Season 2 Episode 008
Caroline Carr
What does it take to step away from a successful 20+ year corporate career as a finance executive and launch a business centered on creating moments of joy?
In this inspiring episode of Women’s Million Dollar Conversations, Alice Tang sits down with Caroline Carr, founder of Maddie’s Cream Bike—a Portland-based premium event hospitality company specializing in handcrafted ice cream sandwiches and memorable guest experiences.
Caroline shares her fascinating path from starting as a CPA at Price Waterhouse Coopers and serving as a finance leader at Nike, to navigating early-stage tech startups, and eventually hitting her pivotal milestone: stepping off the corporate ladder to build a legacy for her daughter, Maddie.
"Success to me is really giving myself the permission to utilize my skills in a different way, continue to reinvent myself, and deliver value to others."
Alice Tang: Today our guest is a young friend of mine, but she’s super successful when I met her, pre-pandemic, so I would say maybe 10 to 10 years. who’s counting? Nobody knows. Her name is Caroline Carr. over the time of our friendship, she has evolved into doing something that is more special than her super power when I first met her. Let’s welcome Caroline Carr.
Caroline Carr: Alice, thanks for having me on. I’m excited to chat today.
Alice Tang: Good. good. we love to have you, Caroline. Caroline, instead of the traditional reading the bio for five minutes, let the, audience know who are you, what you do, and other things that is important. So go.
Caroline Carr: Yeah, that’s great. Thank you, Alice. I am Caroline Carr. I’m the founder of Maddie’s Cream Bike. We are a Portland-based premium event hospitality company that specialize in handcraft ice cream sandwiches and memorable guest experiences. While the ice cream is what people see, our business is really about creating moments of joy and connections.
We partner with corporations, healthcare organizations, not-for-profit, venues, and private companies and hosts to really elevate their celebrations and employee appreciation experiences and conferences and gatherings in general. Yeah, before created this company, I was… I had a long career in, in finance and accounting.
I started out, as a CPA at, Grant Thornton and then moved on to Price Waterhouse Coopers. And then, after I kind of reached the manager level,I kind of had a career path, decision to make. Do I want to stay and make partner at these large firms, or do I venture out? And I actually ended up joining Nike.
And I was there for about five years. Great experiences, worked super hard, and also then after that I had another pivotal decision point to actually to join the technology startup world. Which I did, and that turned out to be just such a wonderful decision for me. Because at that point, I realized that I wasn’t very good with climbing,
I wasn’t very good with politics and while I loved the work, I always loved, the people that I work with. So I made the leap after 10 years in accounting, I kind of took the path to join technology startup and became kind of financial executive for early stage startup.
And I had so much fun doing that and just had a really rewarding career. And so that kind of sums up my last, like the last 10, 15 years of my, kind of tech leadership role. Throughout that time, I’ve met so many great people. The startup world have really inspired me and I learned so much.
When my dad passed away about four years ago, I really, had the opportunity to take the time off and really reflect . My parents are not gonna be around forever, and that really gave me a pause to really, rethink everything. And Ty and I were grateful to have the opportunity. We were very late already. I was already 44, 45, and really starting to think about maybe we need to take a break in our career and really think about our family.
We kinda took the chance to try to build a family and was very blessed to, go through the IVF process and to have a little girl, Maddie, at the age of 45. And that was really game-changing. I really didn’t realize what that mean until Maddie was born.
But I realized how life-changing this is, I decided that maybe it’s time for me to take a little different path.
It’s a season for me to really spend time with Maddie I feel like this few year is really precious, and maybe I can try creating something different. And so that’s kinda where this idea of, Maddie’s Cream Bike is born, doing private events and serving, hand-crafted ice cream sandwiches, at gatherings.
I always love bringing people together, and I know so much about startup and the idea of, failing, testing something, failing, learning, and redoing it, improving it. I don’t have a ton of expectation for this. I can take this step and kind of redefine what success look like in a non-traditional sense.
I have over two decades of experience and I really feel like this is the time for me to do something different. And so here we are.
Alice Tang: Oh my goodness. You’re so thoughtful. You hit most of the bullet points.
Alice Tang: One of the things that, audience are always curious because this is, Women’s Million Dollar Conversation, what you have done and how’d you arrive to your million. And how long does it take to do that?
