BrisTech Leaders Event Recap: FailCon 20/20 – Lessons from the Other Side of Success

Caitlin Skinn
June 9, 2025

Last Thursday evening, BLACKROC HQ was buzzing as we hosted one of our most thought-provoking events to date — FailCon 20/20, a candid conversation on leadership, failure, and the hard-won lessons that rarely make it into LinkedIn highlight reels.

The room was packed with Brisbane’s sharpest technology and business minds, all eager to hear from a panel of seasoned leaders who’ve weathered the storms of entrepreneurship and executive life.

Moderated by BLACKROC’s Managing Director, Jason Roulston, the evening brought raw honesty, a few laughs, and a genuine sense of connection as our four incredible speakers shared their stories:

From the outset, the tone was clear: this wasn’t a place for polished narratives or ego. Our panellists peeled back the curtain on the less glamorous side of leadership—where things go wrong, and what you do next.

 

Key Themes from the Night

Failure as Data
Rather than seeing failure as a stopping point, our speakers framed it as a rich source of insight. “Failure is data, not a verdict,” as one panelist put it. Whether it’s a bad partnership, a market misstep, or a cultural disconnect, the lesson is always: adapt faster, not harder.

Leadership is Lonely — But It Doesn’t Have to Be
The panel explored the emotional side of leadership. Trust, transparency, and self-awareness were recurring themes. Leaders need to be comfortable with discomfort and surrounded by people who won’t just tell them what they want to hear.

The People You Keep Around You Matter
Your circle can either elevate you or insulate you from reality. One insight that stuck: “You become the average of the five people you spend the most time with — choose wisely.”

Don’t Be Loyal to Bad Ideas
Sometimes courage means cutting ties—not with people, but with ideas that no longer serve the business. The cost of misplaced loyalty was a particularly powerful takeaway.

More Than a Conversation

The event wasn’t just about learning—it was also about giving back. All proceeds from ticket sales were donated to the FlightCentre Foundation, supporting communities in need across Australia and beyond.

Thank you to our speakers for their vulnerability, our engaged audience for showing up with curiosity and openness, and the BLACKROC team for putting together another standout event for Brisbane’s technology and leadership community.

 

What’s Next?

We’re not slowing down. On Thursday, August 21st,we're back with another unfiltered panel: POWER & POLITICS: The Unspoken Realities of Corporate Leadership

Expect real talk about:

  • Navigating toxic power dynamics
  • Cultural delusion in leadership teams
  • The invisible cost of micromanagement
  • How to lead when the rules aren’t written down

We’ll be announcing the speaker lineup soon—watch this space.

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