Jessica Lessin is the founder and CEO of The Information, a media company that’s a trusted source for tech readers and tech leaders. She’s reported on the industry for almost two decades and is deeply familiar with the culture shifts in Silicon Valley. Lessin sits down with Oz to discuss these trends, including tech titans appealing to the new Trump administration.

Jessica Lessin is the founder and CEO of The Information, a media company that&rsquo;s a trusted source for tech readers and tech leaders. She&rsquo;s reported on the industry for almost two decades and is deeply familiar with the culture shifts in Silicon Valley. Lessin sits down with Oz to discuss these trends, including tech titans appealing to the new Trump administration.

Behind every innovation is a new kind of power. TechStuff unpacks how technology reshapes influence, creativity, and control, from Silicon Valley’s rising moguls to the cultural forces they create. Because tech is the new religion, economy, and entertainment, all at once.

Each week, Oz Woloshyn and the brightest minds covering tech dig into the weird, funny, and sometimes unsettling ways technology, AI, and the internet shape our daily lives. From AI and social media to privacy, digital burnout, and the creator economy, they ask how all this innovation is changing who we are, how we work, love, and make meaning.

Smart talk, strange stories, and the questions everyone’s Googling: whether AI will replace us, how social media is affecting our kids, and what it all says about us.

Get in touch here: techstuffpodcast@gmail.com

Behind every innovation is a new kind of power. TechStuff unpacks how technology reshapes influence, creativity, and control, from Silicon Valley&rsquo;s rising moguls to the cultural forces they create. Because tech is the new religion, economy, and entertainment, all at once.
Each week, Oz Woloshyn and the brightest minds covering tech dig into the weird, funny, and sometimes unsettling ways technology, AI, and the internet shape our daily lives. From AI and social media to privacy, digital burnout, and the creator economy, they ask how all this innovation is changing who we are, how we work, love, and make meaning.
Smart talk, strange stories, and the questions everyone&rsquo;s Googling: whether AI will replace us, how social media is affecting our kids, and what it all says about us.
Get in touch here:&nbsp;<a href="mailto:techstuffpodcast@gmail.com" data-stringify-link="mailto:techstuffpodcast@gmail.com" data-sk="tooltip_parent" aria-haspopup="menu">techstuffpodcast@gmail.com</a>

TechStuff

Behind every innovation is a new kind of power. TechStuff unpacks how technology reshapes influence, creativity, and control, from Silicon Valley’s rising moguls to the cultural forces they create. Because tech is the new religion, economy, and entertainment, all at once.

Each week, Oz Woloshyn and the brightest minds covering tech dig into the weird, funny, and sometimes unsettling ways technology, AI, and the internet shape our daily lives. From AI and social media to privacy, digital burnout, and the creator economy, they ask how all this innovation is changing who we are, how we work, love, and make meaning.

Smart talk, strange stories, and the questions everyone’s Googling: whether AI will replace us, how social media is affecting our kids, and what it all says about us.

Behind every innovation is a new kind of power. TechStuff unpacks how technology reshapes influence, creativity, and control, from Silicon Valley&rsquo;s rising moguls to the cultural forces they create. Because tech is the new religion, economy, and entertainment, all at once.
Each week, Oz Woloshyn and the brightest minds covering tech dig into the weird, funny, and sometimes unsettling ways technology, AI, and the internet shape our daily lives. From AI and social media to privacy, digital burnout, and the creator economy, they ask how all this innovation is changing who we are, how we work, love, and make meaning.
Smart talk, strange stories, and the questions everyone&rsquo;s Googling: whether AI will replace us, how social media is affecting our kids, and what it all says about us.

The Story: Vibe Shift in the Valley w/ Jessica Lessin

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/3516cd40-ebe6-4564-8583-b26d009170c4/transcript

Did your college have a secret society? Well, Stanford has a secret off-campus class training the next generation of Silicon Valley billionaires. And it's literally called "How to Rule the World."

Theo Baker arrived at Stanford as an aspiring coder with dreams of building the future. Instead, he stumbled into the "Stanford-within-Stanford" — a hidden pipeline connecting a select few students directly to Silicon Valley CEOs, yacht parties, and venture capitalists offering millions before you even have an idea. Then he decided to write a book about it.

In How to Rule the World: An Education in Power at Stanford University, Theo traces his freshman year transformation from tech idealist to award-winning investigative journalist — including the reporting that brought down Stanford's own president. He joins us to talk power, secrecy, and what Silicon Valley is really teaching the next generation.

Additional Reading: 
How to Rule the World by Theo Baker 


EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/techstuff Try it risk-free now with a 30-day money-back guarantee 

Did your college have a secret society? Well, Stanford has a secret off-campus class training the next generation of Silicon Valley billionaires. And it's literally called "How to Rule the World."
Theo Baker arrived at Stanford as an aspiring coder with dreams of building the future. Instead, he stumbled into the "Stanford-within-Stanford" &mdash; a hidden pipeline connecting a select few students directly to Silicon Valley CEOs, yacht parties, and venture capitalists offering millions before you even have an idea. Then he decided to write a book about it.
In How to Rule the World: An Education in Power at Stanford University, Theo traces his freshman year transformation from tech idealist to award-winning investigative journalist &mdash; including the reporting that brought down Stanford's own president. He joins us to talk power, secrecy, and what Silicon Valley is really teaching the next generation.
Additional Reading:&nbsp;
<ul>
<li aria-level="1"><a href="https://www.penguinrandomhouse.com/books/760317/how-to-rule-the-world-by-theo-baker/">How to Rule the World by Theo Baker</a>&nbsp;</li>
</ul>
 EXCLUSIVE&nbsp;NordVPN Deal ➼<a href="https://nordvpn.com/podcast/?coupon=techstuff&amp;utm_medium=affiliate&amp;utm_term=&amp;utm_content&amp;utm_source=aff141920&amp;utm_campaign=off1001"> https://nordvpn.com/techstuff</a> Try it risk-free now with a 30-day money-back guarantee&nbsp;

