Plain-language thinking on wealth management, fiduciary planning, equity compensation, retirement strategy, and the decisions our clients face most often. Written by the Skyview team.
If you are an officer or director, or you hold shares from a private placement or acquisition, you can't simply sell whenever you like. Rule 144 sets the conditions. Understanding them early is what turns a stock sale into a schedule rather than a surprise.
Read Article →Resigning, retiring, or being laid off with vested incentive stock options starts a deadline most people learn about too late. Within roughly three months, you decide whether to exercise, how to pay for it, and how much AMT you can live with.
Read Article →Deciding when to exercise non-qualified stock options gets most of the attention. How you exercise matters too. The method determines how much cash you need, how many shares you keep, and how much of your net worth stays tied to one company.
Read Article →Every vest forces a decision, even if you never make one. Leaving the shares where they land is a choice to invest that money in your employer. A simple test helps: if the company had paid you cash instead, would you buy this much of its stock?
Read Article →Selling a low-basis position can trigger a large tax bill. A set of strategies lets holders borrow against shares, limit their downside, or receive cash up front while deferring a sale.
Read Article →Equity compensation makes income lumpy. A big vest one year, an option exercise the next, a large sale after that. Taxes are calculated one year at a time, but the decisions that drive them span several.
Read Article →Equity compensation generates more paperwork than almost any other kind of income, and the forms don't always agree with each other. The most common result is paying tax twice on the same income.
Read Article →Two households can own an identical mix of investments and keep different amounts of it. How to think about taxable, tax-deferred, and Roth placement — and when the decision matters less than it looks.
Read Article →A single form, filed within 30 days, can save a founder thousands in taxes — or backfire if the stock never pays off. How to think about the 83(b) election.
Read Article →Moved to Florida from a high-tax state? Florida has no state income tax, which changes the arithmetic of a Roth conversion — and the gap years and IRMAA shape the timing.
Read Article →Two employees can hold the same options and owe very different taxes. A plain-English guide to incentive vs. non-qualified stock options, the AMT trap, and when to exercise.
Read Article →Restricted stock units are withheld at a flat 22% — often far below your real tax rate. Here's how the under-withholding trap works and how to avoid a surprise IRS bill.
Read Article →The decisions you make in the three years leading up to a business sale shape the post-sale life that follows. A practical guide to what to put in motion — and when.
Read Article →For executives with significant company stock, a Rule 10b5-1 plan creates a rules-based schedule for selling — adopted in advance, executed without discretion. What the affirmative defense covers, and what it does not.
Read Article →A Health Savings Account is the only account in the U.S. tax code with a triple tax advantage. Here's how to transform yours from a healthcare account into a retirement powerhouse.
Read Article →A strategic approach to tax-efficient retirement savings — particularly valuable for high earners whose income exceeds traditional Roth IRA contribution limits.
Read Article →A new provision in the Secure Act 2.0 allows beneficiaries of 529 college savings plans to roll unused funds into a Roth IRA tax-free. Here's a complete guide to the five conditions you need to meet.
Read Article →Every relationship begins with a complimentary "Get Acquainted" meeting — no obligation, no pressure.
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