I've done this with my last startup and also have seen this happen on two addition occasions with new employees putting in 6 figures each. 1. Funding is usuall

I've done this with my last startup and also have seen this happen on two addition occasions with new employees putting in 6 figures each. 1. Funding is usually open for employees to participate. Founders love taking money from employees rather than VCs. 2. VC's like this because the team is invested to win. No, they love this. 3. Be like a VC and be diversified. Don't put all your eggs into one basket. 4. putting in new bucks likely won't bump you up close to founder-ish levels of equity. 5. Timing has a lot to do with this. Don't force the issue if any tension arises that can take away from your core responsibility of doing a good job.