From 2001 to 2009, I worked at a private company in various roles, from marketing manager to director. Over my eight years there, I gained stock options from my hire date in January of 2001, to my last option grant in the fall of 2008. In addition, I purchased stock as an individual in 2005 and 2006. While we filed to go public in 2007, we eventually had to withdraw this plan, and the company never did see those options become public.
Last fall, after I joined Google, the company was finally acquired, for cash. I was given some payout from my time there, and separate investing, but due to many different rounds, up and down, numerous stock splits, and the CFO position being a revolving door, getting critical details, such as how many options came from which purchases, and the dates of the acquisitions have been almost impossible to figure out.
As you can imagine, this is big problem when it comes to filing taxes. TurboTax, or any reasonable tax professional, will need to know the details of when stock sold was acquired and for how much. But the third party company that managed working with stockholders doesn't have any records of acquisition dates or prices - only the number of shares per person and value of those shares. The CFO and financial team at the company (since acquired) doesn't have access to it either. My own records, mental or otherwise, aren't a perfect match, as the stock I acquired subsequently was reverse split and diluted, so the shares I purchased don't match those I was paid out on.
So this is a fun detective game of sorts, walking through my bank records (ever try to find a check for a certain amount from 6 years ago on Wells Fargo or eTrade?), and even emailing the law firm (Wilson Sonsini) which might have this data somewhere. All in the name of trying to be as truthful as possible so I can have the benefit of paying the IRS a good chunk of money which they are owed.
Had the company been a startup acquired in its first two or three years of life, like some you often read about, you wouldn't have the complexity of multiple rounds of stock, reverse stock splits, and the changes in financial team leadership. Had it been a public company, stock purchases would be easier to find, as would the stock prices. But the meandering road of a company that fought hard for a decade, before getting purchased, makes for messy records.
I am hoping I don't have to end up filing an extension (having never done so), but the deadline to file is fast approaching, and I still have gaps. It sounds like I should have made solid marble copies of those checks I made out to the company when buying my shares and locked them away in stone. If only everything was as easily searchable in the cloud as it should be.
/via my Google+ Profile