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.

Shelly Kelnhofer

My best boss…MY BEST BOSS…my friend, Scott.
I was working at a high end restaurant, but kept going to the local “burger place” down the road. It was a small place, not many workers, but everyone was always in a good mood, seemed to be having fun, and the food was fantastic.
I would hang out just to talk, and kept joking about having a job there. One day the boss/owner offered me a place with the crew. Read more>>

Regina Mcmenomy

My video call notification rang immediately after a meeting ended. It was my new boss. She was in the meeting that just ended. My first thought? OMG what did I say wrong. “Hey. What’s up?” I asked, a small shake in my voice as my emotions betrayed me. “Is it just me or does she hate everything I say?” I laughed, knowing exactly who she was talking about and having an intimate understanding of this coworker’s unique ability to make you feel like the sludge on the bottom of your coffee cup. Read more>>

Justin Giordani

During college, I worked as a lease specialist for an apartment complex, and my boss at the time had a profound impact on the way I viewed leadership and work. She had a unique ability to empower her team, fostering an environment where people felt valued and motivated to go above and beyond. Through her encouraging words, thoughtful guidance, and generous gestures, she created a workplace culture that inspired excellence. Read more>>

Katharina Boger

The best boss I’ve had in the music industry so far has been myself. If possible, I would advise everyone to become their own boss because it gives you more freedom, freedom to make your own decisions about which songs to record and release, which jobs to take or decline. The ability to create without someone telling you what to do is the best thing you can achieve. Of course, it’s important to stay open to working with other companies in the music industry, making deals, and continuously gaining experience. This helps you understand what’s possible and who you need on your team. Read more>>

Ashley Chamberlain

My amazing boss story goes back to my first official job as an accountant for a local transportation company. This boss, my now father-in-law, changed the small business game for me. He showed me how to treat people and never forget that they are the center of everything. The relationships you build with your employees, business referral partners, customers or clients are what should drive you every day. Treat people with decency and kindness, and business follows. Read more>>

Candace Jordan

Hands down, the best boss I ever had was Hugh M. Hefner. He literally brought me to the party. He invited me to move to Chicago into the Playboy Mansion from my work as a Bunny at the St. Louis Playboy Club. From this point on, there was no stopping me. I became Chicago’s Playboy Bunny of the Year, a Playboy centerfold and 9-time cover girl. Hef, and Playboy, have been very, very good to me and I’m proud to still be an ambassador to this day for Playboy. Read more>>