Articles for people paid in company stock.
Longer pieces from the newsletter years, on equity compensation, taxes, investing, retirement, and the life the money is for. The letters are shorter.
Start with your date
- Your company is being sold for cash. Before Your Company Is Sold for Cash
- Your company is being sold for stock. Before Your Company Is Sold for Stock
- Your company is going public. Before Your IPO Lockup Ends
- An offer to leave. Before You Answer a Buyout Offer
- Shares vesting this year. Before Your Next Vest Date
- A tender offer or secondary sale. Before Your Tender Window Closes
- The money already landed. After the Money Lands
- Your job is ending. Before Your Last Day
Not sure? Start here.
Jump to: Equity compensation · Investing · Retirement and planning · Money and life
RSU Concentration Risk: The Trap High Earners Miss
The tax doesn't disappear when you hold. It waits. Why concentration in your employer's stock is doubling down, not diversifying.
Sell or Hold Your RSUs? The Tradeoffs After Vesting
Vesting triggers the tax either way. Selling or holding after that is a question of risk and plan, not taxes alone.
High Income Isn't Wealth: Stop Gambling on Company Stock
Earning a lot doesn't make you wealthy. Company stock, volatility, and lifestyle creep are where high earners lose ground.
Overconcentration: Too Much Wealth in One Company's Stock
RSUs pile up, ESPP shares accumulate, and suddenly most of your net worth rides on one stock. How to unwind it without panic.
7 Tax Strategies High Earners Should Set Up Early
Seven tax moves that reward people who start early, from Roth conversions to 529 superfunding. Waiting is the expensive part.
Concentrated Stock Risk: What Happens When You Don't Diversify
Many people don't think about diversification until it's too late. What I've seen happen to people who held too much company stock.
Concentrated Stock Risk: What NVIDIA's 17% Drop Teaches
Even a great company can fall 17% in a day. If your net worth rides on one stock, that's the lesson.
When Your Company Goes Private: What Happens to Your Stock
A buyout that takes your company private cashes out your vested shares and puts your unvested equity in play. What to ask and how to handle the payout.
RSU Basics: How Restricted Stock Units Work and Get Taxed
What RSUs are, when they're taxed, and why your vested shares deserve the same scrutiny as a cash bonus.
Do the Rich Pay Taxes? Why High Earners on Salary Pay So Much
High earners on salary carry a heavy tax load. Why the myth persists and what planning can change.
What Happens to Your RSUs and Options in a Merger or Acquisition
Cash deal, stock deal, or hybrid: what each means for your RSUs, options, taxes, and career when your company is acquired.
Concentrated NVIDIA Stock: Risks, Taxes, and How to Diversify
Big NVIDIA gains are worth celebrating. A plan for the concentration risk is worth more.
Evaluating an Investment: Where Most Mistakes Start
People buy the story and skip the fundamentals. Risk, time horizon, exit, liquidity, fit: ask these before you commit.
Michael Burry’s Nvidia and Palantir Bet: Play Your Own Game
A 13F is a backward-looking snapshot. You don't know why anyone made a move, so anchor decisions in your own plan.
The Problem With Target Date Funds for High Earners
Your 401(k) default fund doesn't know your income, your RSUs, or your timeline. Here's where the glide path falls short.
Emotional Investing: How Fear and Greed Undermine Your Plan
Emotions are terrible financial advisors. Why you buy high and sell low, and five habits that break the cycle.
Investing in Your Own Industry: The Bias You Don't Notice
Tech people buy tech. Biotech people buy biotech. Why the industry you work in shouldn't decide where your money goes.
Investing Through Market Cycles: Proactive vs. Reactive
Bull markets make everyone feel smart. The test is what you did before the downturn. Proactive beats reactive.
Flexible Investment Strategy: Why One Approach Isn't Enough
There's no single right way to build wealth. The costly mistake is locking into one belief and closing off everything else.
AI Stocks and the Dot-Com Bubble: How Not to Repeat 1999
The internet changed the world and many internet stocks still went to zero. What that means for AI investors now.
The Real Cost of Real Estate: A 30-Year Ownership Example
An $800,000 property can cost around $2.2 million over 30 years once you count everything. The math, and the landlord reality.
