Q&A with Jason Calacanis, Founder & CEO, Mahalo.com

After Bubble 1.0 burst, Jason Calacanis renamed his Silicon Alley Reporter the VentureReporter and sold it to Dow Jones – now Rupert’s DJ. Five years ago, Jason sold Weblogs, Inc., a network of 85 blogs, to AOL for $25 million. He recently founded Mahalo, a human-edited directory that he hopes will someday rival Google.

Jason will be delivering the afternoon keynote at Search Engine Strategies New York today. We recently caught up with Jason to discuss some of the views on search that he might share during that conversation.

Kevin Heisler: You’re a natural-born seller. Everyone expects you to pitch Mahalo. Shall we get that out of the way now? Pitch us.

Jason Calacanis: I pitched Mahalo to the search industry three years ago, before I had the idea. No need to explain it again.

KH: Big picture: What are the factors pushing computing into the cloud?

JC: Free is the driving force in software today. Real e-mail (IMAP/POP), backup, and office suites are all free today, and that was unthinkable 10 or 20 years ago. In another 10 years, there will be things like unlimited web hosting, wireless access, and mobile phones. Anything that can be paid for will become free, in my mind. I’m betting the Kindle will be free, with a subscription to audio books and e-books, this year.

KH: About a month ago, you were the number one user of Twitter, per Twitterholic. Why should the SES audience use Twitter, and what can they expect by following you?

JC: My Twitter feed is perfectly balanced: 33 percent insightful commentary, 33 percent my personal life, and 33 percent spam.

KH: You blogged on calacanis.com: “If there was one other company I could be the CEO of (after Mahalo), it would be Twitter.” Why?

JC: I think it’s the next company to [reach” 100 million users a month and a $1 billion valuation. It’s the new IRC, POP, RSS, XML, Jabber, or pick your format – and it’s proprietary, but open. The value of Twitter will be huge in five years. It will be the next global communications platform.

KH: Then you named some surprising companies, none a sure thing: Ning, CNET, About.com, and Qik. Jeremiah Owyang (Forrester Research) noted scores of vendors in the white-label social search platform business are flooding the market. Low barriers to entry, easy-to-deploy software, media, and VC-fueled frenzy.

JC: Ning is going to be huge because people will want to own their social network. A decade ago, folks thought a GeoCities page or a blog at blogspot.com was just fine. Then their blog or personal page became important to them, and they wanted to have it at mydomainname.com. The same will happen to Facebook and MySpace. Folks will realize their social network is worth a lot of money, and they will want 100 percent control over it. Today, you have the illusion of control on social networks, but the truth is you don’t own your own profile, and it can be taken from you at any time.

KH: About.com was the original human-updated directory. It’s now search-optimized by The New York Times’ SEO (search engine optimization) honcho, Marshall Simmonds. Would you update it with Mahalo-style features?

JC: I would like to own it just for the brand and for the Guides. Sure, the quality has gone down over the years due to neglect from a funding standpoint, but the mission is still there: to guide people. Since I can’t have the brand, maybe I should just reach out to the Guides?

KH: CEO of CNET? They’re fighting with a consortium of activist investors led by hedge fund JANA Partners, which wants to expand the board and nominate its own directors in a bid to boost its share price. Are you a glutton for punishment? Or do you think by the time this hits print, Google will already have a stake in CNET Networks?

JC: There are great nuggets inside of CNET, so I would want to own that for very specific properties they’ve bought over the years that I think could break out if someone really got down to business with them.

KH: Qik, you tested it. Live videocasting from a mobile phone via Internet connection streamed straight to a site with 5-second delay. Plays well with Twitter. Why not just buy the company?

JC: I’ve learned long ago that it’s really hard to run multiple companies at the same time. I’m 110 percent focused on Mahalo and 20 percent focused on the TechCrunch40 event. That’s my life going forward for some time to come. Qik is the first of many services to have this feature, so it’s their game to lose. Frankly, I’m thinking Twitter will allow video, audio, and photos soon. I’ve been pushing them on it hard.

KH: There are a lot of questions about privacy and Big Brother. Software and application developers and hardware manufacturers seem to be pushing technology out before it’s ready. Will consumer apathy induced by technology overload and frustration override Big Brother and privacy concerns?

JC: Users don’t care about security until it’s compromised. Same thing with backups. So, the natural order of things is companies don’t focus on security and privacy until something like the AOL Data Valdez happens. Then everyone gets focused again. It will go back and forth, but the truth is Andy Warhol and Josh Harris were right: people want to live in public.

KH: Nick Carr cautioned SEO professionals to use their power ethically. What advice would you offer to SEO companies faced with ongoing ethical dilemmas? Or is the Internet by definition amoral?

JC: SEOs have two choices: (1) commit seppuku, or (2) turn from the dark side and make amazing content and services that help people. Social search and the semantic web are the end of black-hat SEO. It will take five years, but the clock is ticking… tick tock, SEOs!

Look, no SEO can crack Mahalo; it just can’t be done. Any spam or thin affiliate site that makes its way into Mahalo will be rejected very quickly by the community.

As time goes on, the amount of work for an SEO to rank a thin site is going to be two to three times the amount of time it takes to make a sustainable, high-quality site. Would you rather spend six months trying to get cheap-mobile-phones.com to rank or spend six months investing in the next Engadget?

Frankly, most SEOs are really smart and hard working; they’re just horribly misguided. They focus too much on the tricks to get people in the door and not enough on what people eat when they’re inside the restaurant. I think SEOs are highly adaptable, so I suspect you’ll see a large number of black-hat SEOs throw the flag up and go legit. I know many are already doing that.

KH: The Donald asks you to revive The Apprentice. Who’s in the boardroom, who gets to play, what’s the prize, and what tasks would your apprentices have to complete?

JC: Hmmm, that’s an interesting question. Task: build a site that ranks for the keyword mortgage. Highest rank wins. Participants: Michael Gray, Nick Denton, and Martin Nisenholtz from The New York Times. Boardroom associates would be Marissa Mayer and Mark Cuban. The prize is $1 million in AdWords, 12 hours on the Google Jet, and a MacBook Air autographed by Steve Jobs.

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