Last month, Tim Cook announced that he will step down as Apple CEO on September 1, 2026.
When Cook became CEO in 2011, Apple's market cap was $350 billion. Steve Jobs had just handed over the keys, and the prevailing opinion in the financial press was some version of: good luck with that.
Today, Apple is worth $4 trillion, equivalent in size to the economy of Britain.
If you owned Apple the day Cook took over and held until now, you would have seen a twenty-fold rise in your stock, adjusted for splits
That's an exceptional return. But realizing that return meant enduring some painful years along the way:
- 2013: Apple up 5% vs. S&P up 32%. Every financial pundit was writing the "Cook can't innovate" piece.
- 2015-2016: The Apple Watch had just launched and nobody was impressed. Stock underperforms the S&P 500 again, this time, two years in a row.
- 2018: Down again, underperforming S&P.
- 2022: After two big years, loses almost a third of its value.
And that's from one of the best stocks in the S&P 500. What about the worst?
If you held any of the bottom 20 stocks over that same time horizon, the best case is that you lost 4.5% of your money per year (Pitney Bowes, Western Union). Worst case? You lost everything (Sears, J.C. Penney, Peabody, Frontier, Chesapeake, etc.).
The good news is that you don't have to bet your whole portfolio on one stock to compound your money on the order of Apple.
The catch? Lengthen your time horizon.
If you were willing to invest over 30 years in an S&P 500 index fund, history says you'd earn roughly 10% a year—and turn $1 into $17. No stock picking. No betting on the right CEO. No stomach-churning years wondering if your one big bet is about to unravel. That's not quite a 20x return, but close.
$100,000 invested for 30 years becomes approximately $1.7 million. Not because you did anything clever, but because you did almost nothing—and you did it for a long time.
Good investing isn't about earning the highest returns. The highest returns tend to be one-off hits that can't be repeated. It's about earning pretty good returns that you can stick with, and repeating them for the longest period of time you can stomach.
Tim Cook's Apple was extraordinary at 20% per year. A 10% annual return in an index fund is ordinary.
But ordinary, compounded long enough, becomes extraordinary.
Here's what you need to know.
Markets
News & Notes
- Markets: Two months after the US/Israeli attack on Iran, the S&P 500 is back at an all-time high. The index moved up 10% in April, and the tech-heavy Nasdaq closed up 15% for the month. (CNBC)
- The Fed: The Senate Banking committee voted on Wednesday to advance the nomination of Kevin Warsh for Fed chair. Warsh wants to cut interest rates and shrink the Fed's balance sheet, but can he do it with inflation near 3%? (Barron's)Plus: Current chair Powell plans to remain on Board (CNBC)
- Tariff Refunds: After months of waiting, U.S. importers will finally have access to the $166 billion collected from tariffs that were ruled unconstitutional. On average, small businesses paid $306,000 in tariffs last year and need that money back—but the refund system is built in a way that favors those with the resources to navigate it. (Fortune)
- Interview with Sam Altman [Video]: OpenAI’s CEO sits down with Nicholas Thompson, CEO of The Atlantic, to discuss AI’s trustworthiness, its dangers, and its impact on young people. It's nerdy, but good. (Atlantic)
- Tax: Taxes for 2025 are done, but here's what to know for 2026. Decide whether or not to itemize deductions, adjust your withholding payments, or how your charitable giving could be affected. (WSJ)
- Plus: How to Deal with Rising Property Taxes (NYT)
- Business: When to Apologize to a Customer: In a recent field experiment with a food delivery company, researchers found that apologizing when customers are unaware of a failure can backfire—reducing satisfaction, trust, recommendations, repeat purchases, and revenue.(HBR)
- Travel & Spend:
36 Hours: Richmond, VA (NYT)
36 Hours: Santa Cruz, CA (NYT)
36 Hours: Queenstown, New Zealand (NYT)
(Pie)Chart of the Month
Greatest Entrepreneurs in U.S. History
(according to business historians and thought leaders in 2021 survey)
Firm News
New Hire: Welcome, Sarah Slattery, Head of Planning & Tax Strategy!
Sarah brings over two decades of financial planning experience to PieCapital, most recently as Senior Vice President and Wealth Strategist at Truist Wealth. Her credentials say it all: CFP®, Enrolled Agent, and Certified Exit Planning Advisor (CEPA)—a rare combination that covers the full financial lifecycle of a business owner, from tax strategy to exit. Sarah will work from our new Washington D.C. office starting in July!
PieCapital: Welcome, Sarah! Tell us what drew you to this role.
Sarah: PieCapital offered an exciting challenge where I can apply my experience to design a planning framework for new and existing clients, including a specialized program tailored to the unique needs and pace of business owners. I’m also drawn to PieCapital’s strong commitment to community impact, and after five years in the DC area, I’m looking forward to becoming more involved locally.
You spent a decade as a wealth strategist advising clients at a private bank. What's the most common planning mistake you've seen clients make?
A frequent mistake is not involving family members, particularly a spouse, in the planning process. While busy schedules often lead to dividing and delegating tasks, having both partners participate gives us the context we need to provide the best advice. It also helps future generations learn the “why” behind decisions and creates an opportunity to carry forward family values.
You recently spent two weeks in Norway. What was the highlight?
Creamy fish soup! This dish was at almost every restaurant and we ordered it every time--it was that good. And I love to cook so I will be trying to recreate this dish in the fall. Also, I would be remiss if I didn’t mention how beautiful Norway is with its green mountains and deep blue waters. It was an amazing experience and I can’t wait to go back!
Thanks, Sarah.
April Rebalance
Last month, all PieCapital-managed portfolios were rebalanced and traded to remain in line with risk/return objectives. PieCapital leverages BlackRock as an outsourced chief investment officer for the core portion of our portfolios, and complements those holdings with private capital, hedged equity, and dividend-focused equities to help retirees and near retirees maximize their income in retirement.
NAPFA Membership!
PieCapital is now a member of the National Association of Personal Financial Advisors (NAPFA), a leading professional association of Fee-Only financial advisors—highly trained professionals who are committed to working in the best interests of those they serve. Find out more here.
Get Your Tax Return Reviewed!
If you've already filed your 2025 return, great! Were there any surprises? How confident are you that you're taking advantage of all of the tax savings opportunities available to you in 2026?
Last year we added Holistiplan to provide tax return review to our suite of services for clients and prospective clients. You'll get answers to questions like:
- Are there ways to reduce my tax liability in 2026?
- What would be the impact of selling appreciated stock/real estate/business this year vs. next?
- Is my charitable gifting strategy optimized for my age and giving amount?
Here's how it works:
Current Client? Upload your tax return to our secure portal. We will review returns over the summer and use your return from last year to build a tax projection for 2026. You'll get a tax report and video feedback.
Prospective Client? Book a discovery call here to see if we may be a fit. If so, we'll provide a report and feedback so that you can plan for 2026.
Cate, Ben & Jack's Day Off.
Under the guise of a "very long dentist appointment," we busted out of school and caught the Durham Bulls' first day game of the season. They won, and Wool E. Bull signed the boys' sneakers. Go Bulls!
Not So Fast!
Another Tar Heel 10-Miler. Another slow ascent up Laurel Hill. Who puts a 3/4 mile hill at the end of a race?
And who's this flash of lightning? Christy and five friends knocked out a 75-mile relay race across central North Carolina. Caution: Feet blur at high speeds!
