Doers Across Canada: Marsha Druker and FuckUp Nights Toronto

Meet Marsha Drucker: entrepreneur, proud Toronto resident, and professional f#ckup.

Taking risks is a major part of entrepreneurship, but it’s how you handle failure that defines you as a doer. Canadian freelancer Marsha Druker leaned into the concept that what doesn’t kill you makes you stronger to create Fuckup Nights Toronto, a safe space/speaker series where doers can share stories and embrace professional failures as an opportunity for growth. Learn more about Marsha’s business journey and how she learned to stop worrying and love professional bombs below—and tune in all week as we meet more #DoersAcrossCanada like Marsha! 

Tell us a little about you. Who you are, where you’re from, what you do in Toronto.

I run Fuckup Nights Toronto, a speaker series and community that shares stories of professional failure. My days are spent talking to entrepreneurs about their learnings from businesses/projects that went wrong, planning monthly and themed events, and working with my team and partners to grow our community. I also freelance and work with startups on content marketing and PR projects.

Before getting into community building, I held various marketing and PR roles in companies ranging from consumer packaged goods to tech startups. The most formative part of my life thus far was the time I spent living abroad in Tel Aviv, Israel where I worked as a Content Marketing Manager at (acquired by Fiverr). My experience living and working abroad inspired me to start Fuckup Nights Toronto.

So…Fuckup Nights Toronto. What inspired you to create a community focused on sharing and dissecting failure?

Fuckup Nights Toronto is part of a global movement that happens in 250+ cities and 80+ countries.

I went to my first Fuckup Night in Tel Aviv. I’ve never seen people share stories of failure so openly. My career hasn’t really been a straight line and I’m always open to trying new things, so the event really resonated with me and I felt like I found my tribe there.

When I returned home to Toronto, I was shocked to find that a Fuckup Nights chapter didn’t exist here yet and decided to start it myself. I figured it would be pretty ironic if I manage to fail at something called “Fuckup Nights” (I’ve never planned an event or done any community building before), but, I went for it anyway, and that’s how Fuckup Nights Toronto came to be.

Why do you think it is important to embrace failure as an entrepreneur?

For many people admitting failure in business is still somewhat of a taboo. I think this is especially prevalent in a city like Toronto. We have lots of new businesses popping up, but not the same “fail-until-you-make-it” culture of Silicon Valley.

Unfiltered discussions about failure are healthy for anyone, but can be particularly cathartic for fellow entrepreneurs. Failure is where you are going to learn the most. It’s where your resilience is going to be tested and where you’ll be able to learn the lessons you need to succeed.

At Fuckup Nights, we’re helping people talk about an uncomfortable subject and normalizing it, while doing it in a way that’s fun and accessible.

Do you mind sharing one business failure—and one success—of your own?

My biggest fuckup with Fuckup Nights by far was trying to do it alone.

I thought it was a good idea to plan and execute the Fuckup Nights Toronto launch event entirely on my own, while starting a new job and commuting to downtown, apartment hunting, and moving.

It was a recipe for burnout.

I learned that you can definitely plan a great event on your own, but you’ll never build a community without a team.

After the success of the first event, volunteer requests started flooding in. But even then, it took me far too long to give up control and delegate tasks (after all, it was my baby). The key to me giving up control was finding people who compliment my skill-set and are knowledgeable in areas I’m not.

Now, I’m proud to say that I have a passionate team of “fuckuppers” who are dedicated to giving failure the spotlight it deserves. People who are way more talented than I am, who bring fresh ideas, and who help me shape and execute a vision for everything that these events and community can be. And I think we’ve only scratched the surface.

Fuckup Nights Toronto celebrated its one year anniversary in March 2018 at a sold out event with 500+ entrepreneurial community members, a concert, and four incredible speakers. I’d call that a big success, and there’s no way I could have done it without my team.

What drives you as an entrepreneur? Why do you do what you do?

