Founder Lessons, Diversity & NYC Startups: Q&A with Ajay Chopra

What makes New York’s tech ecosystem so exciting? How has the journey from founding to IPO changed over recent years? New York Business Journal writer Anthony Noto wanted to know, so he asked Trinity Ventures General Partner Ajay Chopra these and other timely questions. The interview was a great opportunity for reflection: 2019 marks the 25th IPO anniversary of Pinnacle Systems, which Chopra co-founded in his living room and grew into a global, multibillion-dollar Emmy award-winning company traded on NASDAQ.

Since Noto’s piece is behind a paywall, we wanted to highlight some of the more enlightening snippets from their chat.

AN: This year marks the anniversary of Pinnacle’s IPO. What are your thoughts 25 years later?

AC: It was an incredible formative experience. I was 28 years old when I started the company; founding to IPO was a 7-year journey. I wish that kind of experience for all of our founders. I learned as much from the bad as I did from the good. Those experiences help me relate to entrepreneurs as we discuss their own journeys. Today, I’m as hungry and driven as I was when I was running Pinnacle. It’s thrilling to mentor and partner with the next generation of entrepreneurs who will hopefully be even more successful than I was.

AN: How does your experience as an entrepreneur influence your perspective?

AC: A lot of our Trinity partners have been founders and CEOs themselves. I’ve walked in those shoes. Since I’ve felt what our entrepreneurs might be feeling, I always make time to sit with them for a glass of wine or dinner, discuss where the shortfalls might be and give the right advice. Entrepreneurship is hard. It’s an emotional journey that you’re on for a very long period of time — longer than many marriages. As an investor, you have to build authentic, long-term relationships and, as difficulties come along, you have to deal with them without egos or one-upmanship. You strike a balance between governance and partnership.

AN: Studies show Silicon Valley has a below-average share of women-led businesses. Why do you think that is?

AC: I’m proud to say that half of my portfolio companies are female-led. That being said, I believe strongly that diversity needs to be addressed at every stage within the tech ecosystem. It’s important to have female investors, founders, executives, and board members. I have personally seen the greatest positive impact when startups have included female board members early on. With diverse perspectives included at the highest levels, one thing follows the other, and eventually the whole ecosystem starts to transform. We’re fortunate that Trinity’s investment team includes several talented women, including Trinity General Partner Patricia Nakache who has been at the firm for 20 years, making her one of the longest-tenured prominent female investors in Silicon Valley. Allison Baum also recently joined the firm as a principal. Our success as a firm is closely tied to the unique perspectives and skills each investor brings to the table.

AN: What’s exciting about New York’s startup ecosystem?

AC: New York is the center of the US from a trend-setting perspective. What happens in New York sets the tone for the rest of the country. A number of our portfolio companies are based there, including several in the areas of financial tech (or “fintech”) and real estate tech, given that New York is such a hub for both industries.

One of our fintech companies, Alice, automates pre-tax benefits, such as HSA (health spending accounts) and commuter benefits. Employees realize huge savings, and it’s also a very powerful retention tool for employers. It’s always fulfilling to invest in companies like Alice that do well by doing good.

Within Real Estate tech, VTS is a real estate management software startup that handles leasing and asset management on a single platform. On the residential real estate side, Nestio deals with residential multi-family marketing and management. Both of these portfolio companies are well-positioned and based in New York.

If you’re interested in reading more, check out the full article on the New York Business Journal website or see more articles featuring or written by Chopra here.