Here's how I'll think about it. Forget the options for a minute. Let's say you plan on being there for 2 yrs. 20k - (280*12) -5 = 11640 Option A = $11640 b

Here's how I'll think about it. Forget the options for a minute. Let's say you plan on being there for 2 yrs. 20k - (280*12) -5 = 11640 Option A = $11640 before taxes. ~$7000 after taxes. is $7000 after taxes going to matter to you? If you don't have those, would you be fine? If it matters then option A is looking better. Now look at the business fundamentals, you know these companies better, how long have they been in business. How much did they both raise in A & B rounds? B2B or B2C? B2B always, what's the number of customers they currently have? How's traction? Who are the competition in the industry? Who are the founders and C suites? How many employees, what's on glassdoor & blind? What's their tech stack? Any well known folks in the industry working there? This is a full day work of research, put it all together and see who looks likely to make it to the finish line? If A is more likely to succeed, easy, go with A. If B is more likely, then does that extra $7000 from A really matter? If not, go with B. If it matters, can you work some side gigs? 20hrs a month at $50 will get you the same $7000 at the end of the year? If you can work some side gigs, then B. If you can't work side gigs and need that $7000, can you downsize and give up some things? Nope? Then option A.