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“My biggest risk was leaving a comfortable job to do something that hadn’t been done before.” – Tamiko Kelly, Sleep Well. Wake Happy.

November 10, 2015

The Hiscox “MyStartUpStory” series features entrepreneurs offering small business advice and discussing their own start-up experiences. We recently met with Hiscox Customer Tamiko Kelly, who runs a children’s sleep consulting business, Sleep Well. Wake Happy. For Tamiko, entrepreneurship is a family value… but she didn’t embrace it at first. Find out how she left her comfortable corporate job to following her passion when her clients just wouldn’t let her say ‘no’.

Hiscox: What made you want to become an entrepreneur?
Tamiko:
Well, I come from a long line of entrepreneurs – you might even say that I have entrepreneurship in my blood. Growing up in Houston, Texas, my grandparents owned a grocery store and while my parents both had full-time jobs they both also had what we called “side-hustles”, or part -time entrepreneurial endeavors. So, I knew from an early age that I wanted to have my own business. I just didn’t know what it was going to be.

I think entrepreneurs are born with a special spark that enables them to see things that other people cannot see. Many people are told that they need to follow a traditional path – go to school and get a job after that, and trust me. I tried that but it didn’t for me.  I was miserable.  It took me being pushed to the edge in order to finally accept what I knew all along, I was made to be an entrepreneur.

Hiscox: Taking risks is one of the 10 Important Characteristics of an Entrepreneur. What was the biggest risk that you took to start your small business?
Tamiko:
My biggest risk was leaving a comfortable corporate job to do something that hadn’t been done before. I had a great career doing visual merchandising for large corporations, but I was frustrated because it was not perfect for me. On the side, I worked as a “date night nanny”, enabling parents to have a night out together while I watched their kids. My clients noticed that I had a knack for something they sometimes struggled with –helping their kids go to sleep, that’s how ‘Sleep Well. Wake Happy’ was born.

That fear of wondering if things wouldn’t work was constant. When I left my job I had literally no money saved and I was terrified. But it turned out that quitting my job was the best move I could have made. Within 48 hours of resigning, I had $20,000 in business. That fear of not being able to make it work was gone.  I realized that my clients needed me and they just wouldn’t let me say ‘no’.

What was the hardest part about starting your small business?
Tamiko: Undoubtedly, the pressure of having to duplicate success month after month.  You get concerned that you will fall flat on your face. To get over it, I continue to do what I’ve always done – provide an excellent, life changing service to my clients.

What advice do you have for people who are thinking of starting a business, but haven’t made the leap?
Tamiko: When you’re starting out, it’s important to surround yourself with a community of entrepreneurs. Sometimes your friends with typical 9-5 jobs won’t understand what it’s like to not have “the safety net” of a corporate job. Having an entrepreneur community can help you stay positive in tough times.

I also encourage everyone to figure out their ‘why’ when they are thinking about starting their small business. “I want to help people” is a very vague reason to start a small business. Find the deeper, emotional reason. Is it because you want to take care of your aging parent, have freedom or send your children to private school? Then go even deeper, what would it mean for you to be able to take care of your aging parent, have freedom or send your children to private school? Having these specific reasons written down is all the personal motivation you need to start your small business.

Finally, present what you have to the world and continue to work on refining it. Just getting out there is the first step. If you want to be successful, you need to do some research. Talk to people. Figure out what their pain points are. This will help you figure out how to market your business and make it easier for them to say ‘yes’ when you offer your business to them.

How important is courage for small business owners?
Tamiko: Courage is very important. It’s up there with tenancy and drive. You have to have courage to leave a comfortable life to do something others will never do.

What’s next for you and your company?
Tamiko:
In 2016 I plan to start offering coaching to business owners who are struggling with monetizing their ideas.  I’m still working on what this will look like, but I’m excited about it!

I’m also working on a program which will be designed to teach tired moms how to get their babies to take longer naps.  I have some ideas about a toddler sleep program.  So 2016 will be an exciting time for Sleep Well. Wake Happy.

Do you have professional liability insurance and why do you think it is/is not important?
Tamiko: Yes, I have professional liability insurance. For me, it’s because of the nature of my business. I go into people’s homes and because I’m in contact with small, beautiful babies, it’s important to make sure that I’m covered.

