Laura Deignan · 08 May 2026 · 5 minutes

LEAD GENERATION TIPS

What the Kentucky Derby Can Teach Advisors About Winning the Race for New Clients

Author: Laura Deignan Laura Deignan
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Every year in Stonewood Financial’s hometown of Louisville, the Kentucky Derby gives us hats, horses, mint juleps, and at least one dramatic reminder that anything can happen in a two-minute race.

This year, that reminder came courtesy of Golden Tempo.

Golden Tempo did not exactly coast to victory at the front of the pack. He came from the back, surged late, and crossed the finish line in one of those “wait, where did HE come from?” moments that make the Derby so much fun to watch.

And this year’s story was bigger than the horse. With Golden Tempo’s win, trainer Cherie DeVaux became the first woman to train a Kentucky Derby winner, adding a history-making layer to an already unforgettable race.

That kind of breakthrough does not happen by accident. It takes vision, discipline, preparation, timing, and a team that knows how to execute when the moment arrives.

And while most financial advisors are not preparing for a run around Churchill Downs, there’s a lot we can learn from that kind of finish.

Because in marketing, prospecting, client conversations, and practice growth, the advisor who looks like they’re “behind” is not always out of the race.

Sometimes they’re just waiting for the right opening.

So here are the top Derby takeaways for financial advisors to make sure success isn’t a long-shot.


The Derby is won long before race day

No horse wins the Kentucky Derby because someone woke up Saturday morning and said, “Let’s give this a shot.”

The win starts months, even years, before the gates open. Training. Conditioning. Strategy. A team that knows the horse, the track, the competition, and the moment.

Financial advisor marketing works the same way.

The seminar that fills the room, the Roth conversion conversation that leads to a new client, the Retirement Tax Bill campaign that gets prospects to raise their hand, the client meeting materials that finally make the concepts click – those moments don’t happen by accident.

They happen because you’ve done the prep.

You’ve built the message.
You’ve practiced the story.
You’ve got the right financial advisor marketing tools in place.
You know how to connect retirement tax planning, income planning, legacy planning, and insurance strategies into a bigger conversation clients can actually understand.

That is what separates “showing up” from showing up ready.

At Stonewood Financial, that’s exactly what our software, lead generation tools, and advisor training are built to help you do. We help growth-minded advisors prepare for the conversations that matter most, with client-facing reports, marketing programs, webinars, books, and coaching that turn complex planning ideas into clear next steps.

In other words, we help you get race-day ready.


The best wins require timing

Golden Tempo’s win was not just about speed. It was about timing.

Coming from the back requires patience. Move too early, and you run out of gas. Move too late, and the race is over. The magic is knowing when to make your move.

That is also true in financial services marketing.

Your prospects may not be ready the first time they see your ad, attend your webinar, receive your email, or hear your retirement tax message. But that does not mean the message failed.

It may mean they need another touchpoint.

A better story.

A clearer reason to act.

A stronger connection between the risk they feel and the solution you provide.

That is why a strong marketing system matters. Financial advisor lead generation is not about one lucky post, one seminar, or one email. It is about creating a repeatable process that gives prospects multiple ways to engage, learn, and eventually raise their hand.

The advisors who win are not always the ones who sprint out first.

They are the ones who stay disciplined long enough to be there when the opening appears.


You need more than a fast horse

In the Derby, the horse gets the spotlight. But behind every horse is a team.

Trainer. Jockey. Owners. Veterinarians. Grooms. Exercise riders. Everyone has a role, and every detail matters.

The same is true for a growing advisory practice.

You may be the one sitting across from the client, but your success depends on the system behind you. Your team. Your reports. Your marketing. Your follow-up. Your client education materials. Your seminar presentation. Your appointment-setting process. Your ability to explain taxes, IRMAA, Roth conversions, annuities, life insurance, and legacy planning in a way that feels simple.

That is why Stonewood Financial focuses on more than just software.

Yes, tools like Roth Done Right, Annuity Alpha, Legacy Done Right, and the Retirement Tax Bill lead generator help advisors create better conversations. But the real power comes when those tools are connected to a message, a marketing plan, and the training to use them effectively.

Because a great report sitting on the shelf does not win the race – but a great report connected to the right story, in the hands of an advisor who knows how to use it, can change the entire conversation.


Sometimes the back of the pack is just the beginning

One of the best parts of Golden Tempo’s win is that it was a comeback.

And honestly, that should encourage advisors that there’s room to finish 2026 strong.

Maybe your marketing has been quiet.
Maybe your seminar attendance has been down.
Maybe your Roth conversion conversations have not turned into as much new business as you expected.

Maybe you feel like other advisors are ahead of you.

That does not mean the race is over. It may just mean you need a stronger strategy for the stretch run.

The advisors who grow in today’s environment are the ones who keep sharpening. They keep refining their message. They keep learning how to position tax risk, income risk, market risk, and legacy concerns in ways that clients understand.

They invest in financial advisor training.

They use marketing tools that convert.

They bring clarity to complicated planning conversations.

And when the opportunity opens, they are ready to move.


Golden Tempo reminded us that a race can change quickly.

And teams who have put in the work ahead of the race can come out on top.

With the right preparation, the right message, and the right team behind you, you do not have to be first out of the gate to finish strong.

You just have to be ready when it’s time to run.

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.