Julia Roberts in thigh-high pirate boots and fishnet stockings held together by safety pins walks like a stomping pony through the lobby of the Beverly Wilshire Hotel. There, she is met by Richard Gere, who is wearing a finely woven and bespoke three-piece suit. Arm in arm they take the elevator to the penthouse suite. And so goes the movie Pretty Woman.

But stay with me in the lobby. Walk with me past the displays for luxury boutiques—Stefano Ricci, Louis Vuitton, David Webb, Panerai—and Wolfgang Puck’s Cut lounge and restaurant, to the driveway which separates the front building of the hotel from its rear tower. Maneuver, as I do, between a Rolls-Royce Phantom and a Lamborghini Aventador SuperVeloce roadster, and wait as a Mercedes-Maybach S 600 rolls by. Step to the other side of the driveway, push open the gold-plated door and enter the plush environs where real billionaire business gets done—in the ballroom and function rooms on the second floor.

In the grand ballroom on a sunny autumn day not too long ago, Thomas Handler, an advanced planning attorney focused on the analysis and structuring of sophisticated estate plans and family offices, was giving a presentation to a gathering of family office executives. He spoke about the need for reform. He advocated for transparency. And he prognosticated the future (it’s virtual).

Handler is one of the most respected tax and estate lawyers in the world. His Chicago-based firm, Handler Thayer LLP, operates all over the globe and has won numerous awards for its outstanding service to the likes of billionaires, celebrities and athletes.

A Handler speech at the podium can go from the obscure bit of U.S. tax law involving naked grantor retained annuity trusts to a discussion of wealth trends in China. His deep knowledge set is fostered by experience. (He has been steeped in the wealth arena for nearly 30 years, and received the 2017 Family Wealth Alliance Leadership Award for Lifetime Achievement.) So when Handler explains where and how family offices are highly vulnerable to wealth disintegration, or where estate plan protections break down most, or why wills can be contested, it’s worth pulling up a chair and listening to what he has to say.

I’ll attempt to guide you through Handler’s most astute observations from the talks he’s given, as well as from our one-on-one conversations, e-mails and interviews. But first, let’s get to know him a bit.

He has a bachelor’s degree in accountancy from the University of Illinois at Urbana-Champaign and a law degree from DePaul University College of Law in Chicago. He worked his way through college doing taxes—invaluable experience it turned out, as he was able to leverage his client base and working knowledge of the tax system into a job at a major law firm. There, he quickly schooled the senior partners on the need for an updated computer system and penned a law review article that is still cited in cases today: “Tortious Interference with Contract and Prospective Advantage in Illinois,” which he wrote with Ronald Broida for the DePaul Law Review in 1983. For his efforts, he got a big “thank you,” but that was it.

“Brought in a bunch of business, wrote a white paper, published an article, and there was no bonus,” he recalls.

With his client base and referrals from classmates, Handler decided to go out on his own. His plan from the get-go was to seek out higher-net-worth taxpayers who owned businesses—an underserved niche he knew from preparing taxes. The strategy paid off, and soon his firm was getting a higher batting average with the very wealthy. So the path forward was seemingly clear. This was in the 1980s, before the Family Office Association—the first such organization of its kind—was even formed. His experience now includes tax controversy, estate contests, tax litigation, public accounting and corporate and foundation directorships. He even recently penned his first article in Chinese for a major Asian financial publication.

OK, so this is the guy we are listening to. A rather impressive resume, yes? That means he should know the alchemy to a successful family office.

“I think that integration is the absolute top element that is consistently missing in that the family office structure and planning is not tied into the family life, or culture, or their businesses, or their estate plans, or their tax plans. In fact, often all those plans were done by four or five, 10, or in one case that I know of, 31 law firms! So the result is it’s not integrated. It’s not elegant. You know, there are contradictory, conflicting elements,” Handler says.

Conflicts bring up the most loaded word in the high-net-worth vocabulary: risk.

“Things that achieve a tax objective can result in an estate cost. Or you can achieve a tax objective and include a prenup that creates an estate plan conflict. So doing this at a high level is challenging and requires expertise,” he says. “As a result, these families rarely have a big enough appreciation of risk management. They don’t realize the kind of risks that they’re subject to. They don’t systematically minimize liabilities, or buy sufficient insurance, or have umbrella policies.”

Handler speaks with passion, even when it’s about minutiae. Why? Because it’s important. It’s what sets the bar.

