The Path To Angel Investing And The Genesis Of The WIE Suite Angels With Rochelle Stewart
September 22, 2023
Rochelle Stewart is Vice President, Consumer Tech at Silicon Valley Bank and Founder of The Syndicate, an angel investing community for Black women. She previously worked in digital strategy at Conde Nast.

A first-generation college graduate, her interest in investing was initially inspired by 'The Intelligent Investor ' by Benjamin Graham, a book on value investing she picked up while a college student. Rochelle spearheads The WIE Suite's internal angel investing group, the WIE Suite Angels.

What was your personal path to angel investing?

While at Conde Nast, I recall reading an article Vanity Fair published about the 34 black women who were the first to raise over $1MM in VC funding. Around the same time, the first Project Diane report was released highlighting the lack of VC funding for Black and Latinx founders. This was a huge turning point for me. It triggered my "investor" curiosity. I went into overdrive researching the statistics on the funding gap, learning more about angel and VC funding, researching various angel networks like Pipeline Angels and new female-founded funds like F3 that were attempting to solve this really big problem. I realized how passionate I was about making a difference in this area - not only because of the funding gap but also because of the wealth gap, especially for black women. My thinking: if we (Black women) can start writing checks and thinking differently about taking risks and investing, there is so much opportunity and economic value that can be unlocked for our families and our communities.

I told anyone who would listen that I wanted to go into angel investing and eventually build a community that would aim to diversify cap tables. I wrote my first check, joined a few angel groups, amplified my networking efforts and started building the vision for what I wanted my investment community to be - the mission, member engagement model, investment approach, legal structure, etc. Ever since I read that article (I think it was published in 2016), I have been on a true mission to help more women become angel investors. Last year, I launched The Syndicate, an angel investment community and syndicate for black female angels. I've since joined and contributed to a number of female-focused angel investing groups including leading the WIE Suite Angels.

What was your first deal? The first check I wrote as an angel investor was in IFundWomen founded by Karen Cahn, also a WIE Suite member.

If we (Black women) can start writing checks and thinking differently about taking risks and investing, there is so much opportunity and economic value that can be unlocked for our families and our communities.

What have you learned over your investing career and how do you see investing now? Honestly, investing feels less like a career and more like a passion that I am fortunate enough to have the resources, the time and energy to pursue. Over the past 5 or so years, I've invested a lot of time into building relationships with investors and founders. Even now I still feel like I've only scratched the surface! This is still the very early phase of my investing journey.

What's stayed the same? I believe investing, specifically angel investing, is so much more fun as a team sport. I love collaborating. I love bringing others to the table as co-investors. I still enjoy the context switching and learning about new categories and industries as an angel and talking shop about different companies and industries with other investors.

What's changed about your approach? I'd say I have become more disciplined in my investing approach. I didn't write an investment memo when I invested in IFundWomen. I have since written a memo for every check. I know some angels invest in friends/people they know and they write the check without doing any diligence. I'm not in a position to do that at scale. I go as deep as I can without being too overbearing. I get excited about diving into the unit economics and customer retention curves. Given my traditional finance background, I've had to learn to let go of the numbers and instead lean in on 'investment conviction'. The numbers themselves are less important than how the they complement the founder's vision and the growth narrative. The market analysis is less important than my own personal investment thesis and reason(s) to believe.

How did The WIE Suite Angels come about? How did you get involved? The idea for the WIE Suite Angels was the result of two intersecting moments. First, as a member of many angel communities I'd built an informed perspective on the business model and operating model of different communities--what was out there and what was perhaps missing. Second, building the WIE Suite Angel community was a natural extension of the work I was already doing with my own angel investing community, The Syndicate. I pitched to WIE Suite founder Dee Poku (perhaps over a quick text!). I knew it was important to focus on active angel investors who could exchange deal flow and invest, and in the spirt of "WIE Women Who Do" that we'd want to measure the impact by the number of WIE Angels writing checks.

What is the group doing now? We come together for a monthly deal flow meeting where members are asked to share at least one deal currently in diligence or where they’ve already invested. This often leads to related discussion about macro trends in the category and is designed to facilitate opportunities to co-diligence and co-invest. After each meeting, I work behind the scenes to connect the dots between the deal leads and interested investors.

We also held our first WIE Suite Pitch Forum where WIE members who were currently fundraising could pitch to the WIE Suite Angels. We had four companies and one venture fund pitch. To date, all meetings have been limited to WIE Suite members. After three deal flow meetings and one pitch forum - we have collectively shared multiple deals and invested over $200K. I would love to see us invest at least $500K by the end of the year.

While we aren’t exclusively investing in female-founded companies - all investments to date have been female-founded. There’s also an affinity towards consumer, wellness, digital health, family tech, fem tech. A few investments amongst WIE Suite Angels include: Golde, Kroma, Superfoods, thirteen lune, and Dipsea.

What do you see as the future of the WIE Suite Angels? I see this as a thriving community of women who continue to "do" by investing, but also by mentoring, advising and building each other up as founders, investors, LPs, GPs. I could also see the focus expanding beyond venture/angel to include other alternative asset classes and finances/wealth management in general. Women investing and building wealth is something I am super passionate about and I'd love to do more of it with the WIE Angels community.

For other angel investors, what are some key tips to getting involved, making wise investments, and even knowing when something isn't going to work?

  • Not sure where to start? Check out Republic , the equity crowdfunding site and AngelList. They are two of the best resources for content, deal flow and more.

  • Use Twitter. Even if you don't post, follow angels, VCs, founders. I've met founders, sourced deals, learned from other investors, met co-investors, all through a Tweet or DM! I often stalk Clubhouse just to find new people to follow on Twitter. I have about five or six people on "alerts" to see all of their tweets.

  • I can also share a bit about my conviction scorecard, which I am currently in the process of refining. It consists of four areas: team, product, market, traction - all with sub-scores within each area. I then subtract points for risk factors and add points for fit within my investment thesis.

  • Learn venture math. I'm talking the fun stuff like dilution, valuation, cap tables, warrants and more. Yes it is an investment of time (and brain power!) but I personally think it's worthwhile to understand the fine print when investing in such a high-risk, illiquid asset.



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