About Us

Two Buttons Deep is a news and entertainment website creating original content in a way Upstate New York hasn’t ever seen before. To put it simply, the local news and radio market covers the 5 Ws: the Who, What, When, Where and Why of every story. That’s great and all, but we cover the two Ws often left untouched in the media world.

And those Ws are the Wow, and the What the F***.



Two Buttons Deep consists of a handful of select writers and personalities across upstate New York. We cover everything and anything we consider worth talking about when you’re going Two Buttons Deep with your friends (yeah, it’s a verb). What does it mean to be Two Buttons Deep? Let this quick tutorial explain it for you:

Starting to make sense? Ok, cool. And here’s a little bit more about the team behind it all.

Jack Carpenter, Co-founder and Video Producer


Jack is an upstate native who has been pursuing a career in entertainment for the past 10 years. After teaching himself the art of creating video for the web in middle school, he had surpassed one million views on YouTube by the time he finished his freshman year of high school. Continuing that momentum into college, Jack studied broadcasting at Champlain College in Burlington, VT. While there, he hosted a late-night talk show that aired across the state of Vermont, and even landed him an Emmy Award at the College Television Awards in 2014.

Jack also interned for Conan O’Brien and appeared on an episode of Jimmy Fallon along the way. After graduating in 2015, he took his production skills on the road for a college-based website and toured the country for six months creating original content. After that, he took what he learned (and what he learned not to do) in regards to running a website, and returned to upstate New York to start up Two Buttons Deep in Troy.

Taylor Rao, Co-founder and Editor in Chief


Taylor’s a trained journalist, and after 6+ years learning the ropes as a student, intern and freelancer at the Hearst Newspaper Group’s Albany Times Union, she teamed up with Jack to start Two Buttons Deep. With formal journalism training, editorial experience and an outgoing personality, it was time to get involved in a personal project from the ground up -with the goal to be as creative as possible and play by our own rules in this wildly changing media landscape.

And why do we do it?

We are doing this because we love what we do. We love writing, creating and entertaining, and Two Buttons Deep allows us to do all of those things right here in our hometown. We do it here in Upstate New York because we’re motivated to make change in an area with so much potential.

If you’re interested in contacting us, working for us, or anything else, email us at twobuttonsdeep@gmail.com or fill out this form and we’ll be sure to write back.