For students wishing for a professional life in politics or international affairs, it’s not unusual to attend the George Washington University, using its curriculum and location as a direct line to an internship with their local congressman or woman and a life in politics.

Such was the case with singer-songwriter Cautious Clay (née Joshua Karpeh), who entered GW earlier this decade. “I thought that I wanted to be involved in international affairs at one point,” explains Clay, a Cleveland native, who chose the topic as his major. “The funny part is I never, ever got involved in any type of meaningful way.”

What turned out to be more meaningful to Clay was his jazz studies minor, performing in GW jazz ensembles and the Latin band, and focusing on gaining other musical experiences, performing in local groups and frequenting DIY shows.

“I’d been performing as a saxophone player in college. I was in this band called Lucky Dub. They were kind of big in D.C. At one point we played the 9:30 Club,” says Clay, now 26. “I also went to a lot of DIY shows in college. A lot of my friends were in bands like Sun Cycle and a bunch of different bands. … Not necessarily the type of music I was making but I was into going to the shows and being a part of what it was.”

What Clay couldn’t possibly have known at that time was that a mere four years later he would be polishing off 2019 with a streaming hit, his third EP Table of Context under his belt, and a return to the 9:30 Club this weekend as a headliner.

Upon graduation in 2015, the reality of post-college life led the budding musician to a career in real estate, first in D.C., then in New York City, something Clay chose for the most basic reason. “I needed a job to pay my loans, which was my main focus at the time,” says Clay. “Pay the bills and continue doing music. That was always my plan.”

With the move to New York—and the fact that a passion for real estate never developed—Clay focused on writing and performing his own songs, building the type of varied repertoire you would expect from a multi-instrumentalist with a diverse musical background. The resulting material—a hybrid of electronic elements fused with pop, jazz, hip-hop, and R&B—gained notice after he posted them on SoundCloud along with his remixes of popular songs, including Sam Smith’s “Lay Me Down” and Billie Eilish’s “Ocean Eyes.”

Bolstered by his SoundCloud success, Clay released the single “Cold War” in late 2017, a song depicting a stalemate (and stale place) in a long-term relationship. With Clay’s legato vocals and heart-on-his-sleeve lyrics, the song took on a life of its own after being featured in HBO’s Insecure and in the movie Booksmart. With the release of a pair of independent EPs, Blood Type and Resonance, in 2018, Clay found plenty of new fans in the music industry. One of them was John Mayer, someone he connected with the old fashioned way: through Instagram DM.

The social media friendship blossomed into a working relationship: Mayer and Clay collaborated on “Swim Home,” featured in Season 3 of Netflix’s 13 Reasons Why, and “Carry Me Away,” a single Mayer released in September.

Unbeknownst to Clay, as he was collaborating with Mayer, “Cold War” had somehow caught the ear of Taylor Swift, who decided she wanted to sample the track for her song “London Boy” from her recent album Lover. Clay thinks the sampling might have happened thanks to a chance meeting with one of her producers, Jack Antonoff, while hanging with Mayer.

“We were walking out of getting dinner late night in L.A. and we ran into Jack,” explains Clay. “Jack and John know each other. I had never met Jack before. I knew who he was but I didn’t even introduce myself as Cautious cause I didn’t know if he would even know [who I was].”

While any future collaborations remain to be seen (or heard, rather), Clay’s been quite content building his show as a headliner, touring around Europe for the last several months and getting his band to a place that comfortably lands between being tight and spontaneous.

“Every show is different and my band is really, really good,” says Clay. “I think the biggest takeaway people have is that I play a lot of instruments. It’s pretty conventional and unconventional at the same time.”

Cautious Clay plays 9:30 Club on Dec. 13 with special guest Remi Wolf. 10:00 p.m. Tickets $25.