(BNS) Baratunde Thurston

Summary

Tech Brew Ride Home – Baratunde Thurston Interview (October 24, 2025)

Episode Overview

In this episode, Baratunde Thurston—author, comedian, digital provocateur, and media executive—joins host Brian to explore the intersection of technology and comedy across his remarkable career. The conversation charts Thurston’s journey from a techy upbringing in Washington, D.C., through elite education and stand-up immersion in Boston, to the epicenters of digital media and innovation in New York. Along the way, the discussion delves into the cultural shifts that shaped both the web and comedy, the unique spirit of New York’s tech scene, hackathon hilarity, digital expansion at The Onion and The Daily Show, and a critical yet hopeful take on the AI era.

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Key Discussion Points and Insights

1. Tech Roots & Early Comic Influences

[00:30 – 06:14]

• Tech Upbringing: Thurston was "literally born into technology." His mother, a systems analyst and COBOL programmer for the U.S. Treasury, exposed him to computers early on, creating a home environment where technology was both opportunity and adventure.
• Cultural Stew: The breadth of comic influences ranged from Garrison Keillor to Whoopi Goldberg’s solo shows, Bill Cosby’s classic routines (before Cosby’s legacy was reevaluated), Eddie Murphy, and a heavy dose of both American and British sitcoms via PBS. “PBS is just a very slow reclamation of the US by the British through television programming.” (Baratunde, [05:00])

2. Formative Education & Finding a Voice Online

[05:54 – 09:54]

• Sidwell Friends School: Transitioned from majority Black D.C. public schools to an elite Quaker private school—“I’d never seen so many white people in one place before”—which fostered a “healthy form of entitlement” (“kids there are taught that they deserve good things”) and provided top-tier academic opportunities (Baratunde, [06:14]).
• Digital Pioneering: Early T1 internet access at Sidwell led him to MMORPGs, IRC, Usenet, and joke-forward newsletters—“I started an email newsletter… [e-mail]… [curating] jokes that I was finding online, which no one had seen before, because no one had been online before except for me, relatively speaking.” (Baratunde, [08:25])

3. Melding Technology, Satire, and Stand-Up

[09:54 – 16:17]

• Boston Genesis: After Harvard, Thurston stayed in Boston, blending strategy consulting (telecom post-1996 deregulation) with nightly stand-up and lunch-hour political blogging (“by day… a telecom business strategy consultant. By night… a flailing, slightly, steadily improving stand-up comedian. And during my lunch hours, I was like a political commentator on blogging.”, [10:32]).
• Comedy Class & Early Stage Peers: Graduated from a stand-up comedy class at the Boston Center for Adult Education, performing on the same night as Sarah Silverman and rubbing shoulders with future stars like Aziz Ansari and Hannibal Buress ([13:07]).

4. The Onion, Digital Satire, and Media Innovation

[15:16 – 21:41]

• Role at The Onion: Moved to NYC in 2007, joining The Onion as Politics Editor and later Director of Digital, crucially bridging comedy and tech: “They saw how much of a technology background I had… I helped bring them into a technological future… ultimately evolved to Director of Digital.” ([15:17])
• Riding the Web 2.0 Wave: Helped define The Onion’s voice on new platforms—Twitter, apps, and more—“What is the Onion on social media? What is the Onion’s Twitter account? I got to define that with our team.” ([21:41])

5. Digital Community and Comedy Hack Day

[25:07 – 33:28]

• Community Building: “Whiskey Friday” happy hours at The Onion became an incubator for the intersection of techies and comedians from outfits like Huffington Post, BuzzFeed, Reddit, and Foursquare ([26:48]).
• Cultivated Wit & Comedy Hack Day: Co-founded Cultivated Wit, blending coders and comedians in “hackathon” events to create satirical apps—memorable examples included apps auto-blocking calendar events to avoid helping friends move, and splitting bills according to pay-gap data (“Reparations, one meal at a time. That was called Equitable.”, [32:10]).
• Common Ground: Developers and comedians share obsessive, creative “solowness,” late-night jamming, and a drive to manifest ideas—“Both of these types of people are creators… you’re taking an idea and putting it out into the world.” ([30:49])

6. Transforming The Daily Show for the Social Era

[33:28 – 37:59]

• Digital Expansion: Joined The Daily Show as Trevor Noah took the helm, helping transition to an internet-first model—“I was there at the very beginning of that and helping The Daily Show catch up to internet speed.” ([34:02])
• Opening the Creative Pipeline: Built the “expansion team” to fragment, remix, and augment TV content for social and interactive platforms (“on the infinite canvas of the Internet you could experiment more”), bringing hackathon-style collaborative comedy into the show's workflow.
• Notable Moment: Ran projects like the Trump Presidential Tweet Library and participatory brackets on “things Americans hate,” showing how web interactivity could enrich TV satire ([34:02 – 37:59]).

