Tired of polished success stories and carefully curated highlight reels, Amanda Ovaici and Shahr Smed created something different.
In 2019, they launched Fuckup Nights YYC, a platform dedicated to the stories most people never share: the failed launches, costly mistakes, sleepless nights, broken partnerships, and hard lessons that shape every entrepreneurial journey.
As professionals themselves, Amanda, a lawyer and entrepreneur, and Shahr, a venture capitalist with Plug and Play, knew success is rarely as simple as it appears. Behind every celebrated win are moments of uncertainty, failure, and resilience.
Inspired by the global Fuckup Nights movement, they brought the concept to Calgary to create a space where founders, creators, executives, and community leaders could share the stories that don’t make it onto LinkedIn.
These aren’t cautionary tales. They’re stories of perseverance, growth, and the lessons learned when things don’t go according to plan.
Today, Fuckup Nights YYC has grown into a thriving community where vulnerability is celebrated, authenticity is valued, and failure is viewed not as shame, but as fuel.
The stage isn’t about perfection. It’s about honesty.
What to Expect at a Fuckup Nights Event
- Four speakers sharing one defining setback and what it taught them
- 7 to 10 minute stories filled with insight, humour, and hard earned lessons
- Connection, conversation, and networking with Calgary’s entrepreneurial community Real Stories.
- Real Lessons.
NEXT EVENT- SEPTEMBER 17, 2026
TICKETS ON SHOWPASS
SPEAKER SPOTLIGHT
BRYDON GIERL
Founder of CoolIT Systems
About Brydon
Brydon Gierl is the Co-Founder of CoolIT Systems and has spent more than 20 years helping shape the future of liquid cooling technology. From startup uncertainty to global growth, he helped build CoolIT from a bold idea into a company that sold in 2026 for US$4.75 billion, proving that some of the biggest success stories begin with the biggest risks.
Before CoolIT, Brydon worked across construction and fabrication industries, where he developed the hands-on mindset that continues to define his approach to business and innovation.
In 2026, CoolIT became one of Calgary’s most celebrated tech success stories with its acquisition by Ecolab. Behind the headline, however, is a story of risk, resilience, hard lessons, and the realities of building something from the ground up.
FAILURE IS A CERTAIN PATH TO THE TRUTH, TO IGNORE ITS GIFT IS A MISSED OPPORTUNITY
What Brydon says about FAILURE
Failure is inevitable for each new enterprise, how the people experiencing it perceive and react to it is what makes the difference.
As a musician, playing live it is the most thrilling and precarious thing you can do, as you walk a thin line between control, improvisation, and inspiration. I think we used those same principles in this business endeavour, probably unconsciously.
In the beginning we relied on intuition, iteration, and determination to make forward progress. We expected failure but understood an improvement was lurking on the other side, not perfection.
SPEAKER SPOTLIGHT
ALLISON GRAFTON
President & Founder of Rockwood Custom Homes
About Allison
Allison Grafton is the Founder and President of Rockwood Custom Homes. In 2009, she left a successful career in investment banking and bet on herself, building a company that would become one of Western Canada’s leading luxury home builders.
Known for her fearless leadership, uncompromising standards, and entrepreneurial grit, Allison has built more than award-winning homes. She has built a reputation for challenging convention, raising industry standards, and creating a company that clients and competitors alike respect.
In an industry where few women have led at this level, Allison’s journey stands as a powerful reminder that extraordinary results rarely come from playing it safe.
EVERY SETBACK IS AN OPPORTUNITY TO LEARN, EVOLVE, AND BUILD RESILIENCE
What Allison says about FAILURE
Growth only happens when you’re willing to step beyond your comfort zone. Taking risks can sometimes lead to failure, but avoiding risks means avoiding growth altogether.
We can’t fear failure. Every setback is an opportunity to learn, evolve, and build resilience.
Success is built by facing challenges head-on and moving through them with courage and relentless self-belief.
