For Entrepreneurial Alumni, Yale Law School Values Illuminate the Path Less Traveled

July 16, 2025

When Sander Daniels ’09 was a 1L student at Yale Law School, he and his friends began brainstorming ideas for a company that they hoped would create economic opportunity and serve the greater good.

Recognizing a need for quality jobs available to everyday citizens, Daniels co-founded Thumbtack — an online marketplace for local home services — out of his student apartment on Orange Street during his second year of law school. Today, the company is a leading home services website with a valuation of $3.2 billion.

Though Daniels found success in the tech business world, he said the Silicon Valley path was a route few dared to venture at the time, especially when the country was in the throes of a deep financial crisis.

“I had to strike out on my own,” said Daniels. “It was clear that the country needed smart, ambitious people to create jobs, and I thought that my talents would be best used to create great, dignified work for as many people as possible.”

This call to blaze an independent path, fueled by the pursuit of public service and excellence, is inherent in the spirit of Yale Law School and has inspired generations of entrepreneurial alumni to use their keen lawyering skills to make the world a better place.

Bryan Leach ’05, founder of Ibotta

Answering the Call to Lead

Yale Law School aims to shape its students into the world’s leading problem-solvers and trailblazers, whether that be in law or other careers.

“At Yale, you’re broadly encouraged to be a leader in society, whatever that means to you,” said Daniels. “For me, that meant making an impact in business and creating jobs for people.”

In an effort to bolster the Law School’s students’ leadership skills and the growing community of alumni who follow an unconventional career path, the Law School established The Tsai Leadership Program in 2021 under Dean Heather K. Gerken. The program provides support through a wide variety of curricular offerings, practical skills training opportunities, and alumni mentorship and networking, and includes the Ludwig Program in Public Sector Leadership and Chae Initiative in Private Sector Leadership programs, which support students wishing to pursue nontraditional careers and various leadership roles.

Bryan Leach ’05, who mentors students through the Chae Initiative, credited the Law School for giving him the skills he needed to be a leader in the business world and is thrilled to see its leadership initiatives grow under Gerken’s deanship.

After making partner at a prominent trial law firm at only 32 years old, Leach felt compelled to do more.

“I felt that I have a moral obligation to take more risks,” said Leach. “You can only fall so far with a Yale Law degree — I thought maybe I, of all people, with the level of extreme privilege that I’ve had, should be trying to better the world and taking chances.”

It was that idea that prompted Leach to pursue an entrepreneurial career that would use his skills to provide a public service. He went on to found Ibotta, a Denver-based tech company that, to date, has given more than $2.3 billion in cash back rewards to consumers for their everyday purchases in the grocery store. In April 2024, it became the largest tech IPO in Colorado history when it went public on the New York Stock Exchange.

Founding a tech business in Colorado without a business background, capital, or a safety net felt like a seemingly impossible task, but Leach believed in his vision and abilities thanks to his Law School background. He was also drawn to breaking away from the pigeonholing that often happens in the legal field and blazing his own path — and leading others to do the same, by example.

“You don’t have to let society define you narrowly,” said Leach, who reiterates that message to students when he visits the Law School. “You can break out of the mold and trust yourself to succeed, and I think the Law School has been doing a great job of instilling that in its students.”

An Indelible Intellectual Culture

For many alumni, the environment of intellectual curiosity that is distinct to Yale Law School has left a lasting impact on their professional practice.

Jane Park ’96 — the founder of Julep Beauty, a clean makeup and skincare brand, and Tokki, a sustainable giftwrap company — said this impact manifested in making curiosity a part of her daily practice, a routine she honed while at the Law School that enabled her to constantly innovate her businesses for the better.

“Intellectual curiosity was such a core of the Yale Law School experience for me,” she said. “Having the time to really question deeply and thoughtfully — not just at a surface level — became helpful when growing my companies.”

Those critical thinking skills were also paramount for Basha Rubin ’10 in founding her company Priori — an online marketplace that made access to legal services more transparent, cost-effective, and efficient — just a few years after graduation.

“At Yale Law School, I was encouraged to push boundaries and never accept an answer for what it is, and to try to look at every problem from as many different angles as possible,” said Rubin, who started Priori with her classmate Mirra Levitt ’10. “That way of thinking, which I think is unique compared to other kinds of legal education, was something I really cultivated as a law student and it has served me extraordinarily well in my entrepreneurial journey.”

Public Service Through Problem-Solving

The culture of the Law School lends itself to the solutions-oriented mindset that is ingrained in students and alumni alike.

“You get a great analytical framework for how to think about complex problems — and how to think creatively about solutions,” said Madhuri Kommareddi ’12, who currently serves as the Chief Operating Officer at Teamshares — a fintech company that helps small business employees acquire stock wealth. She said she found the optimism of her classmates and professors in creating real-world solutions to be inspiring, and she’s carried that positive mindset into her career. “I think the training that you get in law school, and learning to approach problems as an optimist and with creativity, gets people most of the way in the business and entrepreneurship world,” she added.

