Paul Ollinger
Appearances
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
We were on the cusp of the, of, of technology and music in like 1998 99 when things, you know, we were, we were, 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. Um, but
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And I went and I interviewed 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Um, there's that word again, gang, the, 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 when you're 28 and you don't have kids and you're single and like, what else are you gonna do?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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. You know, when, when, when Yahoo bought launch, we just, they just kept us alive. You know, we'd, we'd gone through the, the busting of the.com bubble, like, like everybody else.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And when Yahoo bought us, we had laid off, the company had laid off four fifths of the employees and I was lucky to make the cuts and, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Well, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And it was like, you know, anybody with a heartbeat could be a realtor or, um, you know, it's still that way. Well, being the mortgage business, well, this market's probably making it a little harder, right? So what a downturn does is sort of gets you back to right size.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And so 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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, even if they weren't the most talented people. And I would count, I mean, I'm a talented guy.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 work. That's how they find out who's committed and who's not. Is it right? Well, is it unhealthy? Can be. But there's a lot of jobs that aren't investment banking out there waiting for you.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So 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
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 um and you know I was always part of a gang it was it was uh It was a busy, crazy household.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Send me the job link because I'd like to do it.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 a million bucks a year. I'd have a NetJets card if I was making a million bucks a year, but we're a long way from that.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 standup comedian. And in 2004, I got to meet some people who were going to connect me with a way to be a standup comedian in LA. And I moved out to, I left Yahoo because I had money in the bank and I was still single.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 stand-up comedy. That's what I'm going to do. And I moved to LA. My then girlfriend, now wife, followed me shortly thereafter. And I did stand-up comedy every weekend for two years, hosting at the Improbs in Orange County.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I don't know, because 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 is no high I've experienced like making a whole room of people laugh at the same time. It's narcotic.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
When I told jokes in business school to a talent show, 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 it was like, oh, that's what I want to do. That's what makes me special. And this was almost pre-internet. I mean, it was early, early, early in the internet and it was pre-social media.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Today, everybody wants to be a stand-up 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I mean, if I really was dedicated to the media business, I'd be doing something. I'd be running some big media property today, presumably if I hadn't blown myself up. 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
We weren't rich, but we had everything we needed. And there was lots of people around. And as crowded as it could be, I always knew I was part of something. And you wouldn't have put it in those terms when you were a kid. But looking back, having been a part of that gang, you have a security built into you that people who don't have that you know, maybe don't experience or at least as a child.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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. I was doing really well in media. And now I'm making 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Well, yeah, right. I mean, and that's and it's great. You're 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, there's a whole different level. Got to come to Jesus on that, right? Yeah.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And I was fortunate to be on that ride. When I got there, there were 250 employees. When I left, there were maybe 4,000, you know? And so it grew by 16X in that time. The audience, the global audience grew by from like 25 million a month to like a billion a month. And of course now it's over 3 billion.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 amount of money I left on the table was ridiculous. Yeah, it had to be massive. But my stock options were already worth more money than I ever thought I would ever need or want, but I probably would have doubled what I had if I'd stuck around. Yeah. But I bailed.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So I went home. I moved back to Atlanta where I grew up and my parents were there and they were old and sick. And I had an opportunity to play a role in their life and to raise my children in an environment that I was excited about. And we went home in 2011.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Not much. Okay. So this is where 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So I thought when I left my job, I was like, I'll figure it out. But it's really interesting how easy it is to fill your day with lots of fun stuff that aren't work. You work out, you get healthy, you travel, you read books, you spend time with your kids, you play a lot of golf. Life's pretty good until a certain point where you wake up one day and you're like,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And it wasn't, it wasn't a good fit. And it, 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. 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?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
What would people that I worked with in the technology business think that I was going to go back? That 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 we'll see what happens.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 going to 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And that's, and that's eventually what happened in Atlanta. And I started doing comedy again. I started doing a lot of comedy, 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,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 have to be great. Very good isn't, isn't good enough.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 chicken is involved. The pig is committed. Yes.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And I think what's interesting is that kid at 28 years old who was absolutely committed to his job because it was succeed or not eat, not pay your rent or go get some other job that you didn't want. 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 Gullman is a genius. Um, I just really admire smart comedy written by people who bring their own voice to the table.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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, uh, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And, you know, but when you get to high school, you know, 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. which is you want to make your own way, but at the same time, the teachers know who you are. Your older sisters tease you in the hall. Her friends are like, oh, look at him.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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, I was like, you are a great comedian. He goes, no, I want to be one of the great comedians. he, he was, he's talking about Cosby Carlin. Yeah.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Forever. He's talking about the Pantheon. Yeah. Right. He's not talking about like, I want to be pretty good.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
He's trying to get, and I remember just being like, Oh shit, man, this is the level of commitment that it takes to be the best. Like, and I was, I was both, I was like inspired and totally dejected because it's like, You really have to have that if you wanna 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 am unfocused.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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, I don't know yet. Yeah.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 thing.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 100th best uh accountant in new york city you know it's like but in tennis
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 gives you a safety net. I think that was a very big part of my childhood. Childhood dinners were The dinner table at our family was very raucous.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 gonna 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
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Yeah. So yeah, that's your brand. That's, that's the brand.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
What do you think a high-end client wants? When they're looking to choose, I mean, they've got plenty of realtors to choose from, right? Yeah. Or plenty of partners in a 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?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Whenever one of my siblings would have a friend over to spend the night, they'd all 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...
