The James Altucher Show

A Note from James:
I’ve been in therapy for more than three decades.
Different therapists. Different kinds of therapy. Different crises.
And one question has always fascinated me: What is the therapist actually thinking while I’m sitting there talking?
Are they bored? Are they judging me? Are they secretly Googling me?
My guest today, Lori Gottlieb, knows the answer—because she’s both sides of the story.
She’s a psychotherapist, author of the bestselling book Maybe You Should Talk to Someone, and the writer behind the popular advice column “Ask the Therapist.”
But what makes Lori unique is that she’s willing to pull back the curtain on therapy itself: what therapists think, what patients hide, and why people keep repeating the same patterns in relationships and life.
This episode originally aired several years ago, but the ideas still feel incredibly relevant—especially now, when conversations about mental health are everywhere.
So if you’ve ever wondered what’s really happening on the other side of the therapy couch, this conversation is for you.

Episode Description:
Psychotherapist and bestselling author Lori Gottlieb joins James to discuss what really happens inside therapy—and what both therapists and patients often misunderstand about the process.
Drawing from her book Maybe You Should Talk to Someone, Lori explains why therapy isn’t just about venting problems but about understanding the patterns that drive them.
James shares his own experiences as a long-time therapy patient, raising questions many people quietly wonder: Do therapists judge their patients? Do they get bored? Do they Google the people they treat?
Lori answers candidly, discussing the hidden dynamics of therapy, the emotional complexity therapists carry home with them, and why the most important conversations in therapy are often the ones people hesitate to bring up.
The conversation also explores relationships, secrets, childhood experiences, and why many people keep repeating the same life patterns—even when they know better.

What You’ll Learn:
Why therapy isn’t just about discussing problems—it’s about understanding patterns
The difference between content and process in relationships
Why therapists rarely get bored—even when problems seem trivial
The surprising ways therapists think about their patients
Why the hardest topics in therapy often show up at the end of a session

Timestamped Chapters:
[00:02:00] Lori Gottlieb on Therapy as “Editing Your Life Story”
[00:03:00] Introduction to Lori Gottlieb
[00:04:16] Inside the Book Maybe You Should Talk to Someone
[00:05:02] Why Therapists Need Therapists
[00:06:17] Are Therapists Bored Listening to Problems?
[00:07:00] Content vs Process: The Real Work of Therapy
[00:09:00] Why Pain Has No Hierarchy
[00:10:23] James’s “Statistician” Theory of Therapy
[00:11:00] Why Every Patient’s Story Is Unique
[00:12:00] Finding Something Likable in Every Patient
[00:12:45] The Hollywood Producer Patient
[00:15:12] The Most “Boring” Therapy Patients
[00:16:03] Labeling What’s Happening in a Conversation
[00:18:00] Building Trust Without Oversharing
[00:20:00] Judgment vs Protectiveness in Therapy
[00:23:04] What Therapists Wish Patients Knew
[00:24:11] Do Therapists Care What Patients Think of Them?
[00:25:00] Different Styles of Therapy
[00:29:00] Advice vs Understanding in Therapy
[00:32:51] Do Therapists Ever Google Their Patients?
[00:36:00] Why Patients Googling Therapists Can Backfire
[00:38:00] The Awkward Beginning of Every Therapy Session
[00:41:00] Working With a Patient Facing Terminal Cancer
[00:44:00] The Emotional Impact of Therapy Work
[00:46:00] Handling Suicidal Patients
[00:47:30] When Therapy Ends
[00:50:00] Why Saying Goodbye Matters in Therapy
[00:53:00] “Doorknob Disclosures” — The Secrets Patients Reveal Last

Links and Resources:
Check out Lori’s website and sign up for her newsletter at Lorigottlieb.com
Ask the Therapist is the column Lori writes for the New York Times. You can submit a question for Lori here
Read Lori’s book, “Maybe You Should Talk to Someone: A Therapist, HER Therapist, and Our Lives Revealed.”
Also check out Lori’s book from 2011, “Marry Him: The Case for Settling for Mr. Good Enough” (This book is not about settling! She says “I didn’t win the title battle with the publisher. And I still get letters from people who say the book has helped them.” A lot of it has to do with saving your marriage or setting standards. And she wrote a column about this once, too.)
“Dear Therapist” is the column Lori wrote for six years for “The Atlantic.”
Follow Lori on Twitter and Facebook

