Meet Jessica Montgomery

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

Hi Jessica, we’d love to hear about how you approach risk and risk-taking.
Risk is essential, you don’t know what you’re capable of until you try. When I first started my cookie business, I had no idea where it would lead me, let alone if I would be successful or not. My first custom cookie order was for a friend’s bridal shower, and after a few more orders, friends and family began to encourage me, seeing potential for something more. I created an Instagram page to share my work, and the positive response and incoming orders confirmed that there was a market for what I was doing. That’s when I made the decision to officially invest in the business. Taking that initial risk was crucial, it allowed me to step outside of my comfort zone and pursue something that started out as a fun pandemic outlet. Since then, I’ve taken more risks, whether it’s experimenting with new designs, selling at local markets, and a full rebrand. Each risk has brought its own set of challenges, but it’s also helped me grow as a baker and an entrepreneur. At the end of the day, each time you try something new, you might be saying “yes” to something you’ll end up loving.

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.
Balancing my cookie business with my full-time career has definitely been a journey. By day, I’m an environmental planner working in local government, and after 4 p.m., I’m a creative cookie artist. It’s a lot of work! The structure of my day job helps me stay organized and disciplined, while my business gives me an outlet to express myself in a totally different way. The journey hasn’t been easy. There were plenty of times I wanted to stop baking, especially since I’m not an expert in marketing or running a business. Becoming a new mom was also a huge challenge, but it gave me even more drive to keep going. I started selling at local markets to get my name out there and that was a big step. Every new challenge has helped me grow, as a business owner and as a person. I’m proud of myself for that. The biggest lesson I’ve learned is that growth takes time and resilience. It’s okay to not have everything figured out right away. What I want people to know about my brand is that it’s more than just cookies, it’s a reflection of my journey. Every design is custom for a client’s celebration, but also a little piece of me. I hope my story shows that with perseverance you can balance multiple dreams and make them work, even when the path isn’t always clear.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I’m a San Diego native and I love my city! For visitors coming into town, I love taking them to Torrey Pines Gliderport to watch the paragliders, enjoy the views and grabbing lunch at Cliff Hanger Cafe. Another go-to spot that I love for local and fresh eats is Mitch’s Seafood. After that, I love exploring and bar hoping North Park. For a fancier experience, I love Polite Provisions for their craft cocktails and swanky atmosphere.

Who else deserves some credit and recognition?
My family and friends that I call family. They encouraged me when I was unsure and believed in my vision even when I didn’t fully see it myself. I also want to give big props to the incredible community of cookie artists and bakers who share tips, support, and inspiration, it’s been such a valuable resource as a self-taught cookier.

Instagram: Icedbyjess

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