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.

Jazmyn Bradford | Social Entrepreneur

I wanted to create a service agency that would allow community leaders (i.e. small business owners, nonprofit executives) to Focus On Their Genius behind community-based organizations. The tedious tasks in building and sustaining an operable organization can take away from the time leaders would like to work withIN the organization. Therefore, my team provides timely and quality deliverables that allow them to continue advancing their organization’s mission and/or vision. Read more>>

Mandi Rodenbeck | Owner of Great Lakes Doulas. CD PCD(DONA), Certified BRM Pro

I actually never wanted to start a business or run a business. This business found me, in a way. I was once a contracted doula under Great Lakes Doulas. In 2020, the owner came to me and told me she needed to let some things fall in order to maintain a healthy life and I asked her if she needed help with the business. I ended up buying into the company at 50% and three months later she pulled out entirely and gifted me the other half. That day I was faced with a choice I hoped never to make- to run an agency blindly or shut it down. I seriously contemplated both options and sought many opinions from friends and family and in the end decided to go for it. I officially became sole owner January of 2021 and we’ve grown exponentially ever since. Read more>>

Joseph Slicker | Car Salesman/Small Business Owner/Motivator

I have to give the credit for that to my Wife, Erin. We have always been the family to throw parties at the house either front yard or backyard. Normally outdoors so naturally, we have a lot of outdoor party games. When COVID hit and people were sent home from work, we got a lot of request from people to borrow our games. She realized that many people did not have these games of their own. Whether it was a matter of storage space to keep them or that they would seldom use them, we noticed that there was a need for small outdoor games to be rented. Thus giving birth to the idea behind Slicker’s Outdoor Game Rentals LLC. It has since expanded into Photobooths as well and I am sure we will continue to grow and add options. Read more>>

Emily Dawson and Lynette Ulman | Emily: owner | creative director | floral + event designer // Lynette: lead wedding + event planner | floral + event designer

In 2012, we were looking for something completely different from our 9-5’s. Ultimately, we both fell into the wedding industry in very different ways. Emily walked into AGE one day and told the previous owner she was willing to do any work she had! After many years of growth and establishing the name in the community, All Grand Events + Floral was sold to Emily who focused on floral design. Read more>>

Kina Renee | Owner & Artist

Starting SeeTheGurls was like planting a garden of appreciation for the amazing women and girls in the entertainment industry. The idea sprouted from wanting to give a bunch of virtual flowers to those who rock but might not always get the recognition they deserve. So, consider SeeTheGurls a cheerful space where we make sure these fantastic individuals are showered with appreciation and applause for their awesome contributions to the entertainment world! 🌸✨ Read more>>

Robert Onnes | Sculptor

Having decided to pursue sculpture, only self employment was an option. I prefer the flexibility of being my own boss Read more>>

Rob Devroy | Creative Director + Founder of Capture Video + Marketing

Right out of college I did freelance video editing and animation. I enjoyed the freelance aspect of it – the ability to work on my schedule and be my own boss. But I wasn’t very good when I started! Read more>>

Jesse Palter | Founder (and Chief Dreamer) of Tunez 4 Totz

Tunez 4 Totz was a happy-accident of a business venture that started during the pandemic in 2020. Amidst the upheaval caused by canceled tours and gigs as a recording artist signed to a label, I found myself facing a halt in my musical journey with no clear path forward. However, when a close friend proposed the idea of sharing music with her baby’s “pod,” I had no good excuse to say “no”. Living in Los Angeles, where outdoor activities were viable year-round, I embraced this Covid-safe opportunity to engage in something meaningful outside my confined space. Stepping into that first session, I experienced an immediate revelation—an “aha!” moment. The realm of children’s music felt like a wide open door, brimming with unbridled joy, endless wonder, and boundless inspiration. This newfound world sparked my songwriter instincts, igniting a fervor to craft music tailored for families. I delved into studying child development in relation to musical education, forming the bedrock for my own approach to early music exploration, discovery, and education. It was a transformative period where my creative energies converged with a passion for nurturing young minds through the language of music. Becoming a mother myself offered additional perspective. As I navigated the intricacies of new parenthood, bonding with my little one over musical exploration became an integral part of our connection. Experiencing firsthand how to captivate and communicate with my child over music deepened my appreciation for it’s transformative power in early development. This personal evolution not only shaped my approach professionally but also amplified my commitment to creating a magical, nurturing and enriching musical environment for families through Tunez 4 Totz. Read more>>

Angela Wascher Lisa Gravlin | Co-Owners of City Bake Shop LLC

We (Angela and Lisa) had dreams of starting our own independent businesses, but after working together professionally for 3 years and becoming close friends, realized we could start a successful business together. We were both faced with major career changes, and took the opportunity to create City Bake Shop. Our individual skill sets compliment each others strengths and weaknesses in a way that benefits the growing venture. Read more>>

Ryan Hudson | Event planner in the entertainment space and lover of hard working creatives.

My venture into my current entertainment business started as a completely different industry, out of pure necessity.

Once upon a time I earned a living repairing consumer electronics for a very well-known and large company based in Massachusetts. I soon went into a mechanical design role and after business closer or relocation, I was offered a “work-from-home” option that bred the idea of opening my own mechanical design firm. Read more>>

Carey Gustafson | Stained glass artist & instructor

It was a natural progression from my childhood! My very favorite things growing up was arts & crafts, drawing and portrait-making, and coming up with sales opportunities as early as 10 years old! For anyone that’s known me from back in the Nineteen Hundreds, my career choices and path would be no surprise at all.  Read more>>