Angel Investing, Explained

Last week, I spoke with the team at Girl Math Capital, an alternative investing community for women that aims to democratize access to investing education and deal flow in the angel, real estate, and crypto ecosystems.

Here at All Things Fashion Tech, we talk a lot about the startups and founders changing the fashion landscape. Many of those companies rely on angel investors for at least a portion of their funding, which got me thinking: some of our readers may be curious about angel investing themselves, but unsure where to start or how to bridge the gap between interest and action.

That’s what made this conversation feel particularly timely. Girl Math Capital is focused not just on writing checks, but on helping women understand the mechanics, risks, and realities of early-stage investing, offering practical guidance for anyone who wants to move from observing the ecosystem to participating in it.

Hear more below from the founders, Emma Pratt, Porter Geer, and Serena Ainslie, about why they launched Girl Math Capital, and how you can break the barriers to investing.

Have you always been interested in angel investing, or was there a specific moment that sparked that interest?

• Emma: My interest in angel investing really emerged over time. I had interned at a growth equity firm, which sparked my interest in the startup ecosystem, and starting my career in banking gave me exposure to such a range of companies, which I really liked. When I joined Uber, while it was exciting and fun to be at such a rapidly growing company, I missed that breadth. That led me to start researching and tracking consumer brands on the side. Once I learned about SPVs and how they enabled investing at a much more approachable check size, the investing began!

• Serena: I’ve always been interested in entrepreneurship and have loved following early stage startups building products I believe in since college. However, my interest in angel investing stemmed from my mom, who has been in an angel syndicate since I was in high school. I was always interested in the opportunities she got to invest in early stage startups, but I assumed it was something I wouldn’t be able to access until I was much older and had significantly more disposable income. Dispelling that myth is a huge reason we wanted to start Girl Math Capital!

• Porter: I remember looking around at the successful individuals in the industry I worked in a few years ago, and almost all of them had “angel investor” listed on their profiles. From there I wanted to learn everything I could to understand why angel investing is a high-value signal and how I could get started as an angel investor myself. While I was able to source and invest in two deals on my own in that time, the difficulty I had in expanding my knowledge and experience was a key input for me in wanting to work with Serena and Emma to found Girl Math Capital.

What inspired you to start Girl Math Capital?

• All: We have been close friends since college, and in 2023, we each independently started exploring alternative investing for our own personal portfolios. The three of us realized we were running into the same challenges: unlike the men in our lives who were gaining access to deals through their informal networks, we didn’t feel like we had a consistent source of deal flow or a trusted place to learn, ask questions, and pressure-test our decisions. Girl Math Capital grew out of that gap - we wanted to create a space where women could learn from experienced investors and access deal flow in a community setting, investing alongside one another. We initially built it for ourselves and a small group of college friends, but it didn’t take long to realize how many other women were looking for exactly this kind of community.

Since launching your first cohort, what’s surprised you most about angel investing?

• Emma: I’ve been surprised by how many founders are intentionally choosing angel investors over traditional venture funding early on. They’re valuing flexibility, speed, and having mission-aligned investors around the table, which makes it an especially exciting time to get into angel investing.

• Serena: What’s surprised me most are the non-financial benefits of angel investing, which have ended up being way more valuable than I expected when we first started Girl Math. Angel investing often gives you direct access to founders early on and the chance to actually help shape a company by contributing your time, perspective, and expertise. Beyond that, the relationships you build through angel investing can open doors to future investment opportunities, jobs, and collaborations in ways that feel very organic.

• Porter: I’ve been surprised by how fun and meaningful a process it is for ourselves and our members. Finding amazing founders and companies to support is so exciting, and being able to provide both financial and non-financial support to help impactful organizations succeed feels more like a blessing than work.

What’s one piece of advice you’d give someone making their first angel investment?

• Emma: Start small and plan to write a few checks over your first year or so - it meaningfully increases your odds of backing an outlier.

• Serena: Invest with others! The whole process of angel investing, from sourcing to diligence to tracking once you invest, is much easier and more fun if you do it with others.

• Porter: Don’t overthink your first investment. It’s likely not going to be your home-run opportunity and that’s okay! There are things you don’t know that you’ll worry about, but the only way to get there is to learn by doing. Just write the check and get in the game.

For beginners, what does a realistic or responsible check size look like?

• All: It depends on your overall budget and financial portfolio, but under $10k is generally a safe place to start! For most of our members, their first checks typically fall in the $1-5k range.

What do you wish more women understood about investing, especially early on?

• Emma: Don’t be afraid to start early if you can. It might feel scarier when your savings are very much growing, but that’s also when time is on your side and the ability to take risks with money that can stay invested for 5-10 years. Additionally, building a portfolio of many small checks is often a smarter strategy than only writing a couple big checks! Early stage investing is risky, and increasing your shots on goal increases the likelihood of picking a winner.

If someone is curious but intimidated, what’s the easiest way to start angel investing today?

• Porter: Join communities like Girl Math and sign up for angel platforms like Play Money and AngelList to learn as much as possible and solve for the access to deal flow. Then, you can even improve your knowledge and investment process by putting together personal investment memos to practice evaluating companies, even if you don’t know the founder or have the cash to contribute. Then by the time the perfect opportunity rolls around, you’ll be well-prepared.

When evaluating early-stage companies, what signals matter most to you at this stage?

• Serena: We focus first and foremost on the founding team, followed closely by signs of product-market fit and early traction. That might look like revenue or user growth, but for pre-launch companies it can also include waitlist numbers, community engagement, or early media traction. We also look for clear differentiation from competitors and a large addressable market or demographic.

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