Matthew Sieja · 02 May 2025 · 3 minutes

MARKETING

Racing Toward Retirement: Picking the Right Financial Thoroughbreds

Author: Matthew Sieja Matthew Sieja
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On the eve of the first Saturday in May, all eyes turn to Churchill Downs for “The Most Exciting Two Minutes in Sports.” The Kentucky Derby is a celebration of strategy, preparation, and making the right picks — and when it comes to retirement planning, the parallels are clear. Choosing the right retirement saving vehicles is like picking the right horse: you want a strong performer, built to go the distance, and capable of confidently crossing the finish line.

With the retirement landscape evolving faster than ever, financial advisors must guide clients toward savings vehicles that can handle every twist and turn. Here is a look at a few key contenders that, when combined thoughtfully, can create a championship-level retirement plan.


The Thoroughbred: Roth Conversions 

A Roth IRA conversion is the thoroughbred of retirement planning. Just like a Derby champion, it requires careful timing and a strong foundation. With tax rates likely to rise in the future, moving assets from traditional IRAs to Roth IRAs allows clients to pay taxes now, locking in today’s rates and setting the stage for tax-free income later. Financial advisors who help clients execute smart Roth conversion strategies position them to gallop toward a more secure retirement.


The Steady Workhorse: Annuities 

Annuities may not be the flashiest option, but they are the dependable workhorses that can carry clients across the retirement finish line. Fixed indexed annuities, in particular, offer protection from market downturns and the option of lifetime income. In a field full of unpredictable conditions, annuities provide steady footing and peace of mind for clients who want to make sure they win the race of retirement by never running out of money. 


The Closer: Life Insurance Strategies 

Life insurance is often overlooked as a retirement planning tool, but it can be a powerful asset for the right client. In addition to providing a death benefit, properly structured permanent life insurance policies can offer tax-advantaged growth, tax-free income potential, and legacy planning opportunities. Like a horse that closes fast to win the race, life insurance can provide exceptional value for later-year income needs and – of course – powerful benefits at the finish line.


The Finish Line: Building a Winning Combination 

Just as a Derby champion is the result of breeding, training, and strategy, a successful retirement plan relies on blending multiple saving vehicles to create a resilient financial future. No single horse wins every race. It takes a combination of speed, endurance, and smart management to navigate the long track to retirement security and avoid the most pressing risks.

Financial advisors who can guide clients in selecting and balancing the right vehicles will not only help them “place their bets” wisely but also ensure they cross the retirement finish line with a winning approach — and a legacy worth celebrating.


As the call to post rings out this Derby season, it is a good reminder that early preparation and smart picks make all the difference. Help your clients line up their best options now, so they can enjoy the victory lap later.

Ready to help your clients build a retirement plan that is built to win? Connect with Stonewood Financial and access the tools, training, and support you need to lead them to the winner’s circle.

Real Advisors. Real Results.

See how advisors are using Stonewood software to win larger cases and deliver better outcomes for their clients.

An advisor was working with a prospect who was a real "do-it-yourselfer" when it came to Roth conversions. The client was converting assets up their existing tax bracket – and hadn't considered any impact to IRMAA.

With Roth Done Right, the advisor was able to show an alternate pattern that sped up the conversion to 6 years. The new structure offered $30,000 savings in conversion taxes – a 20% reduction on the prospect's conversion tax bill. The report also showed hundreds of thousands of dollars in long-term tax and IRMAA savings from the converted assets – an amount the prospect hadn't been able to quantify on his own.

Outcome

A new client with $1M in new AUM, and a $1M FIA sale to fund the conversion process.

An advisor was working with a prospect who already had assets with Ken Fisher. Fisher's team presented a 5% systematic withdrawal projection, so the advisor needed a stronger way to frame the income conversation.

Using the Annuity Alpha report, the advisor showed how an annuity could deliver over 8% in annual cash flow with lifetime income, plus a long-term care doubler. The contrast was clear enough that the prospect moved forward.

Outcome

$1.5M placed and a $100K in new business revenue.

An advisor was working with a 58-year-old couple with an established, well-funded retirement income plan, leaving an additional $3M IRA to build out a legacy for the kids. The couple's existing advisor had no real additional plan for this money, other than to keep it in their managed account and grow that money as much as possible for the kids.

Using the Legacy Done Right report, the advisor showed the need for tax planning on this $3M IRA. According to the advisor, the simple analysis "opened up the wallet" to the Roth conversion story. The advisor then used the blended Roth/Life feature in the report to show a blend of Roth Conversion assets with some Life Insurance to help maximize the client’s legacy.

Outcome

$3M in motion. The advisor picked up a $1.5M FIA sale that will be converted to Roth. And the advisor also sold a 5-Pay Protection focused IUL policy at $225,000 of premium per year.

An advisor group incorporated the Total Tax Burden report into the strategy presentation for all new prospects. They ran the tax snapshot for every new client as part of their first meeting conversation, quantifying the growing tax burden of IRA money – and illustrating the kinds of tax savings possible when working with their firm.

Starting in January of 2023, this simple analysis was presented to every single prospect who walked in the door. The goal was to differentiate their practice and drive overall revenue growth through various Roth conversion strategies.

Outcome

From 2022 to 2025, new annual AUM rose from $5M to $50M. Annual FIA sales rose from $3M to $35M. And annual life premium rose from $50K to $1M.