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Freakonomics Radio

Dying Is Easy. Retail Is Hard. (Update)

with Tony Spring, Mark Cohen, Jeff Kinney, Will Koss

Published November 28, 2025
View Show Notes

About This Episode

This episode examines the troubled state of Macy's and the broader retail industry through conversations with Macy's CEO Tony Spring, retail veteran and academic Mark Cohen, and author-entrepreneur Jeff Kinney. Spring lays out his Bold New Chapter turnaround plan, including major store closures, real estate monetization, merchandise overhauls, and attempts to translate the marketing power of the Macy's Thanksgiving Day Parade into better in-store experiences. Cohen sharply criticizes Macy's past strategies and questions the viability of the turnaround, while Kinney offers a contrasting example of place-based, community-focused retail through his unprofitable but culturally influential independent bookstore and downtown redevelopment project in Plainville, Massachusetts.

Topics Covered

Retail distribution Entrepreneurship Online retail Community building Urban design and culture Parade logistics and event management Business growth and scaling Customer service Marketing and customer education LaBelle Missouri town revitalization

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Macy's CEO Tony Spring is pursuing a Bold New Chapter strategy that involves closing roughly 150 underperforming large stores, investing in smaller formats, enhancing assortments, and leaning into higher-end brands via Bloomingdale's and Blue Mercury.
  • Despite Macy's valuable real estate and highly profitable Thanksgiving Day Parade, retail expert Mark Cohen argues that the chain has lost its identity, abused vendors, and faces an uncertain future amid disintermediation and intense competition.
  • The Macy's parade is likely a substantial profit generator and powerful branding vehicle, but it no longer reliably converts TV viewership into store traffic.
  • Jeff Kinney's An Unlikely Story bookstore in Plainville loses money but has become a major cultural hub and author destination, anchoring a much larger $17-35 million plan to revitalize the town center.
  • Both Macy's and Kinney's Plainville project illustrate attempts to rebuild physical spaces where people want to gather in an increasingly digital economy, but on vastly different scales and business logics.

Podcast Notes

Introduction: Macy's Thanksgiving Day Parade and the future of retail

Re-airing and updating a two-part series on the Macy's parade

Stephen Dubner explains this is the second and final part of a series first published in 2024, with updated facts and figures[1:00]
He thanks listeners and sets up the focus on the economics of the parade and Macy's broader situation[1:05]

Scale and emotional role of the Macy's Thanksgiving Day Parade

About 30 million people watch at least some of the parade on TV every Thanksgiving morning[1:15]
For many viewers, Thanksgiving would not feel complete without the parade[1:25]

Tradition as the parade's core appeal

Parade executive producer Will Koss previously told Dubner that the parade's popularity is rooted in tradition[1:29]
• Koss describes tradition as being at the core, with the parade showing up every Thanksgiving morning as a giant, dependable event
• He characterizes it as spectacle, kitsch, and art, and a moment people can always come back to

Macy's parade as a profitable 'gift' and strategic asset

Macy's calls the parade its annual gift to the nation, but Dubner notes the gift is likely quite profitable for Macy's[2:33]
He suggests the parade may be one of the most valuable remaining assets that Macy's has[2:52]
Dubner frames the risk that if Macy's disappears, the parade would probably disappear as well[3:16]

Macy's current economic position and industry context

Macy's market capitalization and real estate value

As of the recording, Macy's has a market cap around $6 billion, up from around $4 billion when the series was first published[3:28]
Target's market cap is around $40 billion and Walmart's around $850 billion, highlighting Macy's relatively small scale[3:34]
Macy's real estate alone is believed to be worth more than its $6 billion market cap[3:41]
• Dubner suggests this could indicate that Macy's is no longer good at being a department store or that department stores are broadly doomed

Importance of retail in the global economy

Dubner notes that while the show has often focused on thriving sectors like biotech, software, energy, and entertainment, retail is a huge share of the global economy[4:04]
He positions this conversation as overdue and worthwhile due to retail's economic significance[4:17]

Episode structure overview

Dubner says Macy's CEO Tony Spring will make his case for the company[4:27]
He notes there will also be a dissenting voice challenging Macy's strategy[4:37]
The episode will also spotlight a different retailer trying to swim against the tide of retail decline[4:46]

