I sat in on a fascinating talk by former Wall Street Journal reporter Paul Carroll this week. Carroll is the co-author (along with Chunka Mui) of Billion Dollar Lessons about some of the most colossal business failures and what can be learned from them. The event was sponsored by the Churchill Club.

Carroll recounted some of the familiar ones, though with additional insights as to the reasons behind them. He noted, for example, companies that aren’t technology-oriented, can get enamored with the latest disruptive technology with dire consequences. Exhibit A: Federal Express’ disastrous Zapmail rollout in the mid-1980s.

“Companies make the mistake of assuming their competition will remain static,” said Carroll. Zapmail made sense at the time because fax machines weren’t very good and the service offered a way for companies to get important documents delivered the same day they were sent. Problem was, fax machines got better and less expensive, leaving Federal Express with a half a billion dollar write-off a few years after launch.

And then technology companies themselves get carried away. The Iridium satellite project had a competitive edge when it was first hatched in 1985, but $5 billion later it failed and the consortium behind it was forced to sell its assets for $25 million.

The Emperor has no clothes

Carroll has no problem with big ideas and thinking different, but he said companies often make decisions for the wrong reason. Worse, it’s not companies but the CEO making the mistakes everyone else can see but are too afraid to make waves.

“There’s a desire to please the CEO,” he said. “But successful organizations tolerate a high level of disagreement, even encourage it,” he said. Carroll covered IBM for years and recalls its legendary CEO Tom Watson “loved a good fight.” He suggests companies would even be wise to designate a devil’s advocate to make sure new ideas can withstand critical evaluation.

But what about Apple?

So in the spirit of Carroll’s supposition, I waited for the Q&A portion to disagree. I said it all sounded good in theory, but how did he explain the success of a company like Apple, which seems to run counter to a culture of challenging ideas — unless the challenge comes from CEO Steve Jobs.

Carroll conceded Jobs is the exception that proves the rule. “Apple is an anomaly. Steve Jobs is just remarkable, he’s Mozart,” said Carroll. Going by his knowledge of failed mergers and acquisitions, Carroll recalled Jobs convinced Apple to buy his company NeXT as part of his return to Apple. “At the time, I thought it was a mistake,” said Carroll.

You can read excerpts from Billion Dollar Lessons and find information on company failures at a related Web site.

Carroll joked that with the way some of the big company failures are going now he may have to re-title the next edition to Trillion Dollar Lessons.

Yahoo is claiming victory, or at least a lead, in the race to improve the privacy of user’s comings and going on the Web. Starting next month, Yahoo said it will anonymize user log data within 90 days. Up till now, Yahoo kept such data up to 13 months. Exceptions include “fraud, security and legal obligations” that presumably would compel Yahoo to keep such information longer. But in general, Yahoo will now have a much shorter vault of information on its 500 million users worldwide .

Yahoo said it will also expand the policy to apply not only to search log data but also page views, page clicks, ad views and ad clicks.

You may recall Google has been steadily scaling back the length of time it retains user data which used to be years. In September, Google announced it was cutting the retention time in half, from 18 months down to 9 months. After that period, the server logs are “anonymized” so it becomes impossible to trace an IP address back to an individual.

Google and other Web companies, maintain that analyzing the server logs with full IP addresses collected over an extended period of time helps them combat fraud, spam and other Internet threats.

“This policy represents Yahoo!’s assessment of the minimum amount of time we need to retain data in order to respond to the needs of our business while deepening our trusted relationship with users,” said Anne Toth, Yahoo’s vice president of policy and head of privacy.

Ask and you shall be erased

The most direct and perhaps most innovative solution to this aspect of data privacy is from Ask.com which unveiled its “AskEraser” button a year ago this month.

Clicking the AskEraser button in the top right corner of the page will automatically delete related cookie information from Ask.com’s servers, including user and session ID’s, IP addresses and search text.

There’s not much doubt, health concerns aside, that Apple CEO Steve Jobs will give the keynote early next month at Macworld Expo in San Francisco.

But pity the show producers. You’d have to think they would love the chance to promote Macworld Expo months in advance as featuring a keynote by the best known CEO in tech with a penchant for taking the wraps off brand new products and technology. No such luck. For years, Steve J. has consistently left them waiting till a short time before the show, to confirm his attendance.

