Alright – so today we’ve got the honor of introducing you to Tailor Simpson. We think you’ll enjoy our conversation, we’ve shared it below.
Tailor, so good to have you with us today. We’ve always been impressed with folks who have a very clear sense of purpose and so maybe we can jump right in and talk about how you found your purpose?
My 10+ years of teaching early childhood education helped me discover my purpose by showing me the joy of nurturing young minds and fostering growth. Growing up in Oak Cliff with my Nana, visiting the candy lady’s house also inspired my creativity and passion for bringing happiness to others.


Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
I run a Kool-Aid pickle business called “Tailor Made,” inspired by my childhood in Oak Cliff and my 10+ years in early childhood education. My passion extends beyond creating treats; I also connect with the students and children in my life, teaching them how I started my business. It’s important to me to inspire them and show how creativity and dedication can turn ideas into something real. I’m excited to continue growing my business, introducing new flavors, and offering special packages for events, all while fostering a love for entrepreneurship in the next generation.


There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Creativity: My ability to think outside the box, whether in teaching or starting my business, has been key. Creativity helped me connect with kids and develop my Kool-Aid pickle business into something unique.
Resilience: The journey hasn’t always been easy, but staying resilient through challenges has helped me keep pushing forward and turning obstacles into opportunities.
Connection: Building relationships with the children I teach, and the community has been essential. I’ve learned that connecting with others, whether students or customers, makes all the difference in growth and success.


Before we go, maybe you can tell us a bit about your parents and what you feel was the most impactful thing they did for you?
The most impactful thing my parents did for me was when my grandmother stepped in to raise me during a difficult time. My mom was going through a challenging relationship with my father, but my granny came and saved me, showing me love and raising me to be the woman I am today. Later, when my mom came back into my life, we reconnected before she passed away from breast cancer. Both of them are no longer here, but they are definitely my “why.” Their love, strength, and sacrifices continue to inspire everything I do.
Contact Info:
- Facebook: Tailor Simpson
- Youtube: @TTfamilyacademy
- Other: tiktok: Tailormade_justforyou


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