
Rise &Grind
Sponsored by Apple Card
🪄 529 goes stealth
Good morning and happy Sunday. The house with the white picket fence still exists, but it needs a new roof first. With home prices outrunning income growth, Gen Z buyers are settling for homes that need serious work (opens in a new tab). Move-in-ready is now a luxury, as the share of renters under 40 who can afford to buy fell from 56% to 37% between 2019 and 2024. Half of 2026’s first-time buyers say they’re fine with a fixer-upper, and TaskRabbit reports a ~40% surge in yard work requests. Welcome to the American Dream, hammer included.
Today, we've got a mixed selection of reads for you:
- Payroll taxes climbing: FICA has risen sevenfold since 1937 and could go higher
- 529s become retirement tools: Updated Roth rollover rules open up $35K for high earners
- Airlines expand to Europe: New transatlantic routes unlock cheaper fares to secondary cities
We've risen. Now, let's grind.
Top Idea

Most Taxes Have Fallen for Decades, but American Workers Are Paying More for One Tax — And Could Soon Pay Even More
For the last 70 years, taxes have fallen in the US (opens in a new tab)… but surprise: wage workers are almost single-handedly propping up one of the most important exceptions to the rule. And if history is any indication (opens in a new tab), they might soon see a bigger cut come out of their paychecks to keep it going.
The payroll exception: When seniors retire, they can count on Social Security and Medicare. Both are entitlement programs designed with good intentions — to help seniors afford a decent standard of living once they leave the workforce, financed by payroll taxes. But as the programs have grown to cover more Americans, the share of your paycheck going to Federal Insurance Contributions Act (FICA) taxes has risen significantly. There are two major components.
-
When Social Security was started in 1937, it was financed by a 1% tax on employees and a 1% tax on employers, with the rate raised 5x through 1965 as coverage expanded to more workers and disability insurance was introduced.
-
By 1966, Medicare was added to the FICA tax, bringing the total cost of these programs to 4.2%, which climbed further to 7.05% in 1985, 7.51% in 1988, and 7.65% in 1990.
-
Today, the combined 15.3% FICA tax generates $1.32T in revenue and covers nearly 81% of the programs’ total expenditures.
Even Your Fair Share Isn’t Enough
The FICA tax has not risen since 1990, but it’s increased sevenfold since the Social Security tax began. So by design, many retirees are now taking more out of the system than they put in (opens in a new tab). Costs currently exceed income, meaning the programs are drawing down reserves. That’s a problem that will need to be resolved soon.
- The US Government says that the Social Security trust fund has enough funding to pay benefits until Q4 2032 — after that, without changes, it could cover only 78% (opens in a new tab) of benefits.
- Congress has had to keep the system sustainable with broad changes — raising FICA taxes, broadening the wage base, and bumping the retirement age, among other things.
What does fixing the problem look like? Congress could fund Social Security indefinitely by copying what it did for Medicare — it removed the cap on Medicare-taxable wages in 1994 and added a 0.9% surcharge on higher earners in 2013. However, to prevent the further creep of FICA taxes, the government will likely need to look beyond payroll to fund other programs Americans rely on, like Medicare Parts B and D, Supplemental Security Income (SSI), and more.

Sponsored by Apple Card
Unlimited Daily Cash Back On Stuff You Needed Anyway
Whether it’s a new Mac for their first big semester or a new iPhone for yourself, you get 3% Daily Cash back on all your purchases at Apple using Apple Card.
And for other purchases, you can get 2% Daily Cash back when using Apple Card with Apple Pay.
- Apple Pay is available at over 85% of US retailers.
- Daily Cash never expires or loses value.
- It’s real cash (opens in a new tab) — unlimited Daily Cash on every purchase.
Apply now (opens in a new tab) for Apple Card, and you can use in minutes with Apple Pay (opens in a new tab) to start earning.
No bizarre points-conversion math required. Terms apply.
Wealth Planning
The 529 Account Becomes A Stealth Retirement Tool
Investors are increasingly using 529 education accounts as flexible wealth-building vehicles regardless of whether they have children. New rules allow up to $35K in unused funds to roll over into a Roth IRA, provided the account has been open for 15 years. That loophole is particularly valuable for high earners typically barred from Roth contributions. With expanded coverage now including certifications and professional training, the account serves as a tax-advantaged hedge for both career development and long-term retirement planning. [Read (opens in a new tab)]
Aviation Strategy
Airlines Expand Transatlantic Reach With New Routes
US airlines are racing to capture summer travel demand with their largest international expansion in years. United Airlines leads with 10 new destinations, while American Airlines, Delta Air Lines, and Alaska Airlines are deploying strategies from efficient Airbus A321XLR jets to new long-haul routes that unlock thinner, secondary European markets. These smaller aircraft allow carriers to serve cities like Porto and Olbia profitably. For travelers, that means a chance to lock in lower fares before demand picks up. [Read (opens in a new tab)]
Chart of the Day

Weekend Reads
⛽ McDonald’s Rewards can now save you more at the pump (opens in a new tab)
💰 Investors are pivoting toward companies that provide reliable cash returns (opens in a new tab)
🎟️ T-Mobile is giving away 1M Atmos Points to ten winners (opens in a new tab)
🖥️ Mac Mini finds a surprising new role in the AI boom (opens in a new tab)
✈️ Frontier is reshuffling how travelers earn elite status in 2027 (opens in a new tab)
🔄 Software stocks are bouncing back (opens in a new tab) as earnings ease AI disruption fears
✍️ Where to get documents notarized for free (opens in a new tab)
🏦 Sticky inflation and strong growth are complicating the Fed’s next move (opens in a new tab)
🩺 More self-employed workers could get access to cheaper health insurance (opens in a new tab)
Extra Grind
