Meet Windy Oler | Custom Cookier

We had the good fortune of connecting with Windy Oler and we’ve shared our conversation below.

Hi Windy, every day, we about how much execution matters, but we think ideas matter as well. How did you come up with the idea for your business?
It just kind of happened naturally. I had never thought of starting a cookie business (my original goal was photography). I started making decorated cookies for holidays and just fell in love with it. I would make cookies for any holiday or event (any excuses to bake I took), then people started to ask for my cookies. I started toying with the idea of turning my love of decorated cookies in to a business. I came up with the name (the MK is my daughters name shortened and the J is my sons initial), but still very hesitant about actually going from hobby to business. My brother and sister-in-law asked if I would make cookies for my nephew’s first birthday, and when I arrived at the party, my sister-in-law had made business cards for me. That’s when I decided to take a leap and make it more than just a hobby.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I think I am most proud of how far I’ve come. I’m a single mom, I work full time and I’m trying to grow a business where I’m doing something I really love. Trying to juggle everything by myself is very challenging at times but its also very rewarding. I’m still learning how to find balance between all three.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I would start by taking them to Southlake square, that is one of my favorite places to just hang out and walk around. So many shops and great places to eat. Grapevine main street is another great place to hang out, very unique shops and restaurants. It has that old world, its a great historical spot. The Dallas arboretum, especially in the fall when the pumpkin village, its so beautiful and peaceful. Farmers markets on the weekends are my absolute favorite thing to do, I love supporting other small business and talking to the owners.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I want to recognize all my friends and family. Everyone in my life has been incredibly supportive! From encouraging me to start my journey in baking and cookies, to late nights packaging orders, or just keeping me company. My brother, Mike, is always there when I need business advice. My friend, Ashley, always comes over when I am in a pinch to help with preparation for events. My friend, Becca, attends events with me to keep me company, but has also helped me come out of my shell and be more talkative with customers as they come by my table. I honestly would have hidden under my table if it wasn’t for Becca (I am painfully shy)!

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