How a Lawyer Transitions from BigLaw to the Halls of MSG, the Rings of the Olympics, and the Slopes of Aspen


How did a kid from New York become the top lawyer for a group of Colorado ski resorts? Follow Rana Dershowitz, now General Counsel and Vice President of Aspen Skiing Company, through a series of legal dream jobs with BigLaw and an elite boutique, Madison Square Garden, and the U.S. Olympic Committee.

How I Got My Legal Dream Job™ is a series of interviews with lawyers about their careers.

Shauna C. Bryce’s interview with Rana Dershowitz, Esq., General Counsel and Vice President of Aspen Skiing Company. With supplemental interviews and career advice from Heather Fine, Esq. of Major, Lindsey & Africa; Lan N. Nguyen, Esq. of Chadick Ellig; and Jared Redick of The Redick Group.

Check out the whole series >

Table of Contents

In 1946, a Chicago industrialist created a wonderland in the middle of nowhere. Walter Paepcke’s idea was simple—combine spectacular natural beauty with recreation and learning to create a space where harried visitors could be renewed in mind, body, and spirit. He chose an obscure town west of Denver. Today, Aspen is an international destination for skiing and other outdoor activities, a top luxury destination for the rich and famous, and an intellectual and cultural center. Paepcke was key in its development. He founded the Aspen Institute (an international think tank on values-based leadership with revenues in the $100 million range), the Aspen Music Festival and School (one of the nation’s top classical music festivals and the school of more than 600 international music students), and the International Design Conference in Aspen (now the Aspen Design Summit, a partnership with AIGA).

Rana Dershowitz, Esq., General Counsel and Vice President of Aspen Skiing Company

Rana Dershowitz, Esq., General Counsel and Vice President of Aspen Skiing Company

He also founded Aspen Skiing Company (Skico).

Skico is now a privately held company operating four resorts—Snowmass, Aspen Mountain, Aspen Highlands, and Buttermilk—as well as the award-winning Ski & Snowboarding Schools of Aspen Snowmass, two hotels (they’re building a third and planning a fourth), restaurants, and multiple retail facilities. There’s a lot more to these resorts than just winter sports. They operate year-round to accommodate hiking, running, mountain biking, skateboarding, climbing, camping, and other outdoor activities. And, of course, there are concerts and other major events.

That’s a lot for Rana Dershowitz, General Counsel and Vice President of Aspen Skiing Company, to handle!

Journey into Sports Law

How did a kid from New York become the top lawyer for a group of Colorado ski resorts?

One of the first things you should know about Rana Dershowitz is that she is super smart. But you’ll also notice she’s the epitome of oft-cited phrase “work hard, play hard,” and manages to balance competitiveness, a spirit of adventure, and plain old niceness. All of this led to a series of legal dream jobs.

Rana graduated from Harvard College cum laude in 1992, the recipient of Phi Beta Kappa honors and numerous other academic and merit awards. She was a Harvard College Scholar and a John Harvard Scholar, honors reserved for the top 10% and top 5% (respectively) of each sophomore, junior, and senior class.

But don’t think Rana spent all her time in the classroom. She was also a member of the Harvard Varsity Ski Team. All four years. For three of those years, she was captain. (If you ever doubt Rana’s long-term commitment to skiing, take a look at her knees.) Oh yeah, she participated in other sports and did collegiate sports radio as well.

Although she comes from a family of litigators, Rana didn’t initially want to go to law school. She wanted to choose her own path. But while in college, she was converted after falling in love with a constitutional law class. She assumed she’d eventually land in a policy and advocacy group. “It never crossed my mind that I’d do anything business-oriented,” she told me. “My initial expectation was that I would do constitutional law or criminal law.” At Harvard Law School, where we were students together, Rana was the executive editor of the Harvard Civil Rights-Civil Liberties Law Review and also served on the Harvard Journal on Legislation. She continued to be active in skiing and other sports. She graduated cum laude from HLS in 1995.

Law school taught me to problem-solve. But I initially saw my employment with the firm as almost an externship, like a doctor does, to learn how to be a lawyer.

Rana joined Fried, Frank, Harris, Shriver & Jacobson LLP’s flagship Manhattan office. “I wanted to go to a large and great firm where I would have really smart and capable lawyers around me,” she says. “Law school taught me to problem-solve. But I initially saw my employment with the firm as almost an externship, like a doctor does, to learn how to be a lawyer. I figured I’d do it for a year or less and then move to a nonprofit like the Brennan Center for Justice [a nonpartisan public policy and advocacy group] or some other nonprofit that was doing constitutional law, civil rights, and criminal law work.”

At Fried Frank, however, Rana says she got sucked into litigation work. “I really enjoyed what I was doing—a wide of litigation with a bunch of pro bono.” After a few years of commercial litigation and intellectual property litigation, the firm proposed something unusual—they would pull Rana off her other matters so that she could dedicate herself to a single case that would be, essentially, hers.

It was a pro bono death penalty case.