7. The Unique Spirit of New York’s Tech Scene

[39:27 – 42:50]

• NYC’s Recipe: Cross-pollination between media, tech, art, and activism sets NYC apart—“It’s real… New York isn’t a company town… less B.S.… even people of decent means have roommates. So you can't be in so much of a bubble.” ([39:53])
• Contrast with Silicon Valley: NYC tech is more “grounded, human-centric, less about severing oneself from society”— “...if you actually like people and think the world is better on net with them, then you build different types of technology.” ([41:32])

8. Perspective on AI: Power, Politics, Opportunity

[42:50 – 46:41]

• Cautious Optimism: Thurston remains “genetically predisposed” to optimism about AI, but with “a huge asterisk”—“I do not think our system default settings are toward the future I’d prefer… But we still have this window to adjust course.” ([43:16])
• AI and Society: Calls for a political, not just technical, approach—“It’s a form of power, and we all deserve a say in what we do with it. It’s affecting our kids, our food chain, our water supply.” (Referencing a conversation with Gilles Babinet, [45:20])
• Call to Action: “Let’s march, let’s build, let’s create, let’s invest differently… I truly haven’t seen a huge market demand for AI slot feeds… It’s worth questioning that and building something different…” ([46:24])

9. Current Projects and Reflections

[46:41 – End]

• “Life With Machines”: Thurston’s newest project, a show and digital presence dedicated to “creating a world where technology is something we can live well with and not just brace for and endure.” ([46:56])
• Community Shout-Outs: Recognizes other figures worth chronicling in New York’s tech-comedy intersection: Kenyatta Cheese, Anil Dash, and Hilary Mason ([48:46]).
• On Connection: “I’ll see you in these feeds, but also hopefully in these streets and maybe on some trails. Let’s all go touch some grass together. Remember our connection to something bigger than a data center.” ([47:30])

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Notable Quotes and Memorable Moments

• On Comedy Influences:
  “PBS is just a very slow reclamation of the US by the British through television programming.”
  — Baratunde Thurston [05:00]

• On Sidwell Friends:
  “Sidwell was also my introduction to a healthy form of entitlement where kids there are taught that they deserve good things… and that they have value.”
  — Baratunde Thurston [06:14]

• On the Origins of His Tech-Comedy Fusion:
  “I was able to experiment with that same approach not just in the politics, but in the media… I could wait in line like everybody else for a spot at the Comedy Cellar on bringer night… And I did all those things and I could publish my own stuff and I could start making sketches with friends and then I can use this Internet thing because that feels like it’s culture too, to start satirizing and commenting on tech culture with tech.”
  — Baratunde Thurston [23:35]

• On What Makes New York’s Tech Scene Different:
  “New York isn’t a company town in the way that D.C. is a government town… It tends… to be a little more grounded, a little more human-centric, less BS in New York, if I might say so.”
  — Baratunde Thurston [39:53]

• On AI and Society:
  “A lot of what we're experiencing with tech is endurance... we're being subjected to the worldview of a few people who don't like people. Right. And don't like life... So I remain optimistic because I think I'm genetically predisposed, but it's with a huge asterisk.”
  — Baratunde Thurston [43:16]

• Advice on AI Politics:
  “I met this digital leader in France recently, Gilles Babinet … he’s like, I want people to treat [AI] as politics, meaning it’s a form of power and we all deserve a say in what we do with it.”
  — Baratunde Thurston [45:20]

• On Current Mission:
  “Let’s all go touch some grass together. Remember our connection to something bigger than a data center.”
  — Baratunde Thurston [47:30]

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Timestamps for Important Segments

• Early Tech & Comedy Influences: [00:30 – 05:54]
• Sidwell Friends & Early Online Life: [05:54 – 09:54]
• Post-College Life: Consulting, Comedy, Blogging: [09:54 – 15:16]
• Joining The Onion & Redefining Digital Satire: [15:16 – 21:41]
• Onion Happy Hours & Community Building: [25:07 – 27:09]
• Comedy Hack Day & Blending Code with Jokes: [27:09 – 33:28]
• Revamping The Daily Show for Social/Web Era: [33:28 – 37:59]
• What Makes NYC’s Tech Ecosystem Special: [39:27 – 42:50]
• Optimism, Politics, and AI’s Social Impact: [42:50 – 46:41]
• Current Projects & New York Tech Legacy: [46:41 – End]

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Conclusion

This rich, candid episode offers a masterclass in blending technology, media, and comedy—with Baratunde Thurston serving as both a storyteller and a case study in the creative possibilities of the digital age. He urges us to view technology—and particularly AI—as a societal project imbued with politics, to be navigated consciously and creatively. All the while, New York emerges as the beating heart of media-technology cross-pollination: “There are certain things that can only happen in New York City and I think that intersection, even with international politics, creative arts, technology and media is something beautiful worth commemorating and extending.” ([48:52])

Transcript

[WhatsApp Narrator]

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[Baratunde Thurston]

That for the Daily Show. I came in with Trevor right as he took over from Jon Stewart and I was the only new executive on his team. So if you can imagine a president coming into an administration but all their cabinet is the previous administration's leadership, that was the case for Trevor, except for me. And it was over time. He staffed and people adjusted to his voice. But I was there the very beginning of that and helping the Daily show catch up to Internet speed. They really hadn't prioritized that in many ways they didn't need to. With the first Jon Stewart era, they could ride off of the strength of tradition and his strong center of gravity and his knownness, you know what I'm saying? Whereas Trevor was not known at all in the US and. And so he was like really open to the network, was really open to. Let's experiment.

