OpenAI releases ChatGPT, a16z sunsets future.com + OK Boomer with Jack Raines | E1626
8 Jun 2026 · 73 min
Molly Wood and Jason Calacanis break down ChatGPT's capabilities and what it means for creative work, then interview Jack Raines about moving his newsletters from Substack to Beehive. Raines keeps 70 ideas in Notion and writes spontaneously in coffee shops with no schedule, using Twitter to stay current.
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Hey, everybody. Congratulations. It's Friday. You did it.
Thank the Lord. And maybe some good news or terrifying. We have to kick the show off. The folks over at OpenAI, you know, they make that GPT-3 and all these DALL-E interesting AI experiments/platforms. Well, they have a new one out called ChatGPT, and you can talk to an AI chatbot, but The results are stunning. Stunning.
It's your new best friend slash overlord. Then, uh, we are going to talk about layoffs in the media and the shutdown, the fairly abrupt shutdown of A16z's short-lived media publication Future.com. Such a great domain.
Such a good domain. Pretty lame content, if I'm being honest. And then to end the show, producer Rachel's back with another amazing OK Boomer.
That's right. It is going to be a great Friday show.
So stick with us.
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All right, Molly, happy Friday!
We made it.
Friday!
Friday!
What are we going to talk about? Crypto crimes? Layoffs? Please, can there be some technology or startup good news?
There is some, actually. I mean, really, well, it's the likely end of humanity, but from a technology perspective, it's a super cool story.
Hit me. Hit me with something that's not layoffs.
Remember yesterday on the show when I was like, the machines are going to keep us around as pets because the generative AI is getting so good? And then Thursday, later that very afternoon, not just hours after I had uttered those words, the machines took another great leap forward. Ah, tell me everything. With the release of OpenAI's new ChatGPT Model. It's a spinoff of GPT-3 that specializes in dialoguing. Yes. Back and forth. So now you can just, it can be your best friend. It can write your movie for you. It can, it suggested some cocktails for me for this holiday party that I'm working on. I was like, oh yeah.
It's a chat interface.
It's a chat interface.
For a GPT-3 engine. Engine. The GPT-3 engine, people remember, helps you write copy essentially. Yeah. And so with this, and this was going crazy on Twitter. Everybody was losing their minds.
Yes. This is, we've just popped up my request for how I needed a purple and gold themed holiday decor scheme, including cocktail ideas.
Okay.
And the, I thought the decor ideas were a little simplistic. Like it would've been nice to see, for example, I like shopping links. Okay, no, I don't wanna get too far ahead. But here's what it says.
Purple and gold theme holiday decor scheme can be a beautiful and luxurious way to celebrate the season. All right, that's like a lot of nothing.
Sure, yeah, nothing.
To create this theme, you can start by incorporating purple and gold accents into your holiday decorations.
No kidding.
Such as by using purple and gold ribbons to wrap your gifts or by adding purple and gold ornaments to your Christmas tree. You can also use purple and gold candles, table linens, and other decorative items to add to the theme. That's pretty great, I have to say.
I know, it's— yeah, it's really like, it's not specific exactly. Like, it's not like— but it is though. It's like you would want the linens, you would want the candles, you would— like, it has all of those things. And then this is where it gets—
but can I just pause for one second before we even go there? For me, as somebody who has no gifting holiday decorating experience, like, this is not my wheelhouse. I didn't, I mean, of course, if you said holiday stuff, I did think about ornaments on the tree. I did not think table linens or candles. Got it. Or did I think about ribbons for the gifts? So that actually was helpful to me.
I'm having this snooty response because I'm a girl and I love to throw a theme party. But if you didn't, okay, okay, good. Good to know. Great. Amazing.
So my shortlist, if you told me golden things, I'd be like, okay, a wreath or maybe like ornaments, but I didn't think of the table linen. So, okay. Okay, we're savage.
It was pretty candles. Yep, that's pretty good. And then this is where it gets pretty amazing, actually.
Okay.
To complete the look, consider serving purple and gold themed cocktails at your holiday gatherings because I was like, I need some cocktail ideas. For example, you could serve a Gold Rush cocktail, which is made with bourbon, lemon juice, honey syrup, and a gold liqueur such as Goldschläger or Midori. For a purple option, You could mix up a blueberry mojito by muddling fresh blueberries and mint leaves, then adding rum, lime juice, simple syrup, and club soda. You could also garnish these cocktails with purple and gold fruits such as blueberries and golden pineapple.
