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.

Kate Jones

In 2012 I was living in Los Angeles and had just left a retail job. I saw an ad in Craigslist for an assistant to a clothing designer and I answered it. I met Jesse Kamm in a coffee shop and thats how I started working for her. It blossomed into nearly 9 years. At first it was part time, but we grew together. Read more>>

Vicky Thompson

I have been blessed to have some amazing bosses in my lifetime. But the best boss I ever had was one of the first bosses I ever had. Hard work was drilled into me from a young age but it was Cathy English who nurtured that work ethic by recognizing and rewarding it. Read more>>

Dr Jacqueline Mack-Harris

Vicki Geisler is the best boss that I have ever worked for. She employed me as the director of nursing for her home healthcare agency. She is a retired nurse who started her business in the 4th bedroom of her family home. She often shared stories about her journey from becoming an independent home health nurse to an entrepreneur. Read more>>

David Emmanuelle Castillo

To be totally transparent, this person may probably be bothered that they came to mind when a question was posed with the word “boss” in it. However, LaNelle Ramey is a total boss, and I mean that in the Jay-Z 2nd verse of “Boss” type of boss. Like myself, LaNelle was part of the founding team of the Department of Black and Latino Male Achievement (BLMA) for Milwaukee Public Schools. Read more>>