Business & Finance, Quotable Magazine

Find Your Tribe with Jaclynn Brennan of Fylí

In 2021, only 2% of venture capital funding went to women-led startups in the United States. Jaclynn Brennan, CEO and co-founder of Fylí (pronounced Fee-Lee), a community catalyst and mastermind program for female founders, is on a mission to change that statistic.

Before Fylí 

Brennan worked in the fashion industry for 12 years before getting into entrepreneurship. During high school, she took classes at the Fashion Institute of Technology before graduating and attending the Art Institute of Fort Lauderdale. After starting her own fashion agency with a friend while in college and finishing her degree in only 2 and a half years, Brennan had tons of experience under her belt when she graduated, but she was extremely burnt out.

“I think it taught me a very, very valuable learning lesson as an entrepreneur — you have to take care of yourself and set healthy boundaries as you’re building and growing and scaling,” Brennan said. “So even though I graduated with the highest achievement overall and magna cum laude, I was mentally and physically burned out.”

After spending six months at home, Brennan got back on her feet and worked her way up in the New York City fashion scene, going from working unpaid internships to eventually co-designing Serena William’s first jewelry collection.

Living and Learning: The Start of Fylí

The idea for Fylí came about when Brennan was starting a tech company with three male co-founders. Brennan said this experience was difficult because she didn’t know the ins-and-outs of negotiation and investment.

“It was honestly a really tough time because I did not understand business like I do today. I didn’t negotiate my contract, my vesting schedules,” Brennan said. “…That experience led me to what I do now. That experience of feeling loss being the only woman in the room, feeling like I don’t want to ask questions because I don’t want to feel stupid led me to go to every female founders event I could in New York City to try to find my tribe.”

At a female founders event, Brennan met Summer Li, the other co-founder of Fylí. After analyzing different female founders communities, they decided they would make their own unique community.

“We saw a big gap in the market for early-stage diverse female founders,” Brennan said.

Embrace Your Superpower

Fylí, which stands for tribe in Greek and family in Latin, started off as an unofficial club within a coworking space but has since grown to have 10,000 members in their global network. Brennan described Fylí as a mastermind, which is a peer-to-peer mentorship group for like minded individuals.

Everyone who applies to join Fylí gets an interview. Brennan described the interview process as very interpersonal since she uses what she learns in the interview to sculpt perfect mastermind groups.

“We’re asking deep questions about your childhood and your life, how you grew up, how you handle making hard decisions, your ambitions, your skill sets, and your superpower, because I really believe that all of us have a superpower,” Brennan said. “And when you’re paired in these cohorts, a mastermind means everybody has a different superpower to contribute.”

Fylí never takes equity from their member’s businesses, Brennan said, and instead serves as a paid membership group where entrepreneurs support each other in these small, carefully crafted cohorts. Tribe members get access to education, resources, training, mentorship and funding opportunities. Membership is $8,000 for the year, which Brennan said is low compared to most mastermind groups with a minimum buy-in of $25,000. In the future, she plans on starting a fellowship program for those who can’t afford the membership fee.

Leveling the Playing Field 

Through their interview process, Brennan hopes to find all kinds of women who have the potential to achieve greatness, including women who didn’t necessarily go to a top university or have a traditional career path. By supporting all types of women with the necessary resources to be successful in a male-dominated industry, Fylí is creating a more equitable playing field for entrepreneurs one cohort at a time.

“My whole founding team is very diverse [and] nonwhite. And it’s so important to teach women that look like us, how to raise capital, how to think about money, how to create wealth, legacy and impact because we are becoming self-made.”

When reflecting on her experience navigating her career, Brennan emphasized how important it has been for her to embrace her identity. 

“I worked in fashion for 12 years and I was constantly told what I should be, how I should look, what I should wear, what I should say, and when you show up as your true authentic self … you shine, and nobody can take that away from you,” Brennan said.

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