Caroline Carr: Yeah. The first million is really through just consistently investing in my career, to be honest. Both my husband and I, we graduated, from U of O with our accounting degrees, and we were very fortunate because when we first graduated, that was at the time when the accounting industry was really blooming. There was lots of opportunities. Yeah, we both were able to join a really good firm and kinda started building that foundation.
We both made good money, I would say, coming out of college and just… We worked a ton, public accounting back in the day. Now, I think it’s very different. Back in the day, we were putting in 60, 70 hours. That was normal, especially during busy season.
At Nike, I was in the office till, 1:00 AM sometimes for the quarterly earnings. Breakfast, lunch, dinner was at the office, and so we put in a lot but to kinda go back to your question, it wasn’t overnight.
We were making good money, and we save a lot of the money and also investing over time. And that compounding effect, Alice, as you know, it’s huge. But yeah, I would say it’s consistency, hard work, investing.
And I also over time learned that growing up, as immigrant family from Hong Kong, my parents really didn’t have the opportunity that I have today. They both worked manual labor jobs. Very hardworking people. Their mentality was saving every single bit that they have.
That’s the mentality that I grew up with, and now I’m older, I’m learning more and I, my mentality seem to kinda go from the scarcity to abundance, which is like growing, focusing on growing the top line. Like you can achieve… You can build wealth and foundations through many different ways. saving is one way, but also growing your top line is another way.
And really being, thoughtful and intentional about, the choices that we make, I think also kinda help us reach that, that first million-dollar mark.
Alice Tang: Sure. We are very appreciative of,how you share, it’s really through multiple things. It’s not one line. To save, but investing is important. Looking at the top line is important.
The curiosity, from the audience is, approximately how long does it take for you to get to that level, in terms of years?
Caroline Carr: Yeah. It took us about 15 years, to be honest, Alice, if I look back and think through. Ty and I make decent income as CPAs, early on, and so we were able to save quite a bit of the money, and always reinvesting. Both him and I, have a love for real estate.
And so early on in our career, any time we have extra money we we would actually go out and look at houses and see, and see how we can add value. Buying properties and adding value, and then turning it into more of a long-term investment.
We did not know a lot about the stock market. We didn’t have time to, study a lot. A big part of our investment thesis has been real estate, and that has really helped us because it’s a long-term view. It’s not short-term. A big part of our portfolio is residential real estate investments. And so that has helped us a lot.
Alice Tang: That’s good. I have to tell the audience that I had the pleasure, actually, walking into one of your property because that was a little farm slash, a rental. So there is a farm behind that. There are all kind of vegetables and plants. And lately I saw videos from Ty, in Instagram sharing how he saved a plant and all these wonderful things where Alice, I kill everything. So cut this finger.
Caroline Carr: I’m like you; I’m more of the consumer rather than the, the creator in that sense. Yeah
Alice Tang: Yes. That makes very good partners between the two of you.
Alice Tang: Now, when you grow up, every one of us has a money story or money narrative, whether it, excited about it or scared about it, fearful about it, or I hate it. So what was your story about money?
Caroline Carr: Yeah, I, honestly, Alice, growing up, money was hard. We didn’t have money. My mom and dad both grew up very poor, especially on my dad’s side. They never went through any formal education. My dad actually never even went to, school, he learned reading and writing on his own.
He was born and raised in rural China, and when he was a teenager, he, actually, swam across the river and escaped to Hong Kong. Similar with my mom. My mom’s family also didn’t have a lot of money.
It was mostly a scarcity mindset, and money was very hard to come by. My mom was very good at saving money. And it was to an extreme where… I’ll give you this story. Just the kitchen faucet, right? And if the water is, dripping, my mom would put a bucket to catch the little drips of water, so that she can repurpose the water later for cooking or, for shower. That’s the extent of her savings mindset.
I think my parents have always vision; education was a big, important piece because they really believed that, they didn’t get a chance to have education, so they wanted to make sure my brother and I have the opportunity to receive good education, and that will kind of set us on the right path of, having a stable income.
So growing up, money was about security. It was about stability. It was not really about being wealthy or becoming, multimillionaire or anything like that. Mom and Dad was like, “When you grow up, you need to go to college. You need to have a job, provide for your family,” and that’s kinda how we have stable life.
