Freakonomics Radio – "Dying Is Easy. Retail Is Hard. (Update)"

Date: November 28, 2025
Host: Stephen J. Dubner
Guests:

• Tony Spring (CEO, Macy’s Inc.)
• Mark Cohen (Former CEO, Sears Canada; Former Director of Retail Studies, Columbia Business School)
• Jeff Kinney (Author, “Diary of a Wimpy Kid,” Owner of An Unlikely Story Bookstore)

Episode Overview

This updated episode explores the economic and cultural significance of the Macy’s Thanksgiving Day Parade—and the precarious future of its parent company, Macy’s, amid the challenges facing brick-and-mortar retail. Through interviews with Macy's new CEO Tony Spring, retail expert Mark Cohen, and bestselling author-turned-community-retail-advocate Jeff Kinney, Stephen Dubner digs into why traditional retailers struggle, what could turn them around, and how places become destinations worth visiting—even as the economic landscape shifts. The episode balances a deep-dive into major corporate strategy with on-the-ground stories of retail revitalization and nostalgia.

Key Discussion Points & Insights

1. The Parade: Cultural Icon and Corporate Asset

• Tradition and Spectacle
  • The Macy’s Parade is watched by ~30 million TV viewers every Thanksgiving (00:45).
  • For many, it’s as essential to the holiday as turkey. Parade’s core appeal: “Tradition is at the core.” (Will Koss, Parade Exec. Producer, 02:05).
• Parade Isn’t Just Sentiment—It’s Business
  • Macy’s calls the parade its “gift to the nation”—but it’s likely a highly profitable marketing and sponsorship vehicle (03:30).
  • The parade may be one of the company’s most valuable assets as other parts of the business struggle.

2. Macy’s Today: A Company at a Crossroads

• Financial Vulnerabilities
  • Macy’s market cap is ~$6 billion, dwarfed by Target (~$40 billion) and Walmart (~$850 billion).
  • Macy’s real estate may be worth more than the company itself (04:20).
• Leadership’s Perspective: Tony Spring’s “Bold New Chapter”
  • Spring, former Bloomingdale’s CEO, became Macy’s CEO in early 2024.
  • “We are not just a retailer. We are not just a physical store. We are a celebrator of life’s moments.” (Tony Spring, 04:49)
  • Spring’s ambitions:
    • Close/sell 150 underperforming stores, opening smaller Macy’s.
    • Invest in store experience and merchandise curation.
    • Expand Bloomingdale’s and Bluemercury branches.
    • Rework private-label brands, lean into new trends (e.g., fragrances for boys) (29:32, 29:48).
    • Improve vendor relationships and bring back big brands like Nike (33:13).
• The Real Estate Dilemma
  • Market cap is half of real estate value: “Now is the time to buy Macy’s.” (Tony Spring, 11:08)
  • Monetization of real estate ongoing—$2.5 billion raised in past seven years (11:52).

3. The Skeptic: Mark Cohen on Retail’s Grim Realities

• Retail’s Place in the Economy
  • “Retailing is 70-80% of the world’s economy... some of the world’s biggest fortunes come from retail.” (Mark Cohen, 15:04)
• Why Department Stores Struggle
  • History: Downtown department stores → suburban malls → rise and fall of Sears and the vulnerability of Macy’s (16:06–18:26).
  • Complacency breeds failure: “Success in many cases brings complacency, hubris... they become convinced they are the last word.” (19:20)
• Macy’s Downward Drift
  • Once “as good as it gets,” Macy’s now “doesn’t stand for anything” (21:28).
  • Abused vendor relationships, overextension, slow to pivot to new retail trends (22:50).
• Skepticism of Turnaround Slogans
  • Prior Macy’s strategies were “more bull than real.” (38:30)
  • “Until it’s successful, keep your mouth shut because you create expectations that may not be realistic.” (Mark Cohen, 39:34)

4. What Makes Good Retail?

• Store Experience Matters
  • Good stores: clean, neat, friendly, well-assorted (40:35).
  • These basics are “enormously difficult to do. It takes years and years...” (Mark Cohen, 40:53)
  • Bad stores: remnants in dead malls, outdated buildings, weak brands, poor maintenance (30:51).
• Integration & Imagination
  • Can Macy’s instill the “magic” of the parade into its everyday retail experience? (35:15)
  • “Challenge given, challenge taken... But we also can’t hold the mirror on the parade to the store experience...” (Tony Spring, 35:45)