There are so many moving pieces and things outside your control when it comes to running events. It’s very stressful, to say the least.

But it’s all worthwhile when I look out into the audience and see people’s faces light up during the talks. I’ll have people reach out after and say how it impacted them and changed their perspective on failure. Some come out to an event in the middle of their own failure to see there’s always light at the end of the tunnel. People have even met co-founders, mentors, and gotten new jobs through the community.

These types of success stories are what drives me and keeps me encouraged. Ultimately, I know I’m building something that’s bigger than myself.

How did you grow the Fuckup Nights community into the robust speaker series it is today?

I think it was the perfect storm just waiting to happen. Toronto is an ideal city for meetups. There are so many different events in tech, sales, marketing, health, design – you name it, there’s a meetup for it. But there wasn’t anything anything authentic and raw like Fuckup Nights. As soon as it existed it resonated.

Bringing the right partners onboard was major. Having organizations like Shopify, DMZ, WeWork, TribalScale, etc. behind the community brings credibility, presence, and helps attract great speakers.

People attend each event to hear three speakers share their failures and lessons learned. Each speaker gets 7 minutes and 10 images to tell their story. Our events allow people to talk with speakers openly, to ask questions and learn from their failures.

Our speakers come from all walks of life and industries. This, in turn, draws a really diverse group of people to the events. At every event you can expect to find entrepreneurs, tech/startup folks, creatives, corporates, and everyone in-between.

On the digital side of things, we have a blog where we publish guest posts, interviews, local and global stories of failure, fuckup lessons from our events, and collect epic failure stories from around the web. On our social channels, we focus on curating and sharing relevant content, with a big focus on video content from our events and speakers.

We’re seeing social engagement and following steadily rise and our events get sold out and waitlisted. We practice what we preach and are the first to admit and share our own failures, which our community members really appreciate.

I’m always looking for ways to bring the community to the next level. It’s not necessarily about larger events – I believe that events with around 150-180 people are ideal for our mission. Rather, I’m exploring avenues like merch, themed events, private events, partnering with universities and conferences, and expanding to Waterloo.

What do you think makes doers in Canada (and Toronto in particular) special?

Through Fuckup Nights, I’m really fortunate to have an avenue to approach and hear from incredible Toronto doers on a daily basis. I’m inspired by their passion, determination, and resilience.

It’s true what people say about Canadians being some of the nicest people around. What that means for the entrepreneurial community is that we’re collaborative, supportive, and open.

Yes, we’re polite, but don’t underestimate us! We hustle and go after our dreams.

What do you love about the Toronto entrepreneurial community?

Toronto is having a moment – I truly believe we’re on the cusp of being one of the strongest entrepreneurial ecosystems in the world. It’s an exciting time to build a company here, not to mention being a great place to live and play.

I might be biased, but one of the things I love the most are all the communities that entrepreneurs have access to here. Being an entrepreneur or freelancer can be a lonely road full of ups and downs. Communities like Fuckup Nights, Creative Mornings, Tech Toronto, etc. make it easier to connect with and learn from others in the same boat.

What excites you most about the future of work?

I’m excited about the flexibility I’m seeing in the future of work. You don’t need to quit your full-time job to become an entrepreneur. With the technology and connectivity we have today, it’s never been easier to build a side hustle, freelance, and find interesting opportunities.

It’s exciting to see outdated concepts of work be challenged, remote and flexible work options becoming more common, and for the Gig and freelance economy being recognized as a robust option for building a career.

Want to know more about Marsha and Fuck Up Nights Toronto? Follow her @MarshaDruker and @FuckupNightsTO (Insta + Twitter), and ask her in the comments below! 

Hannah Curran
Hannah Curran is Fiverr's Social Media and Content Manager. Originally from Connecticut, she lives in California and works out of our San Francisco office. Have an idea for the Fiverr blog? Connect with her on LinkedIn.
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