His rise has been as improbable as it has been impressive. After dropping out of college and taking on work as a carpenter in Chicago, he got his musical start by providing CDs for his fans to pass along to their friends. This led to a string of sold out shows and a record deal with Nashville indie Lightning Rod Records. After that he relentlessly toured for 4 years behind "Messenger" (2010) and The Great Despiser (2012), playing over four hundred shows, including stops at Lollapalooza, Bonnaroo, and The Newport Folk Festival.
The grind of four years of nonstop touring had taken its toll though, and by late 2013 he was ready to call it quits. Studio time was already scheduled though and deadlines had been set for a new record, so after a few weeks Pug was back to the business of writing songs.
"In retrospect, I was in a very unhealthy place. I was sitting in a room with the blinds shut and a notebook, forcing out words that weren't there and drinking astonishing amounts of bourbon. I was looking at it as a job... as a business obligation, and that is a very slippery slope." At that point he decided to make good on his promise from the previous tour. The album was put on indefinite hold. "I just needed to start behaving like a human being again. I needed to reconnect with my girlfriend. I needed to eat healthy food. I needed to go enjoy live music as a fan. I really needed to make sure I still loved making music, because I really had my doubts at that point."
The resulting layoff paid dividends in spades. When Pug set up camp in Lexington, KY in 2014 to record, he did so with some of the best songs he has ever written. The agenda was much simpler than previous albums. "The aim on this one was very straightforward. We wanted to capture the music just the way we play it, with minimal production. It was a very back to basics approach because ultimately that's what I love about music, and that's what I love about making music. I wanted to record these songs the way they were written and put them out in the world." The result is 'Windfall', a collection of songs that are as close as we've gotten to a road map to Pug's ambitions. He has collected plenty of the requisite Dylan comparisons over his young career but on this record it's easier to hear the sway of more contemporary influences like Josh Ritter, Ryan Adams and M.Ward.