Business Wars – Gap’s Revival | Better in Navy? | Episode 3

Original Airdate: November 13, 2025
Host: David Brown (A)
Guests: Jordan Holman, NYT retail reporter (C); Aubrey Avery Jr., former Gap Inc. executive (B)

Overview: The Return of an American Retail Classic

This episode examines the dramatic efforts to revive Gap, one of America’s iconic retail brands, after years of decline. Host David Brown, with guests Jordan Holman and Aubrey Avery Jr., traces Gap’s historical “cool,” its struggles against fast fashion, its viral new campaigns, and the enduring power of Old Navy, Gap Inc.’s sleeper success story. The discussion weaves between nostalgia and strategy as Gap’s new leadership tries to recapture relevancy with new tactics and a return to its roots in culture and community.

Key Discussion Points & Insights

I. What “The Gap” Means Across Generations

(00:01-05:15)

• Host opens: Gap evokes navy blue bags, 90s cool, Sharon Stone's iconic sweater, scent memories (00:01).
• Once a teenage essential, by the mid-2000s teens preferred fast fashion; Gen Z now associates Gap with viral celebrity TikTok ads (00:01-01:15).
• Richard Dixon (former Mattel exec and Barbie brand savior) joined as CEO in 2023, tasked with turning Gap around (01:41).
• Jordan Holman’s perspective: Grew up shopping Old Navy for value/flip flops, not Gap itself (04:57).

  "I did go to the Gap, but you would probably see me more often in Old Navy...remember, their $1 flip flops and, you know, American T shirts." (C, 04:57)

II. What Made Gap Special—and Why It Struggled

(05:16-10:54)

• The “Basics” Trap: Gap long known for casual jeans, tees, khakis—but these are widely available elsewhere too (05:41-06:08).

  "What Gap did was they hit on culture, they hit on music and photography...it was cool and ever present and it was at every mall." (C, 06:27)

• Peak Era: 1990s/early 2000s—Gap was a “stop you had to hit” in the mall, revenue ~$15B (07:22-07:57).
• Cultural Influence: Campaigns like “Individuals of Style” with celebrities made Gap the heartbeat of mall and pop culture (08:44).
• The decline: Mickey Drexler’s 2002 departure, rise of fast fashion (H&M, Uniqlo, Zara) with speed, trend responsiveness, digital savvy (09:19-10:54).

  "It's like, hey, we're switching it up. And maybe for too long, companies like Gap saw those companies on a different track compared to stealing their same consumers." (C, 10:31)

III. Attempts at Reviving Relevance: The Kanye West Partnership

(11:10-13:20)

• 2020: Gap’s surprise partnership with Kanye West seemed genius (stock jumped 40%), but "quickly fell apart" due to Kanye’s controversies (11:16-12:09).

  "It came out of left field. It was like, whoa, you guys are making big swings...what we've been doing for the past decade has not been working. How about we try to switch it up in a big way?" (C, 12:45)

IV. The “Barbie Guy,” Richard Dixon, and Gap’s Rebrand

(13:20-15:38)

• Richard Dixon’s arrival (2023): Brings brand revival expertise from Mattel’s Barbie (13:20).
• Jordan Holman: Dixon is reviving Gap as a cultural brand, leveraging social media/TikTok, star power, hiring designer Zac Posen, and emphasizing red carpet moments (14:28-15:10).

  "There's this back in a conversation, which I think it sounds simple, but it’s a big thing to even have a newer generation talk about Gap in the today compared to back in the day." (C, 14:48)

• Viral ads (Tyla for linen collection; Kelis’ “Milkshake” for denim) resonate across generations by mixing nostalgia and pop relevance (15:22-16:36).

  "I even went back to look at that ad on TikTok, and one of the comments was like, idk what you're selling me, but I'm sold." (C, 15:25)

V. Can Gap’s Mojo Return?

(17:19-19:15)

• Consecutive quarters of growth under Dixon, a milestone after years of up-and-down performance (17:39).

  "What Richard Dixon has done since his time is had consecutive quarters of growth...and so for that reason and with the good commercials, I'm going to say I think they have their mojo back." (C, 17:39)

• Viral ads open the door, but ultimately quality/merchandising must follow (18:28).

  "Ads are great, but what's the clothes looking like?" (C, 18:28)

Deep Dive: The Old Navy Story with Aubrey Avery Jr.

I. Old Navy’s Explosive Rise

(21:59-28:52)

• Old Navy launched in 1994 as a budget alternative to Gap, quickly reaching $1B in four years—first retailer ever to do so (21:59).
• Aubrey Avery Jr.: Hired as regional manager after a 15-person interview process, he joined with “some doubt” about the speed and scale, but strong leadership and team drive made it happen (25:56-27:59).

