Are you thinking about starting a business? If so, we think you’ll enjoy reading about how these seasoned entrepreneurs thought about the question when they were in your shoes.

Madhurya-lila Roe | Vegan Baker & Owner of Lila’s Sweets

I’m pretty sure it’s in my blood. My dad worked at Pfizer for most of my life but always had side projects going–mostly working on custom motorcycles, fixing up antique cars and repairing anything with a motor. Around 50, he left his day job and opened up his own motorcycle shop in the small town I grew up in. Even then, he kept other side hustles going–from running a hot dog stand in a nearby state park, to selling high-end guitars on Ebay, to auctioning off his Red Sox season tickets for home games he couldn’t attend. Read more>>

Katy Girlinghouse | Doctor of Physical Therapy

I started The Fit Pelvis because I was seeing that patients were not able to get the care they needed and would benefit from due to insurance limitations. When I worked for a hospital based system I had patients get denied care for pain with sex or for postpartum recovery. I also wanted to practice what I teach my patients. Balancing work and family, exercise and joy improves your nervous system function, can improve sleep, anxiety and stress, help with weight loss and reduce pain levels. Read more>>

Alan Porter | Graphic Designer & Gig Poster Artist

Stop working in things that didn’t make me happy and I wanted to begin working on things that inspired me to be a better designer. Read more>>

Kat Masley | Artist & Writer

It was less a thought process and more a result of COVID and job loss. I also wanted to do something that would keep my mind sharp and make me creatively happy. I started messing around with some old photography, re-teaching myself Photoshop and Lightroom. I’ve long loved Etsy and always wanted my own shop, but never knew what to sell. In my head I toyed with the idea of offering my own photography, but I didn’t feel any of my shots were good enough. Read more>>

Noree Victoria | Actor-Writer-Director-Creative Producer

I was born into a family of entrepreneurs. Back in Baltimore, from childhood, I watched my family build candy stores, restaurants, real estate holdings, home improvement businesses, and more. I was born into the pedagogy that self-sufficiency is the ultimate goal, and that there’s no sacrifice more noble than making an attempt to take charge of your family’s future. My dad led that charge for us. I grew up watching the wins, losses, triumphs, and long-haul marathons of people who knew what it meant to gamble on oneself in the face of everything from recessions to discrimination. No matter the odds, every idea you had followed with incorporation, an accountant, and an attorney. Read more>>

Robin Ware | Licensed Esthetician

I’ve always had a passion for skincare and the beauty industry since childhood. I had problematic skin growing up and was always searching for the best remedies to care for my skin and keep it healthy. At a period in my life as an adult, I was at a crossroads as to what career path I should take. Never losing my strong interest and desire for skincare, I decided to take the leap and pursue my dream of becoming a licensed Esthetician. After many years of working where I provided my professional services under other people’s businesses and strong encouragement from my mother, I decided to take a leap of faith and venture out on my own. Read more>>

Carol Roullard | Photographer, Painter and Writer

I started in one direction, writing photography-related books and ended up with a totally different business that has evolved and pivoted several times with the changing business environment. Through this all, my motivation was to have a business that I enjoyed and would use my creative side. Read more>>

Michelle Adams | Owner of Sex Fox & RocknRoll Productions, Director, Producer, Writer

Honestly, my thought process in starting my own business was that I did not want to continue to work for someone else. I wanted to get into a business that was both creative and artistic yet I could tell my stories through documentaries involving music and other artistic individuals. Once I started my production company Sex Fox & RocknRoll Productions, LLC, I knew I wanted to do a rockumentary (as I call it) about one of the MOST talented musicians in the world and that is Stoney Curtis. Read more>>

Chris Van Vliet | TV Host & Podcaster

I was always dumbfounded by the idea that if you a job with a salary, you get paid the exact same amount whether you work your ass off or barely do enough to get by. I never thought that made any sense. So I took the things I was passionate about and looked for ways to monetize them. We’ve all heard the old adage “Do something you love and you’ll never work a day in your life”. As cheesy as it sounds, it’s true. While you are still working every day, you’re working to grow your own business and there’s something that is uniquely fulfilling about that, especially when you are surrounded by people who also love what they do. Read more>>

Chatiera Cookie” Ray | Executive Creative Director of the CRayProject”

I really wanted to start something that was inclusive to me and others that look like me. Being a brown curvy woman that dance, has been a struggle. Being a dancer professionally and classically trained in ballet and modern dance, there were not a lot of spaces for a woman of color of my stature. I was only landing hip-hip dance roles (if that), and I knew I was capable of doing more. Read more>>