Heather Fine, Esq., Managing Director, Major, Lindsey & Africa

Heather Fine, Esq., Managing Director, Major, Lindsey & Africa

Over time, that capital case convinced Rana to change direction. “I really believed in my client and I identify very closely with my work. I found it extremely hard to separate the work and keep perspective on it,” Rana explains. In criminal law, “your arguments and work can lead to somebody’s death or incarceration for the rest of their lives. Or it can lead to the rest of society being exposed to a dangerous person.” Her mental and emotional connection with her work started to turn unhealthy. “I constantly worried that there was more I could do and should be doing. Every night I would fall to sleep worried. If I went out with friends, I worried that I should be researching every possible argument, even irrational ones.”

Heather Fine, Esq., a Managing Director of legal search firm Major, Lindsey & Africa’s Chicago office, says that what happened to Rana is common. “As lawyers are developing their legal careers, there is a often a pivotal moment that impacts their direction. Like Rana, many GCs would tell you they had the same somewhere along the line.”

When the case was over, Rana moved to antitrust and mergers and acquisitions (M&A). She found the economic questions intriguing and learned more about herself as a lawyer too: “It was intriguing only when it was an industry I really cared about,” she laughs.

Rana owned her dissatisfaction and took steps to find her place in the practice of law.

After another year, Rana knew she needed a break from big firm life. The self-awareness and forward thinking that characterize Rana’s career was a key part of her success, says Gloria L. Sandrino, Esq., a principal in global legal recruiting agency Lateral Link’s Los Angeles office (and a fellow Harvard Law School alumna). “Rana listened to her inner voice when she left Fried Frank. That is really important. She didn’t make her decision about Fried Frank or excuses about practicing at a firm. In my experience, that’s rare. Unfortunately, lawyers often blame the firm, or the demands of practicing in the firm, on their professional unhappiness. Rana owned her dissatisfaction and took steps to find her place in the practice of law.”

Gloria L. Sandrino, Esq., Principal, Partner and Group Recruiting, Lateral Link

Gloria L. Sandrino, Esq., Principal, Partner and Group Recruiting, Lateral Link

Heather agrees. “If you want to expand your career, even if you love the job, it’s important to know when to move on. If you get stuck at one place, fifteen years can go by and you stopped being challenged several years into it and then you are in a much more difficult position trying to find a new role. And you may get questions from potential employers about why you remained in the same role for so long.”

I’d stopped looking at the Big Picture.

In Rana’s case, five years had gone by. She’d gained 10 pounds. She’d lost touch with her hobbies. “I’d stopped looking at the Big Picture,” Rana said in her 2013 keynote address for Texas Tech University Law School. As much as she appreciated the lawyers she worked with at Fried Frank, when she looked around at BigLaw attorneys generally, she told me, “The vast majority of them looked like they hadn’t seen the sun in six months. They were out of shape. They were drinking a lot. They had failed marriages. And they had no hobbies. That’s not a life.”

“I was honest with the firm about my satisfaction and dissatisfaction,” she says, noting too that, at the time, it was a boom economy for lawyers. With her credentials and without massive student debt, she could—in a very literal sense—afford to take the risk in ways the lawyers in a tight job market don’t feel they can. If push came to shove, she says, “I knew I could get another job.”

Her risk in talking to Fried Frank about her concerns paid off. They got her a career counselor, for which she is grateful to this day. Rana and her career coach’s discussions brought her back around to her interests outside the law, sports, and her interests within the law, all of which had applications to the entertainment and sports industry. Merging the two was her career counselor’s idea. “Why didn’t I think of that?” Rana laughs. Top legal recruiter Heather Fine notes career counselors and career coaches are resources underutilized by lawyers: “It’s critical for attorneys to take advantage of career coaches. At Major, Lindsey & Africa, we regularly encourage candidates to meet with coaches.”

Rana left Fried Frank in 1999. It was still a boom time for lawyers, but rather than leave the firm outright—it’s almost always easier to get a job if you already have a job—she and the firm negotiated a six-month sabbatical. She planned to travel.

It didn’t work out.

With her credentials and without massive student debt, she could—in a very literal sense—afford to take the risk in ways the lawyers in a tight job market don’t feel they can.

A few days into her sabbatical, she was contacted by an entertainment law firm willing to work with her to make her transition from litigation to transactional law—if she took a step back in seniority. Grubman Indursky & Shire, P.C. was founded by Allen J. Grubman, a graduate of City College of New York and Brooklyn Law School. Grubman is widely considered one of the most powerful lawyers in the entertainment industry. In addition to independent producers, his client list has included entertainment royalty such as Bruce Springsteen, Madonna, U2, John Mellencamp, Rod Stewart, Sean “Puffy” Combs, Luther Vandross, Elton John, Jennifer Lopez, Mariah Carey, and Andrew Lloyd Webber. The firm had also done sports work and was considering expansion in that direction.

