I believe 25% is the smallest discount I've seen thrown around, 40%-50% is rather common. As was mentioned elsewhere, smaller discounts tend to apply to shorte

I believe 25% is the smallest discount I've seen thrown around, 40%-50% is rather common. As was mentioned elsewhere, smaller discounts tend to apply to shorter horizons, such as when bridging immediately into a round. In those cases, they can be a good way for VCs to get on the cap table with prorata rights without having to muck around in series-A drama.