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.

Chantal Monfort | Mom blogger

I started @theallaroundmama to build a mom community, share and gain advice on motherhood and most importantly make some lifelong mama friends to go through motherhood together. Read more>>

Nicholas Kusnir | Marketing Manager/Social Media

I’ve always loved building communities, whether online or in person – so, being able to help brands use social media to spread their own messages seemed like a no brainer. Read more>>

Ken Lewis | Surfer, Dog Lover, Digital Marketer

Depends on which buisness we’re talking about. I opened my first business, a Skateboard Shop, in 1997-2003. It was a wonderful experience but it ran its course. I’m just now starting my second business which is launching in July 2024. For each instance there was a different inspiration but one thing rings true to both decisions; In a world of brands who want to use you and your talents, but don’t want to pay for it, why would I keep getting myself into situations that don’t feed my soul or my bank account? Read more>>

Donald Woodard | Craftsman/Business Owner

I read somewhere that if you do what you love, you don’t have to work another day. I have started other businesses that I was passionate about at the time. When I moved back to San Diego for the second time the beer industry was booming. I have been a long-time brewer myself and I loved it. I was about to start another business by opening a brewery and tasting room in Ocean Beach. After I found myself in my garage too often building furniture instead of brewing I realized that my passion had changed once again. I also liked working with reclaimed wood and focusing on being more sustainable in what I do. So I changed the business plan from brewing beer to upcycling trees and reclaimed wood into beautiful custom-made furniture. Read more>>

Tam & JT

Back when we were in college, we’ve always had a dream of starting our own business one day. Initially, we wanted to do something food-related, such as operating a food truck or owning a restaurant. Towards the end of 2019, both of us were still working our full-time jobs, but we wanted to start the new year in a new direction. We decided to revisit this dream of starting a business together. Outside of our full-time jobs, we were both developing our skills in t-shirt screen printing and food-inspired photography. This led us into our current business, which mixes fashion with food. Read more>>

Dara Krovetz | fine art photographer

I started my business Dara’s Bling Photography back in 2011 when I had a boutique called Jewelry and Baby Bling By Dara. My business started my journey into photography by photographing babies and children in the products I designed and sold. I taught myself photography by attending workshops in person and online. Read more>>

Amy Brockhaus | Professional Organizer

It’s an unfortunate truth in our modern day that we all have too much stuff in our homes, Between holidays, birthdays, online shopping, the marking we’re constantly objected too, the dopamine hit of purchasing and the guilt and shame we can feel with getting rid of items, most American homes are overburdened, leaving us feeling stressed and in a state of overwhelm. Our cortisol, the stress hormone, is activated when we enter cluttered spaces, meaning our homes are not restful and we’re more likely to want to numb out after a long day than connect or rejuvenate. Read more>>

Connor Mansberger | Wedding Cake Artist

I fell into my business by accident, and I still chuckle at how the whole process unfolded. As a previous health officer in the US Air Force, I never predicted that I would not only be running my own business, but also so heavily involved in an artistic field of work–much less the wedding industry! As an avid home cook, I’ve never had any formal experience working in a bakery, but I’ve always gravitated toward the kitchen where I thoroughly experiment creating dishes both on the savory and pastry side. Not long after I separated from the Air Force in 2022, my brother and his wife held a going-away party for their separation from the Marine Corps, where I offered to bring a few low-key sheet cakes as a contribution to their celebration. Read more>>

Wes Lauer | Founder/Owner of Dedication Fitness

Starting my own business in the fitness industry was driven by a combination of passion for fitness and a desire to help others achieve their health goals. I’ve always had a deep interest in exercise science and nutrition, and I wanted to create a truly personalized approach that could make a real impact on people’s lives. I saw an opportunity to fill a niche in the market by offering customized training programs, both in-person and online, tailored to individual needs and goals. This approach not only allows me to leverage my expertise, but also to build meaningful relationships with clients, helping them stay motivated, and committed to their fitness journey! Read more>>

Jesus Benayas | MSEE, Electronic Engineer; Hobby in common history of Spain and the USA

Most people are not interested in history, how did we get here?
Throughtout the years I realized the history of the United States its not told in its intirety. It magically starts with the English, Mayflower in 1620 and ignores the landing of Spanish Juan Ponce de Leon in Florida in 1513 (107 years earlier), or the landing of Juan Rodriguez Cabrillo in California in 1542 (78 years earlier) and all the other explorations from Florida to California that Spain did in those 107 years before the Mayflower arrived. Read more>>