Interested in starting your own entrepreneurial journey in health and wellness but unsure what to expect? Then read up on our interview with Jack Gindi, Co-Founder of Cheeky, located in New York, NY, USA.

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

We are a subscription service for teeth grinders. We send our users a new custom mouth guard every three months so they can maintain optimal hygiene. We serve teeth grinders all over the world, hoping to provide a good night's sleep at an affordable price. Our mission is to democratize access to quality oral care for all types of people regardless of income bracket.

Tell us about yourself

I am an EXTREME teeth grinder. I got motivated to start this business when I lost my expensive custom night guard and couldn't find a dentist-quality replacement at an affordable price. I'm motivated by our customers, who expect the very best from us each and every day.

What's your biggest accomplishment as a business owner?

Taking Cheeky from zero to one, I think, is probably my biggest business feat to date.

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

You have to separate your self-worth from your business metrics. You are not your ROAS! It took me a long time to realize the importance of maintaining a level head while traversing the ups and downs of a start-up. Business is never a straight line. There will be lots of bumps along the road; just stay consistent, positive, and resilient, and you'll be able to get through almost any challenge.

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

  1. Have a really good understanding of your unit economics, inventory cycles, and the payback period your cash balance allows you to have on ad spend.
  2. Find co-founders with complementary skills, but it's more important that you each respect and admire each other. Founder break-ups kill start-ups.
  3. If you're the CEO, you should be spending as little time on operations as possible.

Is there anything else you'd like to share?

Starting a business is hard! I think one of the biggest factors in having success is just being resilient. So many people give up at the first sign of trouble. If you aver conviction and traction, keep going!

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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