When Ashton Kutcher first made the leap from actor to investor, he relied largely on his gut, investing in companies like Skype, Square and Foursquare because he was wowed by their founders and products.
"Consumer is my domain expertise," Kutcher said on the latest episode of Recode Decode, hosted by Kara Swisher. "I am a consumer, so I can really try the product and explore it."
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But despite several hits in his portfolio, and the portfolios of his firms A-Grade and Sound Ventures — including Airbnb and Uber — Kutcher also remembers the ones that got away. After asking his Twitter followers for recommendations on cool new apps, he was flooded with tips about two: Tinder and Snapchat.
"I started using Tinder's product and playing around with it and was like, 'This is amazing,'" Kutcher said. "The swipe-left, swipe-right, just that simple product feature, I thought was outstanding."
Not so much for Snapchat, which he passed on twice.
"I looked at Snapchat's product and I hated the product," he said. "I just thought it was like, a little crickety and a little rickety. It just wasn't beautiful or elegant. And I have this dumb, personal pet peeve about that, and it really bugged me."
"And I know the dirty little secret, that even though everyone thinks that there's privacy and that their information disappears, it still sits on a server somewhere, and it's totally hackable over time," he added.
"[Snapchat CEO] Evan Spiegel doesn't like hearing that," Swisher pointed out on the new podcast.
"But it's true," Kutcher countered. "Or, at least, it was when I was looking at it. They may have changed it, I don't know. But I went, the first hack, where these kids are showing whatever pictures they're showing to each other on this thing, the first hack that comes out it's not going to be good for the company, and it's not going to be good for the users, and it really, really scared me."
Today, Snapchat (which recently rebranded as Snap, Inc.) is valued at around $16 billion.
* Disclosure: Kutcher is an advisor to Recode's parent company Vox Media.