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Wingmen Show

Wingmen Show

By: Drew Brown and Paul Thompson
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About this listen

Two Dope Boys in a Navy jet. The Wingmen Show is a weekly podcast about challenges and opportunities in everyday life. Your hosts are two guys born in Harlem, New York previously unknown to each other. Separately, they became Navy pilots flying high performance jet aircraft on and off of aircraft carriers patrolling the world’s oceans. Their paths did not cross formally until they ended up flying for the same airline after their active-duty military service had ended. They have a wide range of experiences spanning the worlds of basketball and boxing. Drew’s father is Drew Bundini Brown, Muhammad Ali’s Wingman and coined the iconic phrase “Float Like A Butterfly Sting, Like A Bee". Martial Arts and Show Business are also areas of mutual interest. Drew has been featured nationally on television programs such as the Donahue Show and the Today Show. He has also appeared in hundreds of newspapers and magazines. Both are published authors as well as former Navy jet pilots and Commercial Airline Pilots; they retired after having flown the Boeing 777 airliner. The cultural mix of religions, immigrant parents and grandparents from Europe and the Caribbean gives them an uncommon perspective on racial matters. Melding the cultures of New York City, Pittsburgh, New Orleans, Memphis, the Caribbean and Atlanta has helped shape their worldview when combined with the life they have seen and experienced having flown extensively to countries throughout the world.They are wingmen to each other, providing advice, guidance and constructive criticism when needed. The goal of the show is to inspire and entertain those unafraid to expand their minds and perhaps learn something new in the hope that the listeners can become wingmen to others. Each one, teach one.© 2023 Wingmen Show Personal Development Personal Success Politics & Government Social Sciences
Episodes
  • You Gotta Believe, Rewriting Your Story the Wingmen Way
    Apr 21 2026

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    In this episode, Commander Drew and Dr. Paul get personal—sharing the real story of how two kids from Harlem rewrote their flight plans, from nightclubs and oil rigs to Navy jets, FedEx 777s, and a purpose-driven podcast. Then the good news keeps coming: a 16-year-old Girl Scout building a scam-awareness game for seniors, the seven types of rest you're probably not getting, a pizza delivery man whose small act of kindness earned an 80,000% tip, California's first graduating class of incarcerated women earning real bachelor's degrees, and an anonymous donor who quietly dropped a million dollars to help nurses pay off their student loans.

    We talk about:

    • How Commander Drew went A to Z through every occupation until one word grabbed him by the collar: pilot
    • Why your story is not locked in by your neighborhood, your past mistakes, or your age
    • A 16-year-old who turned her grandparents' near-scam into a game that's protecting seniors everywhere
    • The 7 types of rest — and why sleeping more isn't the same as actually recovering
    • Dan the pizza delivery man, a missing Diet Coke, and $130,000 in tips
    • California's first cohort of incarcerated women to earn bachelor's degrees — and what the recidivism numbers actually say
    • The Jet Jolt: Electric air taxis that take off like helicopters and cruise like airplanes
    • A Brooklyn senior asks: Should I join the military — and if so, how do I choose the right branch?
    • Ace's Gouge: Staying strong and sharp after 50 — what actually moves the needle
    • A Wingman Story that will stay with you: "Forty Wingmen in Tokyo"


    Your Wingman Challenge This Week: Tonight, ask yourself the same question Commander Drew asked at 26 — "What am I gonna be when I grow up?" Then write one new chapter: one decision, one phone call, one class, one habit that moves you toward the life you really want.

    Small moves, flown consistently, change the whole flight plan. Thanks for flying with us. Your Wingmen, Commander Drew & Dr. Paul — The Wingman Show

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    40 mins
  • Welcome To The Dark Side of the Moon
    Apr 14 2026

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    FROM THE COCKPIT — EPISODE 245 SUMMARY: In this episode, Commander Drew and Dr. Paul take a front-row seat to one of humanity's boldest missions: Artemis II — the first crewed flight around the Moon in over 50 years. They break it down in plain English, from liftoff to splashdown, and connect it to the kind of courage it takes to fly into the unknown. Then the conversation comes back to Earth with two powerful pieces of good news: Sweden's decision to put books back in classrooms, and new global research on the surprising power of forgiveness.

    We talk about:

    • What Artemis II actually did — and why it matters for the future of space exploration
    • The "skip re-entry" maneuver that kept four astronauts from burning up on the way home
    • Why Sweden is ditching screens in classrooms — and what the research actually says
    • Forgiveness as an internal maintenance check — patching the cracks so your soul doesn't fail under stress
    • The Jet Jolt: Why some airliners land sideways on purpose — and nail it every time
    • Rosalita in Minneapolis asks: How do I build a news pre-flight checklist so I can think for myself?
    • Ace's Gouge: Three money moves in your 20s, 30s, and 40s nobody actually teaches you
    • A Wingman Story that will stay with you: "The Extra Chair”




    Your Wingman Challenge This Week: Ask yourself — who am I still carrying in my head and my heart? Choose one small act of forgiveness this week. Not for them. For you.

    Small moves, flown consistently, change the whole flight plan. Thanks for flying with us. Your Wingmen, Commander Drew & Dr. Paul — The Wingman Show

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    33 mins
  • What We Can Learn From the Happiest Countries and why are these Countries the Happiest?
    Apr 7 2026

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    In this episode, Commander Drew and Dr. Paul explore what the world's happiest countries are doing right — and what the U.S. can learn from Finland, Iceland, Denmark and a surprising newcomer, Costa Rica. The conversation moves into youth happiness, technology, and why the most connected generation is also one of the most isolated.

    We talk about:

    • Why "Pura Vida" is more than a slogan — it's a life philosophy
    • How social media has replaced connection without replacing loneliness
    • The flying umbrella drone that had us laughing on the flight deck
    • A Manchester listener stuck in a holding pattern — and how to break out of it
    • The power of saying no without burning bridges


    Plus the Jet Jolt — Racing the Sunrise at 35,000 Feet — and a Wingman Story that will stay with you.

    Your Wingman Challenge This Week: Pick one "runway move" — one habit, one project, one person to encourage — and commit to it this week.

    Small moves, flown consistently, change the whole flight plan.

    Thanks for flying with us.

    Your Wingmen, Commander Drew & Dr. Paul The Wingman Show


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    33 mins
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