How a law student got into venture capital


On a humid afternoon in Mānoa, Madonna Castro Perez, a third-year law student, was rushing to Fukuya, a traditional Japanese grocery store. She had insisted on bringing me lunch for our interview because, after all, sharing food is an integral part of her life.

In February 2021, Castro Perez became Vice Chairman of the UH student-run venture capital fund of which I am Chairman. Before that, she was part of a team that won the UH Venture Competition. She was a civil rights advocate at the Legal Aid Society of Hawaii, then an intern at Blue Startups, while attending law school. She’s breaking into the clubby, male-dominated world of venture capital — while maintaining a personal style that includes sharing lunch along the way.

Castro Perez grew up in Sinajana, the smallest of Guam’s 19 villages. She was surrounded by her Chamorro family: her neighbors were aunts and uncles, and her earliest memories were of crossing the street to play with her cousins.

A meal was often the highlight of those days. His parents grew local fruits and vegetables and some of his older relatives fished, trading the bounty with each other. Every weekend, her aunt would host a dinner party, where 20-30 people would gather to eat.

I wanted to be a philanthropist

Madonna Castro Perez

When Castro Perez was 11, she moved to northern California with her parents. his older siblings had already settled there for their careers. At that time, she wanted to be a philanthropist, inspired by the documentaries about starving children in Somalia that her mother forced her to watch.

“I was like, ‘Wow, that’s cool to just give money,'” she says. “But then I was like, ‘Oh wait, I don’t have any money.’ ”

After high school, Castro Perez realized she wanted to better understand Guam and its place in the world. She attended the University of California, San Diego, with a focus on international relations. She graduated in 2006 and then continued her studies at UH Mānoa, earning a master’s degree in Pacific Island studies. After that, for 10 years, she worked at the Legal Aid Society of Hawaii. In 2019, she enrolled in the Richardson School of Law at UH.

On one of his first days in law school, Castro Perez was late to class. Classmate Harley Broyles remembers walking into the classroom, rushing to find a seat, and blurting out Broyles’ name.

“She has a blunt personality,” Broyles says. “She comes out of nowhere and is loud, but I like that about her.”

They became best friends, leaning on each other to survive law school. “She’s always the person I can go to when I’m feeling down,” Broyles says.

Won a UH competition

The off-the-cuff conversations help guide Castro Perez’s path forward. At legal aid, she often exchanged ideas for food companies with her colleague Christilei Hessler. Eventually, Hessler introduced her to her brother, Peter Hessler, who ran a small coffee syrup business.

Castro Perez wanted to join him in the business. After meeting at an outdoor market at UH, she pushed Peter Hessler to enter the 2020 UH Venture Competition with her. Christilei Hessler also joined the team and the trio won $10,000 for the company .

This propelled Castro Perez to the forefront of the HU entrepreneurial ecosystem. Within months, she was named vice president of the student-run Calvin Shindo Student Venture Fund. However, she was new to venture capital, so to learn quickly, she spoke to executives of student-run funds at Cornell and UC San Diego, rented books, and enrolled in relevant courses. taught by faculty from UC Berkeley and UH.

During the summer of 2021, she completed an internship at Blue Startups, an accelerator based in downtown Honolulu. She screened the candidates and signed up for the apprenticeship program, which allowed her to work with startups in that year’s cohort.

Austin Yoshino, one of the founders she worked with, says that her “brain is very structured and operational thinking… Every week, I’m going to make her do things and make her put holes in her, and she’ll be like, ‘ And that ? “How about that? What about that?’ ”

Despite her rapid rise, Lada Rasochova, a professor at UC San Diego, reminded her that being a woman put her at a disadvantage. For example, investors repeatedly rejected Rasochova when she tried to raise capital for her startup because, the professor said, they didn’t perceive her as serious.

“I question that sometimes,” says Castro Perez. “Why aren’t many women involved in venture capital?”

Some progress has been made. There were fewer than 100 female angel investors in the United States until 2010, according to a reporting by Pitchbook. But over the past decade, the number of active female angels has increased tenfold, and the number of female sponsors in venture capital firms has increased by around 3.5% since 2019, the report said.

Interested in food technology and agricultural technology

Castro Perez hopes to work in venture capital law after passing the bar exam. She says she would like to join a firm, either in Hawaii or California, that specializes in venture capital law. At some point, she wants to start her own fund, focusing on food technology and agricultural technology.

On the day of our interview, she has a theoretical investment thesis for a company she named “Pepitas Capital.” It is full of food market statistics, but its overall investment philosophy is to reduce the cost of food production to make it more accessible to everyone.

She looks at her plate, then back to me. “Food is life,” she says.


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