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.

Nick Matarese | Agency Owner & Creative Director

Taxes. Originally I started this business for no other reason than accounting. While still at a small section of adidas, I went and got an LLC because I was doing too much freelance work on the side and was worried of getting audited. Read more>>

Christa McConnell | Owner, Christa McConnell Photography

Having my own business is something I always wanted to pursue. While I was in school I had all these projects to brand yourself, and I always took them very seriously, I wanted to be my own boss and make this work. When I graduated, I had the space to give it a go. I built up my portfolio and started the process of refining who I was as a photographer and what I was going to photograph. These early days were hard, but I loved it! Having my own business lets me have the flexibility to photograph what I want and how I want. I feel like I can give my clients exactly what they want. I love photography and I love getting people excited about photography. Having my own business lets me share my passion for photography with others! Read more>>

Elaine Pofeldt | Independent journalist, author and speaker

I started my own business as a freelance writer and editor when I had three children under the age of four, including twins, and realized that even a very flexible corporate job was not flexible enough to accommodate the constantly changing needs of my family. At the same time, I wanted to continue working at a very high level–I had been a senior editor at Fortune Small Business magazine in the Fortune Group at Time Inc.–with colleagues I enjoyed. And I suspected I could do so, and still be a very present mom for my children, if I had full control over my schedule. That was in Oct. 2007, and my decision to start the business turned out to be one of the best I’ve made in my life. My business expanded beyond what I even envisioned, even as my family grew to four children, and I have branched out into areas I did not expect, such as content marketing, ghost writing and editing books for clients, and writing two of my own books “The Million-Dollar, One-Person Business” (Random House, 2018) and “Tiny Business, Big Money” (W.W. Norton, 2021). It’s been exciting to see the new opportunities that have opened up as a result of sticking with the business for a long time. Read more>>

Glen Coy | Owner

I opened a skateboard shop when I was a senior in high school way back in 2000. During the 17-year run of the business, I noticed a massive void in the custom garment printing industry in our area. In 2015 I bought a small screen printing press for $3,000, and hired someone to teach me how to use all of the equipment. We set up it in the back of the skate shop, and quickly had things up and running. Read more>>