So, according to Blockworks, his deal with them is worth $100 Million per year, which I'd speculate probably includes equity in Stake.com: https://blockworks.co/news/crypto-casino-stake-revenue

Someone started a website tracking all his historical sports bets. Although he loses about 2/3 of them, surprisingly, he's actually in profit since his partnership with Stake started: https://thedrakecurse.com/