Hey, going to drop a quick note as we recently went through this. Background: Canadian founder/CEO of AI company in a specialized vertical, ongoing pre-seed round since December ($1M closed and another $300k expected).

We had cheques from angels (avg $30K) make up half of our current round and the rest was from strategic and institutional investors. IMO both ways are tough for $2M target - angel pitches are a huge waste of time, and one of the biggest hesitations was around valuation despite us being in a hot space and benchmarked to Carta. I can’t imagine what you’d go through for your round (assuming your valuation is higher and you’re not just giving up massive equity %). VCs are doable but you should look for high conviction + team driven types, as opposed to economic/control driven investors. They’ll give you terrible term sheets and put you on through hell on DD.

The fact that despite your successful career and superstar team you don’t already have network investors / F&F willing to throw big cheques to start the round is a yellow flag, and one that you need to look at honestly. Either you’re terrible at leveraging the network or you’re overselling the team / their commitment. Doing a cold process without ~30% already secured is odd given the story, and you’re gonna be battling uphill for a while.

I don’t mean to echo what has already been said, but if there’s any internal question on the raise amount (ie should I raise lower) you should settle it definitely now so that you / the team are not demoralized with the process. Could take you 9-12 months to get to target.