Earlier this week, I stopped at the Palo Alto offices of General Catalyst Partners, an East Coast heavyweight that’s been politely muscling its way into more West Coast startups since planting a flag in the Bay Area in late 2010. One of those companies is Snapchat, the popular mobile messaging startup, and one of the investors I sat down with was Niko Bonatsos, who first brought Snapchat to General Catalyst’s attention. Among other things, we discussed why Snapchat’s most popular feature is no longer “snaps.” Our conversation has been edited for length.

Snapchat users appear to be less and less interested in the company’s “ephemeral” features. Is that a concern?

It’s the same thing that happens with other software products. When they get started, they’re very simple. Over time, their user base diversifies. So with Snapchat’s newest release, you can basically do a live video chat with others on Snapchat rather than one message at a time. And that’s fantastic. In the past, Snapchat was the icebreaker; now you can do much more. It’s still probably the fastest-growing app out there.

What early signals do you look for when it comes to non-transactional products like Snapchat?

If there’s anything that people are talking about in online communities, or if in reviews of apps, you see polarizing reviews, these are good signals.

When you’re controversial, it fuels word of mouth, which also gets amplified by the media. Back in the early days, for example, Snapchat was perceived as the ultimate tool [for lascivious] texting; it wasn’t true, because 75 percent of the user base was girls. But the media picked it up. Later, Facebook launched Poke, which was characterized as a Snapchat killer. Most people didn’t know Snapchat [at that point], and they looked it up and downloaded it. Controversy is great when it comes to building a brand and acquiring users for zero marketing spend. Obviously, you have to graduate from one controversy to another, or three to six months later there’s fatigue, but it can be controversy because of behavior, content, or because your product annoys people.

So investors should be looking for annoying apps.

Yes. With Snapchat, a lot of parents were very annoyed with it. With [anonymous messaging app] Yik Yak, a lot of schools and parents were annoyed. With [the mobile dating app] Tinder, people were telling their friends, “There’s an amazing app where I can check out girls and if I like them and they like me back, maybe we can start chatting and hook up later.” Meanwhile, older people were like, “This is terrible. What are young people doing these days?”

Secret and Whisper, apps where people share confessions and gossip anonymously, are controversial and, to some, annoying.

But their word of mouth isn’t as strong. Things don’t spread quickly from one community to another. Secret hasn’t managed to break out of its techie, Silicon Valley roots. You can see that it has something like 100,000 Android downloads. It launched on Android [in mid-May], but for a company that has raised so much money and been so [buzzed about], you’d expect some more.

I’m also a little hung up by the names Secret and Whisper. How many secrets do you have, really? Maybe one a day? Three times a week? I get the value proposition of the product; it’s like a Twitter parody account. But most content is, “My girlfriend just broke up with me,” or “I hate my boss.” It’s heartbreaking and after a couple of weeks, you don’t want to go back.

Before I go, what’s one last trend you’re seeing?

How fast we’ve gone from single apps to portfolios of apps. Google now has 150 apps between iOS and Android. Facebook has about 40. The world basically saw what happened in China, where companies like Tencent [the Chinese Internet company] now have [hundreds of] apps and do a lot of cross promotion and [essentially] game the app store. Mobility into the top 100 has become much harder for early-stage startups as a result, and if you aren’t in the top 100 app [download rankings], no one can find you. That’s the opportunity and the challenge.

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