DealBook Column: Never Mind the Résumé. How Hot Is the C.E.O.?

DealBook Column: Newspapers Are Billionaires’ Latest Trophies

DealBook Column: Tech Companies Tread Lightly in Statements on U.S. Spying

Robert Galbraith/ReutersMark Zuckerberg, chief of Facebook, one of several companies that denied a direct role in government spying.

Someone’s not telling the whole truth.

In the wake of the news leak that the National Security Agency is engaged in a wide-ranging surveillance program of Internet users through a system called Prism, the world’s biggest technology companies responded by unilaterally denying any involvement in the government’s spying apparatus.

Mark Zuckerberg, Facebook’s founder and chief executive, declared: “Facebook is not and has never been part of any program to give the U.S. or any other government direct access to our servers,” adding that, “We hadn’t even heard of Prism before yesterday.”

Larry Page, Google’s co-founder and chief executive, went slightly further. “The U.S. government does not have direct access or a ‘back door’ to the information stored in our data centers,” he said. Apple, Microsoft, AOL and Yahoo followed with denials as well.

And yet President Obama and the United States director of national intelligence, James R. Clapper Jr., have publicly confirmed the existence of the Prism system, without providing any details about it.

Of course, the news — as well as the responses — raises doubts about who is telling the truth and about how extensive the spying program really may be.

But perhaps just as important, the episode also raises questions about how publicly traded companies with hundreds of millions of consumers — companies that are regulated by the Securities and Exchange Commission and the Federal Trade Commission — can, and should, react to news when pressed about involvement in confidential government programs.

“They are in a very difficult position,” said Thomas A. Sporkin, a former S.E.C. enforcement official and now a partner at Buckley Sandler. “On one hand they want to project an image of protecting your privacy. On the other, they have statutory obligations to keep government programs confidential” or potentially risk criminal charges if they exposed a secret government program.

Companies could also face a problem if their disclosures were misleading to investors, but only if they materially affected the stock price or had some other adverse effect, lawyers said.

These companies did not just say “no comment.” They flat-out denied involvement. Mr. Sporkin said, “They are probably not being completely forthcoming, but they are probably not lying.” He noted that the statements were highly vetted by legal teams.

While the companies might have wanted to stick in “no comment” mode, a version of peer pressure kicked in, said one chief executive who spoke on the condition of anonymity because of the fragility of the situation. Once one company issued a flat denial, the others felt they had to follow suit, he said.

Indeed, the statements that companies like Facebook and Google made are probably truthful if taken literally. I don’t doubt Mr. Page when he said, “Press reports that suggest that Google is providing open-ended access to our users’ data are false, period.” The title of his statement, which appeared on Google’s corporate blog and was also signed by the company’s chief legal officer, David Drummond, was “What the…?”

But I also don’t doubt another part of his statement that was frequently overlooked: “We provide user data to governments only in accordance with the law.”

In other words, when the government makes a legitimate request — and through Section 702 of the Foreign Intelligence Surveillance Act, which was highlighted by the leak, the government can seek vast troves of information — Google and others comply.

It is possible, for example, that Mr. Page and Mr. Zuckerberg had never been told that the government’s program was called Prism. And it is highly unlikely the government has a password granting access to company servers despite early reports quoting a government document that used the phrase “direct access” and now appears as if it overstated the case.

At the same time, however, companies like Facebook and Google have clearly worked with the government to create systems to transfer vast amounts of private data that is sought by the N.S.A. and other government agencies. The New York Times reported last week, based on people briefed on the matter, that Google and Facebook discussed plans “to build separate, secure portals, like a digital version of the secure physical rooms that have long existed for classified information, in some instances on company servers.”

That is different from the idea that the government has “direct access” to corporate servers, but it still means that the companies are providing the government with enormous amounts of data.

One explanation for the distinction between the corporate denials and the leaked presentation was explained this way in The Washington Post, which along with The Guardian posted several slides from a 41-page presentation about the Internet program: “It is possible that the conflict between the Prism slides and the company spokesmen is the result of imprecision on the part of the N.S.A. author.”

Senior executives I spoke with at many of the technology companies cited in the Prism documents said they routinely provided the government with requested data, in some cases months’ worth of e-mail traffic for a certain address. They have teams of people whose entire job is to work with the government to comply with such requests, which come in daily if not more frequently. Once that information is transferred to the government, an agency can store that data and sort it, integrate it with other data to their heart’s content.

