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Monday, November 2, 2026

EQUITY COMPENSATION • READ TIME: 12 MIN The $5.6 Billion Line: What Microsoft's 2026 Annual Report Means for the People Paid in Its Stock Withholding, hedging rules, reorganizations, and the ten weeks left in the year. For Microsoft...

Monday, November 2, 2026

BENEFITS • READ TIME: 10 MIN Open Enrollment Planning: A Practical Q&A Guide to Health Plans, HSAs, Ancillary Benefits & Life-Change Updates For many households, open enrollment is a rushed click-through in the middle of a busy fall....

Monday, November 2, 2026

BENEFITS • READ TIME: 9 MIN Health Savings Accounts: Your Triple-Tax Advantage A Q&A guide to a tax-efficient savings and retirement planning tool. Few tools in the tax code reward patience the way a Health Savings Account (HSA) does....

Monday, November 2, 2026

Career & Compensation Planning · 10 min read Microsoft's Voluntary Exit Offer: How to Decide Before the December Deadline About 60,000 employees received the same offer on October 26, 2026. There is no age or tenure requirement, the...

Wednesday, October 14, 2026

EQUITY COMPENSATION • READ TIME: 11 MIN After the Front Load: Planning Around GSUs That Pay the Most Early What a grant that pays most in its first two years means for spending, taxes, and savings. For senior Google employees with...

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Wednesday, October 14, 2026

EQUITY COMPENSATION • READ TIME: 12 MIN The Listing Is Not the Liquidity: What Employees of Late-Stage Private Companies Should Decide Before an IPO What employees of late-stage private companies should decide before an IPO, while the...

Wednesday, October 14, 2026

EQUITY COMPENSATION • READ TIME: 13 MIN The Year 3 Problem: Planning a Household Around Amazon's Uneven Pay Why the tax bill, the budget, and the portfolio all need to follow the vesting schedule. For senior Amazon employees with...

Thursday, October 1, 2026

INVESTING • READ TIME: 9 MIN Give the Shares — Keep the Cash A practical guide to charitable giving with highly appreciated stock Executive Summary Many generous households give the same way every December: they write a check. For...

Monday, September 28, 2026

INVESTING • READ TIME: 10 MIN The Concentration You Bought Back Why selling company stock for an index fund may not diversify a tech professional as much as it seems, and how to build a portfolio around your job Executive Summary The...

Wednesday, August 26, 2026

BUSINESS • READ TIME: 6 MIN Washington Saves Is Coming: What Business Owners Need to Know What Washington Business Owners Need to Know Before the State's Retirement Mandate Takes Effect — and How to Choose the Right Plan for Your...

Monday, August 10, 2026

RETIREMENT • READ TIME: 13 MIN The Risks That Make Retirement Complicated — and How Planning Answers Each Why Does Retirement Feel Harder to Plan Than the Years Before It? Saving for retirement is one goal. Living in retirement means...

Saturday, August 8, 2026

RETIREMENT • READ TIME: 14 MIN Designing a Retirement Portfolio: A Framework for What You Own, How It Produces Income, and the Order in Which You Spend It Why Start With Construction Instead of a Product? Most retirement conversations...

Saturday, August 8, 2026

CAREER TRANSITIONS • READ TIME: 16 MIN Laid Off, Not Retired: A Financial Playbook for the Involuntary Transition in Tech Why Does This Window Matter So Much? In a voluntary buyout, the runway is the equity they let you keep vesting...

Thursday, August 6, 2026

EQUITY COMPENSATION • READ TIME: 10 MIN Your ISOs and the IPO: A Practical Guide for Pre-IPO Employees Why Do These Decisions Matter So Much? If you work at a company like Discord or SpaceX and hold incentive stock options, the...

Wednesday, July 22, 2026

EQUITY COMPENSATION • READ TIME: 9 MIN A Planning Framework for Equity-Heavy Chip Employees Why Does Concentration in a Semiconductor Employer Deserve Its Own Conversation? If you are an engineer, architect, or senior individual...

Monday, July 6, 2026

TAX PLANNING • READ TIME: 9 MIN Understanding Your Stock Compensation: A Practical Guide to RSUs, PSUs, ISOs, NQSOs & Other Equity Awards Introduction Equity compensation has become one of the most common—and most misunderstood—parts...

Tuesday, June 30, 2026

TECHNOLOGY • READ TIME: 8 MIN The AI Stack Explained: How the AI Economy Actually Works — and Where the Bottlenecks Are Most people picture AI as one chatbot from one company. The reality is a twelve-layer industrial supply chain....

Thursday, June 25, 2026

RETIREMENT • READ TIME: 5 MIN Should I Do a Roth Conversion—and When? Many people understand they should save for retirement — but they don't always know the most tax-efficient way to do it. A Roth conversion is one of the most...

Wednesday, June 3, 2026

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Wednesday, May 27, 2026

Roth VS tradisional Retirement Contributions

Wednesday, May 27, 2026

Understanding RMDs And How Proactive Panning Can Reduce Their Impact

Wednesday, May 27, 2026

Real Estate As A Financial Asset:What Tech Executives Need to Know Before Holding, Optimizing, or Exiting

Wednesday, May 27, 2026

Getting Exposure To Pre-IPO Companies Like SpaceX:What Investors Should Actually Know About A Changing Private Market

Wednesday, May 27, 2026

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Wednesday, May 27, 2026

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Wednesday, May 27, 2026

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Wednesday, May 27, 2026

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Wednesday, May 27, 2026

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Tuesday, April 21, 2026

Are You Getting The Most Out Of Your Company's Retirement Plan?

Tuesday, April 14, 2026

5 Things business owners need to know

Tuesday, April 14, 2026

529s and UTMAsInvestment Accounts Commonly Used To Save For Children

Tuesday, April 14, 2026

How Do I Save For Retirement When All My Wealth Is Tied Up In My Business

Tuesday, April 14, 2026

How RSUs Work And Are Taxed

Tuesday, April 14, 2026

How Employing Your Children Builds Family Wealth

Tuesday, April 14, 2026

Understanding Washingtons Proposed "Millionaire Tax"

Tuesday, April 14, 2026

Helping Business Owners Choose The Right Retirement Solution

Tuesday, April 14, 2026

Tax Efficient Charitable Giving

Tuesday, April 14, 2026

Will I Have Enough To Retire?

Wednesday, March 4, 2026

Diversifying Concentrated Company Stock

Sunday, March 1, 2026

Retirement Is Closer Than You Think

Friday, February 27, 2026

The Mega Backdoor Roth

Friday, February 27, 2026

Retirement Plan Options For Business Owners

Friday, February 27, 2026

Velocity Of Employment Change And Layoffs In The Technology Sector

Friday, February 27, 2026

Managing Concentrated Stock For Technology Professionals

Friday, February 27, 2026

What Can I Still Do To Reduce My Taxes After December 31?

Friday, February 27, 2026

When DIY Investing Starts To Fail You