Lost & Found Cigars inadvertently emerged in 2013 during the Caldwell's efforts to launch Caldwell Cigar Company. While visiting with Tony Bellatto of La Barba Cigars, he brought with him bundle of cigars in his bag.

With a passion for exploring humidors as a consumer, Caldwell transitioned into manufacturing, eagerly scouring aging rooms for finely aged cigars. During a visit to Tony Bellatto, he brought along a few bundles that immediately caught the attention of Tony and his father. Intrigued, they asked about acquiring more cigars, which marked the beginning of Lost & Found.

The brand's initial releases included Pepper Cream Soda, One Night Stand, and Lost Reserve.