Folk club bookings began to follow, and soon they were performing together for Ditchling Morris at Chippenham Folk Festival, and pivotally, Sidmouth Folk Week. After much encouragement from the EFDSS Gold Badge receiver John Bacon, Jack and Leon entered the Sidmouth Jig Competition, where they were awarded Best New Entrant and 3rd overall. Here they met Saul Rose, who Jack later gained a strong musical link with. It was also here that Jack joined Customs & Exiles, a North-West Morris group based in Wokingham, and where he played alongside Jim Sawyer (Jimbo) and Derek Tarrant (Derek the Nutter), who have both been supportive and encouraging of Jack and his playing. In parallel to this, Jack formed a connection with BBC Folk Award winner Jackie Oates, and was invited to perform with her, O' Hooley &Tidow and Lady Maisery at the infamous Nettlebed Folk Club (Oxfordshire), where Jack began to work on the larger stages of folk music.

In 2018, Jack decided to embark his academic research into the musics of the British Isles, and began studying his degree in Folk & Traditional Music (BA Hons). Through his time at Newcastle university, Jack was tutored by Catriona Macdonald, Kathryn Tickell, James Fagan, Nancy Kerr, Saul Rose, Julian Sutton, Emily Portman, Rachel Newton, Dave Gray, and numerous other critically acclaimed musicians. Here he gained performance experience at the Sage Gateshead, The Bridge Folk Club, and Anarchy Brew Co., and he began his career in online melodeon tutoring. During his first year at university, Jack was invited to perform at Celtic Connections, and with many performances in-between, as well as studying the art of audio recording, mixing, and mastering, Jack was invited in his final year to perform at 10 Downing Street, making him the first musician to ever perform on the doorstep of English Parliament.