Sales coach, speaker and former insurance agent Tom Hegna teaches others to use the examples to generate business. First, there is the sheer recognition factor. “They’ll say, ‘Oh, I remember Evel Knievel or Marilyn Monroe,’” Hegna said. “And then you can say, ‘Let me tell you a story about him or her.’”

That’s when the discussion over how an estate lost millions of dollars can lead to a conversation about a will, trust or life insurance.

“You can show how the problem could have been solved if they had just taken a few simple steps,” Hegna said.

He has seen certain patterns over the years that are instructive for clients.

“One is that they’ve had multiple relationships, maybe multiple ex-spouses, and they’re living with somebody they’re not married to,” Hegna said, describing a situation begging for an advisor’s attention. “If you’ve got a client who’s been married three times, that should set up a warning bell. They are much more likely to have an estate planning problem than the person who’s been married to the same woman for 52 years.”

Some of those problems could be a 401(k), the beneficiary of which has not been changed since wife No.1; same with a life insurance policy. If they aren’t married, there’s always the issue of the spousal deduction they miss out on, as the actor Philip Seymour Hoffman did with the mother of his children. He left an estimated $35 million, but it is exposed to a substantial tax bite.

A popular case to discuss now is James Gandolfini, because he was so recently high-profile with his Tony Soprano role. When he died at 51, he left about $70 million and a big tax bill.

Hegna recommends a strategy involving an annuity and life insurance that can help with ultra-high-net-worth families.

“This is a two-step strategy to get money out of the estate,” Hegna said, using the example of a $50 million estate. “He may take $20 or $25 million and purchase life-only, or if he’s married, a joint-life annuity. When they die, that entire $25 million is out of the estate. Zero estate taxes because that money’s gone. Now, is the family going to be unhappy if $25 million is gone? No. Because that was paying the premiums on a $50 million life insurance policy in irrevocable life insurance trusts outside of the estate. So, he uses the immediate annuity to get money out of the estate and pays the premiums on the life insurance that builds up outside of the estate. And that is a very powerful strategy of using multiple products.”

How about the merely really wealthy? Is estate planning less of an issue because of the high federal exemption of $5.25 million for an individual and double that for a couple?

Hegna advocates a way for even that to work for an agent or advisor.

“I say you can sell up to the exemption,” Hegna said. “You have somebody like Adam Yauch (of The Beastie Boys), who had about $6.4 million. But he could leave $10.5 million for his wife. In that case, you could go and say, ‘I can sell you a $4.1 million policy and when you die, you’re going to maximize your estate tax because you’re allowed to give $10.5 million tax-free to your kids or grandkids, or whoever you want. So, let’s do a $4.1 million policy to maximize your tax-free giving.’”

Another important planning point is when the family controls a large business, as was the case with William Davidson, the owner of the Detroit Pistons. Although that estate was worth billions of dollars, even much smaller businesses can throw a family into turmoil after the owner’s death.

“Often, there’s a fire sale when they have to liquidate within a certain period of time, because the IRS doesn’t give you forever,” Hegna said. “With family businesses, farms and ranches, it’s the same thing. It comes back to treating the family equally versus equitably.”

Treating the family equitably might not mean equal distribution. “A lot of business owners just say, ‘Well, it’s going to go equally to my three kids,’ when that is probably not what they should do unless three kids are actively involved in the business and get along really well.”

Here is another opportunity for life insurance. “You need liquidity from life insurance to either buy out the children who are not in the business or buy out the business partners not in the business. Then, if you really want to get complicated, as business owners get divorced and wives have 50 percent of their deal, you could wind up with a business partner they didn’t even like. All of this could be solved very simply through life insurance.”

An important aspect is to not talk about life insurance itself, but talk about what it does, Hegna said.

“People say, ‘Oh, life insurance. I don’t need life insurance.’ No, what you need is when you die, a bunch of money can be there to solve the problem of your business. If there were another product that could do it, I’d recommend it. But stocks, gold, commodities and bonds can’t provide the right amount of money at exactly the right time. So, life insurance and annuities provide the perfect benefits at exactly the right time.”