Meg Whitman, president and CEO of online retailer eBay (NASDAQ:EBAY), has had a remarkable career. Aside from pioneering one of the greatest business stories of all time and being a self-made billionaire, the Harvard grad is only one of seven women to be ranked consistently on Time magazine's World's Most Influential People list.

That's why I was shocked to discover the reasons behind the failed attempt to purchase the online telephone company Skype. Last week, eBay announced that it would write off more than $1.4 billion from the acquisition of Skype, more than half of the $2.6 billion it paid for the company two years ago.

Now, we all make mistakes ... some will cost us money. Making mistakes can be the best way to learn how not to do something again. As Mark Twain noted, "A man who picks up a cat by the tail learns something he can learn in no other way."

A recent story in The Economist presented three lessons Whitman learned that seemed to justify the Skype purchase. She may want to apply those lessons to future purchases.

Lesson No. 1: Focus on the big picture
An aspiring young MBA graduate in 1979, Whitman started her career at Procter & Gamble (NYSE:PG), where she now sits on the board of directors. Her first assignment: Deciding whether the hole in shampoo bottletops should be one-half or three-eighths of an inch wide. Whitman poured her heart into the tedious project, and her dedication was an admirable quality indeed.  

Fast-forward 26 years to negotiations for the Skype acquisition. Whitman undoubtedly brought the same meticulous attention to detail she learned at Procter & Gamble.

Niklas Zennstrom, Skype's co-founder, had been quoted as saying, "We want to make as little money as possible per user," hinting that the hoopla surrounding Skype was focused on bringing free service to its users, not making money for shareholders. Just as the shampoo was unquestionably more important to the consumer than its container's bottletop, the "non-profit" attitude of Skype's management proved more important to eBay's shareholders than Skype's breakthrough technology.

Her lesson? Small details are important, yes, but investors need to focus on the big factors.

Lesson No. 2: Remember Warren
In 2002, eBay had its eye on online-payment processor PayPal. Before pulling the trigger, eBay decided to wait and continue to negotiate with the company. As it waited, the price continued to climb as other bidders entered the market. Determined not to let this happen again, Whitman decided to highball Skype's sellers and pre-emptively outbid any competition.

Her lesson? Violation of Warren Buffett's cardinal rules:

  • Rule No. 1: Never lose money.
  • Rule No. 2: Don't forget rule No. 1.

In investing, the price you pay determines everything. Even the best company in the world can become a money-losing venture once its price exceeds intrinsic value. Conversely, even crummy, poorly managed companies become good investments if the price falls below its value. Warren Buffett, known for sticking to well-managed companies with durable competitive advantages, went against the grain and made a good deal of money investing in distressed Level 3 Communications (NASDAQ:LVLT) bonds and struggling mortgage company Laser Mortgage in recent years.

By intentionally overpaying, eBay eroded future potential shareholders could have received had Skype succeeded from the get-go. Fools, take heed: There is nothing glamorous about overpaying ... especially for companies that don't even plan on making money.

Lesson No. 3: Know when wanting is better than having
Whitman was determined not to be left out of the game. In her view, the cost of an online retailer not buying a telephone company far succeeded the cost of failure. (Like you, I am puzzled by this.)

Her lesson? Just as Warren Buffett has succinctly stated: "In investments, there's no such thing as a called strike. You can stand there at the plate, and the pitcher can throw a ball right down the middle. The only way you can have a strike is to swing and miss."

In business and investing, it's important to check your ego at the door and not fall into the "but everyone else has one" syndrome. Wait for the perfect pitch -- the right company at the right price -- before taking a swing.

Foolish takeaway
These lessons can have as much of an impact on Foolish investors as they did on eBay's high-profile CEO. Whether you're structuring multibillion-dollar deals or just starting with your first investment account, always remember to focus on the most important details; demand an attractive price; and wait for the perfect pitch.

And forget the shampoo bottle.

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This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.