Venture Capital Stories – Underscore VC

Hi, I’m Jimmy Orsillo. I’m a General Partner and the CFO of Underscore VC, an early-stage venture firm here in Boston. My role is to support the back office of Underscore, and then also get deeply involved with portfolio companies to help them build and grow.

Tell Us About Your Journey

My journey started as an operator. I started working as an FPNA professional over 25 years ago, and then gradually moved from early stage to later stage working at a large public company, American Tower, and then became CFO of two venture-backed companies. After I sold the second company where I was CFO, I joined Underscore VC in a dynamic role that was both back office supporting the fund, but then also helping all of our portfolio companies build and grow and realize their potential.

What Is The History of Underscore VC?

Underscore VC was founded in 2015 with the goal of breaking the black box of venture capital, providing a transparent model for companies to interact with a venture capital firm who could go beyond just capital. We have an ecosystem, a core community is what we call it, of over 1,800 folks that provide support and get directly involved with portfolio companies at the earliest stages. That’s where our focus is.

We invest in B2B enterprise software companies, and we leverage this community to provide support along the way. Everything from early stage support to later stage support as well.

What Inspires and Motivates You?

I’m inspired and motivated by waking up every day and thinking about how I could add value to not only my team at Underscore, but also to our portfolio companies. I always felt as an operator, I wanted a person to call when I had a question, that it could be any question that comes up when you’re building a company, and I wanted to be able to provide answers and support, and so I’m inspired and motivated to add value to people that seek it out.

What Attributes Lead To Success?

I would say there are two attributes that we see most commonly with the folks that have had the most success, and that’s vision and drive. Folks that have a right to an opinion on a market where they can create a very large company, and then the drive and motivation to go from the earliest stages to significant size over time. We enable that with not only our team, but also our ecosystem and core community.

What Are Your Must-Haves Before You Make An Investment?

The three must-haves for us to make an investment are a market opportunity that’s sufficiently large, thinking of a company that could generate hundreds of millions of dollars of revenue, backed by a founder who has the right to an opinion. And importantly for us is our ability to want to partner with that founder and know that we are aligned on what success looks like in the future.

What Advice Do You Have For Entrepreneurs?

The best advice that I have for entrepreneurs who are starting a company from scratch is to really think about how long the road is and the journey, and then to make sure that you’re up for the task. It takes 10 to 12 years in some cases, and there are a lot of bumps along the way. Be careful about who you have alongside of you in that journey. Make sure they’re folks that are going to work on your behalf and can provide you valuable support and advice along the way.

What Value Has Gesmer Updegrove Provided to Underscore VC?

Gesmer has been a great partner for Underscore VC. We love the fact that you have worked with companies that have done this before, that you understand what the venture ecosystem looks like. You wake up with the same mindset as we do, which is how to add value to companies and do so in a thoughtful and effective way.

Why Go With Gesmer?

Gesmer has the experience and the expertise to support companies all throughout their lifecycle. I see them everywhere. I see you at local events. We are in contact regularly on companies that could be emerging and breaking out, and you’ve done it before. I think you have the experience and expertise to be thoughtful partners at every step of the way, and that’s very impactful for founders that need that level of support.