Analysis & Perspectives
Deep advice on tax strategy, equity compensation, retirement, and more.
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Your income probably isn’t as simple as it looks on paper. Maybe it’s a salary plus a year-end bonus that swings widely.
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FINANCIAL PLANNING
EQUITY COMPENSATION
TAX STRATEGY
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FINANCIAL PLANNING
Your income probably isn’t as simple as it looks on paper. Maybe it’s a salary plus a year-end bonus that swings widely.
FINANCIAL PLANNING
Sending your child to college is exciting, but it can also feel overwhelming. Tuition, housing, books, and fees add up quickly.
FINANCIAL PLANNING
Deciding whether to buy or rent a home can feel overwhelming. Do you go for the freedom of owning your own space or the flexibility of renting?
EQUITY COMPENSATION
Depending on your profession, equity compensation can represent a substantial portion of your net worth. In the tech world, it may be 30 to 60% or more.
TAX STRATEGY
How much your portfolio earns matters, but so does how much you keep after taxes. Tax-loss harvesting is one of the most common tools investors use to help manage it.
TAX STRATEGY
You’ve worked hard for what you’ve built. But there’s a question that nags at nearly every high earner: How much of this will I actually get to keep?
TAX STRATEGY
Most people who give to charity are not thinking about tax strategy when they write the check. It’s an act of generosity, after all.
TAX STRATEGY
Giving money or assets to a family member feels straightforward when you’re doing it, but on the tax side, it can be anything but straightforward.
EQUITY COMPENSATION
RSUs can look simple on paper. Shares vest, taxes are withheld, and you move on. In reality, the timing of vesting and sale can create tax outcomes that are easy to underestimate.
EQUITY COMPENSATION
For a lot of employees, the moment RSUs vest feels like a win. What is less visible at that moment is the tax bill that may already be forming.
TAX STRATEGY
Most investors who want broad market exposure buy an index fund or ETF and move on. But for investors with more complex tax situations, direct indexing has become increasingly popular.
TAX STRATEGY
Tax-loss harvesting is often viewed as a way to find losing positions and sell them before year-end to offset taxable gains. That framing misses most of what makes the strategy worth using.
TAX STRATEGY
A donor-advised fund (DAF) can be relatively simple to open, but the planning and strategy behind funding one requires more thought.
TAX STRATEGY
Direct indexing is increasingly being promoted as a tax-smart, customizable alternative to index funds. The idea is that, rather than owning shares of a mutual fund or ETF that tracks an index, you can instead own the individual securities directly.
TAX STRATEGY
The gift tax limit is often used to refer to the IRS annual exclusion, which is the amount a donor can give to a recipient in a calendar year without triggering a federal gift tax return filing requirement.
TAX STRATEGY
Section 1202 is part of the Internal Revenue Code and deals with the qualified small business stock exclusion, commonly referred to as QSBS. For those who own eligible startup equity, founder shares, or private company stock, it can enable them to exclude a portion of the capital gains from federal tax when those shares are eventually sold.
EQUITY COMPENSATION
How are RSUs taxed? The short answer is that RSUs generally have two tax moments: vesting and sale. At vesting, the fair market value of the delivered shares is treated as ordinary income.
AI & FINTECH
As seen on Forbes
Technology revolutions lead to a fork in the road: Do you use new tools to do what you already do, only cheaper? Or do you use it to do something customers never imagined?
EQUITY COMPENSATION
Incentive stock options and non-qualified stock options can look similar on the surface. Both give you the right to buy company stock at a set price.
EQUITY COMPENSATION
Private company employees often hear about 409A valuations when they receive stock options, but may not know why the number matters or what to do with it.
EQUITY COMPENSATION
Concentrated stock positions can build significant wealth, but they can also put too much of an investor’s financial future in the hands of one company.
EQUITY COMPENSATION
For early employees at a company that grows and eventually goes public, pre-IPO stock options can represent meaningful financial upside.
TAX STRATEGY
Two investors can earn the same pre-tax return and walk away with very different amounts of money. The difference is taxes.
EQUITY COMPENSATION
How are stock options taxed? The answer depends on the type of option you hold and when you exercise and sell.
EQUITY COMPENSATION
For many employees, executives, and founders, equity compensation is one of the largest wealth-building opportunities of their careers.
TAX STRATEGY
Taxes can mean the difference between a portfolio that looks strong on paper and one that actually lives up to its potential.
TAX STRATEGY
A taxable brokerage account is one of the most flexible ways to invest. There are generally no contribution limits, no retirement-account early withdrawal penalties, and no age-based restrictions on when you can take your money out of the market.
TAX STRATEGY
A taxable brokerage account offers something most retirement accounts do not: flexibility. There are generally no contribution limits, no retirement-account early withdrawal penalties, and no age-based restrictions on when money can be accessed.
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