BRIAN SILVER ‒ NYA MEMBER SPOTLIGHT
After starting his career in private equity real estate, Brian Silver moved into private investing for his family real estate company. Over the past two years, Brian become more involved in investments and fundraising, leading him to join NYA in March 2025. Brian shares the real estate long-term hold mindset is applicable to angel investing, how he found NYA through Google, and his experience being both a customer and investor in one of NYA’s portfolio companies: ProSentry.
How did you become an angel investor?
My career has been in commercial real estate. Out of college, I worked in private equity real estate, first at Time Equities in New York City, then at Partners Group, a global private equity firm, in their real estate division in Denver.
About three years ago, I moved back to Montclair to work for my family’s real estate company. We focus on adaptive reuse projects, redeveloping older, architecturally interesting buildings into boutique office space. We’ve also made private investments over the last 20 years. People frequently reached out to us about investments and private fundraising, so I wanted to learn more about venture capital and angel investing.
I took an online class at Columbia that covered venture capital and angel investing 101 to learn how deals were structured, the lingo, and technical terms. The professor had started her own angel group and said it was a great way to access deal flow and meet people in the ecosystem.
How did you find New York Angels, and why did you decide to join?
Surprisingly, I found New York Angels through Google. I searched for New York City angel groups, and New York Angels kept coming up. It looked like a great group of people with strong deal flow and interesting investments across a broad range of industries. They had deals in not just healthcare or tech, but also CPG, healthcare, real estate, and everything else. I applied online, attended a couple of meetings, met with members, and was admitted as a member.
What has been your most memorable experience as a New York Angel?
One of the companies New York Angels and I invested in is ProSentry. They build detectors for real estate, with a focus on water and leak detection. They offer wireless sensors placed in buildings that detect water and send alerts via text, email, or call. They also have gas detectors and water valve shutoffs. Water can cause significant damage quickly and is harder to detect than something like fire.
While I was evaluating the company as an investor, my building became a customer at the same time. As a customer, we learned about their operations and experienced their sales process and installation. Being able to dual track both as an investor and as a customer has made ProSentry my most memorable experience so far.
What do you look for when you’re investing in a company?
Talent: the founders and co-founders. Investors are looking for a unicorn: someone with deep technical expertise but also well-versed in finance, HR, and sales. They do not need to be experts in everything, but they need enough knowledge to drive the business forward. Adaptability and coachability are also very important.
Revenue model: investors love recurring revenue. Tech software is well-known for subscription and recurring revenue models that don’t have to start selling from scratch every day.
Exit potential: angel investors are in the exit business. That is where we make our money. So we look at market size and how the business is positioned for a potential exit.
What do founders like most about working with you?
I really like people. Angel investing is a people business. I enjoy connecting people and using my network to help founders with their pain points. I’m not afraid to help with business development or make introductions.
I have also worked in large organizations and now a small one, so I have seen both sides, the structure of big companies and the reality of wearing many hats in smaller businesses.
And finally, patience. Angel investing is a long game. It is not something that trades daily. It can take 7 to 10 years. We are not looking for quick flips. We understand building a sustainable business takes time, and we want founders to know we are aligned with that.
What is the biggest difference between companies you see at screening and those that make it through to due diligence?
First, a lot of founders spend too much time describing the problem and not enough time explaining the solution. Investors often hear a great story, but it is unclear how the product actually solves the problem. The companies that move forward clearly explain their solution and why it works.
Second, founders who do not assume everyone is an expert in their field. The best ones can take something technical and explain it in simple terms so everyone in the room understands the problem and the value of their solution.
What advice would you give founders who are starting to fundraise?
The best founders are very responsive. Even if it is just acknowledging an email within 24 hours, that signals urgency and professionalism.
Great founders also have an open mind. Some founders can be dismissive if you are not a big-name firm like Sequoia or Andreessen. You never know where a conversation can lead, especially with New York Angels Members. A 15-minute conversation can open a lot of doors.
What advice would you give angel investors who are interested in joining New York Angels?
Come to a meeting, or a couple meetings. Everyone is very friendly and open. People are willing to share advice and how they think about investing. There is a wide range of backgrounds and expertise in the room, and it is incredibly valuable to hear from different perspectives.
Also, the meetings are very well run. New York Angels is a well-oiled machine. Seeing how NYA operates and the variety of deals firsthand is the best way to understand the value.
When you look at your past investments, what is most critical for founders to deliver a successful exit?
I am newer to angel investing, so I have not gone through an exit yet in my two years. But I think founders who underpromise and overdeliver are key to exiting. They also need to manage expectations by making sure the board, investors, and stakeholders are aligned with what actually gets delivered.
What is something about you that has been especially helpful in your career?
Real estate is not an asset class that trades very frequently, so I am used to working with longer-term hold periods. That mindset translates well to angel investing, where you are looking at a 7- to 10-year horizon. While underwriting is very different, thinking about how a business holds up over time is very similar.
What motivates you?
Three things motivate me:
First, people and connection. I enjoy talking to people from different backgrounds, whether they are doctors, engineers, or CPG professionals, and connecting them.
Second, intellectual curiosity. You never know what deal is going to come through the door at New York Angels. Being able to dive into new industries and understand them quickly is very motivating.
Third, businesses that combine a strong idea with a mission. Healthcare and climate tech are great examples. Companies that can make the world a better place while building a strong business really excite me.