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A Note from James:
In the Blondie song “Rapture,” which was the number-one song in 1981, Debbie Harry has this famous line: “Fab Five Freddy told me everybody’s fly.”
So the question is—who is Fab Five Freddy?
This guy is one of the central figures in the birth of hip-hop culture. Not just rap music, but the whole ecosystem: graffiti, breakdancing, fashion, DJ culture, art, film—everything that eventually turned into a massive global industry.
Hip-hop today represents hundreds of billions of dollars in music, fashion, and entertainment. But in the late ’70s and early ’80s it was just a small creative movement happening in New York.
Fab 5 Freddy helped connect all those worlds. He bridged graffiti artists, musicians, downtown art scenes, and eventually MTV.
He also just wrote a book called Everybody’s Fly, and it was a huge honor for me to talk with him about the origins of hip-hop and how creativity actually grows.

Episode Description:
Before hip-hop became a global industry, it was a loose network of DJs, graffiti artists, dancers, and musicians creating something entirely new in New York City.
Fab 5 Freddy was at the center of it.
In this conversation, he explains how hip-hop emerged from a mix of street culture, art scenes, punk music, and experimentation with records and sound. He discusses the origins of graffiti tagging, the rise of DJs like Grandmaster Flash, and the cultural moment when Blondie’s “Rapture” helped bring hip-hop into mainstream awareness.
Freddy also shares how the first hip-hop film, Wild Style, helped unify the culture’s elements—music, dance, graffiti, and fashion—and introduce them to a wider audience.
The conversation then turns to the modern era: AI-generated music, the attention economy of social media, and why artists today may need to slow down and develop their work before exposing it to the world.

What You’ll Learn:
How hip-hop emerged from a mix of music, graffiti, dance, and street culture
Why early DJs searched old records for breakbeats to create new sounds
How the film Wild Style helped define hip-hop culture for the world
Why artists today may need to resist posting unfinished work online
How creativity evolves when technology disrupts the music industry

Timestamped Chapters
[00:02:00] The Story Behind the Title Everybody’s Fly
[00:03:01] A Note from James
[00:04:15] Meeting Biz Markie and the Culture of Collecting Hip-Hop History
[00:05:35] How Jazz, Blues, and Soul Influenced Early Hip-Hop
[00:06:22] DJs Digging Through Records to Find Breakbeats
[00:07:40] Grandmaster Flash and the Science of DJing
[00:08:41] Why Producers Became Central to Hip-Hop Music
[00:09:54] Blondie’s “Rapture” and Hip-Hop’s Mainstream Breakthrough
[00:11:00] The Downtown Art Scene: Basquiat, Keith Haring, and Andy Warhol
[00:12:24] The Origins of Graffiti and Tagging Culture
[00:13:48] Graffiti as Competition and Artistic Evolution
[00:15:12] Punk Rock and Hip-Hop: Parallel Cultural Revolutions
[00:17:47] The Idea for the First Hip-Hop Film Wild Style
[00:19:02] Bringing Breakdancing, Graffiti, and Rap Together on Film
[00:21:50] Lessons Modern Artists Can Learn from Early Hip-Hop
[00:22:49] Why Posting Creative Work Too Early Can Hurt It
[00:24:00] Social Media, Attention, and the Speed of Culture
[00:26:00] Hip-Hop’s Global Influence
[00:29:00] The Birth of Conscious Rap
[00:31:12] Directing KRS-One’s “My Philosophy” Video
[00:33:00] Finding Great Hip-Hop in the Streaming Era
[00:36:00] Battle Rap and Lyrical Skill
[00:37:00] Artists Who Still Push the Genre Forward
[00:40:11] How Rappers Make Money Today
[00:43:00] What Makes an Artist Stand the Test of Time
[00:47:00] Sampling, Technology, and the Evolution of Music Production
[00:54:00] AI Music and the Future of Creativity
[01:02:00] What “Everybody’s Fly” Really Means

Additional Resources:
Fab 5 Freddy
https://en.wikipedia.org/wiki/Fab_Five_Freddy
Rapture
https://en.wikipedia.org/wiki/Rapture_(Blondie_song)
Wild Style
https://en.wikipedia.org/wiki/Wild_Style
Grandmaster Flash
https://en.wikipedia.org/wiki/Grandmaster_Flash
KRS-One
https://en.wikipedia.org/wiki/KRS-One
Debbie Harry
https://en.wikipedia.org/wiki/Debbie_Harry

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A Note from James:
Tony Hawk is one of the greatest athletes of all time—but what fascinates me most isn’t just the tricks.
It’s the mindset.
Tony didn’t just become the best skateboarder in the world. He built an entire ecosystem around what he loved: competitions, companies, tours, sponsorships, and one of the most successful video game franchises ever created.
What’s interesting is that none of it was planned that way. It came from constant experimentation, falling—literally—and getting back up again.
In this episode, Tony talks about the path to excellence, how he handled criticism and failure, the moment he finally landed the legendary 900 trick, and how skateboarding evolved from an underground subculture into a global industry.

