Many business owners we’ve spoken with didn’t start with a huge team on day one. They had to learn how to be a good boss, but the problem is the books on leadership are often highly theoretical and so we wanted to hear practical examples of what it means to be a good boss. So, we asked some brilliant, insightful folks to share stories about the best bosses they’ve had.

Brett Hartong

I’ve had the privilege of working with some outstanding leaders throughout my career, but two individuals truly set the foundation for my journey in cinema and storytelling: my Creative Non-Fiction professors at CSULB, Helen Hood Scheer and Kate Trumbull-LaValle. Both were not only mentors but role models who transformed my perspective on filmmaking and life. Helen and Kate taught me that with a clear vision, dedication, and solid planning, anyone can bring their voice to the world. Their emphasis on authenticity—telling stories that are genuine and grounded in truth—shaped how I approach my own work and influenced my path forward. Being a Student Aide for both of these inspiring teachers instilled a sense of pride in me that was a turning point. It set a standard in my life, one that continually reminds me to aim higher and embrace storytelling with integrity and representation. Read more>>

Mary Gattorna

In high school I worked at a vintage clothing store in Baltimore called Ten Car Pileup. The place is so wild, like something from a movie, totally stuffed full of the coolest clothes, accessories, artwork, and random paraphernalia from every decade. There are literally tutus hanging from the ceiling. It was also a neighborhood hangout for all the artists, musicians and punks. I thought the owner, Shane, was the coolest adult I had ever met. He played music, he had worked in fashion, he made his own jewelry. He always wore his vintage Hawaaiian shirts with a few buttons open, like we lived in Venice Beach or something. He didn’t smoke cigarettes but he didn’t care if I did. I basically forced him into giving me a job by showing up constantly for maybe half a year, until he eventually gave in and hired me. Read more>>

Crystal Cunningham

Dr. John L. Graham was the most remarkable boss I have ever had. When I was searching for a teaching job, he assured me that he would remember me. Just two weeks later, he shared news about a partnership he had established at Riker’s Island. With unwavering conviction, he looked me in the eye and said, “You are a nice person; I want you to teach at the jail.” I was initially taken aback by this unexpected proposition, but I felt a strong sense of purpose to accept it. My desire to uplift and inspire those in the jails became the highlight of my teaching career. Interestingly, a few years prior, someone with spiritual insight told me I would “teach in a prison,” and I had laughed at the notion! It turns out he was right. Dr. Graham, my former boss and mentor, also advised me to always keep my circle small.

Maya Yearwood

Lindsay Vick was an exceptional leader who truly made a difference in my career and my life. She was a brilliant strategist and a skilled manager, but what truly set her apart was her commitment to fostering an inclusive and supportive environment. I was initially hired as a contractor to manage a massive global activation, and was quite nervous about how to execute at such a large scale. From Day 1, Lindsay consistently championed for my ideas, and always created a safe space for me within the organization. Read more>>

Devaughn Robinson

I have been very privileged to work with many amazing people on some very amazing projects throughout my life and through some of those times. I’ve been led by those amazing people. Space. One of the more impactful, bosses and job experiences that I had was working for my old middle school when I was just coming out of college and trying to figure out what I was going to do. The reason this was a bit more impactful for me not only is it the nostalgia of being able to work for your own school , but also the amount of support I received from that school as a child. Ultimately help pay my career. This was the same school that allowed me to bring my fellow seventh and eighth graders to a play. I had written for a student festival at Carnegie Mellon University and the same school that bought me a MacBook laptop to write a school show so the opportunity to come back was more than I could’ve deserved at that moment. Read more>>