you'll probably love it until it doesn't work out. If it does fail - you will be infinitely more intelligent about all aspects of whatever business you are in, and if you are any good will be able to go find another job with some good material from which to draw from during interviews for your next gig. It shows you are willing to take risks. Take the money while you can get it, if it is indeed more and real.

I could share my crazy startup story but its really long winded, but yada yada yada, the owner/founder is in federal prison.

This.

I'm working with a startup that is backed by 2 of the largest companies in the world with a customer in place.

That would be a no brainer.

Also, as an engineer you're not necessarily going to get fired when if/they are acquired.

Keep in mind you'll work over 30% harder and probably 30% longer.

Does that increase afford changes in your families lifestyle?

When my kids were small I took about a 10% decrease in pay to work remotely. I was able to help get them ready for school, I was able to coach soccer, I was home for dinner every night.

It's not just about the job but moreso how it affects your entire life.

All that being said, it sounds like a great oppty.

What was the value and date of the last 409A that they are using to assign a strike price to the options, and how much liquidation preference is currently ahead of you on the cap table? There are easier ways to make a salary than working for a startup, so its good to understand what it will take to realize upside.

I've worked at a few startups. I love it.
Typically it's more hours, but a lot more engaging and fun. You get a lot more responsibility and control. Your contributions make a much bigger contribution to the companies success.

I'd try and find out how experienced the team is and the technical leadership, not necessarily the founder, but engineering management and the team as a whole. A lot of startups hire entry level or early career engineers and they really need a more experienced team. It becomes very chaotic.

Expect very fast changing corporate goals. The companies are usually still trying to find the optimal product-market fit, and feeling out the market. So objectives change often, avenues get explored, you investigate new ideas, and you learn for one reason or another why that idea won't work, or isn't practical because of time or budget pressures. Or you learn something new about customer needs and have to modify the product.

I have also worked as a contractor for well established mega-corps, and despite the chaotic environment of startups, I'd take it any day over the boring and old already established mega-corps.

You get to be a lot more creative at startups.

It's definitely more hours, but also more rewarding. I would avoid a team that is lacking experience. One startup I was at most of the engineers it was their first job or they were like 1-2 years experience, and they were all smart but really the inexperienced showed. I was a bit more experienced than the rest. Although I admit it was still worth the experience just a lot of chaos and things done inefficiently due to inexperience.

You also need to determine what runway you're comfortable with. For me it's typically 1 year. If I feel confident the company won't fold within the year and I think they're well positioned with their tech, then it's lower risk.

Understand there are typically funding milestones to unlock more investor dollars. Ask them what these are.

Also ask them what is the biggest challenges they see ahead. Ask them what parts of their tech roadmap they are struggling with the most or has the most uncertainty.


If you get to the offer stage here is what is standard. If it's different than this it's a red flag so ask why. Options are typically ISOs (incentive stock options, aka qualified for special tax treatment compare to NSOs aka non-qualified) with a 4 year vesting period, that has a 1 year Cliff for the first 25%, then the remaining are vested in equal parts monthly over the next 36 months (1/48th of the options each month). Make sure there are no claw backs or repurchase rights for vested options if you leave or are let go.

You'll also want to know your fully diluted share. So make sure to know the number of shares, the number of fully diluted shares of the company.


Just keep in mind the options are like lottery tickets, and they aren't liquid. They may never be if the company folds, or only after like a decade after the company scales. So they are a long term play. It's to keep good and early employees invested for the long haul with the chance at huge multiples.

Usually startups pay lower and use option and equity as justification, but in this case you're getting a big salary increase along with equity potentially so that's a big win in my opinion.

It's really case by case as to the long term stability. Companies can go a decade plus just fund raising. But your best bet is if they have customers already backlogged or at a minimum some kind of memorandum of understanding for making a purchase if the company delivers the products. Launch provider start ups are a good example. Relativity Space for example can raise money without a rocket because they built up a back log of customers who have agreed to purchase launches provided the rocket is built.

So ask them who are their customers are (or will be) and who they have already lined up and have agreements with.