Startups in Stilettos

Test Before You Invest with Deb Boulanger of The Great Do-Over


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After a successful corporate career, Deb Boulanger took time off to find her next steps. Three years later she realized her passion was in helping women do what she did: reinvent themselves midlife. 


In today’s episode, we sit down with Deb Boulanger, founder of The Great Do-Over, a company that helps women on their quest of entrepreneurship. Deb shares with us how she realized her passion in helping women launch businesses, the challenges she sees founders face, how to set your prices, and so much more. 


“The message was, ‘you need to teach other women how to reinvent themselves, just like you've reinvented yourself.’” - Deb Boulanger


This week on Startups in Stilettos:

  • Deb shares her background in Corporate America and when she knew it was time to go out on her own (2:38)
  • Deb explains what The Great Do-Over and The Launch Lab are (9:12)
  • Deb talks about the challenges she sees business owners face when they transition from corporate to entrepreneurship (13:24)
  • Why Deb steers clear of automated social media tools (16:35)
  • Deb shares how to price your services [this is a must listen] (19:34)
  • Stephanie and Deb talk about how to make social media work for you (24:42)
  • Deb tells us what we can expect to see from her in the coming year (28:53)

  • Resources Mentioned:

    • LeadPages
    • TheGreatDoOver.com/Pricing
    • Instagram

    • Our Favorite Quotes:

      • “So I'm an accidental entrepreneur. It was never in my experience. It was never in my DNA.” - Deb Boulanger
      • “I still love launching things. I love the marketing. I love understanding what are the hidden needs in the market that no one is serving or no one is serving well, and how do we create a service offering around that.” - Deb Boulanger
      • “So your network rallies around you, they're cheering you on, they're sending you people, and you can hit success really quickly, that first year, but then that warm network dries up. And if you don't have the systems and processes in place to really drive growth, then you start struggling and then it gets scary.” - Deb Boulanger
      • “Double your prices and see what happens because most women entrepreneurs are underpricing their services, because they undervalue their impact. And I can't tell you how many stories I have about my clients in the Six Figure Accelerator who have increased their prices by 50%, or sometimes 100%. And it's had no negative impact on their sales.” - Deb Boulanger

      • Connect with Deb Boulanger:

        • Deb on LinkedIn
        • Deb on Instagram
        • Deb on Facebook
        • TheGreatDoOver.com

        • Connect with your Startups in Stilettos hosts:

          • Stephanie Cartin on Instagram
          • Stephanie Cartin on LinkedIn
          • Jessica Abo on Instagram
          • Jessica Abo on LinkedIn
          • Learn more about Jessica Abo here

          • Get Featured on Startups in Stilettos

            Want a chance to be featured on Startups in Stilettos? We’re currently accepting applications from our Entreprenista League members to be featured on the show! Think of the Entreprenista League as your team members in what can be a lonely startup founder’s journey. You’ll have access to a private community of like-minded female startup founders who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our website, social channels – and, of course, the Startups in Stilettos podcast – and so much MORE!


            Join the Entreprenista League today at entreprenista.com/join. We can’t wait to welcome you, support you, and be part of your business journey!


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