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The Best One Yet
👕 “American Crew” — Interview with Mickey Drexler, ex-CEO of The Gap & J.Crew
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We sit down with Mickey Drexler — the retail legend who built the modern American wardrobe. Over an 18-year run he grew Gap from $400 million to $14 billion in sales, founded Old Navy and turned it into the fastest brand ever to hit $1 billion, personally bought the Madewell name for $125,000, and later ran J.Crew. Steve Jobs put him on Apple's board, where he helped design the Apple Store — and then called him the night before Gap fired him with one day's notice. Today he's chairman of Alex Mill, the brand founded by his son.
Mickey opens up about his cameo on Breaking Bad, why Jackie Kennedy was his muse at Ann Taylor, the Paris moment that gave Old Navy its name, why Gap Kids was a mistake, the loudspeaker he installed at J.Crew headquarters, and why he thinks AI will never replace human taste. He also explains the one thing he says he'll never stop doing — and the rule he lives by that made khakis cooler than jeans. Plus: his pick for the best fashion brand he never worked for, and the advice he'd give anyone going into business with family.
CHAPTERS:
0:00 - Intro: Mickey Drexler on Building Gap, Old Navy & J.Crew
1:38 - Mickey Drexler's Breaking Bad Cameo, Explained
4:47 - Mickey Drexler, Ralph Lauren & Calvin Klein: The Bronx Fashion Story
11:51 - Mickey Drexler at Ann Taylor & His Jackie Kennedy Muse
14:09 - How Mickey Drexler Turned Gap From $400M Into $14B
23:33 - Why Mickey Drexler Says Gap Kids Was a Mistake
25:41 - How Old Navy Got Its Name & Took On Target
37:45 - How Mickey Drexler Bought Madewell's Name for $125,000
41:29 - Mickey Drexler & Steve Jobs: Designing the Apple Store
48:05 - How Steve Jobs Warned Mickey Drexler He'd Be Fired From Gap
49:27 - Mickey Drexler on Running J.Crew & Being a Micromanager
54:45 - Old Navy's American Flag T-Shirt & the Business of American Style
58:42 - Mickey Drexler on Why Fashion, Food & Fitness Live on Fads
1:04:08 - Mickey Drexler: Why AI Can't Replace Human Taste
1:06:19 - Mickey Drexler on Alex Mill & Working With His Son
1:07:29 - Rapid Fire: TJ Maxx, Best Business Book & Timeless Style
1:10:52 - Mickey Drexler's Takeaway on American Fashion
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🚀 “Big Iron Energy” — Interview with Baiju Bhatt of Cowboy Space
26:22|LIVE from Seattle we sat down with Baiju Bhatt, who co-founded Robinhood, and now runs Cowboy Space, a startup building its own rockets with plans to send 20,000 data centers into orbit. We talk about why data centers in space could match the cost of ones built in Texas, how the upper stage of a rocket turns into a data center with solar panels bigger than a football field, and what a satellite named Reason 1 is doing with lasers to send power back to Earth.Baiju also opens up about the book a high school chemistry teacher gave him, why Cowboy Space won’t hitch a ride on anyone else’s rocket, the $2 trillion Empire it is up against, why the first Big Iron launch is targeted for the end of 2028, and what happens when a rocket inevitably blows up. Plus the story of the four fingers he held up at Robinhood, why every part of Cowboy Space is named after a country song, and his rapid-fire picks for best brand, best business leader, and personal stock ticker. And what does he think the world looks like in 20 years if it all works?Chapters0:00 - Intro: Baiju Bhatt, Robinhood Co-Founder and Cowboy Space CEO2:18 - Baiju Bhatt’s Four Fingers: Robinhood’s Plan to Knock Out a Big Four Bank3:22 - Why Robinhood’s Co-Founder Started a Space Company: The Case for Mars6:03 - Cowboy Space Explained: Data Centers in Space and Big Iron Express6:56 - Why Data Centers in Space? Cowboy Space’s Cost Pitch vs. Texas8:13 - Big Iron Rocket: 15,000kg Data Center With Football-Field Solar Panels10:16 - Reason 1: Cowboy Space’s Satellite for Laser Power Beaming to Earth12:37 - Why Cowboy Space Builds Its Own Rockets for 20,000 Satellites13:55 - Cowboy Space vs. the Empire: Taking On a $2 Trillion Rocket Company16:24 - Why Cowboy Space Has a Cowboy Brand and Country Song Rocket Names17:59 - Elon Musk Says It’s a Good Time to Build Data Centers in Space19:46 - What Happens When a Cowboy Space Rocket Explodes?21:44 - Why Cowboy Space Chose Seattle: Kent Rocket Factory and Hiring23:22 - Space Infrastructure in 20 Years: Where Cowboy Space Goes From Here24:05 - Rapid Fire: Baiju Bhatt’s Favorite Brand, Business Leader, and Stock Ticker🌲 “LIVE from Seattle” — The AC/DC Election. Supersonics’ NBA biz. Magic The Gathering’s $2B card. +Salmon Toss MBA
23:50|2026 was the ACDC Election… Americans Complaining of Data Centers.”The Seattle Supersonics stopped playing 18 years ago… but the brand has never been bigger.How is Hasbro’s toy stock at All-Time-Highs? It’s Magic… As in Magic The Gathering.Plus, the secret to Seattle’s Costco, Starbucks, & Microsoft success?... Tossing salmon at Pike Place.Live from The Showbox Theater in Seattle, today’s LIVE SHOW is The Best One Yet…$HAS $SBUX $MSFT $COSTWant to see the LIVE show in action? Watch it on YouTube or check out the highlights on Instagram @tboypod.And tomorrow we’re publishing our full LIVE interview with our surprise guest: The Co-Founder of Robinhood & Cowboy Space, Baiju Bhatt.NEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.🗽“Biberty or Death”— In-N-Out’s burger brokers. Apple’s eating Big Tech. Liberty Biberty’s worst mascot. +Potty Parity
