Just like the journey of any startup, sometimes the best decisions are made in the most uncertain times.
When the onset of the pandemic hit in early 2020, I decided it was time to make the most of it. In order to do so, I reset and up-leveled my career by going back to school at the University of Virginia, Darden School of Business.
The thought of an MBA had always been attractive: two years to invest in myself, rounding out my skills in areas such as economics, finance and the most daunting, accounting. Outside of the classroom, I welcomed the time and headspace to network with classmates and industry experts and deeply explore the next steps of my career.
I knew that I ultimately wanted to start my own venture or have another experience at an entrepreneurial organization. Before Darden, I spent five years at Google (arguably known for its innovative culture) and later jumped ship into the startup world, first at a pre-revenue AdTech startup as the first full-time hire and later at Profitwell, a fully bootstrapped startup in the Boston area.
I loved the chaos, creativity, and white space that each of the startup opportunities provided. I was pushed to be uncomfortable in the midst of ambiguity. There were a hundred ways to solve each problem, and I learned quickly that learning by failure was just as welcomed as finding the right answer.
At Darden, I started my job search early in the fall of 2020. With a focus on staying in the startup ecosystem in some capacity, I networked my way from one opportunity to another, talking to anyone from one-man shows to bounce around new business ideas, to giant investment firms with billions of invested dollars. To really dive into the ecosystem, I even started my own company with a revolutionary product called the Pocket Knock It, a piece of wood for your wallet that you can always knock on for good luck.
Around the time I realized that selling wood for your wallet would not be my life calling, I was introduced to Joe Raczka and immediately fell in love with the vision of York IE and the Dyn entrepreneurial story. Similar to my experiences, the York IE leadership team had both large tech and startup experience, understood B2B software like the back of their hand and were committed to making a difference in the New England startup ecosystem — all from my home state of New Hampshire. The fit seemed natural.
After over a year of getting to know Kyle York, Joe, Adam Coughlin and the rest of the York IE team through a part-time MBA internship, saying yes to coming onboard full time on the investment team was a no-brainer. Just like we evaluate investment opportunities every day at York IE, I’ve always picked jobs based on a number of core factors, the most important ones being the culture/team and growth opportunities. York IE easily checked both boxes.
First, from day one, I’ve seen how the culture of York IE is collaborative, down to earth and low ego. There is no task too tactical or small for anyone on the team, and it’s a roll-up-your-sleeves kind of mentality. This culture extends outside the York IE organization into our investor and startup network and seeps out into our investment portfolio and advisory services clients that we work with every day. Kyle, Joe, Adam and the rest of the team are all strong relationship builders and deeply care about the people they surround themselves with.
Second, as my first full-time investor role, I’m stoked to have the opportunity to dive into the deep end of our differentiated investment fund. Kyle, Joe and the rest of the team support our investment companies as past operators, not as prior bankers or investors. In addition, the evergreen model and lack of management fee for our investment partners only helps strengthen our differentiation in the ecosystem, really aligning our incentives with the entrepreneurs we work with. There is not vulture capitalism at work at York IE, just true partnerships to support like-minded founders on their growth journey.
Contrary to some perspectives, I actually believe that the macroeconomic headwinds have made this one of the best times to jump into an investor role and back into the startup ecosystem. While anyone can build a business and invest in the best of times, the hardest but most rewarding work begins when the tides change. With all that said, I’m thrilled to be starting full time at York IE.
Over the coming months I can’t wait to partner with the best startups in the New England ecosystem and beyond. If you are a founder or investor, I’d love to connect at mshapiro@york.ie.
