This Side Hustle Spotlight Q&A features Greg Smith, 47, of Vancouver, British Columbia. Smith was in law school working part-time as an LSAT tutor when he turned his expertise into an online course — then realized it could become an even bigger business. Today, Smith is the founder of Thinkific, a learning platform that helps more than 77,000 entrepreneurs, small business owners and subject matter experts turn their knowledge into digital classes that make them money. Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Thinkific. Greg Smith.}

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What was your day job or primary occupation when you started LSAT tutoring? How much money did you earn from LSAT tutoring?
Back in 2005, I was in law school and started tutoring LSAT prep part-time to help pay off my student loans. I started offering in-person courses as well, and while the feedback from students was excellent, I was only able to reach a limited number of people in person, and it was a lot of hours going into tutoring and teaching.

I went online to reach more people and move away from the limitation of dollars per hour. Initially, it was just a blog, but eventually, I decided to package what I was teaching into an online course for $29. That simple idea changed everything. Within a few years, we were earning around $10,000 a month from it and having a positive impact on hundreds of students. It was my first real glimpse into how powerful it can be when you turn your knowledge into a business.

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How did that inspire Thinkific?
When I set out to build an online course, I went looking for software with a few important criteria. It had to have an exceptional learning experience, strong commerce functionality, so I could charge for my training, and allow me to control the brand, so I could build my own business on my own site.

There wasn’t a solution out there that met these needs, so my brother Matt and I built our own. Over time, other experts and businesses saw this and asked us if we could help them build their own branded online learning platforms. In 2012, we’d heard this request so many times that we set out to build Thinkific as a solution for others to do what we’ve done: create and sell beautiful learning experiences under their own brand that they could sell to others.

What were some of the first steps you took to get Thinkific off the ground?
In the early days, we had to do a lot of scrappy, non-scalable things to get going. Today, people want easy-to-use self-service software, with a lot of AI doing the work for you to get set up. Back then, we’d call people up and do anything it took to get them set up. Not just building their course site — we’d film courses for them, and in some cases, I even ended up as a customer’s instructor or sales and marketing person, anything to get a customer and help them succeed.

In the beginning, we pieced together a custom solution using a mix of third-party software tools and some of our own code. It worked for us, but it was clunky, expensive and definitely not something we could hand off to others.

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That’s when we realized the real opportunity wasn’t just in building courses for people; it was in giving them the tools to do it themselves. So the first step was creating Thinkific as an all-in-one platform that made it easy for any expert or business to build, market and scale their own learning business.

Most software customers just sign up with a credit card, and it takes minutes to get going, but we didn’t have an automated way to collect payments, so we’d often do a bunch of work for them and then call up to get their payment info over the phone. Definitely messy, but it worked, and we learned a ton about our customers and what they needed to succeed. We then baked that into our software so we could help thousands instead of just dozens.

We haven’t lost those lessons. To this day, I’ll hop on at least one call a week with a customer to learn more about their business directly and see what we can do to help them. Now we have over 35,000 businesses generating billions in sales on Thinkific.

How much money/investment did it take to launch?
We initially funded Thinkific with the proceeds from our online LSAT course business, just a few thousand dollars a month, and covered the rest by putting expenses on our credit cards.

As things started to take shape, we secured a small loan and a $50,000 investment from family members (who’ve been very well repaid since). From there, early revenue helped us stay profitable while we slowly grew.

Even with that profitability, we decided to raise $600,000 from Rhino Ventures and a few tech founders, and that extra capital gave us the confidence to hire and make bigger bets.

As the business scaled, we raised additional rounds, first $1 million, then $2 million, and years later, we secured about $20 million, mostly secondary for founders and early shareholders. In 2021, we capped it off with our IPO, raising $184 million.

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Are there any free or paid resources that have been especially helpful for you in starting and running Thinkific?
One of the most valuable “resources” for me has always been our customers. I make it a priority to talk to them every week. No book or podcast can replace the insights you get from hearing what people actually need, where they’re struggling and what’s working for them on your platform. Nothing beats listening closely to your own customers. They’ll tell you exactly how to build a better business if you take the time to ask.

If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
One thing I’d have done differently right out of the gate would be building an audience or marketing around our chosen area. Instead, we focused on building a product to sell, but that meant when it came time to sell it, we had to search for every single customer, and we were starting from scratch.

I’ve seen other companies build the audience early, and it means when they have something to launch or sell, they have at least a small audience who’s ready to buy. Plus, it means more potential customers to talk to, so you can learn and iterate faster — which means a better first product.

When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
One of the most challenging and ultimately most important lessons has been staying relentlessly focused on customer success as our north star. It’s easy to get caught up in features, growth metrics or even customer service wins, but none of that matters if our customers aren’t actually succeeding with our product.

At the end of the day, our job is to build something that helps businesses sell more of their own products and services. Everything else, like strategy, support and marketing, has to ladder up to that goal. Keeping that focus clear has been both the biggest challenge and the key to building a lasting business.

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Can you recall a specific instance when something went very wrong? How did you fix it?
Early on, we set revenue-based goals that led us to chase quick wins — one-off campaigns that spiked revenue but didn’t create lasting value. It looked good in the short term, but it wasn’t sustainable. Once we shifted our focus to building evergreen initiatives that serve customers long-term, it drove recurring results. It was a mindset change: Revenue keeps the business alive, but meaningful impact is what makes it thrive.

The lesson was that a team-wide obsession with helping our customers succeed meant everything else pretty much took care of itself.

What does growth and revenue look like now?
When we first started, we saw sporadic revenue very early on. It took us about two to three years to get to actual MRR — monthly recurring revenue, where customers signed up on their own, and we billed their card every month. This is ridiculously slow by today’s standards, and I’d expect that if we started today, we’d be at MRR within three to six months or less.

Once we reached it, growth accelerated quickly. We doubled revenue every two to three months at first, then leveled into a steady 60–70% annual growth rate, with a Covid surge in 2020 followed by a natural slowdown as the market normalized.

What do you enjoy most about running this business?
Hearing directly from the businesses and entrepreneurs who use Thinkific. Every week, I talk with people turning their ideas into real businesses, and seeing how the platform helps them reach and impact others is incredibly rewarding. It’s a reminder that our work only matters if it helps our customers succeed.

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What is your best piece of specific, actionable business advice?
Focus on output, not input. Early in building my company, I was frustrated to learn some team members were pouring energy into side hustles and even new startups. I was maxing out my credit card to cover salaries, and I couldn’t be sure how they were spending their time. Then my cofounder said this to me: “Why does it matter how they spend their time, if they’re delivering what we need?”

After that, I stopped managing hours and started managing outcomes. We built an output-first culture, one rooted in trust, clear expectations and accountability to results. For any entrepreneur, that’s the shift that scales. Set goals together, coach rather than police your team, and measure what gets done and the impact it has on your customers and business.