Q&A with Natasha Labovitz, “Dealmaker of the Year”

Debevoise partner M. Natasha Labovitz was recently named a “Dealmaker of the Year” by The American Lawyer for her role advising Altegrity Inc. in its Chapter 11 bankruptcy, the fourth biggest bankruptcy of 2015. Natasha was one of only 12 lawyers honored in the annual list that recognizes the leading corporate lawyers and transactions of the previous year. I recently chatted with Natasha about work, life and why she abandoned the idea of separating work from her personal life. This interview has been condensed from its original form.

Q. Congratulations on the Dealmaker award for your work on the Altegrity restructuring! Within a year, you helped guide Altegrity from the brink of financial ruin to emergence from bankruptcy with its core operating businesses intact. When you approached the restructuring, what were some of the challenges you anticipated and how did you resolve them?

Altegrity faced a perfect storm of issues. The company had just completed a very successful out-of-court restructuring when a previously disclosed state-sponsored cyber-attack at one of its subsidiaries resulted in the unexpected loss of major government contracts, costing Altegrity a third of its revenue. This same subsidiary was also involved in a government whistleblower investigation that had been causing a negative overhang for Altegrity’s unrelated business operations. Altegrity had more than $1.8 billion in debt obligations and was at risk for imminent default.

When we approached Altegrity’s restructuring, we realized early on that getting to creditor consensus would be a much better strategy than trying to litigate our way into a result. We convinced other key creditor groups that litigation would be bad for business, and we were able to enter chapter 11 with strong creditor support. This allowed Altegrity to really focus on a handful of key disputes during the chapter 11, most importantly reaching a global settlement of U.S. government whistleblower claims that ended what could have been years of litigation.

Q. What would you consider your most valued career accomplishments thus far, even if you have not received formal recognition for them?

I was tremendously honored to receive the Dealmaker award, and at the same time I think a different and even more meaningful accomplishment comes through the relationships that I have been able to form with clients, industry colleagues, and my legal colleagues at Debevoise and my previous firms. Recently, a younger investment banker I’ve worked with confided in me that she was going to have a baby and asked my advice on balancing work and family because she thought I did it so successfully, which felt like a huge compliment on many levels. Moments like that, along with the feeling that comes when a client trusts us with repeat business or asks us to handle a restructuring (which is about the most “bet the company” transaction I can imagine), are the kinds of recognition that feel most meaningful.

Q.  I agree with your investment banker friend – you do seem to balance work and family quite successfully.  Do you have any strategies that help you achieve that balance that you would recommend to others?

I used to make a real effort at separating my life into “work time” and “personal time”, but I found that didn’t make anyone very happy. Clients and colleagues did not appreciate if I was non-responsive during personal time, and sometimes my family really needed me during work time – and I’m sure you can imagine that their collective lack of happiness caused me to be stressed out. I quickly learned that the better solution for me was to be my whole self all the time. This means that my kids understand I may need to take some work calls during vacations, but at the same time they know I will answer their calls or texts while I’m at work if they need me. By the same token, I sometimes openly schedule my work calls around my children’s school events and it’s not unusual for me to take a five-minute break at a client event to talk with my children before their bedtimes, but my clients know I’ll be responsive to their business anytime they truly need me, even on weekends or holidays. By abandoning the idea of a rigid separateness between “work” and “life,” I found that striking a manageable balance became much easier for me.

In this sense, there is a quote that has been particularly meaningful to me. It seems to be from a Unitarian minister, L.P. Jacks (though it’s often attributed to others), and it goes like this: “The master in the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his information and his recreation, his love and his religion. He hardly knows which is which. He simply pursues his vision of excellence at whatever he does, leaving others to decide whether he is working or playing. To him he’s always doing both.” I sort of wish Jacks had not framed this in the gender-limiting terms of “his” and “he,” because this is the single best advice I could imagine having received as a young working mother.


Q. Despite the gender-limiting formula, I think L.P. Jacks’ focus on work and play is very fitting for you. I’ve always admired your ability to make the job of being a lawyer fun. Any tips?

I am so thrilled that you said this! I grew up in Vermont, so two of my very first entrepreneur-type role models were Ben and Jerry (of ice cream fame). Their early corporate motto was “If it’s not fun, why do it?” and a Ben & Jerry’s bumper sticker with that motto hangs over my desk to this day.

Let’s be honest, being a lawyer isn’t always fun:  our job is to do the thankless task of spotting little issues and following them through with serious attention to detail, or giving advice to our clients that can sometimes include unwelcome news. But I do like to create as much room as possible for having fun while we’re working hard. I think one key ingredient in that is not taking myself or any of the rest of us too seriously: we’re naturally going to do silly things from time to time as we try to juggle everything going on in our lives, and if we can laugh at our errors, it takes some of the stress out of it. Another element of making the job more fun is trying to create a team environment in which people can be their authentic selves. I’m totally comfortable sharing the funny things that happen in my personal life, and I think others on our team are also. This has led to some great “belly laugh” moments in our practice group lunches, as we talk about my nanny’s fascination with astrology and how it might impact our legal practice, or swap stories about the worst vacation ever, or rib a friend about what it will be like to meet his fiancée’s family for the first time. Work is more fun if we know and enjoy the people we are working with and can share more with them than just the legal analysis.

Q. I’m starting to sense a “work hard, play hard” theme.  Do you have a favorite word or motto and what does it mean to you?

That’s an easy one. Moxie is my favorite word. Its dictionary definition is “(1) the ability to face difficulty with spirit and courage; (2) aggressive energy or initiative; (3) skill or know-how.” I thought that described so many of the amazing professional women I know, so I had mugs made with that definition and added “(4) It’s a girl thing.” That definition went on the back of the mugs and the front said “got moxie?” in an homage to the “got milk?” logo. Since then, the idea of moxie has become a rallying cry among my women friends in the restructuring industry, and people send me emails and pictures and phrases that are moxie-related.

​​Q. What do you wish you’d known when you were starting out as a lawyer?

I don’t think I realized how much value I would place in my network, both professionally and personally. I know I missed so many opportunities to make a personal or professional connection with people I worked with, or when I did make that connection I would all too often fail to follow up, meaning that the relationship over time became more distant. I wish I had realized as a younger lawyer how simple it can be to drop someone an email or casually stay in touch with a Facebook post here and there. I started cultivating my business relationships much more consciously about a decade ago, and that has paid professional dividends for sure, and even more importantly has made me feel much more fulfilled as a person because many of my professional contacts have become genuine friends.

I also spent a lot of time figuring out what I wanted to do with my life and career and planning for that. I wish I had known then how unpredictable life is, and that it’s possible to be very fulfilled and happy even if things turn out very differently from the way we plan them. I think if I had realized that 25 years ago, I could have taken all the time I spent planning and done something else with it!

​​Q. What would you like to do more of in the future?

I hope to eventually have a better ability to relax and be still. Right now, I’m always doing something (actually usually juggling a lot of things) and that’s necessary – between a busy legal practice and being a really engaged mom to my two boys, not to mention trying to be involved in the community and see a little bit of the world and get some exercise in, the only time I’m still is when I’m sleeping. I’m having fun now, but I imagine I eventually may reach a stage where I want to slow down and savor some things more – like grandchildren, and spending more time in my house in Vermont, where the pace of life is entirely different.

Sasha Linney is an associate in Debevoise’s New York office.

Comments? Suggestions? We’d love to hear from you. Send us an email at women@debevoise.com.