If I invest $300,000 with Endowus, do you immediately put all my money to work or do you phase the investment in gradually?

Personally this depends, looking at the current market conditions, I'd most probably invest in tranches. You can't predict the bottom so the best strategy is to buy at a price you are comfortable with !

I'd recommend setting target prices and when the stocks hit the target prices, just hit the buy button.

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Hi Anon,

Answering directly, we will invest the full amount for you, but you may not want to do it. I will request you to drop me an email at [email protected] if you are unsure if that is the best course, and talk you through your thought process, to be honest. It is a huge sum, and I would like to understand more about your personal circumstances, current investments before making any suggestions.
Just answering more generically, lump sum investing (put all at work at once), on average gives higher average returns, and also wider range of investment returns, while gradual investments (dollar cost averaging) may have lower risk in terms of range of returns, it has lower average returns. Hope this helps! ​​​