Why a Bull Market Doesn’t Make You a Great Investor
Making money in a bull market isn't a strategy. What discipline looks like before the music stops.
Behavioral Biases in Investing and How to Take Back Control
Loss aversion, overconfidence, and the herd shape your money decisions more than you think. Here is how to counter them.
Make Your Money Work for You: Five Steps for High Earners
Earning it was the first half. Keeping it and growing it is the second.
Risk vs. Volatility: Why the Difference Matters
Volatility is movement. Risk is not reaching your goals. Don't confuse the two.
Stock Market Anxiety: How to Handle a Downturn Calmly
The market drops. That's not a crisis. Selling at the bottom is.
How High Earners Build a Seven-Figure Portfolio That Lasts
Income isn't the constraint. A plan you actually follow, every paycheck, is.
Investing in Tech Stocks Without Betting Your Future
Tech moves fast and swings hard. A look at volatility, concentration, diversification, and keeping your head.
Concentrated Stock Positions: What Can Go Right and Wrong
One stock built the Apple and Amazon fortunes. One stock also sank GE and Blockbuster holders. How to think about concentration.
Financial Planning Is About Decisions, Not a Document
A plan is useless if it doesn't improve your choices. Know yourself, respect your partner, understand risk and taxes.
Longevity Planning: Healthspan, Wealthspan, and Workspan
You may live to 90 or beyond. Plan your health, your money, and your career for a longer life, and enjoy today too.
Financial Blind Spots: What Successful People Miss
Success creates a false sense of security. The pieces you're missing are usually simple, and cheaper to fix now than later.
How Much Is Enough to Walk Away From Work?
There's no magic number. There is inflation, RMDs, the 4% rule's blind spot, and healthcare. Here's how I think about enough.
Why High Earners Outgrow Their First Financial Strategy
Max the 401(k), hold the stock, sit on cash. That's the plan many high earners never replace. What I look at first.
Annuities and Whole Life Insurance: Who Really Benefits
Annuities and whole life pay big commissions. Why I've rarely seen them fit a high earner, and how to spot the conflict.
Financial Planning for High Earners: Five Areas to Rethink
Equity comp, taxes, retirement, cash flow, estate. Five places high earners do what everyone else does without asking why.
After Maxing Out Your 401(k) and IRA: Where to Save Next
Maxed out your 401(k) and IRA? Four more places to put money, with the pros and cons of each.
Retirement Tax Buckets: Planning Beyond Your 401(k) and IRA
Tax-deferred, tax-free, and taxable: why the mix matters, and how to build cash flow that outlasts your career.
How to Calculate Your Financial Freedom Number
High income isn't wealth. How to find your financial freedom number and build a plan that sustains itself.
Roth Conversions and Tax-Free Growth: How the Strategy Works
Why pre-tax savings can shrink at withdrawal, and how Roth accounts and conversions change the math.
Mega Backdoor Roth: How High Earners Save More Tax-Free
If your 401(k) allows after-tax contributions, you may be leaving Roth space unused.
Executive Retirement Planning: RMDs, RSUs, and Social Security
A large 401(k) is not a large retirement income. Taxes and RMDs take their cut first.
Making $500K and Still Feeling Paycheck to Paycheck
I hit the income number and the pressure got worse. The high-income trap, and what changed when I structured things differently.
The Blind Spot That Catches High Earners Off Guard
You can out-earn bad decisions for a while. Then the math catches up. The blind spot I lived through and still see all the time.
False Confidence: The Financial Blind Spots You Can't See
Many people assume they're fine. My father did too. What false confidence costs, and why couples need one plan, not two assumptions.
Five Financial Principles That Shaped How I Manage Money
My first big paycheck was gone in weeks. Five principles I learned the hard way and still use with clients.
How to Stop Wasting Money and Take Back Control
Ask one question before you buy: will this matter in two to five years? It cut my junk spending by 90%.
High Income but No Wealth? Earn, Keep, and Grow
A bigger paycheck becomes a bigger house and more taxes. The treadmill effect, and the earn-keep-grow machine that beats it.
