Paul Chato Shares Hacks, Laughs & Why Recurring Revenue Beats Dragging Elephants Home

Paul Chato has lived several careers — comedian, television executive, entrepreneur, and now YouTube creator.

I've known Paul for over 10 years. At one point, we both belonged to a weekly business networking group, and when Paul served a term as club President, I got to enjoy his trademark wit and humour at every meeting. Later on, we teamed up to create a small business cartoon strip called Sully's Startup which was so much fun.

In our conversation on The Unsure Entrepreneur Podcast, he spoke openly about the twists and turns that shaped his path. What stands out is not just his creativity, but his willingness to reinvent himself when the moment called for it.

Paul's story begins with comedy. A graduate of the Radio and Television Arts program at Ryerson University, he co-founded the legendary Canadian sketch troupe The Frantics. Their irreverent humor brought audiences cult favorites like Mr. Canoehead (played by Paul) and appearances on Frantic Times, Four on the Floor, and at Just for Laughs.

“Comedy was always a big part of what I wanted to do,” he explains, recalling how he was influenced by British satire, American comics, and even his own family’s show business ties.

From stage to boardroom

In addition to his creative work with The Frantics, Paul wound up handling the business details no one else wanted — including doing Rick Green's tax returns.

“The other three guys had no idea how to fill out their tax forms,” Paul laughs. “I barely had an idea myself, but I was fastidious and logical. So I volunteered to do not just the Frantics’ taxes but the other three guys’ personal taxes as well. I learned a lot about business just by doing everyone else’s returns.”

It gave Paul a head start in understanding numbers — a skill that would serve him later when he launched his own company.

After a decade of performing and writing, Paul made a surprising pivot into the business side of entertainment. He served as head of TV comedy development at CBC where he helped shape Canada’s comedy programming from behind the scenes.

But even in those years, he never lost his entrepreneurial streak.

Building a business before subscriptions were trendy

In 2000, Paul launched Your Web Department, a subscription-based website service that predated Squarespace and Wix.

He and his team built over 2,000 websites and served hundreds of recurring customers. “We made people pay right from the word go,” he says. “We didn't do a freemium model. A lot of people in Silicon Valley who I got in touch with said that was genius.”

Instead of chasing one-off big projects, he embraced the stability of recurring revenue. That shift gave him freedom.

“When you do these big jobs for large clients, you’re basically killing an elephant and dragging it back to the office so everybody can eat. With subscriptions, I don’t have to work for a living. It really feels good.”

Reinventing again on YouTube

Paul's curiosity pulled him into the YouTube world, first through videos about Hackintosh computers. From there, he pivoted into tech commentary and media criticism with his channel Call Me Chato that now has more than 130,000 subscribers.

He later launched aPauling News, a satire channel where he lampoons bizarre headlines.

What make his videos stand out is his insider’s perspective. “I was a former network executive, and my very first video I talked about the fact that I had one job, and that was to keep my job. I didn’t care about the quality of the product. So why are you guys complaining about it? I don’t give a shit.” That blunt honesty struck a chord with YouTube viewers.

YouTube became both a creative outlet and a new stage and one that he recommends for budding entrepreneurs. “People hire you based on who you are as a person, and YouTube is a great way to show your personality,” he told me.

It sure is. Just in time for the new John Candy documentary called I Like Me now out on Prime Video, Paul just posted this very personal story on his YouTube Channel to share how he met his wife Ramona because of John Candy. Enjoy it here.

Lessons for entrepreneurs

Paul’s offers a few lessons for entrepreneurs today.

1. Recurring revenue creates freedom. Aim to build a business system that can pay you regularly, so you don't have to keep chasing new business.

   
   

2. Do it manually at first. He cautions entrepreneurs not to overbuild too soon. “Don’t blow your budget trying to automate it right from the very beginning. Whatever you can do manually, do it manually, even if it’s a pain in the ass. Get your business to the point where it’s intolerable — that’s when you improve the software.”

   
   

3. Listen your way to a sale. “People don’t like to be sold, but you can talk to people at the highest level if you say, I have an idea, you are one of the leaders in this field, would you be willing to give me some advice? They will talk your ear off.”

Another lesson Paul offers is for future employers. "The toughest lesson was realizing your employees are not your friends. Nope. They're not your friends."

The value of finishing what you start

At this stage in his career, Paul is transitioning away from his business, focusing on YouTube, and writing screenplays. Whatever he takes on, you can bet he'll see it through. One of his guiding principles is, “Start something, finish it, sell it, or try to sell it. Complete the circle."

He also gave me this terrific line which I've been sharing on social media: “An entrepreneur is someone who is absolutely certain of success and surprised when it happens.”

Funny, sharp, and useful. Paul Chato’s lessons are a reminder that business doesn’t always start with a grand plan. Sometimes it starts with a sketch, a subscription, or even a tax return.

Listen to the podcast here.