Tom's writing is sometimes confusing in the way he constructs sentences.
If you expand the statement, it should read:
a 1/8 tsp should fill a ¼ tsp in 2 tries,
(a) 1/16 tsp (should fill a ¼ tsp) in 4 tries, and
a 1/32 tsp (should fill a ¼ tsp) in 8 tries.
Translated, he means:
2 times (tries) of a 1/8 tsp should fill a 1/4 tsp, etc.
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