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.

I wanted freedom. Not just financial freedom, but the freedom to build something meaningful, to serve my community, and to create generational wealth for my family. I saw too many people stuck in cycles of renting, debt, and misinformation. With AKB Realty Group, I wanted to help families become homeowners and investors. With Manifest Equity, I wanted to make sure families going through probate had a trusted partner to guide them. At the end of the day, it’s all about impact. Read More>>

Me, my Wife and my business partner do not want to be tied down to a 9 – 5. My business partner and I both work in oil and gas, and its given us some great opportunities for us to expand into the entrepreneur lifestyle. When we met our current tattoo artist, who was a long-time friend of my Wife, gave us an opening to finally get some sort of business going. Read More>>

To be honest, I started my business by accident. Originally, it was just a hobby—something I did as a creative outlet while working as a school counselor. At the time, I had transitioned from relaxed to natural hair and used wigs to boost my confidence during the process. My initial plan was to be a YouTuber, reviewing hair for companies and sharing my passion for hair with the world. Read More>>

Growing up immersed in the real estate industry, with my mother owning her own company, I developed a deep understanding and passion for the field. I began my career in on-site sales and eventually obtained my Broker’s License, gaining extensive experience in various aspects of real estate. Read More>>

When I first started doing photography, I never planned to turn it into a business. I began by taking photos at local automotive events with my phone and quickly found that I loved it. So, I decided to invest in my first camera, a Canon T3i. As I attended more car events, I started receiving questions about where I was posting the photos, which eventually led to car enthusiasts asking for private sessions. It wasn’t until later that I realized I could actually make money doing this, which is when I decided to turn my passion into a business. From automobiles, I branched out to photographing models, families, and various other styles of photography. Read More>>

The Thought Process Behind Starting LoveNspire
LoveNspire was born out of necessity and transformed into a passion for sharing and celebrating cultures. In 2020, during a time of global uncertainty, I found myself driven by the need to contribute in any way possible. With nothing but a sewing machine and a heart full of determination, I began crafting handmade safety masks and ear savers, ensuring comfort and protection for those in need across the United States. Read More>>

After years of working as a dietitian in the hospital setting, I started feeling burnt out. I was working incredibly hard, but the impact I was making felt minimal. Patients often weren’t ready to change or the focus was more on immediate medical concerns rather than long-term behavior change. I had no doubt in my mind however that with the right environment and committed individuals, I could truly change lives. Starting my own business gave me the autonomy to work with people in a more effective way that actually drives lasting change. Now, every decision I make is my own, and I get to create a coaching experience that’s effective, personalized, and built around what actually works. Read More>>

My thought process behind starting my own business was creating something that was exciting for me to wake up to every morning, Not only that, I wanted both creative and financial freedom. I wanted to put all my energy into my craft and not worry about how many hours needed to be clocked or how much money was being made. My passion for all things cosmetology, outweighed effort and the risk. Read More>>