Episode Description:
Tony Hawk didn’t just change skateboarding—he helped transform it into a global cultural phenomenon.
In this archival conversation, Tony shares the real story behind his career: learning to master fear, surviving the ups and downs of a niche sport, and eventually building a massive business empire around skateboarding.
He explains how passion drove him through the lean years when skateboarding almost disappeared, why constant experimentation helped him stay at the top, and how a combination of timing, risk-taking, and creative control led to the success of the Tony Hawk’s Pro Skater video game franchise.
The conversation also explores the legendary moment when he landed the first successful 900, the importance of protecting your brand, and why mastery often comes from relentless curiosity rather than natural talent.

What You’ll Learn:
Why pursuing passion—even during downturns—can create long-term success
How failure and repetition build elite skill in any discipline
Why protecting your brand and intellectual control matters in business
How the 900 trick became one of the most iconic moments in sports history
Why continuous learning and experimentation are essential for staying relevant

Timestamped Chapters:
[00:02:00] The Physics of Skateboarding & Learning Through Failure
[00:03:12] Introduction
[00:03:38] Developing Air Awareness in Skateboarding
[00:04:10] The First Time Going Airborne in a Pool
[00:05:05] Learning How to Fall Safely
[00:06:19] Aging, Risk & Walking Away from Mega Ramps
[00:07:17] Skateboarding’s Rebellious Origins
[00:08:00] Creativity and Individual Style in Skate Culture
[00:09:00] Advice for Pursuing Excellence
[00:10:00] Learning Every Aspect of an Industry
[00:11:35] Skateboarding’s Collapse in the Early ’90s
[00:12:33] Becoming a Professional Skater
[00:14:02] Mentorship from Stacy Peralta
[00:15:13] Going Broke During Skateboarding’s Down Years
[00:16:29] Skating Parking Lot Shows for $100 a Day
[00:17:31] The X Games and Skateboarding’s Comeback
[00:18:45] The Video Game That Changed Everything
[00:19:31] When Tony Hawk’s Pro Skater Became “The Game”
[00:20:24] Lessons from Skateboarding Applied to Business
[00:21:17] A Failed High-End Denim Business
[00:22:43] Being Called a Sellout
[00:24:00] Protecting Your Brand and Reputation
[00:25:13] Creating Tony Hawk’s Pro Skater
[00:26:20] Designing the Game Mechanics
[00:27:20] The Long Road to the 900
[00:29:35] Landing the 900 at the X Games
[00:31:08] Becoming Tony Hawk Inc.
[00:32:21] The Importance of Total Immersion
[00:33:29] Designing the Downward Spiral Ramp
[00:35:24] Advice for Raising a Passionate Kid
[00:38:12] Business Advice from Tony Hawk’s Sister
[00:40:29] Working with Family
[00:43:04] Why Some Athletes Fade After Success
[00:44:28] Clearing Up the 900 Controversy
[00:48:00] The Hoverboard Prank

Additional Resources:
Official Tony Hawk
Tony Hawk's™ Pro Skater™ 3 + 4
Bones Brigade: An Autobiography
Riley Hawk on Instagram

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A Note from James:
In the last episode, we talked about whether Martin Shkreli really deserves the label “most hated man in America.” My conclusion was no, and I hope you came to the same conclusion after hearing his perspective.
In this episode, we shift gears completely. We talk about Bitcoin, crypto, AI, energy, optical computing, and what the future of technology might actually look like.
Martin has a very unusual combination of skills—finance, biotech, programming—and I always enjoy hearing how he connects ideas across different fields. That’s what this conversation is about.

Episode Description:
What happens when AI demand collides with the limits of computing power and energy?
In Part 2, Martin Shkreli and James explore the future of technology—from crypto vulnerabilities to optical computing, GPU scaling, and the potential energy crisis driven by artificial intelligence.
They discuss whether Bitcoin can survive quantum computing, why stablecoins solve real-world financial problems, and how computing architecture may shift beyond traditional silicon chips. The conversation then moves into AI economics: why companies might spend billions on compute to make better decisions, how energy constraints could shape innovation, and why optical computing could become the next major breakthrough.
This episode isn’t about controversy—it’s about technological leverage, incentives, and where computation is heading next.

