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.

Jayson Benjamin

The best boss I ever had would have to be my parents. They were not only my parents but also my first “bosses” in life. I believe that parents are usually the first authority figures we have to listen to, long before we step out into the real world. They taught me to be kind, honest, and always treat people the way I want to be treated. My parents’ guidance shaped how I approach life and work, helping me learn how to adapt and behave in different situations. Read more>>

Jose Pinky

Well yes my current boss actually her name is vane , funny story I’ve known her since 2006 she was my boss then at a boutique we worked together , we lost contact after we parted ways from the store, so couple of years later I worked for the same boutique again and her mom was a client of mines and vane had her own boutique , so I told her mom tell vane I say hiiii, long story short vane contacted me and basically dragged me to work for her which I ran , so i became the manager/stylist of her boutique store , but after the pandemic she shut the store down and she took me in to be her stylist and creative director for her online business , she’s just an inspiration the way she leads her business and has so much love and creativity which inspires me, she’s taught me a lot in life and fashion, not only is she my boss but she’s also family my best friend . Read more>>

Jordan Danielle

When I was in high school, I had a photography teacher named Bill Kovnat. He taught me skills that I never knew I could achieve and made me look at photography as a profession rather than just a hobby. Who would’ve thought he would recognize something in me and decide to hire me? Bill took me under his wing when I was 18 and fresh out of high school. He also introduced me to his wife, Chrissy, who is his sidekick and business partner. My first job with Bill was working a wedding and it was incredible to see him in action. He is one of the most charismatic people I have ever met and draws in a crowd like no other. Read more>>

Devan Skaggs

I had a long-winded response prepared for this question where I’d get to drop a big music industry name from my past but it doesn’t resonate as the truth to me any longer. The real answer is that I am the best boss I’ve ever had. All my life I wanted to be my own boss. No one else could ever know how to challenge me in the right ways, how to coax the results I want to see out of myself or how to walk the very particular path that I carved for myself. I had to figure that out; am figuring that out. At least now when I’m too hard on myself or not hard enough, I only have myself to answer to. I prefer it that way and I’m pretty sure all my former employers would agree it’s for the best haha! Read more>>

Rosario Castorena

My first job after graduating from CSULA was at the trim manufacturing mill Labeltex, I was the sales assistant for the Sales Executive Stephanie Huerta. I had my share of bosses before, but Stephanie stood out to me more than all. She always made sure to thank you for my work at the end of the day, such a small gesture to some but it made me feel appreciated. Even though she was in sales she was never pushy, she made all her clients feel important even her smaller accounts. They all received her utmost attention, no one was made to feel less than. Read more>>

Emine Avanessian

The biggest influence on my life and the first person I ever worked for was Johanna Went. She is an incredible performance artist who was legendary in the 80’s punk scene in Los Angeles, but that’s not the context I met her in and I didn’t learn this till later. In the 90’s she had a beautiful line of silk screened pillows that my mom’s tiny garment company sewed, and she’d always come by to drop off silk fabrics, wearing her skull scarf and just being so cool. After hanging around a lot and talking to her, she offered me a job helping her silkscreen and tidy up around her studio down the street, which was just pure magic.  Read more>>

Kristine Bautista

My journey with Dr. Francesca McCartney at the Academy of Intuition Medicine® was a defining chapter in my life, marked by her extraordinary knowledge, guidance and leadership. Unlike any other teacher and mentor I had encountered, Dr. McCartney’s nondogmatic approach redefined my understanding of health, healing, and myself. Read more>>

Tyne Stecklein

I’ve been very fortunate to have worked for some incredible artists over my career. The best “boss” I ever had was the one and only Cher. I was chosen to dance for her residency at Caesars Palace in Las Vegas back in 2008. I then went on to act alongside Cher in the film Burlesque, and tour with her on her D2K tour. What made her so amazing to work for was how thoughtful she was of her entire team from the band, dancers, production crew, and so on. After a year at Caesars Palace I left the show as I wanted to explore new opportunities in my career. I was still invited to dance with her again many times after that in the coming years because of the respect and loyalty she had to the artists on her team. She is such an icon, and yet she’s so incredibly down to earth, funny, and caring, and this taught me at a very young age (I was 20 when I started dancing for her) how to remain humble and human no matter your level of talent or success. Read more>>

David Rodriguez

The best boss I have ever had and still have is Kyle Parker, CEO and founder of ClipDart. Not only is he revolutionizing the hair industry that I am a part of, but he’s also revolutionizing all hair professionals that participate in the events. Through his traumatic experience while attending Grinnell College in Iowa by not having access to a barber with coarse hair texture knowledge, Kyle Parker has made it possible for many marginalized communities to receive free haircuts via selfless mobile barbers and stylist. Besides making history in the hair industry, Kyle has taught me more patience, professionalism, understanding and business IQ. He’s also trusted me with certain responsibilities which allows for my personal and professional growth and development. One of the best things about working with Kyle is that we learn from each other because we both have the same mission and passion for our communities. Read more>>

Tiffany Naccarato

Having a great leader or mentor can be life-changing, and for me, Becca Brown has been that person. From day one, Becca has rooted for me in ways I never expected. She never doubted my potential or made me feel like I couldn’t achieve something, no matter how challenging the goal. Instead, she always worked with me to figure out how to overcome obstacles. Together, we would find a way, one way or another, to make things happen. Read more>>

Michael Neece

Jim Horn at Morehead Planetarium was easily the best mentor I’ve ever had. When I started working at the planetarium, I moved into management within 12 months and started working closely with Jim. One of the other students in our care wasn’t acting appropriately, having talked to an audience in a depressed tone about personal things.  Rather than look at the situation and say he needed to be fired, Jim asked questions about the student. “What’s going on outside of work?” He taught me in this situation, and in many other, that the humans we work with are, well, human.  Read more>>