I really appreciated that, those fundamental principles because it really taught me a lot. just built the right foundation for me to be able to be financial responsible, to have the discipline of not, not chasing, shiny objects all the time and just be practical, right?
Now I view it, more like as a tool, and so yeah, this past couple of weeks have been really tough because my mom actually has been sick, and she actually got admitted to the hospital. Yeah, it’s been really hard. But I am able to spend a lot of time with her every day at the hospital, which I’m very thankful for, and that’s kinda the life that I wanna create, is I wanna be able to have the freedom to, to do things like this, to care for the ones that I love, to, to invest in the people that I believe, to build opportunities for others, and also give back to the community as well.
Alice Tang: That gave me goosebumps a few times. the first time was, when you talk about your mom, the bucket from a faucet. Although my mom hasn’t done that she saved the envelopes. And then she would clip the stack of envelopes. That is what she used to write memo, she write from the bottom for a list. She write from the bottom, so you always can tear off and leave the top at the clip. So until both sides are fully used, she wouldn’t throw it away. So her generation, probably my mom is, 20 years older than your mom, but they came from a scarcity moment where there was nothing, and they just need to save every single bit of it, and still today, she’s turning 90. Yes, she’s still doing that. she has no idea that she got the funds. So is another conversation about the accumulation. Make sure you’re happy. So today we want to focus on, on you,a while ago you mentioned that you redefined success.
Alice Tang: So tell us a little bit about what the definition of success is today.
Caroline Carr: I honestly, Alice, I think like I mentioned before, like success before was about title, my climbing the corporate ladder, today’s success is building something that’s meaningful for me and my family. And so it’s giving myself the permission to do that. When I tell people I’m now selling ice cream, some people may think, “Oh my gosh, why would she do that? Why would she leave her professional career and do this? Feels like a step back.” I don’t see it that way. I’m using All the skills that I’ve learned, the finance background, what I know about startup, what I know about solving business problem, what I know about, finding that, product-market fit and really discovering, ‘How do I deliver the most value to people?’ I’m utilizing all that skill to build what I’m building today.
But it took me, 20-plus years to be able to have the courage to do this. I don’t know anything about food. I didn’t know how to make cookies. I have to learn how to make all that from scratch. It took six months to really test out with all this recipe with my good friend Tiffany back then helping me out and, I didn’t even know butter needs to be room temperature for baking. So it was like once I decided that I wanted to try this thing, I went all in. I started this business about, a year and a half ago, but I really have been preparing it for two years. I really spend a lot of time on the product and figuring out,
I’m not pouring all of our savings into this. I’m being thoughtful. We test out the market first, see even if I like this lifestyle, I don’t know anything about the food industry. Will people take me seriously? Every single step is, just giving the permission to try and learn. And I have to say, I have learned so much this past year in just, doing pop-up events, doing private events, and really learning all about social media.
And so success to me is really giving myself the permission to, utilize my skill in a different way and continue to reinvent myself and, and deliver values to others,
Alice Tang: That’s a very beautiful way to weave, everything you love to do into life. What I’ve learned from our short conversation is that, every skill, every training we have, can be used in the future, so there is no waste learning time. The fact that we are changing the title of who I am, CFO to entrepreneur is not like we drop everything we have learned, we carry forward, to facilitate the new journey, the new chapter.
Alice Tang: So we have a question here. why is there an, the name that has a bike there? Does Maddie loves riding the bike?
Caroline Carr: she loves the products for sure, the ice cream and the sorbets. actually, you know what? The idea of the Cream Bike is not actually my original idea.
I do have a, big love, I’m a big fan of ice cream, my initial idea was actually doing a, like an elevated soft serve concept. But after doing a lot of research, I was like, “Maybe I’m not ready for this,” because it takes a lot of investment. because the machines are very expensive, and I wanted to do it in a,like either in a food truck, or in a cart. but I came across, a YouTuber named, Codie Sanchez.
I watch a lot of her content, and in one of her episode, she has this lady named Catherine O’Brien on, and she’s actually one of my mentors now. she started this cream bike business in Maryland over 10 years ago and had a lot of success with it. her story really resonate with me [00:17:00] because she also started as a,office job.
