Life Beyond the Law Firm: An Interview With Tech Entrepreneur Greg Smith

Greg Smith, co-founder of Thinkific.com

When lawyer-turned-entrepreneur Greg Smith quit practicing law to start tech company Thinkific, he quickly learned that following his dream was going to take more hard work and a lot more risk than anything he’d encountered before.

Many lawyers find the business world beyond their law firm more enticing than the business of law. I recently asked Greg to share how his legal experience has influenced his foray into the entrepreneurial realm.

Q. What spurred you to leave the comforts of a big law firm and start a tech company?

I loved practicing law at both firms I worked with. The people, staff and clients were all great. Even the hours didn’t bother me! I enjoyed working in intense sprints and still do that today.

In the end though, I was more passionate about being an entrepreneur than about practicing law. I remember looking at my corporate clients and thinking, “I love helping you, but I’d probably be even happier if I was doing what you’re doing.”

Q. What sparked the idea for Thinkific?

When I started law school at the University of British Columbia, I taught an LSAT preparation course in a classroom. I created an online version of it with help from my brother, who is a software developer. Over time, the online became quite popular – people all over the LSAT taking world were learning from me. Also, people teaching in other areas such as GMAT preparation and Excel were calling to ask how I had setup the online course.

The more inquiries I received about how I created my course, the more I realized that these steps – technology and marketing – were a widespread challenge. So, we built a platform that allows anyone to go out and distribute their own online courses. We set it up so that people can launch their own course or training site under their own brand. .

Our clients can create courses to educate their clients or staff, generate leads, to support a community or even sell them for revenue.

Q. How has your experience as a lawyer influenced how you lead your company?

When I practiced law, I was constantly exposed to new industries and different management styles. I probably worked on more corporate transactions than most CEOs get to see in a career. And of course, in running a tech company or any company, legal issues constantly come up.

There is dangerous side effect of being a lawyer and running your business, though. As a lawyer, I would typically identify all the risks, all the ways a deal could go sideways, and then try to account for or address them. As an entrepreneur, I had to accept or not address some risks in order to complete some deals.

These were the decisions I had previously left for my clients to make after presenting them with the risks and options; now I know what that feels like.

Most entrepreneurs are risk-friendly, but when it comes to legal agreements, I tend to be less so. Non-disclosure agreements are a good example. People tend to throw them around like they mean nothing, but knowing the potential strength of an NDA always makes me shy away from signing them, in some cases my reluctance may have lost deals that otherwise would have gone through.

Q. Do you have any advice for lawyers who might be considering a similar career switch? What should they be prepared for?

The idea is nothing. It’s all in the execution. There are very few overnight successes. We’ve been at it for 3.5 years and things are going really well, but you should plan for lean times in the early years.

You can’t really outsource the execution of your business strategy or take care of it in your spare time while you work full time at your regular job because there is so much riding on getting it right in the early days (at least in the tech business). Failure is still common for most startups; most failure happens in the first year or two and it all depends on your execution.

It’s amazing how much time little administrative tasks can take up. I have an awesome team now, but in the early days it was just my brother and me. We were doing EVERYTHING, from taking out the garbage to setting up banking for the company.

Elon Musk has said “being and entrepreneur is like chewing glass while staring into the abyss”. Staring into the abyss because you’re constantly looking six months ahead to the potential destruction and bankruptcy of your company and chewing glass because you have to do all the things you don’t want to do. Luckily were through much of the Abyss stage now and but there’s still a lot of glass to chew.

There will be a huge shock to your salary. Don’t underestimate it. I gave a presentation to Startup Canada a few years ago where I made jokes about being addicted to a paycheque.. The early days of being an entrepreneur are such a different experience than earning a regular, predictable salary. The payoff can be amazing, but it takes a while to get there.

Greg Smith is a lawyer, instructor and lifelong learner. As a co-founder of Thinkific, he has helped thousands of others create their own online courses and deliver amazing eLearning experiences. When he’s not building his business or spending time with his family, Greg can be found kiteboarding, sitting around a campfire and/or playing boardgames.