Tony Spring: background, career, and view of Macy's assets

Spring's rise to CEO and philosophy about the parade

Tony Spring became Macy's CEO in February 2024 and chairman of the board a couple of months later[5:27]
He says he wants the parade to be perceived as a gift to the city and the nation, but also wants to do a lot of business[5:41]
Spring quotes a former Bloomingdale's colleague: they want to win an Oscar and also win at the box office, implying both prestige and profit[5:48]

Personal background and early lessons in customer experience

Spring grew up in Westchester County, just north of New York City[5:53]
As a kid, Macy's Herald Square felt like an overwhelming adventure to him, with oversized ceilings, storytelling, and wooden escalators[6:02]
• He notes that the old wooden escalators are still functioning today
He fell in love with retail while working in hospitality, starting at a Burger King in high school[6:20]
• He initially loved interacting with customers and hearing the cash register ring
• During his first week, he was assigned only to clean the parking lot; the manager later explained that the parking lot is the first impression and influences perceptions of cleanliness and freshness
• Spring says that 'first impression' mentality stayed with him throughout his retail career

Education, Bloomingdale's experience, and Macy's corporate history

Spring studied at Cornell's hospitality school and met a recruiter from Bloomingdale's who placed Cornell graduates into an executive training program[6:58]
He joined Bloomingdale's in 1987 and describes it as known for 'of the moment' ideas and innovative merchandising[7:31]
• He recalls Bloomingdale's selling novelty products such as rocking flowers that moved to music, mood rings, pieces of the Berlin Wall, and early merchandise from India and China
Dubner outlines the corporate sequence: Bloomingdale's was part of Federated; Macy's attempted but failed to acquire Federated; Federated then went bankrupt; Macy's later went bankrupt; Federated emerged from bankruptcy and acquired Macy's[8:08]
Federated became the largest U.S. department store company, then rebranded as Macy's Inc. and converted many banners to Macy's, while keeping Bloomingdale's separate due to its strong brand[8:25]
In 2015, Macy's Inc. acquired the high-end beauty retailer Blue Mercury[8:33]
Today, Macy's Inc. consists mainly of Macy's, Bloomingdale's, and Blue Mercury[8:41]
Spring says these brands will remain separate for now, but the mix will change as Macy's shrinks[8:48]
• Macy's store count has fallen from over 800 in 2007 to fewer than 500, with further declines planned

Spring's mandate and customer base

Dubner characterizes Spring's job as needing to stop the bleeding at Macy's[9:07]
Spring notes that despite challenges, Macy's still has 41 million active customers across five generations[9:17]

Activist pressure, real estate value, and Macy's as a stock

Recent takeover proposal and board response

Earlier in the year, investment firm Ark House and asset manager Brigade made a takeover proposal to Macy's[9:24]
At that time, Macy's market cap was about $4.2 billion, and Ark House proposed around $6 billion[9:34]
Dubner cites estimates that Macy's real estate portfolio is worth $7-11 billion and asks Spring if this seems accurate; Spring declines to opine, saying he will leave that to real estate experts[9:55]
Spring emphasizes that Ark House's approach was a proposal, not a fully financed offer[10:05]
• After seven months of due diligence, Macy's board unanimously decided to move on and focus on creating value for shareholders
• Spring says they remain open to a higher valuation than the current price but prioritize improving the consumer experience

Perception of Macy's stock relative to real estate value

Dubner notes that Macy's market cap is roughly half the estimated real estate value and asks what that implies[10:46]
Spring responds that now is the time to buy Macy's, highlighting its low valuation multiple and turnaround commitment[10:59]
• He points out that as a portfolio company, shareholders get Macy's, Bloomingdale's, and Blue Mercury together
• He notes Macy's has monetized over $2.5 billion in real estate over the last seven years by selling properties
Spring says Macy's is a retail company first that happens to benefit from a strong real estate portfolio and will continue to both acquire and divest assets[11:45]

