Designing Her Entrepreneurial Path: Interview with Entrepreneur Tylar Masters

by / ⠀Entrepreneur Interviews Entrepreneurship Startup Advice / January 5, 2015

Hiscox Courageous Entrepreneur Interview Series

Hiscox-Small-Business-Insurance-Logo-6001This is part three of the ten part series. Follow the Hiscox Courageous Entrepreneur interview series on

Interview Series Sponsored by Hiscox Small Business Insurance.  Hiscox specializes in protecting IT/technology, marketing, consulting, health and beauty, photography and many other professional services businesses, tailoring coverage to the specific risks in your industry.

Tylar Masters

Tylar Masters, Founder Tylar & Co.

 Q: Do you consider entrepreneurs courageous?

A: “I think courageous is an understatement. It’s a huge step to take. You have to have a no-fear attitude.”

A ‘no-fear attitude’ certainly applies to entrepreneur Tylar Masters, founder of Tylar & Company. Tylar & Company is a full-service digital marketing and creative agency based out of Detroit, with a second location in Chicago.

Tylar has used that no-fear attitude, along with a non-stop work ethic and a positive outlook on life to build a successful company and brand from nothing.

“When I was 17, I was living in my car, but I wasn’t going to let that define my future. I knew I had talent as a designer in high school. I managed to snag a part time gig for a newspaper scanning in photos for the real estate section. In a few months, I was up for a job as a graphic artist. I knew I was under-qualified so I spent countless hours off the clock learning.”

Those few months of hard unpaid work paid off – she got the job. There were many promotions and new opportunities for Tylar over the next decade, including working for CBS Detroit. All of her work and experience in many fields and positions within media and the creative space served as preparation for eventually losing her position at CBS Detroit, which left her with the question “what’s next?” Next was utilizing her network and the relationships she had built over many years to start her own business in 2009.

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Letting go of her dreams due to obstacles was not an option for Tylar. “I can honestly say I’ve never thought once about giving up.” Asked how to bounce back and overcome tough times, Tylar said, “A friend taught me you have to turn to something that makes you feel really good about yourself. It forces you to feel valued and to see your potential again. For me it’s painting and photography.” She could have easily let setbacks control her future and stop her from obtaining her dreams, but continuing to work hard and refusing to give up made Tylar & Company a reality.

Tylar Logo

Entrepreneurial Risks

Risk is an inherent aspect of being an entrepreneur. While risk is in the eye of the beholder, many ‘normal’ people see us entrepreneurs as crazy risk-takers that would put everything we own and love on the line to pursue a wild and unstable business idea. The truth is much different, but there are many risks that entrepreneurs take on that aren’t a normal part of the standard 9-5 job. One of those risks is being financially responsible for the actions of yourself at work, your business as a whole, and your employees.

Q: How important is insurance for your business and do you have it?

A: “It’s absolutely vital. You have to cover not only your own actions, but those of your employees and contractors and freelancers. It’s impossible to gauge whether or not a business relationship will result in needing insurance, but having it creates that security so you can do what you do best without worrying about incidents or mishaps along the way.”

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Advice to Fellow Courageous Entrepreneurs

Biggest mistake as an entrepreneur: “Not delegating enough.”

“Sometimes I forget that I can’t do it all. When it comes to delegating, you have to make sure you are clear when assigning tasks to others. Creating a clear outline and make sure the person who will be tackling the task has the skillset and the talent to complete the task.”

Best piece of advice for fellow young entrepreneurs: “Never be afraid to break rules.”

“I taught dance for several years. My students would get really uncomfortable when I made them do some crazy choreography. And they would always say ‘we don’t want to do this, we don’t feel right.’ But I always make them recite my eight word mantra, which is, and I apply this to business as — the sillier you feel, the better you look. They won a lot of awards.”

Don’t quit now! Listen to the full interview with Tylar & Co.’s Tylar Masters below.


About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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