It's too early to say if his risks "keep working out". Restructuring is not a risk. His, and others', original decision to make the company a non-profit was also not a calculated risk in this sense.
When he was fired from OpenAI, his use of employee manipulation to regain his position is not a risk; it is the only option he had. It was his bond maturing, of carefully cultivated loyalty he had accrued over years. Gaining that loyalty was not really a risk. It was smart politics.
One risk he took is: signing away such a large portion of the company to Microsoft. I'm not sure whether that is working out.
Another risk he took is: neglecting and sidelining the "safety" portion of his organization. This caused a talent exodus and led to the formation of many competitors. I'm not sure whether that is working out either.
When he was fired from OpenAI, his use of employee manipulation to regain his position is not a risk; it is the only option he had. It was his bond maturing, of carefully cultivated loyalty he had accrued over years. Gaining that loyalty was not really a risk. It was smart politics.
One risk he took is: signing away such a large portion of the company to Microsoft. I'm not sure whether that is working out.
Another risk he took is: neglecting and sidelining the "safety" portion of his organization. This caused a talent exodus and led to the formation of many competitors. I'm not sure whether that is working out either.