In the late 1990s, he signed with a local rap label, Street Flavor, and began a business relationship with producers Kevin Grisham and Sonny Paradise.

The partnership resulted in Mak Million, Haystak's 1998 debut album, followed two years later by Car Fulla White Boys.

By this point, Haystak had garnered a substantial regional following, and underground hardcore rap publication Murder Dog began promoting his work.

The attention attracted the label Koch Records who signed Haystak and re-released Car Fulla White Boys in late summer 2000.

Since March 2017, Haystak has been partnered with Daphne McCool and Russell Duke who have rebuilt his brand and have contributed to his continued success.