Escaping the Drift with John Gafford
Paul Ollinger: From Sibling Rivalry to Comedy and Career Success
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
Full Episode
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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