[Interviewer Brian]

R. Tunde, Thurston, thanks for coming on to talk to me once again.

[Baratunde Thurston]

Brian, it's good to be back with you and hello everyone.

[Interviewer Brian]

Including robot, including the AI that's scraping this right now. When we spoke a previous time, we got into like your tech background. You grew up in D.C. i think you told me the story of how you got into computers, but do that again. Your mother was a computer programmer, right?

[Baratunde Thurston]

Yeah, I was literally born into technology, Brian. My mother was a programmer. Systems analyst was her formal title for the Department of the Treasury, Office of the Comptroller of the Currency, something in the late 70s, early 80s. She got her official certification. In fact, I was going through her files. She passed 20 years ago. And I found the letter, the formal letter saying like, congratulations, you're a computer programmer. And that's how it happened. They sent you a letter, put it on a piece of paper and told you you were certified. So she was in charge of. She worked on a team that was like overseeing national banks. She coded in cobol. And I remember going to work with her. I remember her bringing a computer home. The first computer box I remember was candy. And yeah, PCs started making their way into our house. And that really launched my exploration of this other way to connect and create and find opportunity and start fights and just be a human with the technology of the time.

[Interviewer Brian]

I recommend anyone searching first ones with Baratunde Thurston for more details about the. His. His tech background. But okay, what I have not, not asked you before about is comedy. And I want to, I want to almost ask the Marc Maron question, like, who are your guys? Who are your people that inspired comedy for you?

[Baratunde Thurston]

When I was a kid, that same mother, you know, she was into tech, she was also into politics and made sure I had a grounding in a truer history of the US we grew up in Washington D.C. taxation without representation for the win. And she was into nature, which meant we went camping and hiking and took a lot of road trips. And on those road trips, we would listen to audio cassettes of comedy. Well, we would listen to Garrison Keillor and his old radio programs, Lake Wobegon, which has a particular Midwestern sensibility. Nothing like what I grew up in, in dc. But then we would listen also to Whoopi Goldberg and not Whoopi from the View, not Whoopi from Sister Act, Whoopi from Long stand up and comedic. One woman shows. One woman shows big monologues and she's characters that she would do. We would listen to Bill Cosby pre. Everything we would later learn about Bill.

[Interviewer Brian]

Cosby, but classic bits like the Noah bit and stuff like that.

[Baratunde Thurston]

Yeah, I want you to build an.

[Interviewer Brian]

R. What is a cubit?

[Baratunde Thurston]

Yes. So listening to that, watching Eddie Murphy, younger than I ever should have, and then watching a lot of sitcoms, watching all in the Family, a lot of Norman Lear productions. You know, Norman Lear was kind of a surrogate dad through his TV programming. And the way this like World War II veteran Jewish American spoke to the black experience, Good times, everything else like that was a big part of my cultural upbringing. And then lastly, you know, British sitcoms. We didn't have cable when I was a kid, so the cosplay of a cable subscriber meant like UHF channels, channels above number 13 on the analog dial. And that's where PBS lived. And PBS is just a very slow reclamation of the US by the British through television programming. So I watched One Foot in the Grave and Fawlty Towers and Are you being served and Chef and all of that. Created this spicy stew of wit, fit and comedy and satire to try to make sense of the world.

[Interviewer Brian]

You went to Sidwell Friends?

[Baratunde Thurston]

I did.

[Interviewer Brian]

I'm curious. Lots of famous children of politicians and presidents went there. It's a Quaker institution. What influence did Sidwell friends have on you?

[Baratunde Thurston]

Massive influence. So prior to Sidwell, I was in public schools in D.C. bancroft elementary, in the greatest American neighborhood ever, Mount Pleasant. So starting in seventh grade, I switched to Sidwell. And I've never seen so many white people in one place before. Brian. That was just new coming from my neighborhood, which was 90 something percent black and brown. There was one white family that I knew, sorry, two white families that I knew of in our neighborhood in the more immediate sort of five block radius. So Sidwell was a big cultural shift. There was money, you know, it was the first time I had been exposed to upper income people and people with wealth and kids with cars before they could even drive them. So the types of homes I could see. Sidwell was also my introduction to a healthy form of entitlement where kids there are taught that they deserve good things, that education is something they're due, that opportunity is something that they're worthy of and that they have value. And their constant reinforcement is, you matter. And that starts to sink in. So after six years there, I got a great education, I got a good book education, I became a better writer. I got access to amazing science labs and college level professors, including math. When I went to Harvard for college, I realized that the math textbook I had been using in high school was written by a Harvard math department professor. And we got to beta test it at Sidwell. So that was the level of the formal education. But culturally I got to try out a lot. I did this student newspaper. I got to flex my political activism and fight for justice against what felt like a lot of nonsense and bs. And I got on the Internet even more. One of the parents at Sidwell at the time, this is roughly 1993, worked for an Internet backbone company, BBN, Bolt, Baronek and Newman, and they donated a T1 always on connection, which felt blazing compared to like 9,600 Baht. Dialing, right.

[Interviewer Brian]

Modems that we had.