Store ownership versus leasing and planned closures

Dubner clarifies that the real estate value mainly refers to large Macy's and Bloomingdale's locations that the company owns[12:02]
Macy's rents most smaller stores and Blue Mercury locations[12:24]
Spring plans to close and sell around 150 of the larger Macy's stores, which Dubner says should raise roughly half a billion dollars[12:19]
At the same time, the company plans to open some smaller Macy's stores and expand Bloomingdale's and Blue Mercury[12:24]
Spring describes the company as ambitious and hungry, but acknowledges a 'relevancy gap' that his team needs to address[12:40]

Parade as brand asset and broader positioning of Macy's

Dubner notes that Macy's executives are reluctant to discuss the parade economics, though it is plainly expensive and obviously valuable based on sponsorship and ad revenue[12:54]
He directly asks if the parade might be Macy's most valuable asset; Spring calls it valuable but not the most valuable, likening it to the Herald Square flagship as a key asset[13:19]
Spring positions Macy's not just as a retailer or physical store, but as a 'celebrator of life's moments'[13:29]
• He contrasts ordinary needs like buying socks or jeans with extraordinary moments such as the parade, fireworks, 50th birthday parties, weddings, and the birth of a child where Macy's can play a role

Mark Cohen on retail, Sears, and Macy's decline

Cohen's background and importance of retail studies

Mark Cohen recently retired as professor and director of retail studies at Columbia Business School after a 30-year retail career[14:16]
His first job was at Abraham and Strauss, and his last was as CEO of Sears Canada, both chains that no longer exist[14:29]
Cohen says retailing is arguably the largest industry, representing 70-80 percent of the world's economy[14:50]
He notes a resurgence of interest in retailing, especially on the entrepreneurial side[14:54]
• He points out that major fortunes have been made in retail, citing the Walton family, Jeff Bezos/Amazon, Zara/Inditex, and LVMH

Sears as a case study of rise and fall

Cohen emphasizes that the retail customer has never disappeared; customers are 'hard-coded' to want to shop, limited mainly by economic capacity and proximity to marketplaces[15:54]
Around the turn of the 20th century, U.S. customers shopped downtown department stores and via catalogs like Sears Roebuck[16:23]
• He notes that Sears catalogs sold everything from apparel to a 'you-build-it' house
After World War II, returning servicemen migrated from cities and rural areas to newly formed suburbs[17:01]
Cohen credits President Dwight Eisenhower with enabling mid-20th century retail through the interstate highway system, modeled partly on the German autobahn[17:14]
• Eisenhower's original rationale was efficient movement of men and material for national defense, replacing two-lane blacktop roads
• Cohen argues the highway system ultimately spurred massive suburban migration, around which malls were built
Suburban mall retail hollowed out downtown retail in hundreds of U.S. cities, and Sears migrated to those malls, becoming the world's largest retailer through the 1960s[18:12]
Cohen attributes Sears's eventual decline to complacency and hubris from success, becoming insular and convinced of their own invincibility[18:23]
He recounts that when Home Depot's founders sought financial support from Sears, Sears executives laughed them out of the meeting, seeing them as upstarts[18:54]

Macy's at its peak versus Macy's today

Cohen describes Macy's heyday as a brilliantly constructed general merchandise emporium serving customers from low-middle income to near luxury[19:06]
He says the stores were very attractive, powerfully merchandised, topical, current, and consistently executed[19:23]
He highlights Macy's creation of 'the cellar' at Herald Square, transforming the lower level into a large, vibrant housewares business[19:45]
• Previously utilitarian categories like frying pans were reconceived as parts of full suites of cookware presented in an exciting way
Cohen calls this an example of putting puzzle pieces together in a new way, making underappreciated categories fashionable and profitable[20:21]
He identifies the 1960s and 1970s as Macy's strongest decades and says it was very profitable and regarded as 'as good as it gets'[20:26]
Macy's was known for fashionable clothing, top brands, and substantial private label portfolios in apparel, accessories, and home[20:53]
Asked what Macy's stands for today, Cohen answers that in his view Macy's does not stand for anything[21:08]
• He argues a consumer-facing brand must stand for something recognizable to customers, differentiated from competitors, and defensible against competition

