Cullen has a range of specialties including interaction design, creative direction, software architecture, business development, strategy development, and private capital formation. His career began early, working with Microsoft's Windows team during High School. After graduating he joined Microsoft's Xbox team to work on the revamp of the Xbox 360 product line.Despite starting in enterprise, Cullen went on to co-found startups like Lumier (operating systems), Inksy (custom merchandise production and marketplace), Indais (data access control and management).  He’s previously served as an in-house technology creative advisor for musicians like Lady Gaga and Beyonce.