[Baratunde Thurston]

Yeah, yeah. So this was no dialing, no crashing, none of that sound, and the same upload as download. And so in our computer lab at Sidwell, we had a dedicated like Internet UNIX terminal. And that opened up massive worlds for me technologically. I was on massive multiplayer online games. I was in IRC chats, I was hanging out on Usenet Gopher at the time. But also I was finding a comedic repository and way of being funny online. And that was a part of me establishing my own comedy voice. So prior to Sidwell, I was not funny. Right. I enjoyed humor. I was a very serious Child. And I fought for justice and truth in the American way. But because of the Internet, I started finding really absurd jokes. I started an email newsletter, a mailing list, a listserv, as we called it at the time, and I got my friends to subscribe to it. The name of that listserv was jokerscidwell.edu. you just signed up for my curated set of jokes that I was finding online, which no one had seen before, because no one had been online before except for me, relatively speaking. So that curation of other comedy voices would then lead me to develop my own through a satirical newsletter that I started the year after I graduated from Citi.

[Interviewer Brian]

It is interesting, aside from Encarta, I think the second CD ROM I ever got was one of the Monty Python ones or one of the. Eric Idle was always throwing stuff out like that. And one of the first websites that I visited regularly was a guy would summarize that day's Howard Stern show every day. I don't know if it's still there, but anyway, I'm saying that leading to your career is sort of like meshing together tech and comedy. So coming out of college, is that when you come to New York to pursue comedy, coming out of college, what do you do?

[Baratunde Thurston]

So I graduated college in 1999 just to kind of certify myself. Everybody's freaked out about Y2K. Yep, yep, they did the thing, and there was nothing to see here. And the nukes didn't launch because of stale COBOL code, thankfully. So I stayed in Boston after I graduated college. In 99, I took one of these vaguely defined, highly compensating jobs known as strategy consulting, which means I used Excel and PowerPoint to tell vague stories about business possibility and growth and sometimes did some really quality analysis. But that job was important because it was. The firm I worked for was really small, and they were focused on the deregulated telecom industry after the Telecom act in 96, the Ma Bell Monopolies, Regional monopolies of phone companies get broken up. Cable companies can do phones, phones companies can do cable. There's satellite telephony, there's mobile phone service starting to kick off, and there's a lot of money flying around of people looking for opportunity and to compete. So I was positioned at that revolution of technology infrastructure. It was a little less sexy than, like, gaming, and application layer was like, the protocol layer quite often, but it gave me a real deep appreciation for what's required for all of our online experiences to happen. So I did that job until about 2007. And for eight years, by day, I was a telecom business strategy consultant. By night, I was a flailing, slightly, steadily improving stand up comedian. And during my lunch hours, I was like a political commentator on blogging.

[Indeed Sponsor]

Well, in.

[Interviewer Brian]

But you're in Boston through 2010. Boston, okay. Which is.

[Baratunde Thurston]

I live in Boston.

[Interviewer Brian]

Well known as a great, you know, starting ground for comedians.

[Baratunde Thurston]

Absolutely.

[Interviewer Brian]

To use a Pete Holmes term, like, who are your classmates in the sense that of folks that maybe went on to do other things that you were doing bringer sets with and stuff like that.

[Baratunde Thurston]

Absolutely. My very first show when I graduated from my standup comedy class at the Boston center for Adult Education. This is. I go to Sidwell Friends, get the Harvard degree, and then get the most important certification of my professional life, the standup comedy certificate.

[Interviewer Brian]

Did they give you a piece of paper?

[Baratunde Thurston]

I'm pretty sure they did. I'm also pretty sure I don't have it. I was gonna say, but I have the memories. And Steve Kalishman was our teacher and we did a show at the Comedy Studio, really famous legacy comedy institution. Bobcat Goldthwait comes out of there. Eugene Mirman, like a ton of people. My first show, I follow Sarah Silverman. That's like, welcome to Stand up comedy, kid. And in my class of people, you've got folks like Aziz Ansari and Hannibal Burris and Mike Kaplan, and so many folks, some of whom have continued, some of whom have shifted into tech or just parenthood or some other flavor of their lives. But Boston was a great foundation. And then I basically have a realization that the day job, I really can't do that anymore. My role here is not to increase shareholder value for investors and telecom operators. And so I moved to New York City in the fall of 2007 on the strength of an audition I had done for Comedy Central, where one of the executives there said, have you moved to New York yet? And I put a lot of weight in that yet. And so I heard it as like, comedy Central wants me to move to New York City. And I did, and I got a job at the Onion. And that would completely change, again, the trajectory of my life. It's fall of 2007. They had opened up a position for someone to coordinate election coverage leading into the 2008 election. And the job was politics editor. And I'd had a ton of political commentary history. I'd self published a book. I've been doing all this standup and doing a lot of legit activist political blogging. Like, I was a huge participant in.

[Interviewer Brian]

The blogosphere is Jack and Jill Politics before that. Yeah.

[Baratunde Thurston]

Okay, Jack and Jill Politics is running parallel to that entire Boston Histories. So standup comedy at night, strategy consulting in the day, blogging in the lunch hours in between.

[Interviewer Brian]

And when did you sleep?

