From $10K/Month Side Hustle to IPO Success: Greg Smith’s Story

The Beginning: From Part-Time Tutoring to Online Courses

While studying law in 2005, Greg Smith started tutoring LSAT prep to pay off student loans. His in-person courses had excellent feedback but limited reach. Smith moved online, packaging his expertise into a $29 course that changed everything. Within years, his LSAT business generated approximately $10,000 monthly—a transformative moment revealing the power of converting knowledge into digital products.

Building the Platform: Solving Problems, Creating Solutions

Why Thinkific Was Built

When Smith searched for course-building software, existing solutions fell short of his needs for exceptional learning experiences, strong commerce features, and brand control. With his brother Matt, he built a custom platform. As other experts requested similar tools, they recognized the real opportunity: providing entrepreneurs with accessible platform software. Thinkific launched in 2012 with this mission.

Growth Through Customer Focus

Smith’s approach emphasized customer success above metrics. Early operations involved scrappy methods—personally filming courses, handling payments over the phone, and learning directly from customers. This relentless focus on helping businesses succeed became Thinkific’s foundation. The platform eventually supported 77,000 users generating billions in sales.

From Bootstrap to IPO

Smith initially funded Thinkific with LSAT course proceeds and credit cards. Early investment came from a $50,000 family loan. Subsequent funding rounds—$600,000, $1 million, $2 million, and $20 million—fueled growth. The company reached monthly recurring revenue after two to three years, eventually achieving 60-70% annual growth. In 2021, Thinkific went public, raising $184 million and validating Smith’s belief that meaningful customer impact builds lasting businesses.