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...

Hey Reader, Have you ever spent a whole day on something almost nobody saw? It's painful when the whole reason you worked hard was because you wanted to reach people. If you teach a workshop in person, you reach the 20 people in that room. But if you record that same workshop once, you can keep teaching for years on autopilot. This is the concept of leverage, and it's something I talk about in my upcoming book, The Ladders of Wealth (you can pre-order it now). A lot of people will look back...

Hey Reader, “But you’re a software company…” That’s what Tim Grahl said to me over dinner the night before Craft + Commerce a couple years ago. I had just walked him through everything we were about to announce from stage the next morning. Changing our name to Kit. Launching an App Store. Building recording studios for creators. The first two made sense to him. But the studios didn’t. Back in 2018, I pitched our team on physical locations for creators. I had a slide presentation and...