When I talked to career advisers and search consultants about Rana’s career journey, they pointed out that this is a perfect example of preparation meeting opportunity. For example, Jared Redick, principal of The Redick Group, says, “I often talk about the magic that happens when opportunity meets preparation. It’s not something you can predict, but it’s kismet when it happens.” (As an aside, Jared adds that these days “LinkedIn has opened more purple squirrel moments” by enabling employers and recruiters to search through millions upon millions of online profiles to find talent. LinkedIn profiles can be designed to attract the eye of a very specific audience searching for a very specific skill set.)

This was also another critical moment in Rana’s development as an attorney and in building the generalist background that would prepare her for a general counsel role. Rana had embraced the learning component of being a law firm associate at Fried Frank. Top legal recruiter Gloria Sandrino of Lateral Link (who had also been an associate at Fried Frank) notes, “Associates often become consumed with the politics of becoming a partner and simply forget to enjoy the process of becoming a good lawyer. A good lesson for all of us from Rana’s experience is that it important to first become the best lawyer that we can be, before concentrating on partnership or any other destination.”

Lan N. Nguyen, Esq., Managing Director, Chadick Ellig

Lan N. Nguyen, Esq., Managing Director, Chadick Ellig

Lan Nguyen, Esq., a recruiter at search firm Chadick Ellig in Manhattan, also noted this was a critical moment in Rana’s career. “It is important to build the blocks in your career to lead to successful transitions, as Rana did,” Lan says, “even if you don’t yet know where you want to land. In doing so, the whole story comes together coherently for the right opportunity in terms of skills, experience, reputation, and potential.”

So would Rana join Grubman? Would she take the risk and the step back that would later lead to a giant step forward

Wanting to expand her legal skill set, Rana jumped at the offer.

She spent the next year working intensively on high value production-related agreements and transactions at Grubman. Her contract negotiation skills went from a weakness to a strength. But while it was a New York firm, it operated essentially on California time—which meant hours long into the night—and the firm never expanded into sports the way Rana had hoped.

Then Rana happened upon a two-line ad for a sports lawyer in the New York Times classifieds. She called the legal recruiter who had placed the ad to find out more. It was for a job at Madison Square Garden Company (MSG). She applied.

Rana thought it was nearly certain that she’d get at least a first-round interview. Instead, she heard nothing back from the legal recruiter and nothing from MSG.

She took a different tactic. She asked a cousin who is a lawyer at the NBA if he knew someone at MSG that he could call to help facilitate the process. Could he help her get her résumé in front of someone? Her cousin made a few calls to his connections at MSG. It turns out that somewhere between the headhunter and HR, her résumé had been lost. The corporate legal department called her in for an interview.

Gloria Sandrino of Lateral Link notes how good Rana was pointing out to the in-house lawyers that she had transferable skills. “In my experience,” Gloria says, “this is so important, especially for lawyers making their first move from private practice to in-house. I always tell my candidates that their job is to connect the dots for the in-house lawyers, and show them in detail that the skills that they have accumulated in the private sector are exactly the skills that they will need as an in-house lawyer.”

Networking is a key part of being a successful lawyer.

Rana got the job.

Legal recruiter Heather Fine of Major, Lindsey & Africa notes how important this change in tactics was for Rana’s success. “I cannot stress this enough—networking is critical to getting your résumé to the right place. It’s the best way to separate yourself out of the pile. Networking is a key part of being a successful lawyer.”

A Harbinger of Things to Come

It was 1971 and Rana’s parents had tickets to the Stanley Cup semifinals at the Garden. It was Game 6 of the New York Rangers’ series against the Chicago Black Hawks. One year-old Rana and her four year-old brother were home with their babysitter as the game headed into overtime. Her father called the babysitter to let her know they’d be home late. As the game headed into second overtime, her father called the babysitter again. By the time the second overtime ended, the babysitter had enough. Leaving Rana’s mother at the Garden, her father hopped a cab home, grabbed the sleeping kids out of their beds, and carried them down to the taxi waiting outside. They made it back into the Garden as NHL All-Star Pete Stemkowski scored the winning goal for the New York Rangers in triple overtime.

Decades later, the halls of the offices at the Garden were lined with historic photos from the greatest moments in the Garden’s history. The photo outside Rana’s office? Stemkowski scoring that same goal. It seemed like fate. At MSG, Rana finally got the sports industry experience she wanted. She loved her work and the people at MSG, and never imagined leaving. “I thought it was where I would retire,” she says. “At the time, it was a dream job.”

Madison Square Garden Company is more than the arena itself. It’s a publicly traded holding company with some $10 billion in assets that’s now divided into three divisions: MSG Sports, MSG Entertainment, and MSG Media. At the time Rana was there, MSG was an LLP owned by Cablevision that had entertainment, sports, and media interests.

Rana worked primarily on team-related legal issues as Vice President (promoted from Director), Legal and Business Affairs of Madison Square Garden. She handled matters for the NHL’s New York Rangers, the WNBA’s New York Liberty, the MSG Network, and Fox Sports Net New York (now known as MSG Plus). Her world quickly became one of sports contracts: sponsorship agreements, talent agreements (for coaches, scouts, and players), salary-cap related evaluations for New York Liberty players, on-air talent agreements (for producers, commentators, and others), agreements for on-court and off-court contests, and more.

