Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
Thu, 29 May 2025
Comedian, speaker, and author Paul Ollinger takes us on a laughter-filled journey through his life, offering a candid look into his experiences growing up in a large Catholic family in suburban Atlanta. Known for his sharp wit and engaging storytelling, Paul reflects on how sibling rivalry and lively dinner table discussions crafted his communication prowess and competitive spirit. These traits propelled him through academic achievements and early career successes at Launch.com and Facebook, all while he learned to appreciate every step of the journey rather than waiting for a singular definition of success. Shifting gears, we uncover the intricacies of navigating career transitions, particularly in the ever-evolving media landscape. Paul vividly recounts his pivot from a comfortable position at Yahoo to chasing his passion for stand-up comedy in Los Angeles, a decision that led him to a pivotal role at Facebook during its exponential growth phase. His story illustrates the delicate balance between following one's dreams and maintaining practicality in the face of life's uncertainties, offering listeners valuable insights on resilience and adaptability. As we wrap up our conversation, we explore the crucial role of AI and technology in modern industries like real estate. Paul shares his unique approach to real estate transactions, emphasizing the importance of trust and emotional intelligence in building lasting client relationships. We also discuss how professionals can stand out in a commoditized market by focusing on clients' holistic needs and the necessity of ongoing education to keep pace with AI advancements. Join us for a thought-provoking episode that combines humor, personal reflection, and industry insights to inspire listeners on their paths to happiness and success. CHAPTERS (05:27) - Sibling Rivalry and Achieving Success (10:09) - Navigating Early Career Success in Media (15:25) - Navigating the Corporate Landscape (24:25) - Career Transition and Personal Reflection (36:29) - Achieving Success Through Uniqueness (42:36) - Real Estate, AI, and Industry Innovation (50:17) - The Power of AI in Writing (59:52) - Audience Engagement for Escaping Drift 💬 Did you enjoy this podcast episode? Tell us all about it in the comment section below! ☑️ If you liked this video, consider subscribing to Escaping The Drift with John Gafford ************* 💯 About John Gafford: After appearing on NBC's "The Apprentice", John relocated to the Las Vegas Valley and founded several successful companies in the real estate space. ➡️ The Gafford Group at Simply Vegas, top 1% of all REALTORS nationwide in terms of production. Simply Vegas, a 500 agent brokerage with billions in annual sales Clear Title, a 7-figure full-service title and escrow company. ************* ✅ Follow John Gafford on social media: Instagram ▶️ / thejohngafford Facebook ▶️ / gafford2 🎧 Stream The Escaping The Drift Podcast with John Gafford Episode here: Listen On Spotify: https://open.spotify.com/show/7cWN80gtZ4m4wl3DqQoJmK?si=2d60fd72329d44a9 Listen On Apple: https://podcasts.apple.com/us/podcast/escaping-the-drift-with-john-gafford/id1582927283 ************* #escapingthedrift #paulollinger #comedy #speaker #author #laughter #life #candid #catholic #family #suburbanatlanta #siblingrivalry #dinnertable #communication #competitivespirit #academicachievements #careersuccess #launch.com #facebook #medialandscape #careertransitions #realestate #ai #technology #industryinnovation #personalreflection #happiness #success #resilience #adaptability #networking #professionalgrowth #fulfillment #passion #stand-upcomedy #losangeles #corporateworld #strategicnetworking #economicshifts #exponentialgrowth #globalaudience #unique #reputationmanagement #high-endclients #perceivedvalue #reputation #realestatetransactions #trust #emotionalintelligence #relocation #commoditizedmarket #wealthmanagement #personalizedservice #ongoingeducation #adaptation #writing #editing #humanelement #communication #humanconnection #hardwork #sincerity #resilience #perseverance #audienceengagement #escapingdrift #insights #takeaways #mailinglist #five-starreview #meaningfulcontent
Chapter 1: What role did sibling rivalry play in Paul's 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.
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 John 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 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 gonna get you to that next level but my guest today is somebody that that when i saw this come across my desk i thought what a great message to share with you guys because this guy
as 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.
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 look forward to having an excuse to come out and hang with you guys you do so i i know that look you've done some amazing stuff reading the bio here and going through it and i always like to say think that success leaves clues and i'm always interested in the nature versus nurture where i almost always start these these interviews so tell me about a young paul ollinger tell me about young paul the uh the either the hero origin story or the villain
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Chapter 2: How did Paul transition from corporate to comedy?
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.
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, 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.
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.
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Chapter 3: What insights did Paul gain from his early career at Facebook?
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...
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 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.
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,
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Chapter 4: How does one navigate career transitions effectively?
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 halls available.
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?
Well, let's ask this because, yeah, braces is a huge deal. And I had 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, 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.
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.
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.
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Chapter 5: What unique approaches does Paul suggest for success?
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.
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
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 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.
were used 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 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.
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Chapter 6: How is AI shaping the future of industries?
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 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.
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?
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.
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.
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.
I mean, that's got to be, so here you walk into a job, 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?
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Chapter 7: What is the importance of resilience in achieving goals?
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.
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.
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.
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.
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.
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.
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? Because 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 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.
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Chapter 8: How can professionals stand out in a commoditized market?
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... 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.
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 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
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 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, 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?
Yeah, but I think even then, I think your upbringing showing through right there because I think you were probably, you left your tribe at home and that side of it's always been appealing to you even in business. 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.
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