Strategic missteps: acquisitions, consolidation, and vendor relations

Cohen says Macy's began to prop up lagging productivity by buying competitors and playing a 'last man standing' game, believing acquisitions were the secret to life because they reduced direct competition[21:36]
Macy's consolidated regional banners under the Macy's name to retain relevance amid pressure from specialty chains, big-box off-mall retailers, and Amazon[21:53]
He criticizes Macy's for historically abusing its vendor community, a charge he says former CEOs dispute only weakly[22:30]
• He details Macy's demands: best price up front, advertising and presentation allowances, gross margin guarantees, markdown protection, and exclusivity agreements that limited brands from selling elsewhere
• Many brands reluctantly complied because Macy's was 'the only game in town' for their merchandise at the time, but Cohen notes they now have alternatives

Cohen's prognosis for Macy's and view of the parade's value

Asked whether Macy's will still exist in 10 years, Cohen calls it 'problematic'[23:43]
He notes multiple failed attempts by activists to monetize Macy's assets, principally real estate, and claims 'there is no there there' despite valuable flagships like Herald Square and Union Square[23:53]
Cohen doubts that any buyer would pay billions of dollars to put an office tower atop Herald Square[24:09]
Dubner observes that Macy's market cap is just over $4 billion while real estate estimates are roughly double, and he points to the parade as a major profit center through sponsorships and ad revenue[24:22]
He asks Cohen if the parade could be the single most valuable asset Macy's still has; Cohen says Dubner is not crazy but stresses that value requires both a holder and someone who wants to possess it[24:52]
• Cohen uses the Super Bowl as analogy: the Super Bowl ad market only exists because the game itself exists
• He notes the parade has always been attached to Macy's and has become a commercial enterprise in its own right
• He says Macy's will never voluntarily reveal parade costs and revenues unless required by law, but it is likely a substantial profit generator where nothing appears without a price tag
• However, he adds that the parade does not currently translate into store footsteps and business as it once may have

Tony Spring's Bold New Chapter strategy and operational challenges

Components of the Bold New Chapter plan

Dubner explains that Spring, after leading Bloomingdale's for nine years, has been tasked with engineering a turnaround at Macy's[27:52]
Spring labels his turnaround blueprint 'a bold new chapter'[28:13]
He says the strategy includes strengthening the Macy's brand and divesting about 150 stores that are no longer relevant[28:22]
It involves investing in improved merchandise assortments and completely revamping the private brand portfolio by exiting irrelevant brands and introducing new ones[28:41]
• Spring gives an example of a current trend: boys wearing perfume or cologne influenced by social media like TikTok, and says Macy's must lean into that with a strong assortment to be seen as a fragrance destination
He also prioritizes improving store conditions, increasing staffing, enhancing visual presentation, and experimenting with different store formats[29:17]
For Bloomingdale's and Blue Mercury, Spring wants to lean further into affluent and luxury customers[29:22]
He aims to remove non-consumer-visible costs through automation and reduced complexity, to free resources for better customer experiences across channels[29:27]

Definition of bad and irrelevant stores

Dubner quotes Spring saying he loves stores but 'bad stores are bad stores', and asks what makes a store bad or irrelevant[29:52]
Spring defines an irrelevant store as the last store open in a mall, built for a different era (e.g., 1965) with end-of-life infrastructure[29:56]
• He cites examples: a 37-year-old roof on a 30-year lifecycle, elevators that do not work, and escalators breaking multiple times a year
He adds that when desirable brands refuse to sell to Macy's, leaving only private labels and brands unconcerned with distribution quality, that also makes a store bad[30:13]

Awareness versus conversion problem

Dubner cites a 1,200-person consumer survey showing Macy's brand awareness at 88 percent but measures like popularity, usage, loyalty, and buzz only in the 20-30 percent range[30:30]
Spring calls himself a big believer in self-awareness and ambition, saying Macy's spent about 18 months candidly acknowledging what it is not good at[30:45]
He agrees the conversion gap remains and frames the key issues as execution quality, speed of change, and communication of improvements[31:04]

