Jennifer Hollett is Doing Something About It

Jennifer Hollett at Boxcar Social. You can find more on Jenn at

Jennifer Hollett at Boxcar Social. You can find more on Jenn at

I sat down across from Jennifer Hollett in my favorite coffee shop, Boxcar Social in the east end. As I walked in, I remembered the first time I met Jennifer. I was a 21 year old grad student and I didn’t want Rob Ford to get elected as Toronto’s mayor, so I signed up to volunteer for Olivia Chow’s campaign. Jennifer was my bosses boss on the campaign, a force of nature to be reckoned with, determined to put someone in office who had a good brain and a solid heart. I was immediately on board to follow this woman. 

We didn’t win that year, but at least we did something about it

Doing something about it is a theme of Jennifer’s life and career.

Fast forward 10 years, and we’re having coffee on a warm summer afternoon in Toronto— and Jennifer has been busy doing a lot about it. 

Her career started at Sony Music. She got that job with a feminist bossmove. She told me the story of a guy she worked at the radio station at Concordia University seeing the job posting, and declaring with a sense of 20 year old brotato entitlement that the role at Sony was his job. He was going to get it, and that was it. Jennifer was not having any of that nonsense, so she applied for the gig— and got it

She worked at Sony setting up websites for artists like our Queen Celine, before taking a role on television— where she eventually worked her way up to VJing Much Music (my teenage dream job). There she interviewed musicians and Prime Ministers. Also, the other Queen (Beyonce), twice. No big deal. She then became an award winning journalist for the CBC and CTV, but that didn’t come up over our coffee.

I wanted to talk about politics, and how Jennifer got so involved. She told me that in a backyard on a swing set one day, Jennifer was having a conversation with a friend about the lack of good women and diverse candidates in Canadian politics. They were complaining, saying that candidates need to be younger, more accessible, and the barriers designed to keep women and people of colour out of the political process need to be removed. In that moment, they knew they had to do something about it.

Jennifer left her job in journalism in 2011 to learn more about these issues, and how she could help. Casually, she chose a Masters of Public Policy at Harvard fucking University. Cool cool cool cool cool dope dope dope dope dope dope. She decided to go hard, in a class with Ministers, politicians, and people who had worked on Barack Obama’s campaign.

I came out not just believing I could do it, but that I had to. Politics is too important to be left to the politicians.


Before coming back to Canada, Jennifer had an idea while taking a class at MIT for an app that let’s users see who is funding political ads called SuperPac App. Dark money is a toxic force in American politics, and so often we don’t know who is really behind the political attack ads we see. So she built it. She calls it “Shazam for politics”. Doing something about it. Journalist, to Harvard student, to Startup Founder for good *can she get any more impressive?*

You can’t wish the world to be the way it should— you have to get involved.

When Jennifer came back to Canada, she wanted to keep her swing set promise, so she decided to run for MP of University-Rosedale in Toronto in 2015. She created a community driven campaign, and vowed to do politics differently. Her campaign was fun, bold, and optimistic. She showed the fuck up, and went door to door talking about women’s issues, and childcare, and justice. She did something about it. They didn’t win, but they did something— and they’re incredibly proud of that. They should be.

Go into these opportunities and be open to the people you meet and what can come of it. I started in music and ended up in politics.

Jennifer took a job as the Head of News and Government at Twitter Canada, and quit that job last year to run for City Council in Toronto. Jennifer launched her campaign to champion local issues. Some of you remember what Doug Ford did to our city, cutting our City Council Wards by half in the middle of the election cycle. Ford’s Bill 5 effectively tampered with our election system, and reduced our political representation. Jennifer had quit her job to run for a position Ford cut. 

Politics is risky, it’s unpredictable, and it’s not for the faint of heart.

They’re still challenging Bill 5 in the courts. You have to brace yourself to lose, to be attacked, to ask people for money. 

Candidates get over those barriers because of what’s possible. You can stop complaining to your friends about rent being too damn high, you can actually do something about it. Ask yourself: What is it I can do?


I asked Jennifer for her advice for women who feel angry, and who feel helpless to what’s going on. I asked her what we can do...

Anger is normal, it’s healthy, if you’re not angry you’re not paying attention. Especially for women, and for racialized women we need to get angry, and then we need to get organized.

How though? This is the question so many young people ask me, and Jennifer was the perfect person to answer it. She has a formula:

  1. Vote. Seems straightforward enough.

  2. Take friends and family with you to vote. Ok, now it’s a party.

  3. Find a candidate or a party you like. Then, make a donation. Then, show up and ask to help. How? Jennifer says the easiest way is to find their website or Facebook page or Twitter account, and fill out the form to volunteer. If for some reason they don’t get back to you, they’re busy, push again. If they have a campaign office, go on in and say “Hi, I’m new to politics and I’d like to get involved.” It sounds scary, but Jennifer promises, they will do a dance of joy! 

    I love to hear when women want to run. I always encourage women to run, and when they do, to go all out.

    We should all take a page out of Jennifer’s very interesting book. We should all say yes to our own curiosity. We shouldn’t lament when things in our community and our politics don’t serve us, we should get involved. We can all do something.