For the Young Man Who Wants to be Extraordinary

Hey Friend,

Today, I’m sharing the insight I recently had into how to be massively ambitious (and therefore successful) without the stress.

I’ll give you a hint: It includes grandpas.

Let's get into it.

My Ambitions

I want to be extraordinary.

Maybe you can relate. Who doesn’t want to be special, right?

For me, ever since reading Elon Musk when I was 17, I've been aware of what can be done with this life (hint: it’s a LOT).

This pushed me to do extraordinary things. I built a business that allowed me to travel the world at a young age, competed in bodybuilding competitions, and did extremely well in a competitive university.

In my mind, however, all of this is just the start.

I've had a clear vision of becoming ultra wealthy ($100m+), an influential leader in the personal development space, the most impactful businessman in Hawai`i of all time, and other audacious goals.

All of this has served me well. Minus one element: Deadlines.

The Problem With Deadlines

The biggest mistake that I've learned in setting goals is attaching a deadline to them.

I want to make X amount by Y date. I want to lift X much by Y.

I recently set a goal to scale my business, Grow Your Ohana, to six figures in revenue by the end of the year. In my "vision board" for my life, I have "millionaire by 25" (2 years away).

These aspirations help in some way. They add a kick in the ass. An excitement. A "What if I actually did that?" glimpse of possibility.

But, in the end, they are pure stress.

They seep away any passion for simply doing the thing and turn everything into a means to an end.

They might even symbolize a subconscious comparison between you and someone else you know that did it in that time, or even shorter.

This is the double-edged sword of inspiration.

Mark Zuckerburg was a billionaire by my age (23). That's simultaneously a monumental inspiration as to what can be accomplished and a massive pressure to those who have a knack for comparison (yours truly).

The Solution: Grandpa Wisdom

All of this has led me to a realization: I need grandpa wisdom, not just older brother wisdom.

I have a lot of virtual older brothers: Tim Ferriss, Naval Ravikant, Ryan Holiday, Aubrey Marcus, Iman Gadzhi, etc.

These guys are great. They've taught me a ton, and I am deeply grateful for all of the content they've put out online.

But they're older brothers. The oldest, Naval, is 48. The youngest, Iman, is 22 (actually a younger brother, then).

I respect all of these guys for their efforts on learning from those beyond them, i.e. standing on the shoulders of giants.

But even the best of them cannot make up for the 25-50 years they haven't lived.

They will not have the perspective of a 90-year-old, no matter how many books they read and how much they listen to their elders.

This has given me a new idea: I will strive to primarily listen to the advice of those who are either above the age of 60, or dead.

Wisdom regarding the things that matter in life -- relationships, wealth, knowledge -- is not timely, it is timeless.

It makes no sense, then, to seek advice on these timeless principles from those who lack the perspective of a long life.

Grandpas Cure Stress

The stress to make money fast which overcame me after listening to young millionaires like Iman soon left me as I began reading Warren Buffet's Berkshire Hathaway Letters to Shareholders.

There is something calming about reading a book in which every chapter (~10 pages) signifies an entire year's passing. You witness the truth that good things take time (meaning possibly decades), and this is immensely relieving.

If you listen to any "wise grandpa" figure, he won't be telling you, "You better hit $10k/mo by next January!"

Instead, he'll say something like, "Work hard, be ambitious, but take your time and enjoy your life along the way."

These are the words of wisdom I need to hear, and maybe you do, too.

A few “grandpas” on my current list are: Ray Dalio, Kevin Kelly, Warren Buffett, Charlie Munger, Nassim Tabeb, Dewayne Noel, Robert Greene, and Steven Pressfield.

Also, people like Brett McKay (Art of Manliness) who are primarily curators of timeless wisdom have a slight exception to the rule.

There is something to be said for the relatability of a younger man’s interpretation of such perennial insight, but overall, I want to go straight to the source as much as possible.

That’s it. I hope you got something out of this week’s edition of “Letter to a Friend”.

As always, if anything in this email piqued your interest, shoot me a reply. I’d love to chat about it with you and see if we can’t both grow a little wiser.

Until next week,

Much love,
Ryan

P.S. Favorite Discoveries

What I'm listening to:

Sam Walton: Made in America by Founders. Sam Walton (founder of Walmart) is another grandpa who gives great advice on relentless excellence over decades. Much more focused on the process than the payoff. Listening to this pod episode has been simultaneously great entrepreneurial inspiration and perspective.

What I'm reading:

As mentioned earlier, Berkshire Hathaway Letters to Shareholders by Warren Buffett. I didn’t realize that Berkshire Hathaway was originally a conglomeration of mills making various fabrics and garments. However, due to its lack of profitability and overall stagnation, management (including Buffett) began to acquire other companies to diversify the shareholder’s returns. They started in insurance and banking and slowly expanded as those investments proved profitable. 60+ years later and Buffett is known as one of the greatest investors of all time. Another grandpa, and another reminder to be patient and simply try not to be dumb (see below).

A favorite quote:

"It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent."
- Charlie Munger (Warren Buffett’s business partner)