March 23, 2023

Tool Kit: Digital Tools to Help Curb Online Eavesdropping

SAN FRANCISCO — Let’s be clear. Your personal information online is not always yours to control.

Thieves could grab a Social Security number stored unencrypted in a doctor’s computer; the National Security Agency could order an e-mail provider to unlock correspondence; even the phone company could supply the police with a map of your whereabouts for the last several months.

For now, short of living in a cave without a cellphone, there are no fail-proof technological tricks to avoid this exposure. But there are a variety of tools to minimize your digital footprint.

Some of these tools cost money, making digital privacy something of a luxury for those who can afford it. Others are free. But all of them take effort and awareness.

“A lot of people say, ‘I don’t have anything to hide,’ ” said Mike Janke, chief executive of Silent Circle, a company outside Washington that markets a private communications tool to individuals and businesses. “I say, ‘Tell me the last time you had a private conversation — or thought you did.’ ”

PROTECTING PASSWORDS Experts say never to use the same password on multiple sites. Reality says that following that advice is nearly impossible.

But keeping strong and safe passwords, which means keeping multiple passwords, is crucial to protecting accounts. A relatively safe bet is to use a password manager. They generate random passwords and store them in an encrypted safe, to which only you have the key, usually in the form of a master password. Several are available, including Dashlane, LastPass and RoboForm; some work better than others on mobile devices. Apple’s new operating system, iOS 7, includes a so-called Password Generator that can produce “a unique, hard-to-guess password” as well as “remember it for you.”

Two-step authentication is another worthwhile safeguard. Many large Web companies, including Google and Yahoo, along with recently breached services like LinkedIn, now offer this option. If you turn on two-step authentication, entering a user name and password sends a code to your phone by voice mail or text message. The service then requires that you enter the sent code. It takes extra time to set up and use the system, but far less than it would take to clean up a thief’s mess.

TRICKING THE TRACKERS Whether it is to avoid peeping criminals or advertising networks, there are several options for keeping your browser history to yourself.

Tracker blocking tools let you see the companies tracking your activities on the Web, and to block them if you wish. Some of the popular blocking tools include Ghostery, Disconnect and Abine. To the dismay of advertisers, some browser makers now offer consumers a way to block so-called third-party cookies, tiny pieces of code that track where you go on the Web.

Forrester Research estimates that 27 percent of Web users have used an ad blocking tool, a sharp increase from recent years. It is possible to take much stronger steps, too, and Tor is one of the most popular options. Originally developed for the Navy, and used by agents for the Federal Bureau of Investigation, Tor’s browser prevents Web sites from knowing who you are by rerouting Web traffic through a series of other points. Using Tor with your e-mail service, for instance, would most likely prevent a government agency from detecting your Internet Protocol address, though not from compelling a service provider to turn over your messages. Orbot offers an equivalent for the Android operating system; there is nothing for iOS.

A virtual private network, or VPN, can also help blur your tracks. It creates an encrypted tunnel between your computer and the VPN’s server, obscuring your Web browsing to others, including your Internet service provider. But some VPNs log your Internet traffic, compiling a rich history of your Web travels. HTTPS Everywhere, a browser extension, takes you to secure, encrypted versions of Web sites wherever possible, protecting you from eavesdroppers, for instance, when you are using public Wi-Fi.

If you do not want Google or Bing (the two main search engines) to compile your search history data, there is the upstart search engine called DuckDuckGo. Its founder, Gabriel Weinberg, says his company has no interest in saving user search history. The company makes money by serving advertisements based on the keywords searched, right then and there, and discards the search history. So if the government asks for user information (that hasn’t happened yet, he said), it will not get much. “If the data doesn’t exist, there’s nothing to hand over,” he said.

TRUSTING THE CLOUD Lawyers sometimes like to say that the digital cloud has fundamentally changed the relationship between citizens and their governments. If the police wanted to inspect your work files in the past, a search warrant was required to enter your office. Now, the police can turn to the cloud service you use to store work files. But when SpiderOak, of San Francisco, receives these inquiries, it cannot offer anything legible. Its customers’ files are not only encrypted, but users’ plain text passwords are not transmitted to the company. “Most companies ask you to trust them,” said Ethan Oberman, its chief executive. “Our theory is you don’t have to trust us.” The service costs $10 a month for 100 gigabytes of storage.