Mr. Sporkin, for example, said that when he was at the S.E.C., the agency would regularly make requests for stock trades and then store that information so it could use it later, sorting it and mixing it with other sources of data.

Most technology companies have a “terms of service” agreement that requires users to accept such a provision before signing up. Buried in the fine print of Facebook’s is this: “We may access, preserve and share your information in response to a legal request (like a search warrant, court order or subpoena) if we have a good faith belief that the law requires us to do so.”

Theoretically, a clever lawyer could make the case that the companies’ public denials have now become part of the terms of service and that customers are relying on them to be true. If those denials turn out to conflict with actions in the future, the companies — again theoretically — could face trouble with their customers and even possibly another arm of the government, like the F.T.C., setting up a true conundrum.

So while the nation’s biggest technology companies may not be a part of systematic large-scale spying program, it is clear that they are legally required to play a significant role in funneling data to the government. That leaves them on a tightrope balancing what they can say to their customers and investors while complying with their obligations to keep the government’s secrets.

DealBook Column: But Wait. Didn’t Yahoo Try a Deal Like This Before?

Mark J. Terrill/Associated PressGeoCities workers after Yahoo bought it in 1999. Some worry the Tumblr deal is similarly poor.

When Yahoo announced its headline-grabbing acquisition, it boasted that the deal gave it access to an “unduplicated” audience of users and that its target was a “popular personal publishing” platform.

“Yahoo will be able to integrate and distribute a powerful set of state-of-the-art editing tools and content published through personal home pages in an array of services,” the company declared.

But Yahoo wasn’t talking about Tumblr. Those quotes came from a news release Yahoo issued in 1999 when it acquired GeoCities, which allowed users to create their own Web pages — not unlike Tumblr — for $3.6 billion in stock. The site was closed in 2009.

As investors and analysts size up Yahoo’s latest $1.1 billion acquisition, it is worth reflecting on the GeoCities deal, which has many similarities. Both companies were money losers when they agreed to be acquired. Tumblr had just $13 million in revenue last year, according to reports.

Both companies had loyal followers that quickly left in droves. According to Matt Mullenweg, the founder of WordPress and a competitor, Tumblr users were moving their posts over to WordPress at a rate of 72,000 an hour amid speculation of an impending deal this weekend. (Usually, he said, Tumblr users migrated 400 to 600 posts an hour). Still, for perspective, Tumblr users generate tens of millions of posts a day.

And GeoCities and Tumblr had at one point been averse to accepting advertising. Tumblr’s 26-year-old chief executive (and now multimillionaire), David Karp, said three years ago, “We’re pretty opposed to advertising,” adding that “It turns our stomach.”

The lesson of GeoCities raises this question about Tumblr: How can a company with zero profits (actually, multimillion-dollar losses) and just $13 million in revenue be worth $1.1 billion?

Inside Yahoo, officials dismiss the comparison to GeoCities. Instead, they compare the Tumblr deal to Google’s purchase of YouTube — that is, Yahoo’s management believes that Tumblr is one of a rare few transformative sites on the Internet. Google paid $1.6 billion for YouTube when it too made no money. At the time of that deal, it seemed heretical. Now, it seems genius.

To Yahoo, Tumblr is the equivalent of beachfront property. With more than 100 million user-generated blogs on Tumblr, there is no question that it brings Yahoo a younger audience. It adds a sense of hipness to a company that had lost its sense of cool.

According to Marissa Mayer, Yahoo’s chief executive, who drove this deal, Tumblr brings Yahoo a possible growth engine for the future.

But that’s a big if. It requires Ms. Mayer’s team to execute brilliantly and online users to continue to want to establish ways to communicate outside of places like Facebook and Twitter.

And then there is the pesky issue of selling ads on Tumblr’s pages without upsetting the site’s finicky users. (One user began a petition to block the deal.)

“It is difficult to justify the premium acquisition price for Tumblr given its low levels of revenue,” wrote Anthony DiClemente of Barclays Capital in a note to investors. “In addition, we believe Yahoo needs to be careful about the manner in which it monetizes Tumblr, as a significant ad load and the perception of a large corporate owner could potentially alienate Tumblr’s core user base. Though we believe Tumblr’s model does have switching costs for users, we do not view its actual barriers to entry as particularly high.”