I walked the halls once a week to talk to my internal clients.

Moving in-house was a smooth transition for Rana since at the Grubman firm she had already acted as outside general counsel for independent film producers. And she loved being on the business side of things. “I walked the halls once a week to talk to my internal clients. I’d ask them about what was going, what they expected to happen the next season, and what their challenges were. Many times, that led to legal questions.” Seeing her interest in giving proactive legal advice, she was soon invited to attend weekly staff meetings for each of MSG’s sports teams.

Rana Dershowitz, Esq., General Counsel and Vice President of Aspen Skiing Company

Rana Dershowitz, Esq., General Counsel and Vice President of Aspen Skiing Company

Legal recruiter Heather Fine notes Rana brought a lot of business savvy to her role, but that also “strong business judgment and business acumen are necessities in-house, but they’re both learned skills.” Rana was deeply integrated into the MSG Sports business. Over time, her role became more complex. She got more involved in intellectual property use and protection, helped evaluate business opportunities—including potential M&A deals and joint ventures—and worked with MSG’s philanthropic arm, Garden of Dreams. When another lawyer left for maternity leave, Rana took up her role as well.

The group of attorneys she worked with was phenomenal, but after a few years, it also became clear there wouldn’t be any upward mobility. Rana loved her work MSG, as well as serving as an adjunct professor of sports law at New York Law School, but it becoming clear that if she wanted to continue to grow as a lawyer she’d have to do it somewhere else.

During a ski trip to Rockies with her now husband, Rana started seriously thinking about their next steps. He had ties to Colorado and was interested in moving away from the east coast; Rana was game for a new adventure.

From New York to Denver

The couple went to Denver to scout it out. They fell in love with the place. He was immediately offered a position and prepared to move.

Rana gave herself a few months to stay in New York while looking for a job in Denver. But she also prepared for the possibility of moving without a job lined up. She planned for six months of time between jobs, during which she could also make decisions about her personal life. Already competing in half-Ironman triathlons, she figured she could also use the time to train for a full Ironman.

Rana networked heavily to build relationships in Colorado and heard about a posting for an Assistant General Counsel at the U.S. Olympic Committee (USOC). Given her seniority at MSG, the AGC position as described felt like a step backwards, but given that Rana had been prepared to move to Colorado without any job, it seemed like a low-risk opportunity with a potentially high reward. She decided not to let the job description deter her from exploring the opportunities within the organization.

She decided not to let the job description deter her from exploring the opportunities within the organization.

Headquartered in Colorado Springs, the USOC is a federally chartered 501(c)(3) that serves as the U.S.’s National Olympic Committee as well as the U.S.’s National Paralympic Committee. As such, the USOC oversees U.S. teams for Olympic Games, Paralympic Games, Youth Olympic Games, Pan American Games, and the Parapan American Games. The USOC has exclusive rights to Olympic-related intellectual property in the U.S. It operates three training facilities in Colorado, California, and New York. Additionally, it has numerous partnerships and licensees.

After interviewing her, the General Counsel offered Rana the Deputy General Counsel role instead of the AGC position. Once Rana joined the USOC, things moved even faster.

Within two weeks after Rana started, USOC General Counsel Jeff Gewirtz announced that he would be joining the Brooklyn Nets and Barclays Center as Senior Vice President (SVP) of Business Affairs and General Counsel. Gewirtz, a graduate of Tufts University and Brooklyn Law School, was returning to his New York roots just as Rana was leaving hers. [Gewirtz is now Executive Vice President (EVP) of Business Affairs and Chief Legal Officer (CLO). He was named 2014 Sports Counsel of the Year by the Association of Media & Entertainment Counsel.]

Within a month, he was gone. Rana abruptly stepped into his role—which turned out to include the roles of Ethics Officer, Corporate Secretary, and Chief of Legal and Government Affairs.

I was now in the deep end of the pool, trying as hard as I could to stay afloat.

In retrospect, it was clear he had hired Rana to be his successor. Rana says, “I was now in the deep end of the pool, trying as hard as I could to stay afloat.” While there was overlap with the work she’d done with MSG, the work she was most versed in—sponsorship agreements—was already really well covered by another USOC lawyer. “The politics surrounding the Olympics, the government relations, legal department management, the nonprofit governance, sitting in board meetings and taking minutes—these were all completely new to me. I had never been to a board meeting, much less been Corporate Secretary taking minutes,” Rana says. “It was fascinating and wide-ranging. And I didn’t have the option to fail.”

Why did departing GC Gerwitz handpick Rana to be his successor when he knew she didn’t have experience in so many components of the USOC GC position?

Executive and legal recruiter Lan Nguyen notes, “While it can sometimes seem that the talent pool is limitless with so many people out there looking for a job, the fact is top talent with potential is very scarce.” Given the USOC’s uniqueness, no lawyer would have experience in every area under the USOC GC’s purview. Not even USOC’s existing in-house counsel. Each lawyer had a different area of focus. The IP lawyer didn’t do facilities management. The facilities management lawyer didn’t do sponsorships. The sponsorship lawyer didn’t do corporate governance. The corporate governance lawyer didn’t do employee relations, and so on.

