First startup went through three pivots before I chose to leave.
Second startup never pivoted.
Third startup is on the third pivot and I'm thinking it's time to leave.
After how many pivots do you chose to leave?
- Do I still have confidence in the executive’s team’s ability to decide on a sound strategy and align people in that direction?
- Is the organization healthy and are good patterns of communication, coordination, and execution being laid down?
- Does the product direction we are currently taking have a sensical business model it can possibly support?
The decision-making processes around the pivots and the way they were communicated can provide a lot of information to answer these questions.
Did any of your previous companies, that pivoted so many times end in success? Or were your exits worthwhile?
A startup job should be like any other job: you leave when what you're getting out of it (in terms of money, learning, satisfaction; likelihood of future reward; and whatever else matters to you) is no longer worth what you're putting into it (in terms of time; aggravation; opportunity cost; etc.)
Before that, startups need to build very cheaply and crudely. E.g. I wouldn't even build a database unless I'm certain I need one - in many prototypes, hardcoded data or dummy data works too. Once you get the first $1000, you can start scaling.
I've seen multimillion dollar companies start with an annual revenue of $10k. Startups always start slow.
To answer the question, you should have a good gutfeel for it. If you think the leadership is strong and the product is something people want, stay. If you're just in it because you think the market could be big, but your heart isn't into it, then leave.
Startups thrive on the outliers. There's not much process to it.
The idea being tried, and the team executing on it are probably much stronger predictors.
If you are already in doubt enough to ask, it's probably time to move on.
Why is it the case that doubts imply you should move on rather than doubts imply you should honestly investigate those doubts?