The Current Issue
How to Exit a Concentrated Position Without Accidentally Lighting Money on Fire.
How to Exit a Concentrated Position Without Accidentally Lighting Money on Fire
MAR 17 · 14 MIN
The Archive
Recent issues.
- № 35FEB 27
Private Company Valuation: Is the Number Real… a Story... or BS?
Why private-company valuations can be technically real but economically misleading — four structural mechanisms employees should understand.
6 MIN READ - № 34FEB 5
Tax Strategy for Highly Appreciated Stock: (1) Eliminate vs. (2) Reduce vs. (3) Defer —- And Why Confusing Them Is Expensive
Eliminate vs. reduce vs. defer for appreciated stock — the three-bucket tax-strategy taxonomy, and why confusing them is expensive.
10 MIN READ - № 33JAN 22
Why Your “Insider Edge” Is Way Smaller Than You Think
Why insider knowledge doesn't translate to a real stock-picking edge — public investors know more than you think, and only 20% of returns are company-specific.
5 MIN READ - № 32JAN 8
SpaceX Employee Equity: The 5 Decisions That Matter Most in 2026 (and How to Make Them)
The 5 SpaceX-employee decisions for 2026: tender participation, share selection, option exercise, IPO readiness, and the concentration plan.
14 MIN READ - № 31DEC 10
How to Pay NO Tax on the SpaceX Tender (And Prep for a $1.5 Trillion 2026 IPO)
SpaceX-specific tax playbook for the 2026 tender and IPO: which shares to sell, the ISO tainting rule, AMT planning, and long/short tax deferral.
17 MIN READ - № 30DEC 10
How to Convince Yourself to Sell Your Company Stock (Even When It Feels Wrong)
How to overcome the association, endowment, and anchoring biases that keep you holding company stock — with frameworks that turn the decision into data.
6 MIN READ - № 29NOV 21
Top 5 Financial Items for Tech Employees Prior to EOY
Five Q4 moves for tech employees: ISO/AMT review, tax-loss harvest, charitable giving via DAFs, max the 401(k), benefits selection.
5 MIN READ - № 28NOV 21
How to Borrow at Rates Below 4% AND with Tax Benefits
Box-spread borrowing: how to get sub-4% loans against your portfolio with the interest treated as a tax-deductible capital loss.
7 MIN READ - № 27OCT 22
Client Case Study: Diversifying Concentrated Stock Before Leaving California
A side-by-side case study of three ways to diversify $2M in concentrated stock before moving CA to TX: $0 vs. $328k in tax.
5 MIN READ - № 26OCT 8
Why AI Employees Need to Rethink Their Equity Comp Strategy
Why 'reverse acquihires' make AI employee equity riskier — and why negotiating an extended PTEP is the cleanest protection.
6 MIN READ - № 25SEP 25
Navigating Post-IPO Wealth: Tax Optimization and Portfolio Strategy for a $1.5M Income Event
A $1.5M post-IPO income event end-to-end: DAF giving, hedge-fund losses, 130/30, exchange fund, regret-minimized selling plan.
7 MIN READ - № 24SEP 16
The IPO Millionaire’s 180 Day Lockup Playbook
Use your post-IPO lockup as planning time: build a financial plan, define a stock strategy, and stage your tax-optimization moves.
5 MIN READ - № 23SEP 9
The RSU Tax Withholding Dilemma: 22% vs 37% (And Why Your Choice Matters More Than You Think)
22% vs. 37% RSU withholding at IPO: why it's really a 'hold more company stock' bet, with decision rules and scenarios.
7 MIN READ - № 22SEP 9
Leaving Money on the Table: The Logic Behind 2025's IPO Underpricing
Why 2025 IPOs are systematically underpricing: companies prioritize public access, VCs need liquidity, banks want momentum.
3 MIN READ - № 21SEP 8
Pro-Rata Rule for Equity Comp: How Moving States Affects Taxes on ISO/NSO/RSU Equity
How the state pro-rata rule actually works when you've vested equity across states — and the two common misconceptions that cost real money.
4 MIN READ - № 20SEP 8
Navigating Meme Stock Volatility (If You Accidentally Get Caught In the Upswing)
How meme-stock spikes actually trade (call options + short interest), and a structured selling plan if your company stock gets caught up in one.
8 MIN READ - № 19SEP 8
The Top 3 Ways the New Tax Bill ("OBBB") Impacts Tech Workers
Three OBBB tax-bill changes that matter for tech workers: AMT exemption permanence, SALT-deduction cap shifts, and the new QSBS rules.
