphlets or any of that stuff. I don't think anybody's any better. I think they are masters at managing their reputation.

And I think that's what makes the elite of the elite in my business, especially in between here, you know, a lot of friends in LA in this business and a lot of friends here in Vegas, because now our markets swap high-end clients so quickly back and forth. But the better you manage your reputation, the better you are. And again, it's about perceived value because what is perceived value? Perceived value is what people say about you when you're not there. Yeah. So yeah, that's your brand. That's the brand. Yeah. Yeah.

Yeah, that's everything in this business. And because I know some people that are very skilled at what we do, very knowledgeable. They're just, you know, they understand the math of the market. They understand leading indicators in different parts of the stock market, the bonds that affect our market in a different way, but yet they don't sell the most houses. They make these amazing YouTube videos about what's happening in the forecast for what's going on, but they don't do the best in the marketplace because they're

This particular industry respects reputation more than anything else. The best person is not always the best person here. It's all an illusion. What do you think a high, what do you think a high end client wants to

When, when they're looking to choose, I mean, they've got plenty of realtors to choose from, right? Yeah. Or plenty of partners in real estate transaction to choose from. Right. What do they look besides assuming they're going to have an outcome that's within 2% of each other, right? What are they looking for? To me, I genuinely believe a high end client is looking for the person they genuinely believe is going to get them where they want to go as far as accomplish their goals with the least amount of friction.

And in the high end, especially, they don't want to educate anybody. You have to kind of understand how high net worth people work, how they think, what their expectations are. They don't want to educate you to their needs. They just want somebody that understands those things. And I think that is the key to it.

We sold our house. We sold two houses, one in Atlanta and one in the mountains of North Carolina when we moved up here to New York last year, 2024. And we interviewed realtors and one of them who's great. There's a lot of very talented realtors in Atlanta and we're friends with a lot of them. And one of them said, well, what are you looking for besides, you know,

getting, getting the most for your property. And I said, I thought for a second, I was like, I'm looking for a person that when I see their car drive up, I'm happy to see him.

Like I know that they're going to make my day better because they're going to be solving my problems and not bringing me problems. With the least amount of friction. That's exactly what I just said. Yeah, that's right. That's yeah. But it's not just, it's not, it's not like friction. It's like a, it's a level of trust, you know, where you're like, I know this person is honest and they know what they're doing and they're committed to our outcome. Yeah.

well you know it's funny the one question that all of our people we have a lot of people i've got 585 agents that work for us here we have a very large company yeah big time but the number one question that i teach our people to ask that i think gets us more business than anybody else because nobody really asked this is everybody in this business gets so concerned with the first time you talk to a client on the phone let's say they're looking to buy a house so what do you want i want a three two i want this i want a pool i want it here what's your price point what's that they're just going through this

mental garbage checklist of the house and it's done. Well, you have to get all that information because you have to know what people want. But at the end of that conversation, the last question we always ask is forget the house.

You're moving your life here. You're relocating your life here. What else can we find out for you that you need to know about living here? I mean, do you need to know what the best club baseball team is? Do you have to know? I mean, is there a special needs program at this particular school for your child? What else can we chase down? Where's your church? Where's your gym? What clubs do you want to be in? Tell me about your life moving here and let us chase all that down for you. And all of a sudden it's like, what?

Whoa. Cause it stops being about the house and becomes about the client and their actual needs. This, I hear this. I, I, I speak to the wealth management industry pretty frequently. And what's happening in that business is, it's happening in many businesses in real real estate as well as money.

Most of the job has been commoditized by software. And of course, AI is... Hey, all listings are public now, right? I mean, you don't have anything proprietary there. And so it's who knows the client better. The differentiator is how do you understand the emotional needs of your client beyond just...

Hey, I'm going to beat the market by 0.5% and we're going to keep you in as little volatility as possible. Okay, that's nice. But anybody can license the software to do that. It's how do you keep me...

feeling okay about my life and my financial things in a way that somebody else that doesn't know me as well won't be able to provide. So I see that. I see a lot of similarities. And that's the answer that I always give on, you know, are you worried that AI is going to replace real estate agents? And I'm like, not at all because

Because I think that people, yes, a certain percentage of the public with high financial IQ and just the time to deal with it can make their own decisions and figure it out. But it's not about being replaced. I mean, AI could replace like, what do you call it? Title insurance or something like that, right? Yeah.

No, could it not? Let's hope not because I'm in a title company. But block, okay, let me say, it's going to change. Blockchain is going to change that industry significantly, right? Yes. The reason it hasn't already is because blockchain is not perfect. It still has imperfections. And when you say it's not going to replace realtors, but realtors or any profession that isn't using AI, and if you're not getting smart about...

