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11 troubled Web companies: The next Kozmos?

"We are going to lose some good companies." That's the warning cry from investors in tech these days.

Some we won't miss, of course: the lame, me-too, or single-featured "products" masquerading as businesses. But be prepared. Some Web 2.0 start-ups that are well-loved by many are in serious danger of falling off the cliff.

The problem is that being loved is no guarantee for success. Even being used isn't enough. Remember Kozmo, the munchie messenger service from the last bubble? Not a person who used it didn't love it. In the interest of building a user base, the company was OK with losing money on every transaction in its early days. But when the time came for it to become a real business, it was too late. It couldn't transition to a viable company, and it folded. It was a tragedy.

Here, in no particular order, are 11 online services companies that could face a similar fate. Several of them are 2008 Webware 100 winners. Like I said, popularity isn't enough.

Twitter Although well-used by many and even relied upon by some ( like me), Twitter has yet to turn on a revenue model. It's not like the company would lose users, if it set up a minor advertising strategy as a test; people want to see the company make some money. Please, Twitter, turn on the revenue before it's too late.

Meebo This is one of the coolest online communication companies I've seen. I like its products and services. But the revenues for running branded chat rooms cannot be all that large. Meebo belongs under the wing of a larger company like Facebook or Microsoft, but with Meebo's expensive valuation and the coming cutback in M&A, I fear that its exits may be blocked.

TripIt A very useful service for organizing travel information. Wait, travel? Who's going to be traveling more often during the economic storm we're heading into? People are going to sit at home on their mattresses filled with cash, teleconference instead of go on business trips, and take vacations in their backyards. I fear for this company and other clever travel start-ups.

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Start-ups: How freaked out are you?

We've been covering the economic crisis in depth recently (see The tech downturn: How long and how bad?). If you're a tech entrepreneur, we'd like to know how the stories of doom and gloom are affecting you. So chime in. Answer these two questions:

Startups: How freaked out are you? ( polls)

Just in from GigaOm: Inside Details of Sequoia Capital's Doomsday Meeting With its Companies

Angel investor Ron Conway to portfolio: Cut expenses now

Ron Conway, an investor in more than 100 contemporary tech start-ups and about that many in the last tech boom, sees the current financial environment as very similar to the 2000-2001 tech economy meltdown. His advice, as he laid it out to me earlier today and to his portfolio companies yesterday in an e-mail (after the jump), is the same as it was then: "Raise money internally by reducing cost."

He says, "The funding climate is going to tighten no matter what we do. The sooner we can prepare for it, the better."

At least, he says, entrepreneurs are more mature and proactive than they were in the last downturn. They're coming to him, some with cutback plans and some just seeking advice. As he puts it, the ones who come to him and say, "Walk me through the steps I should be taking," are the ones that will weather the storm.

Conway still feels it's a great time to start a company: if you're a "great entrepreneur with a great business idea," he says, "now is as good a time as any." But "hold on to your day job while you are raising money." … Read more

Realism creeping into venture capital calculations

The opening party of Boston-based Northbridge Venture Partners' West Coast office in San Mateo, CA could not have come at a more awkward time. With the U.S. stock market sinking fast and rumors of venture capitalists being unable to access funds committed to them, I did not expect the shindig to be a happy affair.

But it was, on the surface at least, with free-flowing wine and sushi, and a crowded new office filled with hopeful entrepreneurs and curious VCs. The giant flat-screen in the conference room was tuned to the Red Sox game, not CNN.

Were the players … Read more

Tech entrepreneurs changing strategies, not products

Correction: Dave McClure's role at the conference has been corrected.

Proving that a fundamental characteristic of a start-up entrepreneur is unbridled optimism, the mood Thursday at Dealmaker Media's Startonomics conference in San Francisco was buoyant, in the middle of the United States' worst economic crises in a generation.

That's not to say that the game is not changing for entrepreneurs or the people who fund them.

On the funding side, ubiquitous valley VC Jeff Clavier's advice is straightforward: Raise as much money as you can. "If there is more available, take more." I asked … Read more

How start-ups can survive

In 2001, the first dot-com economy collapsed. New companies couldn't raise funds to continue operating. Existing companies couldn't go public or get bought. My employer (Red Herring) folded, as did hundreds of other businesses. Almost all companies with speculative growth-based (as opposed to revenue-based) business models died off. And Aeron chairs flooded the market.

We're heading into another start-up downturn right now. Erick Schonfeld on TechCrunch points out how the credit crunch will lead to a venture crunch, and Jason Calacanis' latest e-mail newsletter predicts that "50-80 percent of the venture-backed start-ups currently operating will shut … Read more

'I Can Has Cheezburger' book missing online vibrancy

If you're a big fan of LOLCats like me, then you probably are very familiar with Icanhascheezburger.com, a community site where the most active practitioners of the phenomenon involving funny pictures of cats mixed with odd, badly spelled phrases ply their trade daily.

To the uninitiated, LOLCats can be hard to decipher, especially given that many of them are subtle meta references to the phenomenon itself. So regular Icanhascheezburger.com visitors are well-versed in phrases involving things like "Ceiling Cat...," "I'm in ur...," "...ur doing it wrong" and so on.

Over the last year-and-a-half, the site has become massively popular, with tens of millions of monthly visitors and even a series of spin-off sites, all in spite of the fact that it was hardly the originator of the phenomenon.

Now, the creators of the site have cobbled together several dozen LOLCats from the site into I Can Has Cheezburger? the book. A slick little volume subtitled, "A LOLCat colleckshun," it features the famous fluffy gray cat so familiar to fans of the site on the cover.

I was really looking forward to the book, as I figured it would cull the best of the site's thousands upon thousands of user-created entries. And since I can always feel confident that a visit to the site will have me ROFLMAOing--rolling on the floor laughing my (butt) off--I expected that the book would induce much the same reactions, except even more concentrated.

Sadly, that wasn't the case. … Read more

What works: Five Web 2.0 products I still use

On most days, I put my hands on two to five new Web 2.0 products. I write up some of them, but pretty much forget about all of them by the time I wake up the next day. A few things do stick with me, though. Here's a list of products I am actually still using, weeks or months after the initial review:

Chrome

Google's new browser. Who needs it? If you have to ask, you haven't used it. (See all our Chrome coverage.)

Why I like it: Very fast. Very stable.

Areas for improvement: Extension … Read more

How to get reporters' attention at Web 2.0 Expo

NEW YORK--In the press room at the Web 2.0 Expo at the Jacob Javits Convention Center here, there are a ton of fliers, stickers, and press kits lying around for us reporters and bloggers to peruse.

It's kind of hard for any one of them to stand out. Unless you're like collaboration software start-up Octopz, which we reviewed last year.

The company's strategy: Leave out some bright turquoise-and-green stuffed octopi, free for the taking. No corny company logos, no attached pitch, just a cute stuffed sea creature with a flash drive press kit tied around its … Read more

TechCrunch50 swag bag: Room for improvement

No matter how loaded the VC, over-funded the entrepreneur, or jaded the journalist, you won't see many leaving a tech conference without the $15 of tchotchkes in the swag bag that comes with the show's $3,000 admission.

In the past, I've received some pretty sweet bags of stuff from conferences like Demo (although this year, as Center Networks reports, it was mostly air). Of the conferences I attend, though, the only one where the swag is still memorable is the Walt and Kara show, D. See my reports from D5 and from D6.

At TechCrunch50, the … Read more