How the fastest-growing digital media company in the region started from scratch
Two Buttons Deep began in 2016, founded by lifelong Upstate New Yorkers Jack Carpenter and Taylor Rao as a humble blog focused on “stuff worth talking about.” Within a few years, the team leaned into their video skills and quick-form social media content, and the brand began to evolve. Today, Two Buttons Deep operates like a late-night show built for social media, creating topical, humorous content rooted in the stories that define the Great Upstate. In the early days, our only viewers were our moms. But the content spread, our network expanded, and the company continues to grow—one button at a time.
In 2020, Two Buttons Deep expanded our world with the launch of The Buttonista—a fashion and lifestyle persona documenting life in Upstate New York, along with a weekly podcast which regularly hosts live recordings around the area.
In 2022, we added the beloved Around Albany page to the 2BD world—and that was just the beginning. We expanded that concept into a full lineup of “Around” accounts covering events, businesses, and local history across multiple cities including Saratoga, Schenectady, Troy & more. Today, many of them rank among the most-followed city-focused pages on social media.
Today, Two Buttons Deep spans a network of brands reaching over 500,000 followers, each tied together by an underlying mission to elevate Upstate New York through intriguing, humorous, and culturally rooted digital storytelling. 2BD has grown into the region’s fastest-rising media company—and yes, our moms are still very proud.
We hear this question all the time.
According to folklore, “Two Buttons Deep” started when Jack and Taylor were in college and
used the buttons on their shirts to signal how buzzed they were while at parties. No buttons
deep = sober. Two buttons deep = the perfect level of fun where the conversations get good.
Three buttons deep? Well, let’s just say that’s best left off the internet.