York IE Profile

What is your role or function within the startup ecosystem?

“I engage with thousands of founders per month in my role running York IE, actively advising and investing in over 100 active startups, both through York IE and as an angel investor, and am a board member of several York IE portfolio companies.”

How did you start working within the startup ecosystem?

“When it comes to startups, I’m a true believer. I grew up in a family business in New Hampshire, and my parents did everything they could to drive home the importance of work ethic, integrity and community. After graduating from Bentley University, I started my career at WhippleHill, an EdTech SaaS startup that was acquired by Blackbaud. I then worked in successive executive growth roles at internet infrastructure startup Dyn, which Oracle acquired in 2016. From the time I could afford to begin investing, I began investing in the startup community, with both capital and sweat equity.”

What sectors are of interest to you and your company? 

“We invest in B2B SaaS companies up and down the stack, in tech laggard markets that are ripe for disruption, with founders who have strong industry experience and are looking for strategic growth help.”

Are you an entrepreneur or have you been one? If so, please tell us about your entrepreneurial journey.

“In 2019, Joe Raczka, Adam Coughlin and I co-founded York IE, which in many ways was the culmination of the career experiences I had over the previous 20 years. As my days at Oracle began to wind down, I decided to stop doing angel investing and startup advising for 1% of the time and instead formalize my passions into not just a day job but a full company. I thought there could be a new type of investment firm, one that broadens the definition of an investment beyond money to include time, resources and expertise. Entrepreneurs have always worn many hats, and I felt like it was time for an investment firm to do the same thing. Today, York IE has over 60 employees, dozens of advisory services clients and 36 portfolio companies, plus offices in Manchester, N.H., Boston, Portland, Maine and Ahmedabad, India.”

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What is a common roadblock you see startup founders face?

“So many new companies or new product lines are driven by brilliant technologists or industry savants who have an idea, talk to a few lighthouse customers and run with it. This is a necessary component of company building, but it is a product-out approach that oftentimes ignores the broader playing field. That’s why we preach a market-in approach — understanding your competitive and comparative landscapes and using those findings to differentiate everything about your company, from your product to your GTM to your marketing.”

What is your #1 piece of advice for aspiring startup founders?

“Play the long game!”

Anything else you would like us to know about yourself or your work prior to the interview?

“Family has always been at the heart of everything I do. My brothers and I have taken the portfolio approach to business that we grew up with; in addition to York IE, we also have York Creative Collective, YORK Athletics and York Real Estate. And my wife Katie and I established the York Family Foundation for our philanthropic and charitable efforts, focused primarily on supporting kids.”