App phones people so you can pretend to be their boss

What would you say to someone if you were randomly connected to them by phone and had the opportunity to roleplay as their boss? A fun new app allows you to play the Michael Scott, Bill Lumbergh, or whatever boss of your dreams, and help them get stuff done too.

Yesterday I sat down for lunch in San Francisco with Danielle Baskin, the app's co-founder. A mutual friend had recently introduced us in an email, using the subject line, "Rusty / Danielle – I can't believe you two DON'T know each other."

Our conversation was lively and ended up being nearly three hours long. As I sat there chatting with her, I totally got why our mutual friend wanted us to meet. Danielle is a rabid creator of many weird and wonderful things, a true Happy Mutant. (You may remember her Drone Sweaters, for instance, or from her interview last month on the Cool Tools podcast.)

She's got all kinds of neat irons in the fire and many of them seem to teeter on that line between art and something that is actually useful. Her latest project rides that line. It's a collaboration with programmer Max Hawkins and it started blowing up on Product Hunt this week. It's called Your Boss and she describes it as "an app that connects people working on solo projects in a call-based accountability buddy system."

She writes:

My co-founder and I are entrepreneurs and freelancers with many projects. We made an app to automate phone calls between us to keep ourselves on track, because we often work alone (without a boss). It turns out other freelancers also enjoy talking on the phone too! And want bosses.

We now have a wonderful community of "bosses", ranging from designers to programmers to illustrators, and all sorts of entrepreneurs — an immersive theater company founder, and even a pet psychic, are on the network. You never know who you will be connected to.

On the surface it appears to be a pretty straightforward peer-to-peer voice-based accountability app for self-employed freelancers but it's the element of play that makes it so special. It not only connects people randomly through a phone call but whoever is playing the boss can decide to get into their role.

"Hello, this is your boss calling. What are you working on? Because, uh, you apparently didn't put a cover sheet on one of your TPS reports."

On Cool Tools, she talked about the app's origin story:

"It started out as this joke, as most of my companies do. So, my friend Max Hawkins created this project years ago called, 'Call in the Night.' And it connects random people in the middle of the night in a phone call… It's kind of like Chat Roulette, except that your phone rings in the middle of the night and you pick up the phone and talk to people… When I learned about it, I was like, 'I want that but during the day'… And so we started just having random phone calls with a small group of people on this app called 'One on One' and it would just call a group of us, we were all friends, and we would just have to talk to each other. But most of us were actually self-employed, so we ended up just talking about what we were working on and then realized it was super helpful…"

The Your Boss app is currently only available for iOS but there is a waitlist for Android.

Thanks, Mark!