https://kestrelbayretirement.com/guides/ Tax-first retirement planning for tech employees en-us 1440 Thu, 08 Oct 2026 09:00:00 +0000 https://kestrelbayretirement.com/guides/how-are-rsus-taxed/https://kestrelbayretirement.com/guides/how-are-rsus-taxed/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/sell-or-hold-rsus/https://kestrelbayretirement.com/guides/sell-or-hold-rsus/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/iso-vs-nso-stock-options/https://kestrelbayretirement.com/guides/iso-vs-nso-stock-options/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors compares ISO vs NSO stock options: tax at exercise, AMT and withholding, with a 2,000-share example. Read the walkthrough. https://kestrelbayretirement.com/guides/amt-on-iso-exercise/https://kestrelbayretirement.com/guides/amt-on-iso-exercise/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/when-to-sell-espp-shares/https://kestrelbayretirement.com/guides/when-to-sell-espp-shares/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/espp-cost-basis-1099-b/https://kestrelbayretirement.com/guides/espp-cost-basis-1099-b/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/how-much-company-stock-is-too-much/https://kestrelbayretirement.com/guides/how-much-company-stock-is-too-much/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/exchange-fund-vs-selling-stock/https://kestrelbayretirement.com/guides/exchange-fund-vs-selling-stock/Thu, 08 Oct 2026 09:00:00 +0000Exchange fund vs selling stock: Kestrel Bay Retirement Advisors compares lockups, fees and taxes with a $650,000 low-basis example. See the numbers. https://kestrelbayretirement.com/guides/rsu-withholding-not-enough/https://kestrelbayretirement.com/guides/rsu-withholding-not-enough/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/mega-backdoor-roth-401k/https://kestrelbayretirement.com/guides/mega-backdoor-roth-401k/Thu, 08 Oct 2026 09:00:00 +0000Is 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. https://kestrelbayretirement.com/guides/backdoor-roth-ira-high-income/https://kestrelbayretirement.com/guides/backdoor-roth-ira-high-income/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/double-trigger-rsus-ipo/https://kestrelbayretirement.com/guides/double-trigger-rsus-ipo/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/leaving-job-with-unvested-rsus/https://kestrelbayretirement.com/guides/leaving-job-with-unvested-rsus/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/exercise-options-after-leaving-job/https://kestrelbayretirement.com/guides/exercise-options-after-leaving-job/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/qsbs-exclusion-startup-stock/https://kestrelbayretirement.com/guides/qsbs-exclusion-startup-stock/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors lists the questions and records that decide the QSBS exclusion for startup stock. Read them before you sell. Request a review. https://kestrelbayretirement.com/guides/83b-election-early-exercise/https://kestrelbayretirement.com/guides/83b-election-early-exercise/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/irmaa-from-stock-sale/https://kestrelbayretirement.com/guides/irmaa-from-stock-sale/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/selling-company-stock-over-multiple-years/https://kestrelbayretirement.com/guides/selling-company-stock-over-multiple-years/Thu, 08 Oct 2026 09:00:00 +0000Selling company stock over multiple years: Kestrel Bay Retirement Advisors shows a three-year bracket schedule and the price drop that erases the tax saving. https://kestrelbayretirement.com/guides/hsa-as-retirement-account/https://kestrelbayretirement.com/guides/hsa-as-retirement-account/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/financial-advisor-for-tech-employees/https://kestrelbayretirement.com/guides/financial-advisor-for-tech-employees/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors lists the questions to ask a financial advisor for tech employees, with ESPP, AMT and Medicare examples in dollars. https://kestrelbayretirement.com/guides/rsu-mistakes-to-avoid/https://kestrelbayretirement.com/guides/rsu-mistakes-to-avoid/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors explains RSU mistakes to avoid, with dollar costs: basis errors, short withholding, wash sales. Read the checklist. https://kestrelbayretirement.com/guides/how-much-to-retire-early-tech/https://kestrelbayretirement.com/guides/how-much-to-retire-early-tech/Thu, 08 Oct 2026 09:00:00 +0000How 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. https://kestrelbayretirement.com/guides/social-security-high-earner-retired-early/https://kestrelbayretirement.com/guides/social-security-high-earner-retired-early/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/year-end-tax-checklist-rsus/https://kestrelbayretirement.com/guides/year-end-tax-checklist-rsus/Thu, 08 Oct 2026 09:00:00 +0000Kestrel 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. https://kestrelbayretirement.com/guides/aca-subsidies-early-retirement/https://kestrelbayretirement.com/guides/aca-subsidies-early-retirement/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors shows how stock gains raise income and cut ACA subsidies in early retirement, with a $10,000 vs $100,000 example. https://kestrelbayretirement.com/guides/rsus-vs-stock-options/https://kestrelbayretirement.com/guides/rsus-vs-stock-options/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors compares RSUs vs stock options after tax with a three-price table and a $150 crossover example. Read the walkthrough. https://kestrelbayretirement.com/guides/wash-sale-rule-rsus/https://kestrelbayretirement.com/guides/wash-sale-rule-rsus/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors explains the wash sale rule for RSUs, including the 61-day window, vest calendar and Form 8949 check. https://kestrelbayretirement.com/guides/ipo-lockup-expiration-what-to-do/https://kestrelbayretirement.com/guides/ipo-lockup-expiration-what-to-do/Thu, 08 Oct 2026 09:00:00 +0000Kestrel Bay Retirement Advisors explains IPO lockup expiration: what to do, with quarter, half and full-sale tax estimates. Build your plan.