Paul Ollinger
speaker
141 appearances
1 recordings
1 series
first heard May 2025
last heard May 2025
Paul Ollinger’s voice in public audio — every appearance, attributed to the second.
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Appearances
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,
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.
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?
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.
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.
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,
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.
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 have to be great. Very good isn't, isn't good enough.
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.
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.
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.
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, 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.
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.
Forever. He's talking about the Pantheon. Yeah. Right. He's not talking about like, I want to be pretty good.
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.
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.
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 thing.
Showing 81–100 of 141 · page 5 of 8
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