I have 2 kids under 2 and I am working on 2 startups at once. That is basically like having 4 babies. I don't believe you should necessarily wait for the right time, for any kind of baby. There may never be an ideal time. If you have something you are passionate about you go for it. If you don't then you bide your time.
I have gone through periods of burn out and extreme passion about my startups. Sometimes it's nice to have a steady paying job and be stress free for a while. That's you biding your time until the right idea/opportunity comes along.
I went through an acquihire myself. Don't feel bad, startups are a longshot, and to see any positive outcome is much better than nothing. I worked for that company for 2 years, became frustrated, had an idea I was excited about, and then started something new.
So my advice is, take the stress-free job until you build up the passion to work on something new. And then do it.
Are those two actual startups, or more like two mirco "startups"? In other words, are you trying to get both of these startups to grow massively fast, or are these just businesses to cover your living expenses?
Sorry for the delay in response... I would call them actual startups.
For one I raised $1.7m in money over the years several years ago, but then had to scale it back due to lack of success. I pivoted it to a site that now has millions of visitors per month, but I run it solo trying to figure out how to make money and grow it.
The other company is just two us, my cofounder and I created a social media analytics platform and we have done about $150k of revenue in bootstrap mode in the past year or so. We are now trying to push a product to the masses and may look for funding soon.
This is not a definition of "actual" startups, just of those who have an imperative to grow "massively fast", usually because they have taken external, primarily VC, funding.
A startup is a new business that is still investigating what kind of product it is going to sell, and to which audience.
I have gone through periods of burn out and extreme passion about my startups. Sometimes it's nice to have a steady paying job and be stress free for a while. That's you biding your time until the right idea/opportunity comes along.
I went through an acquihire myself. Don't feel bad, startups are a longshot, and to see any positive outcome is much better than nothing. I worked for that company for 2 years, became frustrated, had an idea I was excited about, and then started something new.
So my advice is, take the stress-free job until you build up the passion to work on something new. And then do it.
EDIT: typo