Boss Up

How to Become a Rising Star Entrepreneur

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Get ready to move up to that corner office or start your own enterprise. is partnering with the award-winning The BOSS Network to bring you BOSS UP every week. This feature will highlight movers, shakers and rule-breakers across different industries, plus offer you career and entrepreneurial advice.

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The summer before I started graduate school, I worked as a nanny for several families in the Washington, D.C. area. I had been a nanny before and caring for children was an amazing extension of my classroom career. That summer, however, was a tough one: Two of the children in my care were both on the autism spectrum and I couldn’t find many resources that helped me learn what I needed to help them.

The summer was both a mixture of fun, joy, panic attacks, possible epileptic seizures, and ambulance rides. It left me wondering if I had made a positive difference in the lives of the children I cared so much about.

During graduate school at Harvard, I began researching to see if there was a resource that would empower child caregivers to provide the best for the children in their care. Life’s hardest challenges can often become the best opportunities for the entrepreneur in you to shine through. That’s when was born. At, we seek to enhance the lives of families and nannies through supportive childcare education, resources, and community.

Read on to discover tips that can help you become a successful entrepreneur:

Put one foot in front of the other

With the rise of online education, I knew that it was possible to serve up classes that would help nannies and families meet their own day-to-day challenges and share their successes as caregivers. By 2012, I began working on creating webinars to test out the market for creating classes for nannies. The following year, I took a leap of faith and started a business accelerator program to begin learning how to develop SitterCycle full time.

Since founding the company, I have taken on more roles than I could have ever imagined. I’ve been the producer, the visionary, the content editor, the sales person — and of course, the trainer. There are days where I get so out of my comfort zone in these roles that I wonder if I’m on the right path. As my Dad always reminds me, “even on those days that you’re biting on fingernails wondering what is going to happen next, keep going because you may surprise yourself and trust in God for the strength to put one foot in front of the other.” At 29, I never imagined that my life would be so challenging and yet so fulfilling. I love the fact that our classes have the potential to change the lives of professional caregivers as well as the families whose lives they share.

You’re pitching everyone — including yourself

After some strategic conversations with advisers and mentors, we listened to our nannies and have embarked on an ambitious path to creating more classes that would serve the needs of nannies in a wide range of topics including infant care and nutrition that weren’t part of my own expertise. This meant that instead of just pitching customers and investors, I had to pitch content experts, such as doctors and nutritionists about the vision of the company. More importantly, I had to prove I was capable of building the kind of company that could empower nannies and families. The life of an entrepreneur is not just about convincing and selling the vision; so much of the first battles of an early-stage entrepreneur have been about bringing on the first employees, the first agencies, and our most important test — the nannies and families with the vision of what we hope to build at SitterCycle. That sometimes meant that I had to convince myself, especially when the road seemed long and rough.

Imagine it even when it isn’t there yet

My favorite part about being the founder and CEO of is creating classes that our nannies love and find very helpful. With our new classes coming down the road, we’re eager to prove that they raise both the confidence and skillsets of our nannies. The early results and our first surveys have been positive, but I imagine our start-up doing much more. The vision of our company is that in three or five years (or sooner), we will be the go-to destination for caregivers who have come to improve or learn new skills. One of the biggest lessons I have learned is that you must see and be protective of the vision that you have for yourself as an entrepreneur — even when the bills come and you’re down to your last dollars. Have faith in your vision to keep you going.

About Helen Adeosun

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Helen Adeosun is passionate about children! The year before starting SitterCycle, she was hired by a wonderful family that had two children with special needs who taught her so much. While she had experience with special-needs children and had classroom experience, she knew that she still had a lot to learn. Helen holds a B.A. from the University of Notre Dame and an EdM. from the Harvard Graduate School of Education.

Follow BOSS Helen on Twitter @hadeosun and view her website

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