Going Big! with Kevin Gentry

Episode: Going Big with Tyler Cowen, the Information Billionaire: The Future Belongs to the Non-Complacent

Date: December 29, 2025
Guest: Tyler Cowen (Economist, Cultural Commentator, Blogger, Professor at George Mason University)

Episode Overview

In this engaging episode, host Kevin Gentry welcomes back renowned economist and cultural polymath Tyler Cowen for a far-reaching conversation on ambition, innovation, risk-taking, and the future. The discussion chronicles Cowen’s unique personal journey from a curious kid in New Jersey to becoming what he dubs an “information billionaire,” and then dives into actionable insights for listeners seeking to “go big” in life and work. Together, they explore themes of curiosity, mentorship, travel, risk, the disruptive power of technology, and the transformative promise and peril of AI. Throughout, Cowen’s signature blend of sharp intellect, restless curiosity, and pragmatic optimism shines through.

Key Topics & Insights

1. Tyler Cowen: Who Is He? (03:47 - 16:00)

• Self-Description & the “Information Billionaire”

  • Cowen playfully shares how he sometimes describes himself:

    “If I want to be kind of sharp, I’ll say, well, I’m an information billionaire seeking to be an information trillionaire. And then people do ask more because that just confuses them. But I think that’s in fact a pretty good answer.” (05:28)

  • He defines his role as someone who’s “very curious and [likes] to gather and organize information about all sorts of topics.”

• Background & Early Influences

  • Grew up in Hudson County, New Jersey, in a working-class Irish American family (08:07)
  • Experiences living abroad (Germany, Mexico, New Zealand)
  • Academic trajectory: George Mason University for undergrad (driven by interest in Austrian economics and desire for autonomy), Harvard for PhD, tenured young at UC Irvine, ultimately returned to George Mason (08:55–17:09)
  • Early passion for chess, sports, music, books, and cultural immersion:

    “There was just always something going on...You grew up surrounded by high human capital and got the best of both worlds.” (12:18)

• Intellectual Curiosity and Synthesis

  • Gentry references how even AI tools (ChatGPT, Claude) describe Cowen as a “restless intellect in perpetual motion…[whose] superpower is synthesis” (06:14)

2. Innovation, Curiosity, and Building a Lasting Platform (17:35 - 30:16)

• Pursuing New Forms — Blogging & Podcasting

  • Cowen on starting Marginal Revolution:

    “I just thought writing on the Internet was very likely to succeed and I would learn more doing it...I way underestimated how big it would become.” (21:27)

  • Stresses importance of consistency and long-term commitment:

    “I’ve blogged literally every single day. I think it’s more than 22 years now, maybe 23 years. I’ve lost track. But just to keep on doing it and stay in the game…people typically do not do that.” (25:07)

  • Podcasts as an ultimate challenge and opportunity to showcase others’ talents, not just his own:

    “The mission of the podcast is to show or teach other people how to appreciate others...bring out the best in everyone. But that does involve difficult, sharp questions.” (28:59)

• Dealing with Success, Conflict, and “Not Going Crazy”

  “I observed...the number of people who start things and then they go crazy in some way is really quite high. And simply having the wherewithal not to go crazy...There’s very high returns to not going crazy.” (25:07)

• Anecdotes about Pushing Comfort Zones

  • Stories of ethnic dining, travel, and learning by “always asking the local person where to go” (27:04)
  • Emphasis on the rewards of being uncomfortable and seeking out the new

3. Insights on Going Big: Gift, Mentorship, and the Value of Outward Thinking (30:16 - 44:23)

a. Finding Your Unique Gift

• The importance of knowing—and doubling down on—what you do best:

  “In my case, my most fundamental ability is the ability to read very fast.…The more of my life I’ve structured around that ability, the better things have gone for me.” (32:29)

• On reading efficiently:

  “The more books you’ve read, the more you can look at a book and understand which parts you need to read closely and which parts you already know. And that means you read the book much more quickly, but you also read it better because you know where to focus.” (34:40)

b. Mentorship, at Any Stage

• Good mentorship is a lifelong need—including for the “old and successful.”

  “You should probably have 30 or 40 mentors as well as your mentees, and a lot of them will be younger people…think of mentoring as a kind of ecosystem where you participate on both ends.” (36:24)

• On learning from people younger than yourself:

  “When I was young, I hung around with all people who were older. And now that I’m older…almost completely hang around with people who are much younger. There was never quite this point in the middle…” (37:57)

c. Being Outward-Focused and Uncomfortable

• The importance of “looking outward and thinking bigger,” rather than simply reinforcing your intellectual tribe (30:16)
• Travel as a fountain of creative energy and learning:

  “There are always new problems to solve. You’re typically a novice most places you go…It’s how you stay young mentally.” (39:06)

d. Tactics for Meaningful Travel

• Avoid resorts; visit second- and third-tier cities; value serendipity; travel with varied groups to maximize exposure (40:36)
• Positive examples of how travel has shaped Gentry’s and Cowen’s perspectives (41:58)

4. Risk Taking, Complacency, and the Real Meaning of “Going Big” (44:23 - 48:16)

• Cowen on why most people are naturally complacent, and that’s okay—but for the “non-complacent,” discomfort and difference fuel ambition:

  “Most people just don’t want not to be complacent...If you think you can or want to be different, I’m happy to try to give tips, but probably most people should be more or less the way they are.” (43:29)