“We should have an announcement next week,” Charlotte McCormack, public relations manager for IDG Expo told me. “People think because we’re Macworld Expo we know more, but we don’t have any insight into Apple’s plans and can’t comment.”

It’s not like the show has much choice; Macworld without a Steve Jobs keynote is just another tradeshow. In earlier years someone from IDG used to make some welcoming remarks before introducing Jobs. Now it’s strictly an Apple event with Steve firmly in control from the start.

“Even though it’s expected Jobs will be there, it’s never a given. It’s part of the drama,” Gartner analyst and veteran Apple watcher Mike McGuire told me.

Is it possible Jobs won’t show? A former Apple marketing consultant who asked not to be identified, told me “Nothing Steve does or doesn’t do would surprise me. Apple is very careful to connect Steve’s voice to news of substance and they wouldn’t put him up in front of an audience if they didn’t have that going for them.”

Apple brought out new versions of its MacBook notebook line as recently as October and no new iPhone announcements are expected, but Jobs could preview “Snow Leopard” the latest version of the Mac operating system due out later in 2009. There’s also the chance of new desktop Macs.

My trip to Boston for Thanksgiving started bad and got worse.

Boarded the plane in plenty of time, but as we taxied down the runway at SFO, the smells began. Oil was burning somewhere and everyone had to deplane. The plane rode off to an EPA-designated area to burn-off excess oil that had spilled. When it returned (several hours later!), we re-boarded and started our take off only to have the smell return and have to deplane again.

Luckily, the third time was a charm; we boarded a different plane without incident.

Boston was great. (Nice job on the turkey Clare!). The return trip was on time. During a long stopover I strolled through the Dallas/Ft. Worth airport and noticed two large massage chairs for rent. Cost? $1 for the first three minutes and up from there. Two people were happily being auto-rubbed. I asked one how it was. “Not bad,” she said. “Definitely worth trying for a buck.”

I walked around a bit more and found a “free” Internet terminal. Great idea. For once, I didn’t bring my HP notebook with me for the trip (highly recommended if you truly want to take a vacation from work), so it was a good time to get caught up on my Web surfing.

The free Internet came with a few hitches though. First off, you have to click on some ad offers to surf freely. This was pretty painless though as only a few of the ads required any payment or commitment other than a few click-throughs. But you only get ten free minutes. Also, there’s a little count-down timer in the corner of the screen, silently imploring you to make every click count even as other would-be surfers stare daggers at you waiting their turn.

The other, literal, pain point, was the backless stoop of a chair in front of the terminal. Five minutes of leaning forward had my balky back pining for one of the robo-massage chairs and even springing for the $5 extended play.

No such luck. When I got there, two new people were snoozing on the comfy chairs without paying a dime. Smart move, because even without paying for the robot fingers, those chairs were way more comfortable than the molded plastic that passes for furniture at the airport.

Here’s an idea. How about combining the Internet terminal with a massage chair? I might even spring for a ten spot instead of logging off with leg cramps.

Investment banker Paul Deninger had a message for the well-heeled group of BlackBerry-toting venture capitalists at the posh Ritz Carlton hotel in Half Moon Bay, CA this week — lose the bottled water.

“People are surprised when I tell them bottled water is more than $5 billion a year in the U.S.,” said Deninger, vice chairman at Jefferies & Co. “It’s actually $30 billion a year!”

Sounds like the kind of profitable racket any of the suits in attendance at the AlwaysOn Venture Summit this week would appreciate. But to Deninger profit isn’t the issue, the environment is.

If bottled water were eliminated, along with the manufacturing and transportation costs that make it possible, Deninger estimates it would be the equivalent of taking a million cars off the road. He also notes “the amount of water used to create a bottle of water is three times what the bottle can contain.”

Deninger is a firm believer in the promise of clean tech, but thinks consumers and industry have to wake up to some harsh realities before there’s a commitment to change.

“We’re completely out of touch about energy utilization,” he said. “Over half the energy we generate is never used. Fifty-five percent is lost to heat and transmission.”

And although there’s a general perception that Europe is ahead of the U.S. in clean tech, Deninger said in related venture capital spending the U.S. is outspending Europe seven to one. “Europe is ahead in government regulation like they always are,” he quipped.