Jeffrey Deskovic was wrongfully convicted as a teenager and spent 16 years in prison before DNA evidence led to his exoneration. Today, he is an attorney, advocate, and founder of the Jeffrey Deskovic Foundation for Justice. In this episode, Jeffrey shares how he maintained hope, why he went to law school, and how he's using his legal career to help free others and fight for criminal justice reform. 

Lawyer Side Hustles

Jeffrey's work extends far beyond representing clients in court. He has written more than 200 articles, speaks nationally and internationally, participates in policy advocacy, works with criminal justice organizations, operates a nonprofit foundation, and uses media appearances to educate the public about wrongful convictions. For Jeffrey, public education is directly connected to changing the systems that allow wrongful convictions to happen.  

“The public education as the first step towards legislative changes is what the philosophy is, which is the same reason why I speak, the same reason why I do the interviews,” Jeffrey Deskovic expresses in Episode 263 of You Are a Lawyer.

Writing has also become a creative outlet for Jeffrey. He describes building an article almost like creating a piece of art, deciding what arguments to make, how to transition between them, and how to combine statistics, case examples, and his own experiences. That work allows his advocacy to reach people he may never meet, including incarcerated people who have later told him that simply knowing his story helped them continue fighting. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Misty Leon returns to You Are a Lawyer after leaving her corporate in-house role to launch Practical Counsel Advisors, a consulting firm helping small and mid-sized law firms improve their operations and navigate AI. In this episode, Misty shares why she stopped waiting to make her career change, what lawyers should understand about adopting AI, and why sometimes the most important career question isn't whether you can do something, but whether you still want to. 

Lawyer Side Hustles

Misty didn't wait until leaving her corporate position to begin creating her next chapter. She spent months preparing Practical Counsel Advisors while continuing to work full time, using AI and other tools to help build the infrastructure of the business. The transition required additional work and less certainty, but it also gave her the opportunity to test her ideas before making the leap completely. 

“I've always found the best way to get started is to just take that first step,” Misty Leon expresses in Episode 262 of You Are a Lawyer.

That first step doesn't have to be quitting your job tomorrow. Misty's story shows how a future business, side project, new skill, or professional interest can begin alongside an existing legal career. The important part is moving beyond thinking about what you might eventually do and finding one tangible action that moves you toward it. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Elektra Yao is an international attorney, law firm founder, and lifelong creative who built a legal career serving artists and creators. In this episode, Elektra shares how studying and working internationally shaped her approach to law, why she considers law her creative medium, and why young attorneys should network, experiment, and fail faster. 

Lawyer Side Hustles

Elektra encourages young lawyers to think of career development almost like having two jobs. The first is becoming excellent at the substantive work of being an attorney. The second is intentionally developing relationships, joining committees, finding mentors, attending events, and creating a professional reputation that exists beyond a job title. That additional investment can create options when an unexpected career change eventually arrives.

"For my baby attorneys, my young attorneys, fail faster. Fail faster, fail faster,” Elektra Yao expresses in Episode 261 of You Are a Lawyer.

For Elektra, experimenting early is preparation rather than failure. She encourages lawyers to use the early years of their careers to meet people, test ideas, develop skills, and make themselves known within the legal community. As responsibilities increase later in a career, time becomes increasingly valuable, making those early relationships and experiences an important professional foundation.   

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Kayla Williams-Campbell is Deputy Director of Community Legal Services of Prince George’s County, where she oversees attorneys, manages grants, and supports eviction prevention programs. In this episode, Kayla shares how networking opened doors throughout her career, why public service became her passion, and how young lawyers can build careers around work they genuinely care about. 

Lawyer Side Hustles

Kayla’s career story expands the idea of what lawyers can build beyond traditional client representation. Although she isn’t pursuing a conventional side hustle, her role requires her to use skills that reach far beyond litigation. Grant writing, program management, data reporting, staff supervision, training development, and organizational leadership have all become important parts of her work. Those skills have allowed her to create impact without spending every day in the courtroom. 

“I just want to highlight the importance of taking advantage of different areas of law that your office provides,” Kayla Williams-Campbell expresses in Episode 260 of You Are a Lawyer.

That approach has allowed Kayla to explore expungements, domestic violence matters, wills, and other areas beyond eviction prevention. Rather than allowing a job title to define the limits of her experience, she intentionally looks for opportunities to learn. For young lawyers, that mindset can turn a single position into a much broader professional education and create options for future career moves, leadership opportunities, or entirely new directions. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Kristen Porter built a successful niche law firm in Australia, sold 75% of the business, and returned to her first love: marketing. In this episode, Kristen shares how entrepreneurship helped her rediscover her creativity, why lawyers should market according to their personalities, and why choosing one career path doesn't mean you're stuck with it forever. 

Lawyer Side Hustles

Entrepreneurship has been a recurring theme throughout Kristen's career. Her law firm wasn't built like a traditional practice. Alongside custom legal services, the firm developed an online template store, a subscription membership model, courses, and training for real estate agents. Those experiences allowed Kristen to explore the creative and business-building side of herself that had been largely dormant during her earlier legal career. 

"I think once I went to law school, the creativity side of my brain just turned off,” Kristen Porter expresses in Episode 259 of You Are a Lawyer.

