One courageous quote
“There’s nothing worse than getting to the top of a ladder only to realize it’s leaned against the wrong wall.”
- Stephen Covey
One personal story
We’re living through unprecedented periods of employment and wealth creation in history.
On one side, things have never looked worse for many white collar jobs.
On the other side, last week delivered the largest IPO in history.
OpenAI and Anthropic are both expected to go public this year at valuations approaching a trillion dollars each.
SpaceX went public at a $2 trillion valuation.
That’s so much wealth that more than 4,400 employees became millionaires, with about 400 of them now worth over $100 million.
One story that stood out to me was the welder who started at $28/hour and walked away a millionaire because he took stock instead of more cash.
Read that again, welders and cafeteria workers at SpaceX became millionaires by having equity in SpaceX.
What if they had chosen more cash instead of stock?
Or what if they had chosen more stable employers instead choosing to work for an unprofitable startup?
They got rich by making the right bet that allowed them to acquire equity in an appreciating asset. That’s it.
So here is my takeaway for the week.
The best financial advice will never come from a financial advisor, because the best financial advice isn’t financial advice.
Here are 5 reasons why.
1. Financial advisors don’t help you pick a career or employer. Financial advisors optimize the income you already have. They don’t help you maximize your value in the marketplace. Big difference. To maximize your net worth you have to position yourself for maximum value in the marketplace. Look at the Forbes 400 list. How many public school teachers do you see on that list? Exactly. The career you choose is the #1 factor for building wealth. Nothing else comes close. Whether it’s leaving a job with capped earning potential, or joining a risky start-up, or starting your own company; if you want more upside, you’ll have to take more risk. And that requires courage. Financial advisors don’t help with that.
2. They do not touch your limiting beliefs. Success is 80% psychology and 20% mechanics. Anyone can teach you how to analyze a stock, underwrite a real estate deal, or price an option. But that’s not what matters. Mindset is. Why? Because fear and greed drive almost every money decision people make. The story you absorbed as a kid about money, risk, and what people like you are allowed to want runs quietly in the background of every choice. And financial advisors don’t help you with that.

3. They sell external investments, not internal ones. Stocks, bonds and index funds, are external assets. Your mindset, habits and skills are your internal assets. Those returns dwarf the market, and as Buffett notes, nobody can tax them or take them from you. He says the best investment you can ever make is in yourself, and he means it literally. As a young man he was terrified of public speaking. He paid $100 for a Dale Carnegie course to fix it. He says it changed his life. He keeps that certificate on his office wall, not his college diploma.
4. They have different incentives than you. Most earn through commissions and a percentage of the assets they manage. Few got rich picking their own stocks. They are paid to grow and protect a pile you already have.
5. They focus on defense more than offense. They are paid to help you play defense. Almost nobody gets wealthy on defense. Defense matters. It is just not where the life-changing money lives. The life-changing money lives in playing offense, not defense. There’s a reason why, The Millionaire Mind, based on one of the largest statistical studies of millionaires in America, dedicated a whole chapter to courage. Buffett built his fortune on a single rule: be fearful when others are greedy, and greedy when others are fearful. Stanley Druckenmiller says the great investors all share one habit. They make large, concentrated bets when conviction is high instead of spreading thin across 40 safe names.
Yes, your favorite financial guru is a hypocrite
One of the best books I have ever read was The Millionaire Fastlane by MJ DeMarco.
He pointed out that all the famous money experts in America didn’t make their money by following the advice they give us.
Think about Dave Ramsey, Suze Orman, Robert Kiyosaki and Ramit Sethi.
Now think about how they actually got rich.
Suze Orman didn’t build her fortune by dollar-cost-averaging into the S&P 500. She built it as a media machine. A number-one bestseller, 13 years hosting her own CNBC show, a PBS staple, a podcast, paid speeches. Her net worth runs into the tens of millions. She actually wrote a book literally called The Courage to Be Rich. Fitting title for this newsletter.
Dave Ramsey is the same story. He preaches budgets, envelopes, and a debt-free life. He earned $200 million by founding Ramsey Solutions, a media and education company. A radio show with more than 20 million weekly listeners. Bestselling books. Financial Peace University. Live events. The frugality is the message. The media business is the money.
Robert Kiyosaki wrote Rich Dad Poor Dad. It sold 40 million copies and built a fortune estimated near $100 million through books, seminars, a board game, and his media brand.
Ramit Sethi said he’ll teach us to be rich, but why isn’t he teaching us how to build a personal brand, write a book or land a show on Netflix?
The courage to move your ladder
In case it’s not clear, we are leaving a credential-based economy and entering a courage-based one.
In the previous era of a credential-based economy, you’d earn a degree, get hired by a big stable employer, and trade it for safety and a steady paycheck. Those days are coming to an end.
The credential-based economy was appealing because it provided us with a sense of certainty and safety. But for most of human history we were entrepreneurial. We were hunters, farmers, and traders who ate only what we had the nerve to go get.
Now we’re reverting back to a courage-based economy, one that rewards the people willing to bet on themselves, build a brand in public, start a company, risk rejection, unlearn old habits and learn new skills, etc.
In other words: the future belongs to the people with the courage to create it.
New opportunities are being built right now, and the years ahead will be better than any that came before.
The question was never whether the future will be brighter.
The only question left is whether you will have the courage to seize it.
One reflective question
Here's your reflection for the week:
Look at the ladder you are on. Is it leaned against the right wall? Trace it back to the beginning. Who actually picked that wall? What was your thought process when you chose that wall? Is it serving you?
One weekly challenge
Here's your challenge for the week:
Spend 30 minutes studying one career path or company that creates far more value than your current seat. Look at how the people there get paid and what skills got them in the door. You cannot move your ladder until you have scouted a better wall.
With courage,
Jonathan


