I would suggest for this to work as a way to share risk, you would want to have a pool of companies whose returns are not correlated.
1. In a verticalized approach, your startup risk approaches your sector risk, if pool is large enough.
2. In a stage based pool approach (sector agnostic), risk is more diversified but rankings will be less meaningful. For ex, a rocket company founder may not be a good judge of CPG companies.
Does it depend on what you are hedging against, maybe? i.e. "my startup not being successful" vs "the economy tanking/oil prices trebling/whatever".
Even in a shock scenario, there are sector winners (see biotech and funeral homes in covid pandemic)