Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Harold "Trey" Fairman III, Founder of Waypoint Retirement Advisors LLC., located in Fayetteville, AR and San Diego, CA, USA.

What's your business, and who are your customers?

My primary businesses are as a retirement plan advisor (think workplace retirement plans like 401k and 403b plans) and consulting expert in financial litigation matters. As a retirement plan advisor, my customers are business owners, accountants, and individuals in charge of their company’s retirement plan. As a consulting expert, my customers are attorneys.

Tell us about yourself

The story of my company all started with an eye-opening experience in the spring of 2016. In the early afternoon of Tuesday, May 3rd, I had just finished my presentation at the 2016 Physicians Financial Summit sponsored by the American Medical Association in Orlando, Florida. In the two decades leading up to my presentation, I had obtained my law degree, passed the California bar exam, earned an additional master’s degree in tax law, and sold my business to a publicly-traded financial services company. My specialty was partnering with business owners, accountants, attorneys, trustees, and advisors at many of America’s largest investment firms, trust companies, and private banks. I had also married a great woman, raised two boys, adopted a couple of dogs, and started a side hustle as a consulting expert to law firms regarding financial litigation matters.

As I sat down in the hotel lobby to enjoy some coffee after my presentation, multiple physicians approached me to discuss their retirement plans. They were all earning over $1,000,000 per year, and they all had the same run-of-the-mill “safe harbor” 401k plan. “Safe harbor” plans reduce complexity for advisors but limit contributions for participants. In 2016, the “safe harbor” plan contribution limit was $53,000 per year - $59,000 if they were age 50 or older. Either way, it was far below the amount they should have been saving on an annual basis.

As my conversations continued, I learned they each wanted to put aside more money but had been told they could do nothing more. Their expressions changed when I explained they received bad advice and the maximum contribution that year was closer to $235,000 - not $59,000 as stated by their advisors. I was curious. Why the disconnect? What was I missing? These physicians had professional advisors, but the advisors appeared to be in the dark regarding retirement plan design. The high-deductible plans I mentioned weren’t a secret-they were IRS approved and had been around for some time.

When I returned to my office, I researched and studied all that I could. I reached out to my contacts in the retirement plan industry for feedback. I learned that advisors rarely offer anything beyond a basic solution, and most advisors are in the dark when it comes to retirement plan design. My follow-up research confirmed generic “cookie-cutter” solutions were the norm.

Since then, I’ve learned that my accumulated experiences in the tax, legal and financial worlds give me a broader and deeper perspective than many, providing valuable insights and observations. You see, over the past few decades, the retirement plan industry has evolved from a casual investment conversation to a much more regulated and formalized fiduciary oversight process. This oversight process is not rocket science, but it does require some organization, documentation, and adherence to a few “prudent” principles. And once you have a good plan, it must continue to evolve to remain compliant and enhance employee benefits.

I founded Waypoint Retirement Advisors to improve the quality of retirement plan advice by offering employers and employees the support they need to make well-informed, intentional decisions about their retirement plans and their futures.

What's your biggest accomplishment as a business owner?

I’m still standing. I am grateful to all the individuals and institutions that have allowed me to partner with them in providing meaningful solutions to improve their financial situation. I have been honored to serve and humbled by the trust and confidence they have placed in me over my almost thirty-year career.

What's one of the hardest things that comes with being a business owner?

To remain standing. For me, it has been improving, evolving, and adapting at the proper times, all while staying true to my core strengths and beliefs. The consolidation of the investment, banking, and insurance markets has dramatically impacted what I do and how I do it. Tim Ferris has a great piece on the entrepreneurial roller coaster that I refer to often.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Do what you know.
  2. Think outside the box.
  3. Remain flexible.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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