Dylan Vartikar | Multihyphenate, Designer

My ultimate north star has always been a career as a multi-hyphenated designer and artist. My design venture, SaBo (formerly Saison), is two-pronged: first, I consult for various clients and companies on an array of design work and creative direction. Second, SaBo is a safe space for exploring visual communication and creative research. In this way not only can we collaborate with others on design work, but also explore various aesthetics, creative avenues, and mediums. This year, we started our journey in interior design. Read more>>

Chanté Linwood | DJ, Artist & Boy Mom of 3

My whole life I knew that working for other people was not for me. I always felt as if I had great ideas, ambitions and/or goals and I was rarely understood, let a lone supported. Growing up in an area devoid of most skin colors, I was treated poorly for being brown skinned and black. I was often degraded, excluded and discriminated upon so I am no stranger to this treatment and often thought of ways to cope. Read more>>

Lex Casciato | Founder of Visitor Records Music Label

I got really tired of hearing “this is how it’s always been done…” when how “it’s always been done” isn’t working for music creators (artists, songwriters, producers, engineers, etc). I found that statement to be so uncreative and lacking innovation, so I decided to start my own music label run by artists with the goal of revolutionizing the music industry and helping artists get heard in a loud world. Read more>>

Alexis Simpson | Actor Who Writes

I’d have to say that the thought process behind starting my own business was “No thought process.” I wasn’t one of those people that always dreamed of being an actor and, in fact, I didn’t even realize that acting was a job you could have until I was in my 20’s. I think that I just always assumed that the people on TV lived inside of the TV, somehow? Anyway, I went to college like a Good Little Student and majored in Neuroscience, with intentions of going to grad school. After college, I worked in a neuroscience lab at a major university. Sure, I was performing comedy several times a week, but I really thought I was going to get a PhD. Read more>>

DRACINC | DONN THOMPSON | Fashion and Beauty Photographer

I worked as an assistant for many Big-named photographers from back in the day. I made them look good and fixed their fuck ups or did lighting for them. So why could I not do it for myself and go after a big paying Photoshoot? Read more>>

Jane Owen | Publicist

I have always seen PR as a way to help people, companies, projects and more, get the attention they want and deserve. To be heard, and to be seen in the best light. I was always being pushed to take on clients just because of the money they could pay rather than the quality of their product or the kind of person they were. I opened my own company with the motivation to be able to (sometimes) do the work because I wanted to not just because I had to. Read more>>

Zhe Scott | The SEO Queen

I started my own business because I saw a need. I saw that black owned and woman owned businesses were not getting the support that they needed to dominate their niche on search engines. I wanted to help leverage my understanding of technology to help them forge ahead. I addition I saw what I could do for other businesses, and I built a book of business worth $500,000 in recurring revenue in 2 years, and I wanted to do that for myself and others. Read more>>

Jordan Carey | Artist & Designer

I was studying to be a fine artist at the Maine College of Art and Design, mainly in the medium of drawing. I was passionate about making art but felt that many of the “nonartist” people I was surrounded by were not. Coming to terms with this was challenging for me because even though I loved art, the professional art world, as we commonly think of it today, has a long history of prejudice and discrimination, especially when it comes to women and people of color. Therefore, I wanted to find a medium that could better host the concepts I was working on within my art so that it could better engage with the people I wanted it to. On my next trip back home to Bermuda, I was humbled by all of the creatives I had never fully appreciated. Read more>>

Luis Zuleta | 3D Artist & Owner of Above the Clouds

In starting up my business, Above the Clouds, my thought process was fairly simple, I just wanted to create dope artwork and create some amazing things with other inspired creatives. In creating 3D prints and collectible figurines, I already had the background in modeling in 3D from my “day job” as a 3D Artist. With my love for physical artwork like collectibles and paintings, etc. I would regularly attend art shows and art conventions such as Comic-Con and DesignerCon. I was already submerged in that world as a fan for years. Read more>>

Dan smulovitz | Chef

I feel that my own business gives me more control and allows me to be really independent Read more>>

John Pene | Actor

When it came to acting my thought process came from being in a place in my life where I was tired of settling for what is safe and comfortable, and embracing my desire to be bold and bet on myself and pursue an art form that makes feel complete, alive and free. I want to go after the dreams I had since I was child. dreams that exist in my heart but that I overlooked for so long because I was afraid I wasn’t good enough to make them come true. But after years of living the “Right Way” or “normal way” it was evident to me that Acting is what I was born to do and I love myself enough now to give myself permission to go after it. go after my happiness. Read more>>

La’Quila Fields | Prosthetic wig maker/ Custom wig maker

To assist individuals who are experiencing hair loss, and to stand by the everyday woman/children to see beauty,potential and identity from the inside out Read more>>

