These why-pay-later-when-you-can-pay-now fans of Roth IRA's always remind me of my client who did a substantial conversion from a 401(k) rollover IRA to a Roth IRA. He invested it in about 1,000 shares of a tech stock trading above $70 a share.  This was before the 2008 crash.  A couple years later it was below $10 a share.  Of course, back then it was predictable that the market would crash.  We know that's impossible these days.