From Jason Lemkin:
When a start-up should get acquired:
1. Before you fail / run out of money / etc. If you are slightly hot but with few revenues, or have something but not enough, sell while you still have time. Don’t wait until you have 30 days of cash. Way, way too many start-ups wait too long in this scenario.
2. When the team isn’t good enough. Even if you are growing nicely and even cash-flow positive, and all the quantitative metrics look good … if the team isn’t good enough, and can’t fix itself — sell if and when you can. Bad teams kill start-ups. Every day. Sell before then if you can’t fix it. Sometimes great individuals just don’t make great teams, and it can’t be fixed. It’s sad. But not uncommon.
3. When the economics, to everyone, exceed your magic number. I don’t know what your Magic Number is. But you will. It may be $19 billion. It may be $1 million. The Magic Number isn’t rational, really, and can’t be 100% explained on a spreadsheet. It is something that makes it all right. Sometimes, there is No Magic Number. Which is great, too.
(1) Re. “if the team isn’t good enough, and can’t fix itself”: Under what circumstances can’t you fix the team? From my experience at Seeking Alpha, fixing the team is painful and may take longer than you’d like. But it’s doable.
(2) Cf. When to sell your company — Ev Williams and When to sell your company — Ben Horowitz.