By Peter J Reilly From Forbes

So here is a truly brilliant, if slightly ghoulish tax plan. Jeffrey Webber is a venture-capital investor and private-equity fund manager. His advisor, William Lipkind, came up with a vehicle that would not only defer gain on some of his investments, but also totally avoid income tax when he and his family members cashed in. It’s a real shame that the Tax Court agreed with the IRS that the scheme did not work. My only consolation is that it illustrates a couple of Reilly’s Laws of Tax Planning.

The Plan

Mr. Webber established a grantor trust that purchased “private placement” variable life insurance policies insuring the lives of two elderly relatives (That’s the ghoulish part). The premiums paid to Lighthouse Capital Insurance Co. (Cayman Islands) after deduction for mortality risk and administrative charge were placed in separate accounts. The accounts were segregated and invested in start-up companies that Mr. Webber was intimately familiar with. They did quite well.

The Third Law

Reilly’s Third Law Of Tax Planning holds that “ Any clever idea that pops into your head probably has a corresponding rule that makes it not work “. For the clever idea of running your aggressive start-up portfolio with money technically owned by an insurance company, but meant to benefit you or the natural objects of your bounty, there is Revenue Ruling 1977-85.

A policyholder of an investment annuity contract issued by a life insurance company must include in gross income, under section 61 of the Code, interest and dividends or other income received by the custodian of the investment account created in conjunction with the contract and over which the policyholder has investment control.

Not exactly Mr. Webber’s facts, but pretty close.

The Fourth Law

Reilly’s Fourth Law of Tax Planning is “Execution isn’t everything but it’s a lot”. The execution of this plan depended on something called the “Lipkind Protocol”. All decisions relative to the investments in the assets funded by the premiums had to be made by an independent investment manager. The policyholder could set the overall investment philosophy – “high risk” investments, including private-equity and venture-capital assets – and make specific recommendations. The investments were held in a special purpose entities including one called Boiler Riffle.

The “Lipkind Protocol” put a buffer between Mr. Webber and the investment advisor.

Mr. Lipkind explained to petitioner that it was important for tax reasons that petitioner not appear to exercise any control over the investments that Lighthouse, through the special-purpose companies, purchased for the separate accounts. Ac-cordingly, when selecting investments for the separate accounts, petitioner followed the “Lipkind protocol.” This meant that petitioner never communicated—by email, telephone, or otherwise—directly with Lighthouse or the Investment Manager. Instead, petitioner relayed all of his directives, invariably styled “recommendations,” through Mr. Lipkind or Ms. Chang.

In the end, though, it was really not possible to disguise the fact that Mr. Webber was calling all the shots.

Although almost all of the investments in the Policies’ separate accounts consisted of nonpublicly-traded securities, the record contains no compliance records, financial records, or business documentation (apart from boilerplate references in emails) to establish that Lighthouse or the Investment Manager in fact performed independent research or meaningful due diligence with respect to any of petitioner’s investment directives.

The record includes more than 70,000 emails to or from Mr. Lipkind, Ms. Chang, the Investment Manager, and/or Lighthouse concerning petitioner’s “re-commendations” for investments by the separate accounts. Mr. Lipkind also appears to have given instructions regularly by telephone. Explaining his lack of surprise at finding no emails about a particular investment, Mr. Lipkind told petitioner: “We have relied primarily on telephone communications, not written paper trails (you recall our `owner control’ conversations).” The 70,000 emails thus tell much, but not all, of the story

The net result of this process was that every investment Boiler Riffle made was an investment that petitioner had “recommended.” Apart from certain broker-age funds, virtually every security that Boiler Riffle held was issued by a startup company in which petitioner had a personal financial interest, e.g., by sitting on its board, by investing in its securities personally or through an IRA, or by investing in its securities through a venture-capital fund he managed. The Investment Manager did no independent research about these fledgling companies; it never finalized an investment until Mr. Lipkind had signed off; and it performed no due diligence apart from boilerplate requests for organizational documents and “know your customer” review. The Investment Manager did not initiate or consider any equity investment for the separate accounts other than the investments that peti-tioner “recommended.” The Investment Manager was paid $500 annually for its services, and its compensation was commensurate with its efforts. (Emphasis added)

In order to have executed this plan perfectly, it would have been necessary for the investment advisor to perform due diligence on each of Mr. Webber’s “recommendations”. The added costs would have taken a huge bite out of his superior returns. This is a reflection of Reilly’s Third Law Of Tax Practice – “ Any reasonably complex tax matter involving significant dollars, regardless of whatever else it might be, is a white collar jobs program .”

Still Not Such A Bad Plan

Even though the income tax piece of the plan ended up not working, it appears that the transfer tax aspects were left undisturbed. Mr. Webber got all that growth out of his own estate and the income tax bite is coming out of his other assets.

There were no penalties.

Mr. Lipkind provided petitioner with “advice.” Mr. Lipkind did not himself render a written legal opinion, but he reviewed and considered written opinion letters from reputable law firms addressing the relevant issues. Three of these opinion letters specifically addressed the “investor control” doctrine; they concluded that the Lighthouse policies, as structured, would comply with U.S. tax laws and avoid application of this doctrine. By informing petitioner that he concurred in these opinions, Mr. Lipkind provided petitioner with professional tax advice on which petitioner actually relied in good faith.

We likewise conclude that petitioner’s reliance was “reasonable.” Petitioner made multiple filings with the IRS setting forth details about the Trusts and Lighthouse, including gift tax returns filed for 1999 and 2003 and Form 3520 filed when the Policies were transferred to an offshore trust. Petitioner did not attempt to hide his estate plan from the IRS. This supports his testimony that he believed this strategy would successfully withstand IRS scrutiny, as Mr. Lipkind had advised.

For their work preparing Trust documents and all other work for petitioner, Mr. Lipkind and his colleagues charged time at their normal hourly rates. Neither Mr. Lipkind nor his firm received from petitioner any form of bonus or other re-muneration apart from hourly time charges. Neither Mr. Lipkind nor his firm re-ceived compensation of any kind from Lighthouse or the Investment Manager. IRS Examination and Tax Court Proceedings The IRS examined petitioner’s timely filed 2006 and 2007 Federal income tax returns.

The absence of “value billing” distinguishes this transaction from the bogus Son-of-Boss and similar offenses against double entry put on by the Big 4 running up to and a bit beyond the turn of the millennium.

From a tax policy point of view, it is clear that this plan should not work. It is taking the favorable tax treatment of life insurance and turning it into the perfect tax shelter. Nonetheless, I admire its elegance. It is also worth noting that if you had a genius investment advisor that was independent, the plan probably does work.

Other Coverage

I may be nearer than usual to the head of the pack on this one. Paul Neiffer takes the case as a caution to follow the rules. Lew Taishoff had something and elegantly addresses the penalty issue.

But trusty lawyer wasn’t an enabler; he didn’t get more than his usual hourly rate. And relayed JT’s orders to the Caymans. But he did do some due diligence, had credentials, knew the whole story, and JT didn’t understand variable life insurance and its anfractuousities.

JT beats the 20% chop.

For more on this story go to: http://www.forbes.com/sites/peterjreilly/2015/07/02/jeffrey-webbers-cayman-insurance-shelter-nixed-by-tax-court/