Ben Wentworth (not his real name) was one of my favorite clients mostly because he had no problem saying to anyone whatever was in his head regardless of circumstances. Yet somehow, after his outburst, the recipient would as often as not like him more than ever. I don’t know how he did that. But he did.

I once saw him bark at a Judge who was forcefully telling him to accept a settlement. Ben said something like this: “Judge, you sit there in your black robe on your high bench and you get a paycheck like clockwork every two weeks and haven’t had to worry about making a payroll in your life. You’re telling me to accept a deal that is not only unfair but means I won’t pay a promised bonus to my good employees. And I am to do that ‘cause otherwise I risk a lot of my money if I lose. You just can’t know what’s going on in my mind since you’ve never been there.”

The Judge, a tough old codger himself, had heard it all before. He sighed. “I once practiced corporate law, Mr. Wentworth. I know the ramifications of cash flow.”

Wentworth leaned forward. “Practicing with the big boys is not working in a company like mine with fifteen employees. Make you a deal, Judge. You agree to come to my next employee meeting tomorrow, you tell them you told me not to bonus them what I had promised because I might lose this case and I should play it safe. You watch their faces. One of my employees was planning to make a down payment and get out of a dangerous neighborhood. Another has a mother with huge medical bills. And I should play it safe? What kind of a man would I be then? Breaking my promise to them. That’s dishonorable.”

The Judge leaned back and gave him one of his famous cold looks. Unfazed, Wentworth shook his head. “Judge, I can’t break my word to them unless I have no choice. If I lose, I have no choice. If it’s a risk, then I have to take it. I think I owe it to them.” He spoke with utter conviction. I watched the Judge tilt his head to the side slightly.

Then the judge smiled. “OK, you’re warned. You risk it all. You make that decision with full knowledge of the possible results, then it’s on your head.”

Ben grinned. “Judge, I run a business. It’s always on my head.”

The Judge had grinned back.

A week later, when we came out pretty well, the Judge stopped Ben in the hallway as we were leaving the court house. He shook Ben’s hand. “I respect you for what you did, Mr. Wentworth. And why you did it. Don’t see that often. And I see a lot of cases.” And that was a Judge who he had essentially told to drop dead. How did he do that?

So, fifteen years later, when he had built his company to the point where it was worth over nine million dollars (double that in today’s dollars) and he came to see me about estate planning for multi generations, I expected him to have some odd ideas as to what he wanted to do with his wealth. And he did.

He had gained perhaps thirty pounds since our day in court but when he had an idea he was still as adamant as ever. He now usually dressed in a rumpled suit, an out of style tie not quite tied correctly, scuffed shoes, white shirt, large gold watch. His daughter had three kids, his son two kids and we were meeting to discuss generation skipping trusts. This was over ten years ago and the estate tax that would have been levied on his estate when both he and his wife died was in excess of four million dollars, due nine months from date of death.

So we drank bad office coffee and discussed the many estate planning tools available to protect the next generation and minimize some of those taxes. Use of minor trusts, a planned program of gifting, revocable trusts, irrevocable trusts, not to mention life insurance trusts, all which made good sense and we spent over two hours discussing the complex structures that would soon be executed. He loved his family, told me he loved his grandchildren more than he ever loved his “troublesome” children and wanted to make sure they enjoyed the bounty of his success.

Then he leaned back in the conference room chair, glanced at the law books that cover our walls, then looked out the window at the other high rises. I let him ponder whatever he was pondering and when he looked at me again after a minute or three he had that same expression I saw when he told off the judge.

“You know, I can make those kids and grandkids rich for life. Right now. Can make it so they never have to worry about a thing, never have to struggle as I did, never have to worry a day in their lives about money. I can do that and do it cheap, tax wise, right?”

“That’s why we’re meeting, Ben. Protect the family, help them on their way, save taxes.”

“But, you know, there’s help and there’s help. I wonder if I’m helping them or hurting them.”

I just looked at him. He saw that and grinned. “I mean, I may be hurting them more than helping them. I may be gutting them. Cutting out their gumption. I’ve seen it. Poor little rich kids.”

“You want to explain?”

He sighed and drummed his fingers on the coffee mug. “My best friend in college. Ray Barry. Twice as smart as me, twice as charming, good at football, quarterback, popular with the girls, scored at the top of all the tests. Good contacts, his dad a CEO of an international, he was going to go to business school, set the world on fire. Tell you, I was jealous of him though I loved the guy. Had everything going for him. Hard worker, too.”

“You’re making me jealous of him, as well.”

“You would be. Know what he’s doing now?”

“I bite.”

