It is entirely possible that Reddit's CEO compensation is structured so that any chance at valuation doubling, no matter how unlikely, is worth far more to him than his opportunity cost upon valuation halving, no matter how likely.
(in general, if outside investors look for properly aligned incentives, the mathematics of diversification suggests they will arrange for individual portfolio companies to each be run far more riskily than they want their portfolio in aggregate to perform)
Why do people keep repeating this? Twitter was not heading "straight to bankruptcy". They became profitable in 2018. Due to lawsuits they lost a good amount of money in 2020, but things got better towards 2021 again. They were far from bankruptcy, only since Musk settled them with additional debts are they heading towards it full speed.
(in general, if outside investors look for properly aligned incentives, the mathematics of diversification suggests they will arrange for individual portfolio companies to each be run far more riskily than they want their portfolio in aggregate to perform)