Haley Bryant is a Principal at Hustle Fund and early stage angel investor. To read Part 1 of her interview, click here.

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 from her insights as an operator-investor, diving into:

• Key opportunities to weave operator best practices into investing
• Three tips for accelerating your mental models as an investor
• How Angel Squad is designed to foster top-tier angels

“Through investing, I can optimize for learning as well as bet on myself. Reviewing decks is something I could do a thousand times over and be much happier in the end.” 

How your operator background informs your investing thesis

During her tenure at Animalz, Haley spent most of her time hands-on in the business: working with customers, hiring and supporting team members, and managing finances.

When she first began angel investing, she was particularly attentive to evaluating startups based on their founders. Now, her evaluation framework has evolved.

These days, Haley uses Hustle Fund's deal assessment framework to factor in the idea, the market, and the team’s execution. Something she learned to ask through Angel Squad:

“Is this startup in a very crowded, competitive space? Have other funds already invested in a similar idea, which will make it harder to raise later rounds downstream?” 

Coming from an operator background, Haley values numbers over narrative. While managing the Animalz P&L, she spent a lot of time thinking about and working towards aggressive customer retention and net margin goals, and appreciates both customer and bottom line focus on the founders she works with.

She acknowledges that it’s easy to feel FOMO when investing through hyped up syndicates and overlook gaps in business fundamentals. Angel Squad offers access to founders to be able to ask questions about gaps during live pitch events, and to hear how other people are thinking about businesses.

“Within a syndicate, founders receive feedback from dozens of people, so they figure out how to sell their story in a way that might obscure the fundamentals.” 

How Angel Squad is designed to create top-tier investors

As someone who has both participated in and helped build Angel Squad, Haley outlines three pillars of our community. 

1. Learning from peers & incredible investors

Angel Squad is a unique, double-sided environment for gaining investment knowledge. Members get to learn from peers and from experienced investors.

Through involvement in a community with members across sectors, career paths, and demographics, Squad members derive insights from each other’s experiences and expertises. 

No two members’ skill sets and knowledge are quite the same.

When someone posts in our online community about an investment opportunity or asks for recommended reading to learn more about an industry or investing topic, you’re likely to see answers from members across 8+ cohorts and a Hustle Fund investor as well.

2. Networking with good people—not just good investors

Haley attributes a lot of her growth across varied career paths to her network—looking for and connecting with mentors and the right people to follow. 

There are strong connections between Squad members themselves, as well as between Angel Squad members and the larger Hustle Fund investor network.

The community’s strength stems, in part, from participants simply wanting to bring their friends into the circle. These kinds of organic bonds enable trust and knowledge of character. 

As Haley describes it: “So much of Angel Squad is due to word-of-mouth growth. That drives the quality of the network.” 

3. Investing in Hustle Fund-approved startups and deal flow

Finally, the Hustle Fund team designed Angel Squad with the deeply held belief that no one can really learn about angel investing without actually handling deal flow. 

As such, Angel Squad allows members to assess and handle a real selection of Hustle Fund deal flow—at a lower buy-in than is usually expected of angels. 

Haley stresses that Angel Squad’s diverse community is bolstered by the fact that checks can start at $1,000, with participants encouraged to pursue a large, diverse array of investments. 

Traditional angel investing is expensive and very rarely turns into an actual profit, especially when you’re first starting out. Haley emphasizes that being able to diversify your portfolio in Angel Squad’s style is one of the best ways to save money as a new and learning investor. 

“Our bar for excellence isn’t about the university you went to. It’s about trying to make an impact that extends beyond yourself—potentially beyond your lifetime.”