And she was doing this on the side and seeing can I get some traction? And she was very successful with it. And so now she actually has a university teaching people how to run the bike business. Basically, the whole concept is that, yeah, rather than investing a lot of money upfront in, in having brick and mortar,the bike business is really a more accessible way to starting testing our concept and really seeing whether if you can get traction before you kinda go all in.
When I first saw her idea, I was like, this is very interesting. I wonder if it would work in the Portland market.” And, I also was very skeptical at first, with my finance background. It’s but then I was like, it’s not a huge investment. Maybe I can try it and see how it works.” So, I just lean in. I sign up for her university. I’m taking a slightly different path than what she’s teaching in the program, because the Portland market is very different, the Portland market wants handcraft. They want specialty. We’re a foodie town. People want something unique. People want to see the creativity and something premium, right? We don’t wanna use any preservatives, like weird stuff in our product. The business is still very young, and I’m learning every day, getting feedback from my clients.
The product today is very different than the product that I made two years ago when I first started. Because we’ve gotten a lot of feedback, from people how the cookie feels. The cookie has to work with the ice cream. it’s not a traditional cookie in a sense, and so that took a while to fine-tune, and then also the sizing of the product. And then also, I’m learning over and over again is I’m not really selling ice cream.
I’m selling a moment of joy, a moment of an experience, a moment of connection. When people are at events, It’s a time and place to connect with others and just this Maddie’s Cream Bike, the bike itself, the presentation, the product is a vehicle for them to enjoy a moment together.
I just have so much satisfaction when I see people, their smiley face when they see the bike and they, when they enjoy the product. My clients are not the end consumer. My clients are the event planners, the host, right? They’re already very busy. Event planners are one of the most stressful jobs on earth. because everything is, coming down to that day or that event, and there are so many moving parts.
There’s AV, there is set up, there’s catering, there’s thousand pieces moving. And so my goal in creating this service is really building something very easy for them. We will just show up. We don’t need power, we don’t need kitchen, we bring in our team, we serve the ice cream. Nobody needs to worry about it. And just building the service around, making their life easy.
So it’s just a completely different appreciation of the whole ecosystem that I didn’t know existed. I’m having fun with it, and I feel like this could, really build a good role model for my daughter, Maddie, as well. And kind of giving her an opportunity to be involved when she’s older, if she wants to. She may not want to. I can start teaching her, basic concepts and and then also having her being around people and my team is incorporating that life into the business and business into the life and building something that works for our family,
Alice Tang: I hear the legacy is really being a role model of your daughter so she knows what she can do, and hopefully it expands her beyond the two of you because who knows what she’s gonna come up to.
Caroline Carr: Yeah, who knows?
Alice Tang: Grow up as she, as you see her, get her taller and taller. I’d better see her earlier because my height, as she’ll be surpassing me
Caroline Carr: Oh, she would surpass me for sure.
Alice Tang: Good. Today is such a wonderful conversation with you, Caroline. Thank you for sharing, not only specifically your current journey, but the whys and the foundation of who you are.
We’re so grateful for you, Caroline
Caroline Carr: Yeah, no, thank you for having me. I’m just so grateful too for this opportunity to share my journey. I’ve been very lucky to have really many great mentors in my career. It’s important that we all share our journey and we can all learn from each other.
Alice Tang: If the audience want to find you, what do they do? How do they get to you?
Caroline Carr: Yeah. You can check out my website at, www.maddiescreambike.com, or you can reach out to me just directly, via email caroline@maddiescreambike.com. Whether you wanna just chat, want to learn about my journey, or if you want to actually taste our product. Yeah, I’m always happy to share
Alice Tang: Beautiful. Thank you so much once again, Caroline.
Caroline Carr is the founder of Maddy’s Cream Bike, a Portland-based premium event hospitality company specializing in handcrafted ice cream sandwiches and joyful guest experiences. Prior to entrepreneurship, Caroline spent over 20 years in accounting, finance, and startup leadership. After becoming a mother, she reimagined what success could look like and began building a business centered around family, community, and meaningful human connection. Today, she partners with corporations, healthcare organizations, nonprofits, and event venues to create memorable experiences throughout Portland. Caroline is passionate about helping women understand that it’s never too late to reinvent themselves and build a life aligned with their values.