Caitlynn Eldridge: From CPA to Co-Founder of Prospera Strategy

Please share a brief introduction about yourself and your business

I'm a mom of five (all 10 and under), a military spouse, a CPA, and the co-owner of Prospera Strategy LLC. I’ve been a CPA for nearly 15 years, with experience at Deloitte, Union Pacific, and in family office environments before launching my own firm.

In January 2025, I partnered with a like-minded business owner (Seanna) to create something bigger — and better. Together, we combined our strengths to build Prospera Strategy into a true one-stop shop for bookkeeping, tax, payroll, and advisory services.

At Prospera, our focus is on simplifying the financial side of business so our clients can spend more time growing and less time worrying. We're passionate about helping businesses thrive — and we'd love to be part of your journey.

Who are your customers?

We serve small business owners (across all industries) who are passionate about growing their businesses and deepening their financial understanding. We love working with clients who value collaboration and see us as trusted partners on their journey — not just another task to check off.

What was your background prior to starting your own business?

Before launching my own firm, I built my career in public accounting at Deloitte, working primarily with high-net-worth families on their tax needs. I loved the variety and complexity of the work, but I struggled with the work-life balance and knew it would be years before I'd have real, direct relationships with clients — something I truly valued.

From there, I transitioned to a family office, where I handled accounting and tax reporting for a local family. It was a great opportunity, but I still felt something was missing. I moved next to Union Pacific’s tax department, and it was truly one of the highlights of my career. I had incredible mentors, learned so much, and really grew professionally.

Even so, when I looked ahead, I couldn’t quite see myself staying on the corporate path — moving into a director or VP role didn’t feel like the impact I was searching for. I realized I wanted to work more closely with people, to make a direct difference in their businesses and lives. That realization eventually led me to entrepreneurship — and to work that feels truly meaningful.

What made you take the leap to start your own business?

Honestly, it started out of necessity. My husband was active duty military, and we had just welcomed twins — our second and third children — into the family. As much as I loved my career in the corporate world, I knew deep down it wasn’t going to fit the kind of parent I wanted to be or the life we were building.

After giving my notice, a friend asked if I could help out with a few clients. I said yes, thinking it would be temporary. But as I worked with them, something clicked. I realized I could build something that served others while also creating the flexibility my family needed. That small step turned into a bigger dream — and eventually into a business I'm deeply proud of.

Did you always know you wanted to be an entrepreneur?

Not at all. I grew up in a military family where stability and traditional employment were the norm. To me, the paths had always seemed clear: build a career in the corporate world or stay home to raise a family. The idea of entrepreneurship felt completely foreign — something other people did, but not me.

But life has a way of opening doors you never expected. Stepping into business ownership has been one of the most challenging, rewarding, and amazing experiences of my life. What once felt unfamiliar has now become a calling I'm so grateful to have answered.

Take us back to when you first launched your business; what was your marketing strategy to get the word out and did it go as planned?

When I first launched, I knew I wanted to build a remote business — one that fit the life I was creating for my family. I started small, showing up online, answering questions in groups I was part of, and letting friends and family know I was accepting clients. My focus was simple: serve every client exceptionally well and trust that good work would speak for itself.

As I gained traction, I joined a few masterminds where I could continue sharing my expertise and building relationships. Slowly but surely, a client base began to grow. Referrals quickly became my primary marketing engine, along with a steady presence on social media.

Looking back, it was exactly what I needed for that season — manageable, sustainable growth while I built strong foundations. Now, with those roots firmly in place, it’s time to scale and reach even more people.

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

One of the biggest challenges was navigating entrepreneurship while growing my family. I had two children during this journey — and there were moments where balance felt almost impossible. I even found myself working from a hospital bed while in labor. It’s not something I ever wanted to glorify, but at the time, it was survival.

Those experiences taught me a lot. Looking back, I can see that I leaned into work more than I intended — and while that was part of the season I was in, it also shaped a bigger vision. It showed me how important it is to build a company that truly supports families, one where taking care of life outside of work is not just allowed but encouraged. Balance might always be a moving target, but we’re creating an environment where our team doesn’t have to choose between career and family — and that’s something I’m deeply proud of.

What accomplishment are the most proud of to date in your business?

I'm proud that, through all the growth and challenges, I've stayed anchored to why I started this business in the first place. I built a career that supports my family — not one that competes with them.

Even when it meant saying no to faster revenue or bigger opportunities, I chose to protect my time, my values, and the life I set out to create. Seven years later, I’m still standing by those choices — and I know that success isn’t just about numbers. It’s about building something that feels right, honors what matters most, and sets an example I’m proud of.

Do you have any recent wins from the last year that you'd like to celebrate with our community?

A merger! Which is huge because we accomplished it during tax season craziness with our amazing team.

What's next for your business? What can we expect to see over the next few years?

At Prospera, we’re building more than just an accounting firm — we’re creating a movement toward a better way of doing business. One where clients feel truly supported, employees are empowered and respected, and growth never comes at the cost of balance or well-being.

Over the next few years, you’ll see us expand our impact: launching educational programs, a podcast, and a "do-it-with-you" service designed to equip business owners with the tools and confidence they need to thrive. We’re not just here to meet expectations — we’re here to reshape what people expect from their accountants, advisors, and partners. The future is bright, and we’re just getting started.

