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Creating Communities: Wyndy App connecting parents and collegiate students

When Ginger & Tommy Mayfield found themselves in regular need of convenient and trustworthy childcare for their two girls, they took matters into their own hands. Now Wyndy is pairing families with local college students for one of the safest options of childcare and part-time income on the market. We sat down with Tommy Mayfield […]

When Ginger & Tommy Mayfield found themselves in regular need of convenient and trustworthy childcare for their two girls, they took matters into their own hands. Now Wyndy is pairing families with local college students for one of the safest options of childcare and part-time income on the market. We sat down with Tommy Mayfield to discuss why Wyndy is such a lifesaver and how it came to be. 

What is your backstory?

I’m a native of Birmingham, Alabama. After graduating from Vanderbilt University, I moved to Washington, DC to work for an international human rights group called International Justice Mission (IJM).  IJM has teams of lawyers, investigators, and social workers in offices across the world who help rescue individuals from some of the worst forms of human oppression, including slavery and sex-trafficking.  After IJM, my wife and I moved to Charlottesville, VA, where I attended law school at the University of Virginia. In 2009 we moved back to Birmingham, and I spent several years practicing law at a large firm before taking the plunge into entrepreneurship by founding Wyndy.

Wyndy, which launched in early 2017, was born from a desire to solve a problem that my wife and I faced. I was working long hours, my wife was getting her master’s degree at night, and we had two daughters under the age of five. We needed lots of babysitting help, but finding reliable childcare was extremely difficult. Like millions of other parents, we found ourselves using the same technology that parents had been using for more than a decade, which was basically no technology.  We’d meet a handful of sitters through offline relationships, add their numbers to our phones, and then send what seemed like hundreds of text messages to book one. We’d then have to stop by the ATM late at night or scrounge for the checkbook to pay the sitter.

It eventually occurred to us that we were living in a world where apps like Lyft and Shipt made it possible to get a ride or have our groceries delivered at the tap of a button.  Why wasn’t there an app that could make it just as easy to find, book, and pay trusted babysitters? Well, now there is. With Wyndy, we’ve harnessed the power of modern technology to transform the way parents find reliable childcare by connecting them with a community of vetted, background-checked college babysitters.


Can you share the funniest or most interesting story that has happened to you thus far in your career?

I think one of the most interesting aspects of Wyndy has been the way that our platform has led to an increased level of professionalism when it comes to babysitting.  Our ratings system and parent connections feature lead to both parents and sitters going the extra mile to ensure the other person has a great experience. For example, we’re seeing parents who, before Wyndy, might have left the sitter without anything to eat, but now they order pizza so the sitter has something to eat if she gets hungry.  We’re also hearing of sitters going above and beyond by doing things that, I think, they historically haven’t done, such as washing the dishes, folding the laundry, or showing up to a house with crafts or games to engage the children. These are very simple acts, but they really enhance the experience for everyone.

Who inspires you?

Having grown up in Birmingham, I’ve always been interested in the city’s history, particularly the integral role that it played in the Civil Rights Movement.  One of the heroes of the Birmingham Civil Rights community (and a hero of mine) was a pastor named Fred Shuttlesworth. Shuttlesworth, along with Martin Luther King, Jr., was instrumental in organizing the Children’s March in the spring of 1963, in which hundreds of students faced fire hoses and police dogs to take a stand for equal rights.  The images from that spring shocked the world and helped lay the groundwork for the passage of the 1964 Civil Rights Act.

I’m also inspired by innovators like John Zimmer, the co-founder of Lyft.  I recently listened to an interview he gave on NPR’s How I Built This podcast. In it he spoke about how bizarre the notion of getting into a stranger’s personal vehicle was when he and Logan Green launched Lyft in 2012.  

What inspires me about Shuttlesworth and Zimmer is that they both believed in a future very different from the present they inhabited and had the courage to to turn their vision into a reality.

How have you used your success to bring goodness into the world?

We not only seek to serve communities where we are, but actually help create a community that didn’t exist before Wyndy.  By connecting parents with local college students, we enable them to have time to connect with a spouse or friends, pursue career opportunities, or participate in charitable activities that benefit their community.

We also empower college students by enabling them to earn a viable yet flexible income while in school, make meaningful connections with families, and build a living resume. Upon graduation, if a Wyndy can tell a prospective employer that they did well in school, were involved on campus, and also completed hundreds of Wyndy jobs while maintaining a five-star rating, they’re showing that employer that they know how to manage their time and work with people These two skills are fundamental to success in any profession. In short, we’re helping our Wyndys make babysitting something worth putting on their resumes.

We also have several special programs that serve each side of our marketplace.  We have provided Wyndy’s service free of charge to widows with young children and plan to partner in the future with non-profits and other organizations that will help us expand the scope of this program.  Additionally, we’ve established a Wyndy scholarship program, through which we give small scholarships to Wyndys throughout each each semester.


What are 5 things you wish someone had told you when you first started, and why? Please provide an example/story for each.

  1. Starting a startup is HARD.  A friend and fellow entrepreneur once said that if founders had a crystal ball and could see what the first year of a startup looked like, most wouldn’t start their business. People told me that starting a company would be the hardest thing I’d ever do.  While I intellectually believed them at the time, I really believe them now. It’s fun to dream about building a business from nothing, but actually attempting to do so isn’t for the faint of heart. There are so many things to do, so many challenges to overcome, so many risks to mitigate, and so much room for self-doubt along the way.
  1. Starting a startup is also FUN. While starting a startup is extremely hard, it’s also a lot of fun. It’s a rare chance to try to transform the world--to take your vision for how the world should be and turn that vision into a reality.  Wyndy was born from our belief that, in 2017, finding, booking, and paying a trusted babysitter should be easy. We’ve now made substantial progress toward turning that belief into a reality. Before Wyndy, my wife and I (like millions of other parents) could rarely accept invitations to go out with friends because of how difficult it was for us to find a babysitter for our two daughters, particularly if the invitation was last minute. But Wyndy is doing a lot more than simply giving parents a chance to enjoy a night out with friends.  We’ve heard from parents who, because of Wyndy, have accepted full-time job offers they previously turned down because they now have a reliable method for obtaining child care. We’ve heard from sitters who’ve told us they would have had to drop out of college had they not been able to generate the extra income they’ve earned working as a Wyndy. For all the challenges associated with starting a company, seeing users’ worlds change for the better makes it all worth it.
  1. Invest in Yourself. As a founder and CEO, investing in your health (physical, mental, spiritual, and emotional) is investing in your company’s success. That is easy to say, but hard to really believe, especially when you have investors who’ve given you their hard-earned cash and mandated that you to make it grow.  It can be easy to think that your personal well-being must be sacrificed in the short-term while you’re trying to build and grow your business. The reality, however, is that a founder who burns out after twelve months can’t deliver the kinds of returns that investors want. I have to remind myself almost daily that taking care of myself is the best way to take care of my business.
  1. Ask for Advice Early and Often. As a first-time founder and CEO, there were many things I knew little to nothing about when we started Wyndy. It took some time for me to work up the nerve to ask for advice from more seasoned entrepreneurs. They all seemed super busy and I was sure they wouldn’t make time for me. To my pleasant surprise, when I finally began reaching out, almost all of them took the time to share their wisdom, experience, and insight. I wish I’d had the humility and the courage to begin asking for advice sooner than I did.
  1. Learn to Prioritize. In a startup, it seems there are constantly more things to do than there is time to do them. As your team grows, it becomes increasingly important to focus on prioritizing initiatives and identifying for yourself and your team members the two or three most critical tasks to work on in a given day, week, or month.  
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