1Mby1M Virtual Accelerator Investor Forum: With Steve Eskenazi, Angel Investor (Part 1)

Steve Eskenazi is an Angel Investor, and we had a number of interesting trend conversations.

Sramana Mitra: Let’s start with a little bit of your background. Tell us about what path you have traveled.

Steve Eskenazi: My career has three distinct phases. In the 1990s, I was Wall Street’s digital media analyst introducing Wall Street to companies like America Online and Electronic Arts. For the next 10 years, I was a venture capitalist for a firm called Walden VC where we invested in internet, SaaS, and digital media companies.

Our most well-known investment in the first round was in Pandora – the music service. Then my wife and I found ourselves in an interesting position in the late 2000s. We had three kids in 18 months. I decided to take a different path. I decided to unwind from my venture capital firm and become an angel investor and focused on my home-based startup – the three kids.

For the next dozen years, I’ve been spending my time – a third with my family, a third on my own portfolio as an angel investor, and a third in terms of giving back and mentoring. That’s a bit of a background.

Sramana Mitra: Talk about what you like to invest in. Did you formulate an investment thesis for your angel investment practice? How did you decide on which direction to go?

Steve Eskenazi: I invest as an angel in two broad categories – technology and life sciences. There are some investments in the intersection. My bias is towards companies I can help. I’m rarely a passive investor. My bias is towards working with other groups and teams. I’ve been a member of J-Angels, TiE, and a group called SV Squad.

I like to invest in things I feel passionate about. I’m not going to invest in the next startup that brings something to your door at 1 AM that you’ve been hungering for. I like to be contrarian. I like to invest in new and interesting spaces. I think what sets investments apart from where I was a VC is your fiduciary responsibility. If there are relationships that can be built and if I can help with my network, that’s what I really like to do.

I help entrepreneurs not avoid mistakes but to catch them early and figure out a methodology for dealing with the issues that young companies face in product-market fit.

Sramana Mitra: In terms of writing checks, do you invest pre-product-market fit or post?

Steve Eskenazi: Both. My check sizes range from $25,000 to a million dollars. I rarely invest alone. I like to bring in my friends and other colleagues. The more value-add help, the better.

Sramana Mitra: When you’re writing a $25,000 check size, what is the typical round including your friend?

Steve Eskenazi: I can give an example of a company we just invested in. It’s called Resonato. It’s based in Chicago. My group put in $450,000. The other lead put in $450,000. It was a little over $2 million round.

This segment is part 1 in the series : 1Mby1M Virtual Accelerator Investor Forum: With Steve Eskenazi, Angel Investor
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