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.

Whitney Weathers

In 2022, a white man walked into a Supermarket and opened fire on its Black customers; that shooting claimed 13 victims. Could you sit with that sentence for a moment? While I would like to think that we are somehow desensitized to all of the shootings and killings, we are not. Let me not speak for everyone–I am not. Read More>>

Porscha Bailey

The best boss I ever had was, paradoxically, one of the most difficult leaders I’ve worked under. From 2023–2025, I accepted a position serving an underserved community with genuine enthusiasm and a strong desire to make meaningful impact. I came in committed, innovative, and driven to elevate patient care and team performance. What I encountered instead was leadership rooted more in insecurity than collaboration. Read More>>

Ali Alawlaqi

I once had a boss named George who shaped the way I work and think to this day. Sales is usually an individual sport, everyone is focused on their own numbers, their own pipeline, their own pressure. But George had a way of making you feel like you weren’t doing it alone, even though technically you were. Read More>>