The Elevator: The Value Ladder, DNA Test, Debt.

"A leader is best when people barely know he exists."

Apr 25, 2025

The Elevator: Curated inputs to elevate your business and expand your lifestyle.

The Value Ladder: 5-Levels of Questions for Leaders

You’re buying shelves worth of “how-to” books, and they’re getting you nowhere. I had to wake up to that realization at a certain point after binging Lean Startup and other business “how-to books.” They weren’t doing anything for me. Or maybe just marginal improvements to my growth.

Consuming so much how-to content led me to see how ineffectual it was. Then, I was lucky enough to meet mentors who disrupted my thinking. They worked with me at higher levels of the game than what we see everywhere online which is commoditized, simplified instruction manuals that seem appealing yet rarely produce important results for you and your business.

When you meet a great mentor or teacher, you are drawn to them…More than anything, they challenge your beliefs. And you stick with them until they have properly disrupted your way of viewing the world.

Over time, I sought to grow myself by asking better questions, and I learned to grow others by asking them better questions.

I created a “question ladder” below that can help you with this process. Use these when seeking to ask better questions of yourself and others.

1. “What do I do?”

When you’re new or anxious, your mind searches for the next concrete step. This question is low leverage… If you live here, you are outsourcing to someone else your actions. If you’re asking this question, you’re probably procrastinating.

2. “How do I do it?”

How is a “Form” question. Many people can do the same action, but with different results. How you do something is important, as is the proper energy and integrity behind it. How is the biggest trap, which is fed by the endless scroll of how-to content. Ultimately, you always invent your own how.

3. “Who should do it?”

This is the first leadership question. This is where you graduate from operator to manager; hiring and delegating. A founder stuck in how often needs only to replace it with who. With “Who” your attention moves from you to others, and you start thinking about a bigger ecosystem beyond you, differentiating your skillset vs. that of others. “Who” is great for recognizing the limitations of yourself and others. These become useful constraints.

4. “Where are we going?”

Where is the “Systems” level question. Where is the question that changes everything else you do. “Should we go to the Moon, or go to Mars?” Each choice changes everything else about what’s done, by whom, and with what systems. You’ll note that “Where” has more risk than any of the above questions, and this is why it’s more valuable. Where takes courage because it means selecting a destination and sticking with it. Where creates the possibility of major failure, and therefore major success.

5. “What does it mean?”

The final level of value is around meaning. Meaning making is about how we interpret the events around us, and how we contexualize every other question listed above.

The highest levels are about context.

In meaning questions, you are playing with the container, not the contained. You start playing with the rules, the stadium, the field, not the game or players on the field.

Meaning-making is about storytelling. And as Steve Jobs said, “The most powerful person in the world is the storyteller.”

Lao Tzu wrote, “A leader is best when people barely know he exists… they will say: we did it ourselves.” The highest-level questions create containers where others thrive. They let you disappear while the system you designed compounds in the background...

Have a great weekend,

xx David

On to the links…

Nice looking at home DNA test. (Nucleus)
Profile on investor Graham Duncan, whose core focus in investing is identifying people.

“I didn’t feel like I had a comparative advantage in picking stocks or doing any number of other styles of investment. Instead, we built around what I happen to be good at—picking people.”
“I realized I was good at finding people who had access to a relevant information stream, and I developed a feel for how information leaks through a system.”
– Graham Duncan

Tyler Cowen, always the contrarian, on why the crowd against always being online has it wrong. The Case for Living Online. (Paywall, message me if you want to read, I can gift you the article). Counter post in the NYT.An Age of Extinction Is Coming. Here’s How to Survive.

Seeing a rise of apps that wouldn’t be built if not for AI/vibe coding. I expect we see thousands, millions more apps now because of that. Here’s one: “The App, Blue measures the shade of blue of the sky”

Now that we’re ending the ZIRP era, I’ve been digging more into the other side of the coin, debt. This series has been a good primer (The Value of Debt in Building Wealth, Amazon).