Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.
Colleen Horn
If I could go back in time, I honestly wish I had started my business sooner, but I also understand why I didn’t. I opened Generations Chiropractic on May 1st, 2021. At that point, I was almost nine years out of chiropractic school, married, and a mom of two young kids. My youngest was just a year and a half. Read More>>
Rachel Hubbard
That’s a great question. When I think about it, I feel the timing was meant to be, though sometimes I wish I had started earlier. Still, every experience before this helped prepare me. I officially started my astrology business about three years ago. That was during my Saturn return and the pandemic, a time of deep reflection for everyone, including me. Read More>>
Isa Bourbon
I don’t like to spend too much time wishing I had done things sooner, but Bite Club is one of the exceptions to that rule. The desire and demand in Santa Barbara are incredibly high for curated meal delivery that highlights local produce, regional flavors, and supports small local businesses. Read More>>
Karen Kaplan
My partner Jen and I started A Little More Special at the end of August 2025. I had already started creatively sharing recipes, well-balanced lifestyle ideas, beautiful table settings and hosting tips in April. I decided the partner route was a positive move because we are more creative, have better ideas and stronger strategy direction together. Read More>>
Alex Cunningham
I would have absolutely started earlier. Growing up I thought I was going to be a rockstar. The problem was, I never took it seriously. I always just played the part. But I knew I wanted to be in front of people and make them happy. Then I saw Kevin Hart live and knew I had found my calling. Read More>>