If you want to do the math on what it would take for Yahoo to justify the price tag, Brian Pitz, an analyst at Jefferies, has sketched it out. By his count, Yahoo will need to figure out a way to make $127 million a year in profit from Tumblr, meaning the site would have to bring in an additional $950 million annually in advertising revenue.

That’s a big challenge, especially considering that Ms. Mayer pledged that while she planned to add more ads to Tumblr, she would do so mostly on the site’s “dashboard” or newsfeed.

“We would like to look at them and understand how we could introduce ads — in a very light ad load — where the impact is really created, because the ads really fit the users’ expectations and follow the form and function of the dashboard,” Ms. Mayer said.

She said she might add advertising to user pages, but only with the permission of the blogger. That means a lot of Web pages will not be monetized.

And there is the issue of porn. Yes, porn. At least some of Tumblr’s users post images that are not exactly “work safe.” Indeed, Tumblr’s own terms of service allows for such content. Such content could make Tumblr a challenging environment for advertisers.

Tumblr’s users also regularly post copyrighted images and other content Yahoo will have to find a way to police. When Tumblr was just an upstart, content owners were unlikely to pursue claims against the company, but now that it might be owned by a big public corporation, you can bet that copyright owners, some of whom compete with Yahoo, will be contacting their lawyers.

Given all of that, you might expect me to say that Yahoo should have never proposed acquiring Tumblr. But I won’t.

It may actually turn out to be the right bet. The key is recognizing that it is a shoot-the-moon gamble. It might work out. It might not.

And even if it does not work out, analysts note that Yahoo can afford to experiment given the billions of dollars it has in cash.

As Jordan Rohan, an analyst at Stifel Nicolaus, wrote: “Even a squandering of $1.1 billion in cash, however unlikely that might seem to Yahoo management, would only move the sum-of-parts slightly.”

This post has been revised to reflect the following correction:

Correction: May 22, 2013

The DealBook column on Tuesday, about the similarities between Yahoo’s deal for Tumblr and its deal more than a decade ago for GeoCities, misidentified an analyst from Barclays Capital who commented on the Tumblr transaction in a note to investors. He is Anthony DiClemente — not Doug Anmuth, who is an analyst for JPMorgan Chase.

DealBook Column: Suggestions for an Apple Shopping List

David Paul Morris/Bloomberg NewsTim Cook, left, chief of Apple, and Paul Sagan, chief of Akamai Technologies, at the Sun Valley conference.

Question: What would you do if you had $117 billion?

That’s the challenge facing Tim Cook, Apple’s chief, whose company’s cash hoard keeps growing — by about $1 billion a week.

He could hold onto it. He could increase Apple’s dividend, which he instituted this year for the first time.

Or he could spend it.

Just last week, Mr. Cook acquired AuthenTec, a mobile security company, for $356 million in cash — a price equal to pocket lint for a company with the war chest the size of Apple’s.

The real question is whether Mr. Cook would ever spend Apple’s money on an “elephant” — Wall Street parlance for a huge deal.

Apple denizens often say that the company is not interested in deal making. It has, after all, invented some of today’s most successful consumer products. But that view misunderstands Apple’s history: some of its most important innovations were not invented within Apple; they were purchased from other companies.

For example, the touch-sensitive gesture technology that made the iPhone and iPad possible was invented and patented by FingerWorks, which Apple acquired in 2005. Siri? Apple bought it in 2010. Even Apple’s current Macintosh operating system was an acquisition of sorts. It is built on the back of NeXT, acquired from Steve Jobs (they got him to return as part of the deal, too) in 1996. (Pixar, Mr. Jobs’s other big success, was an acquisition as well. He bought the company from George Lucas as part of a spinoff from Lucasfilm in 1986.)

A year before Mr. Jobs died, he strongly hinted that Apple would consider a big deal. “We strongly believe that one or more very strategic opportunities may come along, that we are in a unique position to take advantage of because of our strong cash position,” Mr. Jobs said in a call with analysts in 2010.

