Brian Sharples’ investing style traces back to a specific early failure—a storm that wrecked his used-car marketplace event at Candlestick Park—which left him deeply focused on risk management and led him to ask job candidates about their own failures as a way to gauge self-awareness. Having built HomeAway later in life, including negotiating founder exits before deals closed, he believes that hard-earned experience made him far more effective than he would have been as a younger entrepreneur, and he’s now known in the Texas startup community for generously mentoring other founders.