Haley Bryant is a Principal at Hustle Fund and early stage angel investor.

Before making the pivot to full-time investing, she was the COO of Animalz, GM of Golden Wok and an early participant in Angel Squad where she helped build out our programming and community. 

We caught up with Haley to learn more about her Squad journey, diving into: 

1. The value of a truly diverse community in the investing space
2. Learning to invest by handling real Hustle Fund deal flows
3. Her unique path from operator to full-time investor

“I’ve found the best ways to learn are by doing, through research, and by working with the best practitioners. Angel Squad ticked all three of these boxes.” 

How to start angel investing as a full-time operator

Haley started her career in retail, working as an associate through Apple’s Store Leader program and quickly moving up the ranks until she became a senior manager. 

Her customer success roots led her to iDoneThis, which was later acquired by Xenon Partners, and Brazen before joining Animalz. 

As the director of customer ops and eventual COO, Haley spent the last four years scaling the content marketing agency before stepping into a GM role at Golden Wok, Animalz’ holding company.

She saw the most customer obsessed team members and customers consistently do well, informing her future investment framework.

Angel investing as a vehicle for societal change

It wasn’t until 2020, following the murder of George Floyd and a new era in the fight against systemic racism, that Haley was inspired to look beyond operating and pursue angel investing. 

She was motivated to invest in founders from and/or serving underrepresented backgrounds. To do so, she began writing checks and joining angel communities.

Her first angel check was into Sacra, the private markets research company. She joined to learn from their community of experienced investors and operators. As her confidence grew, so did her network.

While the checks Haley writes aren’t huge, she knows that change will happen through more people from all backgrounds having a seat at the table.

Working directly with the team at Hustle Fund

Haley first linked up with the Hustle Fund team through a mutual investment in Flow Club, a community for virtual co-working, with Elizabeth, one of Hustle Fund’s GPs and co-founders. 

She quickly realized Elizabeth was a “powerhouse of an operator” and a top-tier investor, so she started following her on Twitter. When Elizabeth posted about Angel Squad, Haley was quick to apply. 

Once onboard, Brian, Hustle Fund Venture Partner and Angel Squad GM, recognized Haley’s talent and leadership capacity. He extended an offer to get Haley more involved in building the Angel Squad experience for others. 

With Haley’s infectious energy and industry expertise, she was excited to jump into Angel Squad — and the Hustle Fund ecosystem as a whole. 

Ultimately, Haley chalks this up to “being in the right place at the right time.” 

“Hustle Fund is focused on developing people, with a progressive vision for the future of work in terms of collaboration and opportunities beyond their day jobs.” 

Finding a welcoming community through Angel Squad

As a Black person, a woman, and a single mother, Haley has dealt with exclusion and distancing in countless other communities. 

The energy and inclusivity of the Angel Squad network was refreshing and welcoming. 

Programs like Squad Pals, which connects members for one-on-ones based on mutual investment interests, exists entirely to nurture this proactive support and trust between participants.

With that trust, cohorts can: 

1. Share candid opinions and insights
2. Ask questions without fear of judgment or condescension
3. Learn about investing from both expert and peer experiences

For instance, when Haley joined Angel Squad, she led a program for early stage founders to meet Angel Squad members, enabling founders to meet angels and the community to discuss each opportunity collaboratively. 

As Haley describes it: “Every other week, people would come together and share opinions, which are based on working within a certain vertical, sector, or region — or with that target customer base.” 

A community of investors where diversity is essential

She also emphasizes that the Hustle Fund team does an outstanding job of choosing members who’ll be the right fit for the community throughout the application process. 

It’s especially impressive given that no two Angel Squad participants necessarily come from the same geographic areas, investing experience levels, industries, demographic backgrounds, etc. 

• Roughly 46% of Angel Squad participants are women
• About 32% come from careers outside of the tech industry
• Over 10% come from historically underrepresented communities

In Haley’s experience, this can be attributed to the fact that selection isn’t solely based on the application or the typical requirements that determine your value in a cutthroat investing space. 

Instead, it’s about having meaningful conversations with potential community members. 

Angel Squad has never been focused on titles, brands, or business-school pedigrees. What’s most important is, in Haley’s words, being a good person with good intentions. 

“Being a Black person, a woman, a single mother: I’ve been in situations where I’m not a community insider. The warm welcome from Angel Squad felt great!” 

Learning to angel invest by handling real deal flow

One of the main benefits of joining Angel Squad for Haley was being able to make more small, diversified investments. Squad members get direct access to curated Hustle Fund investments, meaning they get to assess startups alongside the pros — at a fraction of the typical buy-in. 

Before Angel Squad, her average investment was around 5 times greater than the $1,000–2,500 checks she cuts now. Participating in the syndicate has helped her reduce the risk through diversification. Learning from experienced investors has accelerated her development.

The opportunity to review a lot of raw pitch decks has been key to her learning, since reading syndicate pitches with a lot of “spin” can obscure the business fundamentals of the startup. 

“When you’re reviewing pitch decks on a weekly or daily basis, you have to get really comfortable with forming your own opinions on the underlying value of a business.”