We write about the specific tax and planning questions that come up when your pay includes stock options, RSUs, or an employee stock purchase plan. You'll find worked examples of how RSUs are taxed when they vest and when you sell, explanations of the difference between ISOs and NSOs, guidance on when to sell or hold company shares, and our thinking on mistakes to avoid. Start with the topic that matches what you're facing right now.
How Are RSUs Taxed? A Kestrel Bay Retirement Advisors Walkthrough With Real Numbers
Kestrel Bay Retirement Advisors shows how RSUs are taxed at vest and at sale, with a 400-share example and the 1099-B basis fix. Read the steps.
Open the article →Sell or Hold RSUs? What Kestrel Bay Retirement Advisors Tells Clients
Kestrel Bay Retirement Advisors explains how to decide whether to sell or hold RSUs, with a cash test and a table showing vest tax is the same either way.
Open the article →ISO vs NSO Stock Options: What Kestrel Bay Retirement Advisors Tells Clients Before They Exercise
Kestrel Bay Retirement Advisors compares ISO vs NSO stock options: tax at exercise, AMT and withholding, with a 2,000-share example. Read the walkthrough.
Open the article →AMT on ISO Exercise: How Many Shares Fit Before It Bites (A Kestrel Bay Retirement Advisors Walkthrough)
Kestrel Bay Retirement Advisors shows how to find how many ISOs you can exercise before AMT applies, and when the AMT you pay comes back as a credit.
Open the article →When to sell ESPP shares: a Kestrel Bay Retirement Advisors walkthrough of qualifying and disqualifying sales
Kestrel Bay Retirement Advisors shows when to sell ESPP shares: $52 vs $12 of ordinary income per share, plus a break-even price. Request a lot review.
Open the article →Fixing ESPP Cost Basis on Your 1099-B: A Kestrel Bay Retirement Advisors Walkthrough
Kestrel Bay Retirement Advisors shows how to fix ESPP cost basis on a 1099-B with Form 8949, code B and a $3,000 worked example. Read the steps.
Open the article →How Much Company Stock Is Too Much? A Kestrel Bay Retirement Advisors Walkthrough
Kestrel Bay Retirement Advisors shows how much company stock is too much: a 50% drop at 40% of a $2M net worth costs $400,000. Read the rule.
Open the article →Exchange Fund vs Selling Stock: What Kestrel Bay Retirement Advisors Tells Clients
Exchange fund vs selling stock: Kestrel Bay Retirement Advisors compares lockups, fees and taxes with a $650,000 low-basis example. See the numbers.
Open the article →RSU Withholding Not Enough? What Kestrel Bay Retirement Advisors Tells Clients
Kestrel Bay Retirement Advisors shows why RSU withholding is not enough in the 37% bracket, with a $45,000 gap example and ways to cover it.
Open the article →Mega Backdoor Roth 401(k) and RSU Income: A Kestrel Bay Retirement Advisors Walkthrough
Is a mega backdoor Roth 401(k) worth it with RSU income? Kestrel Bay Retirement Advisors shows the $35,500 room math and which shares to sell.
Open the article →Backdoor Roth IRA for High-Income Tech Couples: A Kestrel Bay Retirement Advisors Walkthrough
Kestrel Bay Retirement Advisors walks high-income couples through the backdoor Roth IRA, with the pro-rata trap worked out in dollars. Read the 8 steps.
Open the article →Double-trigger RSUs at an IPO: What Kestrel Bay Retirement Advisors Tells Clients About the Tax Year
Kestrel Bay Retirement Advisors shows how double-trigger RSUs at an IPO can put $2 million in one tax year, what withholding misses and what to do.
Open the article →Leaving a Job With Unvested RSUs: What Kestrel Bay Retirement Advisors Tells Clients
Kestrel Bay Retirement Advisors shows the after-tax math on leaving a job with unvested RSUs, with a table and steps. Read it before you give notice.
