...and by the time I was 15, I had built a pretty sizable lawn business. Even then, I loved the idea of creating something of my own and serving people well.

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While attending the University of Georgia, I was hired during my senior year to help build and manage Sizzlin’ Steakhouse locations throughout Georgia and Florida. It was an intense and fast-paced role where I handled everything from construction punch lists to hiring, training, opening new restaurants, and then moving on to the next location.

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Those years taught me how to lead teams, solve problems under pressure, and work hard—really hard. After years of seventy- to ninety-hour work weeks, I decided it was time for a different direction.

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I returned to the University of Georgia to pursue graduate studies in behavior modification and later worked with the Walton County School Board helping underprivileged children who had already fallen through the cracks of the educational system. That experience reinforced something I still believe today: people deserve patience, understanding, and someone willing to meet them where they are.

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Entrepreneurship kept calling me, and I eventually opened my own landscaping and nursery company in Loganville, Georgia, just outside Atlanta. What started small grew into a successful business serving residential clients and major commercial accounts, including organizations connected to the Atlanta Falcons and several large Atlanta-area banks.

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Hospitality, Technology & Executive Management

In 1983, an opportunity brought me to Orlando to help operate the Days Inn Disney West Hotel. Those years in hospitality were exciting, demanding, and incredibly rewarding. We modernized operations, upgraded technology systems, and worked tirelessly to improve the guest experience. By 1984, we were named Restaurant of the Year, and in 1985, Franchise of the Year.

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One of the hotel’s financial partners later invited me to Athens, Georgia, to help manage a corporation that included multiple dealerships and businesses. After a leadership transition within the company, I was asked to become Executive General Manager and Vice President of the corporation.

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Eventually, my brother and I partnered together to purchase and operate a Best Western hotel near Disney World in Orlando. For eight years, we successfully managed a very busy property that maintained approximately 87% occupancy during our ownership and management period.

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Those years taught me how to manage people, navigate challenges, build systems, and lead organizations through growth and change.

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Helping People Retire with Confidence

By the mid-1990s, after years in hospitality and business management, I knew I wanted to transition into a profession where I could help people more directly with their future and financial security.

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In 1995, I joined Equitable in Orlando and began my career in financial services and retirement planning. After several years with Equitable and later with National Life Group, I founded Dillard & Associates in 2003.

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Over time, my work expanded beyond financial services into business consulting for organizations ranging from small local businesses to large corporations and government-related entities throughout Central Florida and beyond.

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Today, my focus is where I believe it matters most: helping people prepare for retirement with clarity, confidence, and practical guidance.

I understand that retirement isn’t just about investments or financial products. It’s about peace of mind. It’s about knowing you can pay your bills, enjoy your life, handle healthcare decisions wisely, and avoid becoming a burden on the people you love.

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I also understand that many people feel overlooked by traditional financial firms because they don’t have massive portfolios or hundreds of thousands of dollars to invest.

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That’s exactly why I built ChatWithRandy.com.

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I believe everyone deserves honest guidance, thoughtful planning, and someone willing to sit down and help them make sense of retirement, Medicare, income planning, and long-term care options—without pressure or intimidation.

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As a fiduciary, my commitment is simple:

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Put people first.
Listen carefully.
Explain things clearly.
And help clients retire with dignity and confidence.