Having all that money can be daunting, so to help Mr. Cook, here is a potential shopping list — some must-buys and some pie-in-the-sky targets — that he may want to consider:

NUANCE This is the one no-brainer on the list. Nuance, based in Burlington, Mass., provides much of the speech recognition technology behind Apple’s Siri and dictation functions. Right now, Apple has merely licensed it and integrated it into both its mobile devices like iPhones and iPads as well as its new Macintosh operating system. Most users think it is Apple technology, but those services wouldn’t work without Nuance.

It should go without saying, but the importance of speech recognition is only going to increase in the future. Nuance has more patents for it and has developed the technology further than just about any firm in the world. At some point, Nuance will be able to hold Apple for ransom. Google and Microsoft are steadily building their own speech recognition technologies and they are catching up quickly. Nuance’s market value is $6.3 billion. Even if Apple paid twice as much, it would be a worthwhile investment.

TWITTER AND PATH Consider this a one-two punch. Apple should buy the social media companies Twitter and Path. Twitter is well known. The 140-character Twitterverse now has more than 140 million active monthly users. It is one of the few, if only, independent social media properties that could allow Apple to build its own social media platform to truly compete against the likes of Facebook and Google.

Twitter’s price tag is just north of $10 billion, and as my colleagues Evelyn M. Rusli and Nick Bilton reported in The New York Times last week, the idea has certainly crossed the minds of Apple executives.

Path is less familiar, but it would be an integral ingredient for Apple’s push into social media. Path is a fast-growing social media company that works on mobile devices only. It has cracked the code on making the mobile experience of sharing with friends enjoyable. Path would probably cost $250 million to $1 billion. If Apple were to stir together Twitter, Path and its own Photo Stream service — and leveraged all the data it has collected about its users over the years (while mindful of privacy issues) — the company would have quite a product that would keep consumers hooked.

RESEARCH IN MOTION Yes, this one may be a head-scratcher, considering that the iPhone seems to have eaten RIM’s BlackBerry for breakfast — and lunch. But with a marke value of $3.7 billion it is a relative bargain and could be had for four weeks’ worth of Apple’s spare cash).

Such a deal would instantly put Apple into the enterprise market, giving it access to corporate and government customers that require RIM’s highly secure servers. Apple could build access into RIM’s network directly into future iPhones and maybe even create an iPhone with BlackBerry’s famous keyboard, which for many of us would create the ultimate smartphone.

RIM’s relationships with corporate and government customers could be leveraged to sell other products like computers and iPads. RIM also owns QNX, a software that is being used in its next-generation BlackBerry devices. More important for Apple, QNX is used as an in-dashboard operating system, and it is already in 20 million cars, like Chryslers and Porsches.

Finally, there are RIM’s patents, said to be worth $1 billion to $4 billion alone, a virtual treasure trove for a company that is locked in brutal patent wars with rivals. Google paid $12.5 billion for Motorola Mobility last year, in part, to secure the company’s patent portfolio.

SQUARE Everyone is talking about the mobile wallet. Square, started by the Twitter co-founder Jack Dorsey, has created a unique new electronic payment system though iPhones and iPads. The next time you go to a coffee shop, there is a chance you can pay with your iPhone simply by saying your name when you get to the cash register.

Square’s value has crept up to more than $3 billion, which is high for a company that is still losing money. But if Apple could integrate Square into iTunes — which has over 400 million active credit cards on file from around the world — it could become a sensation overnight, pushing out rivals like VeriFone and PayPal.

SPRINT Yes, the phone company. This might seem the most out-there idea. But it solves many of Apple’s biggest problems.

Such a deal would give Apple its own wireless network, which it could upgrade to become the ultimate high-speed wireless carrier in the country. It could eventually use the network to bypass the cable operators to deliver content directly to the home on multiple devices, including the product that everyone speculates is on its way: a TV device.

With a stock market value of $13.5 billion, Sprint can be purchased for a song. Apple could easily spend four times more than that — say, $50 billion — to build out the Sprint network and turn it into a showcase for the next generation mobile technology. Apple could still offer its devices on other carriers, but its premium product would exist on its own network.