While it can sometimes seem that the talent pool is limitless with so many people out there looking for a job, the fact is top talent with potential is very scarce.

If Rana didn’t have all the experience, what did offer? Potential for excellence in the position. Lan says, “Potential can be hard to evaluate, but as an executive recruiter I consider it to be one of the most important predictors of success, from C-suite to junior management. An executive may have all the right credentials—great schools, great companies and even a track record of success—indicating intelligence and competence. But none of these matter without the key ingredient of potential for success. Factors that predict potential might include achievement, aspiration, tenacity, vision, curiosity, flexibility / creativity, critical thinking, engagement, and relationship building / collaboration.”

Rana had all those traits. Together, those traits make her a successful attorney. Likely, what was most critical to the departing general counsel was that Rana had experience with the dynamics of the sports industry and the wide array of legal and non-legal issues specific to that industry—like intellectual property, personalities, talent-related dynamics, and athletes’ rights.

Heather Fine of Major, Lindsey & Africa says, “Rana is what we call a ‘best athlete,’ no pun intended! She was smart, had stellar credentials, fabulous training in private practice and in-house, and was an incredibly hard worker with a lot of ambition and self-awareness. Even though she didn’t have some of the skills, she could do the job and would know what she didn’t know. Industry experience is also very important at the GC level. It allows the GC to get the business and ask the right questions. It’s the business acumen piece.”

In the end, the previous GC’s chance on Rana was clearly less a gamble than it was solid decision-making: the hardest part of her transition was learning to manage the other in-house lawyers, particularly those in her peer group. “The hardest part of taking on a general counsel role is not the legal part,” she says, “it’s learning people management. Lawyers are often terrible managers. And we’re just not taught the management side. I went from managing only myself to managing ten people with, at the time, very little organizational support to help me understand my role as a manager and be successful in it.” The result? “I had some personnel challenges,” Rana admits.

The hardest part of taking on a general counsel role is not the legal part.

Heather says team management is a common problem for lawyers. “The more management experience a lawyer can get in-house, the better. People are tough and people management is a learned skill. A mentor in this area is important. Also, managing in law firms is not the same as managing in-house—lawyers don’t always like to hear that, but it is the truth.” Jared Redick agrees. He adds, “Team management and mentoring of internal talent can be challenging at first, but they’re critical leadership skills and—as you go up the corporate ladder—actually part of executive job descriptions.”

True to her history, Rana was up to the challenge and got her feet under her. By 2012, she was named one of Sports Business Journal’s Game Changers: Women in Sports Business.

Time for Another Challenge

There seemed to be only two options: either leave USOC or restructure the demands of her position. “I walked into the CEO’s office prepared to quit,” she says. Instead, they worked together to change the reporting structure of her in-house team: she oversaw their legal work, but the attorneys themselves were embedded into business units. Going forward in-house counsel would have solid line reporting to the business units, and dotted line reporting to Rana for legal matters in a newly titled Chief Legal Officer (CLO) position. [Take a look at Rana’s discussion of this situation in her May 2013 keynote address at Texas Tech University School of Law graduation.]

Embedding the lawyers was a solution that worked from several perspectives. “It made them more effective,” Rana told me, “because it helped the business people understand that the lawyers were part of their team—not outsiders.” The change also allowed Rana to focus on her strengths—Big Picture and legal issues—rather than on time-consuming people management.

The diversified model worked, but wasn’t perfect. Nor was the organization’s response to Rana’s periodic telecommuting. She felt isolated from the other lawyers and, at the time, telecommuting wasn’t generally accepted.

A friend put a retained search recruiter in touch with her. The recruiter’s assignment was to fill the general counsel role at Aspen Skiing Company. During their chat, it became clear that it was worth pursuing to see if Skico and Rana were a good fit. She had been a competitive skier in college, and looked forward to moving back to the for-profit business model rather than risk being pigeonholed in the non-profit sports sector. Further, as a regional rather than national organization, there would be a lot less travel. On the other hand, Skico was specifically looking for an M&A lawyer with a real estate background. Neither was Rana’s area of expertise.

Rana had been involved in some mergers and acquisitions at Madison Square Garden. The USOC doesn’t have M&A as an issue, but it does engage in strategic business alliances and Rana found the overarching business and legal questions were generally transferrable to M&A—determinations about the future of the organization and creations of joint ventures, for example—although the agreements themselves were different. “But that’s just the paper,” Rana points out. “As GC, I’d have to think through the big issues. I’d have a lawyer who could actually write the documents.” As far as real estate went, Rana had been heavily involved in the establishment of the USOC’s new Colorado Springs headquarters, which was the result of a public-private partnership.

Throughout her interview process with Skico, Rana focused on her transferrable skills. In the end, “I talked them into it,” she jokes. It didn’t hurt that, at the time, Skico was also interested in diversifying the demographics and experiences of its leadership team. Skico was sold.

