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In this insightful episode, Ani Filipova speaks with Barry O'Reilly, an entrepreneur, consultant, and author of Unlearn. Barry shares his journey from early-stage startups in San Francisco to global consultancy roles and founding Nobody Studios. Together, they explore career transitions, unlearning outdated mindsets, and actionable strategies for managing risk and pursuing growth. Barry’s philosophy on adaptability, self-reflection, and risk-taking offers a blueprint for thriving in a constantly changing world.

Barry O'Reilly is an entrepreneur, keynote speaker, and author of Unlearn and Lean Enterprise. As co-founder of Nobody Studios, he aims to launch 100 startups in five years. With experience ranging from startups to Fortune 500 advising, Barry helps individuals and organizations unlearn limitations, embrace innovation, and achieve lasting success.

Barry shares how his early experiences in startups and corporate environments shaped his entrepreneurial mindset. He discusses recognizing when it’s time for a career change, managing risk, and the importance of unlearning outdated beliefs for growth.

Expect engaging stories about competing with Elon Musk’s first startup, bold career risks, and actionable advice for breaking career stagnation through small experiments and calculated steps.

Expect to Learn:

The power of unlearning and how it leads to growth.How to recognize when it’s time for a career change.Strategies for managing risk and creating optionality in career decisions.Why action is the only way to overcome stagnation.The role of curiosity and self-reflection in building resilience.

🌟 Episode Highlights with Timestamps

00:02:06 – Barry's Early Career in San Francisco

00:05:35 – Barry’s Job experience

00:15:39 – Recognizing When to Change Careers

00:18:19 – Barry’s Risk-Based Approach to Career Changes

00:25:29 – Risks in career and overcoming the setbacks

00:32:42 – Insights into Barry’s book

00:36:06 – Concept of Unlearning

00:43:46 – Barry’s personal experience about this life as a Leadership Coach

00:45:23 – Conclusion

Follow the Host

LinkedIn: https://www.linkedin.com/in/anifilipova/Personal site: https://anifilipova.me

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Follow the Guest

Website: https://www.barryoreilly.com/

Instagram: https://www.instagram.com/barryoreilly

Twitter: https://x.com/barryoreilly

YouTube: http://www.youtube.com/@BarryOReillyLive

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