Kara Swisher

Recent Posts by Kara Swisher

Mahalo's Jason Calacanis in Better Days

As usual, serial entrepreneur Jason Calacanis makes lemonade from lemons–or is it vice versa?–touting cost-cutting at his human-powered search engine start-up and newest venture, Mahalo, almost as much as he touted its prospects when he started it up more than a year ago with $20 million in funding.

The colorful Calacanis has been around the Web space for a long time, with a range of ventures back in the day, like “Silicon Alley Reporter,” up to the last of which–Weblogs Inc.–was sold to AOL in 2005 for $25 million.

But in a blog post yesterday, Calacanis sang perfectly in tune with the new, decidedly grimmer, times. Thus, he announced the cuts at Mahalo, which include layoffs, with his typical showman style.

The venture was funded by–among others–Sequoia Capital and its wunderkind VC Roelof Botha.

But, after Sequoia lowered the boom on the start-ups it invested in recently, it’s no surprise they are lining up to show how well they can play “Survivor.”

Wrote Calacanis, in part:

Although we’ve got a significant amount of cash on hand, and the business is ahead of schedule in terms of traffic (4m uniques a month, double where we thought we would be at this point), we’re fairly certain that the advertising climate for the next two years will be severely depressed. To ignore this obvious fact would be irresponsible…While I anticipated and prepared for the ‘internet winter’ we’re now facing (you’ve read my posts and e-mails about the startup depression I’m sure), I failed to realize how bad the situation would get. It’s much worse than I thought it would be, and ignoring market conditions today would only mean deeper cuts down the road.”

Ah, for happier times, such as in these three videos of Calacanis, which I shot when life was quite a bit sunnier.

The first two are of my visit to Mahalo’s Santa Monica, Calif., HQ last summer (tony digs and giant screens for all) and the third is the video from when Walt Mossberg and I demoed Mahalo at the fifth D: All Things Digital last year.

Now that the plot has inevitably thickened, it’s interesting that Mahalo means “thanks” or “gratitude” in Hawaiian. And BoomTown is surely thankful for the ongoing drama that Calacanis brings to the Web.

Here are the videos:

Visit to Mahalo:

Interview with Calacanis:

Mahalo Demo at D5:

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I think the NSA has a job to do and we need the NSA. But as (physicist) Robert Oppenheimer said, “When you see something that is technically sweet, you go ahead and do it and argue about what to do about it only after you’ve had your technical success. That is the way it was with the atomic bomb.”

— Phil Zimmerman, PGP inventor and Silent Circle co-founder, in an interview with Om Malik