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Nathan Barry (@nathanbarry) knows better than anyone: Sometimes, you're working hard on something, and it's just not happening. How do you decide whether to double down, or shut down? This is what Nathan was asking himself two years after launching his email service, ConvertKit. He was bringing in only $1,500 a month, and he was losing customers every month. It was time to decide: Double down, or shut down. Today, ConvertKit brings in much more than $1,500 a month. They recently had their first million dollar month. Spoiler alert: Instead of shutting down, Nathan did double down. Today, we’ll analyze how he made that decision: When Nathan decided to double down, he had no idea if his business would succeed. How did Nathan – and his spouse – mentally prepare for the worst-case scenario? Nathan had to dig into his savings to the tune of $100,000 to double down on ConvertKit. What criteria did he use to know whether or not to quit. What was the one question Nathan asked himself that ultimately got him to double