Ah, the trials and tribulations of the rich and famous are so fascinating, aren't they?

While the rest of us go along with our lives, dealing with various mundane events, there are some family businesses out there whose issues are the stuff of legends and endless media speculation.

With the Hyatt Hotel chain, not only are there questions of succession to and descent from the throne of business operations, but lawsuits among cousins, brothers and grandchildren. Perhaps the most famous (although nowhere near the two sisters of a rival hotel chain family) 21-year-old Liesel Pritzker successfully litigated against her father Robert Pritzker – age 78 – for looting her trust fund to the tune of $1 billion. She also sought $5 billion in punitive damages. Drop five zeros from that number and that's about the average amount most beneficiaries will receive from their family estates ($50,000!) Following the settlement, the family made a statement that it was pretty dreadful when a daughter who is the beneficiary of great gifts of family wealth and tremendous advantage, sue the very father and others members of the family that made this possible. Well, she felt she was entitled, didn't she?

Need much more be said about Paris and Nicky Hilton of the Hilton Hotel chain, possibly the two most famous sisters alive who have cultivated the art of partying into huge periphery businesses? Looking good, Paris' daily makeup comes at a cost of about $700 per application. Not to take anything away from their incentive to work, they have advanced into clutch bags and shoe design and reality TV shows. Does their visibility increase Hilton room occupancy?

Bermuda's obsession with real estate certainly appears to make a bit more sense (but still not always a desired concentration of assets) when one reviews the spectacular results of "the Donald". Now on wife number three, its probably time to drop the moniker since the name was originally coined by his first wife, Ivana. One of the most successful real estate dealmakers to demonstrate the art of personal branding, Mr. Donald Trump got his start because his Dad, himself a successful real estate icon, early on recognised his son's genius and stepped aside. Said Dad: "Everything he touches turns to gold!"

Meanwhile The Wall Street Journal on May 19 reported that the CEO of the Marriott Hotel chain, 73-year old JW Bill Marriott is probably facing one of the toughest decisions of his life. Should his son, John, grandson of the founder J Willard Marriott, succeed? Or is it time to go with an outsider, the better able to compete globally?

Small family businesses face different but equally difficult succession challenges. The business may not be able to carry the debt needed to buy out the older generation. The younger generation may make unwelcome changes. There may be regrets on both sides after the deal is done.

Corporate stories closer to the average economic strata: Years ago the much wished for (by the parents) sale of a small chain of retail stores to their favourite son, negotiated by one of my former US employers and their tax counsel, still resulted in hard feelings afterward. The father (at that time 72 years old and no longer capable of 16-hour days) stopped me in the street one day to tell me it was the worst decision he had ever made. For starters, he did not approve of the son's new fancy car. Meanwhile, the son (and the business) were doing quite nicely, generating cash to make some pretty hefty payments to Mom and Dad's retirement lifestyle.

And in some quite sad circumstances, the generations are simply unable to accommodate each others visions, needs, and plans for the future. In one case, the parents went through three sons and a daughter, failing each time to achieve parity. The sale was made to an interested and enthusiastic employee, who did not understand that the easiest part of the business was collecting the cash. Everything else (that brought in that cash) depended upon consistent, reliable service, products, and happy customers. It failed in less than eighteen months, leaving the former owners, now in their mid-70s trying to recoup their losses from their holding the business mortgage.

So what does the transfer/sale of an inter-generational family business take? Here are a few guidelines:

The seller should involve the entire family in future plans to change your lifestyle, long before the event.

Don't be surprised by conflicting emotions, and you will feel them. This was your baby, If you are first generation business owners, it was your identity – you put everything into this huge part of your life.

If the seller wants to continue to work, use your years of accumulated goodwill to promote the business, away from the business.

Transact the sale at arm's length – in a tax economy, this is mandatory.

Get it in writing, all terms, conditions, now and for the future. More misunderstandings and complete family splits take place when this serious event is done on a handshake. Legitimate businesses use contracts, for good reasons.

Run the numbers, again, and again, and again. Build in for all probabilities, best, worst case environments, know exactly how much debt this company can carry. Remember the goose?

Make the business bear the cost, not the older generation, in carrying the financing. Too many strings, too much anxiety about performance, too many opportunities to forgive debt when you may need the money for your own medical care, etc.

When you (the older generation) say you are going to go, then go.

And you, the younger generation, if this is what you have always wanted, be prepared to put the time in to build on the legacy, what ever it takes just like your parents did. You, too, will be successful.