Private company stock guides
Educational guides for startup employees and shareholders covering equity basics, vesting, stock options, taxes, liquidity, and private-market planning.
Equity Basics
Understand the building blocks of private-company compensation, including shares, vesting schedules, RSUs, and stock options.
What Is Equity?
A practical guide to what equity means at a private company, the main types of equity employees receive, and how to evaluate what your grant may actually be worth.
Read guide →
Stock Vesting, Explained
Learn how vesting works for startup equity, what cliffs and schedules mean, and how vesting affects what you actually keep if you leave.
Read guide →
Restricted Stock Units (RSUs)
A practical guide to what RSUs are, how they vest, when they are taxed, and what makes private-company RSUs different from public-company RSUs.
Read guide →
Double-Trigger RSUs
Learn what a double-trigger RSU is, why late-stage private companies use them, and how vesting and settlement can diverge.
Read guide →
Incentive Stock Options (ISOs)
Understand how ISOs work, what makes them different from NSOs, and how exercise timing, holding periods, and AMT can shape the outcome.
Read guide →
Non-Qualified Stock Options (NSOs)
A practical guide to how NSOs work, how they are taxed at exercise and sale, and what employees should weigh before acting.
Read guide →
Stock Splits, Explained
Learn what stock splits and reverse splits mean for private-company shareholders, including how share counts, strike prices, and basis are usually adjusted.
Read guide →
Taxes & Planning
Learn the tax rules and planning concepts that often matter most when you exercise, hold, sell, or transfer private-company stock.
Alternative Minimum Tax (AMT)
A practical guide to why AMT matters for employees exercising ISOs and how to think about the tradeoff between tax efficiency and illiquid risk.
Read guide →
Capital Gains Tax on Startup Shares
Learn the difference between short-term and long-term capital gains, how basis works, and why the tax result depends on how and when you acquired your shares.
Read guide →
Accredited Investor Rules
Understand what accredited investor status means, who may qualify, and why it can matter for private-market investing and certain secondary transactions.
Read guide →
Family Loans for Option Exercises
A practical guide to using a family loan to fund an option exercise, including documentation, tax considerations, and the tradeoffs compared with other financing options.
Read guide →
Liquidity & Exits
Compare the paths employees use to turn private shares into actual liquidity, and the tradeoffs that come with each one.
Tender Offers for Startup Employees
Learn how private-company tender offers work, who may be eligible, and what employees should weigh before selling into a company-led or investor-led liquidity event.
Read guide →
Should You Borrow From Your 401(k) to Exercise Options?
A practical look at when borrowing from a 401(k) to exercise stock options may help, when it may backfire, and what alternatives to compare.
Read guide →
Private Company Stock Liquidity Guide
Compare secondary sales, equity financing, exchange funds, and donor-advised fund strategies for private company stock.
Read guide →
All content is for educational purposes only. Not investment, legal, or tax advice.
Consult qualified professionals before making financial decisions.