Are your business strategies making you stronger with every shock, or just setting you up for the next collapse? For decades, the goal has been resilience—to absorb a hit and return to baseline. But in today's world of black swan events and non-stop disruption, merely surviving isn't enough. We need to be antifragile: systems and organizations that literally improve because of volatility, disorder, and stress. Forget precise forecasting; the smartest move is designing a structure where the potential gains from randomness always outweigh the losses.

In this deep-dive episode, Jane and Austin break down Nassim Nicholas Taleb's revolutionary triad—Fragile, Robust, Antifragile—and show you how to apply it to your organization. Learn the strategies of embracing small, low-cost failures, why redundancy is more valuable than pure efficiency, and how to create a culture of decentralized decision-making where every team has skin in the game. Stop fighting uncertainty and start leveraging it. Tune in to discover how to turn the chaos of the market into your greatest competitive advantage.

Highlights:

• Key Concepts and Implications
• Strategies to Build Antifragility
• Risks and Mitigations
• Metrics and Signals to Monitor
• Immediate Stress-Test Ideas

Ready to escape the annual planning treadmill? Join Jane and Austin as they dissect why traditional corporate planning feels instantly obsolete and reveal the game-changing strategies that successful executives at companies like Linktree, Vanta, and Notion are using to revolutionize the process. From the golden rule of aggressive timeboxing and constraining debate with data, to crafting a compelling strategic narrative and defining clear "kill criteria" for failing projects, this episode is packed with the insights you need to make your company's planning more efficient, adaptable, and a true driver of execution.

Highlights:

• The Problem with Traditional Annual Planning

• Evolution Toward Efficiency: The 10% Rule
• Constraining Debate and Tailoring Processes
• Strategy as Narrative with Focused Bets
• Financial Grounding and Organizational Design
• Resource Planning and Success Metrics
• Continuous Evolution and Agility
• Kill Criteria and Final Thoughts

Ever wondered what separates a long-lasting, impactful leader from one who crashes and burns? The statistics are brutal: 50% of initially successful leaders eventually fail in some way.

Failure isn't just about getting fired; it's about the inability to achieve results through people.

In this powerful episode, Jane and Austin pull back the curtain on leadership derailment. They dismantle the biggest threats to your success—from the invisible mindset traps that cloud your judgment—like the illusion of certainty—to the toxic ways leadership failure bleeds over into your team.

But here's the good news: leadership failure is preventable.

If you’re ready to avoid being just another statistic, you need to hear this and take the first step toward becoming a stronger leader.

Highlights:

• Leadership Failure: The Surprising Prevalence
• The Structure: Mindset, Team Impact, and Prevention
• Internal Mindset Traps: Cognitive Biases
• Team Impact: Where Teams Feel the Heat
• Prevention Blueprint: Building Psychological Safety
• Practical Habits: Daily Practices for Resilience
• The Prevention Blueprint: Four Core Commitments