Alumni Share Leadership Lessons from Entrepreneurship Journeys

In October, the Michael S. and Alexa B. Chae Initiative in Private Sector Leadership, part of Yale Law School’s Tsai Leadership Program, held its Entrepreneurship Weeks event series in which students heard Yale Law alumni speak about their career trajectories as innovators.

Mary Herrington, executive director of the Chae Initiative, curated the programming with the idea of expanding students’ exposure to different entrepreneurship paths. With more law students becoming interested in exploring career paths in entrepreneurship, the Chae Initiative strives to expand students’ frameworks, according to Herrington. 

“We wanted to highlight different forms of entrepreneurship, including the scalable start-up model, the acquisition model, the innovative model, and the adoptive model, to name a few,” Herrington said. “We also wanted to cover different industries, from tech to finance to consumer products as well as scale, including small to medium-size companies and those that are larger and venture-backed.” 

The Chae Initiative’s series held between Oct. 16 and Oct. 30 featured alumni from a wide variety of fields, ranging from tech to environmental sustainability. First in the series was a conversation with Madhuri Kommareddi ’12, COO of Teamshares, a fintech company that works in small business acquisition with the goal of generating wealth for employees through a stock ownership system.

Moderated by Visiting Lecturer in Law A.J. Wasserstein on Oct. 16, Kommareddi spoke at the event about her professional path working in government service before making the leap to the private sector as a director at BlackRock and now currently as a company leader at Teamshares. Kommareddi was able to share how fulfilling it has been to help build Teamshares as well as invest in small-to-medium size businesses from retiring owners.

The series’ second event on Oct. 19 kicked off with remarks by Dean Heather K. Gerken ahead of a moderated talk with Jay Koh ’98, the co-founder and managing director at The Lightsmith Group, one of the first private equity firms created with an explicit focus on climate change adaptation. 

“What’s most common among our graduates is that they do pursue what’s uncommon,” Gerken said. “And that’s what makes Jay [Koh]’s career so remarkable. He figured out what he was built to do, and he became a leader in his field.”

During the event moderated by Joseph M. Field ’55 Professor of Law Doug Kysar, Koh spoke about his unusual career path and the need for students to have a mindset open to alternative opportunities. He shared that his work with the Overseas Private Investment Corporation, a former federal agency, was an unforeseen opportunity following the 2008 financial crisis that wound down the Global Principal Strategies Division at Lehman Brothers, a role that brought him to London after a prolific career at The Carlyle Group. This seismic economic crisis became a catalyst for his immersion in climate crises and sustainability investment work, now the strategic focus of his investment firm. 

“Life and circumstances will sometimes choose strategies for you,” Koh told the audience. “And so being open to that and having the mental space, agility, and orientation to pursue those opportunities, I think, is something that’s worth considering.”

On Oct. 24, students heard from Jane Park ’96, a serial entrepreneur and nationally recognized speaker on consumer brands and social commerce. Park currently serves as founder and CEO of Tokki, a sustainable gift wrap company, but her entrepreneurial career began in 2007 when she launched Julep, her first business which she expanded from regional nail salons to a nation-wide beauty brand distributed at Sephora, Nordstrom, Ulta, and QVC. In 2016, Park led Julep to a private equity exit to a beauty rollup funded by Warburg Pincus. 

During the talk led by Professor of Law and Chae Initiative Faculty Director John Morley ’06, Park shared the uphill battles she faced in forging a career as a business owner — from dealing with the day-to-day decisions as a team leader to weathering the global financial crisis — and how she navigated her journey from one opportunity to the next. 

“As the CEO of a venture-backed company, you’re juggling the needs of your investors, the needs of your employees, your hopes and dreams for what you want to achieve and society,” Park said. “And that’s always a tricky balance.”

Matt Beck ’25, a Chae Fellow, attended multiple events during the Entrepreneurship Weeks series. He said the talks have helped him not only gain a better understanding of private sector entrepreneurship as a potential career path, but they also helped build his professional network. 

“The best part of Entrepreneurship Week was being able to build these personal connections,” Beck said, for whom Park’s talk was a highlight. “To go to lunches, to go to receptions with the entrepreneurs who came to speak, because succeeding as an entrepreneur really requires being able to rely on mentors and peers.” 

The event series concluded with a conversation moderated by Morley with Basha Rubin ’10 and Mirra Levitt ’10, co-founders of Priori Legal, a legal tech company that they lead together as CEO and CPO, respectively.

The idea for Rubin’s and Levitt’s joint business came from their realization that there was a need for a digital marketplace specifically for legal counsel, an observation that emerged during their clinic work as Yale Law students. 

Levitt said she enjoyed her work as a lawyer at Covington & Burling, but that was outweighed by her conviction in their startup idea. “We thought that being able to find the right lawyer was really important for businesses and that there wasn’t a good structure for doing that,” Levitt said. 

Rubin and Levitt spoke about the inner workings of their business and their experience advancing the company over the past decade. Priori Legal now encompasses a vetted network of attorneys in 70 countries and all 50 states and has expanded to develop a software product for lawyers and firms to engage clients via their Priori network. 

The series closed on Oct. 30 with a workshop led by Jordana Confino ’15, founder of JC Coaching, a consulting firm that works with lawyers and law students to achieve positive self-development.

“You may not be surprised to hear that perfectionism is incredibly pervasive in the legal industry,” Confino said during the workshop. “It’s also true that perfectionism is …. absolutely lethal for aspiring entrepreneurs.” Students learned about the different tools that they can use to weed out internal pressures, such as perfectionism, and to develop a positive mindset. 

The events showed students that there is no one right way to build a career. Chae Fellow Deja Morehead ’25, who attended the talks by Koh and Park, said the events allowed her to consider nontraditional career paths. 

“One thing about going to Yale Law School, it’s not just preparing us to be lawyers, it’s preparing us to be leaders,” Morehead said. She added that meeting the alumni was encouraging for students interested in pursuing a more unconventional path, and “gives us permission and space to pursue things without fear.”