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.
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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.
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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.
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Double-Trigger RSUs
Learn what a double-trigger RSU is, why late-stage private companies use them, and how vesting and settlement can diverge.
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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.
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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.
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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.
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How to Evaluate a Startup Equity Offer
A practical framework for evaluating the equity portion of a startup job offer, including how to calculate ownership percentage, value the grant, and compare total compensation.
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What Happens in a Down Round
Understand how down rounds affect employee equity — from dilution and underwater options to 409A repricing and anti-dilution provisions.
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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.
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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.
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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.
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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.
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Section 1202 / QSBS Tax Exclusion
Learn how Qualified Small Business Stock (QSBS) under Section 1202 can exclude up to $10 million in capital gains from federal tax, and what startup employees need to qualify.
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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.
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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.
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How to Sell Private Company Stock
A step-by-step guide to selling private company shares on the secondary market, including transfer restrictions, pricing, tax implications, and how platforms like Hiive work.
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Private Company Stock Liquidity Guide
Compare secondary sales, equity financing, exchange funds, and donor-advised fund strategies for private company stock.
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All content is for educational purposes only. Not investment, legal, or tax advice.
Consult qualified professionals before making financial decisions.