Peter Thiel's $5 Billion Roth IRA, and What You Can Copy
How Peter Thiel built a $5B tax-free Roth IRA, and which parts of the strategy senior tech employees with early equity can actually use today.
Long answers to expensive questions.
Is Paying a Financial Advisor 1% Worth It? The Honest Answer
One percent buys very different work depending on who you ask. Here's what varies inside the number, and the questions that tell you which version you're being sold.
The 10 Equity Compensation Mistakes That Cost Tech Employees the Most
Avoid these 10 equity comp mistakes that cost tech employees thousands: ISO tax traps, option expirations, 83(b) windows, and more. With real numbers.
The Mega Backdoor Roth: How Tech Employees Maximize Tax-Free Savings
If your 401(k) allows after-tax contributions, the mega backdoor Roth can move tens of thousands a year into tax-free accounts. Here's how to know if you qualify.
QSBS for Startup Employees: The $15 Million Move
QSBS can wipe out millions in tax on startup equity, and it's not just for founders. Here's how employees qualify, and the timing that makes or breaks it.
The ISO Strategy That Lets You Change Your Mind
Exercising ISOs in January gives you eleven months to choose: hold for a qualifying disposition or bail out before AMT. Here's the strategy and math.
The Executive's Guide to Non-Qualified Stock Options
How non-qualified stock options are taxed, your choices when you exercise, and the planning decisions every NSO holder should think through.
Incentive Stock Option Taxation, From Exercise to Sale
How ISOs are taxed at exercise and sale: AMT triggers, qualifying vs. disqualifying dispositions, the dual basis trap, and recovering the AMT credit.
The Concentrated-Stock Guide to Donor Advised Funds
How tech employees use a donor advised fund to give appreciated stock, skip capital gains tax, and clear the new 2026 deduction floor. The real math.
The Tech Professional's Guide to Equity Compensation
RSUs, ISOs, NSOs, ESPPs: what each type of equity comp is, how it's taxed, and the decisions that move real money. A clear guide for senior tech employees.
The Tech Leader's Guide to Restricted Stock Units (RSUs)
How RSUs vest, why the 22% withholding rate falls short of your real tax bill, and how senior tech employees should think about sell-versus-hold decisions.
The Free Money in Your Employee Stock Purchase Plan
How Employee Stock Purchase Plans work, how the taxes treat your gain, and why 'hold for qualifying disposition' is often the wrong move. Run the numbers.
Equity Compensation and the Alternative Minimum Tax (AMT)
How the Alternative Minimum Tax interacts with ISOs and other equity comp: what triggers it, how the math works, and the credit most people forget to claim.