Community//

Tobi Lebowitz of Jushi Holdings: “You will be treated differently as a woman in the legal industry”

You will be treated differently as a woman in the legal industry, no matter how hard you work or how good of a lawyer you are. I have had to order lunch or get the coffee during high-powered meetings, asked if I am a court reporter while waiting for a hearing to start, and singled […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

You will be treated differently as a woman in the legal industry, no matter how hard you work or how good of a lawyer you are. I have had to order lunch or get the coffee during high-powered meetings, asked if I am a court reporter while waiting for a hearing to start, and singled out as the peer to take notes or schedule the conference call. It is definitely getting better as I stand on the shoulders of women who practiced before me. Attorneys in positions of influence, like myself, speak about it more freely and strive to make sure it doesn’t happen to other women.


As a part of my series about “5 things I wish someone told me when I first became an attorney” I had the pleasure of interviewing Tobi Lebowitz.

Tobi Lebowitz brings extensive legal and human resources expertise to her role as EVP and Co-Head of Legal Affairs at Jushi Holdings Inc., a vertically integrated, multi-state cannabis company. Before joining Jushi in January of 2019, she served as the Associate General Counsel of KLX Inc (formerly KLXI), where she played pivotal roles in the sale of its aerospace segment to Boeing for 4.25B dollars and the spin-off of its energy segment into a new, publicly traded company (KLXE). Tobi earned her BS from University of Florida and JD from University of Florida — Frederic G. Levin College of Law and holds a Senior Professional in Human Resources certification.


Thank you so much for joining us! Our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law?

You could say I’m a bit of a rebel at heart. My dad wanted me to join the family business in financial planning but I found that questioning the status quo, debating and writing better suited me. Little did I know, I’d end up spending a significant part of my legal career navigating the business world, focusing on client engagement and playing a “psychologist” role, all skills I credit my parents for teaching me from the family business. After being a litigation partner at a full-service law firm, my path eventually led me to become the Associate General Counsel of KLX (formerly KLXI), a major distributor and service provider for the aerospace industry that was later acquired by Boeing, and eventually became the EVP and Co-Head of Legal Affairs at Jushi Holdings Inc., a vertically integrated, multi-state cannabis company.

Can you share the funniest or most interesting story that occurred to you in the course of your law career?

Prior to eDiscovery being such an integral part of litigation, large firms used to have their first- and second-year associates go to a client’s office to review discoverable email or arrange for the email to be physically printed and then review boxes of it. I can’t disclose anything in particular, but I remember coming across a number of entertaining emails that made me laugh out loud, which certainly made the never-ending document review somewhat enjoyable.

What are some of the most interesting or exciting projects you are working on now?

Every day is interesting when you work for a cannabis company. Take the challenges that any business might face, then add layers of complexity due to marijuana being listed as a Schedule 1 drug on the CSA and matters of first impression. The case law explaining otherwise applicable statutes and regulations are new or don’t address cannabis companies specifically, so you just have to work a bit harder and think outside the box to solve what would normally be considered ordinary legal issues.

What are some of the most interesting cases you have been involved in? Without sharing anything confidential can you share any stories?

I clerked for the federal magistrate judge that handled Wesley Snipes’ tax evasion case. It was definitely fun to attend the proceedings and see what fancy custom suit Wesley was wearing that day, and he is also much shorter than depicted in movies!

More substantively, I’ve handled very interesting M&A litigation, mostly involving breaches of reps and warranties. One particular case was litigated in Germany but required to be conducted in English. I attended as in-house counsel and the company’s representative, not realizing that I’d be required to make numerous oral arguments. It happened to be more fun than my usual in-house role directing outside counsel by incessantly sending over sticky notes and kicking them under the table.

My litigation experience has been invaluable and provides a proactive perspective on drafting to avoid litigation, where possible, as I find myself spending more time on transactional work in my current role. Even with the best drafting (usually prepared by my Co-Head of Legal Affairs, Matt Leeth), there’s always the possibility that M&A counterparts, particularly in the cannabis industry, don’t live up to their bargain, resulting in litigation. It definitely keeps me on my toes!

Which people in history inspire you the most? Why?

I’m inspired by individuals who have the courage to fight for social justice on behalf of others. There’s a poem by Martin Niemoller, “First they came…”. I learned it in middle school and it always stuck with me. There are so many people right now standing up for others who cannot stand up for themselves or do not have the platform to do so. I try to do my part by using my skills as an attorney to volunteer for causes that espouse that message, such as local legal aid organizations, expungement clinics, and most recently, voter protection work.

