Screenshot 2025-10-20 at 7.58.47 AM

- 34:42

Trends

or listen on

“Flat Is the New Up”: Richard Kestenbaum on Retail’s Uncertain Holiday Season

📍New York, US

As retailers gear up for the 2025 holiday season, optimism is in short supply. Inflation, tariffs, and an anxious consumer base are shaping what could be another volatile quarter for the industry. In the latest episode of OFFBounds, Paula Macaggi sits down with Richard Kestenbaum, Partner at Triangle Capital and longtime investment banker, to discuss why this year’s sales forecasts demand a more cautious, realistic lens. “Flat is the new up,” Kestenbaum says, pointing out that much of the apparent growth is simply inflation-driven rather than real volume.

Kestenbaum, who has advised on mergers and acquisitions across the consumer and retail sectors for decades, brings both a financial and behavioral perspective to the table. He explains how rising prices and tariff uncertainty are forcing companies to pull back on inventory commitments, limiting discounts and changing the rhythm of holiday promotions. “Retail is in rough seas,” he says. “Smart players are staying conservative.” Meanwhile, consumers are feeling the squeeze of higher grocery bills and limited wage growth, creating a bifurcated market where upper-income households continue to spend while everyone else cuts back.

Beyond short-term pressures, Kestenbaum points to a deeper transformation reshaping the industry: the role of technology and AI. From supply chain optimization to pricing strategies, automation is becoming the key lever for efficiency. But it’s also creating cultural challenges inside organizations. “AI isn’t a fad,” he tells Paula. “It’s changing every job in retail. The question is how fast people can adapt.” This period of uncertainty, he argues, is forcing both brands and investors to rethink what long-term success looks like — not just in sales numbers, but in how they manage cost, talent, and innovation.

For Kestenbaum, survival in 2025 isn’t about taking bold risks; it’s about getting through turbulence in one piece. “This is not a season for maximization. It’s a season for survival,” he says. His advice for retailers: stay disciplined, protect margins, and invest in technologies that lower cost structures. Because when the market stabilizes — and eventually it will — those who have built resilience will be the ones positioned to grow.

Listen more

Interview

Coterie: When Product, Brand, and Experience Align

A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

Interview

A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

Coterie: When Product, Brand, and Experience Align

A key theme behind Coterie’s success is the power of messaging. While many brands focus heavily on channels, Ankur emphasizes that growth begins with clearly communicating the value you create.

Interview

How Helzberg Uses Technology to Remove Frontline Burden

Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

Interview

Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

How Helzberg Uses Technology to Remove Frontline Burden

Under Ryan Holm's leadership, the 111-year-old jewelry retailer has invested in technology that removes administrative burden while protecting human connection.

Interview

How HANRO US Used Streaming Ads and Clienteling to Accelerate Growth

Growth has not come from nostalgia alone. Under Satanas’ leadership, HANRO USA invested in modern acquisition channels while playing the long game on brand building. Paid social laid the foundation, but streaming ads delivered a breakthrough moment.

Growth has not come from nostalgia alone. Under Satanas’ leadership, HANRO USA invested in modern acquisition channels while playing the long game on brand building. Paid social laid the foundation, but streaming ads delivered a breakthrough moment.

Interview

Growth has not come from nostalgia alone. Under Satanas’ leadership, HANRO USA invested in modern acquisition channels while playing the long game on brand building. Paid social laid the foundation, but streaming ads delivered a breakthrough moment.

How HANRO US Used Streaming Ads and Clienteling to Accelerate Growth

Growth has not come from nostalgia alone. Under Satanas’ leadership, HANRO USA invested in modern acquisition channels while playing the long game on brand building. Paid social laid the foundation, but streaming ads delivered a breakthrough moment.

Interview

Inside Westwing’s Turnaround: The Decisions That Changed Everything

At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

Interview

At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

Inside Westwing’s Turnaround: The Decisions That Changed Everything

At the center of this transformation sits an unusual balance of rigor and creativity. Hoerning often describes it as the tension between data and intuition.

Trends

The Rise of Brand Memberships and the Future of Customer Loyalty

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

Trends

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

The Rise of Brand Memberships and the Future of Customer Loyalty

Brand memberships are having a moment in retail, and it is not a passing one. Across fashion, beauty, grocery, and home, brands are moving beyond traditional loyalty programs built on points and discounts and instead creating paid or value-based memberships that promise access, belonging, and emotional connection.

Receive new exclusive episodes


Sign up for our newsletter now!

Privacy Overview

This website uses cookies so that we can provide you with the best user experience possible. Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful.

Strictly Necessary Cookies

Strictly Necessary Cookie should be enabled at all times so that we can save your preferences for cookie settings.

3rd Party Cookies

This website uses Google Analytics to collect anonymous information such as the number of visitors to the site, and the most popular pages.

Keeping this cookie enabled helps us to improve our website.