Premortem and existential threats

Dubner introduces the idea of a premortem, imagining failure in advance to identify threats, and asks Spring what could kill Macy's[31:34]
Spring identifies disintermediation as a major threat: brands going directly to consumers and deeming Macy's an unimportant distribution point[32:22]
He says maintaining brand partnerships depends on being attentive, responsive, paying on time, and treating brands with respect[31:52]
Asked to name brands that pulled out, Spring cites Nike, which took an 18-month break before deciding it wanted more distribution points and rebuilding its business with Macy's[32:12]
He names Tory Burch and On Running as brands he would like to add to Macy's, noting both are already in Bloomingdale's[32:48]
To court a brand like Tory Burch, he says Macy's emphasizes the benefits of a multi-brand environment and its scale: 41 million active Macy's customers versus 4 million at Bloomingdale's[32:57]
• Spring notes there are more affluent customers at Macy's than at Bloomingdale's due to Macy's size, and Macy's serves a more diverse customer base
• He describes Bloomingdale's as a slice of America and Macy's as America, arguing Macy's can help brands understand fashion across the country

Vision for a good future Macy's store

Spring wants customers to find a wide variety of assortment without the so-called endless aisle; he prefers a curated 'best aisle' with real variety instead of redundancy[33:37]
He envisions shoppers seeing a handful of items per category with good-better-best options, with sizes in stock and pleasant associates providing efficient checkout[33:51]
He also imagines customers coming with friends, wandering the store, discovering unfamiliar products, and stopping at a cafe, restaurant, or Starbucks[34:10]
Spring wants customers to remember Macy's as reliably there for them when needed[34:18]

Parade 'magic' versus in-store experience

Dubner quotes an analyst who says the parade 'generates magic' but Macy's has struggled to bring similar magic to the shop floor[34:29]
The analyst suggests Macy's runs a fantastic parade but cannot translate that experience into stores[35:08]
Spring accepts the challenge and says the parade should inspire better store experiences, while cautioning that a once-a-year, heavily funded event cannot be replicated daily[35:08]
Asked about using the parade to grow luxury, Spring says he would welcome a brand like Tory Burch participating if they had something to say in the parade[35:30]
He predicts more future integration between parade elements and in-store activities[35:37]
Spring frames Thanksgiving as a season beginning weeks earlier, when consumers need chairs, plates, games and activities, and sees Macy's as having an opportunity to serve those needs[35:58]
• He notes that Black Friday is the kickoff to the final holiday gift-giving period and claims Macy's 'owns' America in conveying that message, with roughly 28.5 to 29 million parade viewers

Setbacks, skepticism, and the difficulty of retail execution

Recent operational setback at Macy's

Dubner notes that last November, a Macy's employee intentionally hid around $150 million in delivery expenses over several years[36:56]
This accounting issue forced Macy's to delay its quarterly earnings report, which Dubner calls bad[36:59]

Cohen's critique of the Bold New Chapter and Macy's slogans

Dubner asks Cohen for his opinion of Spring's Bold New Chapter plan[37:29]
Cohen says he is generally hostile to sloganeering and accuses Macy's of it for over a decade[37:42]
• He cites prior slogans like 'the magic of Macy's' and the 'Polaris strategy', describing the latter as 'more bullshit than real'
Cohen contends there is no substantive 'there there' behind what Spring has publicly outlined[38:00]
He characterizes Spring's stated goals of more relevant assortments as generic 'motherhood and apple pie' statements[38:16]
Cohen says his philosophy is to develop ideas, implement them, measure success or failure, and only tout them publicly once they have succeeded[38:26]
• He warns that otherwise you create expectations that may not be realistic

Recent store visits and the codex of retailing

Cohen says he visited Herald Square a few months ago and several suburban Macy's branches in metro New York to keep his observations current[38:41]
He says those stores looked terrible, though he is told Spring has begun cleaning up their act[39:06]
He praises Spring's prior work keeping Bloomingdale's pristine and up-to-date, and says Macy's is starting to become more clean, neat, and friendly under the new regime[39:36]
However, he stresses that beyond clean, neat, and friendly, the store must be filled with merchandise customers really want to buy[39:51]
Cohen calls this the 'codex of retailing', saying it is enormously difficult and takes years to build teams capable of constantly creating and refreshing assortments[40:02]
• He notes assortments must be recreated almost daily, especially in an era when customer loyalty cannot be assumed
• He observes that pleasing a customer today might bring them back, but angering them once might mean they never return