Think about it: Apple service, Apple Stores and simple Apple pricing. That would revolutionize the business. And such an investment would force the other carriers to step up their game, which would only help Apple. Most compelling is the possibility of Apple owning the last mile into everyone’s home (wirelessly) and be able to offer televised content. (I had considered Netflix as a suitable acquisition target, but if Apple had its own telephone company, it could negotiate directly with content providers on a level playing field with cable and satellite operators.)

The total cost for this grocery list, takeover premiums and additional investments included, is about $97 billion, give or take a couple billion. (Let’s put aside the thorny issue of how Apple can use its cash, much of which is abroad, without being taxed). That would leave Mr. Cook with $20 billion in the bank for walking-around money.

DealBook Column: Suggestions for an Apple Shopping List

David Paul Morris/Bloomberg NewsTim Cook, left, chief of Apple, and Paul Sagan, chief of Akamai Technologies, at the Sun Valley conference.

Question: What would you do if you had $117 billion?

That’s the challenge facing Tim Cook, Apple’s chief, whose company’s cash hoard keeps growing — by about $1 billion a week.

He could hold onto it. He could increase Apple’s dividend, which he instituted this year for the first time.

Or he could spend it.

Just last week, Mr. Cook acquired AuthenTec, a mobile security company, for $356 million in cash — a price equal to pocket lint for a company with the war chest the size of Apple’s.

The real question is whether Mr. Cook would ever spend Apple’s money on an “elephant” — Wall Street parlance for a huge deal.

Apple denizens often say that the company is not interested in deal making. It has, after all, invented some of today’s most successful consumer products. But that view misunderstands Apple’s history: some of its most important innovations were not invented within Apple; they were purchased from other companies.

For example, the touch-sensitive gesture technology that made the iPhone and iPad possible was invented and patented by FingerWorks, which Apple acquired in 2005. Siri? Apple bought it in 2010. Even Apple’s current Macintosh operating system was an acquisition of sorts. It is built on the back of NeXT, acquired from Steve Jobs (they got him to return as part of the deal, too) in 1996. (Pixar, Mr. Jobs’s other big success, was an acquisition as well. He bought the company from George Lucas as part of a spinoff from Lucasfilm in 1986.)

A year before Mr. Jobs died, he strongly hinted that Apple would consider a big deal. “We strongly believe that one or more very strategic opportunities may come along, that we are in a unique position to take advantage of because of our strong cash position,” Mr. Jobs said in a call with analysts in 2010.

Having all that money can be daunting, so to help Mr. Cook, here is a potential shopping list — some must-buys and some pie-in-the-sky targets — that he may want to consider:

NUANCE This is the one no-brainer on the list. Nuance, based in Burlington, Mass., provides much of the speech recognition technology behind Apple’s Siri and dictation functions. Right now, Apple has merely licensed it and integrated it into both its mobile devices like iPhones and iPads as well as its new Macintosh operating system. Most users think it is Apple technology, but those services wouldn’t work without Nuance.

It should go without saying, but the importance of speech recognition is only going to increase in the future. Nuance has more patents for it and has developed the technology further than just about any firm in the world. At some point, Nuance will be able to hold Apple for ransom. Google and Microsoft are steadily building their own speech recognition technologies and they are catching up quickly. Nuance’s market value is $6.3 billion. Even if Apple paid twice as much, it would be a worthwhile investment.

TWITTER AND PATH Consider this a one-two punch. Apple should buy the social media companies Twitter and Path. Twitter is well known. The 140-character Twitterverse now has more than 140 million active monthly users. It is one of the few, if only, independent social media properties that could allow Apple to build its own social media platform to truly compete against the likes of Facebook and Google.

Twitter’s price tag is just north of $10 billion, and as my colleagues Evelyn M. Rusli and Nick Bilton reported in The New York Times last week, the idea has certainly crossed the minds of Apple executives.

Path is less familiar, but it would be an integral ingredient for Apple’s push into social media. Path is a fast-growing social media company that works on mobile devices only. It has cracked the code on making the mobile experience of sharing with friends enjoyable. Path would probably cost $250 million to $1 billion. If Apple were to stir together Twitter, Path and its own Photo Stream service — and leveraged all the data it has collected about its users over the years (while mindful of privacy issues) — the company would have quite a product that would keep consumers hooked.

