3 Questions For A Biglaw Refugee Turned Biglaw Vice Chair

Read on for a range of insights from Bill Isaacson, including preparing for a career as a trial lawyer and the value of taking ownership over your legal career.

Bill Isaacson (Photo via Boies Schiller)

Back in 2016, I wrote about rediscovering one of my favorite voices, ESPN’s Tony Kornheiser, and how his move from radio to podcasting offered lessons for lawyers hoping to strike out on their own. In particular, I focused on what prospective Biglaw refugees could learn from the 71-year-old Kornheiser’s focus on delivering a quality product to his listeners via a new medium.

Years later, I am still listening to the podcast, enjoying the rotating cast of characters discussing sports, culture, and the news of the day. All delivered alongside Tony’s detailed descriptions of his various physical ailments, as well as his general frustration navigating 2019 as a technophobic, cash-paying, intolerant of stupidity, one-percenter who is not afraid to mix it up with a home-invading flying squirrel or aggressive deer when the hour calls. Throw in humorous critiques of the ad copy submitted by the advertisers who keep the lights on and some user-submitted original music and jingles — it all adds up to an hour well-spent each day. (Even if my high schoolers protested vociferously when the podcast’s name was reflected on our car’s radio display screen while driving carpool at 7 a.m. This was a major embarrassment, even though I was listening to the show on my earphones. Which in and of themselves are embarrassing, since they are not Airpods. Can’t win.)

Carpool faux pas aside, one of the recurring surprise guests on Tony’s podcast is his friend and legal luminary, Bill Isaacson, who is only one of the leading antitrust lawyers in the entire country, as well as the Vice Chair of Boies Schiller, where he was one of the original lawyers to join the then-startup firm, leaving a Biglaw partnership to do so. As I have had a long-held interest in the intersection of IP and antitrust, fueled recently by a spate of interesting cases raising antitrust issues in the context of standard-essential patents, I reached out to Bill in the hopes that he would agree to a written interview for this audience. As gracious as he is celebrated, he agreed, and I am pleased to share Bill’s insights on a range of topics, including preparing for a career as a trial lawyer and the value of taking ownership over your legal career.

As usual, I have added some brief commentary to the answers below and in next week’s second installment, but have otherwise presented Bill’s answers as he provided them.

1) You went to college on a debate scholarship and are now a Fellow of the American College of Trial Lawyers. Looking back, do you think you were destined for trial work or was it your experiences in law school and beyond that led to a career in the courtroom?

I spent my high school years (at Marquette High School in Milwaukee) focused on debate, which did end up paying my way through college (at the University of Redlands in California).  Many debaters I knew then marched into law school. Law firms are riddled with ex-debaters, and I do not know many debaters that became doctors. I believe the reason for that is not so much the oral advocacy we learned, it is more the time we spent on research and structuring of complicated materials into arguments and presentations.  Because of debate, for example, I was researching in the law library in high school. Debate taught me more about how to prepare for trial than it did about how to communicate at trial. I eventually decided that “arguing” like in a debate was not always the best method of communication in court, and that my goal in court should be to have a (persuasive) conversation with a judge or jury. 

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GK: Bill makes a strong argument for exposing more students, particularly at a younger age to debate. As someone who teaches a high-school elective class on IP, I understand the importance of working with students on their writing skills. At the same time, giving them a taste of “getting on their feet” — while also developing their research skills so they are prepared to speak coherently and persuasively — is an important ingredient. And Bill’s points on the importance of developing research skills and learning to speak to your audience should resonate with any IP lawyer who gets (or hopes) to speak in a courtroom.

2) What is the biggest lesson you learned from taking the leap as a newly minted Biglaw partner to join Boies Schiller as one of the founding lawyers and how would you turn that experience into advice for other lawyers contemplating a similar move?

We just passed 22 years since the founding of the firm.  One part of the experience of practicing law in a law firm is that you are part of business.  It is a unique opportunity to help build a business with your colleagues (whether it is a new firm, a department, a practice area, etc.) in the environment and with the clients that you want. I recommend grabbing that opportunity if you get it.  Joining this firm at the beginning was the best professional decision I ever made. And I would have no regrets if it had turned out less successfully than it did.

GK: Speaking from personal experience, all I can say is that I agree with Bill wholeheartedly on the immense personal satisfaction that comes with helping to build a business. Especially with people you want to build it with, doing the work that you want to do, for the clients you want to work on behalf of. As weighty as the challenges are, the rewards are just so much sweeter for them.

3) For the past few years, you have often been mentioned as a spectator, and sometimes speaker, on Tony Kornheiser’s popular podcast. How important is it for lawyers to maintain friendships with people outside of the profession, whether or not they are famous?

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We all need friends in our lives who make us laugh.  Although Tony’s television show PTI is more famous, I met Tony through his radio show.  I ended up through my brother (who is a Broadway producer) arranging good seats for Tony at Broadway plays and going to the theatre with him and the podcast regulars. The tickets for Tony became a running joke on his show and we became friends.  Tony’s audience often arranges for him all sorts of benefits (and well as sending him junk) and he provides laughter to his listeners in his podcast (“La Cheeserie!” to any other of the podcast listeners.). All in all, it is a healthy relationship. 

GK: For my thoughts on Tony, go back and re-read the intro paragraphs to this column. La Cheeserie to all. 

Next week, we will conclude our interview with Bill, focusing on some of his famous successes in the IP and antitrust arenas.

Please feel free to send comments or questions to me at [email protected] or via Twitter: @gkroub. Any topic suggestions or thoughts are most welcome.


Gaston Kroub lives in Brooklyn and is a founding partner of Kroub, Silbersher & Kolmykov PLLC, an intellectual property litigation boutique, and Markman Advisors LLC, a leading consultancy on patent issues for the investment community. Gaston’s practice focuses on intellectual property litigation and related counseling, with a strong focus on patent matters. You can reach him at [email protected] or follow him on Twitter: @gkroub.