The Probate Lawyer Blog

When most people think of Hugh Hefner, they picture the famous Playboy bunny logo, young and buxom blonde women by his side, and his ever-present robe and captain's hat.  But people should also think of his smart business and planning sense.  After all, Hefner started a unique business with $8,000 in 1953 and grew it into a massive global enterprise.  

How Hefner used the resulting wealth to plan for his golden years and beyond was as unique and innovative as the way he lived his life.  It certainly isn't a road-map for everyone, but it worked out well for him.

It started at least as far back as 2010, when Hefner and his second wife, Kimberley Conrad, finalized their divorce after a 12- year separation.  At this time, records from his divorce pegged his net worth at about $43 million plus the value of his Playboy Enterprises stock and real estate.  Those records also revealed his yearly income to be nearly $3.5 million, with his expenses topping out at just over $1.3 million annually.

The big open question, of course, was:  What was the Playboy stock worth?  In 2011, Hugh Hefner partnered with a private equity group to purchase the Playboy stock and take the company private, for a total package worth $207 million.  When the dust cleared, Hefner ended up with a 37% ownership interest in the new company along with an employment contract that paid him one million dollars per year, gave him editorial control over the Playboy brand, and the right to remain in the famed Playboy mansion practically rent free for the rest of his life.

As if founding Facebook  and reaching #16 on Forbes’ ranking of the world’s billionaires wasn’t impressive enough, Mark Zuckerberg – along with his wife, Dr. Priscilla Chan — is out to change the world for generations to come.  But not everyone thinks his motives are pure.  

Zuckerberg and Chan announced their decision to transfer 99% of their Facebook stock to a new charitable-based venture called the Chan Zuckerberg Initiative.  This will do this through a new limited liability company, with the stated purpose to “to join people across the world to advance human potential and promote equality for all children in the next generation.”  The stock will be handed over throughout their lifetimes, with no more than one billion dollars in stock gifted or sold annually for the next three years, according to a recent Facebook filing with the SEC.  Zuckerberg and Chan write that the value of the stock, presently, is about $45 billion, but that will likely grow over time considering their youth (Zuckerberg is 31; Chan is 30).

Zuckerberg and Chan believe that they have a “moral responsibility to all children in the next generation.” They point to society’s obligation to help future lives. By explaining their motivations to their newborn daughter, Max, through an open letter for the public to read on Facebook, Zuckerberg and Chan seek to encourage others to follow their charitable lead. Many public figures, like Warren Buffett, Bill and Melinda Gates, and others, quickly applauded the move.

But some questioned Zuckerberg and Chan’s charitable intent or even gone so far as to accuse them of tax evasion.   They claim that the tax benefit of donating appreciated assets, like Facebook stock, in a manner that avoids capital gains taxes on the appreciation harms society rather than benefiting it. They also point to the choice to use a limited liability company rather than a charitable foundation as proof of Mark Zuckerberg’s less-than-noble intent.