Building Wealth: Capital, Systems, and People
Dry powder, automation, and relationships. The three levers I see behind lasting wealth, and why all three matter.
Three Habits That Build Wealth and Keep It
The people who get ahead save automatically, manage the real risks, and use a trusted team. Consistency, not brilliance.
Questions to Ask Before You Take Anyone's Financial Advice
The costliest mistakes are the ones you didn't know to look for. How to tell whose advice actually has your back.
The Money Conversation to Have With Your Partner
Bills and budgets aren't the conversation. Nine questions couples avoid about money, family, and the life you're building.
Who You Marry Is the Biggest Financial Decision You Make
You can earn millions and still live check to check after a divorce. Why partner alignment matters more than any portfolio.
Money Mistakes Smart High Earners Make, and What Works
Intelligence alone doesn't drive financial success. Behavior, clarity and structure do. Four traps and five habits.
Earning More but Still Stressed About Money
More income often means more pressure, not more freedom. What's usually missing isn't money. It's clarity.
Why Some High Earners Can't Spend and Others Overspend
Same income, opposite habits. Money behavior is rarely about the money. It's about alignment with the life you want.
Why a High Income Doesn't Automatically Build Wealth
Making great money isn't the same as building wealth. Here's the gap I see most often, and the questions that close it.
High Income vs. Real Wealth: Why They're Not the Same
Wealth isn't what you earn. It's how many decisions you can make without asking permission. The old model doesn't get you there.
High Income but Still Stressed About Money: What's Missing
Earning $400K or $1M and still uneasy? Most of that unease comes from noise and sales pitches, not reality. Here's how to clear it.
How to Ignore Market Noise and Run Your Life Like a Business
Headlines flip overnight. A personal blueprint for filtering the noise, taking measured risks, and defining success your way.
How to Reverse Engineer Your Financial Goals
Many people start with action and hope. Start with a clear picture of the end, then work backward to the moves that get you there.
How to Filter Financial Advice and Build Your Own System
Overwhelmed with information and short on clarity? Define what you want, build a system, and filter the rest.
How to Pivot Without Losing Sight of Your Financial Goals
Pivoting isn't failing. A clear but flexible plan, a feedback loop, and the right team keep you moving.
Why a Few Deep Relationships Are Worth More Than Money
You don't need a big circle. You need a few people who tell you the truth. Money can't buy that.
Four Personal Finance Myths From Social Media
Copy the rich, avoid all debt, skip the plan, chase passive income. Four myths that cost high earners money.
What You Don't Know About Your Money Could Cost You
Two stories, same lesson: smart people wing it with money. Here's what that gap costs.
Treat Your Life Like a Business: Vision, Plan, System
A clear vision, a plan, and systems you actually work. Plus why asking questions is a strength, not a weakness.
Building Wealth as a High Earner: Five Principles That Hold Up
Control what you can, plan for taxes and liquidity events, stop winging it, and keep money tied to the life you want.
Financial Mistakes High Earners Make: Stock, Taxes, and No Plan
Concentrated company stock, tax-heavy accounts, and no plan. The three mistakes that cost high earners the most.
Stop Stressing About Money: A Plan for Tech and Biotech Earners
Panic selling, too much company stock, FOMO, and tax blind spots. Why emotions cost you, and how a plan helps.
Financial Independence Without Extreme Frugality
FIRE without deprivation: spend on what adds value, invest consistently, and watch lifestyle inflation.
The High-Income Trap: Staying Focused on Building Wealth
High income, higher costs, endless shiny objects. Consistency beats chasing the next big thing.
Should You Hire a Financial Advisor or Go It Alone?
DIY works until it doesn't. The gaps are usually in what you didn't know to ask.
Why a New Perspective Changes How You See Your Money
Nobody has it all figured out. The ones who admit it are the ones who keep growing.
The Quiet Struggle of High-Income Success
You hit the numbers. Now the harder question is what the money is for.
How to Make Better Financial Decisions: Nine Habits
You make thousands of decisions a day. The money ones deserve a system, not a gut call.
Seven Steps to Design the Life You Want
A seven-step roadmap: rate what matters, write a purpose statement, audit your 168 hours, then commit to a few real changes.
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