New York startup king is betting on a local news game-changer

Silicon Valley has all manner of tech impresarios—from Marc Andreessen to Elon Musk to John Doerr to Peter Thiel.

But New York City? Not so much. Despite being “the most important city on the planet” and, yes, an ever-burgeoning tech scene replete with Flatiron District hipsters, the number of big-time tech entrepreneurs in Gotham is surprisingly small.

One of the most important is Kevin Ryan, founder and creator of some of New York’s most high-profile start-ups, including DoubleClick, Gilt Groupe and Business Insider. I recently sat down with Ryan to pick his ever-active brain.

First, I wanted to ask Ryan—who’s never short of strong opinions—about his newest venture, a local news venture called, (for now I would guess), Denverite.

So what the heck is Denverite? “It’s a site that competes with local sites like the Denver Post,” Ryan says. “It’s going after that local market of large cities in the United States, most of them have one newspaper and a website, struggling a little bit financially in all these markets. I think there’s an opportunity the way I thought there was an opportunity for Business Insider to compete with the Wall Street Journal and other large business sites.”

But Ryan himself said these papers and news sites are in trouble. How does he hope to succeed? “Whenever you have a completely focused online player competing against an existing player, say TMZ versus People Magazine, Business Insider and the Wall Street Journal, Huffington Post and the New York Times, they always get much more traffic and become larger because they wake up every day thinking about online, they execute better, they use social media better, they curate other content better and they have lower costs.”

I pointed out that Warren Buffett likes regional newspapers; Ryan corrected me saying that Buffett used to like regional newspapers, and that he was right but that was 20 years ago. Today, he says, Buffett is much less sanguine. Ryan added that he would continue to build out the Denver site for the next six to eight months and then look to expand, targeting cities from number four to 20 in terms of population, say, from Philadelphia to El Paso.

Ryan sold Gilt Groupe—which he founded in 2007—to Saks, or rather to its parent company, Hudson Bay Company, in January for a reported $250 million, which was a bit of a come down, as Gilt once sported a billion-dollar valuation. But Ryan says Saks “brings a lot to the table for Gilt.” He says customers can return items from Gilt to any Saks store and that Saks has relationships with more merchandisers. Plus, he says that Gilt has more online talent than its new parent in some areas, so that the companies fit well together.

I also asked him about Gawker. “It’s an extraordinary story,” he said. “Overall the company has been very successful. Nick Denton built it up without any outside financing. He did it over 10 years, he was there early, it has enormous traffic. It has always made money. It’s a valuable property.”

Did Gawker go too far? “I think so. There were stories that my guess that [Nick Denton] would regret they did,” Ryan says. “There were a couple where they were over the edge.” But Ryan says in general there was a reason they were successful – they broke stories and said things others wouldn’t.

As for Business Insider, Ryan says that he “miss[es] the property.” He acknowledges that while comScore numbers are down a bit lately because of changes by Facebook’s algorithm, the global numbers are doing very well. Overall, Business Insider is a “colossal success,” he says. (Full disclosure: Business Insider is both a competitor and a partner of Yahoo Finance.)

Ryan maintains that the IPO market is “solid,” saying the number of companies going public this fall should be more than the spring. Still, he acknowledges that many businesses are “happier to be private companies.”

Finally, I ask Ryan what he looks for when he’s trying to start up a company. “I want to see an industry that needs to be changed, that can be changed. I want it to be a pretty big opportunity that can be $100 million in revenue in 10 years. And one final thing, I just want to be interested by it. There are some things that I find intellectually interesting and I want to go after. The exciting thing is that opportunities are everywhere. Industries are being transformed. And so it’s a really exciting time.”

Not surprisingly then, there’s no sign that Ryan is slowing down any time soon.