On the eve of my Vermont Mastermind Experience last week…
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The AI company Anthropic agreed to pay a record $1.5 billion settlement to resolve a copyright lawsuit over the illegal downloading of over 500,000 books to train its Claude.ai chatbot.
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This is a BIG DEAL.
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And here’s why:
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First, this is the largest payout ever in the history of U.S. copyright cases (which is massive in and of itself…)
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But second, this is the first ever class-action settlement in the US involving AI and copyright (which is HUGE.)
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Because with more than 40 other active copyright lawsuits vs. AI companies currently underway (now with more likely coming…)
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This may represent a turning point in the “dog and cat” battle between content creators and AI companies.
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Now, the question of course is….
1 | How Should We Be Thinking About This... "Twist?"
One of the “special” twisty carrots featured in one of our very real farm-to-table lunches at the Vermont Farm Mastermind Experience, with nearly 100% of the food served grown directly on our farm.
Well, as it was described in a private group I’m part of:
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This may be a signal that we’re exiting the “Napster” era and entering into the “Spotify” era of AI…
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And if that’s the case…
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While it’s likely that future payouts may be measured in nickels and dimes…
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With the $1.5 billion lawsuit, Anthropic will pay roughly $3,000 per work to over 500,000 authors around the world.
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Now, in the course of human history…
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Building empires on the backs of unpaid labor is nothing new.
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And in this latest variation…
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If book authors were the first victims of the Great AI Content Heist…
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It looks like video creators may be next…
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In fact…
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According to a breakthrough investigation by The Atlantic…
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At least 15 million YouTube videos (and counting) have been scraped without permission by AI companies to train their data sets, explicitly violating the platform’s terms of service.
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BTW – You can see if any of your YouTube videos have been included in these data sets by searching the data sets here:
Does this mean we should run away from YouTube??
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(I actually think it means the exact opposite…)
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Because as arguably the last remaining “non-AI” powered search engine online…
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I think YouTube may be the next big AI battleground…
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(Read: Watch this space…)
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In fact, speaking of YouTube…
2 | My Upcoming "Town Hall" & An Unexpected YouTube Breakthrough...
After receiving an overwhelming expression of interest…
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I’ve decided that I *am* going host the Town Hall I mentioned in last week’s newsletter.
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(Thank you to everyone who took the time to write in!)
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BUT…
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With all my commitments on my plate this fall – coaching soccer, farm harvest, finishing my forthcoming book, serving my private advisory clients, not to mention traveling / speaking / events etc. – I’ve had to thread the needle with my schedule.
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The GOOD NEWS is that I’ve been able to find a time and date that I can make work for this Town Hall Event.
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So I invite you to SAVE THE DATE:
Save the date:
Live Town Hall Event w/ Ryan Levesque
Thursday, October 2nd @ 11am CT (90 Mins)
I’ll be following up in the coming weeks with a Zoom Registration Link & Details.
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But in the meantime…
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Quick Note: Similar to past Town Hall Events, the Live Zoom Meeting will be capped at 300 attendees – and will very likely fill up beyond capacity. So if you’re interested in joining me, be sure to keep your eyes peeled for registration details.
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Now, one of the things I’ll be talking about in this Town Hall…
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Is what we’ve learned in the last 6 months building (from scratch) the Strategic Content Ecosystem I wrote about most recently in July 2025 in [Issue #055] My Contrarian YouTube Strategy
For example, barely 18 weeks into executing the YouTube portion of this strategy – we’ve already had our first long-form video pop.
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Over 27K+ views and counting.
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(See below…)
Now, I thought it would take us at least a year to see a video pop like this.
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Because, to be clear:
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This is not some shallow “attention chasing” video…
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Or an attempt to try to “game the algorithm”…
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Instead, this 14-minute video is filled with original thought leadership…
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And it is very much intended to “cultivate influence” (as I wrote about back in [Issue #031]: Cultivating Influence vs. Chasing Attention.)
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But more importantly…
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This video is an example of the Return to Real principles in action.
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AND…
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It’s an example of what can happen when you take a Single Source of Truth piece of content (i.e. like a weekly newsletter that you personally write, Ã la The Digital Contrarian) and strategically repurpose it for discovery – in a dozen places across the internet – including long-form video on YouTube.
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So, why did this video POP?
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I’ll walk you through exactly what we’re doing, as well as why I think this video popped… along with some of the biggest lessons we’ve learned in this process…
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All on the upcoming Town Hall…
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Which takes us to…
3 | 27 Other Takeaways from My Vermont Mastermind...
Originally in this issue of The Digital Contrarian…
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I was planning on summarizing some of my biggest takeaways from our recent Vermont Farm Mastermind Experience…
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But one of the founders in attendance – Maeve Ferguson (pictured in the foreground above) – wrote an excellent piece this week sharing some of her biggest takeaways…
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Things like:
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- What are the non-obvious questions to be asking when stuck…
- How to re-think about the *actual* moat protecting your business…
- Why studying anthropology is so important in the age of AI…
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And so much more…
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And I thought it would be cool for you to be able to read about the experience through the eyes of someone other than myself – who was in the room.
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(I’ll share some of my own biggest insights in a future issue…)
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So…
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Without further delay:
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I’m wrapping today’s issue by sharing a link to the article Maeve published this weekend, which I highly recommend checking out:
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I’m curious, which of these 27 is YOUR biggest takeaway??
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Okay, I’ll leave you with that for now.
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Have a great rest of your week…
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Remember to hug the ones you love…
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And until next week,
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Ryan :-)
