How Dollar Tree Plans to Thrive Despite Breaking the Buck

In April 2024, writer, podcaster, and entrepreneur Tim Ferriss—known for his hugely popular podcast “The Tim Ferriss Show” and NYT-bestselling books like The 4-Hour Workweek—found himself at a crossroads. Although his podcast was generating millions annually, he questioned the sustainability of podcasting and his own competitive advantage given the increasingly saturated market and the advent of AI tools and video-centric formats. He faced a difficult choice: innovate from within his proven format, pivot to entirely new ventures—possibly in film, premium consumer products, or venture capital—or risk a slow decline by maintaining the status quo. Complicating matters further was Ferriss’s desire to start a family, a goal he prioritized above all business ventures. Every month of indecision narrowed his window for successfully transitioning. Senior Lecturer Reza Satchu and Tim Ferriss joined Cold Call host Brian Kenny to discuss the case, “Tim Ferriss: What Might This Look Like If It Were Easy?”

For 35 years, Dollar Tree, a discount retail chain selling general merchandise, had held its fixed price point steady, charging $1.00 for its ever-changing assortment of household items, food, stationery, books, seasonal items, gifts, toys, and clothing. That changed in late 2021, when the company announced that Dollar Tree was raising prices on all goods to $1.25. Harvard Business School Senior Lecturer Jill Avery joins host Brian Kenny to discuss whether the retail chain could remain relevant to its price sensitive shoppers through smart marketing, pricing, and branding strategies in the case, “Dollar Tree: Breaking the Buck.”

In the winter of 2023, Lyft was facing declining market share and financial pressures. Enter new CEO David Risher, who took the helm amid low morale and limited resources. His challenge: reignite innovation, refocus the culture, and find new ways to stand out in an industry dominated by Uber. Harvard Business School professor Ranjay Gulati joins host Brian Kenny to discuss the case “Lyft 2023: Roads to Growth and Differentiation.” They explore how Risher led during a strategic crossroads, making bold decisions, putting the customer front and center, and shaking loose old habits. Gulati also shares insights from his new book, “How to Be Bold,” illustrating how courage becomes a competitive advantage in times of uncertainty.

How do you scale innovation in a system where critical pieces are out of your control? That is the challenge Highland Electric Fleets faced as it worked to replace diesel school buses with electric vehicles across the United States. While Highland provided financing, infrastructure, and fleet operations, success depended on external partners, including manufacturers, utilities, and districts. Delays and disruptions forced the company to stay nimble and deliver under pressure. Harvard Business School professor Rosabeth Moss Kanter and Highland Electric founder and CEO Duncan McIntyre join host Brian Kenny to discuss the HBS case “’The Wheels on the Bus’ Go Electric.” They explore what it takes to scale a climate solution while sustaining momentum and coordinating across public and private sectors.

Atlassian promised employees they could work from anywhere, permanently. By 2024, its data-driven routines and workplace experiments were shaping both its culture and its products, turning the company into an innovation lab. Now it faces a new challenge: helping customers adopt these practices, which requires hands-on support, strategic advising, and cultural change. Harvard Business School Associate Professor Ashley Whillans joins host Brian Kenny to discuss the case “Designing the Future of Work: Atlassian’s Distributed Work Practices” and the questions Atlassian’s leaders must answer as they try to scale what works.

When Happi Co. CEO Sam Rockwell partnered with Snoop Dogg and his son, Cordell Broadus, to launch Dr. Bombay Ice Cream, the team set out to disrupt a stagnant market with bold flavors and culturally resonant branding. With national retail placement and projected first-year sales of $20 million, the brand quickly made its mark. Now, as Rockwell plans the next phase—marketing, fundraising, and expanding into new markets—he must also navigate the dynamics of a creator-led brand, balancing roles and staying nimble and authentic. Sam Rockwell and Harvard Business School professor Bill Kerr join host Brian Kenny to discuss Kerr’s case, “Dr. Bombay Ice Cream,” which explores the launch and growth of a lifestyle brand built on cultural storytelling and entrepreneurial ambition.

Shake Shack began in 2001 as a single hot dog cart in New York City and grew into a global fast-casual chain known for quality ingredients and a strong hospitality ethos. In 2024, following a rapid digital transformation that introduced kiosks, mobile ordering, and app-based personalization, Chief Growth Officer Stephanie So wondered whether the model they had built was truly ready to scale—or still needed refinement. With a new CEO focused on ambitious growth, the company faced key questions about how technology might support or undermine the Shake Shack experience for both guests and employees. HBS Professor Christopher Stanton joins So and host Brian Kenny to discuss the case “Shake Shack’s Playbook for the Digital Era,” and what it takes to grow a hospitality-driven brand in an increasingly automated industry.

During a busy travel season, digital travel platform Booking.com tried a risky experiment that meant changing the site’s landing page. Then CEO Gillian Tans made the decision to lean into the company’s “test everything” culture—even if it meant failure. In this episode from 2019, HBS Professor Stefan Thomke and host Brian Kenny discuss the case Booking.com. They explore how past experience and intuition can be misleading when attempting to launch something novel. Instead, innovative firms embrace a culture where testing, experimentation, and even failure are at the heart of what they do.

Ming Min Hui, executive director of Boston Ballet, is unique in her field. As a young, Asian American woman with a HBS MBA and a background in finance, she focuses on ensuring the ballet company stays true to its art form and still relevant to its times. Hui had worked for eight years at Boston Ballet as chief of staff and chief financial officer before taking the helm. Now leading one of the foremost ballet companies in the U.S., she confronted evolving demographics, shifting audience habits, and an increasingly challenging financial environment. Harvard Business School Assistant Professor Edward Chang and Hui join host Brian Kenny to discuss the case Ming Min Hui at Boston Ballet. They explore how she balances the past, present, and future—and how these lessons translate from this nonprofit arts organization to any company, anywhere.

Bill Wilson was an incredibly entrepreneurial young man with tremendous potential. He was also a drunk, until an epiphany made him sober. With his personal drive and fellowship with former drinking buddies, Wilson built a social movement and worldwide organization. Founded in 1935, Alcoholics Anonymous has helped millions of “friends of Bill” recover from alcohol addiction. In this episode of Cold Call, HBS Professor Robert Simons joins host Brian Kenny to discuss the case, “Bill Wilson: Changing the World.” They explore how Wilson navigated life’s choices, transformed his life and those of others, and left a lasting impact on the world.