The Poker Hand that Cost a Web Millionaire a Fortune

Ryan Tate · 06/21/10 11:56AM

The mythology of internet startups is all about big wins. But it's instructive, for prospective hustlers at least, to also look at the humiliating defeats — like this video of Web entrepreneur Jason Calacanis losing a $204,400 pot.

Don't Even Think About Trying to Resign From This Tech Company

Adrian Chen · 04/24/10 03:04PM

Usually if an employee quits to pursue another exciting opportunity, it is a time of celebration. Not for Mahalo CEO Jason Calacanis. One of his employees sent out a super nice resignation letter. Calacanis' response: "Horribly disappointed in you."

Jason Calacanis's funny money

Owen Thomas · 12/15/08 03:20PM

With Mahalo Answers, the latest Web project from Brooklyn-born blog blowhard Jason Calacanis, you can pay people to Google for you with fictional bucks. Genius!

The bubble that wasn't

Owen Thomas · 12/02/08 01:20PM

Jason Calacanis, the mop-haired founder of Mahalo, an overfunded Web directory, is musing on Twitter about "tickers and rallies past" — a Proustian substitution of stock markets for madeleines. But what, exactly, does he have to be nostalgic for?

Mahalo motormouth to launch mystery product in December

Paul Boutin · 11/28/08 01:13PM

I'm taking guesses now. What's "Project A," the seekrit product being talked up by Mahalo founder Jason Calacanis on his private mailing list? A recap of recent events: He launched a human-powered news feed at a time most companies were planning layoffs. After that, he performed a layoff, then trolled for new engineers to hire. Why do I like the often-blustery Calacanis? Because when I briefly worked for him as an Engadget stringer, I saw his approach to running a startup: Operate the business on a shoestring, but splurge on little things to make employees feel spoiled — a second monitor, a killer espresso machine, free dinners at places the staff can't afford. Don't hate him because he's rich. He always picks up the check. Anyway, here's his vague product pre-announcement:

"Hey Jason! What's going on with your valuation?"

Owen Thomas · 11/17/08 07:00PM

Tough times, frivolous junkets: That's the modus operandi of Jason Calacanis, the grandiloquent emailer-in-chief of Mahalo, the Internet's most overfunded Web directory. He and butler/assistant/videographer Tyler Crowley posed for a picture while on a trip to Japan taken shortly after he promised to curtail his travel schedule while laying off Mahalo staff. Can you think of a better caption? Leave it in the comments. The best one will become the post's new headline. Friday's winner:, for "Eric Schmidt's 20 percent time project." (Photo by namekawa; used by permission)

Times Said Shopping

Ryan Tate · 11/02/08 10:58PM

The troubled New York Times Company is running out of options. It owes more than $1 billion, close to half of it coming due in the next two years. But it just ruled out layoffs for the foreseeable future and will probably try to avoid cutting the $132 million annual dividend, since doing so could spark a boardroom revolt by high-living Sulzberger family members. So it would make sense if the company has been trying to sell, as Jason Calacanis, CEO of search engine company Mahalo, said on the This Week In Tech podcast last week. (Audio of his remarks lies after the jump.)

Your new business plan

Paul Boutin · 10/27/08 03:40PM

As a startup, you are now, officially, on your own. You can't count on your VCs saving you or some magical offer from Yahoo or Google showing up to bail you out. Taurus has laid off Fondue. You need to rewrite — no, not your business model. Your business plan. Mahalo CEO Jason Calacanis, in his latest private email, offers this advice:

Mahalo is hiring

Owen Thomas · 10/27/08 01:40PM

"Do you know that you're amongst the very best, but can't find a company that appreciates you or gives you the opportunity you deserve?" So begins Mahalo's come-on to developers. The bulldog-powered search engine just laid off a large chunk of its staff, including some developers. Why is it hiring more? We're sure Jason Calacanis, Mahalo's voluble CEO, has some entertaining spin, which we'll let him add it in the comments. But since his HR department didn't stamp the Craigslist posting with "DO NOT REPRINT," as Calacanis is known to do with his emails, we're republishing it below.

How many more rounds of layoffs are planned at Mahalo?

Owen Thomas · 10/24/08 06:00PM

What was Mahalo CEO Jason Calacanis doing in the weeks running up to this company's layoffs? Traveling around the world, to destinations like the World Knowledge Forum in Seoul, Korea. In his how-to-lay-people-off memo, Calacanis also promised to cut back on his travel budget — which struck me as an admission that his trips to speak at conferences, often on subjects unrelated to his work at his Sequoia-funded Web directory, were being paid for by his investors. Can you think of a better caption? Leave it in the comments. The best one will become the post's new headline. Yesterday's winner: Ted Dziuba, for "Traffic is the new profit." (Photo by JoopDorresteijn)

Is Microsoft ripping off Jason Calacanis's ailing startup?

Owen Thomas · 10/23/08 02:20PM

Talk about adding insult to injury. As Jason Calacanis was sucking his thumb about the coming startup depression, Microsoft quietly launched a competitor to his intern-edited search engine, which has just gone through the layoffs Calacanis predicted for everyone else. Redmond's experimental entry into the market is called U Rank, an experiment in collaborative editing of search results. The sites aren't that similar in their approach to helping users find websites — but they are eerily similar in their flowery logos and pastel color schemes.