&gt; Did it not ring a bell that a company that can&#x27;t give him cash but can instead offer compensation out of thin air in the form of options is in trouble?<p>This is not an accurate heuristic for &quot;how good is a company doing.&quot;  There are many legitimate reasons you&#x27;d want to pay someone in stock instead of cash.<p>&gt; And then there are the golden handcuffs were an employee is scared to leave because their options have too high a fair market value and their tax costs would be considerable.<p>This is definitely something to consider.  If your options agreement allows you to early exercise you can avoid all of the tax penalty and remove the golden handcuffs if you exercise immediately (before you have realized a gain) and file your 83-b with the IRS.  If it doesn&#x27;t allow early exercise you probably don&#x27;t want anything to do with it.<p>&gt; I recommend joining young companies that are willing to pay you a lot of cash for your exceptional ability and experience (execution is critical at this stage across the entire company from engineering to sales) and maybe take it easy on the option grants. Some stock is fun but don&#x27;t count on getting rich on it.<p>I&#x27;d recommend learning as much about business as possible, and consider working at a startup an investment, and you an investor.  If you aren&#x27;t comfortable investing then you shouldn&#x27;t be working in startups.  There is basically no reason to work at a startup if you aren&#x27;t favoring the equity ($, work-life balance, perks etc. are all going to be better at BigCo).