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Lev Ekster: Attorney Turned Entrepreneur

Lev graduated from New York Law School in May of 2009. He runs the super successful and very cool Cupcake Stop truck and is also an expert Twitter marketer. Quite a fast rise from law to business for a recent grad!

How did you start in the cupcake business?

When I graduated from law school, the economy was already poor heading for dismal, there were no full time positions. Many of my friends had their offers pushed back or rescinded. I was thinking of a back up plan. I had been to popular cupcake places downtown. There were lines out the door but, in my opinion, they were not really offering a great product. I researched the business. I found a baker on Craig's List, we did taste tests, tweaked recipes. I also then realized that a retail location was not feasible, was too expensive. I wanted to do the business, so I brainstormed with friends and family and came up with the truck idea. But, it was very hard to get a vending license. So, I turned to Craig's List again. I put an ad on there that I was seeking a mobile food vending license. What happened was that a pizza truck owner responded - he had a truck and license, but not a great business. We met over lunch and decided to form a partnership and transform the truck into a cupcake one. Here is where I needed some legal help. And I had a mentor who helped me, a former professor of mine. He helped form an LLC, write an operating agreement. His name is Jeffrey Haas and he is a contract and corporations professor.

Was this your first business?

No, actually, it wasn't. I had started a business in law school, a web site for law students, and Jeffrey helped me with that too. It was called This business is still growing.

How much do you work?

I work 28 hours a day, 9 days a week. That's what if feels like, seriously. It is key to have focus and follow through. That takes time. There are a lot of jobs - there is HR work, legal work, social media, kitchen management, event planning work, staffing the trucks, etc.

Advice to law students?

Stop crying about not liking the law. There is so much you can do with a JD outside of practicing law. And law is enormously useful. I have an attorney, but I can't call every time I have a legal question. My degree really didn't go to waste.

Use professors' office hours. There are so many professors in different fields who can be helpful.

How have you used a publicist?

When we started, we were NYC's First Mobile Gourmet Cupcake Shoppe. This was a good story and allowed us to compete with the big name places in New York . There was a special on us on PBS in January 2010 as well as write ups in the NY Times and so on. People emailed from Japan about plans to visit us! Apparently, more people take pictures of one of our trucks when it is on 5th and 23rd than the landmark Flatiron building.

How did you find the publicist?

Networking. A friend of mine who was in the nightclub business helped.

How do you use Twitter?

I have a dialogue with my customers - don't advertise to them: in fact, our conversations are often not about cupcakes. They may tell me about a new job or it could be about cupcakes - I tried this flavor, need less sugar, more sugar. It was awesome.

I was the keynote speaker at a Twitter conference on August 27, 2009 in NYC and recently spoke at the UN for World Entrepreneurship Day.

Where do you see yourself in 5 years?

Retired. Expand the business outside of the New York area, Atlanta , South Carolina . The beauty of being an entrepreneur is you don't know exactly where you will be. I do know where I won't be - doing a doc review in a poorly lit office. I would love to have ten trucks, or perhaps just stores, move into other food. I will take it one step at a time - don't want to expand too quickly, since then the quality of the product will drop.

What is your best advice for aspiring lawyer entrepreneurs?

Think through the business model. What I ended up doing was not exactly what I thought I would do when had the idea. Write a loose business plan since it will evolve. You have to figure out what to sell to whom and where.

Make sure you have time to devote to it. And, be willing to sleep very little - I don't think I get more than three or four hours of sleep a night since I have started the business. In NYC, people work hard.

Make sure you are adequately funded for what you want to do. Many businesses fail because they are under-capitalized. I will soon be bringing in an investor - actually my next door neighbor's son is an investor - so the first resource is always friends and family. Surround yourself with good people who will want to help.

Interview conducted by Inna Idelchik Swinton, Managing Director, Strategic Legal Solutions and Member of the Career Advancement and Management Committee, Spring 2010.