Short answer, from experience: unless the company is on a clear track to a liquidation event, no. That said I bought half the options of my last company becaus

Short answer, from experience: unless the company is on a clear track to a liquidation event, no. That said I bought half the options of my last company because the strike price -> FMV was great enough to take the risk. However I consider that a gamble equal to rolling pass line in Vegas, and I didn't make the bet with money I needed to live on.