Boston-born Haley Bryant is making venture capital (VC) more accessible as a partner at Hustle Fund. Her family background, with a father who started an investment and consulting firm, a mother who runs a public policy consulting firm, and a sister who is a leader in the support group Sick Sad Girlz Club for women with chronic illnesses, strongly influenced her interest in business.
Bryant became motivated to broaden access to VC after realizing she initially knew very little about the industry herself.
Although Bryant initially pursued journalism, graduating from the University of Virginia in 2010 with a degree in media studies and communications, her interest in technology soon took precedence.
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This led her to a career at Apple, starting in its retail stores as an associate. Within four years, she rapidly advanced to a senior manager role, overseeing stores that generated millions in revenue.
She told AfroTech: “I was really drawn in by people, passion, and this idea that we wore on our credo cards every day in the stores at Apple, [‘our soul is our people’]. It was a very people-first and then customer-first environment, which I was really inspired by. I loved tech, but I realized, after a few years of getting to advance through the stores and run a $60 million store, $100 million store, there was so much to learn there.”
Before joining Hustle Fund, Bryant had already established a strong foundation in the startup ecosystem. She launched Apple’s small business program in the DMV (District of Columbia, Maryland, and Virginia region), a role that involved supporting companies like WeddingWire, Cava, and Sweetgreen.
Driven by curiosity, she transitioned to a customer success manager role at a productivity startup, and later became a tech support implementation lead at a virtual event startup; both companies were subsequently acquired.
Her career then led her to the agency Animalz, where, over three years, she helped scale the company from $2 million to $14 million in revenue and grew the team from 20 to 150 employees.
During her rise from director of customer operations to chief operating officer, she gained valuable experience managing a profit-and-loss statement and leading distributed teams.
Bryant said she had a life-changing realization in the summer of 2020. This change was inspired by Animalz founder Walter Chen and happened while she was dealing with being a single mother, teaching her son at home during the pandemic, and witnessing the social unrest after George Floyd’s death.
“He wrote an email, something to the effect of ‘the world is not a fair place, but in a startup, you can build the world that you wanna see.’ That really inspired me, and it actually helped me form my thesis for angel investing,” she recounted. “It was around the same time that a coworker, Jan-Erik Asplund, decided to leave Animalz to found a company called Sacra, a private market research company. And I had worked with him for years and just saw his potential and asked if I could give him some money to support his new venture.
“So that was my first accidental angel investment,” she added. “It’s almost like wanting to invest in AfroTech and then getting to learn about so much in tech, business, [and] entrepreneurship. It was a very similar sort of investment, which gave me access to a community of investors and founders and helped me at least get started with my angel investing journey.”
Bryant has personally invested in 50 companies, prioritizing solutions for issues she faced as a single mother, supporting overlooked markets, and backing ventures ignored by traditional VCs. Her investments include Rain, AngelList, and Scout (previously Merit), with Dopl being a particular favorite.
“They’re democratizing access to health care by building for rural hospitals, specifically robotic ultrasound solutions,” she explained.
Bryant, a Partner at Hustle Fund, invests in diverse founders for the venture capital firm. Hustle Fund provides “hilariously-early pre-seed” funding, mainly for B2B, fintech, and health tech companies, and aims to expand wealth creation through capital, knowledge, and network access. Bryant joined the firm after connecting with General Partner Elizabeth Yin.
The mompreneur began formal angel investor training in summer 2021 as a paying member of Hustle Fund’s Angel Squad. By the fall, she was a venture partner helping develop the Angel Squad, which has since grown to over 2,500 members investing in Hustle Fund’s portfolio of more than 650 companies.
So far, Hustle Fund’s Angel Squad has closed 89 deals, accumulating $25 million in deal volume, according to Bryant. The program plans to significantly boost its influence moving forward by adding 10,000 new angel investors.
“I did not go to school for finance. I did not know what venture capital was,” Bryant explained. “When I worked at a venture-backed startup, I just knew that these guys with gray hair and Patagonias with briefcases came into a glass boardroom once a quarter, and we all freaked out and spent a ton of time putting decks together and presenting to them and sweating, but not really understanding what is venture capital. It was totally just opaque to me.”
She continued, “And even getting the opportunity to break into venture, I realized it’s opaque to so many people. And that’s why this mission of bringing the next 10,000 angels into the startup ecosystem is so resonant with me. And that’s what we’re on our way to do at Angel Squad.”
Haley Bryant started the Hustle Fund Venture Fellowship (also called the Angel Squad program). This program teaches 50 people worldwide about the entire process of making a deal. The next group (the fifth cohort) will begin in January 2026.
“We see over a thousand companies a month. So they are reviewing those deals, they’re flagging the deals that could be most interesting for us to spend more time on with a very diverse and global perspective … Our fellows are just members of our Angel community who want more experience, exposure, and are willing to do work, both to share their expertise with us and with founders and to help founders be more successful. So that’s probably the work I’m the most excited about getting to do at Hustle Fund,” she said.
In 2022, Bryant was promoted to principal at Hustle Fund, where she has since invested in 48 companies. Her increasing insight leads her to prioritize key differentiators: the unique value of an idea, the financial viability of customer acquisition, and a founder’s commitment to sustained, long-term effort in their respective market.
Bryant has been promoted to Partner at Hustle Fund, where her responsibilities will include managing communication with limited partners and continuing to advance the Venture Fellowship. She will also be involved in fundraising efforts.
Additionally, Bryant recently took on the role of co-chair for the DMV Chapter of BLCK VC.
“I’m really excited to see how I can take some of those learnings to now this role with BLCK VC as the co-chair of the DMV chapter around mentorship, learning, and this idea of apprenticeship to unlock the next generation of VCs,” she noted.