[Baratunde Thurston]

I slept on the plane, I think, and sometimes at work. But they weren't monitoring employee keystrokes as much as they do now so I could get away with it. Yeah, so New York City called and the Onion became this next nexus point where I ended up redefining the job, and they saw how much of a technology background I had, and they realized they were looking for something they didn't know, which is who could be creative and comedic and have enough credibility with the writers room but also help bring them into a technological future because they were still in the mode of uploading all their content to the web at midnight on Wednesday morning, and that wasn't going to fly anymore. So I ended up being hired for two Politics Editor and then Web Editor was the title. Ultimately it evolved to Director of Digital A bit more Lofty into my Life.

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[Interviewer Brian]

Does that mean. Because this is a thread we're going to run through a little bit here, like nascent social stuff, you know, Facebook has opened up at this point, Twitter is going on.

[Baratunde Thurston]

So part of, you know, I had, I think what's a. There's a lot to anyone's life, of course, so we don't have. We can't do it in real time. But a big part of how I grabbed a little foothold in the comedy world was through technology. That all the jobs I'd had basically since high school involved some kind of tech. In Harvard, I worked tech support at the help desk and climbed the ranks to like advanced support. So I'm helping the techs who need help themselves. And on call overnight, I have a pager. You know, it's like first responder for tech crimes and accidents and things like that. So that was important. I had the satirical newsletter that I ran all through college and I started blogging right after college. And as I'm doing standup in Boston, I'm experimenting with podcasting. I have a low power FM radio show that I record in Allston across the river, and I take those audio files which I was recording on MiniDisc, put them in MP3, load them up in an RSS feed on my own website, and realize that I'm able to kind of understand and track that audience through my site much better than the over the air audience where I'm just like begging, if anyone can hear me now, please call the station or email me later. So, and then recording my own shows and putting those out online and self publishing little zines. This was all part of being entrepreneurial with tech around my comedy voice. So New York steps that up a big chunk and this role at the Onion allows me to do that on behalf of not just myself, but on behalf of America's finest news source.

[Interviewer Brian]

I want to point out that, to put it in context, what you're describing is you've built a career as what we would call an influencer, or.

[Equinix Sponsor]

You'Re.

[Interviewer Brian]

Multimedia you're creating a following of people that know you through various things. And you weren't the first to do this necessarily, but the Casey Neistats of the world, whomever where it's like I know that name because I know him through this, through seeing this online, through the Onion, through eventually the Daily show or whatever. And like what I'm, what I'm saying is, what I'm trying to get at is that is like a well trodden almost sort of template for a career now, but in the 2007, 2008 era, like you're just doing this off of instinct. What is the instinct that tells you that you can make a career this way?

[Baratunde Thurston]

A little bit of that Sidwell entitlement that says like, I deserve to give myself a shot. There's a lot of encouragement from my mother, you know, with enough self confidence and seeing what technology did for her and for our family in terms of opening opportunity creatively and economically. But I would also say what gave me the most encouragement is some version of impact. So when I'm doing this political blogging through the Boston years and into the New York years, I'm finding a community of like minded people through Jack and Jill politics of me and my partner in that Cheryl Conti are testing out with a really nascent movement, a digital activism. How do we tell the story of police brutality that the mainstream media isn't telling? There was a case of the Gina 6, which is like a prototypical Black Lives Matter story. How do we pool resources and advocate bypassing elected officials and go direct to the people? How do we do more community forums and two way communication rather than just top down? So we were feeling accountable to our peers in a way that is not the gatekept method. And then I was able to experiment with that same approach not just in the politics, but in the media. Okay, so I want to do a show. I want to create a voice. Well, I could wait in line like everybody else for a spot at the Comedy Cellar on bringer night or New York standup club or New York, New York or what have you. And I did all those things and I could publish my own stuff and I could start making sketches with friends and then I can use this Internet thing because that feels like it's culture too, to start satirizing and commenting on tech culture with tech. And that was the ultimate merger. So the Onion brought it together because satire is really strengthened by this idea of verisimilitude. The more you can look like the thing you're mocking the higher the satire. So the Onion worked because it looked like a print newspaper, and then it worked again because it sounded like a podcast, and it worked again because it looked like broadcast television. All these different modes. So I show up and it's Internet culture time. So what is the Onion on social media? What is the Onion's Twitter account? I got to define that with our team. What is the Onion's app for iPhone and iPad? What is the conversation that the Onion as old media has with its subscriber base and its listenership and its readership? And the irony of all that, Brian, is we had to do the same things that traditional media did. So I started finding myself in community with the New York Times and their digital lead and with folks who are doing blogging. So this new media thing and Web 2.0, which would become so many other sort of buzzwords, the confidence came from recognizing that there's a deeper pattern that's not really about the technology. It's about who we are as people and how we try to make sense of our reality and our wrestling with what we do with power and how we mock those who haven't and abuse it.

[Interviewer Brian]

I have to alight over some stuff, like the fact that your coverage of the 2008 Democratic National Convention is in the Library of Congress and your book, how to be Black, a memoir and a satire. But let me come back to the combining the technology, the comedians, you start doing comedy hack day events, bringing coders and comedians together. I never had the privilege of attending one. What did. What was that? What was that like?

[Baratunde Thurston]

That was like the best of everything. So the Onion, we started doing these meetups, happy hours. Whiskey Friday was born there, and I took it and ran in an absurd direction. Every Friday we would pop open a bottle of something. Then we started inviting our comedy friends.