What You’ll Learn:
Why quantum computing could eventually threaten Bitcoin’s encryption
The real-world advantages of stablecoins and decentralized payments
How AI demand could create massive new energy constraints
Why optical (photonic) computing may outperform traditional silicon chips
How businesses might use large-scale AI compute for strategic decisions

Timestamped Chapters:
[00:02:00] Bitcoin, Encryption & Quantum Computing Risks
[00:03:02] A Note from James
[00:03:34] Crypto Markets: Speculation vs. Utility
[00:05:23] Banking Control, Debanking & Stablecoins
[00:07:40] Moore’s Law, Huang’s Law & The Limits of Silicon
[00:08:45] Optical Computing Explained
[00:09:12] NVIDIA, Parallelization & Power Consumption
[00:10:24] Energy Constraints & The Electrical Grid
[00:11:41] AI Energy Demand vs. Countries
[00:12:24] Corporate AI Decision-Making at Scale
[00:13:37] The Coming Explosion of AI Compute
[00:14:20] Energy Efficiency vs. Speed
[00:15:17] GPU Efficiency Improvements & Jevons Paradox
[00:17:00] Why AI Is Different from Traditional Computing
[00:17:47] Optical vs. Quantum vs. DNA Computing
[00:18:19] Why Optical Computing Fits AI Perfectly
[00:19:28] Precision, Bits & Neural Networks
[00:21:24] Error Tolerance in AI Systems
[00:22:00] Fiber Optics & Existing Infrastructure
[00:23:16] New Computing Paradigms Beyond Silicon
[00:24:00] Matrix Multiplication & AI Workloads
[00:24:53] Closing Thoughts

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A Note from James:
Is he the most hated man in America? I don’t think so.
Martin Shkreli was notorious for various reasons that you’ll hear about in this episode—there are some crazy stories—but I’ve come to know Martin over the past few months as both a friend and business partner.
Let’s just hear his stories and explanations. I think you’ll agree with me that this is one of the smartest people I’ve ever had on the podcast.

Episode Description:
Martin Shkreli became one of the most controversial figures in business history—labeled “the most hated man in America,” prosecuted, imprisoned, and publicly vilified.
In this conversation, he tells his side of the story.
Part 1 focuses on how media narratives form, why conviction and risk-taking matter in entrepreneurship, and the deeper mechanics behind the pharmaceutical controversy that made him famous. He explains the economics of drug pricing, insurance systems, neglected medications, and why public perception diverged so dramatically from what patients actually experienced.
The episode also explores learning across disciplines, intellectual courage, prosecutors’ incentives, and how public scandals evolve into legal consequences.
Whether you agree with him or not, the discussion raises uncomfortable questions about business, regulation, media, and reputation.

What You’ll Learn:
Why media narratives can shape public opinion more than facts
The real economics behind pharmaceutical pricing and insurance coverage
How entrepreneurs learn complex industries without formal training
Why conviction and risk tolerance are essential in investing and business
How incentives within legal and political systems influence outcomes

Timestamped Chapters:
[00:02:00] “Most Hated Man in America” — Media Narratives & Reputation
[00:03:11] A Note from James
[00:03:45] Humor vs. Backlash: Handling Public Criticism
[00:06:39] Conviction, Investing & Standing Your Ground
[00:09:00] Optimism, Forgiveness & Business Relationships
[00:12:08] The Pharma Controversy Begins
[00:14:52] From Hedge Funds to Biotech CEO
[00:17:40] Learning New Industries from Scratch
[00:19:00] Staying Curious & Avoiding Fear of Complexity
[00:21:00] Borrowing Knowledge Across Domains
[00:23:06] How People Actually Learn Complex Skills
[00:29:00] Entrepreneurship, Ego & Motivation
[00:31:20] The Daraprim Pricing Decision Explained
[00:34:00] Neglected Drugs & Pharma Economics
[00:37:00] Profit Motive vs. Public Good
[00:41:13] Why He Became the Target
[00:45:00] Prosecutors, Incentives & Legal Strategy
[00:47:00] Hedge Funds, Technical Violations & Trials
[00:50:00] High-Profile Cases & Selective Enforcement
[00:53:00] Media Attention & Personal Decisions

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