Common questions

What financial planning is different for startup founders?

Nearly all wealth is illiquid and concentrated in one private company, income is often below market, and outcomes are binary-ish. Planning centers on personal runway, QSBS eligibility from day one, equity and option strategy at each round, and not letting the company's risk profile become the household's.

What is QSBS and why do founders care?

Qualified Small Business Stock (Section 1202) can exclude a large amount of federal capital gains on qualifying C-corp shares held for the required period, with rules that changed for stock issued after July 2025. Eligibility decisions are made at incorporation and each issuance - get it confirmed by a tax professional early, because it's nearly impossible to fix later.

Should I take secondary sales when investors offer them?

Selling a slice at a priced round diversifies your risk without leaving the company, and many advisors encourage it once the position is life-changing on paper. Weigh it against signaling concerns, board dynamics, and taxes on the gain. A partial sale that secures the household changes how you run the company - usually for the better.

How should I handle my founder equity and options as we raise?

Track vesting, exercise costs, and AMT exposure at each stage; consider early exercise or 83(b) elections where applicable (deadlines are short and absolute); and model dilution per round. Equity decisions at startups have strict deadlines that do not move.

What personal finance basics matter most before an exit?

Runway (12+ months of expenses accessible), insurance (health, disability, term life), a real salary when the company can pay one, and retirement contributions even in lean years. Founders who skip the basics make company decisions from personal fear - expensive for both.

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