When I was in my first startup in 2002, I was trying to convince my boss Milan, the VP of engineering, to let me go to India and set up our offshore development team. I was 25 and had never worked outside the North America. Milan asked me if I’d ever failed at anything before. I said “sure, I’ve failed at exams, at getting some promotions, at getting into grad school etc” but he didn’t react and I felt like I didn’t answer his question correctly.