[_ah]

It's like any muscle. Start with something small that feels very risky, but isn't. Maybe 5hr-per-week unpaid tech work for a charity you enjoy, or a 10hr-per-week paid gig. Buy and sell some stuff online for small money. Do things where, even if you failed COMPLETELY, it wouldn't really affect your life.

Eventually you'll find that your universe of "acceptable risk" has expanded. Previously risky things won't feel that way anymore.

Extreme risk tolerance is a skill, but it comes from a lifetime of trying things, having them fail, and finding out that actually it was okay.