Generational Life > Generational Wealth

Count The Things That Matter.

This essay began as a search for “enough money”: the aspirational number that sits in an account like a middle finger to the world, letting you say no to expectations and yes to what you really want.

But in writing it, both Arjun and I came to the same conclusion: the pursuit of money is a fallacy designed to suffocate a life before it has even begun.

The only thing that matters is a vivid pursuit of life filled with the building of character, the challenge of friendship, the experiences of the world, the comfort of family, the full range of emotions (even the bad ones), the deepest relationships, and unreasonably unrequited love.

To bring in cliché early: money is but the currency of the game. Winning the game is what matters, not how many credits you can accumulate. Perhaps more aptly put is the saying about the destination versus the journey, wherein Arjun and I started this essay as destination maxis for our bank accounts, only to realize that our constrained time on this earth would feel empty if that stayed the case and that we better start focusing a bit more on our journeys.

So here we are, on our journey, enjoying it as best we can.

I hope you enjoy our essay about the pursuit of a generational life.

The Generational Life Matters

If money is only a means, then what does real wealth look like?

• Friends and family matter more. No one wants to be rich and alone. Solitude has its place, but joy compounds when it is shared.

• Health is underrated. Everything becomes fragile if your body or mind cannot support you, or if the people you love are not well.

• Character compounds like capital. Principles, opinions, and wisdom accrue over years of effort and discipline. In the long run they may be as valuable as money itself.

• Integrity is leverage. Whatever you do, do it wholeheartedly. Half-hearted work is worse than not starting at all.

True wealth is layered: money, relationships, health, character, integrity. Each one compounds. Each one can be lost. Each one is worth protecting.

With this essay thought we were searching for a number, a figure that would guarantee freedom. What we found instead was that numbers only matter in service of life.

To hold ourselves to that truth, we’ve written down five principles. They are our compass for the decades ahead: a reminder to pursue only the things that matter.

1. Real wealth is probably accrued over a lifetime.

Crypto produced some of the wildest success stories known to man. A guy sells his house and car to go all-in on Bitcoin in 2015, cashes out years later for billions. Or a memecoin gambler turns fifty bucks into millions overnight.

They’re real, but they’re rare. They go viral because they’re absurd, not because they’re common. And because they spread so well, they trick people into thinking everyone in crypto is getting absurd money absurdly fast.

The odds of it happening to you? Close to zero. Blame math. In life you can’t optimize for lightning strikes. If they happen, great. But you can’t live like they will. Making money is a skill and keeping that money takes even more effort.

You get better at it by doing the work: trying, failing, correcting, improving. Days, months, years, decades.

There’s no shortcut.

2. Your wealth, not theirs.

We’ve been told this since we were kids: don’t be jealous of what others have. But humans compare. Sometimes comparison pushes you to raise your game. More often, it corrodes. Especially in bull markets — someone’s always buying the house, the car, the watch, and you start to wonder what you’re doing wrong.

The problem is you’re not running their race. You’re running yours. Every mistake, every win, every trade is part of your story.

The antidote to envy is to stop keeping score by someone else’s numbers. Play your own long game.

That’s when wins actually mean something, because they’re yours.

3. Your emotional state is your biggest asset.

Children don’t think about the future. They’re present, absorbed, happy.

Adults can be on a yacht on Lake Como with family, everything perfect, and still sulk in the corner because the wrong bottle of wine got opened. The forest is there, but you’re staring at the trees.

Life will never be perfect. Something will always be off. If you measure happiness against an imagined ideal, you’ll always come up short. Contentment is a state of mind. Your emotional state determines not just how you experience life, but how well you play the game.

Protect it.

4. Less is more.

We live in an age of abundance. Infinite content, infinite options, infinite stimulation. The gift of the internet comes with a cost: filtering is now the scarce skill.

• Social feeds will amuse you to death, one reel at a time.

• Thousands of memecoins launch every week. Chase them all, and your portfolio trends to zero.

• Dating apps flood you with choice but erode your ability to commit.

When everything is abundant, the most important choice is what not to do.

Subtraction beats addition.

5. You, family and friends — that is all that matters.

The internet, social media, AI — they’re forces, not tools. And they’re making more people feel isolated than ever. People vent to strangers online but can’t tell their family “I love you.”

Real happiness hasn’t changed in thousands of years. Work on yourself. Spend time with people you love. Share life. Every dollar spent on a friend or family compounds into trust, loyalty, and memories. Those are the dividend-paying assets of life. The mistake is thinking you can delay this. “I’ll focus on them after I make money, after the career is secure.” But later never comes. Work never stops. Money is never enough. And meanwhile, the people you love move on, or disappear.

At the end of life, no one wishes they’d scrolled more or traded more. They wish they’d spent more time with the people they loved.

Ignore this, and you lose the only wealth that really matters.

Generational Money? A Myth, But Here’s the Math.

We began this essay with the goal of defining a number that is sufficient to retire and never work again — a term we are deeming "Generational Money." The amount of money that buys freedom, safety, and the option to take swings without worrying if you’ll end up homeless.

We did the math (and watched The Gambler). For most people, that number is around $3,000,000. If your portfolio grows at 5 percent a year, that’s $150,000. Pull out $100,000, pay tax, you’ve got $70,000.

• That covers an apartment.

• Groceries, some restaurants, entertainment.

• A car, health insurance, utilities.

• Even a vacation or a friend’s startup investment.

It’s a lot of money. Enough to never work again. Enough to sit on a beach in Thailand for thirty years if that’s your dream. Enough to start a company and swing hard while still having a cushion.

What we realized is that chasing that number is the ultimate trap. If the whole point of your life is to get to $XYZ so you can stop working… congratulations, you just optimized for boredom.

And the truth is, you don’t need $3M to change your life.

You can do it with $25K. Or $10K. Enough to move, quit a job, try something stupid, and maybe build something beautiful. Hell, you can even do this with $0, if you’re bold enough. If you are that full of life. That’s what we relized.

So yes, $3M exists as a kind of safety blanket. It’s nice to know the math.

But the whole point of this essay is that the math isn’t the point. The point is to actually live. Because the number will actually just hold you back -- to make you maximize for a job you hate or a situation that bores you or a relationship that isn’t quite right. Much better to act and figure out another path to money than to make the tradeoff of a worse life.

Generational Money should only serve the Generational Life.

If you’re living with good friendship, building character, compounding integrity, protecting your emotional state, subtracting distractions, and spending time with the people you love, the money will come.

And when it does, you’ll already know not to waste it sitting still and waiting for that yield to compound. You will be too busy making life compound into deeper and deeper experiences.

The real risk was never that you don’t hit some certain magical number. The real risk is that you hit the number and forget why you wanted to hit it in the first place.

Conclusion

What have I learned about wealth over the last few years?

The happiest moments I’ve had came when I treated money as a means, not an end. Burning money is sometimes the fastest way to make more memories, and even more money.

Money treated as a means is always tricky.

Having a good apartment, a good salary, or even some financial cushion can be quite the trap. Ironically, you’d probably be better at work, and at life, if you carried yourself like you already had enough and just went exceedingly hard at living in the moment.

And maybe that’s the final lesson: money comes easier when you treat it like a game and stop obsessing over hitting the number.

But the whole reason you treat it like a game is to get to the number in the first place. That’s the Catch-22.

You need money to survive. But if you live for money, you will never actually live.

Define the Money. Then Go Do Something Other Than Pursue Money.

- Kram, Jun