ALEXANDRA JENKINS ‒ NYA MEMBER SPOTLIGHT
Before Alexandra Jenkins became an angel investor, she spent almost 20 years in public equities, selecting stocks both on the long side and short side. Alexandra joined New York Angels in 2021, and her expertise in financial analysis has been an invaluable asset to the team ever since. Alexandra discusses the importance of investment terms for founders and why founders need enough capital to grow significantly.
How did you connect with New York Angels?
Initially, I found New York Angels through searching on Google for the best angel groups in the U.S. and in New York. When I looked into a few of them, New York Angels impressed me with the breadth of its investments and the caliber of its Members. NYA Members and portfolio companies are the best in angel investing.
What has been your most memorable experience as a New York Angel so far?
One of my first investments was in Fuego, a dance shoe company. When I first invested, I knew nothing about the world of dance studios or dance shoes. My experience with the company has been really eye-opening. The founder, Kevin, understands the market deeply, and he does a wonderful job educating investors. Kevin is an extraordinary entrepreneur. He is able to roll with new challenges, and he continues introducing new products. It's been a lot of fun to see the company grow.
What do you look for when you are investing in a company?
The first thing I consider is whether I want to learn more about a company or not. Initially, it’s not an analytical approach. Then I need to be able to easily understand what the business does and feel confident that the entrepreneur is the right person to run the company. Sometimes, I don’t invest because I can’t understand the business well enough or I feel the entrepreneur may be a subject matter expert but not strong on the financial side, for example. Their product also has to be something I want to watch grow over time.
What do founders appreciate most about working with you?
I hope founders would say they enjoy my curiosity about their business and my willingness to learn from them, because they’re the subject matter experts. Our best calls are when we ask the right questions, which enables a lot of listening and learning. It’s uncommon that I know much about their business, so I really enjoy learning from them.
What advice would you give founders starting to fundraise?
Founders don’t always appreciate how important some of the investment terms are. They might focus on valuation but overlook whether the round is common, priced, convertible, or a SAFE, and whether it’s pre-money or post-money. These details really matter to us. For example, information rights and follow-on rights are important to us. So, I would first advise founders to be really thoughtful about which investment product they are trying to raise.
What differentiates companies that you see at Screening versus those who make it through to Due Diligence?
To get to screening, a company has to have a theoretically viable business, an opportunity that’s big enough, a meaningful problem, and a reasonable way to solve it. But at screening, we also evaluate the entrepreneur themselves, especially during Q&A. Sometimes, they don’t know the answers or aren’t transparent, and that can really hurt their chances of moving forward.
When you look at your past investments, what do you think is most critical for founders to be able to deliver a successful exit?
Founders need to have a lot of capital. Some of our investments have been fine, but customer growth came in slowly or contracts ramped up gradually. If a company has enough liquidity, it works, but if they only have 90 or 180 days of liquidity, it can quickly become a crisis. Many founders are hesitant to dilute themselves and don’t want to raise as much capital as they should, but they would be better served long-term to raise enough is critical.
What expertise do you bring to New York Angels?
My background is in public company investing, so I am comfortable analyzing financial models and thinking through the numbers. I do not have the subject matter expertise that some of my fellow angels have, like in medical or consumer products, and I rely on them in diligence meetings. I am strong on looking through the financials and making sure they make sense.
What’s one little-known fact about you that has contributed to your career success?
In 2008, at a public hedge fund, we recapitalized a bank and lost money right away. One of the biggest problems was that no one, myself included, asked enough questions about the bank’s balance sheet. Every answer we got sounded intelligent, but none were clear or granular enough. And no one was willing to say, “I don’t understand, tell me more about what’s happening.” I figured others who were more senior knew more than I did if they were willing to invest, but that was not the case. That experience cost the fund, and importantly, it made me much more willing to ask questions until I truly understand something.
