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The Best One Yet
š āAmerican Crewā ā Interview with Mickey Drexler, ex-CEO of The Gap & J.Crew
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We sit down with Mickey Drexler ā 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 ā 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 ā 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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š„ āSultans of Saladā ā Sweetgreen Co-Founders Jonathan Neman & Nicolas Jammet
36:27|LIVE from sold-out Bostonā¦ we sat down with 2 of the 3 co-founders of Sweetgreen.In this sitdown, Jon & Nic explain how 2 years after college, they booked The Strokes for a salad music festival, eventually landing Kendrick Lamar (for salads!).Sure, Sweetgreen stock is down 80% from its post-IPO all-time highs, but theyāve bet a comeback on a $12 custom-wrap tortilla that took a full year to build. And theyāve figured out how to keep employees longer by hiring robots (the āInfinite Kitchenā).Jon & Nick reveal the ROI on the wraps, why the $20 salad rep is undeserved, and how the founders rank taste/health/sustainability as marketing tactics. Want to know the 1 trait they look for in a job interview? The CEO and CCO of Sweetgreen told usPlus, if you think āSlop Bowlsā is an offensive term (which we do), we actually rebranded it in real-time on-stage with both of them #BonusBowls #FreshCasual.But most of all, we just had fun catching up with 2 of the Caesars of Salads who turned kale from a Pizza Hut decoration into an economic force ā And from the audience cheers, you know the hummus-headed Yetis did too.CHAPTERS0:00 - Intro (Live from Boston): Sweetgreen Founders Jonathan Neman & Nicolas Jammet 2:04 - How Sweetgreenās Founders Met at Georgetown and Why They Opened a Salad Shop 4:42 - Sweetgreen Opened on the Wrong Side of the Street, Then Booked The Strokes for 20,000 Fans 8:52 - Sweetgreenās Best-Selling Menu Item: How the Company Ranks Its Bowls 10:14 - Sweetgreen Wraps: Gen Z Growth, $11 Price and the Custom Tortilla 15:09 - Sweetgreen Infinite Kitchen: How Its Salad-Making Machine Changed Employee Turnover 19:31 - Sweetgreen Stock Down 80% From All-Time High: CEO Responds 21:51 - Is Sweetgreen Too Expensive? The $20 Salad Debate, Prices and Protein Portions 24:08 - Sweetgreen Marketing: Taste vs. Health vs. Sustainability 26:45 - Sweetgreen Limited-Time Offers and Collabs: Dan Barberās Squash, Naomi Osaka, Kendrick Lamar 29:36 - Sweetgreen vs. Chipotle: 300 Stores vs. 4,000 and Why No Brand Tie-Ups 30:19 - What Sweetgreenās Founders Look For When Hiring 32:05 - Slop Bowl Debate: Sweetgreen Wants a Rebrand 33:35 - Rapid Fire: Best Brand, Business Book and Sweetgreenās Stock Ticker 34:42 - TakeawaysNEWSLETTER:https://tboypod.com/newsletterOUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD:Submit a shoutout or fact: https://tboypod.com/shoutoutsSOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypodLinkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.āļø āLIVE from Bostonā ā Ben Affleckās AI genius. Bananas inflation-omics. Uberās data center piggybacking. +Top-smelling cities
26:15|Bumble got acquired in a happier-ever-after Private Equity endingā¦ We call it D.O.P.E.Apple just unveiled a dozen surprise home productsā¦ Itās the new bossā Living Room strategy.AI stock investing has become āa casinoā... so weāll tell you how to play it.Plus, Mark Zuckerberg canāt finish a Guinessā¦ (is that a sip or a struggle?)$AAPL $BMBL $AVGO $METAGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.š” āiHomeā ā Appleās living room strategy. Bumbleās Kate Hudson moment. AIās casino stocks. +Zuckās Guiness
22:40|Bumble got acquired in a happier-ever-after Private Equity endingā¦ We call it D.O.P.E.Apple just unveiled a dozen surprise home productsā¦ Itās the new bossā Living Room strategy.AI stock investing has become āa casinoā... so weāll tell you how to play it.Plus, Mark Zuckerberg canāt finish a Guinessā¦ (is that a sip or a struggle?)$AAPL $BMBL $AVGO $METAGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 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 todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.š āDoll Bills, Yāallā ā American Girl Dollās 40th. Nobelās economic therapy. Dutch Brosā walk-thru. +Self-Driving Zambonis
