Thank you for sharing further details and I apologize for the delay in getting back on this.
During troubleshooting, I noticed that some extra space was coming as part of the output of the view "Challenge Done (get entrepreneur)".
( i.e. from shortcode [wpv-view name="challenge-done-get-entrepreneur"] )
Removing the empty line from the nested view "Challenge Done (get startup)" removed that space.
( screenshot: hidden link )
And as a result, the parent item is now also selected, correctly.
( screenshot: hidden link )