Interested in starting your own entrepreneurial journey in clothing but unsure what to expect? Then read up on our interview with Jayson Greenberg, Founder and CEO of Dr. Cheese Tees, located in Ann Arbor, MI, USA.

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

Dr. Cheese Tees sells retro sports moments and memories on super comfortable vintage-style t-shirts. We create nostalgic connections. Our customers are nostalgic and knowledgeable sports fans who appreciate a simple and subtle sports reference and still enjoy the magic of a comfortable t-shirt. They appreciate the power of a random passerby saying, "Hey, cool t-shirt!"

Tell us about yourself

I am a full-time physician who struggled with burnout and suffered secondary health issues as a result. I started Dr. Cheese Tees to leverage my love of sports through a creative outlet to raise my energy and boost my spirits. I am motivated to infuse fun and creativity into my life and connect with other like-minded sports fans who share those values.

What's your biggest accomplishment as a business owner?

First of all, I would call myself not just a business owner but a funtrepreneur. My biggest accomplishment is bringing this "I have a crazy idea" notion to life despite all the hurdles and fears in the process. I still get excited with every single sale.

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

For me, the hardest thing has been working through "the dip" after the launch. There is an incredible high after the start with all the support of family and friends...but it can be short-lived. That's when you realize there is so much still to learn. This has meant taking a hard look at what your true definition of success is as well as the financial bottom line.

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

  1. Find an inner circle you can surround yourself with that can help, motivate, and challenge you. I call them my unofficial advisory board.
  2. Do not be afraid to fail. Run your own race, but recognize the missteps, forgive yourself, learn the lesson, and move on.
  3. Don't forget about the fun part. There will always be stressors and question marks, but the fun parts need to stay fun.

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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