Cold Call

Katie Holyfield and Taylor Matkins founded Lucky Ones Coffee in 2017, a coffee shop with a mission to create jobs in Park City, Utah, for people with intellectual and developmental disabilities. The company quickly earned strong support from the local community, and by early 2023, Holyfield and Matkins employed 17 people across two coffee shops. The two entrepreneurs must now decide how to grow their business to create more jobs and how to structure the business to ensure that it remains a sustainable and financially sound enterprise as it scales.

Sequoia Capital, a venture capital firm founded in 1972, grew to become one of the most storied venture capital firms in the world. The firm’s investment track record includes the names of some of the largest global companies. But the venture capital industry began facing new challenges in 2022, and investors were increasingly cautious. At that time Sequoia also began restructuring the firm and made other changes to their core identity. What would all of this mean for the future of Sequoia, and would the firm still be able to maintain their historical dominance?

Early in her career Brooke Boyarsky Pratt (MBA 2013) enjoyed considerable success in roles at McKinsey and Berkadia, a Berkshire Hathaway portfolio company. But a routine visit to the doctor in 2020, where she experienced weight stigma yet again, led her to address the problem of obesity care. Boyarsky Pratt had struggled with her weight since she was young. So when she started knownwell, an integrated weight and primary care provider that was designed to support people with obesity, it was a huge step for her both personally and professionally. In the spring of 2023, knownwell opened its first weight-inclusive clinic in the Boston area. But Boyarsky Pratt had to make a fundamental decision on how she wanted to grow the company. Should she grow slowly and build a small footprint of clinics in the Boston area over the next few years? Or should she scale fast to potentially help millions of people across the U.S.?

In 2017 Fawn Weaver launched a premium American whiskey brand, Uncle Nearest. It became the fastest growing and most awarded whiskey brand in America, despite the challenges Weaver faced as a Black woman and outsider to the spirits industry, which is capital-intensive, highly regulated, competitive, and male-dominated. In October 2023, Weaver announced plans to expand into cognac with the goal of building the next major alcoholic beverages conglomerate. But the company was still heavily reliant on capital. How could Weaver convince new investors that her plans for cognac would yield success?