Seems that you're unsatisfied with the risk/reward balance, but you're not yet ready to go all the way to the other side. What about working as early employee

Seems that you're unsatisfied with the risk/reward balance, but you're not yet ready to go all the way to the other side. What about working as early employee or a co-founder on a new venture? It won't be as hard as being the founder and CEO, but you'll still exchange some stability and guaranteed reward right now for a chance of greater reward in the future - and you'll be able to see direct results of your actions on the whole company and your stake in it.