• On risk vs. compulsion:

  “If you feel like you need to sneeze or you have an illness and you need to write the book to get rid of the illness or the urge to sneeze, you should write the book. Otherwise, you shouldn’t...The risk maybe shouldn’t enter the calculation.” (44:23)

• The illusion of “going big” through size rather than innovation:

  “Very small units, sometimes working with AI...can have immense influence just through reach...There’s some key mechanisms right now working against size mattering.” (46:16)

• The necessity—but downsides—of strife and conflict in big achievements:

  “If everyone around you is happy with how things are going, it’s probably terrible. There’s not enough things being shaken up...when you look at Apple, OpenAI, the Beatles, the Chicago Bulls...there’s a lot of strife and conflict, and that’s also a sign of success.” (46:16)

5. Technology, AI, and the Future (48:40 - 55:50)

a. The Fast Pace and Unpredictable Power of AI

• On accelerating AI progress:

  “If you asked the best AI a year ago, ‘how many Rs are in the word strawberry?’ it would have said two rather than three. This year AIs are sometimes winning gold medals in math Olympiads. That’s basically a one-year difference.” (49:25)

• Advice to listeners:

  “Just get it—pay for the best and most expensive version...It’s worth it. And play around with it and use it for your issues...Have some friends who work with it. If you can be in a chat group of people working with it, you’ll pick up things, you’ll learn things.” (50:30)

b. Should We Be Afraid?

• “A lot of things that I’ve enjoyed doing, it can now do better than I can. So I need to change what I do...I treat it as something to learn from and improve myself with...Approach it with bravery, ambition, and I would say, fortitude above all else.” (51:45)

c. Biomedicine & Human Lifespan

• Optimistic forecast:

  “AI and just other advances as well...will, over the next 40 years, cure most things that kill us.” (52:44)

• Example:

  “Your kids are likely to live to, I don’t know, age 98, whatever is the age of death from old age for them, barring accidents...Most of us will die of old age.” (52:54)

d. Future of Freedom & Societal Challenges

• On global risks and freedom:

  “Wars are the great enemy of freedom…The future of freedom is very much up for grabs, but it will be up to us.” (54:19)

• Disruption in education and government:

  “They’ll both be massively disrupted...A lot of parts of our economy will just be very, very different within 10 years because of AI and related technologies, and that includes education.” (55:21)

6. Final Advice: Ambition, Purpose, and Meaning (56:12 - 58:21)

• On optimism and the critical moment in history:

  “We’re at what is called a hingey moment in time where a lot is at stake and a lot of it could go very badly, including in America...Again, the thing to do is get up and approach it all with ambition and courage and fortitude...” (56:12)

• What Cowen would tell his grandchildren (and listeners):

  “Ambition is just very, very important in life...realize that, in fact, you have the liberty and the license to have a lot more ambition than you thought and no one actually will stop you from doing that...We could in this world have a lot more ambition. It’s simply there for the taking, like fruit on a tree.” (57:56)

Notable Quotes & Moments

• On Sticking With It:

  “Just to keep on doing it and stay in the game…people typically do not do that.” (25:07, Cowen)

• On Non-Complacency:

  “If everyone around you is happy with how things are going, it’s probably terrible. There’s not enough things being shaken up.” (46:16, Cowen)

• On AI’s Transformative Pace:

  “That’s basically a one year difference...What will the next year bring or the year after that? I don’t think anyone really can tell you.” (49:25, Cowen)

• On Information Wealth:

  “I’m an information billionaire seeking to be an information Trillionaire.” (05:28, Cowen)

• On Travel & Staying Young:

  “It’s how you stay young mentally...you just start putting the pieces of the world together. Not that you think you understand it. I’d say in a way you end up more mystified, but you’re just mystified at a deeper level of complexity compared to where you started.” (39:06, Cowen)

• On Ambition and Permission:

  “You have the liberty and the license to have a lot more ambition than you thought and no one actually will stop you from doing that is a revelation to people once they grasp it.” (57:56, Cowen)

Important Timestamps & Segments

• Tyler Cowen’s “Information Billionaire” definition: 05:28
• Early academic path and life choices: 08:07–16:00
• Rise of curiosity as a superpower: 06:14, 25:07
• Commitment to blogging & platform-building: 21:27, 25:07
• On the transformational nature of AI today: 49:25–51:45
• Advice on mentors and lifelong learning: 36:24–38:26
• Reflections on ambition and the freedom to “go big”: 57:56

Takeaways for Listeners

• Find your unique gift and structure your life around it.
• Be ambitious. Few people stop you from aiming higher except yourself.
• Never quit learning, experimenting, or exposing yourself to discomfort and difference.
• Seek mentorship throughout your career—especially from people younger than you.
• Curiosity, travel, and synthesis of new experiences are essential for staying mentally vibrant.
• Size and bureaucracy aren’t the only ways to make impact—small, nimble efforts (often leveraging tech and AI) can scale massively.
• Embrace and work alongside rapid technological change; those who stay current will thrive.
• Don’t be afraid to stand out, shake up complacency, and endure some strife—conflict is often a sign of true achievement.
• At this “hingey moment,” optimism, ambition, and courage matter more than ever.

Final Charge

Tyler Cowen:

“We could in this world have a lot more ambition. It’s simply there for the taking, like fruit on a tree.” (57:56)

The future belongs to the non-complacent.