I Used to Be Somebody: (Un)Retirement Lessons Learned

Back to Blog

Subscribe to the podcast on
Apple Spotify or More

Paul Ollinger Interview: Former Facebook Exec Turn Comedian -- “Now I’m Me!”

Diana Landau | October 05, 2021

 
Carl talks with Paul Ollinger, an author, stand-up comedian and host of the Crazy Money podcast. He also has an MBA from Dartmouth’s Tuck School and was one of the first 250 employees of Facebook, where he served as VP of West Coast Sales. You could say Paul is on his third successful career at this point.
 
Paul grew up in a suburb of Atlanta, one of six kids from a big Catholic family. His father was an engineer for a Georgia utility company and although there was money, his parents were frugal and there was a strict budget. Paul felt that anxiety about money as a kid and as his careers at Facebook and in comedy rewarded him, he realized that no matter how much money you make, you can still feel stressed about it. His podcast, Crazy Money is not about how to make more money but about exploring the connection between money, happiness, work and meaning.
 
Paul’s path to success has been anything but linear. After college and a focus on business, Paul made his first attempt to become a stand-up comedian and became a host at LA comedy clubs, opening for many big names at the time. Then he got married and started thinking about a more stable career for raising a family. A friend asked him if he wanted to be part of this new social media start-up company—he became the 250th employee at Facebook.
 
After relocations to other cities and promotions, in 2012 Paul left his very financially secure job and decided to put down roots for his young family. Atlanta was home. For the first few years, Paul wasn’t sure what to do. “I didn’t go toward anything after I quit my job.” He then worked for a year but knew it wasn’t the right fit. He decided to face his real fear—would he fail if he went back to comedy? He started writing every day, got himself into the comedy scenes in various cities and committed to his new path.
 
Carl agreed that forging an entirely new career is scary—but it’s invigorating! Paul noted that the nervousness means you really care about what you’re doing because you want to figure it out. “Breaking ourselves out of the mode by which we’ve been measuring ourselves for past decades is highly disconcerting, but it’s what you need to do to find a new path in the post-corporate world.” Now in 2021, Paul has a very successful career as a stand-up comedian, author and speaker, and is also busy hosting his podcast. From a young age, Paul has been driven to push himself to new heights. “I just want to get so much better at everything I do!”
 
(Un)retirement advice from Paul Ollinger:
  • “Change your metrics! The way you’ve been evaluating your life in the work world will be very different afterwards. And if you’re looking for external validation like bonuses and titles and being known in the industry, that goes away…..YOU have to be the one to monitor your own progress.”
  • “We need to have a longer term ‘through line’ in our lives. That’s where the meaning lives. The sooner you can get on it and it feels authentic to you, the sooner you’ll get to this is me, this is my life.”
  • “Let go of worrying about anyone else. You are doing (this new path) for you. The world may not notice. Do it because it’s an expression of who you are without any external reward.”

 

• More about Paul Ollinger and his podcast Crazy Money: https://paulollinger.com/about/
• Sponsored by: lovemyheartstudy.com or call (866) 955-1594

 

Diana Landau is the Content Wrangler for Pickleball Media. After 15 years in corporate marketing, in 2012 she pivoted to write and wrangle content for Niche Media's weekly blog. She now manages the “I Used to Be Somebody” weekly blog.

 

Tags:    blog   facebook   executive   unretirement   comedy   paul ollinger   crazy money   dartmouth   career  