[Interviewer Brian]

Where would you do that again?

[Baratunde Thurston]

So the onions. So let me situate you. This is starting in 2007, 2008, SoHo, New York City, about two blocks south of Houston street on Broadway between Prince and Spring. At that point, soho has not yet fully converted into a high end shopping district. Shopping mall has some of that. There are underfed models roaming afoot, desperate for a bite of protein. But there's also still some of that art scene. There's still a little bit of working class business. It's in that peak transition. And on our block, it's not just us, it's Huffington Post one block up. And they're incubating BuzzFeed at this time. It is a comedy site called FiveThirty Six.

[Interviewer Brian]

I remember that.

[Baratunde Thurston]

Or 23Six. Something like that.

[Interviewer Brian]

Yeah, yeah.

[Baratunde Thurston]

How to huff and impose. He'd stumble upon. Their offices are right around the corner. Reddit is nearby. And you've got Foursquare is nearby right over by nyu. Right. There's this whole, like lower Manhattan creative scene.

[Interviewer Brian]

The Gawker. Gawker phones were all there.

[Baratunde Thurston]

Yeah, yeah. So all of that is bubbling and Whiskey Friday, the Onion. I don't want to overplay our influence, but there was something unique about us creating a recurring social space for the comedy community. So, like SNL writers would come by and improvisers and stand up comics, but also because of the tech bridge that I was a part of with what we were doing online. Huffington Post people would come by and stumbleupon people would come by and Foursquare people would come by. And that was a fun world to explore. How do we be creative with these tools? I would leave the Onion in 2012, and more accurately, the Onion would leave New York in 2012. And a lot of us weren't trying to move to Chicago. I had actually attempted to purchase The Onion in 2012 with the support of Betaworks. I was doing a lot of hanging out in the New York tech meetup scene and spending many, many hours over at Beta Works and emceeing Beta Day and doing all kind of fun stuff. There's. And it's still a big part of my life and sense of community comes out of that meatpack industry side. So after leaving the Onion, a lot of us go different ways, but three of us start a company called Cultivated Wit. This was me, Brian Janosch, and Craig Cannon. So three Onion alumni set out to explore this merging of technology and comedy. We don't know exactly what we're up to, but we knew we had a lot of fun. Bending tech to the will of comedy and making jokes with code, not just putting jokes on the Internet. So Craig had the initial spark. Craig was big into the hacker community and the hackathon community. And he said, what if we did a hackathon with comedians and developers? And so we did. We did a test run. We. I think we did it at Twilio's offices, which were just south of Union Square. We got sponsored very much air quotes by MongoDB. And I still have some of the photos and the footage. I'm submitting it to this zine to Remember New York Tech. And it was three communities, designers, developers and comics come together to pitch comedic and satirical experiences built with tech. And so it was a three day event. Friday is pitch and then like the top pitches, people form teams around them. Friday night you jam for 24 hours. Saturday night people put on an internal showcase and then the finalists from that do a show for the public on Sunday with judges from the venture capital and business world and the comedy world. And so we did this in New York multiple times, but we toured it. We did San Francisco Sketchfest, we did Los Angeles at YouTube space in LA. We franchised it like TedX and people did them in Toronto and Washington D.C. and it was one of the best things I've ever been a part of because there was a lot of good social commentary in it. But it was also working technology that could say something using the tools that we were saying something about. We did one at the MIT Media Lab even, which was a real.

[Interviewer Brian]

Is there an overlap between the. You can't even say anymore because developers are so everything now. There's not a cliche of developers, but is there some sort of a common sort of, I don't know, aura or philosophy between devs and comedians?

[Baratunde Thurston]

There can be. There's different types of comedians and obviously different types of developers. But there is a dedication and like solowness to a lot of those communities where I will just jam on something and try to figure something, try to crack this, crack this joke, crack this piece of code or this function that I'm trying to get to work. Late nights for sure is one of them. Sometimes drinking and that's obviously shifting in the culture. Very fewer people are drinking in general, but that has been a thing. And then I think there's an imagination. I think both folks are. And I don't mean this in the woo woo sense, I mean in a literal sense they're manifesting something like you're taking an idea and you're putting it out into the world and you're articulating a way you think the world should be through words, in the case of most comedians, through code, which is just. It's formalized words, right? It's more structured, but it's still writing and articulating thought and putting it as close as you can into matter. And so the idea of taking something from your mind and putting it in the world, like both of these types of people are creators and I think putting them together led to some really ridiculous and hilarious creations. I mean, there was one app which was. What was it called? It was. Oh God. We did it as part of a New York tech meetup. And I can still see the presentation. It was essentially when someone, a friend is asking you for, oh, can you help me move or do this favor for me? As soon as your phone hears the request, it puts something in your calendar to block the time. And you can just be like, oh, I'm sorry, kind of busy right then. Or if you're trying to split the bill with your friends and you're out to eat. This app was split the bill based on the pay gap between different genders and ethnic groups to kind of close that. So it's reparations one meal at a time. That was called equitable. And so not only was the. And that was in the App Store so the apps would work, but then the finalists, we also made these product videos in the spirit of like an Apple product video, or Lyft was having these kitschy, cute videos. So you can still see some of them. They were pretty high production, satirical creations. Yeah, we could use more of that in this moment now. Tech has only gotten more absurd since then.

