Jai Jai Greenfield Co-owner, Harlem Vintage

I had a great job with Morgan Stanley and I was making great money, but it wasn’t personally gratifying for me. At the same time, I was seeing all these changes going on in Harlem, where my husband and I go to church and my grandparents had lived. Businesses and new people were starting to come into the neighborhood, and I realized that if there’s a market for a yoga studio and a bowling alley in Harlem, surely there’s a market for a high-end, full-scale, full-service wine store. And if I’m not going to do it, someone else is going to recognize the potential. All my education at Wharton and at Kellogg would have been for naught if I didn’t try.

So in February 2002, I decided to open Harlem Vintage with my partner, Eric Woods. I started to get into wine while entertaining clients for Morgan Stanley at restaurants with extensive wine lists. Lots of times I would be the only female or the only black person, and I wanted a way to contribute to the dinner discussions. These guys knew everything about trade and stocks, but they didn’t know a thing about wine. I figured this was my angle to deepen my relationship with the client. I’m going to know all I can about the wines that are served at these restaurants. I couldn’t do what I’m doing now if I didn’t have seven years at Morgan Stanley. I’m a big believer that everything happens for a reason. In many ways, I’m doing the same things running Harlem Vintage that I did before, in that I’m selling a product. The difference is the interaction with the customer. On Wall Street, there wasn’t the personal relationship with the client. They didn’t really care if they liked the stock, and they didn’t care if they liked the sales person. Here, there is much more of a personal relationship. The customer really holds you accountable and gives you feedback that helps make your product stronger.

Owning your own business takes stress to a whole new level. I’m constantly thinking about every aspect of the store, from the scuff on the floor to what’s the next step for Harlem Vintage, and I haven’t seen my husband in two weeks. There are some sacrifices, but ones that are worth being made. I am so much happier and more satisfied now. For any other woman trying to figure out what would satisfy them professionally, I would say do what you like. We are sometimes so restrictive in our career options because we just don’t know what is out there. You have to know yourself professionally and get good training— three years or more—on someone else’s dime first. Work for someone who can give you experience so when you want to open your own business, you can make that leap with confidence, having seen the big guys do it.