“Nothing. Pretending he’s a consultant. He lost his fifth job in a row last year. Now he’s a self employed consultant on environmental planning for houses or some such thing. Goes into people’s homes and tells them what their electric bill is and how much they might save if they go solar. Makes, maybe, thirty thousand a year. Divorced twice. Detox twice. Nice enough guy. But a failure.”

“Advising people on environmental planning is not a failure, Ben.”

“It is for him. He was a sure fire star, I’m telling you. I expected him to be running GM or Exxon or some such thing. That good. But now he can’t hold a job and the only guy who will employ him is himself…since he won’t fire himself.”

I waited to hear why Ray Barry mattered to our discussion but Ben was quiet, studying his hands on the table. Then, after a pause, he went on. “His Dad destroyed him, really. With money.”


Ben looked at me. “His Dad was making good money, really good money, so he went to see someone like you and they set up this complicated structure but what it came down to is that Ray knew he would inherit two million or so from this Trust when he was twenty five, another three million when he was thirty and he’d get that no matter what he did…or didn’t do. He was rich before he got his first job.”

“Lucky him.”

“It destroyed him. I mean, he didn’t kill himself or anything. He stayed the same guy with me. And he kept in school and graduated and he went to work…but…but something wasn’t there. He just couldn’t compete with the hungry fellows like me. He’d work and work steady…but that was all. Just worked steady. Didn’t really do more than that. And as the years went by he kept being passed over.’

“You blame it all on money in his bank?”

“Naw. I’m sure other things were going on. But everyone else in our class, the guys without much money, well we somehow passed him by. He didn’t quite do the best work. Knew his stuff…but somehow not quite good enough to make the fast track.”

“Maybe he wasn’t as good as you first thought.”

“Well, it wasn’t just me who thought he was the top guy at school. He got straight As, won all the competitions in school. Was interviewed by every company you could imagine, he was number one or two in our business class. Then, about the time we graduated…this trust was created. And…after that there was something, I tell you, that was somehow missing in him and his drive. Hunger, maybe. A need to make enough to support himself or his kids…his money was always going to be there whether he worked hard or not.”

“Lots of rich people work harder than poor people, Ben. You’re one.”

“Yeah, I know. I haven’t eased back and I’m rich now, I guess. But there’s a difference. After thirty years of pushing myself, I know it’s up to me to get things done. Learned that in ten or fifteen years of real struggle when if I didn’t crack the nut, I had to close down and let my wife know I failed. Nothing like that for incentive. And once you learn that, you don’t usually forget it. I still worry about making payroll and expenses. It’s part of me.”

“Tell me about it…”

“Yeah, you run a business, too. You know the game. But Ray, well he never had that gut wrenching worry that he didn’t know if he was going to be able to afford sending a kid to college or to private school or going on that vacation his wife wanted. I mean, that type of luxury was already guaranteed whether he worked hard or made mistakes or not…and because of that, his business work was…business was frosting on the cake. Something of interest but not something that can make or break you and those you love.

“How can someone like that compete with a hungry guy like me who stays up at night worrying about making payroll? He didn’t have a chance.”

“But a lot of people who inherit and know they will inherit stay tough and directed. I represent some.”

“Some. But those are the exceptions, I think. Ray is more the rule in my experience. I could mention two or three other guys I know. Good guys. Adequate in business. But with so much money coming to them no matter what that they back off when someone hungry like me enters the race.”

“Maybe it’s just you. Maybe no one wants to take you on.” I was grinning.

He grinned back but stayed serious. “If they know they have it made, why kill themselves working like you and I do? And that lack of direction, of drive, seems to take over most of their lives. From marriage to kids to golf game. They end up playing at life.”

“People work for more than money. To prove themselves. To achieve something.”

“True. Lord knows that’s true. Men..and women for that matter…like to show what they can do. But if everyone knows you are inheriting, even if you make it, they will always question if you could have done it without the money, you know. You gotta know they’re thinking you had it made before you began. So you have to succeed and succeed big or you are double the failure. I think that scared Ray. Hell, it would scare me.”

I was not convinced. “Do you really know what went on in his head that well?”

“He was my best friend. Lots of late night bull sessions when we planned our futures. And I tell you his Dad ruined him by making it so that Ray couldn’t fail moneywise no matter what he did in business. Ruined him by making it so he couldn’t ruin himself. Financially, at least. Ruined him as a fighter. I knew the dad. Great guy. Good guy. Smart, directed. Wanted to protect his son. I think he did just the opposite.”

“You assume making money and showing you’ve made it defines success. Maybe he’s happier than you are.”

“He had drug problems and divorces and when I see him I don’t think he’s that happy.”

“Maybe there’s more to life than financial success and making it on your own.”

