The Best Insurance Sale I Ever Made Took 18 Months (And Why That’s Actually Good News)

I want to tell you about a deal that almost didn’t happen.

Not because the client didn’t need it.

Not because the numbers didn’t work.

But because we walked into a situation where the accountant had already designed the entire solution.

Estate freeze. Check.

Family trust. Check.

Pipeline strategy to minimize tax at death. Check.

Everything wrapped up in a beautiful tax-minimization structure that, on paper, looked airtight.

An advisor I work with brought me into the case.

He’d been working with this business owner for a few years, knew there was something there, but couldn’t quite crack it. The accountant kept shutting down the insurance conversation with “we’ve got it covered.”

So he called me.

Not because he couldn’t do it himself, but because he knew this was going to take a specific approach. And he was smart enough to bring in support.

When we showed up to the first meeting, the business owner looked at us and said:

“We appreciate you coming in, but honestly, we’re pretty well covered. Our accountant has been working on this for two years. We’ve got it under control.”

Most advisors would have heard that and either:

 1. Pushed harder (and lost the deal)

 2. Walked away (and lost the deal)

We did neither.

Instead, I said:

“That’s great. Sounds like you’ve got a solid team. We’re not here to sell you anything today. We just want to understand what you’re building so we can see if there’s anything we’re missing. And if there’s not? That’s totally fine.”

And I meant it.

The advisor nodded. He knew this was going to take time.

The First Six Months: Just Listening

For the first six months, we didn’t pitch a single thing.

We asked questions.

We reviewed their structures.

We looked at their freeze.

We understood their trust.

We mapped out their pipeline strategy.

And here’s what I noticed:

The accountant wasn’t wrong.

Everything they were doing made sense.

The pipeline strategy was solid. It would eliminate one layer of tax at death. Smart planning.

But there were gaps.

Not mistakes. Gaps.

Gaps that insurance could fill in ways their current plan couldn’t.

But I didn’t say that.

Not yet.

Because they didn’t trust us yet.

The accountant trusted me. When I was at the insurance company, this was the type of work we did with advisors. We helped them move along and close these complex deals with our technical team. I’d worked on dozens of cases like this. Met accountants across the country. Built relationships on deals that took months, sometimes years.

So he knew me. He knew I wasn’t going to come in swinging with generic solutions.

But the business owner?

He was still watching.

Still testing.

Still wondering if we were just another team trying to jam a product into his life.

Months 7-12: Planting Seeds

Around month seven, something shifted.

We were in a meeting reviewing their estate plan, and the business owner mentioned something offhand:

“You know, the one thing that worries me is liquidity. If something happens to me, the company’s worth $15 million on paper, but there’s no cash. My wife would have to sell assets to pay the tax bill, and that puts her in a terrible position.”

I paused.

Then I said:

“Yeah, liquidity is part of it. But there’s something else here. Your accountant did a great job with the pipeline strategy. It’s going to save you a ton of tax. But here’s what most people don’t realize: the pipeline strategy minimizes the tax bill, but it doesn’t grow the estate. Insurance does both.”

He looked at me.

Then he looked at his accountant.

The accountant leaned forward.

“What do you mean?”

“Okay, so right now, with the pipeline strategy, you’re eliminating one layer of tax. That’s smart. You’ve minimized what goes to the government. But you haven’t added anything to what goes to your family. The estate is the same size, just with less tax erosion.”

“But if you layer insurance on top of the pipeline strategy, you’re not just minimizing tax. You’re actually increasing the total value of the estate. Your wife and kids end up with more. Not just ‘less tax,’ but more money, period.”

The accountant sat back.

“Huh. I hadn’t thought about it that way.”

That was the first crack.

Not because we pushed.

But because I understood their plan well enough to show them what it didn’t do.

Months 13-18: Building the Solution Together

Over the next six months, we didn’t “sell” anything.

We collaborated.

The accountant ran projections.

I brought in the technical team from the insurance company to run illustrations and model scenarios.

The advisor stayed close to the client, managing the relationship, keeping things moving without pressure.

We compared scenarios:

 ∙ Pipeline strategy alone: Tax minimized, estate stays the same size

 ∙ Pipeline strategy plus insurance: Tax minimized, estate grows by millions

And slowly, the business owner started seeing it.

