Creators of Toronto | Kyle Trattner & James Engelsman

By Mauricio Poveda June 16, 2015

This week, we’re excited to feature Kyle Trattner and James Engelsman of Tickld, a user-based content sharing website. The pair aimed to create a place where they could “spread laughter and cure boredom”. As more people joined the fun, Kyle and James ended up with a community of thousands, all contributing entertaining content from incredible photos to hilarious quotes every day. Not only does their site receive thousands of posts daily, they just hit 1m likes on Facebook! Read on to learn more about their story.

Creators of Toronto | Kyle Trattner & James Engelsman

Tell us a bit about your background. What career/educational path led you to where you are now?

Kyle:  I’m a recent law graduate from The University of Nottingham in Nottingham, United Kingdom.  I lived and studied in Nottingham for three years, which is where James and I first built our friendship and Tickld followed.  Prior to Nottingham, I studied at McMaster University in Hamilton, Ontario, where I earned a bachelor’s degree in history.

In the past decade I’ve worked as a computer technician, project manager at a furniture company, maintenance at a summer day camp, in various roles at an overnight camp and as a swim instructor.

I can’t give credit to any single degree or job for preparing me for Tickld.  The collective experience is important.  Raking leaves for weeks on end has built as much character as writing a 20,000 word dissertation.  Tickld has proven to be about patience, perseverance and a capacity for constant learning.

James: I’m a recent American studies drop out from the University Of Nottingham. I spent most of my university days from the very start working with Kyle on many Project Xs and avoiding lectures and seminars to do so. So it would be unfair to credit Nottingham’s American history curriculum with any particular skillset I may have. I would however, credit the environment it allowed me to manifest mine and Kyle’s ‘preneurs’ in.

Like Kyle says, Tickld has proven to be about patience, perseverance and a capacity for constant learning. And more importantly, realizing that I possess none of these traits.

What made you want to start Tickld?

Kyle:  Independence.  I wanted to set my own schedule, be my own boss.  I’ve since discovered that’s not a thing.  I now work incredibly long hours and I’m answerable to more people than I ever thought possible.  In any case, James and I are very proud of the community we’ve assembled.  We hope to be working in service of the Tickld Community for a very long time.

James: Tickld started with the idea that if we built a brand around humour content on the web, it would have a long lasting, engaged community that would provide Kyle and I with food on the table as well as some fresh pages of fun-filled internet to wake up to. Had we known the chaos this would bring into our lives, we would probably have started watching our red meat intake earlier.

What was your biggest challenge when you were starting your project?

Kyle:  Building the technology to execute our ideas.  I think this still remains one of the biggest challenges today, although for different reasons.  At the outset, I was Tickld’s sole developer.  My knowledge and skill was limited; accordingly, the website wasn’t exceptional.  We hired talented people to help us fulfill our vision.  It was another challenge to find the right people.  The challenge today is balancing limited development resources to build the best product we can while reacting to new problems that crop up daily.

James: To answer this would only be to echo Kyle’s words. I would add though, that a further pressure was that we would have to cling to the hope that the technologies we decided to devote our time to would still have their place in the market by the time that they were completed. This space moves fast, and this is still a big decision making point that we experience today.

What is your favourite part of Tickld?

Kyle:  The user-generated content.  I love seeing people create really imaginative things with the tools we’ve built for Tickld.

James: Watching the users of the site become more than just internet penpals, and hearing about how they are flying across continents to visit each other.

What is one app you cannot live without?

Kyle:  Other than Tickld, Spotify.  I’m terrible at picking music.  I love the “Mood” feature.  Another one would be, Starbucks.  I think I use that app with embarrassing frequency.

James: Spotify as well. I don’t remember the last time I used iTunes. Spotify is still the best $10 I spend a month.

Do you have any advice for future entrepreneurs looking to make their mark? 

James: Don’t fear the big guys. They are far more scared of the underdogs. As a new person to the entrepreneur world, you can move faster and with a wider lense than companies that are limited in their verticals.

Kyle:  You don’t have all the answers!  If you’re going to be successful, surround yourself with talented people.  I think the best entrepreneurs will always have a talent for picking talent.