We were lucky to catch up with Robert Cherry recently and have shared our conversation below.

Robert, looking forward to hearing all of your stories today. Looking back at internships and apprenticeships can be interesting, because there is so much variety in people’s experiences – and often those experiences inform our own leadership style. Do you have an interesting story from that stage of your career that you can share with us?

When I was in law school in Vermont, I spent a decent amount of time scouring the internet for internships and summer clerkship opportunities. The legal market is competitive, especially in the arts and entertainment space. And with summer approaching, I was feeling pressure to secure a summer clerkship and an internship for the following fall semester.

After spending countless hours searching and sending what felt like 1,000 emails, I stumbled on an anonymous Craigslist ad for a legal admin role at an art and fashion law firm in Los Angeles. The ad was vague, offering little more than a description of duties and qualifications. However, it was enough to spark my interest and know that the firm was looking for help. So, I googled various words and phrases from the ad and unearthed the firm’s identity and managing partner’s email. The firm was a small but reputable practice in Culver City that (unbeknownst to me) would soon relocate to a few blocks from the beach in Venice.

I sent an email to the managing partner, attempting to showcase my skills and express my enthusiasm. Within minutes, I got an email notification on my phone. It was the partner, impressed by my initiative and willing to learn more about me. A phone interview was set for the next morning.

The interview went well. The partner appreciated my approach and eagerness to learn. The firm offered me an internship for school credit in the fall, but summer remained uncertain. I was undeterred, so I booked a flight to Los Angeles.

Once in LA, I reached out to the firm, explaining that I was in the area and would love to introduce myself in person. I also mentioned needing some paperwork completed for school, a clever guise to get my foot in the door, and the partners agreed to meet me.

Walking into the office, I was nervous. I was a guitar player moonlighting as a law student and couldn’t have been more uncomfortable in a tucked in shirt and slacks. After exchanging pleasantries and discussing the paperwork, I seized the moment to pitch myself for a summer job, and they were still undecided. As I left the office, I knew I had made my case and that it was now up to them. Before I made it down the street, my phone rang. It was the partner, offering me a paid summer position.

Ten years later, I still work with the firm.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I am a business and intellectual property attorney located in Texas, and I maintain a license to practice law in Texas and California. My contemporary, context-sensitive approach to providing legal services, as well as the care that I exhibit for my clients, sets me apart as an attorney for start-ups and established businesses alike.

I handle startup and founder issues, mergers & acquisitions, contract drafting and review, federal and state securities law matters, capital raising for small and medium-sized businesses, copyright litigation, and outside general counsel services. I serve clients in the arts & entertainment, hospitality, technology, agriculture, and manufacturing industries, and I strive to help clients achieve their business goals and manage legal risk.

In addition to the law, I’ve been a dedicated working, recording, and touring musician since 2006. My work is featured on various films, television shows, and advertisements and has accumulated millions of plays on streaming platforms. I’ve toured extensively domestically and internationally.

Have you ever had to pivot?

My journey has always been a delicate balance between jobs and music. From when I picked up my first guitar, music was my passion. And for years after undergraduate school, I focused heavily on music, just keeping odd jobs to make ends meet. Eventually, the idea of a more stable future led me to law school.

During law school, I managed to balance the demands of law school with music and touring. And after graduating and stepping into my role as an attorney, I continued to make time for music. Weekends and evenings were filled with rehearsals and gigs, and I’d make time for a few tours every year. For a while, I had the best of both worlds.

As years went by, and my music career reached new heights, I found myself playing with the best bands I had ever been a part of. And I was making music with people who were more than just bandmates, the relationships were special. The recognition we received was a testament to our years of hard work pursing music. But as the momentum of my last band gained, so did the demands of my law career. And then, life threw in another factor—the need to be present at home with my family.

It was a gradual realization, I started noticing the strain of late-night gigs and long rehearsals on my ability to be fully present at work and at home. The balance I had once maintained so effortlessly began to wobble. I was an attorney, a musician, a husband, and something had to give.

The decision wasn’t easy, and the conflicting emotions were evident in my voice when I explained to my bandmates that I had to step away. I was leaving behind more than just music; I was leaving behind a part of myself and a group of friends who had become family.

The first few weeks after stepping back from the band were tough. I missed performing, the camaraderie, and the creative outlet that music provided. But as time passed, I found a new rhythm (lol). My focus shifted more towards my legal career and my family. The steadiness of law provided the stability my life needed, and being present at home brought a new kind of fulfillment.

I continue to play music, but now it’s more for personal enjoyment than professional pursuit. And I no longer look at my pivot away from music as an end, but more like a transformation. My life is more grounded, and there is a lot of happiness in the stability and deeper connections with my loved ones. This shift allowed me to grow in ways I hadn’t anticipated.

Can you tell us the story behind how you met your business partner?

Out of law school, I landed a job at a transactional law firm that, on the surface, seemed like a promising start to my career. I had a sleek, modern office, filled with a lot of glass and light, it felt like “success.” However, beneath the surface, I had my doubts. The firm’s book of business seemed sparse, and the environment lacked opportunities for learning and mentorship. But despite the bad stuff, I was still learning and my office made the daily grind a bit more bearable.

Then, one day, my boss dropped a bombshell. He informed me that my prized office had been rented out to another attorney, and I would now be sharing my boss’ office. I was also informed that my boss rented me out to the new attorney too. I was not excited, to say the least, and it felt like a step backward.

The new attorney arrived, and I was prepared for the worst. But when I met him, I was pleasantly surprised. He was funny, approachable, and had a genuine enthusiasm for the law and doing good work. He quickly became my mentor, and I was able to leave that job to collaborate with him more closely. Over the next seven years, we worked together growing his practice. Meeting him turned out to be one of the best things that’s happened to me professionally, and the success we’ve built together (and the knowledge I’ve gained) is a source of immense pride and fulfillment.

Contact Info:

• Website: https://www.rcesq.com/
• Instagram: https://www.instagram.com/hilo_rc/
• Linkedin: https://www.linkedin.com/in/robert-cherry-6b8bb164/