Shaun Hamilton | Customer service technician

In 2006 I worked for a company in the city of Santa Monica, CA. That winter I was laid-off and it forced me to look to change. It was a blessing in disguise. A good friend of mine who owned a limousine service knew I was going through hard times and offered me a managerial opportunity.This gave me the epiphany to become an entrepreneur and create my own financial stability. Read more>>

Ryan Nguyen | President of Operation Be Kind Westminster High School Chapter

Operation Be Kind is a nonprofit organization dedicated to providing smiles for underprivileged individuals. I have volunteered with them since I was thirteen years old, to which I am now eighteen. Through my five years with the organization, I learned how helping others fulfills oneself greater than so many things. Inspired by founder Jeanine Rountree, my sister and I decided to open up the first high school chapter here in Westminster. Driven by the immense fulfillment, my sister and I wanted to provide the chance for our peers to participate in these sorts of events as well. We had the privilege of our teen years being filled with compassion, and we wanted to open these amazing acts of humanity to our peers, Read more>>

Joey Courteau | Artist, Actor and Free Spirit

Well that’s an interesting story that I will sum up as succinct as possible. It all started with a trip to South Dakota to a place called Bear Butte. I was going there to do my Hanblechia ceremony which is a Native Indigenous rights of passage where you fast four days and nights with no food or water. I was with a small group of people who I had been participating in Inipi’s “sweat lodges” and other ceremonies with for a few years. There was a fire and Inipi lodge set up at the bottom of the mountain to purify people going up on the hill. I was taken into this lodge and after a short purification ceremony taken up to a spot on Bear Butte. Once there a small natural alter was made with stones and I was placed within this circle. Songs were sung before they left then they all walked back down the mountain leaving me alone for the next 4 nights. Read more>>

Darian Washington | Mom, Founder & Bad Ass

I started this business because my baby loves oatmeal. I was just looking for a quick and easy way to nourish him. Initially, I had intended for this to be a side hustle, just something I could do on the weekends that would bring extra money for fancy family vacations, and a nicer car. But shortly after applying for my LLC, I was laid off from my cushy corporate job, and two weeks later I found my husband in our home with another woman and immediately put him out. I was in an existential crisis, and acutely depressed, pushed out of control and now free falling into darkness. It’s like holding your own world in your hands, and watching pieces of it blow away every single time you exhale. Read more>>

Charles Nwokolo aka Young Dick Tiger | 84’ Olympian, Former Pro boxer, Coach and owner of Tiger Boxing Gym

From age 13, when I switched from soccer to boxing, I always knew that boxing would inform the rest of my life. When I married my late wife, Patricia, we made a plan: I would continue my pro boxing career until age 41 and she would study to become a doctor and we would raise our children together. After my pro career I planned to open a boxing gym. But everything fell apart when she died suddenly of a brain aneurysm in 1997 at age 30. I was left all alone with my 11 year old son, CJ, while my younger son, Emeka, was in Nigeria. I was so devastated for 2 years that I had to leave boxing and just care for my son, who helped me to survive. Read more>>

Brett Pemberton | Owner of Music Production Company Prophecy Productions

Singers are not often taken care of in the way that they could be. Often in early stages of their careers, they lack guidance and support, so we at Prophecy Music Group help provide not only world class music production & writing, but we take the next steps with them to help build their entire teams: finding a label, publisher, management team, agent, attorney, touring, you name it. This way the artists can save years of stress and potentially missing their dreams, and fast-track it to greater impact. Read more>>

Marina Shiferman | Realtor and Real Estate Coach for Women

I have been a realtor for the past 10 years. I have helped thousands of first time homebuyers on their journey and the one thing they all have in common is they have absolutely no idea what they are doing, they are overwhelmed and stressed, they dont even really fully understand the ideas and concepts of it. I found that I was spending time teaching them how to be good buyers for their lives before we got to the specific market and transaction, which of course is not the job of a realtor. Read more>>

Melvin Guzman | General Contractor & Framing Contractor

Leave the fear of trying something new, starting from scratch generates nerves but that is adrenaline for me. Read more>>

Jayla Shannon | Publicist & CEO of Lovely Lumination Candles

So my business was started during the beginning of the Covid-19 pandemic. I had just graduated college in December of 2019, started working my first job and literally three months later Covid-19 caused me to lose that same job. I was spending a lot of time at home and literally depending on government assistance to make money. With me being home all the time, all I did was clean and one thing I loved to do after I would clean was to light a candle. Now, of course at this point I couldn’t go to the mall or even spend the money on Bath & body Works like i used too because I just didn’t have it financially. Read more>>