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.
Trend
recordings per month · last 12 monthsNo recordings in the last 12 months.Older appearances are listed below; set an alert to hear about the next one.
Appearances
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 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.
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.
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.
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.
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.
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.
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.
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.
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, 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Showing 61–80 of 141 · page 4 of 8
← Previous
Next →