Jeff Kinney's An Unlikely Story bookstore and Plainville revitalization

Kinney's role in the parade and his bookstore

Dubner notes that Jeff Kinney, author of Diary of a Wimpy Kid, has had a Greg Hefley balloon in the Macy's parade for 16 years[43:06]
Kinney lives in Plainville, Massachusetts and has built a media empire around Wimpy Kid, including books, films, a musical, and games[43:10]
Kinney also operates a bookstore in the center of Plainville called An Unlikely Story, which has been open about nine years[43:33]
He says the store contains very little Wimpy Kid content beyond a statue of Greg; it is mostly a general-interest bookstore[43:41]

Choosing Plainville and history of the site

Kinney moved to Massachusetts in 1995 and chose Plainville by making a Venn diagram of three points: Boston Logan Airport, Providence's TF Green Airport, and his wife's parents in Worcester[44:09]
The intersection of those three locations was Plainville, a town of about 10,000 people[44:03]
The bookstore is on the former site of Falk's Market, built around 1853 and long a beloved local market[44:42]
Falk's Market had been abandoned for about 17 years before Kinney bought and demolished the building to create the bookstore[44:57]
Kinney's initial goal was to construct a nice building with 'Plainville' on the side so the town could feel proud; he did not initially think through the interior use[45:28]
• At one point, he seriously considered making it just a hollow basketball court to save money

Designing a special bookstore and its financial reality

Dubner reports that other people describe An Unlikely Story as an absurdly successful stop on the book-tour circuit, highly sought after by authors[45:56]
Kinney says they created a very architecturally special place, informed by his experience visiting hundreds of bookstores worldwide[46:13]
He aimed to capture what makes a bookstore feel homey, special, and magical, using many old materials so it feels lived-in[46:21]
He notes that being on the route between Providence and Boston makes the store geographically convenient for touring authors[46:33]
Despite cultural success, Kinney says the bookstore is not profitable and loses a six-figure amount each year[46:46]
• He attributes some losses to paying employees fairly and providing healthcare benefits

Expanding into a full downtown redevelopment

Kinney explains that he and his partners are redeveloping the entire downtown center, about four city blocks[47:33]
He calls the plan ambitious, maybe foolish, but exciting, aimed at reviving a depressed downtown[47:40]
Plainville historically had a jewelry industry; one major employer, Whiting and Davis, produced chain-mail dresses including one worn by Tina Turner in 'Mad Max: Thunderdome'[48:20]
Now the center of town is hollowed out; a factory building that stood for about 80 years is about to be demolished as part of the redevelopment[48:27]

Dubner's visit to Plainville and community response

Dubner describes driving from New York to Plainville, passing outlet shops and a mix of nice and run-down houses, then entering a depressing downtown where the attractive bookstore stands in stark contrast[48:53]
Inside the store on a Saturday morning, it is crowded with all ages, busy cash registers, a humming cafe, modern lighting and tech, and nice bathrooms[49:53]
Dubner says that but for the books, one might not guess it is a bookstore, underscoring its multi-use, community feel[50:09]
Kinney hosts a presentation called 'Plainville Center Past and Present' to show redevelopment plans and is nervous that old-timers might be upset[50:17]
He clarifies to Dubner that he 'bought out' other operators only in the sense of being ready when they wanted to move on, not in a hostile way[50:57]
• He says they 'floated the balloon' to property owners, offering to buy when they were ready; for example, the tool factory owners were ready to retire
At the event, Kinney comments that everyone present likely knows more about Plainville's history than he does[51:17]
The town historian, Christine Moore, presents historical images, while Kinney shows renderings of the planned Plainville Square[51:31]
Dubner observes the crowd is older and there is little dissent; instead, people reminisce about hardware stores, factories, and memorable milkshakes[51:43]

