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37 Oaks' Small Business Spotlight Meet Yolanda McCray

Updated: Jun 27

Shining a light on the amazing small business owners that power the communities we live, work, and play in.

37 Oaks has the opportunity to work with some of the most amazing small business owners around the country. They start with a passion or a hobby, then we guide them towards growth. Let's take a moment to shine a light on the rock stars!

37 Oaks Small Business Spotlight
Owner, Yolanda McCray

| 1. Tell Us About Your Business

Skyler M empowers women 25+ to live beautifully inside and out. We're more than just an online boutique and pop-up shop offering clothing, accessories, and custom gifts. We take a whole-woman approach, providing style consulting, health, and wellness education alongside our curated collections.

| 2. What Makes Your Business Unique?

What makes us unique is our whole-woman approach. We empower women to look good with our products and be emotionally healthy, encouraging them to take care of their physical bodies. We believe spiritual health is the foundation of well-being, and we share the message of Christ with those who want to learn more.

| 3. What Inspired You to Start Your Business?

My love for clothing and accessories, coupled with my background as a licensed social worker and evangelist, fueled my desire to start Skyler M. I've always dreamed of owning a business that could combine these passions to empower women through a whole-woman approach. Skyler M, named after my beloved Cocker Spaniel who passed away from cancer in 2019, reflects the inspiration I found in all the things I love: helping people, sharing my faith, and offering beautiful products.

| 4. Describe The Challenges Faced In Taking Your Business From A Hobby Into the Early Growth Stage.

The challenges I've faced in transitioning Skyler M from a hobby to a business has been finding a work-life balance while wearing all the hats – social worker, evangelist, and entrepreneur. It's a demanding juggling act.

Also, securing funding has been an obstacle, as I bootstrapped the business with my own savings. Despite these challenges, my belief in Skyler M's mission, I love what I do and the unique value we offer women keeps me pushing forward.

| 5. How Did 37 Oaks Help You Overcome These Challenges?

37 Oaks was a game-changer for Skyler M. I had the passion products and services but lacked the business knowledge. The FedEx E-Commerce Learning Lab ( a partnership between 37 Oaks + Accion Opportunity Fund) gave me a crash course in e-commerce, sales funnels, and identifying my ideal customer. Plus, the $5,000 grant helped with my marketing strategy.

But the real win was the support. The sessions helped me develop a pitch and marketing strategy, and the program boosted my confidence. They helped me see my fears and overcome them, and provided the ongoing encouragement I needed to keep growing Skyler M.

| 6. What Is Your Greatest Win So Far As A Small Business Owner?

My greatest win so far came from a repeat customer. This awesome woman reached out to express her love for both the products and my inspirational posts. She even shared her excitement about waiting for new merchandise to arrive. Moments like this, where customers become enthusiastic fans, are what truly make all the hard work worthwhile. Just getting that message made me believe I'm on the right path.

| 7. What Advice Would You Give An Early-Stage Entrepreneur Working To Grow Their Business?

For aspiring entrepreneurs, my biggest piece of advice is: never give up on your dreams! There are fantastic programs like 37 Oaks out there that can empower you to turn your vision into a thriving business. The key ingredients are believing you can and unwavering confidence in yourself and your venture. With those in place, the rest will follow.

| 8. What's Next For Your Business?

Skyler M has exciting things brewing over the next 6-12 months! We're launching curated subscription boxes packed with goodies to inspire beautiful living inside and out. Plus, I'm learning to sew and design a unique line of trendy, upcycled women's clothing. I'm super excited about this so stay tuned.

Support and connect with this small business at


Who's Next?

If you or a small business owner you know would like to be featured in our Small Business Spotlight, apply at



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