From Courtrooms to Courses: The Unlikely Journey That Built Thinkific
Greg Smith didn't set out to build one of the world's leading online course platforms. He set out to be a corporate lawyer. But somewhere between a tutoring side hustle, a $10,000 month, and a revelatory moment at 30,000 feet, a different future came into focus — one that would go on to help thousands of educators and entrepreneurs share their knowledge with the world.
The lawyer who fell in love with deals
Greg's path to entrepreneurship began, oddly enough, with a fascination for corporate law. What drew him in wasn't the courtroom drama — it was the front-row seat to some of the most consequential moments in business. Mergers. IPOs. High-stakes decisions that shape industries.
As he saw it, a CEO might navigate those moments once or twice in a career. A corporate lawyer lives inside them constantly. For someone hungry for impact, that asymmetry was irresistible.
So Greg went to law school. And to help cover the bills — student loans included — he started tutoring students for the LSAT.
The side hustle that changed everything
Greg was good at tutoring. But he kept hitting the same wall: there were only so many students he could fit in a room, only so many hours in a day. He wanted to reach more people. So in 2005, he did something ahead of its time — he launched an automated online course.
The results were immediate. The course began generating thousands of dollars a month with minimal ongoing investment. Then came the month that shifted his entire perspective: during a break from his law job, Greg focused on promoting the course — and it earned $10,000 in a single month. More than his corporate salary.
That wasn't just a win. That was a signal.
The aha moment at altitude
Still, Greg didn't make the leap right away. Entrepreneurship had always called to him — he'd grown up watching his parents nurture big ideas that never quite made it off the ground, held back by the demands of their day jobs. He recognized the pattern and didn't want to repeat it.
Then, on a plane ride, it crystallized. He needed to build something of his own.
He left his law job, though his first startup venture didn't pan out. But as he regrouped and assessed his options, something interesting was already happening: other people and businesses were reaching out, asking him to help them build their own course platforms. He had inbound demand. He had the solution. He had the experience.
In 2012, Greg founded Thinkific.
Building with a brother — friction and all
Every founder's journey has its complications. For Greg, one of the most formative was also one of the most personal: his younger brother Matt.
When Matt saw Greg wrestling with code in the early days, he stepped in to help — and became a cofounder. What followed was years of productive tension. Both brothers were driven. Both wanted to reach the same destination. But they had very different ideas about how to get there, and both wanted the CEO seat at a company that, in truth, didn't yet have enough decisions to fill two leadership roles.
After three years, Matt stepped away to pursue his own path. But the story didn't end there.
As Thinkific scaled, Matt became one of Greg's most trusted advisors — eventually returning as Chief Strategy Officer. With the company growing rapidly, the dynamic between the brothers transformed completely. There were now more than enough decisions to go around, and Greg was grateful for every one Matt could take off his plate. Today, Matt sits on the board as an advisor, and remains the person Greg calls when things get hard — not for strategy, just to talk.
Raising kids who celebrate failure
Perhaps the most telling window into Greg's mindset isn't his business philosophy — it's his parenting.
Greg talks to his kids, now 7 and 10, regularly about failure. When his daughter was around three and asked what failure meant, his answer was simple: when something doesn't go the way you want, it's a huge opportunity.
That message has stuck. Now, his kids don't just tolerate failure — they celebrate it. They eagerly share their failures with each other and with friends, treating each stumble like a badge of honor. Other parents sometimes raise an eyebrow. Greg considers it one of his greatest successes.
Because if there's one thing his own journey has taught him, it's that the moments that look like dead ends — the startup that didn't work out, the conflict with a cofounder, the career pivot that made no obvious sense — are often exactly where the most important chapters begin.