“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.