[Interviewer Brian]

Your time at the Daily show, you're leading digital at the Daily Show. Sort of like your job at the Onion. Are you part of the period where it's like, you know, now media is more people will consume Saturday Night Live or even a soccer game from the clips and the analysis after the fact than we'll actually watch the show? Are you at the nascent era of that where it's like way more people will see the clips from the YouTube than will actually have tuned in the night before?

[Baratunde Thurston]

I'm at the beginning of that for the Daily Show. I came in with Trevor right as he took over from Jon Stewart, and I was the only new executive on his team. So if you can imagine a president coming into an administration, but all their cabinet is the previous administration's leadership. That was the case for Trevor, except for me. And it was over time. He staffed and people adjusted to his voice. But I was there at the very beginning of that and helping the Daily show catch up to Internet speed. They really hadn't prioritized that in many ways. They didn't need to. With the first Jon Stewart era, they could ride off of the strength of tradition and his strong center of gravity and his knownness, you know what I'm saying? Whereas Trevor was not known at all in the US and so he was, like, really open to the network, was really open to let's experiment. And so I was only there for nine months, but it was enough to help give birth to how that show would continue to operate in the Internet era. So I built a team there. We Called it the expansion team. Like, digital expansion was our mission, and our goal was to expand the show. It meant we had one job, which was pretty uninspiring, Right? It was the chop shop. Let's take the show. We make and chop it up and fragment it out so we can meet people where they are on social. All right, cool. Then there was a part of the job which was, let's get more out of what we're already making and try to extend that life. But the most fun part of the job for me was like, let's do stuff that we couldn't do before because of the technology. And that started to happen and has continued. They built a Twitter library that was just after I left. The Trump Presidential tweet library was one really fun example when I was still there. They ran for years after a version of March Madness, where we built our own bracket system to correspond with the NCAA March Madness. But it was participatory, and it was about things Americans hate. And it was. It was. What did we call it? Like, third month mania, because you can't say March Madness or you get sued into oblivion. But they. We, like, basically had this web app that let people vote on the things that they really disliked, and then that was used as raw material to create segments that would air on the show for the finalists. So Hasan Minhaj and Roy Wood were hosting this thing and then calling for votes online, and then that would end up in web segments. So we had this participatory, like, don't just ask the public what they want you to make. That's a little on the nose. But how do you stay in your voice and still open up some of the creativity? Build for tv, build for Internet, but also build with code and the web. That was a lot of fun. And we did a comedy hack day when I was there, taking that same model from the business I started after the Onion and bringing that into the Daily Show. And that was really cool to see. You know, there's a long way to say this. I think the short way is. One of the good things about technology is that it challenges all previous assumptions about, like, who's qualified. And that can cut both ways. But usually in an organization, there's people with great ideas that you've never asked for their great ideas, or they wouldn't have a way to express them. And so part of what our department did at the Daily show was to tap more of the building, right? More of the Daily show organization to create comedy that they didn't have room for in a 22 minute four nights a week program. But on the infinite canvas of the Internet you could experiment more. Find different jokes, find different containers for jokes that you could refill and find.

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[Interviewer Brian]

You mentioned Betaworks, which I love. You know I interviewed John for this recently. You have this peripatetic sort of lifestyle. I know you're mostly SoCal these days, but you you've seen lots of different like tech and startup scenes. Is there something to you that makes New York City's startup ecosystem or tech ecosystem different from others around the world?

[Baratunde Thurston]

Absolutely. And just to name, I mean yeah, I've spent a lot of time in the Bay. We had an office in the Bay for years in the cultivated wit era and I still go there frequently from the D.C. area and have some connection with what has happened there. That's more government leaning. Boston is a huge tech hub and center. I lived there for 12 years and have gotten to travel the world a bit. New York is special in a beautiful way. I think it's real in a grounded sense because New York isn't a company town in the way that D.C. is a government town and Los Angeles is a Hollywood town and San Francisco is a tech town. In more recent history, New York has been a bit of Wall street, but also fashion and also hip hop and also the art scene and underground. And it's a hub for global exchange. So what happens there? The grittiness of that city, the tightness of it, like the geographic tightness. You can walk block to block and experience different flavors of earth in just a few blocks. I think that has a real influence over the type of tech that gets made there. It tends, in my view, to be a little more grounded, a little more human centric, less BS in New York, if I might say so. Less pure flights of fancy. Of course, overvaluation happens everywhere in a tech scene. But I don't know, I just think New Yorkers are humble in that no one has space. You know, the public park, that's your front yard, the bar, that's your living room. And even people of decent means have roommates. And so you can't be in so much of a bubble. I mean, New York has its own cultural bubble, of course, but there's something about that proximity, that public transit. For the longest time, all kinds of people still take it. And that forces you to encounter the world. And I think when you look at the Bay, a lot of what's been created there is people trying to sever themselves from the rest of the world. It's like, I don't want friction. I don't want to encounter strangers. I don't know how to encounter strangers. I want to create experiences, technologies and whole platforms that remove me from society and allow me to do as much as I can by myself. And that we're at an extreme of that. I mean, AI is building on that promise like a. A one person unicorn. One person can make a whole Hollywood production that took 500. Okay, that's great if you don't appreciate people, but if you actually like people and think the world is better on net with them, then you build different types of technology. So I retain some hope that New York will continue to be a necessary counterpoint culturally to the types of technologies and the types of investments that have come out of Silicon Valley and the Bay Area.

