If you're going to fish… fish in big ponds - why founders start companies in big markets

Many years ago, I visited Carmen Scarpa, a local Boston VC. Carmen grew up in my hometown of Andover and gave me advice from time to time on my career and startup. I highly respect his opinion. Very honest. Very direct. And very thoughtful. The kind of guy you want by your side.

I was deciding to leave my company I had cofounded because I was burnt out and, quite frankly, simply ready for the next chapter of my life. I wanted to go to a company with an experienced founding team. I wanted to work in Product and double down there. To be a part of an industry I would be more passionate about. And I wanted to be a part of a high-growth company.

And there was one important piece of advice Carmen said.

"If you're going to fish… fish in big ponds." 

Or in other words: Think big. Solve big. Go after big markets with a big base of customers.

I took that advice to heart and decided to go to Wayfair in 2013, to do my small part in transforming the way people shopped for furniture. In 2016, I decided to join Drizly, to take a leadership role leading Product and help transform the way people shop for alcohol. Both are big markets. Both are massive markets. And both opportunities have had tremendous success. It’s a piece of advice I pass on to other people I know starting companies today. And it’s a reminder to me to continue to do the same.

One year ago I decided to leave Drizly to start my new company: The Operators. And once again I’m going after a massive market at the intersection of representing, coaching, and managing the lives of tech executives, and providing larger, more efficient value exchange between Operators and companies. More to come.