22:01|Grab your Tickets to our Final Live Show of 2026… Tonight in Seattle:Seattle 11/4: https://www.axs.com/events/1446394/the-best-one-yet-ticketsBurger Brokers are charging $225 to deliver In-N-Out… Sometimes unfriendly policy is nice.Apple’s doing 3x better than the rest of Big Tech… because of 1 thing it *didn’t* do.The 1 business story uniting America?... Hatred of Liberty Biberty’s mascot.Plus, the biggest economic problem in sports?... Women’s bathrooms (it’s Potty Parity)$AAPL $MCD $QQQNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.🍋 “Poison Soda” — Sprite’s SNL trolling. Fox’s stock market election. Anthropic’s surprise earnings. +Vote stickers
22:48|The big winner of the Midterms is ads… They’re ruining football and saving Fox’s cable biz.An SNL skit joked that Sprite is poison… but it should actually launch Sprite Cherry Lime Habanero.Anthropic amended its S-1 with Q3 earnings… and its biggest challenge is the Buffalo Bills.Plus, the most unifying force this election day… is the “I Voted Sticker” (we got the true story)$ANT $KO $FOXGrab your Tickets to the IPO Tour: Our In-Person OfferingSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.🎭 “Pay Per Aria” — Opera’s Gen-Z hack. TikTok’s restaurant app. Google’s internet crash. +Harvard’s fave class
21:55|Grab your Tickets to the IPO Tour: Our In-Person OfferingSeattle 11/4 https://www.axs.com/events/1446394/the-best-one-yet-ticketsGen Z loves the Opera, but can’t afford it… so Philadelphia’s letting people pick their price.Google crashed the internet, so Reddit blocked the internet… and Wall Street ain’t happy.TikTok launched a restaurant app, Whatnot launched live auctions… reminds us of Def Jam Records.Plus, the hottest class at Harvard bans phones, laptops, and AI… The anti-tech course has the longest waitlist.$RDDT $YELP $GOOGNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.🥸 “Whiskey Business” — Nvidia’s Chinese spy. Hershey’s flavor change. NYC’s $150M Marathon. +Pop-Biz Halloween Contest
24:25|Our Seattle live show on Wed 11/4 is now open to all ages! Buy tickets here: https://www.axs.com/events/1446394/the-best-one-yet-ticketsNvidia’s Jensen Huang has been targeted by a Chinese spy, according to NYT reports… It’s giving Cold War.You notice chocolate tastes different from your childhood?… Hershey knows why.The NYC Marathon turns 50 this weekend (56 actually)... It will make $150M revenue just like Birkin Bags.Plus, who will win our pop-biz Halloween contest?... Our money’s on “Allen Iverson AI.”$HSY $NVDA $QQQThe TBOY 10 is not investment advice and we do not attempt to examine all the facts and circumstances relevant to an investment decision. We are not recommending what you buy or sell. Our rankings don't reflect the views of Nasdaq or its affiliates. Always do your own research and talk to a financial advisor before making investment decisions.NEWSLETTER:https://tboypod.com/newsletterOUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD:Submit a shoutout or fact: https://tboypod.com/shoutoutsSOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypodLinkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.🍰 “Golden $CAKE” — Cheesecake Factory’s moment. WNBA’s 9am Final. Anthropic’s 1-person startup. +Halloween Purple
22:57|Cheesecake Factory is winning with complexity… Its super long menu defies restaurant econ.Anthropic acquired a 1-person biopharma startup… Can a solo-preneur cure cancer?WNBA Finals game 6 tips off at 9:30 this morning… But growth problems are good problems.Plus, why is purple the official color of Halloween?... The answer is psycho-nomics.$CAKE $ANT $SPYGrab your Tickets to the IPO Tour: Our In-Person OfferingSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.💁♀️ “AI For Moms” — Dazzle’s FemmeBot. DoorDash’s Instacart haul. Royal Caribbean’s Panama Canal. +Octo-bull
21:16|DoorDash is reportedly close to buying Instacart for $17B… because gig app winter is here.Marissa Mayer’s Dazzle launched an AI app for women… inspired by FUBU: For Us, By Us.Royal Caribbean is launching Panama Canal cruise ships… To chase the Silver Tsunami.Plus, October 28th is the stock market’s best day of the year… and we brought receipts.$CCL $CART $DASH $GOOGGrab your Tickets to the IPO Tour: Our In-Person OfferingSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.🐜 “ANTsy” — Anthropic’s IPO files. Candy Corn’s Copier. Chief of Staffs’ surge. +Bahston Ahccent
23:28|Anthropic is giving 1 supershare to its 7 co-founders… but the prices are in the tokens.Candy Corn is dominated by a company who copied it… in the fertile crescent of fructose.And Chief of Staff is the new life goal, every CEO has one… even though AI was supposed to erase them.And Nick tries out for Boston’s airport announcer guy…$SPY $SPXC $AMZNVoice of Boston contest: www.voiceoflogan.comGrab your Tickets to the IPO Tour: Our In-Person OfferingSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making today’s top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.