How to think through whether you should start a business

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.

The inspiration behind starting my own business came from a deep, personal journey of healing and self-discovery. Having battled my own health issues, I experienced firsthand how frustrating it can be when traditional methods only scratch the surface, treating symptoms instead of addressing the root cause. This realization ignited a passion within me to create something different—a space where women could truly heal, not just cosmetically but holistically. Read more>>

I studied architecture in pursuit of creativity, and quickly found that starting a company scratched every creative itch. I co-founded a software startup out of grad school with three guys, we had met in a class. The ambition of the class was to change one billion lives with technology. Building technology, scaling it, deploying it, financing the endeavor, and building a team — along with so much more — turned out to be the most creative pursuit I’d ever embarked on. We have raised $72m to date, and continue to build Wise Systems — a tech company that focuses on solutions for the last mile of logistics. Read more>>

I wanted to share my love and knowledge of beach tennis with everyone and make beach tennis a popular sport and activity in the USA. Read more>>

I was seeing how much was wrong with the fashion industry and wanted to change it by setting an example of what a company could be. Read more>>

I’ve always loved the idea of owning a business that I could call my own. I love all things creative and arts, and through owning a business I’ve always found an outlet for my ideas. My first company was an urban customized jewelry line. I loved sourcing new pieces and creating new jewelry based off demand. Read more>>

I started V-Factor Social because I’ve always been passionate about the power of social media and how it can transform a brand or business. I began my journey as an influencer, building my personal brand from scratch to over 145,000 followers across Instagram, YouTube, TikTok, LinkedIn, and Pinterest. Along the way, I learned the ins and outs of social media, from creating engaging content to building a loyal community and monetizing my platforms. I then started coaching other content creators and entrepreneurs, helping them grow their own brands and turn their social media presence into a source of income. Read more>>

Playing music for a living didn’t seem like a choice. It was just something i knew i had to jump into and build from there. Read more>>

It was something that happened organically. Open Folk started as a mission to create a space to perform music in a different way. A mission to bring communities together, to expand the understanding or love and respect for the artistry and live performance. While trying to expand it, I faced many challenges that made me understand that creating a structure for this music movement was the only way forward. Read more>>

My thought process behind starting my own business was very simple, growing up I always know that I wanted to pursue something of my own. To be honest, I always thought that it’s going to be a design studio because that was the path I was on ever since high school and college. Don’t get me wrong, I’m still very passionate about architecture design and will continue pursuing it on the side. So going into starting my own business, it was a big pivot that I made, I could choose to gamble and give it all or play it safe. Read more>>

For many years, I envisioned creating a mental health private practice. My goal was to build something that not only allowed me the independence to work on my own terms but also contributed meaningfully to my community. Trauma is particularly prevalent in the Latino community, often stemming from experiences like immigration, generational poverty, discrimination, and the challenges of acculturation. Many in our community have endured hardship and adversity, yet mental health services are often inaccessible or not culturally attuned to their unique needs. Read more>>

I’m originally from Echo Park, Los Angeles but really moved all over when I was younger. Growing up and having no say in where I can go or stay really struck something in me. It made it difficult to even imagine what consistency or community looked liked since I never stayed in one place for long enough to create that. As I got older, I aspired having a strong sense of community that aligned with my values and interests. Read more>>

To be cheekily honest, I have never liked working for someone else. Too many rules and restrictions! I’m a Leo and very independent, creative, and leader-oriented. I feel stifled in someone else’s dream and had a deep need to live my own. On top of that, there will always be an income ceiling or a cap you reach if you don’t have your own business. As an entrepreneur, the sky is the limit — creatively and money-wise! I’ve always dreamed of creating my life on my terms, being able to do what I love the most everyday while serving the collective in a positive way. Read more>>

It was actually my late husband’s idea. He saw how passionate I was about sharing what helped us solve our parenting problems—problems that were only getting worse from the advice of well-intended and expensive experts. It was through his encouragement and belief that the process began. I am forever grateful to him. Read more>>

I came up with the idea of Mina + Pup Pet Accessories when I was 14. It came from heartbreak and loss and turned into something very beautiful and impactful. In July of 2020, my 34-year-old uncle Michael passed away suddenly, and my heart broke. He was my biggest supporter, and we were incredibly close. Michael loved dogs, especially my French Bulldog Angus. I wanted to turn my pain into a way to honor Michael’s memory. Read more>>

Starting my own business, “Lights, Camera, Ready!”, wasn’t just a logical decision; it was a calling. After years of grinding, I finally achieved my dream of being on TV. But once I reached that milestone, I found myself asking, “What now?” Read more>>

Starting my own business was a mix of anticipation, glee, and, honestly, a bit of dread! The thought process was fueled by a deep desire to innovate and create meaningful solutions for women—especially those who felt underrepresented in the hair care industry. I wanted to go beyond just selling products; I wanted to build a brand that resonated with real people and provided them with tools that addressed their unique hair needs. Read more>>

