Hey Reader, What would you do if you knew you couldn’t fail? You’ve probably seen some version of this question before. It’s a good one, though sometimes the answer isn’t immediately obvious. That’s why I like Graham Weaver’s 8 questions for what to do with your life. Graham founded the private equity firm Alpine Investors, and he teaches at Stanford. In Chapter 2 of my upcoming book, The Ladders of Wealth, I credit him with a principle he shared with his MBA students called "worse first",...

Hey Reader, If I could solve only one thing in my business, that would have the biggest impact, what would that be? This is the question every great entrepreneur obsesses over. Rather than trying to do everything at once, you look for the bottleneck and focus on solving that. There’s a book called The Goal by an Israeli physicist named Eliyahu Goldratt. It’s a 1984 business novel that business systems nerds love. However if you’re not a business systems nerd you probably… won’t love it. It’s...

Hey Reader, Have you ever spent money on something and immediately felt guilty afterward? Will Guidara spends his money foolishly on purpose. And he thinks you should too. He once bought an entire barrel of whiskey and put it in his basement. He also put a skee-ball machine in the office. Is he going to get a monetary return on either of these things? No. But that’s kind of the point. He calls it the 95/5 rule: Manage your money and time like a maniac 95% of the time (no expense is too...