Building her firm helped turn that creativity back on. Kristen discovered that she loved creating, launching, and marketing businesses, eventually leading her to establish a marketing agency specifically for law firm owners. Instead of leaving her legal experience behind, she found a way to combine it with the career she originally wanted.  

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Nikita Lamar is a Texas attorney, entrepreneur, mediator, and author who built a virtual law firm while living in Mexico. In this episode, she shares how taking an unconventional path to law school shaped her career, why estate planning became deeply personal, and how lawyers can create careers that fit their lives instead of fitting into outdated expectations.  

Lawyer Side Hustles

Nikita's entrepreneurial mindset extends far beyond her law practice. Inspired by gaps she observed in the legal profession, she developed The Last Laugh, an estate planning journal that helps families organize important information before it's needed. More recently, she created Divorce Retreat, an innovative service that combines mediation, legal guidance, and professional resources into a collaborative experience for couples seeking an amicable divorce. 

"You can create anything with your law degree,” Nikita Lamar expresses in Episode 258 of You Are a Lawyer.

Rather than waiting for someone else to solve problems she repeatedly encountered, Nikita chose to build solutions herself. Whether developing new legal services, writing resources for clients, or embracing virtual practice, she continues finding creative ways to use her legal education beyond traditional practice. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Lee Rudin is a New Orleans personal injury attorney and founder of Get Rude, a law firm built around bold branding, authentic marketing, and exceptional client service. In this episode, Lee shares why he left defense work to represent injured people, how building a recognizable brand has transformed his practice, and why lawyers shouldn't be afraid to show their personality. 

Lawyer Side Hustles

Building Get Rude wasn't simply about opening a law firm. It was about creating a business that reflected Lee's personality while helping potential clients feel comfortable reaching out. Instead of relying solely on traditional advertising, he embraced social media, humor, costumes, and memorable content to stand out in a crowded marketplace.    

"You just need to be authentically you,” Lee Rudin expresses in Episode 257 of You Are a Lawyer.

Lee explains that branding isn't about pretending to be someone else. It's about leaning into what naturally makes you different. His willingness to embrace creativity while remaining an excellent attorney has allowed him to build a practice that feels genuine and memorable, proving that authenticity can be one of a lawyer's greatest marketing advantages.  

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Sam Mollaei is a California attorney, entrepreneur, and founder of Legal Funnel. After realizing traditional legal practice wasn't the life he wanted, Sam built multiple virtual law firms and now teaches attorneys how to automate client acquisition, streamline their businesses, and create practices that are virtual, scalable, and designed for freedom. 

Lawyer Side Hustles

Legal Funnel began after Sam successfully applied online sales funnels to his own law firms and realized other attorneys could benefit from the same systems. Today, he mentors hundreds of lawyers through group coaching, teaching them how to automate client intake, delegate work, and build businesses that continue growing without sacrificing their personal lives. 

"I love giving. I love sharing,” shares Sam Mollaei in Episode 56 of You Are a Lawyer.

For Sam, mentorship has become just as meaningful as entrepreneurship. After experiencing the impact of having his own business mentor, he now helps attorneys create sustainable firms while encouraging them to think differently about what's possible with a law degree. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Ruma Mazumdar is a New Jersey real estate and estate planning attorney who built a successful virtual law firm after leaving Big Law. In this episode, she shares how working as a paralegal shaped her legal career, why she chose entrepreneurship despite growing up around family business, and how redefining success led her to build a practice that supports the life she actually wants.

Lawyer Side Hustles

Launching her own law firm wasn't originally part of Ruma's plan. Growing up with entrepreneur parents, she witnessed the sacrifices that came with running a business and initially wanted the stability of traditional employment. But after several years in private practice and the shift toward remote work during the pandemic, she realized she wanted to build something on her own terms.   

"I wanted to just have that sort of life,” Ruma Mazumdar expresses in Episode 255 of You Are a Lawyer.

Today, Ruma operates a fully virtual law firm while living outside the state where she practices. She has also embraced human design as a framework for understanding how she works best, allowing her to build a business that prioritizes sustainability over constant growth. Her journey demonstrates that entrepreneurship isn't simply about owning a business. It's about intentionally creating a career that aligns with your values and lifestyle.

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.

Jay Coleman is a criminal defense attorney, probate attorney, Social Security attorney, and law firm owner based in Arkansas. Returning to You Are a Lawyer six years after his first appearance, Jay reflects on how his career has evolved, the realities of running a law practice, and why finding balance has become just as important as building a successful legal career.  

Lawyer Side Hustles

For Jay, entrepreneurship wasn't always part of the plan. Like many lawyers, he initially imagined working for someone else. Running his own firm gradually taught him that practicing law and operating a business require two very different skill sets.  

"I didn't go to law school planning to have my own business,” Jay Coleman expresses in Episode 254 of You Are a Lawyer.

Today, Jay spends as much time thinking about leadership, operations, and creating systems as he does practicing law. He's also intentionally working toward something many lawyers struggle to achieve: balance. Rather than measuring success solely by billable hours or case outcomes, he's learning to prioritize his own health, hobbies, and relationships alongside his growing practice. His journey reflects a reality many lawyers experience but don't often discuss openly. 

This episode is produced by Skip the Boring Stuff, a podcast strategy company for business owners and creatives.