Born in New York City, Dash swept the floors of a local barbershop and sold newspapers in order to buy sneakers and shirts as a teenager.

[9] In April 2014, it was announced that Dash is involved with Blind Debit, a fingerprint payment application being developed by Dez White.

[12] Dash met R&B singer Aaliyah in New York City in the summer of 2000 through his accountant,[13][14] and dated her until her death on August 25, 2001, in a plane crash in The Bahamas.

[24] In 2014, Dash was ordered to pay Linda Williams, the mother of his son Boogie, $50,000 for causing her to be prosecuted on harassment charges in 2009.

[25] In April 2015, Dash's ex-wife, Rachel Roy, accused him of domestic abuse and filed for a restraining order.

[26] Days later, Dash filed a $2.5 million claim against Roy in asserted damage for allegedly mishandling their joint fashion business, Royale Etenia.

[28] Lee had received financial support from Dash early in his career, and reportedly failed to repay him despite his subsequent success.

The first warrant was issued in April 2015 in the Supreme Court in New York County case of Cindy Morales; he owed $62,553 since 2012.