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Like most workflows that work with date ranges, the easiest way to solve this is to generate all the dates between the start and the end and then group them to extract monthly start and end dates
As long as you have less than 1M entries to process this should work fine. More than 1M and you may run into memory issues since the Generate rows can produce very large record sets. If you have more than 1M records to process you'll need a date range based solution that doesn't expand your input data set.
Please note that you had an incorrect value in your excel sheet. Your Apple start date was 2019-12-25