Stuart's first job was teaching English as a second language at NBS Bank at Kingsmead in Durban. From being an ABET instructor in the late 1990's, when ABET was just becoming widely adopted and mainstream, Stuart joined a team of friends from Wits to head up the English language teaching side of Rainbow Basic Communications, which was focusing on teaching basic Zulu, Sotho and Xhosa. 
Stuart and his friends later published The National Training Directory in the year 2000 and continued to publish it until 2010 under different names including the Skills Development Guide and The National Skills Development Handbook. 
During this period, Craig Macaskill was working on the same publication, but with his love for agriculture began to research agricultural training, and ended up developing an entirely new publication - The National Agricultural Directory and its Afrikaans sister, Die Nasionale Landbougids. 
In 2012, Stuart setup his own company, RainbowSA Publishing, to publish The Skills Handbook and Craig Macaskill's The Agri Handbook.  
Stuart is also currently the Project Lead for The WorkFit Compaign and the Seta Liaison for the University of the Witwatersrand.