Not because we convinced him.

But because the math convinced him.

The insurance wasn’t replacing their strategy.

It was amplifying it.

It gave them liquidity.

It protected against forced asset sales.

And most importantly, it meant his family would inherit significantly more wealth.

And by month 18, when we finally sat down to sign the application, the business owner looked at the advisor and said:

“You know, I’m glad we took our time on this. A year ago, I didn’t trust this. Now I can’t imagine not having it.”

That deal closed at $450,000 in annual premium.

But it took 18 months.

And here’s why that’s actually good news.

Because most advisors give up at month two.

They hear “we’re all set” and they walk away.

Or they push too hard and get shut out.

But the reality is:

Big deals take time.

Complex families take time.

Sophisticated clients take time.

And if you’re willing to play the long game, you win deals other advisors will never even see.

Here’s What Actually Works (The Part Nobody Talks About)

When you’re dealing with business owners who already have accountants and lawyers designing solutions, you can’t come in hot with “insurance fixes everything.”

That’s a fast way to get ignored.

Instead, you have to do this:

1. Understand their plan first.

Before you say a single word about insurance, learn everything they’re already doing.

What’s the freeze structure?

What’s the trust doing?

Are they using a pipeline strategy?

What are they trying to accomplish?

If you don’t understand their plan, you can’t position insurance in a way that makes sense.

2. Position yourself as collaborative, not competitive.

You’re not there to tell the accountant they’re wrong.

You’re there to add to what they’re building.

The minute you start fighting with their accountant, you lose.

The minute you start working with their accountant, you win.

And if you need support on these deals, bring in your wholesaler or specialist. That’s what we’re here for. To help you navigate the technical details, ask the right questions, and position the solution in a way that lands.

3. Ask the questions they haven’t asked yet.

The reason most accountants default to “you don’t need insurance” isn’t because they’re against it.

It’s because they’re solving for tax minimization, not estate growth.

So you ask:

“Okay, so the pipeline strategy minimizes the tax. That’s great. But does it grow the estate? Or does it just preserve what’s already there?”

“If we layer insurance on top of the pipeline strategy, what happens to the total value the family receives?”

“What happens if we need liquidity at death and have to liquidate investments to cover the remaining tax bill? What does that do to the estate’s value?”

These aren’t objection-handling techniques.

These are legitimate planning questions.

And when you ask them, you’re not selling.

You’re uncovering gaps in their current plan.

4. Give them time to think.

This is the hardest part.

Because we want the deal now.

We want the premium now.

We want the commission now.

But big deals don’t work that way.

Big deals require clients to:

 ∙ Process the information

 ∙ Talk to their advisors

 ∙ Run the numbers

 ∙ Sleep on it

 ∙ Come back with questions

 ∙ Run more numbers

 ∙ Get comfortable

And if you rush that process, they’ll shut down.

But if you give them space, they’ll come to the conclusion themselves.

And when they do?

The deal is ironclad.

Because they convinced themselves.

5. Be okay with walking away.

This is the secret weapon.

If you’re willing to walk away when insurance doesn’t make sense, clients trust you more.

Because they know you’re not just selling.

You’re solving.

And the moment they feel that, everything changes.

The Takeaway

If you’re frustrated that deals aren’t closing fast enough, here’s what I’d challenge you to think about:

Are you trying to close deals, or are you trying to build trust?

Because closing deals is about speed.

Building trust is about patience.

And the advisors who dominate this industry over the next decade won’t be the ones with the best pitch.

They’ll be the ones who can sit in a room with an accountant, a lawyer, and a business owner, and not feel the need to be the smartest person in the room.

They’ll be the ones who ask better questions.

They’ll be the ones who understand the client’s world well enough to see gaps nobody else sees.

They’ll be the ones who understand that a pipeline strategy is good, but a pipeline strategy plus insurance is game-changing.

They’ll be the ones who are willing to take 18 months to close a $450,000 premium case.

Because that’s the game now.

Slow is fast.

Trust beats tactics.

Collaboration beats confrontation.

And if you’re willing to play that game, you’ll win deals that other advisors don’t even know exist.

If you’ve got a case like this and need support working through it, reach out. That’s what I’m here for.

Talk soon,

Andrew