Navigating your Hawaiian Dream.
Meet Douglas
Guiding You Toward Peace, Purpose, and Possibility in Paradise
Douglas Hunter brings a rare combination of strategic insight, heartfelt connection, and wide-ranging expertise to help you navigate the next chapter of your life with confidence — whether you’re planning your Hawaiian retirement, making a smart real estate move, optimizing your health coverage, or exploring how AI can support your work and creativity.
As the founder of Legacy Maven AI, Douglas helps seasoned professionals, entrepreneurs, and creatives harness artificial intelligence — not as a gimmick, but as a practical, human-centered tool to reduce burnout, automate busywork, and amplify what makes them unique. His approach is strategic, thoughtful, and rooted in the belief that AI should work for you — not the other way around.
With deep roots in finance and real estate, Douglas has successfully guided clients through more than 50 transactions totaling over $60 million in property sales. He holds licenses in Real Estate, Health, Life, Property, Casualty and Disability, allowing him to offer truly holistic guidance across your financial, insurance, and retirement landscape.
Douglas earned his MBA from The Anderson School at UCLA and holds a BA in Japanese and Business from the University of Michigan. His academic foundation supports his client-first ethos: listen deeply, act wisely, and deliver with integrity.
Beyond his credentials, Douglas is a true citizen of Hawaii. He’s a member of the Kailua Canoe Club, a licensed SCUBA diver, a budding surfer, and someone who lives the aloha spirit in and out of the water. Whether he’s gliding across the waves or helping you plan your next move, his passion is helping people find clarity and joy.
Reinvention. Reintegration of creativity. Whatever stage you’re in, Douglas offers more than advice — he offers partnership. Let him help you shape a future that’s rich in peace, possibility, and purpose.
Holistic Services
Legacy Maven AI
Clarity Through Innovation
Artificial intelligence isn’t just the future — it’s the present. But for many seasoned professionals in Hawaii, AI still feels confusing, impersonal, or out of reach. That’s where Legacy Maven AI comes in. Douglas brings decades of experience in business, entertainment, real estate, and financial planning — and combines it with a human-first approach to AI strategy. Whether you’re a small business owner, consultant, or creative entrepreneur, Legacy Maven AI helps you cut through the noise, uncover where AI can make a real difference, and build systems that support how you work best.Through a personalized Deep Dive and a custom AI roadmap, Douglas helps you delegate the busywork, reclaim your time, and amplify your creativity. No tech jargon. No hype. Just thoughtful strategy that lets you focus on what you do best — with AI as your thought partner, not your replacement.
Medicare Guidance
Your Health, Our Priority
Navigating the intricacies of Medicare, especially in the vibrant context of Hawaii, can seem daunting. With Douglas by your side, consider the maze unraveled. Our in-depth consultations are crafted to understand your specific health and financial landscape. This personalized approach ensures that you're not just getting a Medicare plan, but the right Medicare plan. From understanding the nuances of local healthcare providers to ensuring seamless transitions if you're relocating from another state, trust in a service that prioritizes your well-being just as much as you do.It all begins with an idea. Maybe you want to launch a business. Maybe you want to turn a hobby into something more.
Real Estate Services
Your Dream Home Awaits
Hawaii offers more than just picturesque landscapes; it promises a way of life that's tranquil, fulfilling, and deeply connected to nature. With almost a decade of real estate experience, Douglas has an innate understanding of the island's property landscape. Whether you're looking to downsize to a cozy beachfront condo or find a home nestled in the serene valleys, Douglas's expertise ensures your next home aligns with your retirement dreams. Benefit from tailored property tours, insightful advice on transitioning to more manageable properties, and the assurance of making a choice that fits both your desires and needs.
Retirement Planning
Turning Visions into Reality
Retirement is more than just an age or a date on a calendar—it's a new chapter, ripe with possibilities. With Douglas's comprehensive retirement planning services, you're not just preparing for the future; you're sculpting it. Through expert financial guidance, learn how to make your funds work for you, ensuring a steady income stream that lets you enjoy every moment of your Hawaiian retirement. From understanding market dynamics to crafting investment strategies aligned with your goals, step into a future where financial security meets island serenity.