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
We sold our house. We sold two houses, one in Atlanta and one in the mountains of North Carolina. Uh, when we moved up here to New York a year last year, 2024, and we interviewed realtors and one of them who's great. We, we, there's a lot of very talented, uh, realtors in Atlanta and, and we're friends with a lot of them. And one of them said, well, what are you looking for besides, you know,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 them. 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Yeah, that's right. But it's not like friction. It's a level of trust where you're like, I know this person is honest and they know what they're doing and they're committed to our outcome.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Yeah, big time.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I hear this. I speak to the wealth management industry pretty frequently. And what's happening in that business is, and it's happening in many businesses in real estate as well, is most of the job has been commoditized by software. And of course, AI is, and with, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
won't be able to provide. So I see that. I see a lot of similarities.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
But it's not about being replaced. I mean, AI could replace, what do you call it, title insurance or something like that, right? No, could it not? Let's hope not because I don't want a title company. But blockchain is going to change that industry significantly, right? Yeah.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
It still has imperfections. Sure. 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 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I mean, this sounds so silly because I feel like I'm at, at the, 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,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
just 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I mean, in writing. So it's more like, Hey, give me another way to say this phrase, you know, as opposed to, and, and the improvement in the last two years has just been mind blowing. So like,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 yeah and now give it back to me in my own voice because that's a pretty big example 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
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 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 50 essays I've written over the last however many years, right?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Well, there you go, right? Curb your enthusiasm, but with a 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I'm just saying, give me some thoughts on what's a point of view on tariffs that's interesting. Or I think this is, you know, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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. It's an editor. It's a really effective editor. It's not perfect, but it's very, very effective.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And so when I actually take it to my human editor at some point, I'm not wasting his time. I'm giving him a very well-polished draft. And he always has things that he can help me improve. But everything gets better because I've done the work with something to help me think through getting it to 95% before I get it to 100%. Does that make sense?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
It can't quite. It's not there yet. I mean, it will get there. It will get there. Look, I was having this conversation with a comedian, a very smart, very smart, very funny comedian named Zain Sharif in Atlanta today. And Zane, what I love about him is he writes beautiful, well-crafted jokes.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And we were both lamenting how, you know, the crowd work videos are what Instagram and TikTok, you know, what their algorithms promote just because that's who knows why.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 Rife. But we're sitting there and I think there could be
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
AI could completely obliterate us and make us completely unnecessary comedically, or it might inspire in people a reinvestment and a deeper interest in bespoke goods, in handcrafted, hand-woven comedy.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And again, we had very stable upbringing, but it wasn't like he had money falling out of his pockets.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Uh, 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. Um, you know, look, my life has worked out. Uh, I have a wife who loves me, who my love, and I live with my kids who tolerate me. Um, so, so I'm, I'm doing very, very well. I've, you know, I, I think it was great. And it,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I, you know, 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?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 hope that young people are still learning 24, 25, whatever. If you work hard, all else equal, good things will happen.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I think Epictetus said something like that. Your willingness to fail is a key to your success. If you're worried about looking stupid, you're never going to try anything that you're not already good at, which means you're never going to grow.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
That's 100% right. And I think it made me a very earnest person. It made me very hungry for attention. But to be my own person and have something to say and distinguish myself from my older brother and my family in general, you know, when I was a freshman, my brother Cole was a junior in high school.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I. You know, when the market took a dive that first week of COVID, we were on spring break in very nice circumstances in the Caribbean. And I remember looking, you know, and 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...
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
if we lost 50% of what we had tomorrow, you know, God forbid, I think we'd be okay because I mean, I'd go find something worth doing and I'd try to do, I'd do the best job I possibly could.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Um, and you know, the thing I didn't, the reason I chose to chase this stream 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 and a half percent.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 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. Rewards past that are not guaranteed, especially in the creative arts.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Words.paulollinger.com is P-A-U-L-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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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,
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
That's right. That's right. Well, I really was available to them, you know, but when I got my braces off, maybe, you know, things things start to improve a little bit. So 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 when, you know, in the next few months, he's he's right at that point where he's about to break out, you know?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So expensive.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Well, my, my brother was a very, uh, 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, you know, close in proximity and in age. Um, he was a very good student. Um, he was a very good basketball player.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 ended up doing all that. And I was motivated.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And I think there's also part of this thing that you want to achieve because I wanted to get good grades because I wanted to know that I was okay. 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 my, you know, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I went to Rhodes College in Memphis, Tennessee. And then I ended up going to business school at Dartmouth.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
I was like 250th employee at Facebook. So still pretty early. And if I'd been smart, I'd have stuck around another few years and we'd be talking on my yacht right now. But I was very, very fortunate to get there when I did. And I worked with a lot of good people. Before I worked at Facebook, I was very fortunate to
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 because 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Yeah, I got it. 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
You get the name brand credential and you get a network and the network is very helpful. 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 paid off for me over and over again throughout my career, both in business and even in comedy.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So when I got to Dartmouth, I was like, well, I can really do what I want to do. What excites me? 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?
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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, you know, a few years later when I had some industry experience, I wouldn't have gone to that job.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
So we were perfectly, you know, uh, inexperienced 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, that, 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And then I was out in LA and then Yahoo kind of brought us into the fold. And I stayed on the ad sales team at Yahoo for a long time too.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 was like, okay, I raised money at my college for three years after graduation. I sold ads for the Dartmouth, the business school student paper.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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. 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 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 today still.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 6th 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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 80, 85 hours a week. Because why not? I was single. I had no kids.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
My roommate at the time was working on Wall Street. He was working 100 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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Well, you know, there's a lot of things that were going on that we, 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, and I think what I needed to do was just not take no for an answer and not allowed myself to be ignored.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
What's happening, John? Thanks for having me.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
And I had friends that... I went to business school with who were now in marketing. I would call them. I would call friends of theirs. I would call people who graduated four years before me and say, you don't know me, but I'm doing this thing. I'd love to talk to you. And if you can't tell me, if you can't help me right now, can you point me in the right direction? That kind of thing.
Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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.