We recently connected with Jennifer Massoll and have shared our conversation below.
Alright, Jennifer thanks for taking the time to share your stories and insights with us today. What was it like going from idea to execution? Can you share some of the backstory and some of the major steps or milestones?
Many people have great ideas, but taking the extra step to act on one is often the hardest part. Big Island Bouldering has been a true team effort from the very beginning. Five families came together to turn the idea of a local climbing gym into a reality. We shared a love for climbing and the strong sense of community it creates. As neighbors, there were countless ways we could have spent time together, but the positive energy and camaraderie of climbing was impossible to ignore.
With the nearest climbing gyms 25–45 minutes away depending on traffic, we were highly motivated to create a more convenient option close to home. Once the idea of opening our own gym was on the table, we had to ask ourselves whether we were ready to fully commit. Building a business from the ground up is no small feat. From construction and working with climbing-industry vendors to hiring and training staff to ensure an exceptional customer experience, the process was both challenging and rewarding.
We’ve been incredibly fortunate to meet, work with, and continue to collaborate with amazing people along the way. It turns out that when you come together around a shared vision and genuine passion, others are eager to help you succeed. We’re proud to have just celebrated our first year in business!

Jennifer, 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?
I’m an artist by trade, so the creative process of developing a name, logo, and color palette genuinely excited me. But let me tell you, building a brand is about so much more than those surface elements. Creating the Big Island Bouldering brand required us to ask some big questions: What is our purpose? Who is our audience? What is our personality? How do we differentiate ourselves? What role do we play in the community? What visual experience do we want to create? And when someone leaves our gym, how do we want them to feel?
We knew from the beginning that we wanted to create a space where everyone feels welcome and encouraged to try. Bouldering can be intimidating, and taking that first step into the gym should be the easiest part. Our staff strives to be warm and encouraging, and our routesetters create thoughtful, inspiring problems just waiting to become someone’s next project. More than anything, our team wants people to feel good, both when they walk through our doors and when they leave.
I’m proud of what we’ve built and what we continue to create alongside our owners, staff and climbing community.

What do you think helped you build your reputation within your market?
Word of mouth has been our most powerful form of growth. There’s nothing more meaningful than a customer sharing a positive experience with friends or family. Many of our new climbers tell us they first heard about Big Island Bouldering through a recommendation from someone they trust, and that kind of support means everything to us.
We actively encourage feedback from our community so we can continue improving our space and the experience we offer. People choose to spend their time here and as we all know, time is a precious gift. Being able to share that time with family, longtime friends, and new connections in our gym is a privilege we never take for granted.

Can you tell us the story behind how you met your business partner?
I met my partner in business and in life while attending Texas A&M. We’ve lived in 4 different states and many different homes along the way. We’ve been fortunate to meet our other investors, first as neighbors, then friends and now business partners. Between us, we have kids of all ages and some of them even work at the gym.
We are all deeply invested in the gym and the community it serves. Building this business has been, and continues to be, a shared learning experience. Each family brings different abilities, backgrounds, and interests, all of which contribute to making the gym stronger and more well-rounded.
Contact Info:
- Website: www.bigislandbouldering.com, www.artbyjdm.com
- Instagram: @bigislandbouldering, @artbyjdm
- Facebook: @BigIslandBouldering



