Why Product Leaders Make Great Angel Investors

Welcome to Angel Investing Demystified - a newsletter that peels the curtain back on Angel Investing, Venture Capital, and Startups.

Each edition, you’ll get a 5-minute recap of one of our weekly virtual events held at Angel Squad. These sessions include anything from fireside chats to interactive deal reviews and workshops from the top investors + operators in the game. 

Before we get into this week’s post, I’ve got a big announcement to share…

In collaboration with Hustle Fund, Angel Squad is launching an Angel Investing 101 Bootcamp specifically tailored for Product Leaders. If you’re a Product Leader that has been wanting to use your experience to ramp up quickly as an angel investor, this is the perfect opportunity.

• What: 1-hour virtual event
• When: Tuesday, December 3rd from 10:00 AM - 11:00 AM (PT)
• How: Live educational content, including a Shark Tank-style pitch event
• Cost: Free

→ You can learn more and apply here. Spots are limited!

With that, let’s jump into Edition #5: Why Product Leaders Make Great Angel Investors

When product leaders venture into angel investing, they bring unique perspectives shaped by their expertise in building, scaling, and iterating on ideas.

Awhile ago, Eric Bahn (General Partner at Hustle Fund) hosted a fireside chat with three seasoned product leaders (and Angel Squad members) - Angela Santurbano , Jon Morgan , and Rawan Shawar . Each of them shared their journey into angel investing, the challenges, rewards, and strategies of backing early-stage startups, and how their backgrounds in Product have been a competitive edge in the investment world.

If you’re a product person considering angel investing, the insights were a can’t miss.

Why Angel Invest?

For these leaders, angel investing was less about financial returns and more about the experience of contributing to the entrepreneurial ecosystem.

Angela, who has experience as a Product Leader at Meta and Square, emphasized the intrinsic value of being part of a founder’s journey. “You don’t get to sit in board meetings or help shape decisions with public stocks,” she explained. “Angel investing allows you to actively support a founder’s vision while building meaningful relationships.”

Similarly, Jon, with a decade-long career at Google, found his way into angel investing through a passion for problem-solving. “I started by advising founders,” he said. “It wasn’t about the money initially. I loved helping solve problems and seeing others succeed.”

Rawan highlighted a broader mission: access. “The private equity world felt locked to outsiders,” she remarked. “When communities like Angel Squad opened doors, I saw an opportunity to participate in something previously inaccessible.”

The Product Managers Edge: Evaluating Founders and Markets

Product management is a role that demands cross-functional collaboration, user empathy, and a structured approach to problem-solving. These skills naturally translate into identifying and supporting promising startups.

As a former investment banker, Angela excels in analyzing market opportunities—a critical aspect of angel investing. “I look at markets both top-down and bottom-up,” she said. “What’s the broader trend? And how does the startup’s user base and revenue potential align with it?” She cautioned against relying heavily on financial models at the seed stage, as they often rest on untested assumptions.

Jon brought a sharp focus on user needs, a cornerstone of product management. “When assessing a startup, I look for founders who deeply understand their users,” he noted. “It’s easy to spot when they’re building for a real pain point versus chasing a trend.”

Rawan, with her expertise in payments and fintech, emphasized the importance of evaluating startups for long-term viability. “Not all disruptive technologies have staying power,” she explained. “I look for companies that balance innovation with a sustainable business model.”

Overcoming Bias as a New Investor

Implicit bias can skew decisions, particularly when investors rely on familiar tropes of what a “successful” founder looks like. Angela and Jon shared strategies for countering this.

“I intentionally reflect on my biases, especially when reviewing startups in industries I know well,” Angela said. “I ask myself: What’s changed since I was last immersed in this space? And what makes this founding team uniquely positioned to succeed?”

Jon avoids over-indexing on his domain expertise. “I start as a generalist,” he explained. “It’s important not to let past experiences blind you to new possibilities. Disruptors often come from outside the expected mold.”

For Rawan, building a diverse network is key. “Sharing ideas with people from varied backgrounds helps balance my perspective,” she said. “The Angel Squad community has been invaluable in offering fresh takes.”

Portfolio Support: A PM Superpower

Angel investing doesn’t stop at writing checks. The panelists highlighted the unique ways they support their portfolio companies using their product management skills.

• Hiring Guidance: Both Angela and Jon frequently help startups refine their hiring processes, particularly for technical and product roles. “Finding the right engineering talent is a huge challenge for early-stage startups,” Jon said.
• Product Feedback: Angela values founders who provide regular updates. “I love when founders share their progress,” she said. “It’s an opportunity to ask deeper questions and help them think through next steps.”
• Network Access: Rawan opens her professional network to founders, connecting them with potential customers, partners, or advisors. “It’s one of the simplest but most impactful ways to add value,” she noted.

Playing the Long Game

The panelists agreed that angel investing is about building long-term relationships, not just betting on short-term wins. Eric also emphasized: “You can treat life as a single-turn transaction or a multi-turn transaction. Supporting a founder through multiple iterations of their vision often yields the most meaningful outcomes.”

In the world of angel investing, product leaders bring a unique blend of analytical rigor, user-centric thinking, and a passion for building. By applying these skills, they not only identify high-potential startups but also become invaluable partners in their growth journey.

And…that’s it for edition #5 of Angel Investing Demystified! 

If you’re a Product Leader, don’t forget to apply for our Angel Investing 101 Bootcamp that’s coming up. You’ll get an on-ramp into how to use your product expertise for investing (through insights that take most investors years to uncover). Spots are filling up!

Disclaimer: All “Angel Investing Demystified” content is for informational purposes only, and should not be construed as legal, tax, investment, financial, or other advice.