Greg Smith and the classroom that wouldn’t stay small

Greg Smith did the arithmetic in a classroom. He was teaching people how to get into law school, looking at a room full of students, and considering the difference between what they paid and what he earned. Running the class himself looked promising. Then he discovered that persuading thirty people to be in the same room, in the same city, on the same date was a job of its own.

The internet offered a larger room. Smith put lessons online, first as free material and then as a course. His brother Matt could write software; Greg could explain the Law School Admission Test. Between them, they had the ingredients for a modest education business. They also had a disagreement about how much needed to be ready before opening day.

Thirty days to open the doors

Matt pushed for a deadline: launch in thirty days. Greg’s ambitions had to fit inside it. That meant publishing a smaller course, learning from students, and improving what was already available. The deadline gave an expansive idea a useful enemy: the calendar.

The early course cost $29. In time, it brought in roughly $10,000 a month. Those figures make a pleasing before-and-after, although the distance between them matters. The course grew over years. It also supplied something more practical than a good founding anecdote: money that could help finance another business.

Smith’s teaching business became AlphaScore. He had taken something he knew how to do and made it available to people he would never meet in a classroom. The product had escaped the capacity of the room. His working life was about to follow it.

The lawyer liked the other side of the table

Smith holds commerce and law degrees from the University of British Columbia. He went into securities and corporate law, a profession he has described with more affection than the usual escape story allows. He liked the people. He liked the work. Even the intense stretches suited him.

But he watched his corporate clients and recognized an attraction to their side of the relationship. He could help them build businesses, or he could try building one himself. “I love helping you, but I’d probably be even happier if I was doing what you’re doing,” he recalled thinking.

Leaving meant surrendering the predictable paycheque. In the early days, Greg and Matt handled the unglamorous necessities themselves, from the banking arrangements to taking out the garbage. A founder’s title apparently came with excellent access to the bins.

Other teachers began asking how the online course worked. Some taught exam preparation; others taught skills such as Excel. They wanted the machinery behind Greg’s classroom. In 2012, Greg, Matt, Miranda Lievers and Matt Payne founded Thinkific to help other people create and sell their own courses.

Selling software, by hand

The problem reached beyond putting a video on a website. Smith wanted a learning experience that worked, a way to charge for it, and control of the brand. The customer relationship mattered too. A teacher building a business needed a place that could feel like their own.

At first, helping people do this involved an almost comical amount of personal service. The early team called prospective customers and helped get their material online. Smith has described filming courses, helping with sales and marketing, and sometimes becoming an instructor for a customer himself. Payment collection could require another phone call.

The process exposed the work a product would eventually have to absorb. If a customer could not get a course ready, a feature list offered little consolation. The founders were close enough to see the obstacles and, for a while, close enough to remove them by hand.

Smith has traced Thinkific’s first fifty customers to cold calling. His early marketing also used useful free material, including YouTube videos, to attract people who wanted to learn. Teaching remained a way to find buyers for the tools that made teaching possible.

Later, Smith would describe focus as a product decision in its own right. A platform could accumulate features until it offered a little of everything, with little reason for customers to choose it. He preferred giving people a clear reason to buy. That required deciding which problems the company could solve well, then being willing to leave other requests alone. For a founder surrounded by suggestions, restraint becomes a form of work. The customers still have plenty to say; the company still has to choose.

There were years of revisions before the business found dependable traction. Smith has described that period as a search for the right direction, with several changes along the way. The tidy founding date conceals a less tidy process: trying, listening, and deciding which requests pointed toward a repeatable business.

“Be embarrassed by what you produce.”

Greg Smith, on sharing work early

A teacher with a company to learn

The course creator now had to become an employer. As the team grew, the questions changed from how to win a customer to how to hire, delegate and keep people moving in a shared direction. Solving yesterday’s problem did not confer much immunity from tomorrow’s.

Smith’s description of the CEO’s job leaves room for that discomfort. He talks about evolving with the organization and receiving feedback from the people around him. Colleagues have to feel comfortable telling the leader what they see. Respond badly, and an important source of information dries up.

He also talks about equanimity: keeping a level head when circumstances become difficult. It is a quality he says he works on, rather than a virtue he claims to have permanently installed. For someone selling education software, admitting there is still homework seems appropriate.

His reading habits have their own operational adjustments. He has described preferring paperbacks, then shifting to a Kindle and synchronized audiobooks so he could continue a book by listening. His interests include management, leadership, strategy and the construction of useful products.

Away from the company, he has spoken about kiteboarding, campfires, board games and time with his family. The games have a childhood precedent: he and a friend once made a marble-racing course on a backyard hill, complete with jumps and tunnels. Other neighbourhood children came to race. A small audience, a constructed experience, a reason to return.

The bell rings. The homework continues.

On April 27, 2021, Thinkific became a public company on the Toronto Stock Exchange, trading as THNC. Smith’s announcement kept returning to what customers had built. During 2020, they had taught more than 21 million students and earned more than US$275 million in tracked direct course sales.

The listing gave the company resources to invest further in its product. Smith wrote about building an organization that could endure, with customers retaining control of their businesses and delivering useful learning experiences. The ambitions had grown considerably since the first online LSAT lessons.

He also found another role for himself: interviewer. In February 2024, Thinkific launched Unique Genius: The Business of Creators, with Smith hosting conversations about how people turn their expertise and audiences into businesses. Its opening episode featured creator and former YouTube employee John Youshaei.

That project fits a recurring interest in his story. He likes hearing how another person has made a business work, then asking what someone else could learn from it. A customer, a founder and a podcast guest can each become the teacher.

By June 2025, his written product vision put community, engagement and easier scaling at the centre of Thinkific’s plans. More content was becoming available through AI. Smith argued that human connection and useful outcomes would matter as learners chose where to spend their attention. The plan included discussions within lessons, better ways to keep learners involved, and tools for more complicated businesses.

A larger classroom, harder decisions

In April 2026, Smith took direct oversight of Thinkific’s product and technology teams after Ryan Donovan’s departure. The stated purpose was faster AI-driven development and shorter decision paths. The founder who once needed his brother to build course software was now taking closer responsibility for a much larger technical organization.

September brought a concrete addition. Thinkific and Articulate announced an integration allowing eligible joint customers to publish Articulate 360 AI content directly to Thinkific Plus in one click. For training teams, that replaced a routine of exporting, repackaging and uploading material again whenever it changed.

It is an ordinary sort of frustration, and therefore a recognizable one in Smith’s story. A person has something worth teaching. The machinery consumes time that could go into the teaching. Removing those steps remains a product opportunity, even when the customer has become an organization with many authors and many learners.

Later that month came a more difficult decision. On September 23, Thinkific announced a reorganization focused on Plus, its offering for mid-market and enterprise organizations. It eliminated positions affecting 96 employees. The company projected approximately US$19 million in gross annualized savings and targeted free cash flow margins of at least 25% in fiscal 2027. Those were expectations, with the results still ahead.

That change belongs alongside the course origin and the stock-market milestone. A public company’s decisions carry consequences for people who helped build it. Smith said the move was intended to support further investment and improve the business’s discipline; he also acknowledged the contributions of departing colleagues.

The original classroom problem was relatively easy to state: too many repeated explanations, too few hours, too few seats. Thinkific’s next problem involves choosing where a larger business should concentrate its effort. Smith has spent years helping other people turn knowledge into something useful. He is still being asked to do the same with his own.