4 MIN READ - № 18SEP 5
Betting Big on Company Stock? Here's a SMART Way To Do It
A five-step framework for holding concentrated stock with intent: downside plan, research, price-based actions, tax-smart, check-ins.
7 MIN READ - № 17MAY 28
More Than Numbers: The Power of REAL Connection in Financial Advice
Why financial advice that matters isn't about numbers — the case for the human side of equity-comp planning, through a real client story.
4 MIN READ - № 16MAY 28
Your First Financial Advisor: A Tech Professional’s Guide to What Comes Next
What to expect from working with your first financial advisor: 6 value categories beyond just managing money, plus how to know you're ready.
5 MIN READ - № 15MAY 14
What Happens To Your Stock Options When Your Company Is Acquired?
Two factors decide your equity outcome in an acquisition: the deal structure (cash, stock, hybrid) and how the acquirer treats each grant type.
14 MIN READ - № 14MAY 7
4 Things Most Tech Folks With ISOs Don’t Know About AMT (It's Likely Not As Bad As You Fear)
Four things tech folks don't know about AMT — including the prepayment-credit mechanic that makes it much less scary than it looks.
8 MIN READ - № 13APR 30
What Tech Employees Need to Know About VC Liquidation Pref (So You Don't Get Screwed)
How VC liquidation preferences work in an exit, with three worked examples showing when they don't hurt, do hurt, and take everything.
6 MIN READ - № 12APR 23
DATA showing WHY you should sell your RSUs when they vest
Four years of S&P 500 data showing why selling RSUs at vest and diversifying beat holding 72% of the time, and beat 97% on risk-adjusted return.
8 MIN READ - № 11APR 15
Should You Be Investing In The Stock Market Right Now (And How Much)? Here’s How To Decide!
A 5-step framework for deciding how much to invest in stocks: future expenses, time buckets, risk profile, and a per-bucket allocation.
7 MIN READ - № 10APR 13
Are You 35-45, make $500k+ with RSUs, and STRESSED about Money? Here's How to Fix It
Why high-earning tech professionals with RSUs feel stressed about money — and the cash, stock, investment, and tax system that fixes it.
3 MIN READ - № 9APR 13
Create A “No Regrets” Selling Plan For Your Stock Comp
A 'no-regrets' selling-plan framework: bucket your concentrated holdings into immediate sales, long-term hold, and structured sales over time.
8 MIN READ - № 8APR 13
4 Costly Tax-Return Mistakes Tech Professionals Make with Equity Compensation
Four tax-return mistakes that cost tech professionals: NSO/RSU cost-basis fixes, ISO/AMT dual-basis, RSU underwithholding, ESPP double-tax.
6 MIN READ - № 7APR 13
Negotiating an Option Extension/PTEP when LEAVING a company
Five strategies for negotiating a PTEP (post-termination exercise period) when leaving — the pros, risks, and trust required for each.
7 MIN READ - № 6APR 13
Big Tech Perk: Mega Back Door Roth
The Mega Backdoor Roth: a quietly powerful 401(k) feature that lets you stuff up to $70k into a Roth at the right tech employers.
3 MIN READ - № 5APR 13
What To Do When You Own TOO Much Company Stock
Eight strategies for reducing a concentrated company-stock position, from the simplest (sell + pay) to exchange funds and 351 ETF conversions.
6 MIN READ - № 4APR 13
Why Most People Fail at Personal Finance—And How to Avoid Their Mistakes
The four barriers that derail personal finance — time, knowledge, interest, psychology — and the two paths to overcome them.
7 MIN READ - № 3APR 13
Navigating Tender Offers for Pre-IPO Companies
Tender offer 101 plus a framework for the two key decisions: CAN you participate (eligibility), and SHOULD you (financial + tax + risk).
3 MIN READ - № 2APR 13
Joining a Startup? 7 KEY Questions To Ask/Know About Your Equity Grant
Seven questions to ask before signing a startup offer: percent ownership, vesting, 83(b), PTEP, liquidation prefs, secondaries, and 409A.
6 MIN READ - № 1APR 13
Do Your Shares/Options Qualify for QSBS?
The 5-point checklist for whether your shares actually qualify for the QSBS capital-gains exclusion (and the misconceptions to avoid).
4 MIN READ
SHOWING 36 OF 36
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One letter every other Tuesday. Equity comp, taxes, IPOs, tenders, and the decisions in between. Written by someone who does this work daily.
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