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.

Richard Bakewell | Director & Director of Photography

In the beginning of my career I worked for a lot of companies, mostly reality shows because it was a consistent paycheck. However I worked hard for the money, and after a few years of breaking my back and fighting with companies who kept telling me that there was only “this predetermined rate” available. It was a take it or leave it approach, and was not very inspiring to me. Read more>>

Sammy Coyle | Wedding & Senior Photographer

I have always loved photography even if it wasn’t always a plan to make it a career. I have countless photo albums from as far back as I can remember and have always loved taking photos. I got my first DSLR camera in college in 2010 and learned how to use it mostly through trial and error. Read more>>

Halim Flowers | Culture Manufacturer

For me, I never felt like having a job was an option. Since I was a child growing up in Washington, D.C. during the Crack and Reaganomics era, I had a reasonable suspicion that the traditional model of going to school, getting a degree, and getting a job would not lead to the wealthy lifestyle that I wanted for myself. Read more>>

Anthony Ortiz | Film Director & Content Creator

Well I grew up in a very entrepreneurial environment because of my mother. She started her own marketing business when the internet started booming in the 90’s. So when I became an adult and started to dabble in filmmaking I knew I wanted to do something in business. Read more>>

Roxanne Hunt | Wedding Officiant, Happiness Coach and On Camera Personality

I have had an entrepreneurial spirit for some time and had already experienced working on my own in a few other areas. Although I hadn’t planned on or even thought about being a wedding officiant, the idea started from a request by someone who had heard me speak from the stage, loved my message and energy and wondered if I would consider officiating his sister’s wedding. Read more>>

Vanessa Sanchez | CEO & Mom of 2

My thought process behind my business was simply an idea that my husband created after we went to a big chain store that sold the most common Mexican “Antojitos” or “Snacks” & one of the things we tried was an Esquite or Corn in a Cup. We were not satisfied by flavor and since my husband knows how much I enjoy cooking and he loves to challenge me to recreate certain foods, he asked me to make an esquite. Read more>>

Justin Imamura | Founder & President

The thought process behind starting my own non-profit started back in 2016. In my daily commute to work in Downtown San Jose I noticed an excessive amount of trash and illegal dumping happening throughout the City. It was getting progressively worse and worse. I did some research to find out who was in charge of keeping the public streets/waterways clean and found out there was little to no resources available. Read more>>

EFFRAIM | Visual Artist and CEO of Clothing brand HATELAND.CO

At first, I was nervous. It was my senior year of High School, and the pandemic had just begun. During my newfound free time, I would create custom artist merch and album covers for my own entertainment. I realized I could bring original ideas and art to life. With enough time and effort, I could financially support myself by doing what I love, creating art. During that time, I constantly came across the phrase, “Be the change you want.” Read more>>

Lauren Nadel, Christin Neal | Cofounders of MAFF

Do you know what’s going on in arts & culture in Bangkok, Thailand or what about Accra, Ghana or Istanbul, Türkiye? The list goes on. There are so many talented creatives across the world that aren’t being exposed in mainstream media. We recognized the need to give those creatives a platform. Read more>>

Stephanie Kluk | Owner & Director

Starting my own business has always been a goal of mine since college. Fast forward many years later, after a variety of non-profit arts management jobs, I finally felt ready to take the leap. I started Future Ink Graphics (FIG) at the start of Covid. It wasn’t the plan but became the best and worse time to do it. I had been discussing my ideas and how I wanted to run my own space and a colleague said to me “you have been doing this for 20 years for other people, why don’t you do it for yourself”. Read more>>

Jason Treuting | Percussionist/Composer – Co-Artistic Director, Sō Percussion

We started the group when we were studying contemporary percussion music in grad school and it was pretty natural to want to keep playing together. At the time, we felt like our scene was ready for some new energy and a new approach to contemporary and experimental percussion music. The business part came a bit later when we looked at how some other groups, like the Kronos Quartet and Bang On a Can, had organized themselves and we looked to build on that structure to make our vision work,. Read more>>

Courtney Leavitt | Hairstylist & Educator

I would have to say, it started out of necessity if I’m being completely honest. I liked the place I had been working at, but such is life, my circumstances had changed. I became an uncle and lost my father within 3 months of each other, and my thought process became “How do I set up my life to be present for the people who matter most to me?” Read more>>

Kalyn Merkle | Esthetician & Waxer

I really just wanted to wax people. I have always loved talking to my clients while waxing them, I’ve gotten to know so many people and have grown to cherish learning from others how we* (humans) deal, struggle and grow through adversity. Connection was my greatest motivator. I knew how to wax and connect but I didn’t understand how to do business at all. Read more>>

Taimarys Elias | Nail Technician

I started my business during lockdown in 2020, and my only thought was “It’s now or never.” I graduated from beauty school in October 2019, thinking I made a HUGE mistake and that the beauty industry was not for me. Beauty school was not what I expected, and I definitely did not feel ready to start my career as a nail tech with the little I learned. Read more>>

RENA MAEDA | BRIDAL HAIR AND MAKEUP ARTIST

Before I started my own business, I was working for a multiple bridal companies. I always thought that I could’ve given a better customer services to make bride even happier and satisfied. Now, I’ve been through the wedding on my own, also having children. Read more>>

Courtney Lockridge | Body Sculpting Practitioner

I wanted to create a space where people can leave all their insecurities aside and focus on how they can achieve their health and body goals. Time will not be a factor and progress will be the most important aspect of their journey. Read more>>

Shifra Klein | Co-Founder Hamsa Kosher Edibles

To be perfectly honest, Hamsa Kosher Edibles was not a choice, it was a necessity. My child was diagnosed with Severe ASD (Autism Spectrum Disorder) at 2 years old. After 8 years of searching for ANYTHING that would give him some relief, I started to deep-dive into Cannabis as a treatment for Autism. My mind was blown. Read more>>

Akil Victor | Best selling author, entrepreneur and brand owner

Independency initially, followed by legacy. I worked for a larger company in management. I covered a regional territory where I personally handled money, made the deposits and forwarded the balance sheets to headquarters. Read more>>

Steven Sandler | Professional Photographer

It was a matter of physical and emotional survival. Photography is my second career in life. I used to practice law, I was working for an unethical and abusive employer at the time. It was killing me physically and emotionally, inside and outside. I had to get out. I’d been a serious photographer for my entire life, but coming from an upper middle class suburban family, a career as an artist was unthinkable. Read more>>