Readers often email us asking us for advice about new businesses they are thinking about starting and we often find that many of them don’t have a framework for thinking about a more fundamental question: why should or shouldn’t you start a business?

Below, you’ll find how successful entrepreneurs from across the city thought about this very question when they were considering whether to start their businesses.

Margaret Tolbert

I started Tolbert Marketing and Events because I love what I do, I love the people I work with, and, honestly, I wanted to build something that felt true to me. Marketing has always been my passion, but even more than that, I thrive on relationships—connecting with people, helping businesses grow, and making an impact.

After years in the industry, I saw a real need for marketing that wasn’t one-size-fits-all. I wanted to create a business that focused on personalized, results-driven strategies while still being fun and approachable. I didn’t want to be just another agency—I wanted to be a true partner to my clients. Read More>>

Kelly Chapman

I started my business 10 years ago. At the time, I had dropped out of college and was a stay at home to two babies 2 and under. I had always loved photography, but had never considered making a career out of it. It was the birth of my first daughter that really lit my passion for it on fire. I wanted to capture every milestone and freeze time somehow. So I began teaching myself through trial and error. I studied, watched countless tutorials, made all my friends model for me, and went through all the growing pains that come with finding your unique style. But even then, I could not imagine people paying money for my work.  Read More>>

Zachary Holcomb

I began my insurance career after faithfully serving in the United States Marine Corps. My extensive background in claims began while working on a catastrophic response team for American Family Insurance covering each part of the United States responding to wildfires, hurricanes, tornadoes, floods, mudslides, and environmental disasters. Additionally, I’ve served on complex large loss ligation teams handling the most difficult cases over the years that were settled at the state, circuit, and appellate levels. Read More>>

Montae Harris

My goal has always been to create a business to give back but also something I enjoy doing. So with the podcast, it’s much more than conversation, it’s about creating a platform for others to share their talent and their story. I want to create the next breakfast club of media. So once I realized I was officially done with sports, it was time to tap into my next talent. Read More>>