From Apple Store Manager to VC Partner: How Haley Bryant is Demystifying Venture Capital for the Next Generation of Angel Investors

Haley Bryant's journey from journalism student to venture capital partner is a testament to how curiosity and determination can transform an opaque industry into an accessible opportunity for all.

A Family of Entrepreneurs Inspires a Bold Career Path

Growing up in a family of entrepreneurs, Haley Bryant was surrounded by business innovation from an early age. Her father's career at Bank of America and subsequent ventures in investment and consulting, combined with her mother's public policy consultancy and her sister's leadership in a 30,000-member chronic illness community, created a blueprint for betting on oneself.

From Apple Stores to Startup Success

After earning a degree in media studies and communications from the University of Virginia, Bryant joined Apple's retail division, where she quickly rose from associate to senior manager, leading stores generating millions in revenue. "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']," she recalls.

Her immersion in the startup world began when she launched Apple's small business program in the DMV region, supporting companies like WeddingWire, Cava, and Sweetgreen. This experience led her to roles at productivity and virtual event startups, both of which were eventually acquired, and later to scaling an agency from $2 million to $14 million in revenue.

The Accidental Angel Investor

In summer 2020, during the COVID-19 pandemic and social reckoning following George Floyd's murder, Bryant had what she calls a "come to Jesus moment." Inspired by an email from Animalz founder Walter Chen about building the world you want to see through startups, she made her first accidental angel investment in Sacra, a private market research company founded by a former coworker.

"It's almost like wanting to invest in AFROTECH™ and then getting to learn about so much in tech, business, [and] entrepreneurship," she explains. "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 since invested in 50 companies on her own, focusing on startups solving problems she experienced as a single mother, serving underserved markets, or overlooked by traditional venture capital. Her portfolio includes Scout, Rain, AngelList, and Dopl, which she describes as "democratizing access to health care by building for rural hospitals, specifically robotic ultrasound solutions."

Democratizing Venture Capital at Hustle Fund

Today, Bryant describes her investment thesis as "investing in great founders from anywhere who look like anyone." She has scaled this vision through her work at Hustle Fund, a venture capital firm investing in "hilariously-early pre-seed founders" primarily in B2B, fintech, and health tech.

"I did not go to school for finance. I did not know what venture capital was," Bryant admits. "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... It was totally just opaque to me."

Building the Angel Squad Community

Bryant joined Hustle Fund's Angel Squad community in summer 2021 as a paying member, formalizing her angel investor education. By fall, she became a venture partner helping build what is now a community of more than 2,500 members investing in Hustle Fund's over 650 portfolio companies.

The Angel Squad has done $25 million in deal volume across 89 deals and aims to onboard 10,000 angel investors. "That's why this mission of bringing the next 10,000 angels into the startup ecosystem is so resonant with me," Bryant emphasizes.

The Hustle Fund Venture Fellowship

Bryant ideated the Hustle Fund Venture Fellowship, a subset of the Angel Squad that brings together 50 global members who participate in Hustle Fund through the entire deal lifecycle. The fellowship, gearing up for its fifth cohort in January 2026, reviews over a thousand companies monthly.

"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," she explains. "So that's probably the work I'm the most excited about getting to do at Hustle Fund."

From Principal to Partner

Promoted to principal at Hustle Fund in 2022, Bryant has invested in 48 companies during her time at the firm. Her investment lens has sharpened to focus on what truly differentiates an idea, customer acquisition economics, and a founder's ability to sustain long-term work in their market.

Now stepping into the role of partner, she will manage limited partner communications, drive the Venture Fellowship forward, and raise funding. She has also recently joined BLCK VC as co-chair of its DMV Chapter, bringing her learnings about mentorship and apprenticeship to unlock the next generation of venture capitalists.

"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 expresses.