Heather Fine says, “Lawyers must always think about how their skills are transferable. What do you know that translates into the position? How are your skills an exact match in other ways? Clearly Rana was also a strong cultural fit with Skico. Culture and personality fit can be as—or even more—important than technical legal skill.”

Shortly after Rana traveled to the 2014 Winter Olympics in Sochi, Russia to provide on-site legal support for the Games, she joined Skico and has been there ever since. [See Rana’s 2011 interview about diversity in sports, and other topics, at the Sportcal 20 Years of Sports international conference in London.]

In the September 2014 press release announcing Rana’s appointment, Skico president and CEO Mike Kaplan said, “Her experience with the USOC and Madison Square Garden will prove invaluable, but most importantly her passion for the sport and the lifestyle make her an outstanding choice.”

She was succeeded at USOC by Christopher McCleary, former Senior Vice President, Senior Associate General Counsel, Global Brand and Client Management of long-time Olympic sponsor of Visa. McCleary, a University of Michigan and University of Michigan Law School grad, had several positions within Visa’s worldwide legal operations in marketing, sponsorships, intellectual property, and client licensing over nearly twenty years.

The Family Business

It’s an understatement to say that Rana comes from a family of brilliant lawyers.

It’s an understatement to say that Rana comes from a family of brilliant lawyers.

Her mother, the late Marilyn Dershowitz who had graduated from Barnard College, attended Cardozo Law School while Rana and her brother were in high school. She then served as a Manhattan Supreme Court Special Referee, presiding over several high profile civil matters, until her retirement in 2010.

Her father, Nathan Dershowitz, is a graduate of NYU Law and Brooklyn College. He’s renown as a civil and criminal appeals attorney in Manhattan and runs the elite appellate boutique firm, Dershowitz, Eiger & Adelson, P.C. His clients have included well-known figures such as Leona Helmsley, Mike Tyson, Tupac Shakur, former Louisiana Governor Edwin Edwards, and O.J. Simpson.

Her uncle, Alan Dershowitz, recently retired from 50 years as a professor at Harvard Law School where, at the age of 28, he became the youngest full professor of law in HLS history. He’s a graduate of Brooklyn College and was the valedictorian of his class at Yale Law School, as well as the editor-in-chief of the Yale Law Journal. Of course, he too is an appellate lawyer who has been involved in high profile and landmark cases, and he’s a prolific author and political commentator.

Her cousin, Jamin Dershowitz, graduated summa cum laude from University of Pennsylvania (like Rana, he is a member of Phi Beta Kappa) and earned his law degree from Yale Law School. He’s the General Counsel of the Women’s National Basketball Association (WNBA) and an Assistant General Counsel for the National Basketball Association (NBA).

Rana’s older brother is the slacker of the family. He’s a rocket scientist. No, seriously, he is. He has a college degree and a PhD from MIT in aeronautical engineering, and worked at NASA’s Mission Control Center.

How has the family business opened doors? Her uncle Alan is most publicly recognizable of the bunch. “It’s a talking point over the years,” Rana says, “although he’s never directly helped me get a job. And, frankly, plenty of people don’t like him! They see him as political more than as a lawyer.”

As in all things, Rana is reflective. She’s confident, for example, that the family business helped get her legal career started. Outside New York, however, she thinks there’s a lot less name-brand recognition, plus, “In Colorado, I’m not in legal circles. I’m much more in the business world,” she notes. “I’m not aware of any doors opening because of him in Colorado. But it’s also true that I might just not be aware of it. I could be fooling myself. It’s not like Dershowitz is a common name. I’m sure people have picked up my résumé and wondered if I’m related to him.”

More important than any flashy name recognition has been the real professional contacts her family has—remember it was her cousin, Jamin, who helped get her résumé in front of the right people at MSG for her first in-house sports position. None of which would have helped much if Rana hadn’t been an outstanding lawyer in her own right.

Lan advises lawyers to “leverage your contacts” to get their names and résumés in front of decision-makers, just as Rana did. But she added the caveat, “Do so judiciously and with credibility. In other words, if you clearly can’t sell your story to have a real shot at the role, don’t ask someone to promote your name and put their reputation on the line.”

The power of networking can’t be underestimated—and it doesn’t just refer to shaking hands at cocktail parties. “Networking is a very broad term that includes everything from connecting to learning to sharing views and thought leadership,” Lan says, “and can make a difference in getting you in front of the right position and decision-makers. When you are sponsored and endorsed, or warmly introduced by someone who is respected in the market or has power within the organization, your name and résumé go to the top of the pile. A supported reference can also overcome the competency evaluation, which may superficially rule out an otherwise strong candidate because they do not have the ‘right’ industry experience, number of years of experience, title, or specific skill sought.”

A Safety Net Enables Strategic Risk-Taking

‘I’ve always had a safety net,’ she says candidly.

Rana always been very confident. “I don’t have the fear that so many lawyers have,” she says. “I’ve never had it.”

Part of that confidence comes from the fact that Rana is smart and capable. But part of that confidence comes from the fact that “I’ve always had a safety net,” she says candidly.

