You wouldn’t sell your house to the first stranger who knocks. So why would you do it with your life insurance policy?

In the world of life settlements, offers can range from pennies to windfalls. It’s a bit like stepping into an auction where the painting on the block happens to be your policy—and how it’s presented can mean the difference between a polite yawn and a bidding war.

Let’s take a walk through the numbers, shall we?

A 73-year-old gentleman, facing a premium squeeze, sold one of his policies for $97,500. Fair? Sure—if you like leaving hundreds of thousands on the table. But when Windsor helped him take his second policy to market—smartly and strategically—he walked away with $310,000. That’s not luck. That’s leverage.

As Don Draper might say: “You don’t sell the thing. You sell the idea of the thing.”

The Power of Multiple Offers

Casting a wider net gives your policy room to breathe. More offers = more competition. And competition, my friend, is capitalism at its finest. Providers sharpen their pencils, private investors join the fray, and suddenly what was once a forgotten financial burden becomes a valuable asset.

Think of it as a cocktail party—if only one person notices you, that’s chance. If five do, that’s charm.

But now for the part no one wants to admit…

The Flip Side: Too Many Cooks (or Inquiries) Spoil the Settlement

Here’s the Alfred Pennyworth moment: “Just because something can be done doesn’t mean it should.”

Push your policy through too many doors, and the market starts to look sideways. Providers aren’t thrilled to see the same case paraded by different brokers. It spooks them. They start to question: Is the seller serious? Is this a setup? Are we the fallback plan?

And Roger Sterling? He’d light a Lucky Strike and say, “Once they smell desperation, it’s all downhill.”

When Over-Shopping Kills the Deal:

• Providers Pass: If they’ve already seen the case, they might not even look again.

• Reduced Urgency: No one wants to bid if they think they’re just being used to boost someone else’s offer.

• Market Confusion: Disorganized outreach leads to missed opportunities, not more of them.

So, What’s the Play?

You don’t need every door in the building. You need the right ones, opened at the right time, by someone who knows what’s behind each.

That’s where a skilled broker—or an aggregator like Windsor—comes in. They don’t just blast your policy across the marketplace. They present it with care, timing, and strategy—so that every offer is serious, and every buyer feels like they might lose.

The Bottom Line

Get multiple offers—but do it like a gentleman. Or a strategist. Or an impeccably dressed advertising executive with a penchant for meaningful exits.

Because the difference between $97,000 and $310,000 is not just who’s buying.

It’s who’s selling.