Similar to raising money, the best time to sell your startup is when you don’t need to or want to. Paradoxically, you are probably thinking about selling your startup as you are experiencing a lack of traction, tough competition, or difficult time fundraising. However, this is a bad time to sell your startup: you will have few bidders and be more likely to acquiesce to the demands of anyone who does show up.
The best time to sell your startup is when you have many options. These options don’t all have to be acquisition offers, they can also be venture term sheets for your next round. You might even be operating profitably and find yourself in the enviable position of confidently being able to turn down an offer. Usually, you will have these options because your startup is actually experiencing great traction; counterintuitively, the best way to “build to flip” is actually the same as building a successful company.