  "Going from three stores to 59 stores in the matter of a few years and generating a billion dollars...you just kind of grow, and we were hungry." (B, 27:59)

II. Old Navy’s Place in the Gap Family

(28:52-30:46)

• Old Navy’s ethos: Family, fun, and price; initially seen as “stepchild” within Gap Inc. but proved itself through performance (29:14-30:46).

  "We didn't have all the flair and the bells and whistles yet, but what we did have was drive and tenacity...our excessive and extensive growth really speaks for the industry." (B, 30:12)

III. Inside the Golden Era: Mickey Drexler’s Leadership

(32:33-36:56)

• Drexler was “the prince of Wall Street,” retail prodigy, famous for engaging directly with sales staff and seeking real opinions (32:33-33:41).

  “He would always position himself to know what the internal team within our companies, what they thought.” (B, 33:33)

• Drexler’s visionary approach led to innovative real estate moves, such as expanding into underserved communities (35:38-36:56).

IV. Entering Urban Markets: Community Engagement & Controversy

(36:56-39:11)

• Gap faced backlash after marketing in Harlem without Black representation in ads; forged community connections through local leaders (notably Magic Johnson and Rev. Calvin Butts) to resolve and build trust (37:06-38:31).

  “So we did that. And Reverend Butts...introduced us to his niece...and we got the situations resolved, and it gave us a foothold by understanding the community.” (B, 38:31)

V. Decline, Reflection, and Reinvention

(39:11-41:55)

• Post-2002, Gap lost its merchandising edge, suffered slumping sales, and store closures; required “reinventing” after riding high so long (40:32-41:17).

  "It's hard to go when you've been on top of the world until you slip and then you got to figure out, how do we regrow, redevelop our company going forward? It was a very sad time." (B, 40:32)

• Old Navy proved its enduring value, anchoring the corporation through tough times (41:25-41:55).

VI. Comparing Leaders: Drexler & Dixon (The Relay Race Analogy)

(42:06-43:24)

• Aubrey sees parallels between Mickey Drexler and Richard Dixon: both brand visionaries, customer-focused, and likely to “take it to a whole new level” (42:18).

  "...If you run a relay, it depends on how the baton is passed to person two, three and four. And I think Mickey did an incredible job of building the foundation of a phenomenal company. I think Richard is going to take that foundation...to a whole other level." (B, 42:18)

Notable Quotes & Memorable Moments

• “The magic of Gap back in the day: it wasn’t just the clothes; it was the conversation, the commercials, the music.” — Jordan Holman (C, 06:27)
• “What Richard Dixon has done… consecutive quarters of growth…with the good commercials, I think they have their mojo back.” — Jordan Holman (C, 17:39)
• “Old Navy had the whole family under one umbrella...when you look back...they’re doing 54, 56% of the whole corporation’s business.” — Aubrey Avery Jr. (B, 41:25)
• “Mickey [Drexler] was creative, innovative, and exceptionally intuitive…he would always want to know what the customer thought.” — Aubrey Avery Jr. (B, 32:33)
• “I think Richard [Dixon] is going to take that foundation…to a whole nother level. I think it’s about digital, it’s about music, it’s about AI, it’s about understanding who your customer is now.” — Aubrey Avery Jr. (B, 42:18)

Timestamps for Key Segments

• 00:01-01:41 – Setting the stage: Gap through the decades
• 04:49-19:15 – Jordan Holman on Gap’s cultural impact and contemporary comeback
• 21:59-30:46 – Aubrey Avery Jr. on Old Navy’s explosive growth
• 32:33-36:56 – Working with Mickey Drexler and Gap’s golden era
• 37:06-39:11 – Urban markets & the Harlem billboard incident
• 40:32-41:55 – Decline and Old Navy’s stabilizing role
• 42:18-43:24 – Drexler/Dixon: A relay race in brand stewardship

Overall Tone & Takeaways

The episode mixes business analysis, behind-the-scenes stories, and cultural nostalgia. There’s optimism about Gap Inc’s future thanks to Dixon’s renewed focus on cultural relevance, viral campaigns, and product direction. Old Navy’s legacy as an industry disruptor and community connector is celebrated. The guests’ candid reflections, especially on leadership and learning from failures, add human depth to the story.

[For anyone who missed the episode, this summary captures the rich interplay between retail history, branding, and leadership—and why the next chapter of Gap Inc. is one worth watching.]