The decision point isn't when you raise the first round, it's when you decide not to raise a second one. You will have already spent a lot of time trying to build a big company and realized that isn't going to happen. Now it's time to figure out whether to convert your previously-ambitious startup into a stable, small company. Depending on the sector and business model, this may mean you don't even have to work that much. If you're selling SaaS and have low churn, you could hypothetically take it very easy and just pay yourself. VCs would not like this, and if you try to raise for a future company, funders would be wary for sure.