Peter Chiappinelli, portfolio strategist at GMO Asset Management, says that the market is showing similarities to 1999, which proved to be a great market opportunity that ended in a bear market. Chiappinelli says that every bubble has expensive stocks, but also some wild speculators -- people he calls 'the crazies' -- who are wildly speculative and bullish. They arrived about a year ago, Chiappinelli says, and it's a sign that the market rally has reached its final stages. Also on the show, Gene Peroni of Peroni Portfolio Advisors talks about why technicals show signs of a sideways, range-bound market for the summer, Josh Cohen, head of institutional defined contribution for PGIM, discusses the current status and future of retirement savings programs, and Chuck answers a question about short squeezes and whether investors should jump into them.