5. Retail Reinvention from the Ground Up: Jeff Kinney’s Bookstore

• An Unlikely Story in Plainville, MA
  • Bestselling author Jeff Kinney renovated his town’s abandoned market into an independent bookstore (45:01–46:08).
  • The bookstore is unprofitable but vital to community connectedness and town revitalization (48:14–48:31).
  • Plans to redevelop four city blocks into a new downtown hub: bookstore, restaurants, beer garden, Airbnb (49:05–54:26).
  • Motivation: transform a struggling town, “plant trees... they’ll never enjoy the shade of.” (54:39)
• Community Over Profit
  • Locals view Kinney as a hometown hero for rejuvenating Plainville (56:15–57:23).
  • Bookstore as a response to post-pandemic craving for real-life experiences and community (58:22).

6. Parallel Struggles, Shared Hopes

• Big and Small Retail’s Common Challenge
  • Whether Macy’s or a Plainville bookstore, the core question is: Can you make a destination people are dying to visit?
  • Is investment in physical space and community enough to change the fate of struggling retail (59:47–60:57)?
• Closing Reflections
  • Both Macy’s and Plainville are at pivotal points, trying not to simply replicate the past but build something lasting and meaningful (62:26).
  • “Retail is that mix of variety that creates the reason for the stroll and the reason to spend locally.” (Tony Spring, 61:51)

Notable Quotes & Memorable Moments

On Macy’s as more than retail:

“We are not just a retailer. We are not just a physical store. We are a celebrator of life’s moments.”
— Tony Spring, 04:49

On losing retail’s ‘magic’:

“The parade generates magic, but that’s not always the experience of shopping at Macy’s... you can’t put any magic into your shop floor.”
— Stephen Dubner citing an analyst, 35:15

On the codex of retailing:

“You have to fill the store with merchandise customers really want to buy... that is the codex of retailing. That is enormously difficult to do. It takes years and years and years...”
— Mark Cohen, 40:53

On investing for the long term:

“Society doesn’t become great until old men plant trees that they’ll never enjoy the shade of.”
— Jeff Kinney, 54:39

On skepticism of turnaround hype:

“Until it’s successful, keep your mouth shut because you create expectations that may not be realistic.”
— Mark Cohen, 39:34

On the parade’s brand value:

“Nothing gets presented during the parade that doesn’t have a price tag attached. But of course it doesn’t translate these days into footsteps doing business inside the store.”
— Mark Cohen, 25:20

On retail and community:

“I miss the candy store, I miss the bookstore, I miss the record store. Retail is that mix of variety that creates the reason for the stroll and the reason to spend locally.”
— Tony Spring, 61:51

Timestamps for Significant Segments

• Parade’s cultural & financial importance: 00:45–03:30
• Macy's real estate and market cap context: 04:20–05:37
• Tony Spring on turnaround and vision: 06:00–13:32, 29:13–36:08
• Mark Cohen on retail history and Macy’s difficulties: 15:04–24:37
• Cohen critiques Macy’s management & vendor relations: 21:28–24:02
• Tony Spring on store closures, vendor relations & store of the future: 29:13–35:15
• Mark Cohen on retail basics (“clean, neat, and friendly”): 39:37–40:53
• Jeff Kinney on building a bookstore and rejuvenating a small town: 45:01–54:39
• Locals talk about bookstore’s impact: 56:15–57:23
• Reflections on Macy’s, retail future & community: 59:10–62:26
• Closing thoughts & parade as a shared American ritual: 63:05–64:26

Summary Takeaways

• The Macy’s Thanksgiving Day Parade remains an iconic anchor for a weakened company, providing a rare spark of magic and publicity.
• The core struggle for department stores is differentiation and relevance in an age of disintermediation, nimble e-commerce, and changing consumer habits.
• Macy’s bold new strategy centers on rightsizing physical stores, renovating the retail experience, rebuilding with better brand partnerships, and leveraging its enduring legacy assets.
• Retail expert Mark Cohen provides a sobering reality check, warning that slogans and incremental improvements rarely fix structural decline.
• In contrast, Jeff Kinney’s unprofitable but beloved bookstore shows the emotional power of investing in spaces and community—even when “the numbers” make no sense.
• Both Macy’s and the indie bookstore operate under the uneasy hope that tradition, innovation, and human connection can pull retail through radical, unpredictable change.

Tone

• Analytical, wry, sometimes nostalgic, with candid business reality checks and moments of heartfelt community optimism.
• The episode oscillates between big corporate strategy and local-hands-on-the-pulse storytelling, giving the listener both a bird’s-eye and street-level view of retail’s uncertain future.