Greg Smith, co-founder of Thinkific, launched Thinkific in 2012 to simplify creating and selling digital courses. Despite numerous pivots and setbacks, they found success after launching their new software in 2015. The company has since grown to 280 employees and generates about $60 million in ARR. Greg attributes the company's success to factors such as bootstrapping and profitability, the role of personality and relationships in acquiring early customers, and the importance of persistence and trusting one's entrepreneurial instincts.