Should one invest a high (CPF OA) amount for the initial investment with Endowus or should one start a small (CPF OA) amount for initial investment with Endowus?

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It depends on your personal preference, there is no right or wrong answer to this. im not sure what is offered in endowus but generally, markets are rather frothy right now.

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the safest bet would be to start with a small amount and DCA in.

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the benefits of investing a lump sum initially would mean you get a higher return if the underlying asset continues to grow; whereas the downside is, after investing the lump sum and a downturn happens, it would incur you with more paper loss than the first option.