Plainville Square vision and investment scale

Outside, Kinney shows Dubner the intersection of Bacon Street and Route 1A, describing it as the future Plainville Square[52:09]
He says they currently have the bookstore and a parking lot, but plan to add an anchor restaurant, beer garden, potential Airbnb, and other buildings[53:31]
Kinney notes they recently demolished seven buildings, leaving the area looking like it had been flattened by a hurricane, but he sees it as a new palette[53:41]
He estimates the redevelopment will cost between $17 million and $35 million, though the precise budget is not yet known[55:10]
Kinney says he rarely talks with friends or family about what else he could have done with that money and believes people respect that they are investing in the town's infrastructure[55:10]
He is motivated by the idea of changing the town not just for the current generation but for generations to come[55:38]
• He cites the proverb that a society becomes great when old men plant trees whose shade they will never enjoy

Community events at the bookstore and local perceptions

Jason Tatum author event at An Unlikely Story

On the day of Dubner's visit, crowds gather for an event with Boston Celtics star Jason Tatum, who has written a children's book called 'Baby Dunks a Lot'[55:10]
Tatum is described as one of the best, richest, and most famous athletes in the world, fresh off a Celtics championship and an Olympic gold medal[56:36]
The event draws hundreds of people lining up around the block, and Kinney himself moderates the Q&A, as he does for high-magnitude authors[57:06]
Tatum says he has played basketball in front of thousands but feels a bit nervous appearing as an author for the first time[57:24]
Tatum had pre-signed hundreds of books and did not stay long after, but the store remained open late and the crowd continued shopping[57:12]

Voices from the community

A young attendee says Jason Tatum is his basketball hero and he wants to be in the NBA like him; he is also thrilled to see Tatum and Jeff Kinney together, as Kinney is his favorite author[58:06]
Another visitor, Izzy Gaudette, comments that the store has so much, from books to non-books, and says she will have to come back[59:34]
Local resident Chris Alba recalls that the corner used to have a very dilapidated building and now looks totally redone, popular, and 'awesome'[58:55]
Kinney says Plainville has enormous room for improvement and that in a wealthy place like Beverly Hills he would have little interest in such a project, but in Plainville they can have an outsized impact[59:48]

Physical retail versus digital, and parallels between Plainville and Macy's

Resilience and appeal of independent bookstores

Dubner notes that independent bookstores, once closing rapidly, have been on the rise and weathered the COVID period relatively well[59:54]
He suggests that as the world becomes more digital, fast, consolidated, and connected, there is a counter-push toward handmade, homemade, and community experiences[1:00:24]
Kinney agrees that people are craving connectedness and is surprised by the long-tail effects of COVID[1:00:58]
• He observes that many twenty-somethings who missed in-person milestones like high school graduations now want jobs where they work physically with peers
Kinney sees bookstores as part of that in-person experience and argues that the book-buying experience cannot be replicated online[1:00:36]
• He likens it to the record-buying era, when people flipped through albums, admired artwork, and listened to music overhead, which he says was better than digital alternatives

Comparing Macy's corporate reinvention to Plainville's experiment

Dubner points out that Macy's, like Kinney, is trying to build spaces where people want to be with other people doing activities that declined during the digital revolution[1:02:26]
He asks if Kinney sees any connection between his project and a big corporate entity like Macy's reinventing its future[1:02:32]
Kinney says a major beer operator is interested in locating in downtown Plainville because if they are there, they can be 'the thing that people do' in town[1:03:35]
• The beer company told him that in larger cities like Boston they would compete with dozens of other restaurants, but in Plainville they can be the main attraction
Kinney believes that if they 'set the table just so', they may attract unexpected partners, possibly including Macy's[1:03:35]
He frames his central question as whether investing in a downtown can change the fate and self-image of a town and make it a model for others, and says this will likely be his life's work[1:03:16]

Closing reflections: Macy's, Plainville, and the parade's significance

Spring's reaction to Plainville and small-town retail mix

Dubner notes that Macy's turnaround slogan, 'a bold new chapter', could almost have been the name of Kinney's bookstore, while 'an unlikely story' might also fit Macy's situation[1:03:55]
He asks Spring what he thinks of Kinney's Plainville project and whether Macy's might open some kind of store there[1:03:35]
Spring says Macy's is always open to evaluating real estate opportunities and applauds what Kinney is doing, expressing a desire for vibrant towns across the country[1:03:48]
Spring says he still lives in Westchester County, where many main streets now have more banks, restaurants, and nail salons than anything else[1:04:54]
He says he misses the candy store, bookstore, and record store, and sees retail variety as creating reasons for strolling and spending locally[1:05:11]
He wishes Kinney the best and advises him to follow the adage from the TV show 'Cheers' to know everybody's name, saying those little touches determine where people choose to shop again[1:05:06]

