I'll leave the solution I found here in case it's useful to anyone:
.left_join(DB[:events].select{[user_id,
min(start_time).as(min_start)]}.where(active: true).group(:user_id),
user_id: :id)
.left_join('events', 't1.user_id = e2.user_id AND t1.min_start =
e2.start_time', {table_alias: 'e2'})
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