September 23, 2023

Volume XIII, Number 266


Pre-IPO Liquidity – Tax and Legal Considerations [WEBINAR]

As late-stage startups have increasingly stayed private longer, the market for resales of pre-IPO equity has exploded. This webinar will focus on some of the tax and legal implications for executives and early stage investors that are seeking liquidity for their unregistered shares and options.


  • US tax treatment of cashless and cash exercises of options, sale of shares, forwards and indirect sales
  • Capital gains vs. ordinary income, along with strategies to help minimize tax burden
  • Withholding issues and employer exposure to tax liability if no withholding is made
  • Legal restrictions on transfers, including under securities laws and typical stockholders’ agreements
  • Liquidity structuring, including option finance