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.

Margaret Gay | Owner, 27Teas

I worked in the ‘corporate world’ for 6 years, but always felt a need for more. I never felt truly fulfilled with my work, and knew I wanted to do something that was my own. I started out with the basics, ‘what was something I truly liked and found passion in?” I also asked myself where I saw a need. Read more>>

Alyssa Morgan | Real Estate Agent and Founder of The Inside Network

My original thought process on starting the real estate company INSIDE stemmed from my passion for taking my team to the next level by providing elevated marketing, public relations exposure, strong social media presence and providing infrastructure for real estate agents that runs like a proper business. Read more>>

Dwight Thomas | Private Investigator and Business

Giving over half of my whole life to one field was the thought process for me. Having so much gained experience and working a certain type of why than your peers it kind of reflects on your energy. The company looks amazing while you represent them as a number. Read more>>

Linda Tannenbaum | Linda Tannenbaum, CEO/Founder and President of Open Medicine Foundation

Linda Tannenbaum is the CEO/Founder/President of Open Medicine Foundation (OMF), the largest private global research organization focusing on myalgic encephalomyelitis/chronic fatigue syndrome (ME/CFS), which is affecting millions of more people with long COVID. OMF supports 7 Centers in 4 countries on 3 continents, and is based in Agoura Hills, CA. Read more>>

Joanne Tan | Event Space Owner

After years of working in the corporate world, helping other people build their dreams and grow their businesses, I felt it was time that I did it for myself, my family, and my community. I wanted to use my skills and experience to build something that would help others and myself who do not have access to as many resources and large funding. Read more>>

Lucia Kanter St. Amour | VP of UN Women (San Francisco); Attorney; Activist; Author

Well, it wasn’t the plan; it was a matter of necessity. Six years into practicing law, in 2004, I had my first child who turned out to have a profound disability. I was managing a team of 14 interventionists for him at one point, with my second baby hoisted on my hip. Read more>>

Victoria Pappas | Lawyer and Real Estate Broker

After over ten years working as a lawyer in “big law,” I decided to start my own law firm handling projects for a select group of clients. I realized that the work I was also doing as a realtor part-time brought out my passion for real estate and helping others. Read more>>

Ariana Conlon | Ariana Conlon: Supper Club Host

“If you do what you love, you’ll never work a day in your life.” After years of doing what we love, we finally decided to turn our passion for hosting into a business. We started small, kept the vision simple, and eventually grew! We love meeting new people and showing them a good time. “People who love to eat are always the best people!” Read more>>

Yiannis Vogdanis | Multidisciplinary Artist

I always knew that at some point I will have my own studio. Being able to work at my pace and style was something that I could not compromise. That being said, I had to work for companies and universities until I had the proper set of skills and confidence to be able to venture on my own. Read more>>

Thuy Kay | 360 Photo Spin & Social Media and Marketing

Starting my own business was something I had thought about for some time. Working in the social media and marketing industry for several years, I realized there was an opportunity to create something unique and special that could bring people together.  Read more>>

Damaris Edme | MSN-Ed, RN, FCN, CEO & Co-Founder, Tutor

Our thought process stemed from passion. We have always known that we wanted to help the next generation of nurses be well educated, confident, and equipped to tackle the world of nursing. Read more>>