Samuel R. DeSimone Jr. says the first lessons he learned as a lawyer are worth following today: Take care of your clients and understand what their businesses do so you can add value.
Samuel R. DeSimone Jr. says the first lessons he learned as a lawyer are worth following today: Take care of your clients and understand what their businesses do so you can add value. (John Disney/Daily Report)

Samuel R. DeSimone Jr. is the executive vice president, general counsel of EarthLink Holdings Corp., a managed network services and communications provider.

In 2010-2013, EarthLink acquired 10 communications, IT and cloud services companies that serve business customers. and is now focused on designing, installing and managing secure network and IT solutions for multilocation businesses, primarily in the retail, commercial banking, healthcare and professional services sectors.

DeSimone served as the executive vice president, general counsel of MindSpring from 1998 to 2000 and has been the executive vice president, general counsel of EarthLink since 2000.

He was a corporate/securities attorney at Testa, Hurwitz & Thibeault in Boston from 1984 to 1990 and at Lane Powell Spears Lubersky in Portland, Ore., from 1990 to 1995. From 1995 to 1998, he was the vice president, corporate development and general counsel of Merix, a printed circuit board manufacturer in Forest Grove, Ore.

Describe your department and your role in it.

My legal/regulatory/public policy team consists of 26 employees, including eight attorneys who work primarily on business contracts, transactions and disputes, nine employees focused on compliance with telecommunications regulations, two public policy advocates and seven paralegals and contract managers.

My role is to set the overall strategy and tone to make sure my team provides outstanding service to our internal business clients, makes sure EarthLink complies with regulations and advances our public policy objectives.

Do you use outside counsel? If so, what firms and for what issues?

Our primary outside corporate/SEC counsel is Troutman Sanders and our primary outside litigation counsel is King & Spalding. We engage several outside firms for patent litigation, including Duane Morris, Kilpatrick Townsend and King & Spalding. Bingham is our primary outside CLEC (competitive local exchange carrier) regulatory counsel.

What keeps you up at night?

EarthLink is involved in several very competitive businesses and I’m always thinking about ways we can improve our business. With respect to my legal team, I try to anticipate legal issues that might be coming down the road or around the corner and legal resources that we might need in the future. But I have a terrific legal team and don’t lose any sleep worrying about it.

What question would you like to ask other general counsel?

What do you think you’ll be doing in 10 years? The answer to that question reveals a lot about a person’s aspirations and goals.

Is EarthLink experiencing the increasing number of patent lawsuits that other companies are experiencing?

Yes. EarthLink has experienced an increase in patent lawsuits filed by patent trolls.

Unfortunately, the U.S. Patent and Trademark Office granted patents to many “inventions” that did not deserve patent protection. Because defending patent litigation is so expensive, patent trolls acquire these patents and sue legitimate operating companies like EarthLink in an effort to extract settlement payments that are less expensive than defending the lawsuit.

What legal issues do you foresee becoming more important to EarthLink in the next five to 10 years?

The issues around data security and privacy are becoming increasingly important and will continue to be important for a long time. We will also continue to face significant public policy issues involving the monopolies and duopolies in the communications markets.

What is your approach to litigation?

EarthLink’s approach to litigation in which we are the defendant is to evaluate the merits from a standpoint that is as objective as possible. If the lawsuit is frivolous, we defend ourselves vigorously. If the lawsuit has some merit, we look for possible business solutions.

In situations where EarthLink is considering filing a lawsuit, my view is that litigation is generally a very inefficient and unpredictable way to resolve disputes. If people try hard enough and have good intentions, they can usually find a business solution to a dispute.

What advice would you give yourself when you were first starting your legal career?

When I began my career in Boston in 1984, Dick Testa, the head of the law firm, had one rule: no pink telephone slips on your desk at the end of the day. This was before email and voicemail and long before smartphones. Secretaries answered the phones if you were on another line and jotted client messages on little pink slips. The firm’s leader believed that his attorneys needed to be very responsive to clients.

Of course, with technological advances, everything has sped up over the last 30 years, but the core lesson still holds true: take care of your clients.

The second lesson I quickly learned is to immerse yourself in your client’s business. Whether you work in a law firm or in-house at a company, your client wants you to add value to his or her business and you can only do this if you understand what it is that they do.

I’ve learned a lot over the last 30 years, but I would share those two early lessons to lawyers starting their careers today.

What is the best way for a law firm (or lawyer) to introduce themselves to you for a possible business relationship? Do you accept cold calls?

I’m very satisfied with our current outside law firms and don’t have much time to meet with prospective law firms.

How do you divide your time?

I spend most of my work time in my role as an EarthLink executive working with the board of directors and executive team to make a wide variety of business decisions. Of course, I bring the legal perspective, but most of the decision-making involves the business. I enjoy working on business transactions and spend a significant amount of time on them. I help my legal team when they need help but try not to get in their way.

When our youngest daughter went off to college three years ago and my wife and I became “empty nesters,” I was expecting to have more free time. Can you tell me where that free time went?


Samuel R. DeSimone Jr.

Executive vice president, general counsel of EarthLink Holdings Corp.

Age: 54

Education: Amherst College, history, 1981; New York University School of Law, 1984

Hobbies: Soccer, mountain biking

Family: Wife, Liz, three daughters (two in medical school, one in college), black Lab

Civic: Global Village Project, a school for teenage refugee girls in Decatur, and the Turner Environmental Law Clinic at Emory University School of Law

Favorite fictional lawyer: I don’t have a favorite fictional lawyer but I enjoy Groucho and Chico Marx’s contracts scene in “A Night at the Opera