They were both selling their paintings for thousands and thousands of dollars. They both had commissions from wealthy buyers, and were working hard to keep up with demand. Every artist’s dream. So what changed?

To be in business is to take a risk. In a capitalistic society, success is not guaranteed, or even likely. 

Little things can add up over the course of a year. Especially if they’re mostly automated. 

Baseball has a truncated outcome distribution. When you swing, no matter how well you connect with the ball, the most runs you can get is four. In business, every once in a while, when you step up to the plate, you can score 1,000 runs.

My friend started a disc golf company that creates discs from 100% recycled material. Anyone who knows anything about plastics knows that this is a difficult thing to do. It’s a good thing my friend didn’t know anything about plastic.

There’s a tipping point in many decisions. If you’re wondering whether or not to do all the startup work for a new project you’re testing, just don’t. Get a few dry runs under your belt. It’s okay if it’s not a perfectly clean process.

I became aware of the idea of the $100,000 salary in 2005, and have held that number in my mind since then as a benchmark. Here’s the crazy thing. 2005’s $100,000 only has the equivalent buying power of $66,000 in 2023’s money.

“You’re better off with a great salesman and a mediocre product than with a masterpiece and a moron to sell it.”
–Herb Cohen

How much should your business spend on video content? In the age of the endless scroll, where a trending sound can get you 500,000 views, the answer is tough to calculate.

You know the feeling, right? Staring at the blinking cursor on the blank word document? Or fiddling around with a few video clips in an editing software, not getting anywhere because nothing looks cool? Feeling stuck is the worst.

I’m here to argue that video is becoming the new email. Not in a way that it will be used for daily communication, but in a way that if you don’t learn to use it, you’ll go extinct.

The old saying goes What would you do if you couldn’t fail? It’s a fine enough question, asking people to dream a little a bigger. Maybe it inspires people to face their fears, or suspend disbelief for long enough to see that something is possible. But I’ll ask you this: What would you do if you couldn’t succeed?

When we have a problem we look for the right answer. It’s easy to see the world as a binary choice between right and wrong, good and bad, smart and dumb. But anyone who has been faced with a difficult decision knows it’s not that simple.

Why are you being cheap? I don’t mean cheap, like, you’re resistant to spending money. I mean cheap like you’re resistant to charging money. Why are your services and products cheap?

Strategies are everywhere. But objectives are rare. And it’s ineffective to pick a strategy without knowing your objective.

If there’s skin in the game, people are involved. They’re engaged. They’re interested.

If you can swap out only a small portion of your entertainment time for education time, you’ll exponentially increase your value as an employee, or as a freelancer in the open market. Think of it this way: our skills and our knowledge are subject to inflation of information. Every year, technology makes our jobs easier, thousands of people gain the skills we already have, and the value of our knowledge diminishes.

Betting money on your strategy working? Bold move. But do you know what’s an even bolder move? Betting time on it. Betting emotional energy on it. Betting the chance that you might be wrong on it. This is much more difficult to do, because these are more valuable resources.

As exciting and compelling as it is to move to a big city, and make friends with all the big shots, and work with all the cool brands, it might not be the best way to run your business. I lived a quarter mile from Venice Beach’s Abbot Kinney, where all the hip new shops flock. I saw dozens of brands come and go in the years I lived there, spending fortunes on rent, and folding twelve months later.

I delayed getting married for years, in part because I waned to get my career in order before I did. As Kanye once said, “Just wait ’til I get my money right.” We did. When my wife and I were getting pre-engagement counseling, and talking with friends about the matter, I realized there was a flip side of this coin. There can be great financial benefits to being married.