Life Beyond Law: Tech Entrepreneur Greg Smith

When entrepreneur Greg Smith quit practicing law to start a tech company, 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 are enticed to join the business world beyond their law firms. I recently asked Greg 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 then created an online version of it with help from my brother, who is a software developer. Over time, the online version 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 certain steps – technology and marketing – were a widespread challenge. So, we built a platform that allows anyone to launch their own course or training site and distribute it under their own brand.

Our clients create courses to educate their clients or staff, generate leads, to support a community or generate 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. Which aspects of typical law firm business models could evolve to adapt to future markets?

I’ve heard a few law firms announce terrific-sounding programs in the past few years. Firms tend to be really good at putting programs in place and giving women a lot of career opportunities, but if you look at the results – percentage of female partners, for example – you wonder how successful those programs are.

It would be great to get to a place where we could see more equality at the upperlevel positions and pay scales of law firms.

I was recently accepted into a great program for tech companies. When I applied there was a moment where I reconsidered whether I should even the imminent birth of our first child. I worried that the admissions panel might question my commitment to the program for the next six months. I’m sure it had no impact, but just the fact that I hesitated really brought to light what women go through on a regular basis.

I have a female friend who also leads her own tech company. She has a baby on the way and yet we are in such different situations. Even with a great husband, she’ll need to take more time off to care for the baby and she still has to run her company. It’s a lot of pressure (and I’m sure she wouldn’t have it any other way).

Government programs might have some influence on the situation. Access to affordable, high quality childcare is really important. (But I’m definitely not an expert in this area.)

Q. What opportunities should the legal sector be taking advantage of with respect to technology?

Online learning has become much more widely accepted and adopted in the legal sector. There are so many opportunities. You can save on travel. You can offer educational content when people need it rather than booking time away from the office for courses.  Also, the course material doesn’t perish like it does when a live course ends; it can remain accessible long afterwards.

Lawyers have traditionally spoken at events to share knowledge and educate. Often, this leads to new clients, too. But that’s a lot of effort for a one-off event. We’ve seen lawyers repurposing and leveraging those same presentations online to reach a much larger audience. You can do this as lead generation or you could even sell it. In law especially, it’s a starting point to develop a relationship with clients or potential clients.

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.

An abbreviated version of this interview was published on the Canadian legal blog Slaw.ca on August 19, 2015.