In this episode of The Evolve Project, host Alex Knight—a creative producer dedicated to helping ethical entrepreneurs build fulfilling lives and businesses—speaks with David Eastman, a seasoned CEO, startup advisor, and mentor with over 25 years of experience leading agencies and working with entrepreneurial ventures across London, Amsterdam, New York, Silicon Valley, and now Sydney.
Together, they delve into the concept of antifragility—growing stronger under pressure rather than just bouncing back—how to pivot when plans derail, and why embracing creativity can open more doors than you ever imagined. This wide-ranging conversation touches on everything from the parallels between acting auditions and startup pitches to the crucial role of mindset in entrepreneurial success.
GUEST BIO: DAVID EASTMAN
David Eastman is a British-American CEO, tech investor, advisor, and mentor who has led top-tier agencies and startups in Europe and the United States. With a background that spans creative advertising, digital transformation, and marketing for Fortune 100/FTSE 100 brands, David combines a passion for innovation with a deep understanding of organizational leadership. Having worked in cities like London, Amsterdam, New York, and Silicon Valley, he now calls Sydney home, where he continues to guide and invest in founders looking to create meaningful impact.
Former positions include:
CEO, Butler, Shine, Stern & Partners (San Francisco)
Managing Partner, MCD Partners (New York)
CEO, North America & Worldwide Director of Digital, J. Walter Thompson (New York)
CEO, Agency Republic (London)
CEO, agency.com (New York)
Board/Professional Highlights:
Board Director, The 4A’s, Ad Council, ANA Educational Foundation
Fellow at the Royal Society of Arts
Media appearances: Bloomberg, Forbes, BBC, Fast Company, SXSW, Cannes Creativity Festival
EPISODE HIGHLIGHTS & TIMESTAMPS
[00:00:42] – David’s Early Career & Shift from Acting to Business
Growing up in the UK with a dream of being a musician/actor.
A serendipitous meeting at a party led to joining a 1990s internet startup that went public before the tech bubble burst.
David’s 25+ years guiding creative agencies and startups in Europe, the US, and now Australia.
[00:02:32] – Overcoming Early Dream “Failures”
Alex asks about David’s pivot from acting/music to finding a fulfilling career in creative business.
Why “another door” can still lead to creativity and satisfaction, even if the original dream doesn’t pan out.
[00:06:00] – Black Swans, Luck, and Timing
Referencing actors like Brad Pitt or Julia Roberts as examples of how luck and “black swan” events play a massive role in success.
David connects this to entrepreneurial endeavors—sometimes even great ideas require the right moment.
[00:07:57] – Creativity, AI, and the Startup Mindset
Modern opportunities: how the internet and AI expand possibilities for creatives and entrepreneurs.
Viewing your career or project as a “startup of you,” requiring openness to reinvention.
[00:09:03] – Anti-Fragility vs. Resilience
Why “resilience” (just surviving) is different from “antifragility” (thriving under stress).
David recounts examples of founders pivoting after failed client deals—those who adapt quickly often discover bigger opportunities.
[00:14:16] – Mindset, Beliefs, and Growth
Alex explains how beliefs shape our reactions and performance under pressure.
Discussion on shifting beliefs from scarcity to abundance, and how that can unlock potential.
[00:17:50] – Building Entrepreneurial Skills
The importance of recognizing multiple career paths and the value of mindset-oriented learning.
David’s take on whether qualities like adaptability can be taught or are innate—hint: you can improve any skill with focus.
[00:24:00] – Facing Criticism & “Clutch Moments”
How creatives in agencies manage tough feedback.
The difference between those who fold under pressure and those who come back stronger with fresh solutions.
[00:30:00] – Ego, Coaching, and Leading Teams
David’s realization that being a great CEO/coach doesn’t mean you do everything yourself.
Letting go of ego to delegate to those who excel in different areas.
[00:34:00] – Authenticity vs. “Fitting the Box”
Why stepping outside traditional molds matters—especially when AI can handle repetitive tasks.
Alex highlights the fear factor in “being yourself” at work and pushing beyond the familiar.
[00:37:17] – The Abrupt Ending & What’s Next
Alex explains the cut-off in recording time.
Preview of the next deep-dive episode, “Barrels and Ignition,” focusing on practical tools for thriving in business and beyond.
KEY CONCEPTS MENTIONED
Below are concepts raised during the conversation (please add or link to your Evolve Theory articles where relevant):
Antifragility – The idea of gaining strength from stressors rather than just surviving.
Black Swan Events – Highly unpredictable events that have major impact.
Mindset & Beliefs – How core beliefs affect entrepreneurial success.
Abundance vs. Scarcity – Beliefs around opportunities influence how we adapt.
Pivoting / Adapting – Knowing when and how to change direction in business or life.
Barrels and Ammunition (referenced from Keith Raboy) – Differentiating those who can drive an idea end-to-end (“barrels”) from those who support execution (“ammunition”).
If you’re an ethical entrepreneur looking to build a fulfilling business that positively impacts customers, team members, and communities, join The Evolve Project community. Engage with like-minded innovators, gain exclusive insights, and accelerate your growth.
Love the episode? Please share it with friends or colleagues who’d appreciate practical advice on mindset, adaptation, and creative entrepreneurship. Your support helps us reach more people and continue to evolve together.
Enjoyed this episode? Stay tuned for our upcoming deep-dive:
Barrels and Ignition – where we’ll explore the mechanics of leading transformative projects (as the “barrel”) and how to ignite passion in your team.
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