[Interviewer Brian]

Before we go, how can we not talk about AI? You can't talk to anyone without talking about AI. I still have your Baratunde cocktail GPT. Actually, I have my ChatGPT window open, the one that you sent me. Not bullish or bearish on AI. Optimistic or pessimistic about AI, either for society or for what you do for creatives.

[Baratunde Thurston]

The sigh is conscious. I've spent the past year on another creation, this show called Life with Machines. And we've really been honing why we're doing it and what we think it's for. And it's for people who want to live well with technology and not just endure it. And I think a lot of what we're experiencing with tech is endurance. Like we're being subjected to the worldview of a few people who don't like people. Right. And don't like life. And I value. And a lot of my work has been in service of valuing our relationship with ourselves, with our fellow human beings and with the natural world. I've made shows on this, I've done activism around all this. And so I really, sincerely want our technologies to support that and technologies which are severing those connections with ourselves. I don't know who I am anymore with our friends. You're making me hate my friends. Or you're grotesquely manipulating the word friend to sell a surveillance appliance around my neck. Friend.com, i'm looking at you. Or to cut me off from nature or make our climate situation worse. We really don't need more of that. That is antithetical to life. So I remain optimistic because I think I'm genetically predisposed, but it's with a huge asterisk. I do not think our system default settings are toward the type of future that I would prefer to see where we do live well with technology. But the optimism remains because we still have this window to adjust course and to move it into a more life affirming direction. And I see a lot of good signs that that is happening in the US and especially beyond our borders. So I want to be a part of that. I'm working to tell those stories with the Life With Machine series and our YouTube and our Substack. And I want everyone who values life. Massive addressable market, huge tam. Huge tam. But I want us to all feel like. Actually I met this digital leader in France recently, Gilles Babinet, and I said, what do you want people to understand about AI? He didn't want a technical understanding, though. That's helpful. He's like, I want people to treat it as politics, meaning like it's a form of power and we all deserve a say in what we do with it. It's affecting our kids, it's affecting our food chain, it's affecting our water supply. And our actual politics. So we the people should, you know, use that as an open invitation to have a say in what we're going to use this technology for. So if you're down for that, let's march, let's build, let's create, let's invest differently and yeah, let's make a future we actually are excited about and something that satisfies a need. I don't know how many people need a reality destroying hyper real generative AI social media network. I truly haven't seen a huge market demand for AI slot feeds. But that's what we're being told we should want and it's worth questioning that and building something different with all this power.

[Interviewer Brian]

Again, we alighted over a bunch of stuff. Talk about returning to nature. America Outdoors is an excellent show. Very last thing. Baratunde, you mentioned the project you've been working on. What do you want people to know about right now? Where to find you, what you're doing right now? Anything?

[Baratunde Thurston]

Yeah. Find life with machines. We're LifeWithMachines Media. We're very active on our substack and about to be even more active on our YouTube with this clear view of creating a world where technology is something we can live well with and not just brace for and endure. And you can find me baratunde.com I'm on the socials wherever baratundays are found except X. Don't get at me there because I'm still feeling a certain type of way about what Elon has done with his power against so many of us. But there's a lot of other places to connect. So if that feels like something you want to be down with life with machines or just baritunde and I'll see you in these feeds, but also hopefully in these streets and maybe on some trails. Let's all go touch some grass together. Remember our connection to something bigger than a data center.

[Interviewer Brian]

Thank you my friend. It's at least kind of like refreshing for my soul to talk to you. I appreciate it.

[Baratunde Thurston]

I appreciate this opportunity to reflect a bit on my own weird overlapping journey in this scene. And just the whole New York tech scene is really. It's something fascinating. I'm going to. I spent some time this morning going through some of my archives and Alexis Ohanian judged one of our comedy hack days that we did in Brooklyn and we got him on tape just repping New York so hard versus LA or San Francisco in terms of the tech scene. He obviously lives on the west coast now and probably many places around the world, but that version of him. He was still at Reddit at the time, starting his investor life and was a podcaster too at that moment. He had a New York centric tech podcast.

[Interviewer Brian]

I remember that they had the subway ads for that for a good year.

[Baratunde Thurston]

Yeah. So yeah, it's nice that you're doing this for that culture. And thanks for including me. I also would just name drop a few other people. Kenyatta Cheese would be a really excellent person to talk to about New York tech history. Anil Dash somewhat obviously, if you haven't already talked with him. Hillary Mason I learned what data scientist was through her and as a part of my like I'm at the Onion, but I'm also hanging at Beta Works, she just got me really much smarter on things. And we ended up going to the Republic of Georgia together with a bunch of New York techie creative people to advise the government on how they might create a more innovation friendly agenda. That was like still pro people and that was because of New York. It was like there are certain things that can only happen in New York City and I think that intersection, even with international politics, creative arts, technology and media is something beautiful worth commemorating and extending. So good luck with all that.