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If you choose to roll the stock over into a taxable account, however, you will only pay upfront taxes on the cost basis, the amount that you paid for the stock over the years.
FORBES: Company Stock Bonanza
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If Michael Dell were fair, say, like the man Warren Buffett is and has been to his shareholders, then Mr. Dell would allow existing shareholders to ROLL their stock into this deal just like Berkshire Hathaway permitted selling shareholders during its purchases of BNI (2009) and Wesco Financial (2011).
FORBES: Markets Rewind: Apple Cash Questioned, Dell Buyout Challenged And A Sixth-Straight Winning Week - Forbes
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However, if you roll over the stock into an IRA, the option is lost forever.
FORBES: Tap Into Employer Stock Without Paying Taxes (For Now)
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Once you've made your investment, there's no limit to how big the company can grow, how much you can roll over or how many times you can do a rollover--provided you can find another small-business stock to roll your gains into.
FORBES: Insiders' Tax Break
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If it was worth more, a borrower could pay off the loan and get the stock back, roll over the loan into a larger one or ask the stock be sold and take profits.
FORBES: Magazine Article
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It may be better to cash out the stock portion than to roll it into an IRA, since gains in employer stock are taxed at the lower federal capital gains rate, which now tops out at 15%.
FORBES: Tax-Free In the Rust Belt
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However demand for Facebook stock continued to roll in.
FORBES: Secondary Firm Made Aggressive Email Pitches For Many Private Tech Companies
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Just about a year ago, the stock market was on a roll and it appeared that the improvement in the economy was actually occurring ahead of schedule.
FORBES: Some Investors Concerned We Could Be Entering Another Soft Patch
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What if you could aggregate the top stock picks from the Forbes Honor Roll and build yourself a portfolio of ETFs instead?
FORBES: Dissecting The Forbes Honor Roll Using ETFs
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Yet, the stock market chooses now as the time to roll over into a potential correction?
FORBES: Position For Stock Market Correction, Hope You're Wrong
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"Rock 'n' roll has turned out to be a better investment than the stock market, " he crows.
FORBES: The Art of Grunge