If you're not getting smart about AI right now, you are falling behind. You can't see it, but you are losing ground on people who are doing it. I don't care what industry you're in. It very much in comedy and in writing right now too. I mean, this sounds so silly because I feel like I'm at the, um,

at the Boca del Vista, you know, senior learning center. But I took like, I took a Coursera AI course. I mean, I've been using these tools for a while, but I was like, I need to start at the basics and really start to kind of build my AI skill, like,

from a foundation and start getting smart about all the different tools out there. And if you're not doing that in your industry, you're going to get smoked. It might not happen this year. It might not happen next year, but it is going to happen. It's so funny when I run into people, I'm like, oh yeah, I use AI every day. And they're like, yeah, use it to give me social media posts. I'm like, dude,

i took our p ls and all of our numbers for the last three years i uploaded had to completely analyze our business models of all of our stuff give me fine areas where we weren't paying attention and could improve it and it did what a consultant 10 years ago would have done in a month it knocked out in five minutes it's incredible it's incredible and i mean it's it's only going to get more interesting i was using

two or two and a half years ago started poking around with different models to see, okay, well, can it help me write? Can it help me tell jokes? Can it find, and not like write jokes? Cause it can't, humans can't imitate other humans voices very well. And AI can't do it either. I mean, in writing, um,

So it's more like, hey, give me another way to say this phrase, you know, as opposed to, and the improvement in the last two years has just been mind blowing. So like, whatever, again, whatever industry you're in, I mean, get on it, guy, you know? Well, you, but you've written a book. So have you, have you load, have you loaded your book into an AI assistant said, read this and now give it back to me in my own voice? Yeah.

Cause that's a pretty big sample. What I'll do, what I'll do is say, um, okay, these, this is my re and, and writers talk about this. And, and I mean, um,

One of the hardest things for me, what I have a sub stack, um, at words.paulhollinger.com. Um, and what I, what I try to do is write about life and happiness and success in a way it's, it's, it's called reasonably happy, the skeptics guide to achievable contentment. Right. And so I try to write entertaining, funny stories that are generally like things that happened to me or some observation I'll make in the world.

and I'll tie it back to some lesson, right? It's secular sermons, if you will, that are, you know, have some potty jokes and are pretty damn funny if I've achieved my goals. And so what I'll do is say, here's, you know, here's 50 essays I've written over the last however many years, right? Why am I picturing Larry David with a fable on the end? Well, there you go, right? Curb your enthusiasm, but with a point. Well, it's something like that. It's something like that.

And you feed it, you upload what you've written and say, this is my voice. And I'm interested in writing about, take an item from the news, like tariffs. And I'm not looking to state a point of view on tariffs. I'm just saying, give me some thoughts on what's a point of view on tariffs that's interesting. Or I think I want to write about tariffs. Give me three examples of why tariffs could be good or tariffs could be bad.

just to start the mental exercise of getting things going. And then, you know, I think what's one thing that AI is really good for in writing is editing. I'll spend a few hours writing something and I'll take, you know, an 800 word draft or whatever it is and upload it to multiple different GPTs and say, tell me how I can make this better.

Can I make it shorter? Can I add more examples? Can I use better language? Am I repeating words? Things like that. Like it's, it's, it's an editor. It's a really effective editor. It's not perfect, but it's very, very effective. And so when I actually take it to my human editor at some point, I've not, I'm not wasting his time. I'm sitting, I'm giving him a very well polished draft and he always has things that he's

he can help me improve, but, but everything gets better because I've done the work with something to help me think through, um, you know, getting it to 95% before I get it to a hundred percent. Does that make sense? It does. But the point that we were talking about earlier is,

with AI not replacing that connection. Like you can use it to write, but it can't create your tone and it can't, it can't deliver that material in a way that you can. It can't quite, it's not there yet. I mean, it will get there, but it will get there. But again, I don't, I don't look, I'm, I was having this conversation with a, with a comedian, a very smart, very smart, very funny comedian named Zane Sharif in Atlanta today. And Zane, uh,

What I love about him is he writes beautiful, well-crafted jokes. And we were both lamenting how the crowd work videos are what Instagram and TikTok, what their algorithms promote just because that's who knows why. Matt Rife. Matt Rife, exactly. And we both acknowledge Matt Rife's success and that Matt Rife works hard, but that's not the kind of comedy that either of us wants to do.

Plus he's 10 times better looking than either of us. So screw Matt, right? So, so, so, but we're sitting there and like, I think there could be AI could completely obliterate us and make us completely unnecessary comedically, or it might inspire in people a reinvestment and a, and a, and a deeper interest in bespoke,

handcrafted goods in handcrafted hand woven comedy. Let me tell you, let me tell you why you're safe. I'm going to tell you why you're safe, Paul.

For the same reason that I'm safe. And I tell my kids this every day. And if you look at, if you look at the generation of teenagers, right? If you look at a teenager, you can't see their face because all you can see is this as they look at their phone. I got two of them. Yeah. And all they do is look at their phone. I tell my kids, if you want to have a competitive advantage, you want to have that thing in 15 or 20 years, that's going to make you better than everybody else. It'll be the ability to look in another human and connect with them on a one-on-one personal level.

because most of your friends that are spending all of their time staring at a screen won't have it. I think your father knew that at that dinner table when he was making everybody ask questions, teaching you how to communicate and connect with others. And I think being a great communicator

And any industry is going to keep you relevant regardless of what AI does. And I can't imagine a field where it's more important to be a great communicator than comedy. Look, I don't think you can succeed if you lack sincerity. And people taking shortcuts is still very transparent.

