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So I have a Roth IRA brokerage account with Scottrade. I finally have enough savings (maxed standard employer 401k, emergency fund, etc.) that I'm ready to start investing some of my discretionary income into long term investments (beyond the 401k).

Currently, I have a sizable (to me) personal savings (outside of the Efund) investment in regular stocks but the benefits of tax free gains that the Roth IRA offer appeals to me so I want to max out the Roth IRA this year, but my only holdback is that if another more lucrative investment comes along I want to be able to tap the Roth IRA. Is that allowed?

Can I take out as much as I want from the Roth IRA at any time without penalty so long as I never exceed the max put into it per year?

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    If there is a lucrative investment opportunity, why not take advantage of it inside the Roth IRA? That is, if your IRA holds Stock A and you want to make an investment in Stock B, sell Stock A inside your IRA and buy Stock B instead. If you want to hold on to Stock A too (e.g. because it has appreciated), use your non-IRA money to buy Stock A outside the IRA while buying Stock B within the IRA. – Dilip Sarwate Oct 15 '14 at 15:18
  • Well I was thinking in terms of irregular investments (like angel investing)... I see your point though. – user20268 Oct 15 '14 at 15:25
  • "Yes, but." Websearch for "ROTH IRA WITHDRAWAL RULES" finds this and that, among others. There's another description of the "five-year rule" here – keshlam Oct 15 '14 at 15:30
  • @keshlam: "but" what? – user102008 Oct 17 '14 at 1:27
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You are permitted to withdraw the deposits from the Roth with no tax or penalty any time.

To Dilip's point, the Roth is a good place to keep the investment, and what you might consider is a 'self-directed' account. This type of IRA or Roth IRA permits a choice of investments that are not typically handled by banks or brokers, including Real Estate and the type of Angel investing you seem to be considering.

Note - the rules are tough, you need to be very careful to not be self-dealing, or dealing with certain related parties.

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    There is some nuance I want to point out in Joe's answer that is important. You are permitted to withdraw the DEPOSITS from the Roth with no penalty, but if you try to touch the earnings/gain you may incur penalties. – JohnFx Oct 16 '14 at 2:48

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