Those new to trading can find uncertain markets between bull and bear markets daunting. Prices can fluctuate more than usual from day to day, and the volatility in the market increases the difficulty of wringing risk out of trades. Even a reasonably balanced portfolio can run into trouble when the markets get overly jittery. However, it's not impossible to protect your portfolio with trade insurance: options trading. Selling well-placed options on owned stocks can generate cash flow even if a stock is going sideways or even downward. The real kicker? Options selling does better during periods of high volatility. That's not to say you should start clicking all crazy-like in the option chain tab of your brokerage software, though. Like all trading, risk is still involved. There is a right way and a wrong way to trade options, and if you do it wrong (particularly with unprotected, or naked, options), the risk of a given trade increases, as do the odds of imploding your portfolio. With practice and training, options trading can be a consistent cash flow strategy even in uncertain markets. In this episode, Matt & Tim are joined by serial entrepreneur and trader Rance Masheck to discuss trading in uncertain markets both past and present, and Rance's wending path of financial entrepreneurship that lead him to founding the iVest trading platform. AND! Courtesy of Rance, you can check out the iVest trading platform for yourself with a special offer for Trading Justice fans. Just follow this link and fill out the form to get access to iVest.