Earlier quoted context omitted.
Ah I missed that he was selling calls for stocks he owns. That makes it even less interesting IMO? The premiums on these options are small enough and now you're also capping upside on stocks you already own. And remember that black swan events happen once a month in finance, so I think people would be surprised how far OTM they need to go to actually get to a "minimal" risk of them being ITM.
Normally you'd wait until the volatility is a bit higher, sell a few covered calls against 5-10% of your shares. If the market jumps up, roll the calls out and sell more. If you get assigned, that's great, immediately sell a put. I've been able to do this against SPY/QQQ, rolling and never getting assigned. So it's all gravy on top of the existing market returns. You can eke out a few pct a year this way, but from a…
I think you're talking about the wheel strategy. Keep reading this at r/thetagang but I believe the premiums lately have been higher than normal so that's why lots of people suggest this. HN was one of the last places I would see this suggested.