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.

Alexis Conerty | Florist/Floral Designer

The thought process started before I even knew that I wanted to own my own business. I Worked for a grocery company for about 14 Years. It was my first job. I Started From the Bottom bagging groceries and pushing carts then worked my way up until I became a store manager. I managed Not only 100 people in the building, but thousands of customers as well. I started my own Family during my career or what I thought was my career. I have three beautiful boys during my time there and I was still putting everything I had into my job as well as my family, and I was stretching myself extremely thin. I then lost my job that I worked so hard for. Read more>>

Jules Gonzalez Samperio | Small Business Owner | Content Creator

The decision to start my own businesses was inspired by observing my father and younger sister take the leap into entrepreneurship and witnessing their subsequent success. My father has dedicated over two decades to his pool service business, while my sister has achieved nearly two years of growth in her nail business. After thoughtful consideration, I made the bold choice to leave my 9-5 job and pursue three distinct business ventures. I was prepared for change, eager to confront challenges, and committed to continuous learning. Read more>>

Natalia Favela | Founder

Honestly starting my own business started off as as an accident, it was something on the side that I did for fun! At first I would just show up whenever friends would need a bartender, but I quickly realized I had a passion and excitement for event planning and crafting up cocktails. I had no prior experience in business but I learned everything as I went along and was able to figure it out during my first year. I never imagined Bloom to take off like it did, I’ve had fully booked out months to the point i decided to expand and purchase a second bar as well as hire employees in order to fulfill more event inquires. This has been such an exciting year and its amazing to look back at all Bloom has accomplished. Read more>>

Erna Van Dyk | Visual Artist & Art Instructor

My passion for art making and for teaching art made this a perfect fit for me. Creating art is healing and also forms such a great community. I needed that so much and I feel so lucky I can give this opportunity to other people. Read more>>

Jean Sharony | Commercial Producer & Owner of Whisky Films

The decision to start my own business was driven by a mix of passion, necessity, and the desire to take control of my creative vision. Coming from Chile, where I began my career in commercial production, I had always been drawn to storytelling. When I emigrated to the United States nearly 20 years ago, I quickly realized that the production processes here were very different from what I was accustomed to in Latin America. This presented both challenges and opportunities. Read more>>

Carly Johnston | Co-Owner Weekend Vans

Weekend Vans was born from a desire to make camper vans that were both affordable and family-friendly. After dealing with unreliable VWs and not wanting to take on a second mortgage for a van, we decided to build our own. Our goal was simple: create a reliable van with everything you need and nothing you don’t—perfect for daily driving and weekend adventures. Read more>>

Sophie Williams | Artistic Director & Ballerina

The idea of starting Pointeworks came from a desire to create more opportunities for dancers and artists, especially during the off-season. So much talent can go unnoticed or be underutilized outside of the main performance schedules, and I wanted to change that. Another driving factor was the importance of highlighting female voices, which are often underrepresented in the dance world. I saw a gap in not just gender representation but also in the innovative and cutting-edge ballet performances that could captivate and challenge audiences. Read more>>

Gregory Jones Jr. | Illustrator, Film Critic

I knew that I loved creating all kinds of art including fan art. I was always envious of people who sold their work at conventions and after some thought (and a pretty big push from loved ones) I decided to take the plunge and give it a try. It was very rewarding in the end! Read more>>