In the early days of FedEx, Smith had to go to great lengths to keep the company afloat. In one instance, after a crucial business loan was denied, he took the company's last $5,000 to Las Vegas and won $27,000 gambling on blackjack to cover the company's $24,000 fuel bill. It kept FedEx alive for one more week.[17]

Fred Smith wasn’t your typical rich kid. At the age of four, his old man dropped dead of a massive heart attack, leaving the young boy to grow up fatherless. Worst yet, Smith suffered from calcium deficiency disease. This weakened his bones, preventing him from playing sports, rough housing and enjoying physical activities.Longing for freedom,... See more

If I’m ever struggling to understand a business, taking a step back and saying “What is every party incentivized to do?” brings instant clarity. … When push comes to shove, Microsoft needs to defend their castle. They weren't defending it against a productivity upstart. They were defending it against an advertising company that was looking at it as... See more