With the popularity of e-sports I suppose Poker is retro now. Hard to believe its' been over 15 years since Chris Moneymaker changed the poker world and online gaming forever.
I think Poker always provides a lot of great lessons that can be applied in the real world. You pointed out some of the SV business/poker players who's run went cold...
When playing a tournament you can easily feel anxiety that the leader board is showing players with tons of chips and you're just in the middle of the pack, or worse.
Sort of like how we might read about competitors on TechCrunch raising tons of money. In tournaments, sticking to your strategy focusing on one hand at a time, keeping your head down ignoring the leader board noise, not forcing the issue and finally waiting for the right moments to be aggressive.
After a while you might pick your head up to find you've quietly built a really nice stack and when it counts and the tournament is "in the money" you're in the final 10% of players left. And that's when the fun really begins.