DREW HERSHKOWITZ ‒ NYA MEMBER SPOTLIGHT
Drew Hershkowitz has been a member of NYA for the last three years while also balancing his role as Chief Information & Technology Officer for Casdin Capital. Drew is a technology professional with over 25 years of experience in the financial industry, working primarily with hedge funds and investment banks. While leading both large and small teams to deliver mission-critical technology platforms, Drew applies a practical and commercial mindset and takes a results-oriented approach.
How did you meet New York Angels, and why did you decide to join?
I joined New York Angels in 2021, and I actually wasn’t looking to become an angel investor at the time. I have always enjoyed helping companies and teams grow, but my experience had been from the inside, not as an investor. I heard about NYA through two different longtime friends who launched startups, and I became very interested when I learned about how NYA operates and the breadth and depth of experience of the group, combined with the quality of the companies they attract. I had some great early conversations with Michael Costa and a couple of other NYA members, and after sitting in some of the early Screenings as a guest, it was an easy decision to join.
What has been your most memorable experience as a New York Angel?
There isn’t one single experience; however, I do find co-leading deals very rewarding. When I reflect back on these experiences, it really allows you the opportunity to get to know the founders and really understand their business in depth. As a lead or co-lead, you help other prospective investors understand the most important points for decision making. More importantly, you are connecting with the founders on a human level, beyond just the product and the numbers, to build key relationships, and these relationships might very well outlast the investments.
What have you enjoyed most about being a New York Angel Member?
Since NYA members individually invest in each deal, I didn’t really expect the incredible willingness to collaborate within the group. There are people who have expertise, and they are willing to share their expertise and their time, even if they're not particularly interested in a company. I found that very surprising and welcoming. Working with NYA, I’ve been able to build relationships that will last for many years to come.
What do you look for when you are investing in a company?
When I am investing in a company, it is important that the founder can clearly describe: 1) the problem they're trying to solve; 2) how their product or solution is the answer to that problem; and 3) why we should believe that they're the ones who can solve that problem. They need to be passionate about what they're creating as well as able to articulate why this is a journey that’s worth it for investors to take with them. Then, of course, the economics and the scalability need to need to be worth investing in. Finally, NYA members go into a lot of detail in the diligence process, and in doing so, it is also important for me to understand the founder, how coachable, how adaptable they are.
What do founders like most about working with you?
With my background in technology, I tend to bring a different perspective than many other angel investors. I want to learn about their platform and their architecture decisions, and whether it may or may not need to change as the company scales. All of this really comes from a curiosity standpoint, not a critical one, because I'm looking to develop a true partnership. I really enjoy having a more wholesome technical conversation during the diligence process to really understand the platform, and so that often means with the team, not just the founder. There may be a separate technical lead or someone else on the team who can help articulate this. In a number of cases, those conversations have evolved to be collaborative longer-term, not just during the investment phase as the company grows.
What differentiates companies that you see at Screening versus those who make it through to Due Diligence?
Some of the companies we see may sound great, and the problems that they’re solving may really resonate, but when we go deeper into the diligence process, we might identify blind spots or areas of concern. Those alone are issues, but if the founders can talk through these concerns, either making us comfortable or giving us the impression that they can be coached and they’re adaptable, then those issues are more likely to be resolvable. During Screening, it's extremely important to be articulate, so being prepared is critical. The Screening process is often the first opportunity for many of the NYA members to meet the founders, so making a strong first impression is important.
What advice would you give founders who are starting to fundraise?
Growing a company is a long road. If the company is going to be successful, fundraising becomes a periodic exercise along the way. Acknowledging that upfront and doing your homework is incredibly important. You need to be prepared for some tough questions from some demanding investors and be responsive with follow-ups. Inevitably there are going to be a lot of questions thrown at the founders during the process, so it's important to be able to respond with thoughtful answers, even if it takes some time. Since this is a long-term relationship being formed with investors, it’s important to look at investors as partners who you want to grow with.
When you look at your past investments, what advice would you give founders to deliver a successful exit?
Candidly, I'm relatively new to NYA, and I have not seen an exit yet. However, founders who are open to advice and suggestions and those who seek input from investors form a far stronger bond, which will help maintain confidence from investors while working towards the exit.
What advice do you have for newer NYA members?
One of the best ways to get involved early is by co-leading a deal. It is an educational experience because you are partnered with somebody who has done this many times before, and it is extremely helpful. You are working with companies and founders for years to come, so the sooner you can invest your time with them, the sooner you can help make an impact.
How do you balance working full-time and angel investing with NYA?
It's hard. I certainly don't have the time that I would love to have to join all of the Forums and Screenings during the day. I review the deal pipeline off hours in Gust, and then I watch the recordings of the diligence and discovery sessions, which are incredibly valuable. I try to follow up on all the discussion threads of the ones that that really piqued my interest. I'm less available during the days than many other angels in the group, so I spend a lot of time off hours.