RESEARCH IN MOTION Yes, this one may be a head-scratcher, considering that the iPhone seems to have eaten RIM’s BlackBerry for breakfast — and lunch. But with a marke value of $3.7 billion it is a relative bargain and could be had for four weeks’ worth of Apple’s spare cash).

Such a deal would instantly put Apple into the enterprise market, giving it access to corporate and government customers that require RIM’s highly secure servers. Apple could build access into RIM’s network directly into future iPhones and maybe even create an iPhone with BlackBerry’s famous keyboard, which for many of us would create the ultimate smartphone.

RIM’s relationships with corporate and government customers could be leveraged to sell other products like computers and iPads. RIM also owns QNX, a software that is being used in its next-generation BlackBerry devices. More important for Apple, QNX is used as an in-dashboard operating system, and it is already in 20 million cars, like Chryslers and Porsches.

Finally, there are RIM’s patents, said to be worth $1 billion to $4 billion alone, a virtual treasure trove for a company that is locked in brutal patent wars with rivals. Google paid $12.5 billion for Motorola Mobility last year, in part, to secure the company’s patent portfolio.

SQUARE Everyone is talking about the mobile wallet. Square, started by the Twitter co-founder Jack Dorsey, has created a unique new electronic payment system though iPhones and iPads. The next time you go to a coffee shop, there is a chance you can pay with your iPhone simply by saying your name when you get to the cash register.

Square’s value has crept up to more than $3 billion, which is high for a company that is still losing money. But if Apple could integrate Square into iTunes — which has over 400 million active credit cards on file from around the world — it could become a sensation overnight, pushing out rivals like VeriFone and PayPal.

SPRINT Yes, the phone company. This might seem the most out-there idea. But it solves many of Apple’s biggest problems.

Such a deal would give Apple its own wireless network, which it could upgrade to become the ultimate high-speed wireless carrier in the country. It could eventually use the network to bypass the cable operators to deliver content directly to the home on multiple devices, including the product that everyone speculates is on its way: a TV device.

With a stock market value of $13.5 billion, Sprint can be purchased for a song. Apple could easily spend four times more than that — say, $50 billion — to build out the Sprint network and turn it into a showcase for the next generation mobile technology. Apple could still offer its devices on other carriers, but its premium product would exist on its own network.

Think about it: Apple service, Apple Stores and simple Apple pricing. That would revolutionize the business. And such an investment would force the other carriers to step up their game, which would only help Apple. Most compelling is the possibility of Apple owning the last mile into everyone’s home (wirelessly) and be able to offer televised content. (I had considered Netflix as a suitable acquisition target, but if Apple had its own telephone company, it could negotiate directly with content providers on a level playing field with cable and satellite operators.)

The total cost for this grocery list, takeover premiums and additional investments included, is about $97 billion, give or take a couple billion. (Let’s put aside the thorny issue of how Apple can use its cash, much of which is abroad, without being taxed). That would leave Mr. Cook with $20 billion in the bank for walking-around money.

DealBook Column: Taking a Risk, and Hoping That Lightning Strikes Twice

Simon Dawson/Bloomberg NewsSean Parker, 32, was a co-founder of Napster.

Sean Parker, the 32-year-old billionaire and former president of Facebook — played by Justin Timberlake in “The Social Network” — was sitting on the top floor of his town house in the West Village of Manhattan last month, lamenting that too few entrepreneurs continue taking big risks after their first great success.

“Every good entrepreneur I know ends up in the wasteland of being a venture capitalist. It’s really frustrating,” he said.

Mr. Parker was sitting, or more accurately, slouching, on a couch next to his best friend and business partner, Shawn Fanning. Together, they founded Napster in 1999, the online music service that upended the entire industry before closing and filing for bankruptcy after losing a court case over piracy.

“How can you as an entrepreneur that’s had success, has a reputation, ever build the courage to go and do something again?” he asked, almost rhetorically. “Most entrepreneurs don’t remain entrepreneurs. It’s just too psychologically draining to have to constantly start over.”

More than a decade later, however, Sean and Shawn are at it again. The two recently started a video chat service called Airtime. (Think Skype, mixed with Facebook and a twist of Chatroulette.)

Mr. Parker and Mr. Fanning are the exceptions to the successful-entrepreneurs-still-working theory. Sure, there are a handful of serial entrepreneurs out there in Silicon Valley: Jack Dorsey started Twitter and Square, for example, and Elon Musk, who was behind PayPal, now runs SpaceX and Tesla.

