GLEN LEWY ‒ NYA MEMBER SPOTLIGHT

Glen Lewy began his career in corporate law, transitioned into investment banking, and then moved into venture capital.  Although Glen is “retired”, he remains active in finance by advising venture funds, sitting on boards, and investing as a New York Angel member.  Glen shares his experience working with Enertiv, initially passing on an investment that turned out to be his best investment ever, and his experience learning from two incredible mentors: Jim Wolfensohn and Paul Volcker.

How did you hear about New York Angels, and why did you decide to join?

I was a partner of a venture capital fund, and we had decided against raising another fund.  My partner was in his 70s, and I was in my 60s.  I was somewhat familiar with New York Angels through the early-stage venture world and had always been impressed. When I applied and saw the diversity of backgrounds among NYA members, I became even more impressed.  Gil Fuchsberg was my official sponsor, and I joined New York Angels in 2018.  

What has been your most memorable experience as a New York Angel?

While there’s not a specific experience that comes to mind, Enertiv is the company I have enjoyed working with most.  This was a very early investment for me, and I’ve since made several additional follow-on investments. It has been a rewarding experience to serve on its board and develop a strong working relationship with Connell McGill, Enertiv's CEO and founder.  The company provides software that helps building owners minimize their carbon footprint. It originally focused on office buildings and commercial real estate. As that sector struggled in the last few years, the team made an extraordinary pivot to industrial real estate.  This pivot has been very successful.  Working with Enertiv has been a fun learning experience, and hopefully by the end, it will be a lucrative one as well.

 

What do you look for when you are investing in a company?

I tend to be more skeptical than some of my angel compatriots, so I tend to look for reasons not to invest as opposed to reasons to invest. That being said, I have invested in 26 deals in about 7 years, which isn’t nothing. Overall, I look for three things when I invest:

1)        A market that is large enough;

2)        A product that I believe can be successful; and

3)        A management team that can execute and who would be fun to work with.

What do founders appreciate most about working with you?

You probably have to ask founders about why they like working with me, and I am not sure all of them do.  Overall, I suspect founders like that I am forthright and solution oriented. I try not to just provide observations or criticism, and I try to help them solve the problem.  As I tend to be very blunt, I do not indulge in “happy talk” well. If a board presentation or founder presentation does not hold together, I will tell them and help them identify how to improve.

 

What advice would you give founders starting to fundraise?

Fundraising is hard. Try to learn from every presentation and every response.  Founders can often learn from a “no” just as much as a “yes.” If an investor passed after serious consideration, don’t be afraid to ask questions. Ask what milestones you’d need to hit to be considered for future investment. My best investment ever was one I passed on initially.  I told the company that it was too early.  Six months later I did invest, and it turned out to be a great success with a 39x return.

What differentiates companies that you see at Screening versus those who make it through to Due Diligence?

I tend to make the cut earlier than most angels.  Usually I am skeptical early, and if I see something isn’t quite right in screening, I stop there.  I rarely go into diligence and then back out. 

In addition to the investment criteria I previously outlined, I continue through diligence with companies that have demonstrated traction with a completed product and some customer acquisition, rather than those that only have a business plan. As an investor, you can do all the diligence and all the research you want, but there’s no substitute for talking to the company’s customers.  One 20-minute call with a customer is worth hours of diligence. 

When you look at your past investments, what do you think is most critical for founders to be able to deliver a successful exit?

Focus. If a founder says they are solving three problems, I will pass on investing. There’s a reason “the plural of focus is unfocused.”  Particularly with early-stage companies, it’s important to pick one problem to solve well. You can always pivot if needed, but trying to do too much from the start rarely works.

 

What expertise do you bring to New York Angels?

I’m probably more valuable as a board member than as a new investor. I’ve been investing in tech for a long time, and I’m not a technologist, but I think I’m a pretty decent businessman. I have certainly seen a number of industries in my career, so I always shy away when I hear a founder say, “This industry is different.”  I try to draw parallels across industries and ask the hard questions.  I tend to be helpful to both founders  and other angels in asking why something will work in this industry if it hasn’t elsewhere.

 

What’s a little-known fact about you that has contributed to your success?

When I was a banker, I was a partner at James D. Wolfensohn Inc. where I had two unbelievable mentors: Jim Wolfensohn and Paul Volcker. They were partners, mentors, and friends, and I can’t summarize in a few words what I learned from them over the years. I think mentorship is incredibly valuable, and I’d encourage any founder or new investor to find experienced mentors who were once in your shoes and understand what you are going through. If they are willing to give you time, take whatever time and wisdom they are willing to give you.

Previous
Previous

NYA FOUNDER SPOTLIGHT ‒ GREG NEWBLOOM, MEMBRION FOUNDER & CEO

Next
Next

MARCH 2025 NEWSLETTER