image courtesy of Jeffrey Lenkov

I remember the first time I ever got a call from Jeffrey Lenkov. It was 10 years ago, and I was backstage at the Billboard Music Awards with Ciara for a strategic business partnership that I had created between Teen Vogue and BBMA as their full-access behind-the-scenes social media partner. 

I listened to his brief and blunt voicemail "This is Jeffrey Lenkov, call me back." And immediately asked a friend (who just happened to be a founding partner at one of the most prestigious PR companies in the world, and who was handling the event) while we were with Ciara, who was getting ready backstage. His response was unforgettable- "this is either something very good, or you should leave the country immediately". 

It turned out that it was a very good call - and following the opportunity he brought me that day, Jeffrey and I formed a great professional partnership and even more so a personal friendship. I'm grateful that after our decade-long friendship and working relationship missed calls from each other will never go unreturned.

Lenkov is quite simply a sledgehammer when he needs to be, he is often referred to as the "bulldog" because of his relentless ability to get what many lawyers would consider "impossible outcomes".

While he never discloses anything about who his clients are, or who he has represented, a quick trellis legal docket search brings him up as heading litigation (and almost always as the sole lawyer), representing Fortune 50, and Fortune 500 companies including Walmart, Tesla, Target, Caesars Entertainment, Kohls, Bloomingdale's, Albertsons, Footlocker, Macy's, IKEA, Nokia, AEG worldwide, The Los Angeles Lakers, The Texas Rangers, CVS, Home Depot , Westfield, Victoria's Secret, National Hockey League (NHL), American Airlines, FedEx, Hilton Hotels, Marriott International, Hyatt Hotels, MGM resorts, Live Nation Entertainment and the Universal Music Group as well as countless Celebrities and Athletes.

In this candid conversation for Flaunt magazine, I asked the acclaimed attorney Jeffrey Lenkov to speak with Saba Vaziri, a 23-year-old junior lawyer who is just beginning to start her career, after studying at the London School of Economics. She currently works in the Middle East (with a 'magic circle' law firm nonetheless) about all the questions that many who will be reading and discover this article, perhaps those beginning their careers also, currently studying law or even just considering the option of a career path like this - would find incredibly beneficial to know, especially considering they are being answered by Jeffrey Lenkov who is undoubtedly the best of the best. 

Saba Vaziri (SV): Jeffrey, you've had an illustrious career, but let's start at the beginning. What inspired you to enter the legal field?

Jeffrey Lenkov (JL): Interestingly, there were no lawyers in my family, so I didn't have a direct role model in the profession. I came from a modest, middle-class background, and I didn't grow up knowing anyone with immense wealth or influence. For me, the law represented an unparalleled opportunity to open doors that otherwise seemed inaccessible.

Early in my career, I had the chance to go in-house at a major gaming company —started by two of my friends. It was an incredible opportunity, financially and professionally, but I turned it down. I believed in practicing law and felt that building a career in private practice offered the kind of long-term growth and impact I was seeking.

SV: That decision must have been tough. How did you navigate those early years in the profession?

JL: Being a junior lawyer is tough—it's a grind. You spend years in law school, imagining a glamorous career, only to be hit with the reality of long hours, immense pressure, and steep learning curves. It's a constant test of your determination.

The legal profession can be daunting for new lawyers, especially those grappling with imposter syndrome or questioning whether law was the right choice. But it's also an incredible equalizer. The practice of law has the power to take someone from a modest background and give them access to political, business, and financial opportunities they might never have imagined.

SV: You've often spoken about the challenges of law school. How do you think it's evolved over the years?

JL: Law school today is more transactional. It's a business. They focus on getting students in and out without necessarily equipping them with practical life skills. There is often little mentorship, and the transition to the real world can feel like being a baby giraffe dropped into the savannah—you're expected to walk and survive immediately.

Once you start at a top firm, the expectations are sky-high. You're locked into a system, and the grind begins. But I always tell young lawyers: focus on what you do best and what makes you happy. The practice of law is a marathon, not a sprint.

SV: You've described the legal profession as a "ticket to success." Can you elaborate on that?

JL: Absolutely. Practicing law opens doors to some of the greatest opportunities in life. Whether it's through entrepreneurial ventures, leadership roles, or simply maximizing your potential, the skills you gain as a lawyer are invaluable.

While other careers might offer faster financial rewards, law offers something deeper. It gives you the ability to influence society, build lasting relationships, and achieve personal and professional fulfillment.

SV: You've also emphasized the importance of taking risks. What advice would you give to young lawyers about embracing risk?

JL: The profession often teaches you to be risk-averse, but nothing great comes without risk. Fearlessness is crucial. I've seen lawyers stay in the same firm for 30 years, content with a steady paycheck. But that paycheck can be the enemy of innovation.

You owe it to yourself to explore who you are—socially, personally, and professionally. If I could give my younger self advice, it would be to be fearless in everything. Don't be afraid to take chances, because without risk, there are no great rewards.

SV: Where does your fearless mindset come from?

JL: It's a mix of influences. My parents instilled resilience and determination in me, and my brother and friends taught me to embrace challenges. There's also an innate drive—I never let tasks go unfinished, and I've always been relentless in pursuing my goals.

SV: You've also spoken about the importance of leaving environments that suppress growth. Can you expand on that?

JL: One of life's biggest regrets is wasted time—whether it's staying in the wrong job or surrounding yourself with people who don't share your vision. If you're in an environment that stifles your potential, you need to leave.

Success isn't just about financial rewards; it's about creating meaningful moments, building relationships, and experiencing life. Hard work will bring financial success, but it's the memories and connections you build that truly matter.

SV: Finally, what's your secret to building a successful legal practice?

JL: It's about relationships. Everyone you meet has value, even if they come from modest means. People have unique skills, networks, and abilities, and recognizing that is key to building lasting connections.

I've always had an insatiable drive to achieve. I thrive on capturing information, staying relentless, and seeing every task through to completion. But above all, success comes from understanding your strengths and using them to create opportunities for yourself and others.

SV: Jeffrey, your journey is incredibly inspiring. Thank you for sharing your insights with us.

JL: Thank you, Saba. It's been a pleasure.