But the career trajectory of many tremendously successful entrepreneurs in Silicon Valley often looks like a rocket ship that stops in midair. Less charitably, Mr. Parker suggests some could be called one-hit wonders.

“The list of people who have started from scratch over and over and succeeded systematically over a long period of time is incredibly short,” he said. “The only person I can think of off the cuff is Jobs who had Apple, Next, Pixar, continued doing Pixar and Next and then Apple again, which is really a different company.”

He said that the tendency of great entrepreneurs was either to become merely an operator of one company or, like Sumner Redstone, move into an investor-ownership role.

The Silicon Valley version becomes a venture capitalist. For example, Peter Thiel, who co-founded PayPal, has gone on to be a successful venture capitalist through his firm Founders Fund, investing in other companies’ businesses, like Facebook and Spotify. But Mr. Thiel hasn’t endeavored to start a new company himself. (He did start a hedge fund, but that’s still investing.) He happens to be in business with Mr. Parker, who is a partner in the fund, which also invested in his Airtime.

Marc Andreessen, a longtime star of Silicon Valley, co-founded Netscape in 1994. He started two companies after that: Loudcloud and Ning. Both had modest success, but neither was comparable to Netscape. Mr. Andreessen became one of those venture capitalists Mr. Parker dreads, but with an extremely successful track record of having invested in some of the most promising technology companies, including Facebook, Groupon, Twitter, Zynga, Pinterest and Instagram (which was sold this year to Facebook for $1 billion).

Perhaps surprisingly, Mr. Andreessen said of Mr. Parker’s theory: “I sort of agree with him.” In an interview, he said many “former entrepreneurs crossed over to be V.C.’s and it hasn’t worked out well.” He added, “You don’t want to be Michael Jordan playing baseball.”

Mr. Andreessen said he differentiated his decision to pursue investing from that of other entrepreneurs-turned-investors, because he approached it as an entrepreneurial effort to “rethink the model of venture capital.” He has sought to reimagine the way a venture capital firm works from top to bottom, and so far, it appears to working quite spectacularly.

Still, to Mr. Parker, most entrepreneurs who seek out investments do so as “a total cop-out.” He explained his thinking: “You have a whole portfolio, you only focus on your successes, you ignore your failures and you get to continue looking like a player, but you’re ultimately not in control of anything.”

He continued: “Everything is probabilistic, nothing is deterministic, so you never have that satisfaction of knowing that you’re in control of an outcome. So you spend all of your time managing your reputation, managing your relationships and you spend almost no time thinking creatively or doing the things that an entrepreneur is good at doing.”

If it sounds as if Mr. Parker is talking only about others, he’s not. He’s also talking about himself.

After stepping down from Facebook in 2005, he joined Mr. Thiel’s Founders Fund and for several years worked on making investments, including in Spotify and Votizen.

He also worked on Causes, a site to raise money and awareness for issues and nonprofits. That venture only muddled along, and he said he did not commit to it wholeheartedly enough.

He said the biggest challenge for any new start-up by a previously successful entrepreneur was focusing too much “on downside protection, which is just assuming failure from the outset.” Being worried about failure and its effect on one’s reputation, he said, is “very dangerous.”

He said he was reluctant to start a new company like Airtime until just recently.

“The expectation thing definitely weighs on me. There’s a sort of fear of launching something and failing,” he said. “I had to decide I am going to try to go the road less traveled and just be an entrepreneur that’s willing to go back and start things from scratch.”

DealBook Column: Taking a Risk, and Hoping That Lightning Strikes Twice

Simon Dawson/Bloomberg NewsSean Parker, 32, was a co-founder of Napster.

Sean Parker, the 32-year-old billionaire and former president of Facebook — played by Justin Timberlake in “The Social Network” — was sitting on the top floor of his town house in the West Village of Manhattan last month, lamenting that too few entrepreneurs continue taking big risks after their first great success.

“Every good entrepreneur I know ends up in the wasteland of being a venture capitalist. It’s really frustrating,” he said.

Mr. Parker was sitting, or more accurately, slouching, on a couch next to his best friend and business partner, Shawn Fanning. Together, they founded Napster in 1999, the online music service that upended the entire industry before closing and filing for bankruptcy after losing a court case over piracy.

