Shawn Freeman – Founder of TWT Group

It’s only a failure if you don’t learn from it. In that case, I’d like to say I’ve never failed. I’ve made mistakes, but I’ve always learned something.

Shawn Freeman is an entrepreneur, a personable geek, and the founder of IT services company TWT Group Inc. in Calgary, Canada. He founded the company to make IT simple instead of infuriating and believes it should be the easiest part of anyone’s day.

Shawn is passionate about exceptional IT services and being better, faster, and more affordable than the big guys. After completing a degree in computer science at the University of Calgary, he worked in IT for several big companies before starting his own shop in 2009. TWT has seen significant growth since its inception and is now serving more than 100 clients.

Shawn’s experience is broad. He’s answered tech support questions at IT help desks and worked on a large team upgrading an enterprise accounting system. But he’s never let the corporate ladder dictate his path to doing what he loves.

A regular contributor to IT and tech publications, Shawn offers perspectives on cloud solutions and cross-border data security, as well as interviews with industry leaders in Canada and the U.S. He’s also an active member of the Entrepreneurs’ Organization.

Shawn doesn’t believe in overhead. Instead of sitting behind a desk in an office, he visits clients. His office is his living room during the winter, his patio during the summer, and his favorite coffee shop no matter the season.

As a travel fiend, Shawn hits the road often, parking his laptop on the beach in Mexico and on the patio in Palm Springs, California. He generously lends his IT skills to several nonprofit organizations in Calgary, including Youth Central in the Kahanoff Conference Centre.

Where did the idea for TWT Group Inc. come from?

Officially, TWT stands for technology, wisdom, and trust, which are the key tenets of our business. But that’s not how I came up with the name. It originally stood for Tuesday, Wednesday, Thursday, which are the only days I believe anyone should work each week.

What does your typical day look like, and how do you make it productive?

I spend my days seeing clients, having meetings, chatting with my employees, going to spin classes, and enjoying lunch with people I admire.

I always plan each day the day before. I have a variety of rules that I follow (like no meetings before 10 a.m.) to make sure my mornings are always productive.

How do you bring ideas to life?

My first step is to consult the small group of people I use as sounding boards. They always make me think about ideas from different perspectives. If the idea still sounds good, I do some more thinking.

I then consider the risks and the worst-case scenario and ask myself if I can live with them. If I can’t, I don’t pursue the idea.

Once I’ve committed to bringing my idea to life, I loop in my team and delegate tasks according to their strengths.

As soon as possible, I like to review the initial results of my idea and make sure it’s still sound. I never get so invested in an idea that I can’t call it off if it’s clearly failing.

What’s one trend that really excites you?

I’m excited that IT is cool now. People who used to ignore IT now know what a huge role effective technology plays in running a successful business.

I also think this renewed interest in IT will lead to the end of the IT department altogether. With the proliferation of cloud-based tools and apps, the IT department will become irrelevant. The functionality and accessibility of tools like Salesforce and FreshBooks are taking away their utility.

Using any of these, and using them well, is as simple as signing up, logging in, and getting to work. They’re mobile-accessible and updated in real time, and they feature their own security.

I’m excited to help businesses navigate this new world.

What is one habit of yours that makes you more productive as an entrepreneur?

I delegate. I work with a talented team of people who have abilities that I don’t. I achieve more by giving others the opportunity to play to their strengths.

What was the worst job you ever had and what did you learn from it?

I once worked at A&W Restaurants. I learned that I never wanted to work in fast food again and needed to aim higher.

If you were to start again, what would you do differently?

I would start my own company while still in university rather than jump into a job after I graduated.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else does?

I always look at ways I can do better. I try new things, but if they don’t work, I don’t do them again. I make mistakes, but I don’t repeat them. I always ask others for suggestions and use those to improve.

What is one strategy that has helped you grow your business? Please explain how.

I’ve focused on developing relationships instead of simply signing contracts. This shows potential clients — and anyone I come into contact with — that I value them as individuals, not just people who could help my business. If they become clients, we already have a solid relationship established, which means we’ll communicate better and respect each other.

What is one failure you had as an entrepreneur, and how did you overcome it?

It’s only a failure if you don’t learn from it. In that case, I’d like to say I’ve never failed. I’ve made mistakes, but I’ve always learned something.

What is one business idea that you’re willing to give away to our readers?

Start an IT-related business that doesn’t come with any startup costs. All you need to do is ensure that you make good products or fix problems for people. You can start a business like this from anywhere in the world.

What is the best $100 you recently spent? What and why?

The best $100 I’ve spent is on lunch with someone I look up to. There’s always a 1,000 percent ROI.

What software and web services do you use? What do you love about them?

I use Slack (a team communication platform), Expensify (an expense-tracking system), Trello (a project management tool), Positionly (SEO software), and MailChimp (an e-newsletter service). I love these services because they connect me to my remote team, allow me to easily communicate with clients, and let me track the reach and effectiveness of my website.

These services are all based in the cloud, so I can access them anywhere. They’re also easy to install and drop if they’re no longer useful.

What is the one book that you recommend our community should read and why?

I would recommend “Delivering Happiness” by Tony Hsieh. It details an entrepreneur’s journey and how he found real happiness, which I can relate to.

What people have influenced your thinking and might be of interest to others?

Robert Hart:

Vince Fowler:


George Fink:


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TWT Group on Twitter: @TWTGroupInc