We caught up with the brilliant and insightful Madison O’Brien a few weeks ago and have shared our conversation below.

Madison, appreciate you joining us today. Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?

When I first started MadBeans, I could barely sew. I had made a few pieces of very unflattering clothing, hemmed another few items, and made one of the worst looking hats anyone had ever seen. Friends of mine knew I had “taken up” sewing, and asked if I could make the retro four-point beanies that MadBeans is now known for. I tried (and absolutely failed) on my first few attempts, but eventually came up with something that resembled headwear. My friends were so stoked about the results that I figured I’d keep making them. I live in a ski town, and the goofy four-point style really matched the energy out on the slopes. As more of my friends started wearing them, more people would ask about where they had gotten them. With so many people stoked about them, I decided to spread the love and start selling them online. It was really important to me that all the beanies had my logo on them, so I ordered a ton of woven patches and started branding each bean. At first, I would just put beanies up on my Etsy site as I made them. I realized quickly that things couldn’t go on like this because I was constantly juggling cutting fabric, sewing, taking product photos, and posting listings. A month or two into selling on Etsy I decided to make the switch to selling in drops. I would hype up the drop on my Instagram so that my followers would get excited about the new beans that would be available, and the weeks leading to the drop gave me the time to prepare one step at a time. I wasn’t sure about making this transition at first, but it was honestly the best change. Making the beanies only available for purchase one night every few weeks also really increased demand. My drops started selling out in less than 10 minutes, which was a huge turning point for MadBeans.

Madison, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

MadBeans Beanies is where functional meets fun! We specialize in the sale of retro four-point fleece beanies that have captured the hearts of the skiing and snowboarding community. Each beanie is lovingly handmade up in the mountains in Colorado. My name is Madison O’Brien and I am the founder of MadBeans! My vision was to cultivate a small business that is all about embracing individuality, encouraging connection, and staying stylish through it all. I love creating headwear that is unique and fun and stands out. I also love living in the mountains, and spending time outside. I wanted MadBeans to reflect that love as well, so I have pledged to donate part of its proceeds to Protect Our Winters (POW), a non-profit organization committed to helping passionate outdoor people protect the places and lifestyles they love from climate change.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I studied Environmental Science in college, and though I was really passionate about it, I didn’t quite know how my career would end up fitting within that box. I think as a woman, especially one who didn’t have an ounce of business experience, it can be really intimidating entering that space. I seemed to be under the impression that because I didn’t study business or marketing or have any experience in a field that I deemed “helpful” in starting a brand, I would fail. Since deciding to take on MadBeans, I have had to remind myself daily that I am still capable of learning things and being great at them. I know it seems silly, but sometimes I get it into my head that other people have so much more experience than me and therefore I won’t be successful. I still struggle to think of myself in terms of a business woman, but I have learned so much over this past year and am so glad I didn’t let that fear stop me from taking that initial plunge.

Have you ever had to pivot?

There were a few months in between when I started sewing my signature beanies and when I decided to really try to build a brand. I had been working as a waitress at a restaurant in one of the ski villages and was feeling ready for a change. I had been applying to jobs, but wasn’t really feeling passionate about anything. In all of my free time I wanted to pick out fun fabric, and sew, and post photos to the MadBeans Instagram. I was really struggling in the job application process because all I wanted to do was make goofy little hats. I was visiting family during this really transitional period and my dad took notice in this. We went out to breakfast one morning and he asked me if I felt like I could give MadBeans my all and focus on building a business instead of finding a 9 to 5. I lit up like I hadn’t in months, and knew that taking that risk would be worth it, even if it didn’t work out. I decided to keep my restaurant job and ended up working on MadBeans all day and waitressing all night. The winter was incredibly busy and I worked some exceptionally long days, but I loved every second of it. This transition was definitely scary, but I feel so grateful that I was able to pivot from job hunting to devoting myself to something that I am truly passionate about.

Contact Info:

• Website: madbeansbeanies.com
• Instagram: @madbeansbeanies
• Other: email: hello@madbeansbeanies