Darling Scott 4

What Happened
Scott Darling, Chief Legal Officer of Upstart Holdings (UPST), sold a total of 727 shares in open-market/private sales on May 15, 2026. The sales were: 286 shares at a weighted average price of $28.84 (≈ $8,248) and 441 shares at a weighted average price of $29.99 (≈ $13,228), for combined proceeds of approximately $21,476. According to the filing, these sales were made to satisfy tax withholding obligations tied to the vesting of restricted stock units (RSUs).

Key Details

• Transaction date: 2026-05-15 (filed on Form 4 2026-05-18; appears timely).
• Sale details:
  • 286 shares sold @ weighted avg $28.84 (reported price range $28.44–$29.27).
  • 441 shares sold @ weighted avg $29.99 (reported price range $29.58–$30.54).
• Total shares sold: 727; total proceeds ≈ $21,476.
• Reason: Shares sold to cover tax withholding for RSU vesting (footnotes F1, F3).
• Holdings after transaction: filing notes a deposit of 814 shares from Darling into the Darling Family Trust; the filing lists trust-held shares (see footnotes F5–F6).
• Footnote commitments: Reporting person will provide detailed per-price breakdown on request (F2, F4).

Context

• These sales were routine tax-withholding dispositions tied to RSU vesting and do not necessarily signal a change in insider sentiment. RSUs are contingent awards that convert to shares upon vesting; withholding sales are common to cover associated taxes.
• No options exercise or large new purchases were reported. This is an insider sale (code S) for tax purposes rather than a discretionary market-sale signal.