Open the article →Exercise Options After Leaving a Job: A Kestrel Bay Retirement Advisors Walkthrough
Kestrel Bay Retirement Advisors shows how to exercise options after leaving a job: a dated 90-day checklist and cash-and-tax math. Ask us for a review.
Open the article →QSBS Exclusion for Startup Stock: What Kestrel Bay Retirement Advisors Tells Early Employees
Kestrel Bay Retirement Advisors lists the questions and records that decide the QSBS exclusion for startup stock. Read them before you sell. Request a review.
Open the article →83(b) Election for Early Exercise: A Kestrel Bay Retirement Advisors Walkthrough
Kestrel Bay Retirement Advisors explains the 83(b) election for early exercise: $5,000 at risk, $0 tax at filing, a 30-day limit. Read the table first.
Open the article →Selling Company Stock at 63: A Kestrel Bay Retirement Advisors Walkthrough of IRMAA
Kestrel Bay Retirement Advisors shows how IRMAA from a stock sale at 63 sets Part B at 65, with a $400,000 one-year vs four-year comparison.
Open the article →Selling Company Stock Over Multiple Years: A Kestrel Bay Retirement Advisors Walkthrough
Selling company stock over multiple years: Kestrel Bay Retirement Advisors shows a three-year bracket schedule and the price drop that erases the tax saving.
Open the article →HSA as a Retirement Account: The Triple Tax Math, Walked Through by Kestrel Bay Retirement Advisors
Kestrel Bay Retirement Advisors shows how an HSA as a retirement account adds about $37,700 over 10 years at 5%. See the math and steps.
Open the article →Questions to Ask a Financial Advisor for Tech Employees: A Kestrel Bay Retirement Advisors Walkthrough
Kestrel Bay Retirement Advisors lists the questions to ask a financial advisor for tech employees, with ESPP, AMT and Medicare examples in dollars.
Open the article →RSU Mistakes to Avoid: A Kestrel Bay Retirement Advisors Walkthrough for Vested Employees
Kestrel Bay Retirement Advisors explains RSU mistakes to avoid, with dollar costs: basis errors, short withholding, wash sales. Read the checklist.
Open the article →How Much Do I Need to Retire Early? A Kestrel Bay Retirement Advisors Walkthrough for Tech Employees
How much do I need to retire early? Kestrel Bay Retirement Advisors shows the $4 million rule at 45, 50 and 55, plus health costs. Read the math.
Open the article →When to Claim Social Security as a High Earner: What Kestrel Bay Retirement Advisors Tells Early Retirees
Kestrel Bay Retirement Advisors explains when to claim Social Security as a high earner who retired early, with break-even math. Ask us for a review.
Open the article →Kestrel Bay Retirement Advisors's Guide to a Year-End Tax Checklist for RSUs, ESPP Lots and Options
Kestrel Bay Retirement Advisors lays out a dated year-end tax checklist for RSUs and ESPP lots, with a $9,000 lot-choice example. Read it before December.
Open the article →Selling Company Stock Before 65: A Kestrel Bay Retirement Advisors Walkthrough of ACA Subsidies in Early Retirement
Kestrel Bay Retirement Advisors shows how stock gains raise income and cut ACA subsidies in early retirement, with a $10,000 vs $100,000 example.
Open the article →RSUs vs Stock Options: What Kestrel Bay Retirement Advisors Tells Candidates Comparing Offers
Kestrel Bay Retirement Advisors compares RSUs vs stock options after tax with a three-price table and a $150 crossover example. Read the walkthrough.
Open the article →Wash sale rule RSUs: What Kestrel Bay Retirement Advisors checks before you sell
Kestrel Bay Retirement Advisors explains the wash sale rule for RSUs, including the 61-day window, vest calendar and Form 8949 check.
Open the article →IPO lockup expiration: What Kestrel Bay Retirement Advisors says to do
Kestrel Bay Retirement Advisors explains IPO lockup expiration: what to do, with quarter, half and full-sale tax estimates. Build your plan.
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