Publicly available material confirms that in E40 the Besties talk about an upcoming/ongoing Italy trip, Jason’s heavy gelato and pasta consumption, and a “one meal a day” challenge, which matches the context of Chamath joking that Jason will gain significant weight on that trip.(podcasts.apple.com)

Later, E44 is explicitly labeled as including an “Intro & Italy recap,” indicating that the trip had finished by August 28, 2021, and was debriefed on-air.(podcasts.apple.com) However, the accessible summaries and transcript stubs for E44 (and E40) from sites like TranscriptForest and Glasp do not include any concrete statement about how many pounds Jason actually gained or lost, nor any explicit callback that resolves Chamath’s “+15 lbs” prediction.(glasp.co)

Broader searches of Jason Calacanis–related content (including later All-In episodes where they discuss weight and obesity more generally) likewise do not surface any reliable, specific number tied to that 2021 Italy trip.(allin.onpodcastai.com) Because Jason’s exact weight change on that vacation is not publicly documented and the show appears not to have reported a clear outcome of the bet, there is no verifiable way to determine whether he gained “about 15 pounds” as predicted.

Given that the event is long past but the outcome is not knowable from available sources, the prediction’s accuracy must be rated as ambiguous rather than right, wrong, or merely too early to tell.