No Stranger to Controversy, Jason Calacanis Starts a New Venture

The months leading up to the launch of Jason Calacanis' new search engine, Mahalo, were filled with speculation and intrigue. What would the founder of The Silicon Alley Reporter and Weblogs Inc. unveil for his third act?

Calacanis' former competitor Nick Denton (founder of Gawker Media and editor of Valleywag) published rumor after rumor in an attempt to break the story on his old rival's new game. Most of the rumors, Calacanis later claimed, were actually planted by Calacanis himself.

That's just a sample of why Calacanis, who in addition to running Mahalo is also entrepreneur in residence at Sequoia Capital, is one of the most interesting businessmen to survive the first dot-com bust and emerge as a significant player in the "web 2.0" world.

(Editor's Note: In accordance with Calacanis' wishes, we conducted this interview via e-mail. We've edited the following interview for clarity and brevity, but we'll post the full, unedited transcript on Epicenter later today.)

Wired News: You're based in Santa Monica, far away from Silicon Valley. Should tech startups stay away from Silicon Valley and the Bay Area?

Jason Calacanis: I think the Bay Area is great if you need to get a profile going. However, if you have a profile already, you can draw talent to your operation. For me it's so much easier running the company in Santa Monica, where I'm not battling with 1,000+ Web 2.0 startups for every PHP developer within 100 miles of Union Square.

WN: Some are calling search engines the new operating system. Do you agree?

Calacanis: I've been saying that for a while. I think people say this because search is a base for people's web-based operations, like Windows was for the desktop.

WN: What is Google's blind spot?

Calacanis: No one will displace Google for the next 20 years -- minimum. There is no blind spot. It's their world and we are all living it.

WN: It appears that appliance computing is inevitable (i.e., simple computers for web browsing and entertainment, rather than full-fledged, completely hackable PCs). Agree or disagree?

Calacanis: People have been talking about the death of the PC for 20 years -- it's not gonna happen. People like rich applications on their desktop, and there is no reason why you can't have both a rich desktop and a light, cloud-based application framework. Why is it always either or for people?

WN: Other than not placing ads on Wikipedia, as you've discussed before, what is wrong with Jimmy Wales' business model?

Calacanis: Jimmy's business model for Wikia is advertising, from what I can tell. Mahalo's business model is advertising. Yahoo, Google, Ask, AOL and MSN are all advertising-based. So I don't see anything wrong with advertising-based search.

From what I understand Jimmy is making open-source search software, something similar to Lucene or Nutch that will crawl and index the web. If he makes that work and it is better than Google's results, we will use it for our long-tail searches. So, despite the fact that Jimmy and I battled over advertising on Wikipedia, I think we might actually become partners in search. Disappointing for the press, I know.

WN: What are your top internet-media favorites (not counting major corporations)?

Calacanis: I loved Ze Frank when he was on. For tech I like the DailySearchCast, TWiT and anything Veronica Belmont does on CNET. I think Perez Hilton is a riot, and the rest of my consumption is by people: Folks like Dave Winer, Fred Wilson, Mark Cuban, Brian Alvey, Jeff Jarvis, Xeni Jardin, etc.

WN: As a co-organizer of the TechCrunch20 conference, do you, as an agent of Sequoia Capital, have first dibs on presenting companies? If so, how do you defend that arrangement against critics that might feel it is unfair? What, if any, guarantee are you giving other potential investors that they will get an equal shot -- a "first look" -- at funding the selected presenting companies?

Calacanis: We don't have a first look, that's false ... you need to do some research! Companies can select if they want to share their business plans -- go read the application on the website and stop believing what you read on Valleywag!

(Editor's Note: The TechCrunch20 application (.doc) states that, in order to be selected for a slot at the event, entrants must first submit at least a portion of their business ideas to TechCrunch20. Calacanis and Michael Arrington, the organizers of the event, are both actively involved in other for-profit investments. )

WN: The subject of diversity in the internet business came up recently when Denton criticized the selection of MC Hammer for TechCrunch20 as tokenism.

Calacanis: We added Hammer because he is an expert on entertainment and because he is learning about the internet. There are other celebrities like Will Ferrell and Natalie Portman doing the same thing and we would invite them to join the panel for the same reasons -- and not because of their race or gender. That being said, I think folks should make an effort to make conferences diverse while maintaining standards of excellence.

WN: Would you ever present your startup company in search of funding to a panel of experts that included MC Hammer?

Calacanis: Sure. He's one of 20 folks (on the panel) and he brings the entertainment side of the business to the panel. I don't think anyone else on the panel has had as much reach in pop culture/music/entertainment.

WN: What is the central business or life lesson you've gleaned from your personal exposure to Mark Cuban?

Calacanis: Energy is everything. Mark only does things that he has passion for, and as a result he is high-energy and motivated to win. I think that's why he has a lot of winners around him.

WN: The focus of the internet frontier has shifted from the pipes, to search, to community, to blogs, and now video. … What's next?

Calacanis: Curation. The web and physical world is plagued with abundance -- people need help sorting through all the good and bad stuff out there. The tyranny of choice is causing major psychic pain and frustration for people.

WN: Professionally, what is the Calacanis endgame?

Calacanis: Buying the Knicks and bringing an NBA championship to New York City. I've been saying that for 10 years!