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Barry Diller: Building IAC

Sep 30, 2025 1h 28 insights
My guest this week is Barry Diller, one of America's most successful businessmen. At 83, he chose to publish a deeply personal book and open up about his successes and failures. With surprising candor he details the rules he's lived by: trust first, confront directly, and make the call when the clock starts. In our conversation, he shares why success teaches you nothing, why failure is essential, and why instinct still beats algorithms in a data-obsessed world. This episode is filled with Hollywood lore and business acumen. ----- About Barry: He is the Chairman and Senior Executive of IAC, and is best known for founding the Fox Broadcasting Company with Rupert Murdoch and leading Paramount Pictures. Over his career, he has reshaped television, film, and online media. ----- Approximate Timestamps:
Actionable Insights

1. Prioritize Continuous Curiosity

Define personal success as maintaining continuous curiosity, allowing it to be the primary driver in your life and work.

2. Act Immediately on Ethical Incidents

The moment you become aware of an ethical breach or incident, recognize that ’the clock is ticking’ and you become absolutely responsible for every subsequent action taken.

3. Fight Against Cynicism

Actively combat cynicism and prevent past experiences from corrupting your basic instincts, striving to maintain a degree of naivete to make better decisions.

4. Embrace Confrontational Idea Exchange

Actively seek out and embrace environments where passionate people engage in confrontational arguing of ideas, as listening closely in such settings can reveal deeper truths and better insights.

5. Embrace Failure for Learning

Recognize that success teaches nothing, but failure provides significant lessons, so view failures as opportunities for profound learning.

6. Cultivate Insatiable Learning

Actively seek opportunities for insatiable learning, as this intense pursuit of knowledge can ignite a strong sense of ambition and purposefulness.

7. Follow Broad Interests, Not Goals

Instead of setting rigid career goals, identify your broad interests and find any entry point to get on that general path, trusting that subsequent steps will naturally unfold.

8. Embrace Unmastered Roles

When given a position you don’t have experience for, simply commit to doing the work, as the effort and dedication will naturally impress others and lead to further opportunities.

9. Believe Despite No Evidence

Embrace the ‘fake it until you make it’ mindset by believing in your capabilities and acting accordingly, even when tangible evidence is lacking, as this can be crucial for success.

10. Take Unwanted Jobs for Learning

Seek out and accept jobs that others don’t want if they provide unique opportunities for deep learning and skill acquisition, allowing you to gain valuable knowledge.

11. Build Strong, Differentiated Brands

For businesses, especially in media, focus on building strong, clearly differentiated brands and creating content that resonates directly with people to ensure enduring value and engagement.

12. Invest in Non-Disintermediated Assets

Seek out and invest in assets or businesses that cannot be easily disintermediated by technology, as these possess unique and enduring value.

13. Act on Clear Opportunities

When a compelling opportunity presents itself, especially when an asset’s value is temporarily decreased but its long-term viability is clear, act decisively.

14. Compensate for Created Value

Compensate employees on a cash basis for the value they create within a given period, ensuring they directly share in the enterprise’s success annually.

15. Offer Opportunity, Not Retention

To retain talent, focus on providing genuine opportunities and fostering an enjoyable work environment, rather than relying on retention schemes like stock vesting.

16. Share Growth, Enable Ownership

Reward employees with a share of the growth they provide to the business, and if they desire ownership, empower them to use their cash compensation to buy stock.

17. Align Risk with Reward

Structure compensation and incentives to align risk with reward, ensuring that those who take valuable risks and succeed are appropriately compensated.

18. Embrace ‘Stupid’ Ideas

Do not fear presenting or considering ‘dumb, stupid, or wrong’ ideas, as they are often necessary steps that lead to better, smarter ideas.

19. Confront Discomfort Directly

When faced with an uncomfortable situation, acknowledge your commitment and directly engage with it to overcome initial apprehension and eventually become accustomed to the exposure.

20. Cultivate Discipline for Projects

For long-term projects, cultivate discipline to consistently return to the work, even if it means setting it aside and revisiting it over extended periods, rather than waiting for dedication.

21. Be Direct and Sincere

Communicate directly, sincerely, and sometimes bluntly, as this straightforward approach can help build trust with people.

22. Start with Trust

Approach interactions and relationships by defaulting to trust, requiring significant actions from others to break it, rather than starting from a place of distrust.

23. Let Go of Vengeance

When trust is inevitably broken in business, avoid holding onto vengeance or remembering past betrayals, as this can contribute to personal well-being.

24. Use Insecurity to Propel Action

If you lack a sense of self or confidence, leverage the drive to please others in the early stages of your career to gain momentum, and then sustain that forward movement.

25. Embrace Self-Reliance

Recognize that you are ultimately responsible for your own protection and well-being, which can foster a necessary sense of independence.

26. Tell Your True Story

If you believe your life has a good story and you can tell it truthfully, commit to the effort of documenting it, even if it takes a long time.

27. Strive for Excellence

Dedicate yourself to being exceptionally good at your current role, no matter how junior, as this commitment can spur you on and impress others.

28. Avoid Pro Forma Networking

Avoid engaging in ‘pro forma’ networking or rigidly structured career steps, as career progression is often more naturalistic and driven by genuine engagement and performance.