KEEPING CONVERSATIONS PRIVATE An e-mail is like a postcard — it can be easy for others to read. And an e-mail provider’s promise of encryption provides little comfort. For starters, when a message is sent from a Gmail user to a Yahoo user, for example, it travels on the wide open highway of the Internet, vulnerable to theft. And a government can order an e-mail provider to unlock the correspondence — whether through a search warrant from police agencies or a National Security Letter from an intelligence agency.

Moxie Marlinspike, a security researcher, uses the analogy of an offline lock and key. “Let’s say the door to my house is locked, but I keep the key Scotch-taped next to it,” he said. Anyone who can grab the key can get in.

P.G.P., or Pretty Good Privacy, is one system to encrypt e-mail communications, but it is relatively complicated to use. The brains behind that tool have now come together to form Silent Circle, the company run by Mr. Janke. In addition to encrypted e-mail — which Mr. Janke admits is the company’s least secure product — Silent Circle also offers encrypted phone, text messaging, file transfer and video chat services. The user gets a 10-digit phone number that works on Android or Apple devices.

The company does not keep a log of phone calls, which means that a law enforcement request even for so-called metadata is likely to be futile. A decryption key is produced for a phone call, video chat or text message made using its service; once the message is received, the key is deleted. But there is a serious hitch: the extra protection works only if both parties are using Silent Circle. The service costs $10 a month.

Mr. Marlinspike has also developed an encrypted text messaging app, TextSecure, now available on Android. Off the Record is another encrypted instant message service. RedPhone, built by Mr. Marlinspike, encrypts calls from end to end, and keeps no data itself, meaning that no telephone carrier can keep a record of those you talk to or comply with a wiretap order to monitor your phone calls. KoolSpan, a Bethesda, Md., company, offers its encrypted phone and data service to law firms, which are especially interested in safeguarding their client communications from hackers; former Attorney General John Ashcroft’s firm, the Ashcroft Group, is among its customers.

REMEMBERING THE BASICS Even the most advanced privacy tools might not work, though, if the basics are ignored. And perhaps the most basic safeguard of all — the equivalent of hand-washing in digital hygiene — is to keep software updated. A host of known security bugs are often fixed with each release, and ignoring those sometimes annoying calls to update are done at your peril.

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Browser Wars Flare Again, This Time for Phones and Tablets

But even if consumers are not so sure what Web browsers are (programs like Internet Explorer and Firefox), they have become a crucial business for tech companies like Google and Microsoft. That is because they are now the entry point not just to the Web but to everything stored online, like Web apps, documents and photos.

And as the cloud grows more integral, both for businesses and people, the browser companies are engaged in a new battle to win our allegiance that will affect how we use the Internet.

It’s an echo of the so-called browser wars of the 1990s, when Internet Explorer and Netscape Navigator fought for dominance on the personal computer. This time, though, the struggle is shaping up to be over which company will control the mobile world — with browsers on smartphones and tablets. Entrenched businesses are at stake. Google’s browser-based business apps, for instance, threaten Microsoft’s desktop software, and mobile Web apps threaten Apple’s App Store.

“Twenty years ago, we didn’t know how the Internet was going to get used by people, and we for sure didn’t know about mobile or tablets,” said Marc Andreessen, co-founder of the first major browser, Netscape Navigator, and an investor in Rockmelt, a browser start-up. “Mobile is a whole new level of reinvention, so it feels like we’re in the most fertile time of invention since the early ’90s.”

Browsers give Web companies more control over how people use their products, and data about how people use the Web, which they can use to improve their products and inform advertisers. Faster browsing leads to more Web activity, which in turn leads to more revenue for Web companies — whether searching on Google or shopping on, which built a Kindle browser, Silk.

As Mr. Andreessen put it, “Why let something be between us and our users? Let’s have as much control of the user experience as we can have; make sure our services are wired in.”

Google’s Chrome browser, for example, makes Google searches faster and simpler because people can enter search queries directly into the address bar. And its apps — like Gmail, Drive for file storage and Docs for word processing — are all accessible through any browser.

