For a first round, you should almost always raise on a SAFE. It's fast, cheap, and you can collect money on a rolling basis without paying an attorney $25–50K to draft documents. Priced rounds add four to six weeks before you see a single dollar wired. You get the term sheet, you negotiate, and then you wait. For a first-time founder trying to hire people and start payroll, that's a problem.

Priced rounds also come with more baggage — board seats, investor control, oversight mechanisms that are just too premature at that stage. If an investor needs a board seat because they're worried the founder is green, they probably shouldn't be investing.

The seed round is where a priced round starts to make sense. If you're actually scaling and can attract a lead investor, do the priced round.

Here's why the timing’s important: post-money SAFEs don't dilute each other. If you raise $5M on a $25M post-money SAFE and then raise $20M on a $100M post-money SAFE, that second raise doesn't dilute your earlier investors. In a priced round, it would. They'd take 20% dilution.

Pre-money SAFEs are a different story. They do dilute each other, and they make a mess of the cap table. VCs don't like them. If you say you're raising $2M on an $8M pre-money (so $10M post), but you end up raising $4M, the post-money becomes $12M, and the share price shifts for everyone. You can just keep raising on it, which sounds flexible until it isn't. 

In addition, if you raise subsequent pre-money rounds that all dilute each other, the share price on the cap table starts to get complex for the various tranches and no one can forecast what they’re getting.

So: SAFE for the first round, priced for the seed. Post-money SAFEs if you're going that route. And the more experienced the founder, the less this friction matters — but for someone heads-down doing this for the first time, keeping it simple early is the right call.