Playing the Long Game, What Rome Can Teach Struggling Founders, and How to Learn Twice as Fast

Welcome Note:

Thanks for tuning into the third episode of The Advantage. 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.

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What I am Working On: A Blog Post

I just published a short reflection on the best career advice I received at 25 and ignored for years. It is about patience, compounding, and how optimizing for short term wins can quietly undermine long term progress. Here is an excerpt from the full 4-minute read.

The Best Career Advice I Ever Got at 25 (And Ignored for Years)

When I was 25, I left my job at an investment bank called Thomas Weisel Partners. I was young, ambitious, and impatient. I had just decided to go back and work with my parents in the family business, a move that felt uncertain and, frankly, a little uncomfortable at the time.

On my way out, my boss’s boss pulled me aside. His name was Ron. He had watched me for two years and understood my wiring better than I did myself.

He said, “Good luck with whatever you end up doing with your life. Just remember this: always be greedy long term and never short term.”

I didn’t fully appreciate how good that advice was in the moment. I do now. I think about it almost every day.

Early in my career, I wanted everything to happen immediately. Promotions. Raises. Validation. If I was doing good work, I wanted the reward now. I wasn’t wrong….

Worth Watching

Quick intro:
Jensen Huang built a trillion-dollar plus company, but still wakes up afraid it’s 30 days from going under. This week’s Worth Watching pick is a few weeks old, but if you missed it, watch it. Joe Rogan Experience #2422 features Jensen Huang, the co-founder and CEO of Nvidia, in a nearly two and a half-hour conversation about fear, failure, AI, and long-term thinking. He breaks down why he still runs Nvidia like a startup with no margin for error. He walks through the near-collapse during the company’s early Sega deal, shares his views on Trump, and lays out a vision of AI that’s both urgent and optimistic. It’s so good Rogan barely speaks.

What I loved about it:
Everyone is focused on Nvidia, as they should, but this episode reveals the mindset that built it. What stuck with me most was Jensen’s concept of Intelligence Abundance. He believes we’ve already solved Information Poverty, the challenge of accessing data. The new challenge is Intelligence Poverty, the ability to understand and use that data to make decisions. AI, in his view, is not a feature or a trend. It’s infrastructure. The steam engine of the mind. And it will lift the global floor. Despite leading one of the most important companies on earth, Huang credits much of his success to being a dishwasher and busboy at Denny’s. That’s where he learned urgency, humility, and how to serve others. Those lessons are still baked into Nvidia’s culture today.

Here is my 20-second recap if you do not have the full 2.5 hours, (Or check this week’s Practical Edge below to soon watch 50% faster)

• The "30 Days from Bankruptcy" Rule: Despite Nvidia’s massive success, Jensen operates as if the company is always on the brink of collapse. He argues that the moment you stop fearing your own obsolescence is the moment you become obsolete. For founders, "complacency is the silent killer."

• The Suffering Advantage: Jensen famously says he "hopes you have a dose of suffering." He believes that greatness isn't born from talent, but from the ability to endure pain and failure longer than anyone else. His "founder story" is built on the near-death experience of the Sega contract that almost bankrupted Nvidia in its infancy.

• Democratizing the "Super-Power": In the past, only the ultra-wealthy or highly educated had access to "intelligence" (researchers, lawyers, etc.). Jensen explains that AI solves this by giving every person on earth a PhD-level assistant. It turns every individual into a "manager of intelligence."

• Low-Skill Work, High-Value Lessons: Jensen credits his success to being a dishwasher and busboy at Denny’s. He argues that there is no such thing as "menial work", only work that teaches you how to serve others and move with urgency. If you can’t wash dishes with excellence, you can't run a world-class company.

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: Rome After Cannae

What Happened: In 216 BC, Rome got annihilated at Cannae. An army was wiped out. Allies started wavering. The obvious move was to negotiate and accept the loss. Rome refused. But they did not keep doing the same thing that got them killed. They stopped chasing a single decisive battle, conserved manpower, rebuilt forces, protected supply lines, and fought a slower war they could afford until their advantage returned. Side Note: If you are a history buff, this 1 hour documentary is pretty cool.

Insight behind it: When the math is wrong, doubling down is not courage. It is denial. Rome stayed committed to winning, not committed to the plan that was failing. They separated mission from method. That is what serious operators do when the unit economics do not work.

Modern application: If CAC is too high and customers are not reordering, you do not have a growth problem. You have a product problem. Do not buy more traffic to prove a story. Cut the spend that is hiding the truth. Narrow the customer, narrow the promise, and rebuild the experience until people come back without being bribed. Your job is to earn reorder, then earn scale. Stay loyal to the company, but be ruthless about changing everything that is making it untrue. Under twelve months of runway is enough time to fix it. It is not enough time to pretend.

Practical Edge: Speed up you listening

Why it works: Most people treat listening like reading, they think they need to catch every word. Seth Godin flipped that for me. In his conversation with Tim Ferriss on The Tim Ferriss Show, episode 138, he talks about listening for concepts, not syllables, and training your brain to keep up over time. That advice changed how I consume information. The goal is not to become a transcription machine or be able to repeat every word. The goal is to capture the model, the insight, the decision rule, then move on. When you do that, speed becomes leverage. You get the same ideas in a fraction of the time. 

The data supports it:
If you can move from 1.0x to 2.0x, you just doubled the amount of learning you can fit into the same calendar. If you can hold 2.5x on the right content, it is a different game. Also, this is not new hustle culture advice. Seth Godin has been teaching marketing and how ideas spread for decades, he is the author of Purple Cow, (and 22 other bestsellers) and he has always been unusually disciplined about inputs. It is not speed for speed sake but getting to a speed that feels fast but clean, where comprehension stays high.

How I use it:
I started this right after Ferriss published that Seth episode on February 10, 2016. That is just shy of a decade of reps. I did it the only way it works, slowly. I started at 1.1x, then 1.2x, then 1.3x. When it felt normal, I bumped it again. If something was dense, I dropped the speed. If something was story driven, I pushed it. Today, I rarely listen at 1.0x. Most podcasts live at 2.0x to 2.5x for me, and YouTube is usually somewhere between 1.5x and 2.0x, yes even video. The win is that my baseline has moved. I can now consume at least twice as much useful information in the same week, without adding hours.

Note: This is not for everyone. My wife loses it when she gets in the car and I have a podcast playing at 2.5x. She thinks I am nuts.

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