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Wingmen Show

Wingmen Show

Written 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.

© 2026 Wingmen Show
Politics & Government Self-Help Social Sciences Success
Episodes
  • Teach Them the Gouge--Pass On the Inside Information
    Nov 3 2026

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    You fought your way through the door. Now what? In Episode 268, Commander Drew Brown and Dr. Paul Thompson ask a question every person who has made it should answer: Are you holding the door open or telling the next person to fight just as hard? Drawing on their experience as Black naval aviators, the Wingmen make the case that passing on the gouge isn’t lowering the standard. It’s knowing where to put the work. Explain the process, make the introduction, give specific help, and then let the next generation take responsibility for their own flight. Pass down the wisdom, not the unnecessary hardship.

    The good news this week is all about people stepping up. Seven strangers in Prospect Park, Pennsylvania, lifted a car off a trapped e-bike rider with nothing but teamwork. New FBI figures show violent crime fell across the country last year, and the Wingmen talk about how to tell that story honestly without dismissing anyone’s pain. And high schooler Sarah Shelke built Mind4Youth, a youth-led organization helping young people get access to mental health support.

    In the Jet Jolt, the guys explain the emergency button that can actually land an airplane: Garmin Autoland. In the Frequent Flow-Line, Sophie, a bartender in Belgium, wants a bigger life but is afraid to leave what she knows. Ace takes the first answer, then Drew and Paul share what the Navy taught them about preparing for the next step. Ace also leads The Gouge on why learning and using people’s names matters. And the episode closes with a Wingmen story about a teenager who learns he isn’t half of anything. He’s twice blessed.

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    31 mins
  • When Nobody Answers: Follow Up—or Move On
    Oct 27 2026

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    You sent the application. You made the call. You wrote the proposal. And then—nothing. In Episode 267, Commander Drew and Dr. Paul take on one of the most frustrating spots in any career or life: the silent inbox. When do you keep knocking, and when do you take your energy somewhere it will be put to use? Drawing on their years as Black aviators in the Navy, the Wingmen make the case for keeping the mission while being willing to change the route—and for walking away with your dignity intact, not with a fiery farewell email.

    Then the theme plays out in real life. Commander Drew shares how a polite “no” from Sailor Services turned into a “yes” from the Virgin Voyages PR team, just ahead of his 21st and 22nd voyages. The Good News continues with a University of Pittsburgh study that paid students to sleep (and saw their grades rise), and Virginia’s expanded Clean Slate law opening doors for people whose old records keep following them. The Jet Jolt goes to sea with the Navy’s new drone that lands on a moving warship with no GPS and no pilot—by sight alone.

    An Oklahoma dad who gets a little too fired up in the bleachers gets advice on breathing, being present, and borrowing some calm from his wife. Ace takes on what separates a sharp AI prompt from a lazy one. And the Wingman Story travels to Recife, Brazil, where a futsal coach kept two photos of Matheus Cunha on a small altar at home—and watched the kid he coached at eleven score for Brazil at the World Cup.

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    33 mins
  • What the Hell Is Life All About?
    Oct 13 2026

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    Every now and then you have to stop chasing the next thing long enough to ask the big question: what is life really all about? In Episode 265, Commander Drew and Dr. Paul turn to Japan for some strong gouge—five time-tested philosophies that offer practical ways to live with more purpose, gratitude, and peace. From ikigai (your reason for getting up in the morning) to wabi-sabi (finding beauty in a few dents in the fuselage), the Wingmen make the case for living on purpose instead of on autopilot.

    The good news is a double feature. Nashville’s airport authority voted unanimously to begin renaming Nashville International Airport in honor of Dolly Parton—a tribute to a daughter of Tennessee who never forgot where she came from. Then a major study finds taxi and ambulance drivers had the lowest share of deaths attributed to Alzheimer’s among 443 occupations, and the guys talk about giving your brain new roads to travel.

    In the Jet Jolt, we go back to 1942 and the top-secret Bell XP-59A Airacomet—America's first jet, disguised with a fake propeller and a tarp, whose first flight topped out at just 25 feet. The Frequent Flow Line brings a heartfelt letter from a teenager in Philadelphia who wants to help her aunt find mental health support without making her feel judged. Ace joins the Gouge to break down the biggest red flags of a scam and what to do in the first 60 seconds. And the Wingman Story takes us to Cabo San Lucas, where a high school soccer star makes the most important assist of his senior year—off the field.

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    36 mins
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