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Top 10 Entrepreneurs Over 40

It’s finally here: the first Top 10 list from MO.com! We spent the past month seeking out the Top 10 Entrepreneurs Over 40. From diamond rings to cancer rehabilitation centers, we have inspiring stories of entrepreneurs who braved new businesses later in life.

Starting a business later in life contains inherent advantages and disadvantages. Disadvantages result from a greater amount of risk, due to retirement being closer, kids attending college, and more personal expenses, like car payments and mortgages. Those risks don’t necessarily outweigh the advantages, though, as having more life experience oftentimes leads to more funding, a bigger network, more knowledge, and, most importantly, more maturity.

Here’s our list of the Top 10 Entrepreneurs Over 40 who decided that the reward was worth the risk.


Richard J. Phillips

Founder & CEO of Phillips & Company


Phillips & Company is a global public relations and business development firm. Richard is also beginning a new venture in 2013, Hill Country Golf & Guitar, an Austin-area entertainment venue and restaurant. Richard believes that “the best thing about launching a new venture in your 40s is the recognition that the customer is the most important part of your business.”



Ben T Smith, IV

Founder of Wanderful Media


Wanderful Media is a Silicon Valley company reinventing local discovery shopping by helping retailers bring consumers into local stores, while providing consumers with the most convenient way to discover local merchandise.  Ben loves entrepreneurship, and thinks that starting his company later in life “gives him less hesitation on making tough decisions,” but still “interferes with his need for naps every day.”


Cynthia Martin

President of Law99.com


Law99.com is a free web platform designed to deliver convenient, community-based, transparent, and low-cost legal services to Middle America. Cynthia embraces the risk of “unpredictable retirement” and feels her extensive industry experience and developed professional network give her an edge that only comes with time.



Deborah Wiener

Founder of Slobproof


Inspired by the slobs she lived with, Deborah restarted her professional career by helping other families and pet lovers who needed indestructible home furnishings with style and comfort.  Deborah loves the flexibility entrepreneurship gives her to be a mom and a business owner. Her experience let’s her operate with a “fearless-and-nothing-to prove attitude.”



Diane Stokes

Founder of Oncology Rehab Partners


Oncology Rehab Partners is an innovative healthcare company enabling cancer survivors across the country to recover from the debilitating side effects of treatments. Diane used her knowledge of “understanding how to build a business”, as well as “knowing what she doesn’t know” to help build a successful business. She also overcame the challenges of working 7-day workweeks and powered through the stress of being responsible for others’ livelihood.

Jeff Frank

Founder of Simplicity Sofas


Simplicity Sofas is an American furniture company that designs and builds Sofas for Small Spaces and is nationally recognized for its “extreme” customer service philosophy. Jeff started Simplicity Sofas at the age of 55, and his industry knowledge enhanced his ability to grow a business in a struggling market.


Tobi Kosanke, Ph. D.

Founder of Crazy K Farm Pet and Poultry Products, LLC

Crazy K Farm is a business that manufactures innovative products for pets that improve the quality of their lives.  Tobi recognizes the challenges of having to deal with many more things than just her business; she fights through the mindset of being too set in her ways, pushing her self to try innovative approaches to build and grow her business. Tobi feels her biggest advantage in waiting to start her business is the added patience; she’s overcome the desire for instant gratification,instead focusing on long-term results.


Ana Hawk

Barter Expert and Founder of Instant Barter LLC


Instant Barter provides traditional barter exchange services, with innovative “next generation” thinking and execution. Ana has also created a board game to help show the benefits of bartering to entrepreneurs at www.mybartergame.com. Ana emphasizes her “experience, knowledge, connections, and reputations” as advantages that helped her start a successful company, and when asked about the disadvantages, asked, “Are there any?”


Ruta Fox

President & CEO of DivineDiamonds.com 

DivineDiamonds.com is a high quality jewelry retailer. Their claim to fame is The Ah Ring™, which is the first and only diamond ring designed for, and marketed to, single women. Ruta’s challenge when starting Divine Diamonds was actually lack of experience in her new field, but she used her expertise in marketing and PR to grow and gain publicity for her new venture, which gained her placement on The O List in O, The Oprah Magazine.




Teri Freeman

Founder of MyPerfectGift.com


MyPerfectGift.com is a free online universal gift registry. Its mission is to utilize the power of the internet to make every gift experience the best it can be, ensuring everyone always receives The Perfect Gift©. Teri inspiration was when she realized, over time, it was difficult to get someone a gift he or she actually wanted. Teri has enjoyed the challenges of learning a new industry while building a company. In her eyes, although she’s “competing against 20-year-old computer geniuses, she’s a 30-year-old with 32 years of experience.”


Would you like to see yourself, or someone you know, on our next Top 10 list? Are you an entrepreneur who knows his way around digital tools to help his company succeed? Are you a social media whiz, an SEO expert, or simply great digital marketer for your brand? Apply today and tell us why you should be featured on MO.com’s Top 10 Digital Entrepreneurs.

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