We'll see how that changes over time. Yeah. All right. Well, let's switch gears a little bit. If you could go back, because literally my whole podcast is a love letter to my dipshit 27-year-old self and trying to, if I could go back. I got a book coming out November 5th called Also Escaping the Drift. It is a user's manual to my dipshit 27-year-old self. But if you could go back and talk to young Paul, hustle and bustle,

What advice would you give him now that you've lived through the life? What would, what would you tell him? I maybe don't leave Facebook in 2011. Maybe don't do that. Build time machine is what you tell them. Maybe stick around for three or four more years. Fair. You know, look, my life has worked out. I have a wife who loves me, who my love, and I live with my kids who tolerate me. So, so I'm, I'm doing very, very well. I've, you know, I think it was great. And, and,

Is around 27. And this is not a coincidence. I think I started to become a better person. I think it's because my brain was done, you know, fully growing. But I think around that time, 26, 27, I was starting to go like, oh, if, if, if I want to be successful, I need to work hard. And if I work hard in general, on average, Keteris Paribus, all else equal good things happen. And so, um,

I think sometimes those are lessons, especially guys just have to learn. You can hear your dad can beat you over the head with all this advice.

And even your dad's friends who maybe you'll listen, I, you know, I've got, I'm sure you've got your friends who you talk to my kid and just, you know, and, and you'll ask your friend, will you talk to my kid? Cause my kid won't listen to me and your kid won't listen to you. And maybe we can help each other out. But some of these things, young people just have to learn on their own. And I, and I hope that young people are still learning 24, 25, you know, whatever, if you work hard.

all else equal good things will happen well dude you know that's why i love like like alex hermosi i love his message that he puts out now like he put something out yesterday and says normally the most successful person in a room is the person that's willing to look stupid the longest because they're willing to make those mistakes there's i think epictetus said something like that like your your willingness to fail is

is a key to your success. Like if you're worried about looking stupid, you're never gonna try anything that you're not already good at, which means you're never gonna grow. - Well, to that point, to that point, for everybody listening to this, that's got some dream, whatever it is that they have pushed to the side, chasing the conventional way to the almighty dollar,

What do you think your, and I'm not talking about where would you be working? I'm talking about what would your satisfaction in life with your life? What would your relationship with your wife and your kids be? Had you not chased this dream? I, I,

I, you know, when, when the market took a dive that first week of COVID, we were on spring break and very nice circumstances in the Caribbean. And I remember looking, you know, seeing our net worth go down by whatever, 30% in a week. And I thought to myself, I guess I'll get a job, you know, like I think that I, I, I

If we lost 50% of what we had tomorrow, God forbid, I think we'd be okay. Because I'd go find something worth doing and I'd do the best job I possibly could. The reason I chose to chase this dream is because I wanted to avoid the deathbed regret of

of wanting to know the answer to the question, what would happen if I gave it my all? Now, I haven't given it my all yet, and I'm going to keep giving it my all, but I've given it everything I've had up to this point to about 98.5%.

And so, you know, if I'm pretty close to having an answer to what would happen if I gave it my all and you know what happens, you get a lot better. You, you learn a lot, you meet a lot of interesting people, you get to do the thing and the reward for trying and giving it your all is the doing of the thing, right?

Rewards past that are not guaranteed, especially in the creative arts. And yes, the harder you work, the more likely you are to succeed. The more focused you are, the more likely you are to succeed. But in the end, the reward is getting better at something you care about. - And I think that's, we'll wrap it up with that. Paul, if they wanna find more of you, man, how do they find you?

Uh, words.paulollinger.com is P-A-U-L-L-O-L-L-I-N-G-E-R. That's my writing. You'll see a lot of the podcasts there and I promote the other stuff I'm doing there as well. Also on all the social networks. So search for me, baby. Well, man, we will. And if you're ever, well, I'm sure you'll be in Vegas, man. That's what you do when you come out, make sure you stop by and say hi. I sure will. Thanks for having me. Well, man, if guys, it's,

thanks for joining us today with that and if you listen to that man what i'm taking away from that is we get so focused on chasing the almighty dollar on chasing the things that we think we're supposed to do but as long as you can maintain two things this is what i'm taking away from paul number one never lose sight of that thing inside you that is calling you that you always want to be part of go try it do it because what's the worst that could happen

And as long as you hang on to eternal optimism, that no matter what happens, you'll just kind of be able to figure it out. You're going to be okay. We'll see you next week.

What's up, everybody? Thanks for joining us for another episode of Escaping the Drift. Hope you got a bunch out of it, or at least as much as I did out of it. Anyway, if you want to learn more about the show, you can always go over to escapingthedrift.com. You can join our mailing list. But do me a favor, if you wouldn't mind, throw up that five-star review, give us a share, do something, man. We're here for you. Hopefully, you'll be here for us. But anyway, in the meantime, we will see you at the next episode.