“The lack of crossing the ‘t’s’ and dotting the ‘i’s’ is highly problematic. We advocate using an implementation checklist. So it’s much more of what an auditor would do in a public accounting audit. You go through each step, tick it off, and sign it. Somebody reviews it, they tick it off, and sign it. And you can’t close the file until all those pieces are done. To give you an example, somebody makes a gift year-end. First, the asset has to be transferred, gotta be valued. We do that valuation under privilege. We then would do a declaration of gift, making sure that the donor signed it and that the trustee it went to accepted it. Now we have paperwork on both sides.

“Next, we make sure it physically got transferred by the brokerage firm that’s actually in the trust. And then we make sure that the equity ledger of the entity that it came out of gets updated to reflect that the capital came out of the account. And then a gift tax return has to be filed. And that return needs to have a valuation report attached to it and needs to, in the case of our client, needs to be generation-gifting tax allocation, in addition to just the disclosure of the gift tax. So to get that done, if you miss any of those steps, you’ve got a potential problem and a risk.”

Whew. I am exhausted just listening to that blistering account of what it takes to merely make a single gift as an ultra-high-net-worth investor. But I get how important details matter. That is my takeaway. And while I don’t know diddly about estate planning or family office structures, Handler’s command of the small details is impressive. Which is why, I suppose, billionaires hire him.

Often, his clients don’t start off with such huge sums, however; they grow into it. And that creates even more complexities. Take the case of those naked transactions, for example. This is when someone uses company stock directly—and that is important, the use of actual stock—to fund an estate planning vehicle such as the grantor retained annuity trust (GRAT). It can be a brilliant vehicle to reduce estate taxes at death. Sam Walton famously used one, so that when he died his estate had reportedly only thousands of dollars left in it and a pickup truck. The bulk of assets flowed to his heirs. But if a GRAT isn’t designed properly, it can be disastrous.

“We’ve had this happen with newer family offices,” Handler says. “One of our billionaire clients made numerous transfers and let his brother be the trustee. The brother was also the general partner of several family partnerships. And ultimately, they kicked my client off the board of the largest company in the world in its space—a public company that he founded and served as chairman of. They kicked him off his own board and disenfranchised him from his own company. And we ultimately had to pay off the uncle, who my client made rich, to get the company back. So we took back the public company, ultimately took it private in a series of difficult and complicated transactions.

“At the front end, had he not given them the stock [and instead used family partnership or family limited liability company interests], he would have retained control. He would have been able to vote that stock.”

Handler notes that 90% of the strategies used out there by estate planners are done on a naked basis.

To be sure, there is no way to stop any one from litigating anything. But there are ways to reduce the possibilities for contestments.

Let’s take a look at some of the most well-known estate battles: Anna Nicole Smith’s $300 million contest of the J. Howard Marshall II estate; the Leona Helmsley $12 million estate contest over the amount she left to her dogs; a $233 million contest from the $7.7 billion Sumner Redstone estate brought by his daughter and son; and who could forget the $1 billion contest by 11 family members over the value of the $15 billion Jay Pritzker estate and who got what?

Handler has had to step into the snake pit of estate plan contestments, many of which he says could have been avoided with simple acts of communication.

“In the process of doing the estate plan itself, we have the opportunity to coach the family to inform people either during their life or by using something called a ‘letter of wishes’ or an estate plan adjunct letter to explain why something happens. [For example], if there are three children and two are treated the same and the third one gets less, the third child may forget that he or she had a $50,000 loan to come out of their share because it never got repaid. So we recommend a letter. It could say, ‘Hey, I want you to know that I love you. I’m trying to treat you all equally, and that’s why you don’t have the same distribution as your two siblings.’”

Also included in a letter could be emotional things, Handler says. For example, “I gave you this painting because I wanted you to have some connection to your grandfather.” That type of thing.

A letter of explanation can help people avoid the stress, the anger and the animosity that can break apart a family and make the relationships among that generation of siblings worse. Such anger can also lay the foundation for bad relations among later generations.

“Communication is the key in helping to identify steps for households,” Handler says. There is another edge to the sword, as well. He has seen bad communication cause ill will. This kind of communication usually comes in the form of a threat; something like, “Look, if you challenge this, you need to know that you’re getting air.” Such provocations rarely end up doing just service to the estate.

With a solid estate plan in place, a family office can be more efficacious and produce better capital performance—and perhaps even beget mergers and acquisitions with other family offices.

The number of family offices is still growing.

According to EY, there are more than 10,000 family offices in the world. Capgemini puts the U.S. total above 3,000.

Handler sees growth in virtual family offices, multifamily offices and single family offices—in that order—whereas internationally the ranking is mostly reversed, he says.

“There’s been a global proliferation of wealth,” Handler reckons as the reason for the surge in family offices. Tax reform in the U.S. may set off another growth spurt and awaken the super wealthy to the need for a more organized family office structure.