Uncertainty of outcomes and parade-day plans

Dubner notes it is hard to predict the future for either Macy's or Plainville; both Spring and Kinney are investing heavily in turnarounds, but people and markets are fickle[1:05:06]
He adds that generally you do not succeed in the future by mimicking the past[1:05:32]
On Thanksgiving, Spring says he will attend the parade with his wife, possibly some in-laws, Macy's leadership, and others, sitting in the grandstand to watch the parade reach 34th Street[1:01:48]
Kinney describes the hypnotic effect of giant helium balloons moving between buildings and the excitement of their outsized scale[1:01:52]
He says the parade represents legitimacy for a brand: participating over time feels like proving you belong among major cultural properties[1:02:32]
Kinney mentions befriending Jeannie Schultz, widow of Charles Schultz, and calls the group of parade property creators a small club[1:03:00]

Updates on Plainville project and Macy's performance

Dubner reports that Kinney provided an update: the construction site they visited now has a built-out beer garden, with plans to open in the spring[1:03:42]
He also reports that Spring closed 64 Macy's locations this year and announced earnings upticks across Macy's, Bloomingdale's, and Blue Mercury[1:03:55]
Cohen says we will have to wait to see whether this is a 'dead cat bounce' or something more enduring[1:04:00]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

A retail brand must stand for something clear and differentiated in customers' minds; high awareness without a compelling, consistent value proposition leads to weak loyalty and poor conversion.

Reflection Questions:

  • • What do the people you serve currently think your product, service, or organization actually stands for?
  • • How could you sharpen or simplify your value proposition so that it is both memorable and meaningfully different from your closest competitors?
  • • What is one concrete change you could make this quarter to align your everyday customer experience with the story you want your brand to tell?
2

Cleaning up the basics of execution-first impressions, physical condition, staffing, and reliability-is a prerequisite before more sophisticated strategies like branding campaigns or complex assortments can succeed.

Reflection Questions:

  • • Where in your business or work is the 'parking lot' dirty-what first impressions might be undermining trust before you ever deliver value?
  • • How would your outcomes change if you focused the next 30 days on fixing obvious, unglamorous operational issues before launching anything new?
  • • Which one frontline touchpoint (a lobby, homepage, intake form, or onboarding step) could you upgrade this month to immediately improve how people experience you?
3

Long-term partner relationships depend on mutual respect and fairness; extracting one-sided concessions may work in the short run but pushes suppliers and collaborators to seek alternatives as soon as they can.

Reflection Questions:

  • • In your current partnerships or vendor relationships, where might you be taking more value than you are giving back?
  • • How could you redesign one key agreement so that both sides feel their interests and risks are being fairly recognized?
  • • What is one specific behavior-such as faster communication, on-time payments, or better presentation of others' work-you could adopt to become a partner people are eager to work with long term?
4

Place-based, community-focused investments can create cultural and economic value even when the direct business economics are weak, but they require a clear long horizon and personal commitment rather than quick financial payoffs.

Reflection Questions:

  • • What community or ecosystem around you could benefit from the kind of long-horizon investment that will not pay back quickly but could change the environment over decades?
  • • How might your expectations and decision criteria shift if you evaluated one project not only on its direct profit potential but on its impact on people and place 20 years from now?
  • • What small 'tree' could you plant this year-a space, program, or habit-that future colleagues, neighbors, or customers might one day take for granted as essential?
5

Announcing grand strategies before they are proven can create expectations and skepticism; iterating quietly, measuring results, and then communicating successes builds credibility and trust.

Reflection Questions:

  • • Where in your work have you been tempted to promote a new initiative before you have evidence that it actually works?
  • • How could you design one current project so that you test it on a small scale, learn from the data, and only then broadcast the results more widely?
  • • What is one bold claim or slogan you are using now that you might replace with a concrete, validated example of progress instead?

Episode Summary - Notes by Logan

Dying Is Easy. Retail Is Hard. (Update)
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