“Chrome makes it much easier for you to search, browse the Web and use Drive, Docs and apps, and we are fortunate to be in a position where when people do those things, we do better,” said Sundar Pichai, senior vice president of Chrome at Google. “Chrome is a platform, the underlying layer on which all our cloud operations run.”

Most people use either Chrome, Microsoft’s Internet Explorer, Mozilla’s Firefox or Apple’s Safari. In the biggest disruption to the market in 15 years, Chrome last spring toppled Internet Explorer as the most popular browser in the world, despite the fact that it does not come loaded on computers as Explorer and Safari do. It now has 36 percent of the global market, while Internet Explorer’s share has dived to 31 percent, according to StatCounter, which tracks browser market share.

A host of smaller companies, like Rockmelt and Opera, are also trying to grab market share, largely by focusing on mobile devices.

Browsers themselves are not lucrative businesses. Some, like Firefox, earn money from search engines like Google and Microsoft’s Bing that pay when people use the search bar built into the browser.

“No one is doing a browser to make money,” said David B. Yoffie, a professor at Harvard Business School who was co-author of a book about the first browser wars.

“Suddenly now, the browser has become the interface for the cloud more broadly, not just for traditional Web sites.”

In their search for dollars, browser companies are redesigning their products to follow consumers to mobile devices, social networks and cloud-based apps.

For example, new mobile browsers let people swipe through tabs with their fingers, automatically resize or zoom in on Web pages so they fit a phone’s screen and load pages faster than older mobile browsers. Some also sync with other devices, so things like most-visited Web sites, passwords and credit card numbers are available everywhere.

Nonetheless, browsing the Web on a mobile device is still inferior to using the desktop Web or smartphone apps. Apps, like those downloaded from Apple’s App Store and Google Play for Android devices, have more exciting features, are faster to load and are better optimized to small screens.

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DealBook: Pinterest on Wish List of Rakuten, Japan’s Amazon

Hiroshi Mikitani, the founder and chief of Rakuten, arrives for the Allen  Company conference in Sun Valley.Kevork Djansezian/Getty ImagesHiroshi Mikitani, the founder and chief of Rakuten, arrives for the Allen Company conference in Sun Valley.

SUN VALLEY, Idaho — Hiroshi “Mickey” Mikitani, the chief executive of Rakuten, would buy the rest of Pinterest — if he could.

Earlier this year, Rakuten, often dubbed the Amazon of Japan, led a $100 million investment in the social bookmarking site, at a reported $1.5 billion valuation. It was an eye-popping sum for a Web site that had no revenue and one that had also just raised money at a $200 million valuation just months before.

Mr. Mikitani says the price he paid was more than fair — and he wouldn’t mind buying more, assuming it came up for sale.

“I would love to buy,” he said during an interview with the New York Times at the Allen and Company conference on Thursday. “But I don’t think they would like to sell.”

So he’ll take what he can get. “We’re going to have a very good global strategic relationship with them, so that’s fine,” said Mr. Mikitani.

Some experts have questioned the merits of the Pinterest investment, which came on the eve of Facebook’s botched initial public offering. Indeed, the value of many Web companies have drifted lower in recent months. But Mr. Mikitani, who manages a personal Pinterest board, said he has real conviction in the fast-growing Internet start-up.

“There were very reasonable,” Mr. Mikitani said of Pinterest’s management team. “They were not greedy, they were not trying to inflate the valuation.”

Before making the investment, Mr. Mikitani said he considered Pinterest’s meteoric traffic, the quality of its membership base, the so-called “stickiness” of the site (the engagement of its users) and how the site helps retailers. As the head of such a big e-commerce platform, Mr. Mikitani said he was particularly impressed with Pinterest’s conversion rate, the number of users who made retail purchases after clicking on Pinterest links.

In recent years, Mr. Mikitani has been on an international buying binge.

His acquisitions include Linkshare and in the United States and PriceMinister, the French e-commerce business. Last year, he added book e-reader Kobo to his bursting portfolio.

Mr. Mikitani is not done yet. He said he has benefited from the relatively strong yen, which has made international deals more palatable. However, he provided little detail on his wish list.

