James Whitaker Park — Managing Director, Pre-IPO Advisory

James works with employees and founders at late-stage private companies, most of them between a Series D and a filed S-1. His practice has handled roughly forty liquidity events across traditional IPOs, direct listings, and a handful of SPAC combinations. Clients typically come to him when the company files confidentially and they realize their entire net worth, six-figure salary plus seven-figure unrealized equity, is sitting in a single concentrated position they cannot sell for another eight to ten months.

The pattern he plans around is the IPO tax cliff for double-trigger RSU holders. Imagine a principal engineer with 60,000 double-trigger RSUs that vested over four years but do not recognize income until the liquidity event. On IPO day, all sixty thousand settle as ordinary W-2 wages. At a $48 reference price that is $2.88M of compensation income hitting at once, with supplemental withholding usually set at 22% federal below $1M and 37% above. The shortfall against the client’s true marginal rate runs $180k to $320k, payable April 15, while the stock itself is locked up for 180 days and can fall 40% inside the blackout. James builds cash-reserve plans and 10b5-1 sell programs that assume the worst-case post-lockup drawdown.

He reviews content on lock-ups, double-trigger mechanics, and IPO-window cash planning.