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.

Kevin Davidson

If I could go back in time, would I start my business sooner or later? It’s a question I’ve asked myself many times, especially because the biggest push toward finally going all-in came from one of the hardest chapters of my life. I started my business in May 2024, but the seeds of it were planted decades earlier. Read more>>

Shekar Kadaba

I landed in Canada at 21. Technically, I came as an international student—but if I’m being real, it felt less like a grand plan and more like a stroke of luck. I had a few offers lined up from U.S. schools. Then Halifax threw a scholarship my way, and just like that, my course changed. Read more>>

Tara & David (Bush) Jones

If we could go back in time, would we start our business earlier or later? The real answer might ruffle a few feathers, but here it is: We started exactly when we realized corporate America thought cold pizza, boring happy hours, and the generic congratulations emails could replace respect for our time, energy, creativity, fair treatment and real appreciation. Earlier? Absolutely not. Read more>>

Hal Copeland

I am confident that I started my business at the right time. While the idea for my hot sauce company was something I was passionate about for years, the two decades I spent in a restaurant were an indispensable incubation period. That time wasn’t a delay; it was my education. Read more>>

Aleia Burdekin

If I could go back in time I would’ve started my journey as a baker when I first got the idea back in 2021. I started my business as a hobby in October of last year and it semi took off. Read more>>

Patrick Reidy

Looking back I wish I would have got into the film industry sooner when I was younger. If I would of known I would of had such a passion and desire to do this getting into it sooner would of helped a lot more then getting into it in my 30s but either way glad I have decided to do it. Read more>>

Fatima Khambati

If I could go back in time, I think I would still begin my business at the exact moment I did. My art journey didn’t come from a perfectly planned place—it began in a very real, very personal season of my life. Read more>>

Lilia A’Hearn

If I could go back in time, I would still choose to start my business at the exact moment I did. I launched my company during a season of transition—balancing motherhood, creative growth, and the spark of finally believing in my own voice as an artist. Read more>>

Autumn POCHIRO

Do what you love and work for whom you admire the most, and you’ve given yourself the best chance in life you can.’ Warren Buffett I’ve been an entrepreneur since I was a kid! At just ten years old, I kicked off my journey with a paper route and then launched a tiny cleaning service for my three paper customers. Read more>>

Micayla Eligwe

I believe everything happens for a reason when it should. If I could go back in time to start my business sooner, I would have taken better advantage of my circumstances back then. Living rent free, no bills, or children to take care of, that would have been an ideal situation to take a chance and dive wholeheartedly into my art career. Read more>>

Sunny Liberty

“I wish I had started earlier in life so I could have helped even more people, but then I wouldn’t have the wisdom I have now. It takes mistakes to create winners. The struggle is part of the journey, and I finally understand that I wouldn’t appreciate the highs of my career if I hadn’t experienced the lows.” Read more>>