“If there’s a good opportunity, we will consider it,” he said. “Sometimes, great deals just pop up.”

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In Silicon Valley, the Night Is Still Young


LET the rest of the country worry about a double-dip recession. Tech land, stretching from San Jose to San Francisco, is in a time warp, and times here are still flush.

Even now, technology types in their 20s and 30s are dropping a million-plus each on modest ranch houses in Palo Alto in Silicon Valley and Victorian duplexes in San Francisco, and home prices in some parts have jumped nearly 50 percent in the last six months.

Jobs — good, six-figure jobs, with perks like free haircuts and lessons on how to create the next start-up company — are here for the taking, at least for software engineers.

And for anyone with a decent idea and the drive to start a company, $100,000 to get it off the ground is easy to come by.

Yet, for all the outward optimism, even before the recent gyrations on Wall Street, old fears have been creeping in, nagging memories of the dot-com bust. You can sense it at cocktail parties in Menlo Park, at business conferences in Redwood City, inside the hipper-than-thou offices of young Web companies in San Francisco. Maybe, just maybe, these good times won’t last, and it will all come crashing down again.

“There’s this ’90s hangover people still have,” says Peter Thiel, a PayPal co-founder and tech investor.

Now the worry is that all the turmoil on Wall Street will spread West. Can Silicon Valley really prosper if the general economy tips back into a recession? Can you make a fortune on your I.P.O. if the market is falling? Probably not. But then, no one should work here unless she is prepared to be lucky. Even in worrisome moments, like now, the essential optimism of this place endures.

“There’s a ‘greater-fool theory,’ ” says Lise Buyer, who was a tech stock analyst during the dot-com bubble and is back with a consulting firm, the Class V Group, that advises on initial public offerings. “In Silicon Valley, we are as a species wildly optimistic. But if we weren’t, we wouldn’t have so many entrepreneurs because no one who’s being rational would ever found a company.”

And so start-ups are multiplying. Engineers are deciding that this is the right time to create would-be Groupons or Facebooks — “me-too companies,” valley speak for start-ups that are basically copycats of a winning formula — or yet another local, social mobile app.

Even more than buying a new Prius or jetting off to Cabo for the weekend, the new money set here wants to keep investing — and believing. Backing another start-up is a status symbol, the No. 1 splurge, and it captures both the tech industry’s belief in the future and its fear of missing the next big thing.

 “These are nouveau tech millionaires,” says Adeo Ressi, a coach for entrepreneurs. “It’s not that they don’t see the warning signs. It’s like roulette.”

Even before the fragility of the stock market became apparent, people here had been asking this question: Are we in a new tech bubble?

The optimists — or, some would say, the self-interested who stand to profit from the hype — note that the amounts being invested are nowhere near what they were in 2000, and that the companies this time are generally profitable and mature. The pessimists say yes, a bubble has been inflating, yet even they aren’t fleeing. They just hope to be the smart ones who get lucky and get out before it pops.

A bubble looks just like a boom, says Marc Andreessen, who touched off the first boom when his company, Netscape, went public in 1995. Frank Quattrone, the investment banker who took Netscape and dozens more companies public back then, says that today feels less like the height of the bubble and more like 1995, when tech companies were starting to go public but investors weren’t yet speculative.

Just four short years ago, social media and the iPhone were the hot new things, and money was sloshing around. But when the recession hit in 2008, Silicon Valley froze. Of course, that didn’t last long: by 2010, start-up investing was booming again with money from angel investors playing with their own cash, and this year the I.P.O. markets opened wide to tech companies for the first time since 2007.

Twenty-two tech companies went public in the second quarter alone this year worth $5.5 billion, the highest dollar amount since 2000, according to the National Venture Capital Association. Only six went public in all of 2008.

The valuations of young start-ups, meanwhile, have been defying gravity. Almost 1,000 raised $7.5 billion from venture capitalists in the second quarter, up 19 percent from the first quarter and 61 percent from the same period in 2009.

Miguel Helft contributed reporting.