What is your top productivity tip? 

Post-it note to do's and a walking pad. Both have helped me attack a lot of work in a short period of time. Long to do lists can be overwhelming so prioritizing just a few things every day is key. For tasks I struggle to begin- it helps if I'm moving so I'll get on the walking pad and suddenly that work seems a lot easier.

On the flip side, how do you avoid burnout?

Avoiding burnout is such a personal journey. For me, it comes down to protecting my time and energy with clear boundaries — setting strict work hours, communicating with clients that they can expect a response within 48 hours, and making sure there’s plenty of space for joy outside of work.

Another key piece has been redefining success for myself. I’m not chasing the traditional idea of "more, bigger, faster." Instead, I check in with myself often, making sure I'm finding fulfillment in many areas of life, not just in business. That perspective has been a game-changer — and it's helped me build a career that feels both sustainable and deeply meaningful.

What is your approach to work-life balance / integration?

For me, balance feels less like a perfect split and more like a pendulum — constantly moving, with the goal of avoiding the extremes. Some days naturally lean more toward work, while others lean more toward life, and that's okay.

We’re intentionally building a business model that supports this rhythm for both our team and ourselves — with consistent monthly revenue and seasonal tax work creating flexibility instead of chaos. It all comes down to being clear on what matters most: identifying the key moments in both life and work that I need to show up for and making sure I honor those.

I've also spent a lot of time getting to know myself — understanding how I work best, what lights me up, and how to design my days and my role around that. Balance isn’t about perfection; it’s about creating a life and business that support each other, not compete against each other.

What is one thing you wish you had known when you started your Entreprenista journey?

I wish I had trusted my own expertise from day one. I spent too much time early on second-guessing myself — getting distracted by flashy success stories that promised six figures with 10-hour workweeks.

The truth is, I knew better. My background in numbers told me those stories didn’t add up, but I didn’t trust my instincts the way I should have. I invested in things that, knowing what I know now, I would walk away from without a second thought. The lesson? You already have everything you need to build something incredible. Trust yourself, trust your experience, and don’t let the noise shake your confidence.

When hiring, what is your go-to interview question?

I don't have just one! I like to ask about a candidate’s Myers-Briggs type, Enneagram, and Human Design. I’m really interested in getting a sense of who the person is beyond just their resume. So far, I’ve been lucky with hiring, but I’m also excited to keep learning and refining my approach as we grow. Building the right team is such an important piece of what we’re creating.

Are you a Mamaprenista? If so, please share your best advice for simultaneously managing a business and a family

I am — and it’s a wonderful, wild ride with five little ones (10, 7, 7, 4, and 2)! My best advice is to get really clear on your goals for both your business and your family — and to build your schedule around your definition of success, not anyone else's.

For me, that looks like working three mornings a week with the help of a part-time sitter, instead of full-time daycare. It means my business grows a little slower than it might if I worked 40+ hours a week — but it also means I’m there for the moments with my kids that matter most.

The truth is, there’s no secret formula (even though we wish there was). I've learned to treat life and business in seasons: some seasons are for growing the business while my husband carries more at home, and some are for slowing down to be more present with family. I’m careful not to overcommit and I make space to recharge, so I can show up as my best self wherever I’m needed most.

Do you have a co-founder? If so, how did you find the right one for you and what are your best partnership tips?

Yes! I truly believe it was fate — or God — depending on how you see it. My business partner and I had known each other for years, each building our own paths separately, but always cheering each other on from afar. Over time, we both casually mentioned how incredible it would be to someday join forces. When the timing was right, everything aligned naturally.

Our shared value systems, business philosophies, and vision for growth made the decision easy. One thing that’s really helped is that we didn’t start out as best friends — we started with a professional respect for one another, which laid the foundation for a strong, healthy business relationship that’s only deepened over time.

A few things I've learned about great partnerships:

Alignment matters more than anything. Skills can be taught or adjusted — but core values and long-term vision need to match from the start. Communicate early and often. Don’t wait for issues to pile up. Regular check-ins, even when things are good, keep everything strong.

Define roles clearly. Knowing who owns what reduces confusion and keeps momentum going. With this- very clear legal documents that protect both parties and provide an out for anyone who might want to exercise it. 

Leave room for growth. Relationships evolve, businesses evolve — and giving each other grace and space to grow together is key. Finding the right partner isn't just about skills or personality — it’s about building a shared foundation for something bigger than either of you could do alone.

What's the one app on your phone you absolutely cannot live without and why?

Kindle or audible- I love being able to pull up a book no matter where I am and what mood I am in.

What is your favorite business tool or solution and why?

Since we run a team I'm quickly finding I really love Missive for email- it's been easy to tackle a lot of client communication with this. We truly value being responsive and this has helped.

What advice do you have for aspiring Entreprenistas?

Be great at problem solving- that's what this life is. There's constantly a problem to solve and with a great set of values and beliefs to guide you- it'll be an exciting and wonderful experience. Also know your numbers! I know that sounds silly but I know I've made it farther by really being in tune with all financial aspects of my business. When you know what you need to survive you have the option to stand firm with your values.

Learn more about the Entreprenista League and join today

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