CINDY COOK (NYA CHAIR) ‒ NYA MEMBER SPOTLIGHT
Cindy Cook joined NYA five years ago and has steadily increased her involvement in the organization. She launched NYA’s Member Engagement Committee to help further support new and existing members and served on the Marketing Committee for the past few years to grow NYA's presence nationally. Over the last five months, Cindy had joined the Screening Committee to enhance the application process. Cindy has also led a number of deals for NYA, and she acts a Board Observer on Allstar and Kidas. These experiences combined with her leadership on the NYA Board has led to Cindy becoming NYA’s fourth Chair. Prior to NYA, Cook had 30+ years of senior operating roles at industry leading firms in entertainment, healthcare, education and consumer package goods. She helped lead digital transformation and new product initiatives at these companies.
Why did you accept to become the New York Angels Chair?
When I joined New York Angels, I was incredibly impressed with the organization. Throughout my time here, I have worked to elevate the organization by listening to feedback from both Members and founders. I accepted the Chair position because I was already contributing to Member Engagement and in Marketing. In this role, I believe I can enhance these areas further.
I aim to get more members actively involved, building on the work I've done so far. As Chair, I feel I have more agency to impact the organization - in terms of marketing, encouraging participation, and boosting overall energy levels. I’m also an energetic sort of person, so I hope to motivate members, foster connections with founders, and attract more quality founders to the organization. By taking on this leadership role, I can amplify my efforts and focus on areas I hadn't been actively involved in but believe I can improve for the organization.
How do you see the future changing for women in early stage, investing in startups?
Statistically, it's harder for women to raise funding for startups, and I am very mindful of this. We are very open-minded and encourage female founders to apply to New York Angels for funding. As the first female head of New York Angels, I hope my position serves as a positive signal for women to apply. We will ensure that this and diversity overall is an important part of our communication strategy with founders. It's all the same idea, which is, you need a great idea, and you need to be a proven kind of leader that can bring something forward. I know there are many female founders out there who can achieve this, and I am committed to helping them through New York Angels.
Is there anything else that’s important to you as NYA Chair?
I just would say that I'm very excited to be leading the organization. I'm open to any inputs people have on how we can make New York Angels the best angel organization in the country. We don't have to just be ‘New York’Angels.
How did you meet New York Angels, and why did you decide to join?
After leaving my corporate career and completing several consulting projects, I had lunch with an old friend from a previous company. He told me, “If you're looking for something interesting that keeps you connected to the business world, then angel investing is an exciting area to be.” Initially, I wasn't sure if it was right for me, but after attending a Screening session, I was hooked. I was fascinated by the discussions – some things I was familiar with and many things I knew nothing about. I realized it was a tremendous opportunity to meet really interesting people from diverse business backgrounds, both members as well as founders. It was also an excellent way to learn about and hear new, cutting-edge ideas being launched.
What has been your most memorable experience as a New York Angel?
I’ve really enjoyed being involved with Allstar and truly becoming part of their group. I was a part of some major strategic decisions that needed to be made with Allstar, and I was called in early by the founders to talk through them. There were some thorny questions in terms of business strategy as well as personnel strategy. As a Board Observer, I’ve helped Kidas with their business as well.
It is incredible to support early-stage start-ups in their growth – this is what truly defines the experience for founders working with New York Angels. Anyone can give money to entrepreneurs, but New York Angels Members bring a wealth of expertise and a high level of commitment.
What have you enjoyed most about being a New York Angel Member?
Overall, I have appreciated working with New York Angels Members in terms of leading deals and the Member Engagement sessions. A lot of people who have attended those sessions say that they have been super valuable, and they have really enjoyed the contact with other angels, especially now that more of the sessions are in-person with a hybrid option.
The biggest differentiator for New York Angels is our Members. Our Members bring so much to the table due to their backgrounds as entrepreneurs, CEOs, venture capitalists, and business leaders who have founded, funded and built world-class companies. We commonly hear from founders and NYA Members alike that the advice, stories and friendships that are built through working together are where New York Angels goes above and beyond.
What do you look for when you are investing in a company?
As a long-time marketing professional, I assess whether they have a big idea. I evaluate the business proposition, the potential market size, and, of course, the founder. I look for a founder who is a winner—someone who will keep fighting, pivoting, and figuring out how to win. I also consider the potential for exit of significant size. I look at what kind of volume they need in terms of revenue or users, and make sure it's realistic. I look for founders who have real ambition, the necessary skills, and the background to achieve their goals.
What do founders like most about working with you?
People like that I'm a good listener, I take in opinions, and I'm thoughtful. I have a strong point of view, that I express in a non-confrontational way. People know I am very much about helping them figure out what to do. When it comes down to it, I give a clear, objective point of view, even if it's not what they want to hear – and they appreciate that. I've seen a lot of things across my business career, which enables me to root my answers in a lot of experience.
What differentiates companies that you see at Screening versus those who make it through to Due Diligence?
The companies at Screening generally have an excellent 10-minute pitch, which gets them in the door. During Diligence, we assess how capable the founder is and their depth of understanding of the business. We particularly evaluate whether the founder understands their financials. At Screening, we can't tell if someone else prepared the presentation for the founders. However, during Diligence, if founders can't explain their P&L, margins, and growth plans, it becomes clear where their capabilities lie. Diligence is essential for evaluating the founders based on their capabilities.
What advice would you give founders who are starting to fundraise?
I advise founders to be very buttoned up on their business and have a clear plan when meeting with investors. They should be confident, but not arrogant, and open to feedback. Founders should not be too malleable to input where it looks like they're zigzagging across the road based on that different input. Again, they should be clear. Ideally, founders should have some level of traction before approaching us and be mindful of their future funding needs. A realistic outlook is also important.
When you look at your past investments, what advice would you give founders to deliver a successful exit?
I have been investing about five years as a a New York Angel, so there has not been an exit in my portfolio. The things that are at a good point on the way to an exit are things that have significant month on month growth and have developed – if not pivoted their business somewhat. They have a clear idea of who their customer is and have been able to do an effective go to market plan. I feel that all systems need to be ‘go,’ and that there still needs to be attention given to where they're potentially going to exit. I'm still in a ‘wait and see’ mode because I haven't had anything that has gone to a successful exit.
I have been investing as a New York Angel for about five years, so I haven't had an exit in my portfolio yet. The companies that are on a promising path to an exit show significant month-on-month growth and have developed, if not pivoted their business somewhat. They have a clear understanding of their customer and have executed an effective go-to-market plan. I believe all systems need to be "go," and that there still needs to be attention given to where they're potentially going to exit. I'm still in a "wait and see" mode, as I haven't experienced a successful exit yet.
