Sipapalooza

On this special edition of Sipapalooza, I have a 3-way conversation with JB of @Gentleman_Ways and the creator behind @TimelessTrvlr to talk about their positive and inspirational accounts on X — why they started, what they’re trying to do, and how they built pages people love to follow.

We talk motivation, staying on brand, the value of posting something constructive, and the practical habits that keep a page from drifting.

We also get into travel: where, when, why, and how they think about it.

If you’re trying to grow on X without turning into another argument account, this is the conversation you want to hear.

If you want to learn about who and what drives these great accounts, and you are seeking usable advice on building an account that lasts then you will enjoy our chat.

Find them at

The Timeless Traveler X: https://x.com/TimelessTrvlr

Substack: https://thetimelesstraveler.substack.com/

The Ways of a Gentleman X: https://x.com/Gentleman_Ways

Substack: https://thewaysofagentleman.substack.com/ Linktree: https://linktr.ee/the_ways_of_a_gentleman

Join me as I sit down once more with J.B. Lloyd - this time to talk through his last two books: The Leisure of a Gentleman and the just-released The Ways of a Young Gentleman, his 16-week curriculum for boys ages 10–18 on character, leadership, etiquette, confidence, and practical life skills.

Hey, it's really interesting! I promise. We also get into how people actually dress in airports, ideas for raising better children instead of just more comfortable ones, and whatever else comes up once the conversation starts wandering.

So pour yourself any beverage of your choice and join us for another episode of Sipapalooza!

Kindly order lotsa stuff at CampfireShoppe.com

Celebrity culture is over. Not “evolving.” Over. Nobody is waiting for the next baby announcement, divorce leak, or red-carpet interview. The old stars still act like strangers owe them attention. They don’t. Their personal lives are content with no audience. The only time they trend is when there is a death, or in the case of nepo babies, their dead parent’s name is attached to the story.

The next famous people won’t be actors, athletes, or nepo kids. They’ll be the people who build AI characters — and the characters themselves. Faces that never age, never get caught, never ask you to care that they had a baby. Creators who understand the assignment: give people a story, not a lifestyle to worship.

This show is about the collapse of the old fame machine and the rise of the one replacing it. Why the public checked out. Why celebrities still haven’t noticed. And why the most magnetic “person” of the next decade may not be a person at all.

Sean Lennon blocked me on X.

Maybe it was his assistant, lawyer, or whoever runs the account. Doesn’t matter. It still happened, and it was petty. Kindly listen to the podcast and let me know what your thoughts are about this? If a musician on social media writes "GO FOR IT" and encourages a filmmaker to create a music video with his music, is that permission to do so? Yes, it was informal, but "go for it" sure sounds like a greenlight to me! Kindly let me know.

Imagine the day coming when you can go on whatever your favorite tech is (computer, cell phone, whatever is coming next) and you could speak to an AI John Lennon and ask him about his life and career? None of what he shares will be invented. It would be based upon all publicly available info out there already.

I use John Lennon as an example because everyone knows who he was, but this conversation is really about the future of AI celebrities. AI Scott Adams already exists. Which celebrity will be next?

Join me at Patreon/StrangeHistory

Kindly check out my sponsor CampfireShoppe.com

How I am Producing the Life at the Dakota AI Dramatic Series. Part 01

I am producing a dramatic series about LIFE AT THE DAKOTA apartment building in NYC, most famous as the home of John Lennon. I plan to produce at least 1 episode a month for the next 60 months. Yes, that's 5 years. I have written 14 prologues in order to introduce the characters and their lives in the 19th century. The prologues are all pre-1880. The 60 episodes I have in development take place between 1880-1900 with the exception of episode one (1) which includes flashbacks.

The technology will improve over time but I am committed to creating recurring characters you will enjoy seeing and hearing. About half the cast are Dakota residents, while the rest are staff, mostly those who worked in the private restaurant and in the basement kitchen.

This is a ton of work and I am doing it all myself. At least for now I am. I will be releasing the prologues first. Kindly join me at Patreon/StrangeHistory to be the first to see everything as it comes together and exclusive content.

Join me at Patreon/StrangeHistory

Kindly check out my sponsor CampfireShoppe.com

How I am Producing the Life at the Dakota AI Dramatic Series. Part 01

I am producing a dramatic series about LIFE AT THE DAKOTA apartment building in NYC, most famous as the home of John Lennon. I plan to produce at least 1 episode a month for the next 60 months. Yes, that's 5 years. I have written 14 prologues in order to introduce the characters and their lives in the 19th century. The prologues are all pre-1880. The 60 episodes I have in development take place between 1880-1900 with the exception of episode one (1) which includes flashbacks.

The technology will improve over time but I am committed to creating recurring characters you will enjoy seeing and hearing. About half the cast are Dakota residents, while the rest are staff, mostly those who worked in the private restaurant and in the basement kitchen.

This is a ton of work and I am doing it all myself. At least for now I am. I will be releasing the prologues first. Kindly join me at Patreon/StrangeHistory to be the first to see everything as it comes together and exclusive content.

Join me at Patreon/StrangeHistory

Kindly check out my sponsor CampfireShoppe.com

Kindly check out my latest episode of Sipapaplooza. I have a conversation with my friend DAN RICHTER. He is a legendary MIME who was hired by Stanley Kubrick to star in and choreograph the Dawn of Man sequence in 2001: A Space Odyssey. He is also a poet and an artist who was great friends with John and Yoko. In fact, he lived at Tittenhurst Park longer than they did and has amazing memories of NYC and London in the 1960s, and living at the Chelsea Hotel in NYC.

Kindly check out my sponsors:

CampfireShoppe.com

VitalogyShoppe.com

And join me on Patreon/Strange History for exclusive content.

Kindly check out my latest episode of Sipapaplooza. I have a conversation with my friend DAN RICHTER. He is a legendary MIME who was hired by Stanley Kubrick to star in and choreograph the Dawn of Man sequence in 2001: A Space Odyssey. He is also a poet and an artist who was great friends with John and Yoko. In fact, he lived at Tittenhurst Park longer than they did and has amazing memories of NYC and London in the 1960s, and living at the Chelsea Hotel in NYC.

Kindly check out my sponsors:

CampfireShoppe.com

VitalogyShoppe.com

And join me on Patreon/Strange History for exclusive content.

Welcome back, fellow time travelers. Grab your matcha latte (or mead, cider, coffee—whatever fuels you) and settle in for another Sipapalooza.

This episode dives into the everyday absurdities and bigger cultural shifts shaping 2026. I start with tipping culture: how a once-optional reward for good service mutated into a mandatory guilt tax forced on customers by apps, tablets, and post-pandemic norms—and why it’s time to end it. Then it’s pure Gen X nostalgia as I revisit 1980s record stores through the lens of a great Rick Beato + Professor of Rock conversation: the bins, the clerks, the physical discovery that algorithms can’t replace.

I unpack the future of neighborhoods and parenting amid cratering birth rates, rising single living, and the growth of intentional co-parenting and mutual-aid models. Next, Johnny Depp’s post-trial Hollywood return becomes a case study in the collapse of the old star system—where franchises and IP now matter more than any single face, and generative AI is waiting in the wings.

I also call out the flood of low-effort AI history “slop” saturating social feeds and why a correction toward real substance is inevitable.

I close by paraphrasing 10 practical, no-nonsense lessons from Scott Adams on systems over goals, talent stacks, energy management, affirmations, and more.

Real talk on culture, tech, nostalgia, and practical living. Share your thoughts in the comments—do you still tip? Miss record stores? Care about celebrities anymore?

Safe travels on all your journeys!

Scott