Selena Gomez - Postcards on the Run

Selena Gomez discovered the Postcards on the Run app in 2011, when she was bored and decided to buy in. She was part of a $750,000 investment in the company, which helps iPhone users print and send their own postcards. Like it’s 1873. Um, neat?

Ashton Kutcher - Petnostics

Venture capitalist Ashton Kutcher has made some incredibly smart decisions in the tech world. But it’s unclear whether his belief in dog urine will be one of them.

He recently invested in the Shark Tank invention Petnostics, a pet urine collection contraption that allows you to analyze your pet’s pee with your smartphone.

Linday Lohan - Just Sing It

Lohan invested in Just Sing It, a karaoke app, in 2013. This almost makes sense for a star whose singing career never took off. Almost.

It was an equity-for-publicity deal for Lohan, so she essentially “bought in” by promoting the app. But it didn’t appear to help her career much. Though both are still available, neither the actress nor the app have gained much steam.

Justin Bieber - Shots of Me

Bieber fans and selfies are almost synonymous. At least that’s what Bieber thought when he invested $1.1 million in Shots of Me, a program that allows people to chat via shared selfies. Yes: Shots of Me started as an app just for sharing selfies.

The simplicity of Shots of Me (now Shots) may actually be its downfall. It’s hard to tear selfie-taking youngsters away from Instagram and Snapchat.

Tom Hanks - Hanx Writer

If you’re looking to go back in time without ever leaving your iPad, you’re in luck! The Hanx Writer app upgrades (or downgrades, as the case may be) your keyboard to that of an old-school typewriter.

It’s great if you want the look of a typewriter without the feel of a typewriter. Though Hanx Writer was one of iTunes’ top apps in August 2014, there were probably a zillion better things for the award-winning star to invest time and money into.

Lady Gaga - Backplane

In 2011, Lady Gaga (Stefani Joanne Angelina Germanotta) and Atom Factory founder Troy Carter teamed to launch Backplane.

Backplane allowed groups of people to connect based on shared niche interests. You read that right: it was yet another social media platform. The idea was either too specific or too common, and the startup was sold off as of 2016.

Jay Z - Tidal

Jay Z created Tidal with backing from a group of A-list musicians. Because the world really needed a new music streaming service. Oh, wait — not really.

Tidal has seen lackluster growth. When asked about Tidal’s low subscriber count, Jay Z stated that Rome wasn’t built in a day. Will things improve for Tidal? We’ll see.

Jay Z — along with Shakira, Rob Dyrdek, Biz Stone, and others — also invested in a video sharing app called Viddy. The app’s trajectory was cut off due to competition from Vine. He sure knows how to pick ’em.

Leonardo DiCaprio - Mobli

Leonardo DiCaprio looks crazy-good in pictures, so it’s no surprise that he ponied up his part of $4 million to invest in a photo sharing app called Mobli. This would have been a new and novel idea … if not for a little thing called Instagram.

We’ll have to wait and see if the extra funding will save the app, but Leo might be better at making strides to save our planet than he is at tech investing.

Snoop Dogg - various companies

Calvin Cordozar Broadus, Jr. is a venture capitalist. You know him better as Snoop Dogg, the West coast rapper-turned-reggae star-turned-rapper again.

He has invested in Reddit, as well as UStream and approximately 15 other tech companies. It may seem like an odd match, but Snoop is making nerdy tech cool.

Justin Timberlake - MySpace

MySpace is still a thing, thanks to $35 million from Justin Timberlake and Specific Media in 2011 … way, way after the hip kids had moved on to Facebook and other platforms.

Has the nostalgic Timberlake’s star power helped? Not really. The focus on music and artistic sharing was a good play, but the social media app is still a ghost town in comparison with competitors.

Kevin Jonas - YOOD!

Celebrity influencers: You know them, you love (to hate) them. Back when he was still doing the boy band thing, Kevin Jonas used his popularity to launch his own location-based food-searching app, which you can still download today, called YOOD!

Sean Combs - Tinychat

Back in 2011, Sean “P Diddy” Combs and Ashton Kutcher teamed to invest $1.5 million in a program called Tinychat. There was a lot of excitement around Tinychat’s launch, because apparently, some people actually want to chat with lots of people on tiny screens simultaneously.

Unfortunately, Tinychat has paled in comparison with other similar apps. In 2014, Paltalk bought the app, so, for some reason, it’s not quite over for Tinychat.

Oprah Winfrey - Waywire

This tech investment came with talk-show-level controversy.

Mega-mogul Oprah Winfrey offered up part of a $1.75 million investment in Waywire in 2012. Waywire was a video site created in part by New Jersey politician Cory Booker. Despite grumblings that Booker’s involvement was a bit fishy, Oprah’s star power helped it gain momentum before it was sold in 2013.

Seth Green - Shodogg

Actor Seth Green is a funny dude, but his tech investment choices are funnier still. Green supported Shodogg, which wirelessly streams content from your phone to your computer. A super cool idea, for sure. So cool that almost every other streaming app already thought of and offers it.

Ryan Seacrest - Typo

Ryan Seacrest has his finger on the pulse of just about everything. So you would think he’d know how to pick ’em when it comes to investing. He threw $1 million into an iPhone keyboard accessory called Typo in 2014.

Despite a name that sounds like a mistake, it seems like a good idea, right? The accessory might have taken off … if it hadn’t been for that lawsuit. BlackBerry felt that Typo essentially connected a BlackBerry-esque keyboard to iPhones, so they sued. Oops? The outcome: The suit killed that would-be accessory star.

Neil Young - PonoPlayer

In 2015, Neil Young jumped in on a portable MP3 player called PonoPlayer, to the tune of $1 million. Slapping on a $400 price tag, backers claimed the gadget emitted sound at its highest quality. Initial users disagreed, and the player was poo-pooed.