Rylan Maddox is a mortgage professional and entrepreneur with more than a decade of experience helping clients navigate the home financing process with confidence. As the founder of HI FIVE Team Loans, Rylan has built his business around a simple philosophy: make the mortgage process easy, transparent, and enjoyable while delivering strategic guidance tailored to each client’s goals.

Known for his deep expertise in VA home loans, Rylan has become a trusted resource for veterans, active-duty service members, first-time buyers, investors, and families looking to refinance or purchase a home. His approach combines industry knowledge with a highly personalized client experience, helping borrowers understand their options clearly and move through the financing process with less stress and more certainty. Through HI FIVE Team Loans, he works with clients across multiple states, providing access to a wide range of loan programs including VA, FHA, conventional, and specialty financing solutions.

Beyond mortgage lending, Rylan is passionate about building long-term relationships and creating a business centered on trust, responsiveness, and real-world problem solving. He believes great lending is not just about rates and approvals, but about helping people make informed financial decisions during some of the most important moments of their lives. His leadership style reflects the same values that define his company culture: professionalism, accessibility, and a commitment to delivering a high-level client experience from start to finish.

When he is not working with clients or growing his business, Rylan enjoys spending time with his family, hiking, soccer, PC gaming, and being near the beach. Splitting time between Hawaii and Florida, he brings both a personal and professional understanding of diverse housing markets and the lifestyles that shape them.

Kama’aina Mortgage Group Inc. | Company NMLS 1276471

VVA4s are the professionals have earned this rank with time in service as well as exceeding minimum performance standards of VVA3. They have served a minimum of six months as a VVA3, met all performance metrics, and continued to submit their accountability tracking on time regularly. They will answer every question perfectly in accordance with the VA Lender Handbook guidelines, VA resources and, not just one lender's overlays. During these 6 months we are testing their hearts and minds. They will be the embodiment of our institutional core values of honor, courage, and commitment. We want to see the best showing up in VVA4; we want to see how they engage you, respond to your direct questions, and respond to questions that could benefit them but they will never take an individual position to gain through solicitation. We aim to achieve the change we want to find for you and protect you as a Veteran and Active Service Member. Changing the hearts and minds of those helping you is the only authentic way to make a difference. No regulation or rules will help because people are still the same in trying to find easy ways around rules. VVA4 are there to serve you because you serve our Country.

At VVA4 the professional will be eligible to serve as a Squad Leader. This challenge is to begin training peer-to-peer leadership in a unique way. These peers are not employees, they are not subordinates, they are unique peers that choose to follow and whose leadership must be earned. The minimum time spent in VVA4 will be approximately 1 year.