Keeping Small Businesses Competitive through Sharing Best Practices of Global Leaders

Margot Rutledge’s BIO

Margot Rutledge, the founder of KidsWin and Chief Encourager, is an accomplished facilitator, trainer, coach and author of Please Encourage Me. Her passion, which grew out of personal experience, is to help children and teens realize their value and reach their potential. She has worked with thousands of children, educators and other youth serving professionals to help young people thrive.

Prior to founding KidsWin, she worked for national workforce development firms and training organizations in the capacity of sales, operations, trainer and coach. Her passion is to help young people develop a high sense of self-efficacy and the skills necessary to lead successful and purposeful lives. In addition to her more recent work as a facilitator and coach, she has a background in nutrition counseling, a degree in Foods and Nutrition and became a Registered Dietitian following a Dietetic and Nutrition Internship at Massachusetts General Hospital. She is a native of New England and currently resides in Westborough, Massachusetts.


1. Please share with us what prompted you to create KidsWin?

Margot: My passion for helping children and teens grew out of personal experience. As a teenager and young adult, I doubted myself and wondered if I had the ability to achieve my dreams. Then I had the opportunity to participate in experiences that allowed me to take risks in a safe and supportive environment, in the presence of strong and caring mentors, and I developed skills and competencies I had never thought possible. I began to believe in myself and in my ability to accomplish anything I set my mind to. I founded KidsWin to give to children and teens what it took me until I was twenty-eight years old to begin to feel and experience.


2. There is no typical day in the life of an entrepreneur. Please share with us a sample of your day, start to finish.

Margot: You are so right. There is no typical day in the life of an entrepreneur. I’m an early riser, at my computer by 7 AM, often working (it’s not really working!) way past five. My day consists of writing, researching organizations where I can add value and reaching out to these organizations to see how we might work together to help children and teens thrive. On the days I am fortunate to be in front of educators, mentors and others who serve kids, I share tools and strategies and a coaching model they can use to help children and teens realize their value and their potential.


3. What are your ‘can’t live without’ Smartphone or desktop applications?

Margot: Immediate access to email via my smart phone and IPAD.


4. What are your tricks for time management?

Margot: I use Sage Act as a contact management system allowing me to keep track of all activity quickly and easily. It also allows me to schedule and prioritize activities.


5. What was the best advice you received when you started your career?

Margot: The best advice I received when starting my career was that attitude is everything. We are not born a sales person or professional of any kind; we become one through knowledge and experience. What makes the most difference in our success and happiness is our attitude. It is the one thing we can control.


6. Given the current economic climate, what has been your strategy for building awareness of KidsWin for short term and long term growth?

Margot: It has not been easy. Money is tight for most if not all youth serving organizations; yet this is where my heart is – helping kids. My strategy is to create and share tools & strategies, many of them free and to use social media and old fashioned word of mouth to spread the word. I recently published an ebook entitled Please Encourage Me to share a framework for coaching, mentoring and guiding children and teens that is easy to remember and can be used immediately. Cost is always an issue and I don’t want cost to be a barrier preventing anyone who works with children from having tools that will support their efforts.


7. What is your proudest achievement as an accomplished entrepreneur?

Margot: My proudest achievement is founding KidsWin – not an easy task to start a charitable 501(c))3 organization.


8. How do you achieve balance in your life?

Margot: Being a mom! Before having my son, I found it difficult to achieve balance and worked much of the time. Once I was blessed to have Luke, I have been much better at setting limits for my work.


9. Your top 3 book recommendations?

Margot: This changes depending on when you ask. One of my favorites of all time is

  1. The Greatest Salesman in the World by Og Mandino and I also highly recommend:
  2. Resonate by Nancy Durarte
  3. Until Tuesday by Luis Carlos Montalván


10. What are your most rewarding charitable involvements?

Margot: My most rewarding involvement is being a Big Sister through the Big Brother Big Sister organization.


11. Who has influenced your career the most?

Margot: I will share “what” instead of “who”. My experience working for the Dale Carnegie Organization influenced not only my desire to do what I do but my ability to undertake the challenge of KidsWin.


12. What is your advice for someone interested in entrepreneurship?

Margot: Be sure to do work you love because there will be difficult times. If you are working on a true passion, you will never, ever, ever give up!

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