Man, I read a survey somewhere that said most people who get a big pay bump do it by switching jobs, not by waiting on their current boss to pay for training. Something like 70 percent of raises come from moving companies. I knew a guy at my old warehouse who begged for months to get forklift certs paid for and they kept saying "next quarter." He finally just paid the 200 bucks himself, got the cert, and left for a better gig two months later. The company that wouldn't train him lost him for 200 dollars. Your coworker is basically betting his whole career on a company being nice, and companies are not nice.