Deciding if startup offer is the right move

[polar laurel]

I have been working the last two years on software for a small aerospace company, but recently decided to look around at what other options are out there. I recently got a great offer from a series C startup that ticks most all my boxes on paper: Good pay, unlimited PTO, remote work, and a technical concept I feel like I can get behind. They are about half the size of my current employer at about 50 people.

The issue is that I am a pretty risk averse person, which is compounded by being responsible for providing health coverage for my spouse while they are a graduate student. In this case, they are on a long term maintenance medication that without insurance and assistance from the drug company, would cost about $80k annually. As an added bonus, if they go off the medication, their body will likely adapt, meaning that it will no longer be effective even if they resume treatment, so suffice to say that interruptions to health coverage and income are something I am trying to avoid.

With that in mind, is it likely that any startup is going to be low risk enough for me to tolerate? How can I get a sense of that when they are a private company? I would also appreciate general insight from those with experience working in startups.

[lethal flame]

you might be able to have a conversation about this with the recruiter or hiring manager, but it gets into information that they might be hesitant to share. "my spouse is dependent on my benefits for a chronic condition" is a phenomenal reason to stay somewhere more stable, working for a startup does often entail switching jobs every 18-36 months due to changes in culture, team, projects…

once you have a solid career going in startups, getting a new job isn't such a challenge in most cases (though, come to think of it, those boom times may be changing — hard to say with everything that's changed in the past 2 years), but even then it would mean a lot of bureaucratic churn on insurance and coverage, and risks to things like, "my PCP is out of network on my new coverage"

you could try to gauge that by probing into the stability of factors important to you, but that also means understanding what's important to you and being able to articulate it clearly. you could ask about their attrition rate, how stable their projects are, what kind of customer lifecycles they have

[left wraith]

I've worked at a bunch of startups in different stages and one thing that's consistent is that things are constantly changing. While finding new jobs may not be difficult, startups tend to have relatively mediocre healthcare coverage meaning you still may be on the hook for a decent chunk of change. While I cannot make the decision for you, what I can say is that given the stakes of your situation, playing it safer with a stable company and a high quality healthcare plan will be less stressful during the hard times

[feral dust]

Usually you're going to have advance notice before you'd lose your job (in a startup way, ie layoffs or run out of money). When you do, there are ways to keep insurance for a while (though a pain). So I don't particularly see it as risky if you're paying attention to how the business is doing and where your position sits in terms of where layoffs would happen.

In any case, you should definitely plan out cash for the medication in your emergency fund. In a tax-advantaged account if you can.