Dear Financial Samurai,
When Tim Cook announced he was stepping down, I was actually excited. As a shareholder for around 20 years, I've grown tired of Apple's cash hoarding and lack of relative innovation. The last five iPhones have all felt essentially the same, and Apple still hasn't delivered on the meaningful AI integration they promised two years ago.
So as an investor, I expected the stock to pop. Fresh leadership, a highly motivated successor eager to prove themselves to shareholders — that sounded bullish to me. Instead, Apple sold off about 2%, so I bought more. I'm betting new leadership puts the company on a higher trajectory.
But then I caught myself. I had completely taken Tim Cook for granted. He took over on August 24, 2011, and Apple stock is up roughly 1,900% since. A $10,000 investment then is worth over $200,000 today, before dividends and taxes. Yes, Tim was handsomely rewarded and is now a billionaire. But my knee-jerk reaction to his departure reveals something very human: what have you done for me lately?
I feel this occasionally at Financial Samurai. Despite everything being free for 17 years, I still get criticized for not doing more, not covering certain topics, not responding fast enough, running ads, or pursuing corporate partnerships. It's a little annoying. But that's life.
It's worth being grateful to those who've helped us along the way. Because they won't always be around.
The Simplifying Continues
The higher the stock market goes, the more I find myself cutting costs and simplifying life. I think this is a response I baked in after the Global Financial Crisis. Everything looked rosy in 2007, and then it went to hell in a handbasket. I promised myself I'd never be caught off guard like that again. Prepare when times are fantastic, so you can spend freely when times are difficult.
That mindset is behind my latest post, “Giving Up My Sports Club Membership Despite The Health Benefits.“
It might look like a budgeting post on the surface, but it's also a life and investing post. One of the key takeaways: the consumer is much stronger than most people think, and that's a bullish indicator for your portfolio.
Being Rich and Resented Is Its Own Risk
One reason I started writing about Stealth Wealth back in 2009 and 2010 was the backlash against finance workers during the Global Financial Crisis. Even people who had nothing to do with the mortgage crisis got vilified simply for working in the industry. If you couldn't pay your mortgage, it was someone else's fault.
With AI, the stakes are orders of magnitude higher. If you work at a successful AI company, you may be wealthier than you ever imagined, at least on paper. But the more your company succeeds, the more livelihoods get disrupted. Millions of people losing their jobs tend not to feel charitable toward those who benefited.
Being rich while everyone around you is struggling and angry is not a comfortable position to be in. It creates genuine safety concerns, not just for you, but for your children. We are already seeing displaced and disgruntled people cause serious harm at their institutions. A larger reckoning may be coming. Please take this seriously and take care of yourselves.
Related: Be Safe and Live: Don't Work in AI When the Revolution Comes
More Motivation to Save and Invest
A few weeks ago I shared strategies on how to be more aggressive with your investments during a bull market. If you aren't financially independent yet, the time to build is now. Too many people splurge during the good times and get caught exposed when the correction hits.
One thing I'm increasingly confident about as we get older: your energy and drive to grind will fade. And what you'll want more than almost anything is peace and quiet. The problem is that peace and quiet costs money, whether it's a quieter neighborhood, a less stressful job, or simply having enough saved that you stop losing sleep over market swings.
Please think of your future self. Check out: One of the Best Benefits of Wealth: Buying More Peace and Quiet. Your older self will thank you.
It's All About Earnings Growth
I want to leave you with a thought on S&P 500 earnings. My price target for the index at the start of the year was 7,300, and I'm sticking with it. The main reason is earnings growth remains strong, despite elevated oil prices and ongoing geopolitical uncertainty.
Look at 2026 EPS revisions compared to the historical average from 2011 to 2025. The spread is significant. Even if those revisions get cut in half, they still outpace the historical average. That makes it hard to call this a bubble on the verge of bursting, especially when valuations are actually coming down.
Could we see another 5% to 10% correction as high oil prices work their way through the economy? Easily. But I don't see the conditions for anything much worse than that. I'm keeping my personal stock allocation steady for now.
To your financial freedom,
Sam
Millionaire Milestones turns one year old on May 6, 2026. Thank you for all your support. I hope you put the strategies to work and are meaningfully richer for it. Please leave a review if the book has helped you.
I'm wrapping up personal finance consulting sessions at the end of May, bundled with the book promotion. After that, I'm taking the summer off to finish writing my next book, Your Children Will Be OK. If you're interested in a session, sign up now and we'll find a time to connect.