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He tried and failed to launch a general purpose live streaming service with Justin. Eventually he pivoted into gaming, a niche where being tied to a desktop computer made sense.
But now the mobile market is mature enough for a sea change.
The comments on popular videos fly by far too quickly for the broadcaster to follow.
Often you see streamers squinting to make out a username, trying to reply in real time to the flood of compliments and questions.
"It’s all about the addiction to real time feedback and the nodes in the brain that it triggers," Sideman tells me.
Users can give digital gifts, essentially sticks, like hearts, fistbumps, or beers.
He was part of a group that believed everyone would soon be the star of their own reality television series, all broadcast on the web.
That included the infamous Josh Harris, a dot-com millionaire who imploded for his live audience, chronicled in the documentary We Live in Public.
He shared stories from his home life, and slowly began to invite fans into it, broadcasting from his apartment, from a cousin’s wedding, while driving in his car or getting a haircut.
"I was running a media technology agency for a while and trying to shove this down the throat of every client, but nobody wanted it," Sideman says.
Watching a You Now stream can be an overwhelming experience.
Tayser Abuhamdeh doesn’t have what most people would call an exciting job. “Eventually I started opening up, saying random things, telling jokes and laughing at my own jokes.
He works behind the counter at a deli in Brooklyn, a small shop that does a brisk business in snacks, coffee, and cigarettes. I started to act like people were there watching, and that’s when they showed up.” Abuhamdeh’s routine was subtle.