The Advantage #01: Living an asymmetric life, the Rothschild information edge, and why sleep still wins.

Welcome Note:

Welcome to The Advantage. This is a short, weekly note where I share what I am working on, something worth watching, a lesson from history, and one practical edge you can try right away. My goal is to keep it brief, consistent, and useful. No noise, no hype, just ideas and habits that compound over time in business and in life.

What I am Working On: 

This newsletter!

I have benefited enormously from founders, operators, business leaders, and writers who were willing to share what they were learning in public, often for free. This is my way of giving a little of that back.

My goal with The Advantage is simple. Keep it brief. Keep it consistent. Keep it useful.

Each week will follow the same format.

First, something I am working on. This will be an original piece of work or thinking from me, focused on my core circles of competence. Startups, building businesses, scaling, venture capital, and growth. No politics. No religion. Same rules as a good dinner table.

Second, something worth watching. This is my attempt to help filter signal from noise. One video, not five. Always tied to the same areas above. No movie or TV recommendations.

Third, a lesson from history. I am a big believer that history repeats itself. The past is often the clearest lens for understanding what is coming next. I will take a historic event and frame it in a modern application. Hopefully useful, but if nothing else, a fun piece of history.

Finally, one practical edge. Something you can try immediately. A habit, a tool, a piece of technology, or a small change that can give you an advantage.

If this gives you one or two useful ideas a month, it is doing its job. Try it for a few weeks and see if it adds value. If it does, feel free to forward it to someone who might enjoy it too.

Worth Watching

Quick intro:
This week’s watch is a 33-minute lecture from Graham Weaver at Stanford called “How to Live an Asymmetric Life.” Graham founded Alpine Investors, a private equity firm that has quietly built roughly $18 billion in assets under management. This is not internet motivation. It is a seasoned operator speaking to a room full of students who paid a ton of money for the privilege of getting to listen to him. You get it for free!!

What I loved about it:
There is nothing flashy here. No hacks. No secrets. And that is exactly why it is worth your time. The ideas are simple, almost obvious, yet they are the same basics that quietly keep people from building the life they actually want. It is a reminder that success in business and in life often comes down to a few basic concepts

Here is my 20-second recap if you do not have the full 33 minutes

1. Do Hard Things: If you want an exceptional life, you have to choose to do things that are genuinely hard. Hard things are frustrating. They take longer than you think. They usually look like a mess before they look like progress. Most people avoid or quit hard things. That is why most people stay exactly where they are.

2. Do Your Thing: You can build a great business in almost any category. The real constraint is not the market. It is whether you are willing to stay with it once it becomes slow, uncomfortable, or discouraging. And it will. The valleys are always deeper and longer than you expect. That kind of persistence usually only shows up when you genuinely care about what you are building. Life is too short to spend it grinding on something you do not believe in.

3. Do It For Decades: There are no shortcuts to being truly good at something. Real mastery comes from staying in the game long enough for compounding to show up. Everyone wants results fast. Very few people are willing to commit to a long-term horizon. That gap creates opportunity.

4. Write Your Story: Focus on the life you want to build, not just the problems you want to solve. Instead of complaining or worrying, shift your energy toward imagining what you want and then getting to work on it. Opportunity is everywhere, but it only opens up to people who act. Nothing beats doing.

Graham adds real color and examples to each of these ideas, and it is well worth the time.

Pro Move: You do not need to watch it. Put it on like a podcast and listen while you walk or drive.

Lesson From History: The Rothschild Information Edge

What Happened: In the early 1800s, the Rothschild family built the fastest private courier network in Europe. While governments relied on slow public channels, the Rothschilds received political and financial news days earlier, sometimes before events were officially acknowledged. That timing advantage allowed them to act while others were still waiting for confirmation.

Insight behind it: Their edge was not size or capital, although they would eventually have that as well. It was speed to understanding. They reduced the gap between what happened and what they knew, and that gap became their advantage.

Modern application: AI + data now serves as the courier network. Founders who use AI to compress the loop from event (data) to insight to decision to action will have a huge competitive advantage over those who don’t. This is no longer optional!

Practical Edge: Think of it as the new nine-to-five. Bed by 9 pm. Up by 5 am.

Why it works: There are a few simple reasons this works so well.

Most people need around eight hours of sleep. The easiest way to get it is by controlling when you go to bed, not when you wake up. Most of us already have fixed morning obligations. An earlier bedtime creates a buffer. Sleep is the foundation for health, clarity, and energy. Everything starts there. If you want to win the day, start by winning your sleep.

Most hours after 8 pm are low quality. TV, drinks, doomscrolling, half-attention conversations. By contrast, hours before 8 am are often high quality. Training, thinking, writing, planning. You are not adding hours to your day. You are trading low-leverage hours at night for high-leverage hours in the morning.

The data supports it:
Large population studies consistently show that high performers skew earlier than average. Research from the University of Toronto, the American Psychological Association, and the National Sleep Foundation shows that morning-oriented people tend to score higher on proactivity, planning, and goal persistence, all traits that matter in business and in life. A 2011 study published in Emotion found that early risers demonstrate higher self-regulation and greater persistence on long-term goals. Surveys back up what operators already know. Roughly 70 percent of senior executives wake up before 6 am, and Harvard Business Review interviews indicate that most CEOs wake up between 5 and 6. The common thread is not biology; it is priority. Early mornings create protected time for deep work, clear thinking, and intentional execution before the day begins to make demands.

How I use it:
I first started doing this while building Freshly. I noticed the strongest predictor of a good day was not what time I woke up, but what time I went to bed. I committed to being in bed before 9 pm on weekdays. Ten years later, that turned into lights out by 8 pm, and a 4:15 am wake-up.

Productivity is the name of the game, and this is the highest-return productivity habit I have found.

Try it for 30 days. You will thank me later.

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