Many alumni, like Songe LaRon ’10, have used this framework to launch their businesses by identifying a problem and creating a solutions-based mission.
After working as a corporate lawyer for a few years after law school, LaRon wanted to make a shift to the tech business world and began brainstorming ideas for a company with his business partner, Dave Salvant. The two decided that they wanted to address an issue they experienced firsthand as consumers — the inconveniences encountered by barbershop customers.

In 2015, LaRon and Salvant launched Squire, a barbershop business management system that they hoped would bring the barbershop space into the digital age by making appointment scheduling and cashless payments more efficient. After acquiring a shop of their own in New York City to learn the ins and outs of the barber business, the two quickly recognized a need to provide a service for the barbers and small business owners in addition to their customers — an operating system that could help them attract and retain clients, manage their appointments, and streamline their business — and pivoted. Ten years later, the app serves 30,000 barbers globally and has a $750 million valuation.

“Ultimately, I think the best companies that are the most successful are driven by a desire to help people, to be of service, and to add value. Otherwise, why exist?” said LaRon. “That is the core of Squire, and I think those values are exemplified by the student body of the Law School.”

Wei Deng ’08 shared LaRon’s desire to start a business that would help people. After a stint in corporate law and investment banking followed by various tech jobs, she set out to start her own company that would create a new way to finance student loans. It was in the early days of pitching her company when she uncovered a pressing need among healthcare professionals — more flexibility in their work schedules and better compensation — and decided to pivot her business to meet those needs.

In 2016, Deng founded Clipboard Health, a nationwide online platform that connects medical professionals with career opportunities and health facilities with quality talent.

“I came to the realization that the nurses I was talking to were real people with real problems, and I should try to find them a productive solution rather than respond to a self-perceived problem,” said Deng.

Today, the company — which was last valued at $1.3 billion — is exploring how to expand into different markets.

Deng said her belief that anyone can become who they want to be simply by “doing” helped her in her entrepreneurial journey, and she encouraged Yale Law School students to adopt the same mindset while speaking at an event hosted by the Chae Initiative in March 2025.

“I would not be too wedded to what your identity is today; it’s not what defines you,” said Deng. “All the stuff you haven’t yet done — like being a CEO one day — you can just do that. You don’t need permission.”

Wei Deng ’08 talking at an event at the Law School — Wei Deng ’08 gives a talk at Yale Law School for the Leadership Program in March 2025.

The Art of Storytelling — and Advocacy

Once Leach concluded that a traditional law career was not for him and he began exploring other viable options, he decided to embrace what he does best: storytelling. Leach said his ability to create compelling arguments, a skill he honed at Law School, was at the core of everything he’d done throughout his life up until that point, and he realized he should use those skills in his new venture.

“I realized that I’m a storyteller, and all the skills I learned at Yale — absorbing a large amount of information, developing a point of view, and then communicating that in a persuasive way, either in writing or in person — are things I’m good at, and they are a huge part of succeeding as an entrepreneur,” said Leach, who noted that those skills were useful when pitching his business to clients, employees, and investors.

Park also attributed her success as an entrepreneur to the advocacy skills she learned while at Yale Law School, particularly through her work with the poverty and immigration clinics.

“Whether you’re advocating for an idea or a person, being able to present your case to the world in a compelling way is the core of entrepreneurship,” she said, specifying that those skills helped her when recruiting new employees, pitching to investors, and securing deals with landlords. “All of that work is advocacy.”

Ultimately, I think the best companies that are the most successful are driven by a desire to help people, to be of service, and to add value. Otherwise, why exist?”
—Songe LaRon ’10, Squire founder

The cohort of entrepreneurial alumni exemplify that a Yale Law School education is an all-purpose leadership degree and prove what is possible when students feel empowered to go forth in the world as leaders.

“I appreciated the breadth of opportunities that Yale Law School offered me in terms of public policy and business law classes. I also benefited from the tight-knit community that made it easier to creatively explore different interests, thanks to faculty support and student networking,” said Kommareddi.

Leach aims to encourage more students to become entrepreneurs. “There are a lot of misconceptions about why lawyers would make bad entrepreneurs, and they might be true of lawyers in general,” he said. “But at Yale Law School there’s a lot of creativity and unconventional thinking, and I think there are a lot of opportunities to be had for the people who are willing to take a chance on themselves.”

This intellectual mindset coupled with a nurturing academic environment has proven to be a powerful force for alumni who have pursued nontraditional paths after law school. Daniels credited Yale Law School for its faculty support and interdisciplinary course of study in shaping him into the business person he is today.

“At Yale Law School, there was enormous support for me pursuing my dreams beyond the law, which helped me in becoming a leader in society at large.”