Today we’d like to introduce you to Caroline Carr.
Hi Caroline, please kick things off for us with an introduction to yourself and your story.
Maddy’s Cream Bike came out of a chapter of my life I never could have predicted.
I spent most of my career in finance and accounting, including public accounting, corporate finance at Nike, and later working with technology startups. I loved the business side of my career, but becoming a mom changed the way I thought about work, time and what I wanted the next chapter of my life to look like.
My daughter Maddy was a big part of that shift. I found myself wanting to build something that felt joyful, creative and tangible, something that could bring people together and become part of their celebrations and memories.
That idea eventually became Maddy’s Cream Bike.
We make handcrafted ice cream sandwiches in small batches and serve them from our signature vintage-inspired Cream Bike at weddings, corporate gatherings, conferences, nonprofit events and celebrations throughout the Portland area. The bike itself has become a big part of the experience. People naturally gather around it, take photos, talk to one another and get excited about choosing their flavor.
What surprised me most was realizing that we weren’t just serving ice cream. We were creating a little moment inside an event.
Sometimes you can actually see the change in people when the bike rolls in. Adults suddenly light up like kids again. Someone recognizes a flavor they loved growing up. Coworkers who may not normally talk to each other are standing around comparing ice cream sandwich flavors. At weddings, guests come over together and take pictures. Those little interactions are some of my favorite parts of the business.
We launched our first season in 2025, and since then I’ve learned an enormous amount about the events and hospitality world. We’ve had the opportunity to serve companies, universities, community organizations, weddings and large regional events. We’ve also expanded beyond the bike with cooler drop-off options for clients who want the same handcrafted treats for smaller office celebrations, meetings and gatherings.
One of the things I love most about building Maddy’s is the community around it. Portland has such a strong network of event professionals, venues, small-business owners and organizations that genuinely want to support one another. So many opportunities have come from a conversation, an introduction or someone simply saying, “You should meet this person.”
I also came into this business without a traditional culinary or hospitality background. My background is finance, so naturally I think a lot about the economics and systems behind the company. But this business has also pushed me into a much more creative world. I’m learning about hospitality, event design, baking, flavors, production, branding and how people experience a moment.
Ultimately, I want Maddy’s Cream Bike to grow into a company that is known for creating joyful, memorable experiences around gatherings. Life moves quickly, and events can too. I love the idea that something as simple as a really delicious ice cream sandwich can give people a reason to slow down for a moment, gather together and enjoy something special. Our treats are designed for occasions, for sharing, celebrating and creating those little moments people remember. Ice cream is the vehicle, but what we’re really creating is connection, nostalgia and joy.
And the funniest part is that Maddy is still young enough that she doesn’t fully understand there is a business named after her. Someday I hope she looks back and knows that she inspired me to take a chance on a completely different chapter of my life.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
One of the biggest challenges has been learning how to turn a creative idea into a sustainable business.
When you first start something, it is very easy to focus on the parts people see: the product, the branding, the beautiful bike and the event itself. But there is an enormous amount happening behind the scenes. Production, staffing, transportation, cold storage, event logistics, scheduling and customer communication all have to come together before a single ice cream sandwich is served.
I’ve also had to learn when to listen to the market instead of holding too tightly to my original vision.
For example, I originally imagined Maddy’s primarily around the Cream Bike experience. But clients repeatedly asked if they could have our ice cream sandwiches for smaller office celebrations or gatherings where bringing in the full bike didn’t make sense. That feedback eventually led us to develop our cooler drop-off options.
That was an important lesson for me. Sometimes your customers show you where the business should go.
Another challenge is figuring out how to grow without losing the things that make the company special. Our cookies are baked in small batches, the sandwiches are assembled and wrapped by hand, and there is a lot of care behind the experience. As we grow, I think constantly about how to build systems and a strong team while keeping that warmth and personality.
And personally, I’m building the company while raising a young daughter and being present for my family. That has made me much more aware of the kind of business I want to create. I don’t just want growth for the sake of growth. I want to build something sustainable, with a great team and systems that allow the company to grow without requiring me to be involved in every single detail forever.
There are definitely days when entrepreneurship feels slower or messier than I expected. But I’ve learned that almost every event and every customer conversation gives us another piece of information about what the business can become.
We’ve been impressed with Maddy’s Cream Bike, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
Maddy’s Cream Bike is a Portland-based event and catering company specializing in handcrafted ice cream sandwiches and joyful dessert experiences for corporate events, conferences, weddings, nonprofit gatherings and celebrations throughout the region.
Our signature Cream Bike brings a playful, nostalgic focal point to events, while our cooler drop-off options make it easy to bring Maddy’s to offices and smaller gatherings. Everything is centered around the idea of slowing down for a moment, enjoying something delicious, and creating memories together.
Where we are in life is often partly because of others. Who/what else deserves credit for how your story turned out?
My husband, Tyee, deserves a tremendous amount of credit. Building a business affects the whole family, and he has supported me through all of the excitement, uncertainty and very long event days. We both come from finance backgrounds, so he is also someone I can talk through the numbers and business decisions with when I need another perspective.
I’m incredibly grateful for the small team that helps make Maddy’s possible. What guests see at an event is the finished experience, but there are hours of baking, assembling, wrapping, packing, loading, transporting and setting up behind it. Our team brings so much care to that work.
I’m also incredibly thankful for Portland’s event and hospitality community. Event planners, venues, photographers, fellow small-business owners and clients have introduced us to people, recommended us, shared our work and trusted a young business with meaningful events. So much of our growth has come through relationships, people believing in what we’re building, making introductions and opening doors for us.
And of course, Maddy deserves some credit too. She is the reason the business exists in the first place. Becoming her mom gave me the courage to imagine a completely different chapter of my career.
Contact Info:
- Website: https://www.maddyscreambike.com
- Instagram: https://www.instagram.com/maddyscreambike/
- Facebook: https://www.facebook.com/profile.php?id=61570810093626
- LinkedIn: https://www.linkedin.com/in/caroline-carr-mcb/?utm_source=chatgpt.com
- Yelp: https://maps.app.goo.gl/Cr7689EWobgJYUF96
