One important datapoint is that Jack Dorsey did something very similar at Square in December 2013: http://fortune.com/2013/12/20/squares-dorsey-returns-10-of-hi

One important datapoint is that Jack Dorsey did something very similar at Square in December 2013: http://fortune.com/2013/12/20/squares-dorsey-returns-10-of-his-shares/ http://fortune.com/2013/12/20/squares-dorsey-returns-10-of-h... Judging by how strong the Square team is, and how much he's respected there, I imagine this move is now part of his playbook to build a great organisation. It's courageous. From the link above: > Jack Dorsey, the founder and CEO of Square, has voluntarily given 10% of his shares in the company back to Square. The highly unusual move will expand significantly the pool of shares available for employee compensation and acquisitions while minimizing dilution for shareholders. > Dorsey owns approximately 30% of Square and is giving back about 3% of the company’s total equity. The shares Dorsey is returning are worth between $97.5 million and $150 million based on estimates of the company’s valuation.