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The only way I think is transforming the data. If the data is in a database or xls, you can use Custom SQL something like this (not the exact syntax..) but you get the point.
select user, start time as time
select user, end time as time
Hope this helps.
You can reshape the data dynamically with cross join technique #1 in The Cross Join Collection.
I have done so in the attached workbook. This is the query I used:
SELECT * FROM [data$] d, [lookup$] l WHERE d.[start time] <= l.[end time] and d.[end time] >= l.[start time]
Custom SQL isn't supported in the newest Excel connector.
Therefore one needs to open Excel with the Legacy Connector:
Here is a screenshot from attached workbook:
Attached Workbook Version: 8.2