Q: Can I raise a series A round twice?
You can. But you need to be super transparent about it.
There are plenty of “A-1” rounds out there, and Series “B” rounds that really are a second A round. I.e., a round at the same price as last time.
It’s a flag for investors, no doubt. Every investor hopes for perfect, linear progress across rounds.
But many top start-ups also go through different patches and time periods. If you raised $5m in your Series A, struggled a bit, but now are doing better — maybe another $5m in an A-1 round at the same price can work.
Just don’t play too many games. Be clear on how much you raised before (don’t hide it), and how much you want to raise now.
And let the letters and name of the rounds work themselves out.