The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

Great products don’t stay simple by not evolving; they stay simple by continually improving their core value while removing features and paring back aspects that aren’t central to the core.

The perfect question is a key to clarity. It unlocks truth and opens minds.

Great teams are more than the assembly of great people. On the contrary, great teams are ultimately grown, not gathered.

Our aversion to obstacles, setbacks, disagreements, and other forms of resistance is a bit ironic, because this friction is what builds our tolerance for future friction. We expend so much energy avoiding friction rather than inviting and leveraging it. The old adage “Friction polishes stones” is true: Friction not only reveals character, it create

One of my favorite sayings from ancient times is “Wealth is ultimately feeling like you got your full portion.” When I finish a project, I aspire to feel full. And when I lay dying, I hope to look back on what I would consider a full life.

You also need a margin to mine circumstantial opportunities and explore the unexpected.

Contrary to logic, you don’t want to attract all of your customers right away. You want your first cohort of willing customers to be quite small so that you can communicate directly and provide an incredibly high level of touch. At the start of your business, you want to iron out the kinks. As you expand, you want to do so slowly.

Simple is sticky. It is very hard to make a product—or any customer experience—simple. It is even harder to keep it simple. The more obvious and intuitive a product is, the harder it is to optimize it without adding complication.

As a leader, you can’t always provide answers. And you shouldn’t, as the correct solution may still be premature. But what you can do is always add energy. This ability to turn negative conversations into positive ones is a trait I’ve always admired.