“I’m not just saying earning money was gutted. Winning…competition…having to do the extra night of work or skip the vacation…that was gutted. It’s different if you earn it. You feel proud that you did it, proud that you succeeded and know you can make more. If money drops onto you before your first real job…well, I think it guts you. It gutted him. And you and I know a few others…”

We went through a list of five or six people we both knew who inherited a lot when young. All were good people. But only two of them really made it in business or a profession. One became a doctor. One in construction. The others had very, very good lives…but, as Ben said, somehow never made it to the top if they inherited before they learned what earning money was all about. Having a lot of money after you learn the hunger…well, that seemed to have no effect. At least according to our small crude survey.

Ben walked to the window and looked out. “So, this may sound stupid but this is what I want to do. I’m going to do a matching grant. Like on public television. They don’t get the money unless they succeed, at least a bit.”

“They could fail and it might not be their fault. Then they get hit by a double whammy? And what do you mean by success? Someone teaching in a public school could be a great teacher and earn next to nothing. You want to punish him or her for not making big bucks?”

“Of course not. We just define success as doing something that means something, not just spending money and flitting about. That’s what I mean.”

“How do we define that precisely?”

“You’re the smart lawyer. You figure out a system in which if it isn’t their fault, they don’t get punished. And if they are doing good…raising a family, helping others, things like that, they don’t get punished by the Trust. But this they have to know-if they don’t earn money or work hard to earn it or help others, they don’t get more from me. They have five or ten years to earn it or do good and if they don’t, it goes to charity. Simple as that.”

I knew that voice. The same voice Ben used with the judge.

And I thought he just might be right. Not always…I knew some pretty strong people who had managed to keep the drive despite large sums gifted to them. But I also remembered a beer I shared with one of those that had known he would be rich from the age of ten. We were in a restaurant while we waited for his wife to join us for dinner. He had just completed a tough negotiation that expanded his business into a new market and I was complimenting him. He was typically self deprecating and then made a comment I remember well.

“No one back at corporate will think I did so well. They’ll just figure I succeeded because of who my Dad was, because I have the contacts put there by Dad. That it was given to me.” His voice was uncharacteristically bitter.

I was surprised at the tone of his voice. His Dad had been in the same company but retired a few years before and, yes, had gifted via trust some millions to my friend. But I happened to know my friend was working harder than most of his same level colleagues (I represented one of them) and knew that his success was not based on his Dad’s old business friends, most of whom had long retired themselves.

“You landed the contract. They’re just jealous.”

“Some are. But all think I had an unfair head start. Angers them. I always have two strikes against me. They are always waiting to see me fail so that I get my comeuppance, that’s what I think.” He finished his beer and changed the topic.

And I also had a good friend in law school, a truly brilliant student who won all the moot court competitions, was on Law Review, courted by all the big firms and then in his third year inherited a million or so. I remember his comment to me as he dropped out (just for a semester which turned into never finishing law school.) “Just want to see what life is really about. Take a little time to look around and live a bit before joining the rat race.” He never did join the rat race, I suppose. And he may have been right. He’s traveled the world, played with a couple of businesses, has lived in Europe and Asia and studied Buddhism. Good company and has remarkable stories.

But I know his father, one of the bastions in a large law firm, was deeply disappointed, calling his son a “hippie loafer” at all family gatherings.

So, maybe Ben was right. He certainly liked the plan we created. If an heir convinces the Trustee that he or she has either demonstrated prowess at a career, be it money making or foundation work or teaching or research…then the trust funds the life style by matching the monies earned or funding the good work up to a certain amount or contributing to charity, at the election of the beneficiary. If the beneficiary does not achieve the goals set, the matter is revisited every three years to give the beneficiary the chance to succeed. It’s still too soon to know if it works…though each grandchild seems to be successful and has achieved payment of all sums so far.

And Ben does not participate in the decision making. “I have enough trouble not bossing people around all the time already. If they have to prove themselves to me each three years, then Thanksgiving is going to be a very tough time. No, we set up a committee to advise the Trust and their decision goes regardless of what I think.”

Most clients do not have the desire to create such a complex structure which seems to “judge” the next generations over and over. But most do want some wording requiring their heirs to perform in some way. It seems that most people grasp the fact that incentive can be destroyed by too much generosity. Even without a committee set up, it is possible to give the Trustees the right to demand some “performance” by the beneficiary that may address the issue.

Then again, one client, when told of Ben’s plan, was not impressed. “That guy thinks being Type A personality is somehow what life is about. Wonder how Van Gough or Einstein would have done under such a plan…one a failed artist, the other a patent clerk in the Swiss office, neither having the type of personality your guy seems to want. Seems to me they did OK.”

Maybe. But I expect both those men had drives that made money irrelevant. It’s for the rest of us that we may have to ponder whether too much money too easily obtained can corrode the dynamism that seems to be needed in this modern world.