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DealBook: The New Sun Valley Start-Ups

SUN VALLEY, Idaho — As their companies move toward public offerings, Andrew Mason of Groupon, Mark Pincus of Zynga and Mark Zuckerberg of Facebook are leading a new wave of Internet billionaires.

So who will head the next generation of multibillion dollar start-ups?

The agenda for Allen Company’s Sun Valley conference could provide some clues.

This week, the program features three young guns of Silicon Valley, all under the age of 30: Brian Chesky, the co-founder of AirBnb; Drew Houston, the founder of DropBox; and Adam D’Angelo, the co-founder of question and answer site Quora.

The three are scheduled to deliver presentations on Saturday morning to an audience that will most likely include Bill Gates, Mr. Zuckerburg and the founders of Google.

“It’s humbling,” said Mr. Chesky in an interview on Wednesday. “A year ago, I was working in the living room of a three-bedroom apartment.”

The new class of promising start-ups highlights the rapid speed by which Web companies are now forming and gaining traction. AirBnB, for instance, had roughly a dozen employees last year. It now has about 150.

The company, which helps travelers connect with users who have available rooms, has made 1.9 million bookings since it began operations in late 2008.

DropBox, a data storage service, has gained more than 15 million users in the last year, according to Mr. Houston.

“What’s amazing about this time, is that companies are getting started from nothing, and becoming incredible institutions in years, rather than decades,” Mr. Houston said.

Mr. Chesky said: “Adam, Drew and I are somewhat representative of how fast technology changes. Here you have all these industry veterans and moguls who have been doing this for decades and then you have us, basically working out of an apartment a year or two ago, with virtually no business. And now we have this huge opportunity.”

At the Allen Company conference last year, a daily deal upstart named Groupon garnered significant attention. One year later, Mr. Mason’s company is on the cusp of a billion-dollar-plus initial offering. The site also shared the stage with Square, which recently closed a $100 million financing round that valued that company at $1.6 billion.

The upward momentum in technology is certainly catching people’s attention. The trio of founders have been talking to several business leaders this week, including John Donahue, the chief executive of eBay; Sheryl Sandberg, the chief operating officer of Facebook; Mr. Mason; and Henry Kravis of the private equity firm Kohlberg, Kravis Roberts.

The Internet mogul Barry Diller, the chairman of IAC, sat down with Mr. Chesky on Wednesday for a nearly 40-minute discussion, according to one attendee. Although Mr. Chesky declined to comment about specific conversations this week, he said he was talking to people about how to expand a business and how to be an effective chief executive.

“When you become an entrepreneur and you get to a certain level, you can no longer turn to your left and your right, you need to reach out to people who’ve experienced what you’ve experienced,” he said. “I feel really fortunate to be in their company.”

Mr. Chesky says he really appreciates the opportunity to attend, because he remembers a time when no one wanted to invest in AirBnb. Faced with the prospect of failure in 2008, the AirBnb team started designing and selling collector edition cereal boxes for the presidential election. The team managed to sell $30,000 worth of cereal boxes, which he described as its angel round.

“In the beginning, when we launched, no one noticed,” he said. “There was a point when we couldn’t get access to anyone who had access.”

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Bits: Amazon Cloud Failure Takes Down Web Sites

A major, widespread failure in Amazon’s Web services business took down many Web sites Thursday.

The problems, which began early Thursday morning and had not been completely repaired by late afternoon, affected many Web sites including Quora, Reddit, GroupMe, Scvngr and HootSuite, which all posted messages to their visitors about the issue.

The Web companies use Amazon’s cloud-based Web services to host Web sites, applications, files and other resources. Amazon’s customers range from start-ups like Foursquare to big companies like Pfizer and Nasdaq.

Amazon lets these companies rent space on its servers and take advantage of its big data centers and computing power. But this means that when Amazon’s servers fail, the companies have little control over the situation, highlighting the risks of relying on so-called cloud computing.

Amazon did not respond to requests for comment, but the company is updating the status of its Web services and confirmed the service disruptions. It said it did not know when the services would be restored.

“Our high-level ballpark right now is that the E.T.A. is a few hours,” Amazon wrote at 2:09 p.m. Eastern time. “We can assure you that all hands are on deck to recover as quickly as possible. We will update the community as we have more information.”

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