Rana had more options than the average attorney. She didn’t have a heavy student debt load. She had personal and professional connections able to put her résumé in front of decision-makers. Her fallback plan was, for others, a dream job: she had a standing offer to join her father’s law practice. She had more options, flexibility, and cushion—which, in turn, empowered her to take risks other lawyers might not.

She had more options, flexibility, and cushion—which, in turn, empowered her to take risks other lawyers might not.

“I could express concerns, where I was satisfied and where I was dissatisfied,” she says. “I was much more willing to question insane hours. I got my work done, but when assignments came late in the day or in the evening and I had plans, I had no hesitation saying to them, ‘Is it necessary for me to cancel or can I start on it first thing in the morning?’”

Ability to relocate for family reasons—which has contributed to Rana’s personal and professional success—may also be a reflection of that safety net. Gloria Sandrino of Lateral Link says, “I often work with lawyers who are so desperate to pursue the ‘best’ in-house job that they forget what works for their personal life. But Rana was able to focus on the city that worked for her and her family first, and her job second.”

Rana also regularly took calculated risks, in having honest discussions with employers and in accepting positions that seemed like steps back in the short-term but enhanced her ability to achieve her long-term goals, says Gloria. “Not every stretch is a linear move forward. Just as our bodies can stretch in a multitude of directions, so can our careers and so can our minds,” Rana said in her Texas Tech keynote.

Not every stretch is a linear move forward.

The temperamental and financial ability to take calculated risks is a game-changer. “It’s more than risk-tolerance. It’s the ability to do things you care about. For me, it wasn’t about making the most money. It was about where I was going to be the most satisfied with what I was doing. There were a lot of ways to make a very comfortable salary while doing something satisfying. When you’re not constrained by very real economic issues, you have the ability to find the work you’re most passionate for, and that’s the work you’ll be best at. You can literally afford to do what you love. It’s easier to excel at work you love. It’s harder to excel at something you don’t.”

It’s easier to excel at work you love. It’s harder to excel at something you don’t.

Heather Fine notes there are lessons here even for lawyers who don’t have the same safety net Rana did. “Lawyers need to be thoughtful about their careers and take risks, especially for personal satisfaction and a happier life. It’s important to love your work. It’s 75% of what you do with your day. But liking your work can be enough too—especially if you have financial constraints that won’t allow you to take the risks that Rana took. It is still important for lawyers to recognize they are not stuck. Taking risks is part of the calculus.”

The Difference Between Quitting and Reassessing Goals

We talked about risk taking at length, including another type of risk—quitting. At several points in her education and career, Rana pivoted. For example, she did not finish her college Egyptology thesis. But there’s a difference between quitting and making a conscious choice to reassess goals and the path to reach those goals. “Don’t continue down a path that doesn’t make sense,” she advises. When it became clear that the Egyptology thesis didn’t make for her to finish, she wasn’t afraid to walk away from it. The trick and the wisdom is in “figuring out the difference between quitting something because it’s ‘too hard,’ which generally isn’t acceptable, and walking away from a path that doesn’t make sense for you.”

Heather Fine says, “I love that Rana knew when it was worth it to take a risk and even take a step back. I tell lawyers all the time to take risks, especially if they are unhappy, but of course be smart about it. Too often, lawyers are afraid to do that. Rana was very forward-thinking and it paid off.”

Advice for Aspiring Lawyers in the Sports Industry

Rana was one of the more than 150 attorneys I interviewed for the 2011 classic edition of “How to Get a Legal Job: A Guide for New Attorneys and Law School Students,” and gives great advice in her May 2013 keynote address at Texas Tech Law graduation. Among her suggestions, most of which are echoed here:

‘Your legal career doesn’t start when you get a JD,’ Rana warns. ‘It starts with where you went to college.’
  • Stretch yourself all the time

  • Set long-term goals and don’t forget to periodically reassess those goals since priorities change over time

  • Think outside the box

  • Seize opportunities

  • Cross-train as a lawyer to learn different areas of both law and business

  • See potential in others and help them grow

  • Learn about people with different backgrounds and perspectives

She’s also been involved with events hosted by ESPN, American Bar Association, the Sports Lawyers Association, Colorado Bar Association, the Hogan Lovells Global Women’s Executive Summit, and local organizations.

It’s really important for attorneys to focus on building their lawyering skills early in their careers. The business part of practicing law can be learned later in one’s career, but those early years are about acquiring the skills to be a good lawyer.

A key point she often makes is that careers actually begin much earlier than most people think. “Your legal career doesn’t start when you get a JD,” Rana warns. “It starts with where you went to college.” It’s easy to dismiss this advice as elitism, but it’s one of the realities of the legal profession—alumni networks heavily influence career opportunities after graduation. Every school has its own spheres of influence. For some career goals, attending the local college and law school will reap the greatest rewards. For other career goals, lawyers’ chances of success are far greater if they’ve attended Top 10, or even Top 3, institutions. For still other career goals, chances of success are maximized with a combination of a state or local school and a Top 3 school. (Whether or not that’s fair is a question for a whole other series of articles.)

