The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Saul & Ana Casita Coffee Owners/Founders

Casita started with 2 little boys who were 2 and a newborn, each with a full time career job at the time we started. We have always commented and wondered where Casita would be at had we started before having children. Given the fact that we have our littles and do our best to not compromise family time with our boys, it has not been easy. Read more>>

Mari Ahumada

I love this question because my response varies depending on the flow of my days. Read more>>

Libby Perrington

I truly believe that everything happens for a reason, and all in God’s timing. However, one thing I do wish is that I would have learned the lesson of consistency sooner. I think when you’re young, you have all these ideas and your driven, you get stuck in the idea that you have to have MASSIVE action all the time. Read more>>

Maya White

For many years I did not think that I would experience the joy and freedom of being my own boss. I have always been a self- motivated person, however, finding my true career calling was one of the greatest stressors of my life. Read more>>

Nati Sanchez

I was always encouraged by family and friends to go on this adventure but I never felt ready or was able to distinguish it between a hobby or business. When I was laid off by my previous employer of 10 years it made it easier to go onto my journey. I do not regret starting earlier because creatively and mentally I was not where I am today. My years with my previous employer plays a great role in my business today because of all the experience and knowledge I took from it. Read more>>

Josh Perry

I was a manager for several successful startup companies long before I ever had the confidence to become a true entrepreneur myself. I am thankful for the experience I gained on others dime but i can’t help but think how much further along i would be had a been brave enough to just figure stuff out as i went along and hire the right mentors and coaches to assist. Read more>>

Mike Walker

My wife and I made the decision to start a business at the end of 2017. It’s something we had both considered for some time and finally felt ready to pursue. I was a mortgage banker at the time and felt that working in a commission-based sales job was the final experience I needed to have an inkling of what I might be getting myself into as an entrepreneur. We started planning early in 2018 and opened the doors to our escape room business in November of that year. Read more>>

Crystal Cao

After 15 years in the finance industry, I recently took a leap of faith to pursue my true passions. Now, I find fulfillment in steering my two brands, Otelier, a skincare venture, and CECloset, a lifestyle brand. This exciting shift has brought me a profound sense of purpose, allowing me to follow my dreams and embrace my passions before hitting the milestone of 40. Read more>>

Aubrey Miles

There are time when I wish I started photography sooner but then there are times I wish I started it later. Due to my passion for photography, I wish I started sooner. I picked up the camera and started teaching myself back in 2017. I had just gave birth to my 3rd child but wasn’t in a financial position to afford newborn photography. Read more>>

Claudia Paksi

Looking back, I wish I had initiated my business, Thriftsbyeandc, much earlier. I launched it during the summer before my first year of college. Initially, my plan was to be a full-time student without a job, focusing entirely on my studies. However, it proved challenging to find employment that accommodated my school schedule, prompting the realization that I needed income to support my education. Read more>>

Briana Cain

Starting a business was always a big goal of mine. I started my business in 2020 when I was sixteen years old. At that time I was in high school actively searching for part time jobs, but unfortunately I had no luck. Since I was having a hard time finding a job it motivated me to get serious about my goal of starting up my own business. Read more>>

Tamar Taylor-Brown

If I could go back in time I wish I would have started my business earlier for sure. I started my business about a week before covid hit. No one knew how long it would last or how things would end up in the long run. Read more>>

 Pharaoh Muhammad (Bradney) Khalil (Hernandez)

If I could go back in time I would definitely start sooner and invest a lot more heavily into it than I did in other hobbies or pass times. I started doing poetry at about 12 or 14 years old and decided to start doing spokenword at 16. From then on its just been a constant grind to continously build up my name and recognition that honestly could’ve started a lot sooner in my career if I had been focusing on myself rather than impressing the people around me. Read more>>