As a baby sleep expert, tell us, what is the most important thing about getting a kid to sleep?
Tamiko: My top tip is to put your child to bed at the first sign of sleepiness. Sometimes parents wait too long and then the child becomes become over-tired, which leads to meltdowns at bed time where children cry on end. However, if you get them into bed a bit earlier you’ll be surprised at how easily they’ll fall asleep


  • Amber Mayhew

    Tamiko is such a smart business woman! I love every chance I get to network with her. I have had the chance to work close to her for years and she has a true passion for what she does.

    • Hiscox Blog

      Her passion is an inspiration to us all, Amber! Thanks for your comment!

    • Hiscox Blog

      We couldn’t agree more! She’s a savvy, smart business woman and we’re happy to feature her story!

    • Amber thanks so much for your wonderful words of encouragement. I too consider it my unique pleasure to have gotten to know you over the years. It’s so great to see all my lady bosses with flourishing businesses. Yay!

  • maJOY

    What an amazing article full of the very questions/answers I have been pondering these past few days. Tamiko is a tremendous source of inspiration for my own entrepreneurial journey.

    • Hiscox Blog

      Thanks for your comment, Mary! We’re so proud of Tamiko and are happy to have her as one of our small business clients!

    • Thanks MaJoy! I’m so glad that my article resonated with you. Thanks for your continued support.

  • Liz S

    Its wonderful to see a woman taking charge of her life and realize her dreams. As another minority woman I applaud you. And as a mommy of two little ones I am well aware of how important baby sleep is for the baby and the mommy! Crucially important! Congrats and heres to an awesome 2016 for you!

    • Hey Liz! Doing what others are afraid to do is the only way to realize your dreams. It’s super scary but so worth it! And yes sleep is so important for the entire family. Thanks for your support and I wish you and your family the best in 2016.

  • Aww Jenny that’s awesome! Way to take action! 3 cheers for long naps 🙂 Thank you so much for attending my event yesterday. It was such a pleasure meeting you and your little guy.

  • Michael Richardson

    Thanks for the article. My virtual support network helps keep me going. Look forward to your 2016 monetization projects!

    • Thanks so much Michael! It’s such an exciting time for my business!

    • Hiscox Blog

      Hi Michae, thanks for your comment! There’s no replacement for having a network of people that can help you stay motivated when the times are tough!

  • Jen Bourgoyne

    Very inspirational. I’ve seen her speak on television and you can tell she’s a genuine and good person who loves what she does. Those are the best kinds of entrepreneurs!

    • Hi there Jen! Thanks for your kind words. Happy to hear that my story was an inspiration to you. #ladybossesrock

  • Dr. Kitt

    As a graduate of Smith College, I commend Tamiko Kelly on being a woman of distinction. Entrepreneurship knows no boundaries and Miss Kelly is living proof that dreams can become realities. Having seen the birth of SWWH and its wonderful path to where it is today, I can honestly say that I am anxiously awaiting Ms. Kelly’s next foray into business coaching.

    • Thank you Dr. Kitt for your wonderful compliments. Yes dreams can totally come true. I’m blessed to be living the life of my dreams. God is good and I am forever grateful

  • Tonya Sakowicz

    I know Tamiko and she is one smart woman! I have no doubt her business coaching will be a great success.

  • Kevin Keltner

    I really enjoyed reading your article. It’s very inspiring. Your a lady on a mission and I can’t wait to see what you have up your sleeve. I can’t tell you how proud I am to call you my friend. Have a wonderful 2016.

    • Lady on a mission…I love that! Yes girl 2016 is our year! Hugs all around 🙂

  • connie Curtis

    Awesome story. It inspires me to keep pushing forward. I know where to find you if I need help as a coach too. Right now things are flowing..

    • Connie!! So great to see your comment. Yep keep moving forward. Your success is full steam ahead!

  • Jennifer Farr

    I am so proud of you. I don’t even know you, but I try to tell my children (I have 3 girls) not to let f.e.a.r. control their life. You are the perfect example. May God continue to work thru you to reach parents who need your help. Enjoy the day. #newestfan