Gloria adds, “It’s really important for attorneys to focus on building their lawyering skills early in their careers. The business part of practicing law can be learned later in one’s career, but those early years are about acquiring the skills to be a good lawyer.”

Top Three Legal Career Development Takeaways

Jared Redick, Principal, The Redick Group

Jared Redick, Principal, The Redick Group

I’m fortunate to spend a great deal of time talking about best strategies for career development, professional development, and career transitions with career transition coach and former executive recruiter Jared Redick, also quoted above. Jared is an expert career consultant for c-level executives and rising stars in Fortune 100 companies, including some of the world’s most desirable brands. We see a lot of overlap between what it takes to be a sought-after corporate leader and what it takes to be a sought-after attorney—particularly in-house counsel, since in the best organizations in-house lawyers are specialized members incorporated within the overall leadership structure.

Jared and I discussed our top three takeaways from Rana’s career journey and her series of legal dream jobs.

1. Personal Finances Can Open—or Close—Career Options.

Rana had freedom of movement. She moved to different employers and to a different state. She had freedom to take risks. As we discussed, a large part of the reason for her freedom was that she had no significant student debt. She could afford to take risks that a lawyer with $150,000 to $250,000 in student loans may not have felt able to take.

The problem isn’t limited to astronomical student debt, however. Over the years, I’ve seen—and known—many lawyers whose expensive lifestyles made it difficult to quit safe, high-paying jobs and move to more satisfying work that may pay less or that may be more risky. In one case, the lawyer had been a BigLaw associate in Manhattan for more than five years, but hadn’t managed to save or invest a dime. Jumbo mortgages and home equity lines of credit, private school tuitions, luxury cars, and sailboats are wonderful, but they’re also burdens that aren’t necessarily easy to unload if your priorities change. Having an expensive and inflexible lifestyle can mean that it’s harder to move to your dream job, so be wary of golden handcuffs and gilded cages.

2. Figure Out What You Want.

Too often, career decisions are made passively. Too many of us seek the path of least resistance—in choosing our schools, major, employment, geographical location, and more—without ever taking the time to seriously consider whether that path makes sense for us as individuals. And even if we realize we’re on a path that doesn’t suit us well, we don’t necessarily correct it. We don’t know what we want to do when we grow up. We don’t stop really think about what makes us happy. We don’t build a bridge to get us there.

In contrast, Rana was both self-aware and strategic. She regularly stepped back to examine her goals, which she then compared to her career and personal trajectory. When things were off, she wasn’t afraid to correct her course. She wasn’t afraid of being labeled a quitter because she wasn’trunning away,she waspursuing a goal. She made a conscious decision to go into sports law, figured out the technical skills she need to develop in order to transition to sports law successfully, and pursued opportunities that would build that skill set. She was willing to consider taking short-term steps back, so long as it was consistent with her long-term goal.“Telling your story authentically, but strategically, means you’ll turn off a lot of opportunities for which you aren’t a fit,” Jared says. “But you’ll also attract the opportunities for which you are just the right fit.”

3. Network, follow up, and stay open to opportunities that arise.

Many attorneys shy away from the idea of networking. They think of networking as contacting people they don’t know to ask for a job. Not surprisingly, when framed that way, networking is uncomfortable—for both sides. Attorneys tend not to want to follow up on résumé submissions either. They wrongly assume that no response is the same thing as rejection. Lastly, many attorneys ignore openings that don’t sound like a perfect fit, and they turn away recruiters who contact them. Even in today’s highly competitive job market, there are lawyers who mistakenly think of legal recruiters as annoyances rather than powerful, well-placed allies who may be the gatekeepers for some of the most exclusive legal positions in the country.

Rana did everything right. She understood networking is a professional necessity that begins well before graduation from law school. When she didn’t hear back after submitting her résumé to MSG, she looked to her network to find someone who could help her reach the decision makers. She worked to expand her networked in preparation for her move from New York to Denver. She was willing to engage with recruiters and potential employers even when she wasn’t sure there was a match, which kept lines of communication open and eventually led to her positions at the USOC and SkiCo. She also understood the difference between asking a contact to facilitate the hiring process (say, for example, by ensuring your résumé makes it to HR) and asking a contact to put his reputation on the line (say, for example, by advocating to the hiring decision-maker on your behalf). Know when you have a close enough relationship with your contact—and are confident you’re a fantastic fit for the role—before you ask your contact to put her reputation on the line for you. Otherwise, limit your ask to something simpler.


Your mission is to find your own dream job—a job you can love, a job that’s best for you—and then build a bridge to get there.

As I’ve been working on this series about how prominent lawyers ended up in legal dream jobs—starting with a senior vice president at the Boston Red Sox, I’ve discovered that the conclusion to all these articles is the same: We are not all Rana Dershowitz, or Dave Friedman, or Alphonso David. Ultimately your mission isn’t to land their dream jobs. Your mission is to find your own dream job—a job you can love, a job that’s best for you—and then build a bridge to get there.

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