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Darrow Wealth Management's title: Darrow Wealth Management | Fiduciary Financial Advisor | Sudden Wealth

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Should I Sell My Business? Find Your Number First
Key Takeaways Start by determining how much you’ll need from the sale to retire comfortably, as 70% of owners need to sell for retirement, according to a 2023 Exit Planning Institute study Clarify your goals, timeline, and financial needs before starting the process Consider your net proceeds from the sale, accounting for taxes, selling costs, and nonguaranteed payments, ...

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Sudden Wealth Syndrome and the Dos and Don’ts of Sudden Wealth
Key Takeaways Sudden wealth is any windfall big enough to change your financial life. It’s more about the impact on your financial circumstances than any specific dollar amount Sudden wealth syndrome describes the stress, guilt, or difficulty making decisions that some people feel after becoming wealthy overnight. Avoid sudden wealth syndrome by knowing what to expect and ha...

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Oura IPO: Equity, Tax, and Liquidity Planning

Oura publicly filed its S-1 with the SEC on September 3, 2026. Although the exact timing of the IPO isn’t public, Oura employees should prepare now because the tax impact will be real: time-vested double-trigger RSUs will be taxable as or...


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Anthropic IPO Planning: Tax & Liquidity Strategy for RSUs & Options
Summary: Pre-IPO Equity Planning for Anthropic Employees Anthropic employees should prepare for an IPO in 2026, as time-vested double-trigger RSUs will be taxed as regular income based on the stock price at the IPO. Standard tax withholding may not be enough Incentive Stock Options (ISOs) and Non-Qualified Stock Options (NSOs) have different tax implications, and employees s...

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RSU vs Stock Options: Taxes, Risk, Upside, and Which is Better
Summary: RSU vs Stock Options

Restricted stock units (RSUs) and stock options are very different forms of equity compensation. RSUs are awarded, whereas employees must buy shares if they have stock options. When RSUs meet all vesting requirements, the full value of the shares is taxable ordinary income – automatically. With options, virtually nothing is automated, so e...


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