I started my first official business when I was 20 years old. Growing up with an entrepreneurial father as a role model, running my own business almost seemed like a foregone conclusion. From an early age, I was surrounded by the mindset of independence and creativity that comes with entrepreneurship. The idea of creating something from scratch was in many ways appealing to me right from the start. Read more>>

A combination of passion and independence drove my thought process behind starting my own business. I’ve always loved creating art and wanted to share my work with a wider audience. Over time, I realized there was a demand for custom illustrations, especially in areas like book cover design, mural painting, and other creative projects, where clients seek unique visuals. By turning my passion into a business, I connected with clients on creative projects, offering something deeply personal through my prints and commissioned work. Plus, having my own business allows me to maintain creative freedom and control over my schedule. Read more>>

I never intended on creating a business around my art. The universe just pushed me in that direction. I had started tie dyeing as a hobby. A friend was working at a local Deadhead owned brewery and gave me a shirt to dye for myself. I wore it to an event at the brewery and the owners really liked it. Fast forward to a few months later and I was started making shirts for them. I had just stopped working in publishing so it was the perfect time to start making shirts for money. Money isn’t the biggest motivation though. It’s working for myself, not having to rely on coworkers who don’t pull their weight and bosses who are jaded and don’t care anymore. Read more>>

Starting my own private practice was a decision that evolved over time, influenced by my desire to work more directly with clients and families while cutting through the limitations I experienced in previous roles. Early in my career, I loved my work in skilled nursing, supporting families through difficult healthcare decisions. However, navigating the red tape and bureaucratic hurdles became frustrating. When I moved into public education, I encountered similar challenges. While I appreciated the relationships and the work, I felt constrained by systems that didn’t align with how I wanted to provide care. Read more>>

The ultimate reason I created my business OneSoma was to help people heal and feel better in their bodies. I wanted to offer not just one-size-fits-all massages, but rather therapeutic bodywork sessions that genuinely recognized the ispecific needs of each client. I got certified in Rolfing Structural Integration just over three years ago because over many years of exploring various bodywork modalities, I found that Rolfing truly stood above the rest in its ability to dive deep into clients’ specific injuries, pains, and overall therapeutic goals. Read more>>

rooted in my passion for creating beautiful experiences and bringing people together. As a boutique wedding planning and design company, Viva is dedicated to celebrating life’s most cherished moments with intention and authenticity. With over six years of experience in events, marketing, sales, and branding, I realized my true purpose was in curating moments where people can celebrate fully and intentionally. The thought of never pursuing this dream weighed heavily on me, so I knew I had to take the leap and make it a reality. Read more>>

I had worked for other people my whole life and found it rather depressing.
I needed to make something change out of desperation. Read more>>

The foundation of our restaurant is centered around Día de los Muertos, a holiday we fell in love with during our travels. We wanted to open a business where the value of celebrating life is at the core of everything we do, which is why we started Calaca Mamas. In every decision we make, we strive to ensure that every person who enters feels free to express themselves—because life is truly too short not to enjoy every little moment. Read more>>

When I decided to get certified as a voice coach (through Brett Manning), I originally wasn’t interested in teaching! I thought going through the certification process would really help my own voice, and it has, but I ended up absolutely loving teaching. It’s a great “side hustle” to fund my artistry but it’s also incredibly rewarding and beautiful to help other singers get to know their own voices more and find their own, unique sound. Read more>>

My journey into entrepreneurship was more intuitive than strategic. From a young age, I was captivated by beauty and glamour. I began sharing my work on social media at 15 and enjoyed the positive feedback I received. In my sophomore year of high school, I did makeup for a group of friends for a school dance, charging them $20 each. This experience sparked my realization that I could turn my passion into a career. As I continued to grow my business throughout high school, I became increasingly committed. By my senior year, I chose to homeschool myself to dedicate all my time to building my business. It was clear that this was the path I wanted to pursue. Read more>>

Poppies N Petals flower bar bloomed out of a high school friendship in need of rekindling. Life is perpetually busy and as the three of us, Liz, Leah, and Leen moved to different cities and the years flew by, we saw each other less and less. When a recent milestone brought on a rare get together, we realized that too much time has gone by and too many stories have gone unshared. We needed an excuse to spend more time together. That day sprouted an idea to start a business doing something we all loved – sharing the joy felt among friends with others in the community – what better way than with flowers at celebrations. Read more>>

“I will figure this out”. Those are the words I used to reassure myself when starting my business.
I come from a family that is inexperienced with entrepreneurship. My family are all hard workers but have always had this fear of starting their own business. As a teenager I’ve had an ambition to change my families story. Read more>>

