Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Rob Jolles, President of Jolles Associates, Inc., located in Chevy Chase, MD, USA.

What's your business, and who are your customers?

I am a professional speaker specializing in sales and persuasion. I have spent the last forty years traveling over 2.5 million miles in the air, teaching, entertaining, and inspiring audiences worldwide. I work with classic sales groups, as well as many other professions that simply want to learn how to change the minds of their customers.

Tell us about yourself

I sold for the New York Life Insurance Company and Xerox before becoming a corporate trainer. Every student and audience member is a gift, which provides all the motivation needed to do my very best.

What's your biggest accomplishment as a business owner?

I'm proud of my bestselling books, but my biggest accomplishment might be my longevity. I will be celebrating 30 years, on my own, as a professional speaker. I haven't lost a step, nor do I intend to anytime soon!

What's one of the hardest things that come with being a business owner?

Handling the uncertainty and up's and down's that come with being a business owner. When things are great, we pat ourselves on the back, but when things are not so great, we have to be even kinder to ourselves.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Make sure you love what you are about to be doing.
  2. Don't be a victim of your mistakes; learn from them.
  3. Find a good accountant!

Is there anything else you'd like to share?

Don't be afraid to try. Most for do share the same mantra: "I wish I had done it sooner." No matter what you think will be the worst that might happen, it will never be worse than the thoughts of never having had the courage to try.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.