23:51|The Nobel Prize for Economics went to Robert E. Hall and Michael Woodfordā¦ because clear is kind in Economics too.Dutch Bros opened their first walk-thru locationā¦ What's the LCD (Lowest Cost Differentiator)?American Girl Doll just turned 40 and is worth $1Bā¦ because the founder went anti-Barbie.Plus, Waymo is coming for hockey rinksā¦ The 1st self-driving Zamboni.$MAT $BROS $SPYGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.šÆāØļø āPumpkin Spice Tacoā ā Starbucksā Chipotle acquisition. SpaceXās cellular biz. Airbnb killed MidCenturyMod. +NFL Math Whiz
22:30|Starbucks wants to acquire Chipotleā¦ but it all comes down to beans.SpaceX could be your next cell service providerā¦ Elon has entered the telecom chat.Millennialsā Mid-Century Modern furniture has gone from cool to cringeā¦ But blame Airbnb.Plus, economicsā new math whizā¦ is a former Pro NFL Linebacker from the Baltimore Ravens.$CMG $SBUX $SPCX $ABNBGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.š« āSlug lifeā ā Vaselineās creator hack. Agentic shopping bubble. Official hotel cars. +LIVE from NY AdWeek
21:27|Weāre recording LIVE from NY AdWeek at SeedTagās headquartersā¦ We're in our MadMen Era. But we still got 3 fantastic stories for ya:Vaseline turned viral life hacks into new productsā¦ and treats the inventors like Youtube creators.AI assistant shopping is dividing Amazon vs. Shopifyā¦ but why outsource something you like to do?Hotels, complimentary cars, and speeding tickets on usā¦ itās not a free sample, itās a fun sample.$UL $MAR $METAGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 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 todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.š«µ āRe-Pokedā ā Facebookās movie sequel. Crocsā jibbitz bars. SpaceXās debt doozy. +Nasdaq x TBOY
24:00|SpaceX is lining up $40B in debt to buy Nvidia chipsā¦ This 1 deal explains our entire economy.Crocs stock is up thanks to Jibbitz bars, shoe tattoos, and āShoelleryā... (thatās shoe jewelry)The Social Reckoning premiers tonightā¦ but Mark Zuckerbergās not the villain, heās the Anti-Hero.Plus, we just signed an historic deal with Nasdaqā¦ And rang the stock market opening bell.$CROX $META $SPCXGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.š āTuna Tuesdayā ā Sushi Carving surge. Sam Altmanās AI movie. Red-Dye Dieselās drama. +Warren Buffett YouTube
22:36|Restaurants are loving 1,000-pound Tuna Carvingsā¦ cause Tuna Tuesday saves biz models.Diesel prices have officially doubled, but thereās 1 diesel you gotta knowā¦ Red-dye Diesel.The new Sam Altman movie is so controversial, Amazon dropped itā¦ weāll tell ya why.Plus, the biggest new YouTube stan?... Itās Warren Buffett (and he loves āUzbekistan Got Talentā).$AMZN $MSFT $GOOGGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsNEWSLETTER:https://tboypod.com/newsletter OUR 2ND SHOW:Want more business storytelling from us? Check our weekly deepdive show, The Best Idea Yet: The untold origin story of the products you're obsessed with. Listen for free to The Best Idea Yet: https://wondery.com/links/the-best-idea-yet/NEW LISTENERSFill out our 2 minute survey: https://qualtricsxm88y5r986q.qualtrics.com/jfe/form/SV_dp1FDYiJgt6lHy6GET ON THE POD: Submit a shoutout or fact: https://tboypod.com/shoutouts SOCIALS:Instagram: https://www.instagram.com/tboypod TikTok: https://www.tiktok.com/@tboypodYouTube: https://www.youtube.com/@tboypod Linkedin (Nick): https://www.linkedin.com/in/nicolas-martell/Linkedin (Jack): https://www.linkedin.com/in/jack-crivici-kramer/Anything else: https://tboypod.com/ About Us: The daily pop-biz news show making todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.š āScary Goodā ā Halloweenās Skelly economy. Detroitās minivan miss. Rampās money musical. +Celeb Beauty Bubble
23:00|12-foot skeleton decorations make Halloween corporate Americaās favorite holiday.Ramp, the FinTech company, made a Broadway musical inspired by Hamilton.Detroitās 3 big car companies had 2 huge misses in 2026: Millennial Minivans & Boomer Hybrids.Plus, the biggest bubble right now isnāt AIā¦ itās celebrity beauty & beverage brands.$HD $ELF $GMGrab your Tickets to the IPO Tour: Our In-Person OfferingBoston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 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 todayās top stories your business. Formerly known as Robinhood Snacks, The Best One Yet is hosted by Jack Crivici-Kramer & Nick Martell.