When I was a teenager, my father and I shared a passion for speed. We decided to develop a car to race that would be unlike any other vehicle we had seen competing and take a chance on something that no one else had yet to attempt. It was a risky venture because – due to the nature of the car itself: a 1969 Camaro that retained its original chassis but had been transformed into a true race vehicle – we had no idea how many events we would actually be allowed to enter. By building something new, we generated a great deal of interest and acquired a devoted fanbase – many of whom have been following our efforts for over 35 years. And, thankfully, we found that there were plenty of events willing to let us put our car on the track! Read more>>

I’ve been passionate about dancing and singing since I was a child, and the thrill I feel when I’m on stage is unparalleled. My journey into the world of performing arts was profoundly influenced by watching “High School Musical,” which ignited a desire in me to study musical theatre. I wanted to explore the limitless possibilities of self-expression through various art forms. Read more>>

Starting BODO Activewear was driven by a clear vision to cater specifically to women over 30 who are educated, health-conscious, and dedicated to self-care. As the founder, I wanted to create a brand that empowers these women by offering activewear that combines comfort with luxury. My goal was to design apparel that not only supports their active lifestyles but also makes them feel confident and stylish, demonstrating that they can achieve everything while enjoying premium, well-crafted workout clothes. Read more>>

MyALEPH was born from my passion for combining fashion with meaningful, protective elements. I wanted to create a brand that not only embodies luxury but also serves a purpose—allowing people to carry a piece of energy with them. I envisioned MyALEPH as more than just a jewelry line; it’s about style, personal expression, and harnessing the power of semi-precious gemstones for protection and positive energy. The process was driven by my desire to create something that felt both luxurious and personal. Read more>>

My open-minded attitude and creativity significantly contributed to my decision-making process when starting my own business. I am someone who isn’t afraid to try different things; even if I fail, I can easily adapt, while it may be difficult for others to do. I started The Grizzly Podcast because I was tired of having companies pass on me or not allow me the opportunity to grow as a personality or host because of politics or because they didn’t believe in me. I know my worth, and I know what I bring to the table because I am someone who is passionate about what I do. Read more>>

I’ve always been a creative person, and moving to Los Angeles, a city full of inspiration and creative energy, motivated me to pursue blogging. My love for cosmetics and skincare has always been strong, and it eventually became more than just a passion—it became my career. Before this, I worked in office jobs but dreamed of starting something of my own. LA gave me the push I needed to turn that dream into reality. My fascination with skincare, especially Korean products (which now make up 70% of my routine), led to my first collaboration with a Korean skincare brand, and that’s when my passion turned into a business. Read more>>

If you told me two years ago that I would own a bakery, I would’ve laughed. I started baking gluten-free for my daughter when she was diagnosed with celiac at age two and a half. There are so many great gluten-free substitutions, except for when it came to croissants. I personally love croissants and wanted my daughter to be able to experience the joy of a good pain au chocolat. There was one gluten free bakery in Los Angeles that made “croissants” but they were nothing like the real deal. Once while in Montreal, I took the kids to a gluten free bakery. Read more>>

Once I left my career in hosting and journalism, I realized that I still had so much to share with others, specifically with women. Thus, I took to social media to share my passions in painting, home decor, and consistently sharing my challenges and wins via my Instagram Lives. I found an entire group of women who had experienced chronic illness, divorce, loss, etc. and no topic was off limits for my Instagram family, I don’t refer to these lovely people as social media followers because I’d like to think that I helped them by sharing my vulnerabilities, and in turn they helped me grow and overcome some very difficult and painful experiences. Read more>>

My thought process for starting my own business came from being ill and having not worked in three years. Every time I began to get better and feel like I could join the workforce again, something major would happen – I’d get another diagnosis, an unexpected death in the family, you know – life. Read more>>

Control of my time and location freedom. Growing up I hated seeing me and my fam worship an alarm clock and not be able to just travel any day we wanted. Read more>>

“I founded my nonprofit organization to address and strengthen the vital connection between parents and children, recognizing a critical need for support in fostering healthy family relationships.” Read more>>

As an artist, you are your own business. In terms of my career, there was never another choice for me. I’ve been writing for as long as I can remember, and once I started acting, I never turned back. I’ve been doing them both for the majority of my life. Read more>>

I’ve been in Radio & Traditional Media for more than 20+ years. I’ve also directly and indirectly been involved in the Event Planning & Concert Business. I’ve also been a Columnist/Blogger/Writer for practically my whole life. And in each of those industries and genres, I’ve noticed a troubling dearth of Black/African American voices. Therefore, I knew that once the opportunity presented itself, I wanted to start a business that could amplify the voices and talents of the underserved and forgotten. Read more>>
I started my law firm by accident! I took time off from my legal career to explore the creative industry. When people learned I was a lawyer, they asked me legal questions. I realized there were a lot of unmet legal needs, so I started advising creatives and small business entrepreneurs. Read more>>
