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Took 20 years to become an overnight success

Took 20 years to become an overnight success

| March 07, 2026

20 years ago this month I had a crazy idea to start my own financial practice. My wife and I along with our 12-year-old son were at the Top Advisor conference in the Bahamas. We were being wined and dined that evening at Nobu. As dessert was being brought out, I noticed a waiter coming out with a platter of grilled cut steak. Clearly something had gone wrong in the kitchen as dessert and steak don't usually go together.

My son, upon seeing the steak, leaned over and said, "Dad, I can't do this any more". While he was referring his stomach getting ready to burst, I in turn pondered what I was doing at Top Advisor. I was the Sales Manager and OSJ for the #1 US office of this broker-dealer. But was I living my values? Was I being true to myself? Could I make more of an impact on my own?

I turned to my wife and told her I was going to strike out on my own with a practice focused on 401k plans as that is where my background was. She thought about it and then said, "I'll quit my job as well and join you". We both jumped into the proverbial deep-end of the pool and just as we got our feet under us, the 2008 recession hit.

We learned quickly that companies just trying to survive are not inclined to discuss their 401k. And yet, in spite of all that was thrown at us, we are still standing 20 years later. 100 retirement plans under advisement across the US. We must be doing something right.

I was thinking about our twenty years (36 years for me in the industry as a whole). In the retirement plan industry, there is a persistent temptation to believe there are shortcuts. A new product. A regulatory workaround. A marketing angle. A faster way to scale. After twenty years, I can say with conviction: there are none.

Sustainable success is built the slow way. This is true in the financial services industry and even baseball. Baseball, you say? Yes, I was reading about the Savannah Bananas so bear with me.

Today the Savannah Bananas sell out major league stadiums and command national attention. But its founder, Jesse Cole and his wife once had $1.8 million in debt as they tried to launch this new baseball team. They slept on an air mattress in a studio with $30/ week for groceries. There was no viral breakthrough at the beginning—only years of persistence, operational refinement, and an unwavering commitment to delivering an experience people loved.

And while the Bananas' games are entertaining, the lesson is not about entertainment. It is about endurance.

Cole did not game the system. He did not look for short cuts. He focused on fundamentals: know your audience, deliver consistent value, reinvest in improvement, and outwork the competition. The “overnight success” was a decade in the making.

Contrast that with the cautionary example of former Morgan Stanley advisor Darryl Cohen. Attempting to shortcut the system—circumventing compliance protocols and engaging in misconduct—ultimately led to termination and reputational damage. In financial services, there is no durability in cutting corners. Regulators have long memories. Markets are unforgiving. Trust, once compromised, rarely returns.

For 401(k) plan sponsors, the parallel is direct. There are no shortcuts to:

  • Improving participant outcomes.

  • Elevating fiduciary governance.

  • Driving higher participation and deferral rates.

  • Building a defensible investment lineup.

  • Maintaining operational compliance.

Automatic features, thoughtful QDIA selection, fee benchmarking, documented process, and consistent employee education are not flashy. They are disciplined. And discipline compounds.

Trying to “optimize” around fiduciary responsibility—whether by ignoring documentation, chasing performance, or minimizing oversight—creates hidden liabilities. It may feel efficient in the short term. It is expensive in the long term.

At Green Retirement, we have seen quite a few disruptions. Markets have cycled. Regulations have shifted. Political administrations have changed. Fads have come and gone. We are still standing.

Not because we discovered a shortcut.

Because we did not look for one.

We believe retirement plan excellence is operationally methodical: structured investment governance, repeatable fiduciary process, measured plan design improvements, and incremental participant engagement. It is not glamorous work. It is compounding work.

The Savannah Bananas did not build their brand overnight. Owner Jesse Cole endured years of uncertainty before breakthrough. And in our industry, advisors who try to bypass process eventually encounter consequences.

In retirement plans—as in baseball—the fundamentals win.

The Parting Glass

If there is one principle I would urge plan sponsors to internalize, it is this: sustainable outcomes require patient, disciplined execution. There is no substitute for doing the work.

And that is precisely why we are still here.