K-1 season is a nightmare. Your CPA sends invoices, not answers. Half your portfolio has 2021 marks. NettWorth is the first tool built for the chaos that comes after the checks.
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Angel investments generate K-1 forms (for fund/SPV investments), 1099s (for some direct investments), and potential 1099-B or 1099-DIV on exits. The core tracking challenge: each investment needs its original cost basis recorded at investment date, plus any follow-on basis from capital calls. QSBS (Section 1202 Qualified Small Business Stock) qualification needs to be tracked at investment date — you can't reconstruct it later. Most angels use a combination of a personal spreadsheet, AngelList portfolio tracking, and a CPA who specializes in angel/startup equity. Common mistakes: not tracking whether QSBS criteria were met at investment date, letting basis go unrecorded after capital calls, missing K-1 forms from SPV administrators.
Section 1202 Qualified Small Business Stock offers up to $10 million (or 10x basis, whichever is greater) in capital gains exclusion on the sale of qualifying shares — effectively tax-free gains at the federal level. The qualifying criteria must be met at the time of investment, not at exit: the issuing company must be a domestic C-corp, with gross assets under $50 million at time of investment, in a qualifying industry (most tech/software companies qualify; financial services, law, consulting, hospitality do not). Shares must be held for over 5 years. Post-2022 legislation raised the exclusion to $15 million for certain investments. If you invested in eligible companies, tracking this from day one is the highest-ROI tax optimization available to angels.
Private portfolio valuation between priced rounds is genuinely uncertain. The industry standard for angels tracking their own portfolio: last-round valuation for any company that has raised in the past 18-24 months; impairment write-down for companies that are zombie or non-communicating; zero for known failures. This is consistent with how most institutional LP reports value holdings. What you get from this approach: a conservative-but-defensible net worth estimate. What you don't get: a precise answer (it doesn't exist). The more important metric for tax purposes: your cost basis, which is precise regardless of current valuation. Your cost basis determines your gain at exit; current portfolio value is a planning estimate.