“How can you as an entrepreneur that’s had success, has a reputation, ever build the courage to go and do something again?” he asked, almost rhetorically. “Most entrepreneurs don’t remain entrepreneurs. It’s just too psychologically draining to have to constantly start over.”

More than a decade later, however, Sean and Shawn are at it again. The two recently started a video chat service called Airtime. (Think Skype, mixed with Facebook and a twist of Chatroulette.)

Mr. Parker and Mr. Fanning are the exceptions to the successful-entrepreneurs-still-working theory. Sure, there are a handful of serial entrepreneurs out there in Silicon Valley: Jack Dorsey started Twitter and Square, for example, and Elon Musk, who was behind PayPal, now runs SpaceX and Tesla.

But the career trajectory of many tremendously successful entrepreneurs in Silicon Valley often looks like a rocket ship that stops in midair. Less charitably, Mr. Parker suggests some could be called one-hit wonders.

“The list of people who have started from scratch over and over and succeeded systematically over a long period of time is incredibly short,” he said. “The only person I can think of off the cuff is Jobs who had Apple, Next, Pixar, continued doing Pixar and Next and then Apple again, which is really a different company.”

He said that the tendency of great entrepreneurs was either to become merely an operator of one company or, like Sumner Redstone, move into an investor-ownership role.

The Silicon Valley version becomes a venture capitalist. For example, Peter Thiel, who co-founded PayPal, has gone on to be a successful venture capitalist through his firm Founders Fund, investing in other companies’ businesses, like Facebook and Spotify. But Mr. Thiel hasn’t endeavored to start a new company himself. (He did start a hedge fund, but that’s still investing.) He happens to be in business with Mr. Parker, who is a partner in the fund, which also invested in his Airtime.

Marc Andreessen, a longtime star of Silicon Valley, co-founded Netscape in 1994. He started two companies after that: Loudcloud and Ning. Both had modest success, but neither was comparable to Netscape. Mr. Andreessen became one of those venture capitalists Mr. Parker dreads, but with an extremely successful track record of having invested in some of the most promising technology companies, including Facebook, Groupon, Twitter, Zynga, Pinterest and Instagram (which was sold this year to Facebook for $1 billion).

Perhaps surprisingly, Mr. Andreessen said of Mr. Parker’s theory: “I sort of agree with him.” In an interview, he said many “former entrepreneurs crossed over to be V.C.’s and it hasn’t worked out well.” He added, “You don’t want to be Michael Jordan playing baseball.”

Mr. Andreessen said he differentiated his decision to pursue investing from that of other entrepreneurs-turned-investors, because he approached it as an entrepreneurial effort to “rethink the model of venture capital.” He has sought to reimagine the way a venture capital firm works from top to bottom, and so far, it appears to working quite spectacularly.

Still, to Mr. Parker, most entrepreneurs who seek out investments do so as “a total cop-out.” He explained his thinking: “You have a whole portfolio, you only focus on your successes, you ignore your failures and you get to continue looking like a player, but you’re ultimately not in control of anything.”

He continued: “Everything is probabilistic, nothing is deterministic, so you never have that satisfaction of knowing that you’re in control of an outcome. So you spend all of your time managing your reputation, managing your relationships and you spend almost no time thinking creatively or doing the things that an entrepreneur is good at doing.”

If it sounds as if Mr. Parker is talking only about others, he’s not. He’s also talking about himself.

After stepping down from Facebook in 2005, he joined Mr. Thiel’s Founders Fund and for several years worked on making investments, including in Spotify and Votizen.

He also worked on Causes, a site to raise money and awareness for issues and nonprofits. That venture only muddled along, and he said he did not commit to it wholeheartedly enough.

He said the biggest challenge for any new start-up by a previously successful entrepreneur was focusing too much “on downside protection, which is just assuming failure from the outset.” Being worried about failure and its effect on one’s reputation, he said, is “very dangerous.”

He said he was reluctant to start a new company like Airtime until just recently.

“The expectation thing definitely weighs on me. There’s a sort of fear of launching something and failing,” he said. “I had to decide I am going to try to go the road less traveled and just be an entrepreneur that’s willing to go back and start things from scratch.”