    Categories

    Show All (74)
    (un)retirement (1)
    2022 (1)
    adversity (1)
    advice (2)
    ageism (1)
    Alan Newman (1)
    andy levine (1)
    andy robin (1)
    Anheuser Busch (1)
    anne da vigo (1)
    anniversary (1)
    architectural designer (1)
    Arnold Schwarzenegger (1)
    artist (1)
    ascenium (1)
    attorney (1)
    Audrey Hitchcock (1)
    author (10)
    baby boomer (3)
    baby boomers (1)
    baking (1)
    banking (1)
    barry pincus (1)
    bary pincus (1)
    baseball (4)
    baseball cards (1)
    basketball (1)
    beer (1)
    best-seller (1)
    bestseller (1)
    bestselling (2)
    best selling (1)
    bestselling author (1)
    blog (70)
    blog (4)
    Blog (1)
    Bob Franceschelli (1)
    bob tuschman (2)
    Bob Tuschman (1)
    Bob Vogel (1)
    bonus episode (1)
    book (2)
    boomer (5)
    bo sacks (1)
    brewing (1)
    budget (1)
    business tips (1)
    caffeine (1)
    cancer (1)
    career (6)
    carl landau (1)
    Caroline Ceniza Levine (1)
    ceo (1)
    CEO (1)
    cfo (1)
    CFO (1)
    challenges (1)
    changes (1)
    charity (1)
    cheesemaker (1)
    chef (2)
    Chris Farrell (1)
    chris welles (1)
    cinde dolphin (1)
    club change (1)
    coffee (1)
    coffeehouse (1)
    collector (1)
    collegescholarship (1)
    comedian (1)
    comedy (4)
    comfort zone (1)
    community (1)
    content marketing (1)
    coors (1)
    Corky Logue (1)
    craft brewing (1)
    crazy money (1)
    cycling (1)
    Dan Blank (1)
    Dan Kennedy (1)
    Dan Rudd (1)
    dartmouth (1)
    dealers choice (1)
    Debb McColloch (1)
    debb mccolloch (1)
    Deborah McColloch (1)
    Detroit (1)
    devon zagory (1)
    director (1)
    Doctor Who (1)
    documentary (1)
    Donald Trump (1)
    dream job (1)
    dreams (1)
    Dr James Beckett (1)
    Duke (1)
    Ed Casey (1)
    editor (2)
    embracing change (1)
    entertainment (1)
    entreprener (1)
    entrepreneur (8)
    entrepreneur (1)
    entrepreneur (1)
    episodes (2)
    Exec (1)
    executive (4)
    executive editor (1)
    EZ Pawn (1)
    facebook (1)
    farm to table (1)
    film (1)
    finance (2)
    finances (1)
    financial advisor (1)
    financial planning (1)
    financial security (1)
    first woman (1)
    food (3)
    food network (1)
    Food Network (1)
    foundation (1)
    future (1)
    General Manager (1)
    Georgetown (1)
    giants (3)
    Giants (1)
    golf (1)
    grace (1)
    halloffame (1)
    henry schulman (1)
    high times (1)
    hope (1)
    horses (1)
    housing (1)
    humor (1)
    hypnotherapy (1)
    improv (1)
    interview (53)
    Interview (1)
    interview (52)
    investor (1)
    ironman (1)
    ironman competitor (1)
    Jack Gallagher (1)
    Jill Baker (1)
    jim roddy (2)
    Joan Ryan (1)
    joan ryan (1)
    job (2)
    joe pulizzi (2)
    journalism (4)
    Kerry Hannon (1)
    Larry David (1)
    law (1)
    legend (1)
    lessons (2)
    lgbtq (1)
    licensing (1)
    life lessons (1)
    life of freedom (1)
    local (1)
    luck (1)
    magazine (3)
    magazines (1)
    major league (1)
    marketing (3)
    mark shaiken (2)
    Mark Shaiken (1)
    meditation (1)
    Melissa Davey (1)
    memoir (1)
    mental health (1)
    merchandise (1)
    Miami University (1)
    michaela oconnor abrams (1)
    michael clinton (1)
    Michela OConnor Abrams (1)
    Midtown (1)
    mike branon (1)
    mike drak (1)
    mike krukow (2)
    Mike Murphy (1)
    mini-retirement (1)
    moira mcgarvey black (2)
    mo nard (1)
    Money magazine (1)
    Mozzarella di Bufalo (1)
    multi-media giant (1)
    music (1)
    naps (2)
    naps (1)
    NBA (1)
    Neil Haley (1)
    Neil the Real Deal (1)
    new beginning (1)
    new year (1)
    nonprofit (1)
    novel (1)
    NYU (1)
    painter (1)
    passion (2)
    passions (1)
    patrick mulvaney (1)
    paul ollinger (1)
    PBS (1)
    People Magazine (1)
    performer (1)
    philadelphia (1)
    photography (2)
    pickleball (5)
    pilot (1)
    pivot (1)
    podcast (9)
    poetry (1)
    Political Campaign (1)
    pottery (1)
    power nap (1)
    Princeton (1)
    pro-wrestling (1)
    professor (1)
    Professor (1)
    psychotherapist (1)
    publishing (2)
    quotes (1)
    Ramini Mozzarella (1)
    rancho la puerta (1)
    ranch owner (1)
    real estate (1)
    rebellious (1)
    recap (1)
    recession (1)
    redemption (1)
    resolutions (1)
    restaurateur (1)
    retailer (1)
    retiree (1)
    retirement (11)
    retirement association (1)
    retirement plan (1)
    rhinos (1)
    Richard Eisenberg (1)
    richard turner (1)
    Richard Turner (1)
    Risk Taker (1)
    risktaker (1)
    robin pajaro (1)
    sacramento (2)
    Sacramento (2)
    sacramento (1)
    san francisco (1)
    san francisco giants (1)
    scott miller (1)
    second act (8)
    second acts (1)
    serial entrepreneur (1)
    Silicon Valley (1)
    small business (1)
    Small Business (1)
    smart living (1)
    socal (1)
    soul (1)
    sports (2)
    stand-up (1)
    Stanford (1)
    star of the week (4)
    steven petrow (1)
    success (1)
    superfan (4)
    susan stewart (1)
    task list (1)
    texas (1)
    the tapas life (1)
    third-act (1)
    third act (1)
    time management (1)
    time tracking app (1)
    Tim Jordan (1)
    toastmasters (1)
    top 10 list (1)
    transformation (1)
    travel (1)
    try new things (1)
    UC Berkeley (1)
    unretired (1)
    unretirement (41)
    Unretirement (1)
    unretirement (40)
    update (1)
    vacation (1)
    val haller (1)
    vice president (1)
    volunteer (2)
    walk on (1)
    water buffalo (1)
    website (1)
    wedding officiant (1)
    WNBA (1)
    work (2)
    working (1)
    world series (1)
    worst jobs (1)
    writer (1)
    writing (1)
    yoga (1)
    zen (1)