Deciding to start a business is an unusual decision. It’s often considered irrational and yet for many it’s the best decision they’ve ever made. So we asked folks to think back to when they were starting their businesses and to tell us about their decision making process.

Kim Kendall-De Silva

There was this one meeting — one of those that stretch on forever and say very little. I remember thinking, I could walk out right now. Drop dead. Not come back tomorrow… and nothing would change.

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The work would continue. The minutes would be typed up. Someone else would pick up the slack. It wouldn’t really matter. Read More>>

Sofia

My love for flowers began when I signed up for a floral design class after finishing graduate school and working full-time in an office. I was feeling burnt out from staring at a screen and constantly thinking about research and data. I craved something hands-on, creative, and disconnected from technology. While planning my own wedding, I became fascinated by how floral designers could transform a space with curated and colorful floral designs, so I decided to give it a try myself. Read More>>

Tymeka Coney

My thought process behind starting my own business has really been out of Love for what I do. There’s a quote that states, “When you are doing what you love, then it doesn’t feel like work.” I truly believe that. I also started my own business because I spent a lot of time helping and consulting others with their businesses so it was only natural that I would use that same energy that I used in helping others and start my own. There’s another quote which states, “Charity begins at home.” I have always loved creative pursuits and being surrounded by creatives and I have always loved helping others to find creative opportunities for their gifts and talents so naturally I would have a business that encompasses all of this. Read More>>

Amber Hudson

Wandering Free was never just a business idea — it was a calling that tugged at my soul long before I had a name for it. I’ve always been the one with a camera in hand and my heart set on the next adventure. Maybe it’s because I don’t have the best memory (seriously, if I didn’t take a photo, did it even happen?), but I’ve always felt this deep need to hold onto the fleeting — the wind in someone’s hair, the way two people laugh together when they think no one’s watching, the golden light just before sunset. Read More>>

Keeley Miller

I’ve always believed in the power of art to transform the way we see ourselves. As I grew as a photographer, I realized how deeply we as women need space to feel seen, celebrated, and beautiful — not just on the surface, but in our strength, softness, and complexity. Starting my own boudoir studio gave me the freedom to create that space intentionally Read More>>

Ofeliya & Cristie

Once we reached our mid-twenties, we started noticing how difficult it had become to make genuine connections. Outside of college, the only places we were meeting people were at work or in the bathroom line at bars (lol!). We also noticed that most of the events we attended didn’t cater to our age group or life stage, which made it hard to connect meaningfully. And after COVID, people became even more reliant on apps and technology for social interaction, leaving fewer opportunities to connect face-to-face. We both love creating spaces for people to come together, and it felt natural for us to build something that filled that gap. Read More>>

Amilcar Cob

What started as a game, eventually turned into a business, sometimes when you have certain skills (unknown skills), all it takes is to believe in yourself and harness said abilities that life’s given you.

I was aware of all the factors involved in starting a business. In college, you’re taught the tools and theories, but in real life, it’s a challenge, you learn in every step and misstep. I understood the risks that would represent to take a leap.
Starting a business, is like walking through a path filled with uncertainty and unexpected challenges. Therefore many will attempt to initiate a commerce but only a few will see it through. Read More>>

Ayaka Kamei Cento

When I was 17, I had the opportunity to perform in hospitals in Japan. That experience moved me deeply and planted a seed—I dreamed of one day doing something similar, though I didn’t know how or when.

Nearly 20 years later, I was a closing company member of The Phantom of the Opera on Broadway. The NYC performing arts scene is already incredibly competitive, and many of my extraordinarily talented colleagues were suddenly out of work. I didn’t want to see them simply go on unemployment—I wanted to create meaningful performance opportunities that would keep their passion alive as they navigated auditions and survival jobs. Read More>>

Rita Spiegel

My business was born out of two of my greatest passions: art and dogs. Throughout my life, I have been an artist at heart, expressing myself through drawing, photography, and painting. Dogs, particularly those who have shared their lives with me, have always been a significant source of inspiration. These two loves naturally intertwined, leading me down a path I hadn’t anticipated.

The image of Cocoa’s portrait resonated with many, capturing the interest and admiration of people far and wide. Friends, family, and strangers alike began reaching out, asking if I could paint portraits of their beloved pets. This outpouring of requests marked the inception of my pet portrait business. Read More>>

Ally Rose

Starting Ally Rose Photography wasn’t a single isolated decision, it was more like a slow drip of falling deeper in love with photography the more I did it. I knew pretty early on that this was more than a hobby for me: I get to shape a visual style that feels uniquely mine, to tell stories and carry emotion through images that do more than help you remember a moment – but truly feel it. Read More>>