Fuckup Nights Toronto Vol. V
Fuckups = experiments = learning
On October 18th, we held our fifth Fuckup Nights Toronto event. This was the fourth time Shopify hosted us in their awesome space, and we were thrilled to be bringing 150+ people together to celebrate failure. Yes, you read right. Our mission is to celebrate failure. Why? One of our speakers, Will Richman, put it best: “Fuckups = experiments = learning.” And one effective way of getting people to embrace failure as a normal and necessary part of life is to talk about it. So we do just that — creating a safe space to share drinks, food, and failures with fellow fuckuppers.
We’ve been extremely lucky to have hosted a variety of speakers who’ve shared their failure stories at our past events. This month was no different, with 4 amazing speakers who took us on a whirlwind tour of their failures.
Will Richman started the night off with a series of small failures, then dove into one of his larger fuckups thus far. His big lesson? Do your homework. Will learned this the hard way during his time as co-founder and CEO of Bitmaker labs. The wild success of the coding school had all but blinded it’s founders to one small but crucial detail — in order to legally teach courses, they needed to be registered as a private college. This oversight led to a government probe that forced the school to temporarily shut its doors. Luckily, the team was able to get through their fuckup, and the lessons learned ultimately led Will to his current venture at GrowthGenius.
Up next was Luis Serrano, Founder and CFO (Chief Fun Officer) at FUNdamentals of Play (who else wants that sweet job title?). Luis’ story was different from all our past speakers in that a series personal life and career choice fuckups led him to re-evaluate his values and start his current venture. With a six figure income, beautiful fiancée, and new condo downtown, Luis was on top of the world…until it all came crashing down. In a matter of weeks, Luis lost his job (remember Target Canada? Yeah.), was left by his fiancée, and spiralled into a deep depression. Thankfully, he came to the realization that investing in himself and focusing on what he loved was the key to turning his life around. Raw, emotional, and vulnerable — his story certainly struck a chord with our community.
Sheena Brady, the Owner of Tease Tea and a Merchant Success Lead at Shopify was our third speaker of the night. This successful and poised entrepreneur dove deep into a series of fuckups from her past career in hospitality. As a young manager, Sheena focused on putting pansuits over people; while it seemed like she had her shit together on the outside, she struggled with working relationships and always put the business’ needs first. Ultimately, her lack of interpersonal skills got her fired — which turned out to be a blessing in disguise. Sheena left the hospitality industry and followed her heart to Ottawa where she started working at Shopify and slowly grew her tea business on the side. The growth she’s experienced since was best reflected in her new definition of a Girlboss: “Fearlessly going after what sets your soul on fire. Leaving your impression on people in a positive way, and empowering those around you.”
Last, but certainly not least was Darren Leu — a creative powerhouse who recently ran the BIG on Bloor Festival. He’s also the Founder of DCP Studios and a Program Coordinator at How We Live In Cities. When Darren was starting out as an entrepreneur, he made a series of bad judgements that put him in debt, got him kicked out of his storefront, and landed him in small claims court. Darren’s tale was the perfect example of what happens when you put too much trust in others. As a small towner, his business relationships were based on handshakes and not much else. Like Will, he failed to do his homework and overlooked the legal side of things — a mistake that haunted him for years. He was finally able to dig himself out of the hole he was in and never looked back. His takeaway? You can still build authentic personal relationships with people while ensuring that you dot your i’s and cross your t’s.
A Fuckup Night wouldn’t be complete without an amazing host. Jessica Weisz (past speaker from Fuckup Nights Toronto Vol I, COO at SoapBox, and DMZ alum) stole the show with her incredible energy and commentary. And with her call for “no fluffy shit”, she encouraged our audience to dive deeper into the fuckups during our follow-up Q&A sessions.
And that’s another fuckup night! Thank you to our partners and sponsors: DMZ, Shopify, Beau’s All Natural Brewing, Maker Pizza, and Absurd Visuals for partnering with us to #sharethefailure. And be sure to join us on November 16th for our next event at Shopify! And if you’re interested in sharing your stories of failure with us, please email us at toronto@fuckupnights.co.
