Ryan Shupak and Paul Arlin: Today’s Notable Young Entrepreneurs

Today’s Notable Young Entrepreneurs are Ryan Shupak and Paul Arlin, who created the Jiffy app to fill a gap between homeowners and home service professionals. We caught up with the duo to find out what advice they’d share with other young professionals and where they wine and dine in Toronto…



1. Describe what you do in less than 140 characters. Go.
Jiffy takes the hassle out of home maintenance by connecting homeowners with great service professionals in real time, currently in over 20 categories.

2. What was the inspiration for your career route?
Ryan: After working in investment banking for almost three years I decided that I wanted to build a business that uses technology to solve everyday problems.

Paul: When I moved into my first house two years ago, it didn’t make sense why there wasn’t an app to instantly connect with home service professionals. So we decided to create one.

3. What is the most memorable milestone in your career so far?
Ryan: Taking the leap from a steady job to working on something I’m extremely passionate about.

Paul: Holding the #1 spot on the ping-pong ladder in offices I’ve worked in.

4. Where do you see yourself in 5 years, 10 years, 20 years?
Ryan: Growing Jiffy for the foreseeable future. In 10 or 20 years I’d love to have a leadership role in the community, whether as a mentor to younger entrepreneurs, with charities, or even in politics.

Paul: Expanding Jiffy to new cities, increasing how many services we offer, and narrowing our window for on-demand appointments. Every job ordered through Jiffy to date has made someone’s life easier and more efficient – that’s cool. I’d like for millions of homeowners to experience it.

5. Do you have any advice for other young professionals?
Ryan: Take chances – the worst-case scenario is probably not nearly as bad as you think it is.

Paul: Pick your partners wisely. Team up with people who have different, but complementary skills to yours. 

6. Do you support any charities? If so, which one(s) and why is it (or they) important to you?
Jiffy has sponsored local causes in our community including school fairs and a squirt hockey team; we continue to look for interesting ways to give back to the community.

7. What does the word notable mean to you?
Ryan: Creating products that make people’s lives easier.

Paul: Being involved in something that matters.


1. Where is your favourite place to wine/ dine in your city and why?
Ryan: Ferraro – talk about efficiency.

Paul: Rasa on Harbord. Best patio, cool atmosphere, and delicious.

2. What’s the most visited website on your Internet browser?
Ryan: CBS fantasy football

Paul: Gmail

3. Who’s one person you think everyone should be following on social media?
@JiffyOnDemand or Dan Debow – nothing beats his pro-Uber rants.

4. What’s your favourite cocktail?
Ryan: Negroni Spagliato

Paul: A Caesar.

5. What gives you the greatest FOMO?
Ryan: Canoe trips.

Paul: Not being involved in an iMessage group.

6. What would be your last meal? And don’t hold back…
Ryan: San Fran’s veal sandwich

Paul: Duff’s wings (super hot).

7. What’s your guiltiest pleasure?
Ryan: Chips – I’d make Mark Messier a rich man.

Paul: Reading (my wife’s) various tabloid magazines on vacation.