Loan issue aside, I would advise almost everyone who isn't already "fuck you money" rich to not get too caught up on that extra 19% tax on income vs capital gains and just delay on exercising.<p>There are occasionally exceptions to this (involving a rare combination of the employee leaving and the company being as close to a "sure thing" as possible), but in the general case the risk/reward is so extremely out of whack that I can't imagine people would even consider exercising prior to the options becoming liquid if it weren't for the irrationally that comes into play when the money is going to the IRS.<p>There are just so many ways in which those options can become worthless (and a lot of them can happen even if the company is 'successful'): company goes out of business, company is acquired under terms unfavorable to common-stock holders, company dilutes stock to the point where your strike price is a joke, company actually IPOs but stock goes south of strike price due to massive selling pressure as lockup ends, etc, etc.