The man behind the world's strangest endurance races, plus a great podcast about learning

October 3, 2025

Dear Friends,

This week, I want to start by recommending two books I’ve recently finished. The first is In The Name of Freedom by Enes Kanter Freedom. It’s the story of a remarkable man who has lived a remarkable life. Freedom grew up in Turkey and quickly realized he had an astonishing aptitude for basketball, and the size to succeed in the sport too. He came to the United States for prep school with no idea what this country was like. He walked up and touched a Black man’s skin in a mall, just to know what it felt like; his first Thanksgiving, staying with an American family, he was so nervous that the food wasn’t halal that he quietly stuffed it all in a backpack under his seat at the table. He initially kept his distance from the Jews he met and when a friend—whose religion he hadn’t known—invited him over for Shabbat dinner, he worried that he would be forced to drink blood and eat babies. Still, he went, and was astonished at the generosity and kindness. “It was the best night I had had to that point since I left Turkey,” he wrote.

Eventually, he became a star in the NBA and an outspoken advocate for tolerance, freedom, and democracy. At first, he protested only repression in his home country, which, he writes, led Turkish officials to revoke his passport and try kidnapping him and imprisoning his father. Eventually, his activism moved to confronting dictatorships around the world. This angered NBA officials and Freedom has not played since 2022. He has used that time to write about his life and his devotion to this country and its best ideals. I wish he still could play, for lots of reasons. But at least we have his remarkable book to read. It comes out next week.

The second is another classic American story: The Endurance Artist, a biography of Lazarus Lake, the man who has designed some of the strangest endurance races in the world. He’s creating the “backyard ultra,” in which runners have to complete 4.1 miles every hour until they collapse. He runs the “Barkley Marathons,” in which runners have to travel deep into Frozen Head State Park in the Tennessee mountains and tear pages out of books that Lake has hidden. The race starts when Lake lights a cigarette and often ends without a single person completing the course within the limit of 60 hours. My current favorite race of his is one in which everyone competes to run the farthest distance, but they get an hour for every year of their age. A 48-year-old gets 48 hours. A 60-year-old gets 60 hours. 

Lake may be a sadist, but he isn’t a simple trickster. He’s dealt with medical torture, profound penury, and relentless pain. He’s turned it all into creation and inspiration. He’s also walked across the country three times. I had long known about the races, and I’ve been delighted to learn about the man behind them through Jared Beasley’s wonderful book.

Back to more normal fare, I enjoyed this Aeon essay on whether humans should use genetic engineering to tinker with nature as we wreck havoc—and this 60 Minutes segment on the same theme, asking whether scientists should reengineer mice to reduce the spread of Lyme disease from the ticks the rodents carry. I loved this podcast between Anne Applebaum and Garry Kasparov about the playbook for authoritarianism that they have observed across the world. And this fascinating conversation between Dwarkesh Patel and Richard Sutton about the differences between the way animals, humans, and machines learn.

Speaking of which, I want to note that Anthropic recently reached a preliminary settlement with the authors whose books it allegedly pirated and will be paying out about $3,000 per book in the dataset. All the authors who read this newsletter can check if their books appear here and then file a claim.

The Most Interesting Things In Tech This Week

Anthropic released Claude Sonnet 4.5 this week, and with it the company published a paper detailing various improvements and benchmarks. I was encouraged to see that it’s the company’s most aligned model yet, but I was even more impressed by Anthropic’s claims that it can code for 30 hours straight. That’s a remarkable leap. It also raises real questions as we figure out how to manage these agents and how to point them in the right direction. 

There were some fascinating responses in a SAS and IDC survey of almost 2,400 business and IT professionals about AI, including the fact that executives ranked “cost cutting” dead last when ranking the potential benefits of AI. Meanwhile, it appears Meta might have produced a pair of AR glasses that actually catch on with the public, and it’s due in part to feedback from the visually impaired community. This is a great example of a company developing a product for a niche community and refining it until it's ready for the mass market. 

Finally, I was struck by a thought about the nuances of human learning while running to one of my son’s soccer games. We primarily learn two ways: Through instruction—like, say, my son’s soccer coach instructing him on how to bend the ball on a corner kick—and through personal feedback loops. By practicing corner kicks, my son will learn not just the best place to hit the ball with his foot, but also how to swing his leg, position his body, adjust for weather, and all the other intricacies that come with figuring out something yourself. This is a kind of learning that I don't think AI does, and I wonder if it could provide a way to accelerate growth and intelligence.

Listen

My conversation with the artist Holly Herndon is now up on YouTube. We talked about how she trained an AI model with every sound possibility of her voice, the line between authentic and artificial in art, and why Spotify turning into a slop farm might be best for everyone—including Spotify. 

Question of the Week

I recently did a looped ultra time trial (as many 2.2 mile loops as you can do in 12 hours). I used AI a lot in the first half (I was too wiped to use it in the second) - logging my distance, calories, perceived effort - so I didn’t have to do any cognitive manual effort in tracking nutrition and time goals. I also used it to give me pep talks and find me music and to keep me motivated in general. That personalized conversational in-the-moment guidance made it feel substantially different from a Garmin/smart watch.

I placed 1st overall in this race and while I’m pretty sure I’d have gotten the win even if I didn’t use AI, it begs the question for me what guardrails we need to put in place for AI usage in sports as this becomes more normalized.

Do you have a take on “technology doping for the mind”? If we give an athlete access to a hyper personalized coach during a performance event, does that contribute an unfair advantage?

-Alexia C.

This is a great question! I too use AI to help me with coaching, though more in the preparation for races than during it. 

My general view is that there shouldn’t be any limitations imposed on such cases in normal races—though it seems likely that Lazarus Lake will ban it in his. The reason to ban steroids and certain kinds of shoes is if they either A) confer an unfair advantage or B) could be harmful to the human body. The use of AI doesn’t seem to cross either line in my mind. With some moderate exceptions, everyone has access to the same software, and it seems, in fact, generally like a tool that will keep people safer and healthier. 

That said, I love the data collection of what you’re doing, but I probably won’t be using it for motivation or encouragement. I run in part to develop a deeper understanding of my body, and I fear that this could cut off some of the learning. I don’t listen to music in races or workouts, for example, because I worry that it could desensitize me to some of what is happening in my body neurologically and physiologically. I’d think of this almost like the way I think about cognitive offloading.

In sum, I think it should be entirely legal to go ahead and ask CoachGPT what you should do when you’re on the 30th loop of that race. I just wouldn’t recommend it.

Cheers * N

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