Inherited $350 billion. Handed back $4.7 trillion. That’s $4.3 trillion of market value in 15 years. About $800 million a day.
And he did it as the first openly gay Fortune 500 CEO and being asked to follow Steve Jobs.
[Only Jensen Huang has created more market value as a CEO.]
There's a place for Tim Cook in the business hall of fame.
If Anthropic IPOs at a $2 trillion valuation
It will be 4x larger than all the IPOs in the history of San Francisco combined
When/if Anthropic, OpenAI, Databricks IPO
We are truly in for the mother of all booms in San Francisco and all that entails. The scale will have no precedent
3 thoughts...
1) The fact that nearly 1/3 of people checking the "Lost and Found" found retirement money that was theirs is a staggeringly high percentage, and highlights just how many people are likely to have forgotten about "old" retirement money. 💰️
2) As a matter of practice, along with suggesting periodic checks of unclaimed property at the state level, advisors should also encourage clients to double-check the Retirement Savings Lost and Found.✅️
3) I don't think I'll ever not find the name "Retirement Savings Lost and Found" beyond silly. Anytime I hear the name, I can't help but imagine someone's 401(k) sitting next to the lunch box and jacket I lost in 5th grade.🤪
"Of the 236,269 unique visitors who logged onto the Labor Department’s Retirement Savings Lost and Found Database from its launch in late December 2024 through the end of 2025, about 29.5% — 69,712 — found an old 401(k), pension or other workplace retirement plan associated with their Social Security number"
https://t.co/EzYj7fHtZl
This investing stat never ceases to blow my mind! 😳😳😳
How much can a diversified equity portfolio help you in retirement?
If you had $1M in 2000, needing $50k/yr plus inflation—
You WERE BROKE BY 2016 if you invested 100% in S&P 500!
If you instead invested in a (globally) diversified stock portfolio (with small cap & value exposure), you had $3.0M left—3x your starting amount!—in 2025, including almost $800k more annual spending from 2017-2025!
Share this with EVERY retired or soon-to-be retired person you know!
This sounds clean and confident. It’s also wildly incomplete - and for many people, actively harmful.
If investing were as simple as “buy VOO and chill,” average investors would actually earn market returns. They don’t. JP Morgan’s data shows investors consistently underperform the market by multiple percentage points per year due to poor timing, emotional decisions, panic selling, and chasing performance. Behavior matters more than asset allocation, and one-tweet advice ignores that entirely.
“Just hold the S&P 500” also assumes perfect behavior and zero recency bias. It sounds genius if you ignore the lost decade (2000–2010), periods when bonds outperformed stocks, and entire market regimes where diversification mattered more.
Every investor is different. Risk tolerance here is being completely ignored, it’s a function of time horizon, income stability, career risk, liquidity needs, family obligations, taxes, and psychology. A 25-year-old engineer, a 45-year-old business owner, and a couple 3 years from retirement should not run the same portfolio just because X likes simplicity.
The retirement “strategy” here is also dangerously oversimplified. “Market down? Take bonds. Market up? Take stocks.” That ignores taxes, sequence-of-returns risk, RMDs, Roth vs taxable drawdowns, Social Security timing, and asset location. Most financial mistakes don’t happen while you’re accumulating - they happen when you start withdrawing.
And the 1% fee argument misses the point.
A good advisor isn’t paid to beat the S&P. They’re paid to prevent catastrophic mistakes, coordinate investments with taxes and planning, design sustainable income strategies, and keep you invested when emotions hijack logic.
One bad decision can cost more than decades of fees.
Jason is a fitness coach selling his programming;
How silly would it sound if I said "nobody needs a fitness coach, just run 40 miles a week, hit two lower lifts, two upper lifts, and be in a caloric deficit for most days!" Ridiculous. There's obviously significantly more nuance to the fitness space that requires attention to detail for each specific individual (injuries, experience, goals, etc.)
I’ve done Olympic Weightlifting, Hyrox, Ironman, 100 mile ultra, marathons, HYROX, Crossfit, you name it.
I still pay for programming in both the lifting and running space (lifting shout out to @DeanTTraining). Not because I can’t “skate by” on my own - but because expertise removes blind spots and optimizes outcomes. DIY works… until it doesn’t.
Simple isn’t wrong. Incomplete is. And confidence isn’t the same thing as correctness
Low-cost indexing is great. Diversification matters. Behavior matters more. Planning matters most.
Think celebrities have their estates perfectly handled?
Think again.
Here are 9 famous cases that drop some surprisingly practical lessons for the rest of us…
🧵
Ten things I believe about money:
1. Money is emotional long before it is mathematical.
2. The biggest risk to your wealth (in good markets and bad) is you.
3. Anxiety adjusted returns matter more than absolute returns.
4. Good advice is not about prediction. It is about preparation.
5. Money without meaning will never feel like wealth.
6. Most financial mistakes are applying an old story to a new problem.
7. Your "normal" with money isn't; you only learn how weird you are as you mix it up with other people and see more of the world.
8. Environment influences financial behavior far more than willpower.
9. Advisors do their deepest work in the realm of humanity, not finance.
10. Money tends to follow identity, not the other way around. Fix yourself and you'll fix your money.
I just spent four days in the Teton Mountains helping lead a @Tribefounders retreat in Jackson Hole, WY, alongside my friend and TRIBE Founder, @trentjhughes.
Together, we brought eleven entrepreneurs into one of the most beautiful settings imaginable for a few days of deep work, honest conversations, and much-needed connection.
We workshopped.
We ate and drank.
We laughed until it hurt.
...we even had a surprise visit from a moose that reminded us we were guests in his mountains.
But what really made it special wasn’t the view (although breathtaking).
It was the people.
Entrepreneurship can be lonely, even when things are going well.
But it doesn’t have to be.
Over the last four days, I watched leaders open up about their struggles, push each other to grow, and cheer each other on in ways you rarely see in business.
The vulnerability was real. The breakthroughs were powerful. And the ROI (both personal and professional) was undeniable.
Eighteen months ago, Trenton sent me a DM asking for help growing this group. That single message led to one of the most meaningful professional partnerships of my life and to a community I’m proud to help lead.
If you’ve been searching for your people the ones who truly get what it means to build, lead, and live at full tilt, I’d be honored to introduce you to my TRIBE.
Until next time, TRIBE...
Grateful to lead with you and for you.
@WilDublin@TS_Secrets@MikeCalcara@Glynnfleet
Wayne Hippo
@albert_steed@michellepencz@camsberry
Pierre
The S&P 500 is down 12.1% over the last 4 trading days, the 12th biggest 4-day decline since 1950.
What has happened in the past following the biggest 4-day declines?
Stocks moved substantially higher over the next 1, 3, 5 years every time.
https://t.co/l5IYmkf6Ih