In 'The Obstacle Is the Way', Ryan Holiday presents a framework for turning obstacles into successes. Drawing from the philosophy of Stoicism and the writings of Marcus Aurelius, Holiday outlines three disciplines: perception, action, and will. He illustrates these principles with historical anecdotes from figures such as John D. Rockefeller, Amelia Earhart, Ulysses S. Grant, and Steve Jobs. The book emphasizes the importance of perception in shaping one's response to obstacles, the need for intentional and creative action, and the cultivation of will to persist through challenges. Holiday argues that by adopting these Stoic principles, individuals can transform their obstacles into opportunities for growth and success.
In *Ego Is the Enemy*, Ryan Holiday delves into the concept of ego and its detrimental effects on personal and professional success. The book is divided into three sections: Aspiration, Success, and Failure, each offering valuable lessons and perspectives. Holiday draws on a vast array of stories and examples from literature, philosophy, and history, featuring figures such as George Marshall, Jackie Robinson, Katharine Graham, Bill Belichick, and Eleanor Roosevelt. These individuals achieved great success by conquering their own egos, and their strategies and tactics are presented as models for readers. The book emphasizes the importance of staying grounded, continually learning, and embracing a mindset of growth rather than letting ego hinder development.
Alexander Ludwig is best known for his breakout roles in The Hunger Games and Vikings, but behind the scenes, he’s a multi-hyphenate: a passionate actor, a devoted entrepreneur, and the co-founder of Their Jewelry—a sustainable, recycled gold and silver brand he runs with his wife.
In this episode, Alexander opens up about the brutal realities of Hollywood, the myth of overnight success, and how ego and humility have shaped his 20-year career. We also dive deep into how he's channeling his platform and resources to build a purpose-driven business that could help tackle the e-waste crisis.
This conversation covers everything from surviving the actor’s feast-or-famine cycle to the importance of storytelling, Stoic philosophy, and finding peace in a hyper-competitive world.
Highlights:
- From Child Actor to Leading Man – Alexander reflects on the slow and painful journey from early Disney movies to The Hunger Games and Vikings
- Hollywood as a Casino – Why acting success is like rolling dice and how persistence creates your own luck
- The Myth of "Making It" – Even after Hunger Games, he still had to audition for everything
- Launching Their Jewelry – The real story behind his sustainable jewelry brand with his wife Lauren
- How E-Waste Could Power the Jewelry of the Future – Their’s plan to recycle gold from old phones to create luxury pieces
- Compounding in the Arts – How Alexander thinks about long-term career building like an investor
- Lessons from Stoicism – Why Ego Is the Enemy changed his life and every actor should read it
- Child Stardom and Money – How losing money early gave him the financial discipline he relies on today
- The Power of Entertainment – Why bringing joy to millions is no small feat
Risk, Peace, and Purpose – What tech billionaires, actors, and founders all share
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Guest Bio:
Alexander Ludwig is an award-winning actor and musician best known for his roles in The Hunger Games, Vikings, and The Covenant. He began acting at age nine and has worked in the industry for over two decades. In 2020, he co-founded Their Jewelry, a sustainable jewelry brand using 100% recycled gold and sterling silver, which he runs with his wife, Lauren Ludwig. He’s also an avid country music songwriter, extreme sports enthusiast, and passionate advocate for mission-driven entrepreneurship.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.
We’d like to thank @JuniperSquare for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #assetmanagement
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Sponsor:
Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.
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Stay Connected:
Twitter:
David Weisburd: @dweisburd
Alexander Ludwig: @alexanderludwig
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Alexander Ludwig: https://www.linkedin.com/in/alexander-ludwig1/
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Links
Their Jewelry: https://theirisours.com/pages/about
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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
(0:00) Episode preview
(1:28) The role of luck and timing in an acting career
(3:02) Keys to success and misconceptions in Hollywood
(5:20) Ludwig's journey and persistence to his first big break
(9:30) Career trajectories and the intrinsic love for acting
(12:20) The impact of entertainment and audience connection
(15:04) Maintaining humility and gratitude in the industry
(18:50) Staying in the game through longevity, passion, and dealing with ego
(22:04) The interplay of hard work, smart work, luck, and humility in success
(24:46) Financial prudence, living within means, and the reality of success
(31:00) Long feedback loops, compounding, and contrarian bets in careers
(33:16) Passion as a driver for long-term success and career focus
(39:36) Achieving success through focus vs. diversification
(42:01) Synergies between podcasting and fund management
(43:22) Staying within your circle of competence and balancing interests
(45:38) Evaluating new opportunities and Alexander Ludwig's startup, There
(48:23) Differentiating in a saturated market and sustainability initiatives
(54:29) Billionaires' motivations and the drive for innovation
(1:01:56) Lessons from starting as a child actor and the importance of passion
(1:03:29) Balancing vision with focus and Kobe Bryant's philosophy
(1:05:13) Closing remarks
How I Invest with David Weisburd 