The Secret Stanford Off-Campus Class for Tech’s Next Titans - The Story

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/2d6d4852-55f5-4ceb-af2a-b464018b28ca/transcript

Evan turns his AI-powered voice agent loose on the people who are always at the forefront of technological adoption: the fraudsters and the rip-off artists. How will the scammers and spammers react when they face Evan’s voice agent in a battle of wits? And what happens when they deploy the same kind of AI voice agents on Evan that he’s using on them? Shell Game is made by humans. More specifically, it's produced and edited by Sophie Bridges, and written and hosted by Evan Ratliff. Samantha Henig is our executive producer. Visit shellgame.co to find out more and support the show. 

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.shellgame.co/subscribe

See omnystudio.com/listener for privacy information.

Evan turns his AI-powered voice agent loose on the people who are always at the forefront of technological adoption: the fraudsters and the rip-off artists. How will the scammers and spammers react when they face Evan&rsquo;s voice agent in a battle of wits? And what happens when they deploy the same kind of AI voice agents on Evan that he&rsquo;s using on them? Shell Game is made by humans. More specifically, it's produced and edited by Sophie Bridges, and written and hosted by Evan Ratliff. Samantha Henig is our executive producer. Visit shellgame.co to find out more and support the show.&nbsp; This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.shellgame.co/subscribe
See omnystudio.com/listener for privacy information.

Shell Game: Me and My Scammer

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/13cbcc27-898f-4677-8170-b463016c9169/transcript

Blue Origin's latest rocket test ended in what the company called "an anomaly" — and what everyone else would call an explosion. Reed Albergotti (Semafor) explains why blowing things up is just part of the process and why the US Space Program is probably going to be fine. 

Then, Kyle Chayka (The New Yorker) pulls back the curtain on the shadow market for pre-IPO equity in OpenAI, Anthropic, and SpaceX. It’s a mania where people are willing to take pre-IPO stock as payment for $2.9M houses. It's frothy out there. 

Finally, Taylor Lorenz (User Mag) digs into the concept of a ‘permanent underclass’ — the fear that letting AI run rampant could freeze everyone in their current economic position forever. Do we laugh it off or get serious about regulation?

Additional Reading: 
Blue Origin and Amazon Had Momentum. Then Came the Fireball. | The New York Times 
A Booming Shadow Market of Sketchy A.I. Investments | The New Yorker 
You Are About to Become Economically Worthless | User Mag 
Silicon Valley Is Bracing for a Permanent Underclass | The New York Times 

Download SAILY in your app store and use our code techstuff  at checkout to get an exclusive 15% off your first purchase! For further details go tohttps://saily.com/techstuff

Blue Origin's latest rocket test ended in what the company called "an anomaly" &mdash; and what everyone else would call an explosion. Reed Albergotti (Semafor) explains why blowing things up is just part of the process and why the US Space Program is probably going to be fine. Then, Kyle Chayka (The New Yorker) pulls back the curtain on the shadow market for pre-IPO equity in OpenAI, Anthropic, and SpaceX. It&rsquo;s a mania where people are willing to take pre-IPO stock as payment for $2.9M houses. It's frothy out there. Finally, Taylor Lorenz (User Mag) digs into the concept of a &lsquo;permanent underclass&rsquo; &mdash; the fear that letting AI run rampant could freeze everyone in their current economic position forever. Do we laugh it off or get serious about regulation?
Additional Reading:&nbsp;
<ul>
<li aria-level="1"><a href="https://www.nytimes.com/2026/05/29/technology/blue-origin-amazon-rocket-explosion.html">Blue Origin and Amazon Had Momentum. Then Came the Fireball. | The New York Times</a>&nbsp;</li>
<li aria-level="1"><a href="https://www.newyorker.com/culture/infinite-scroll/a-booming-shadow-market-of-sketchy-ai-investments?_sp=18ce7eb0-57da-4ed4-a275-630ea2c86cd1.1780422009345">A Booming Shadow Market of Sketchy A.I. Investments | The New Yorker</a>&nbsp;</li>
<li aria-level="1"><a href="https://youtu.be/_Neog2mAdBI?si=CvtZbp7ezfUr_2qE">You Are About to Become Economically Worthless | User Mag</a>&nbsp;</li>
<li aria-level="1"><a href="https://www.nytimes.com/2026/04/30/opinion/ai-labor-work-force-silicon-valley.html">Silicon Valley Is Bracing for a Permanent Underclass | The New York Times</a>&nbsp;</li>
</ul>
Download&nbsp;SAILY in your app store and use our code techstuff&nbsp; at checkout to get an exclusive 15% off your first purchase! For further details go to<a href="https://saily.com/creator/?coupon=techstuff&amp;utm_source=12669&amp;utm_medium=affiliate&amp;utm_campaign=138&amp;aff_transaction_id=102e6208403cf45b12b357c4a30eb2&amp;aff_offer_id=138&amp;aff_id=12669"> </a><a href="https://saily.com/techstuff">https://saily.com/techstuff</a>

Blue Origin Rocket Explodes in Apocalyptic Mushroom Cloud - Week in Tech

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/c0728934-d318-4d5f-a386-b46000184fd9/transcript

The Story: Vibe Shift in the Valley w/ Jessica Lessin

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