It gets significantly easier as you raise more rounds. The presumption being that you're growing your customer base.
What it feels like overall:
Series A: you have your fingers crossed and beg investors.
Series B: investors compete on their valuations against each other, but you still doubt yourself a little.
Series C: investors have their fingers crossed and beg you.
You also experience less dilution in each round.
Series A: your metrics are still in its infancy and largely unproven (because you don't have scale yet).
Series B and C: you have found the right fit for your business model. Your metrics are more concrete and a clearer indicator of your future success.