Thembekwayo began his professional career in public speaking and consulting. At age 21, he founded a forensic marketing agency, before transitioning into international speaking engagements focused on business strategy, leadership, and sales. He later expanded into venture capital and private equity, founding MyGrowthFund Venture Partners, an investment firm focused on supporting high-growth small and medium-sized enterprises (SMEs) across Africa. Through the firm, he has been involved in initiatives such as incubator programmes and the School of Scale, a training and development platform for entrepreneurs. In a 2015 interview with Forbes Africa, Thembekwayo reflected on early career challenges, including a 2011 investment in a steel company that failed due to insufficient due diligence. He has since emphasized the importance of legal and structural frameworks in business, stating that entrepreneurs must ensure "the legal side holds water" before proceeding with investments. From 2014 to 2015, Thembekwayo was one of the investors, or "dragons" on South Africa's ''
Dragons' Den'' reality TV series by
Mzansi Magic with other dragons including
Vinny Lingham,
Gil Oved, Lebo Gunguluza among others. == Personal life ==