What advice would you give to a young person considering a career in law?

It’s nothing like Law & Order (or Suits, which is what I presume young adults watch nowadays). Very few lawyers go to trial. If being in the spotlight is your thing, perhaps becoming a reporter or social media influencer might be a better suited career. Lawyers are usually found behind the scenes advising their clients on what to do or what not to do. A lot of time is spent reading and writing.

If you had the ability to make three reforms in our judicial/legal system, which three would you start with? Why?

  1. Proportionate criminal sentencing to reduce the over-criminalization and racial injustice that currently exists.
  2. A focus on professionalism to address unethical legal tactics amongst lawyers, and in some cases judges, that result in unfair judgments which are not based on the facts.
  3. An increase in defense funding for indigent defendants for both criminal and civil cases. The Sixth Amendment provides the assistance of counsel for criminal trials, but there is no such right for civil defendants who are often evicted, lose their homes and find themselves in even worse financial situations than before the case, sometimes due to not understanding their rights or not knowing how to navigate the judicial system. Many lower level courts are doing a better job and providing guides and forms so individuals can represent themselves pro se, but a form may not work for a credit card or loan dispute, and legal aid organizations lack the necessary funding to take on every case.

How have you used your success to bring goodness to the world?

My husband, who I met in law school, is also an attorney. Our free time is limited, given we both work long hours and have young children, but we do what we can. During the election, I worked on voter protection rights most weekends and some evenings during the week, while my husband took full-time parenting duties with no breaks. We take turns doing these types of initiatives.

I know this is not an easy job. What drives you?

I’m competitive by nature and very driven by the prospect of successfully overcoming a challenge. Working in the cannabis industry, I can say that I have been met with a challenge almost every single day.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or an example for each.

  1. There are so many different types of jobs that you can have as a lawyer, not just litigation or transactional law (which is the focus in law school). I’ve met lawyers that are both the CEO and GC of a business, support TV show writers, work on cutting edge technology and engineering, head up Human Resources for large companies and work on investigations around the world.
  2. Client relations is just as important as the legal work product requested. You can be the brightest legal mind but not know how to provide practical advice that your client can follow. Those “soft” skills are not taught in law school and are hard to learn unless you are lucky enough to have a boss or mentor giving you a peek into that part of the practice, or for the very few that are naturally talented in that area. If your boss isn’t doing this for you, get a mentor! People want to do this; you just have to ask. I mentor two women — one in law school and one 6–7 years in practice — and it is so rewarding!
  3. You will be treated differently as a woman in the legal industry, no matter how hard you work or how good of a lawyer you are. I have had to order lunch or get the coffee during high-powered meetings, asked if I am a court reporter while waiting for a hearing to start, and singled out as the peer to take notes or schedule the conference call. It is definitely getting better as I stand on the shoulders of women who practiced before me. Attorneys in positions of influence, like myself, speak about it more freely and strive to make sure it doesn’t happen to other women.
  4. Being a lawyer is not the type of job you leave at the office. “Zealous advocacy”, part of the oath that a lawyer takes, means just that. For litigators, your schedule is at the mercy of the judge, your client and the opposing counsel. For non-litigators, your client’s problems happen at any time and, if they take your good advice to call you anytime, they will — even on a Sunday night at 11pm, right when you are about to fall asleep!
  5. You cannot do it all! Sometimes I have to reset client expectations so I don’t miss an important milestone like a holiday show at my daughter’s school or a day off to spend time with my son. Sometimes my family gets the shaft — last winter break, I spent the entire vacation sitting at my parent’s kitchen island on my laptop working on a deal while the kids played with the rest of our family (thankfully, my mom made sure I was fed and always had a glass of red wine ready for me around 6pm).

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

To me, the people that I’d most want to grab a meal with are those who spend their days fighting for social justice. I’m not one to be enthralled with famous individuals, so I’d be more interested in meeting with anyone on the frontlines who is fighting daily to promote and secure a better life for future generations.

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Maxine Kozler & Jennifer McGlone of LawChamps: “Embrace Your Customer”

by Jerome Knyszewski
Community//

Danielle Fontanesi: “Whether you think you can or think you can’t, you’re probably right”

by Candice Georgiadis
Community//

Lawyer and Author Kelly Bagla: “If you want something, you go after it with all your heart or don’t bother at all” with Marco Derhy

by Marco Derhy
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.