Chae Initiative Students Explore Private Sector Entrepreneurship in New York

The Chae Initiative in Private Sector Leadership, part of The Tsai Leadership Program at Yale Law School, held its second annual trip to New York City in January to immerse students in the world of private sector leadership.

Over the course of four days, students met with successful entrepreneurs and C-suite leaders, networked with YLS alumni, and learned from professionals across the private sector landscape.

“There are so many successful alumni from YLS who are business leaders,” said Mary Herrington, Co-Head of The Tsai Leadership Program and Executive Director of the Chae Initiative. “We have students who wish to pursue business careers straight after graduation and some who intend to start out in law and then pivot. Through these onsite visits, students could see results of both paths and gain insights into the types of skills and experience that are vital to leading business enterprises.” 

Last year, the immersive trip focused on leadership in the finance industry. This year’s guiding theme, said Herrington, was entrepreneurship and business operations. 

On the first day, students headed to the Barclays Center to attend a Brooklyn Nets game at the invitation of Joe Tsai ’90, governor of the Brooklyn Nets and chairman of BSE Global, which owns the team. The Nets faced the Portland Trail Blazers, and although they lost 134-127, it was “very much a community bonding experience” that set the tone for the trip, Herrington said. After the game, the students had an opportunity to hear from Tsai about the challenges and opportunities of managing multinational companies, as well as how to make the most of their time at law school.

“Meeting Joe Tsai and hearing his story — from being a tax lawyer at Sullivan & Cromwell to a co-founder and now-Executive Chairman of Alibaba — was inspiring,” said Denise Jimenez ’25, a Chae fellow who hopes to practice law in the finance sector after graduation.

The students’ second day began with a workshop with author and speaker Gretchen Rubin ’94 on the topic “Communicating Better at Work.” The workshop was based on the principles of Rubin’s book The Four Tendencies adapted to workplace settings. Students broke into small discussion groups before coming back together to share notes with the group. 

That afternoon, students attended a company visit with Bryan Leach ’05, the founder and CEO of Ibotta, hosted by Ibotta investor Great Oaks Venture Capital. Leach, who flew in from Denver specifically for the event, spoke to students about his personal career journey. Leach said he began his career in pursuit of “gold stars” through legal academia and clerkships, and eventually as a partner at the law firm Bartlit Beck. Ultimately, Leach explained, he chose a nontraditional career path, leaving a law firm partnership to put all his efforts into Ibotta, a choice that entailed some risk, but which also meant pursuing a meaningful goal that he knew he would never regret. 

Chae fellow Federico Roitman ’25 said the trip had prompted him to think about possible alternatives to a traditional career in law. 

“I was particularly drawn to the stories the founders shared about their experiences getting their ventures off the ground, the risks they took, and how their YLS degrees helped prepare them to take a ‘nontraditional’ path following law school,” Roitman said. “Taking the risk and building something from the ground up can be intimidating, uncertain, and challenging, but seeing how passionate each founder was also highlighted to me how energizing it can be.”

That evening, the students attended a reception and dinner at The Yale Club, where Dean Heather K. Gerken spoke about the mission of the Chae Initiative — to empower students to translate theory into practice, while navigating complex business issues — as well as the rich community of support backing the initiative and supporting its student fellows.

On the trip’s third day, the students visited the Blackstone Group headquarters to meet with Michael Chae ’97, who organized a half-day of meetings with the investment firm’s senior leadership. For the second year in a row, Blackstone’s chairman and CEO, Stephen Schwarzman, met with students and shared reflections on his career and leadership lessons in conversation with Chae. Each student also received a copy of his book, What it Takes: Lessons in the Pursuit of Excellence. 

In the afternoon, the group headed to the offices of Priori Legal, where they were met by CEO and co-founder Basha Rubin ’10 and Chief Product Officer and co-founder Mirra Levitt ’10. Rubin and Levitt talked about their company’s evolution and growth — from a two-person venture started by classmates to one of the nation’s fastest-growing private legal tech companies that, in 2023, was named New Law Company of the Year at the Legalweek Leaders in Tech Law Awards.

That evening, the group had dinner with Frank Washington ’74, the founder and CEO of Crossings TV. Washington spoke about his journey after Yale Law School, which began in Washington, D.C. in the practice of law and a role in the Carter administration and eventually to a successful career in broadcast radio and television.

On the final day of the trip, the students met for lunch as a group to reflect on the experiences of the past several days. 

“I had each student share three of their most memorable lessons from the week,” said Herrington. “All of them noted that one of the most rewarding experiences was the feeling of camaraderie and collegiality amongst the group.”

That community extends from the Chae fellows to the broader alumni community, Jimenez noted.

“I came away from the trip with a sense of immense gratitude. So many alumni were willing to speak with us and offer their help,” she said. “One of my biggest takeaways was how incredible a network we have at YLS, and how numerous the possibilities are for us as students at this institution. We have the resources and the connections to make any ambition a reality, and everywhere along the way we will have opportunities to both receive and give help.”

“One of the law school’s greatest gifts is its community of students and alumni. The New York City trip builds fellowship across the generations,” said Professor of Law John Morley ’06, Faculty Director for the Chae Initiative in Private Sector Leadership. “It’s wonderful to see students connecting with each other and with extraordinary alumni mentors.”

Roitman said that he was struck by how the people they met on the trip approached opportunities to take a risk or make a major change. 

“They approached them with openness and curiosity, [and] they were not afraid to ask ‘what if?’ even if it meant deviating from the path they were on,” Roitman said. “I hope to carry this mindset with me as I embark on my career after graduating from YLS.”