The five-year holding period begins on January 1 of the year for which your first Roth IRA contribution was made or in which your first Roth IRA conversion was completed, whichever is earlier. So if you opened your first Roth IRA on April 15, 2009, with a contribution for tax year 2008, you will have met the five-year minimum on January 1, 2013. Vanguard vs. Fidelity vs. Charles Schwab | Stock Broker ... When you think about your investments, it's likely one of the first places your mind wanders is to your brokerage. For long-term investors with an interest in diverse, low-fee mutual funds and ETFs, Vanguard, Fidelity and Charles Schwab are three clear leaders.