Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Harry Freedman, a Funny Fake Motivational Speaker, based in East Norwich, NY, USA.

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

I perform as a funny fake industry expert for corporate events. I start off as if I'm an actual expert in their field and get everyone laughing even as the audience thinks I'm for real. I'm also a standup comedian (a regular opening act for Ray Romano) and perform a lot of toasts and roasts.

Tell us about yourself

I started as a standup comedian and, after about 10 years, discovered that I was a perfect fit to do corporate events as a funny fake expert. I love putting targeted material for corporate events and learning what makes them tick. I also get a huge kick out of surprising the audience, which is expecting a serious boring speaker with all the material I've written about their business and often some of their key people.

What's your biggest accomplishment as a business owner?

I had a full-page profile in the business section of the NY Times in a Sunday 4th of July issue. I've appeared as an actor on Everybody Loves Raymond, Men of a Certain Age, and a new movie coming out next spring called Somewhere in Queens. My biggest accomplishment is finding a niche in the corporate market that makes me unique, and I am still thriving at it.

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

I don't like all the paperwork. I also do my own marketing, which is a necessity but takes time away from the creative part of the business that I got in it for.

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

  1. Make sure you want this, and it's not just a whim. I spent a lot of money on marketing flyers even before I had performed as a funny fake expert. I was so convinced that this was my future that I went all in. Fortunately, it all worked out.
  2. Have enough money to take the risk. I would be very careful about betting your home or savings on something that's not a pretty sure thing. Of course, many people have broken that rule and become hugely successful. I believe those are the exceptions. I know a lot of people who bet on themselves and have spent years or decades paying off loans that they couldn't afford.
  3. Make sure you like at least some of the work, and it gets you going in the morning. Most careers come with good and bad. Will you still want to be doing this in a year, 5 years, 10 years, etc.?

Is there anything else you'd like to share?

I believe in taking calculated risks. There is no gain without some risk. Friends and family may urge caution because they fear seeing you get hurt (or having to support you if it goes bad. Do all the homework for what you're considering. If you have considerable experience in the field and think you see all the pitfalls, I'd say you're probably ready. If not, learn as much as you can before taking a leap.

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.

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