Success is a funny thing. From the outside, it looks like the ultimate goal—building a company, making money, and achieving big milestones. But as I sat down with Ricky Caplin, it became clear that success was just the beginning of his story. His journey is about so much more than business; it's about faith, purpose, and making a real impact. Ricky is one of our favorite investment partners here at MHP. He has a vision that makes everything else seem small. Here are four big takeaways from our conversation.
1. From the Top of the Business World to a Spiritual Awakening
Ricky did everything "right." He got his degree in accounting from the University of Florida, climbed the corporate ladder at a Big Four firm, and then built The HCI Group into a global powerhouse in healthcare technology consulting. When they sold the company, he had every reason to feel accomplished. But something was missing.
He told me about the moment he realized that, despite all his success, he was spiritually bankrupt. His priorities had been out of order—putting himself first, then family, then community, and fitting God in when convenient. That moment of conviction changed everything. He started reading the Bible daily, and over time, it reshaped his entire perspective on life and business.
2. Faith as the Foundation for Business
Ricky’s faith didn’t lead him away from business—it gave him a whole new reason to do it. After selling his company, he didn’t just sit back and enjoy financial security. Instead, he launched Kaplan Ventures, a first-generation family office with a clear mission: to amplify faith, hope, and love in business and communities.
One of the things he kept coming back to was the parable of the talents. Instead of just managing wealth, he saw everything he had—his skills, his network, his resources—as a stewardship opportunity. The question wasn’t, "How much can I make?" but "How can I use what I’ve been given to make a lasting impact?" We cover the value of mentors like Tim Dunn and how a Donor Advised Fund works.
3. Meaningful Partnerships and Unexpected Doors Opening
One of my favorite parts of Ricky’s journey is how he approaches relationships. Instead of forcing things to happen, he focuses on walking by faith and letting doors open naturally. That’s how his partnership with Tim Tebow came to be.
Originally, someone suggested he reach out to Tebow, but Ricky decided to pray on it instead of pushing for a meeting. Months later, completely out of the blue, the opportunity came to travel together, and from there, a genuine friendship and working relationship formed. Now, they collaborate on anti-human trafficking initiatives, impact investing, and more. It’s a powerful example of how faith-led decisions can lead to opportunities you never expected..
Today, their partnership continues to grow as they champion faith-based entrepreneurship through the Waterstone Impact Fund—a fund dedicated to accelerating world-class companies that amplify faith, hope, and love. Together, they’re not just investing in businesses; they’re fueling a movement that empowers faith-driven leaders to build ventures that create lasting change.
4. Using Sports as a Platform for Change
One of the biggest projects Ricky is working on now is Sporting JAX, a professional soccer club in Jacksonville. But it’s not just about the game—it’s about building something that strengthens the community.
The club is launching with a USL men’s team and a top-tier women’s team, plus plans for a 15,000-person stadium and a massive youth development program. They’ve even merged with Florida Elite, making it one of the largest youth soccer programs in the country. The goal? To create a pathway from youth soccer all the way to the pros while using sports as a tool for mentorship, leadership, and character development.
These are the types of projects we love at MHP. Sporting JAX is one of our favorite investments from 2024.
Final Thoughts Talking with Ricky, it’s clear that success means something different to him now. It’s not about building wealth for wealth’s sake but about using business, partnerships, and even sports as a way to serve others. More importantly, it’s about living with an eternal perspective—understanding that the impact we make today echoes beyond our time on earth. His story is a powerful reminder that when you let faith lead, you end up walking in your destiny.
With gratitude,
Marley Hughes
CEO
Magnolia Hill Partners
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