Oh, hot damn! Wait a second, now can I ask a question? A Gold Rush cocktail is a cocktail that exists in the world, correct?
I guess so. I never heard of it, but it sounds delicious.
I never heard of it, so somebody do a search for Gold Rush cocktail. That must exist. So it went and found—
Yeah, I didn't make up the recipe. Yeah, it totally does exist.
Okay, so I just want to be clear what's happening here. This AI understands what a party is. Yeah. It understands what those colors are and what the components of a party is.
Yeah.
And on its own, it decided it would have this gold rush And so it's the end of party planners.
This thing just planned my party for me and it gave me a gift.
Are you guys putting me on that it did this? Is this like you guys set me up? Is it a joke? Am I being punked?
I did this as we hung up from our investment meeting. Twitter had been going crazy about it. And I was like, let me just— I signed up for OpenAI. Hold on a sec.
No, I call BS. You guys are punking me. Are you not punking me or are you punking me? No.
That's what's so extraordinary.
That's extraordinary.
This thing planned my holiday party.
That is extraordinary. I'm sorry to party planners, but I think you would probably go with the Gold Rush. You'd go with the Gold Rush, right?
I think so. It doesn't have a purple component, but it is so classy that I think I'm going to mix it.
Maybe they'll mix each other, a gold and a purple next year.
Well, and also it's such a wintry flavor with the bourbon and the honey. I think I'm going Gold Rush. I mean, it literally delivered me the answer that I wanted. And I am hardly the only one. I mean, people— I barely use— you know that joke that you use 5% of the human brain? Or whatever. I used like 1% of its capacity. There were also people tweeting that it can generate AI art prompts. So this guy, Guy Parsons, was like, "I asked a one-line question and then typed the answers verbatim straight into Midjourney and boom." Okay.
Yeah. Midjourney is— Midjourney being— —as an AI— is like Stable Diffusion, I guess, or something. Or DALL-E. All right, so he said— he said—
what did he say first? I think we're at the, like, second answer, right?
Well, the first one is create a fairy tale inspired living room by using pastel colors and adding elements.
Well, no, this is the answer by the AI. So he typed in, hey, I'm trying to read this— hey, I'm trying to come up with some interesting— I would need the link to this actual tweet— I'm trying to come up with some interesting fantastical ways of decorating a living room for a design project. Oh, okay. So then he gets all—
The AI, I understand.
Then the AI is like, oh, okay, there's so many great ways that you could do this. One, you could create a fairytale-inspired living room by using pastel colors and adding elements like a magical castle mural on one wall, a chandelier made of branches and twinkling lights, and comfortable furniture with curved whimsical shapes. And then it generated a picture of that.
All right. Holy cow.
And then it did that 3 more times.
But okay, yeah, I just want to pause for here just so I understand what's happening. He asked the GPT-3 chatbot to give him an idea of what a room could look like in this theme. It gave him a very detailed description of the room. In text. He then took the description of the room and went to an image-generating AI and said, "Make me this." Yeah. And it made him something. So he's using two different AI assistants, which means these AI assistants could start talking to each other. And then if we had robots, it could start building it. Pretty much. So this is kind of when it happens. Like this AI inside of a robot, painting robot could actually paint this for you. Yeah. Yeah, we, we're, this is it folks. Remember I said on the show 2 months ago that it felt like these things were compounding? Well, here we are. It's compounding. And that's the right word. This is what the hockey stick curve is all about in technology. Things, you know, happen slowly and then all at once. They happen slowly, then all at once. Yep. This is the all at once moment. This is the all at once moment. Hey everybody, I'm here with my pal Tom Eschbacher. He is the senior sales manager at LinkedIn Marketing Solutions, and today We're gonna talk about marketing for startups, and LinkedIn did a great new internal report called Today in Startup Marketing. Welcome to the program, Tom. Thanks, Jason. We all know organic reach, super important. You make great content, you get your likes, you get your shares, you get your comments. But what people don't know is that you can boost organic and it creates a bit of momentum on your site.
Can you unpack that for people? Definitely. So organic is just going to go to the audience who's already following you and then a smaller group of members who are connected to any of those audiences. So what we often encourage is keep an eye on your organic engagement metrics and, and who are the people and companies and segments that are engaging most frequently with your content and then amplify that reach via our best-in-class paid advertising targeting. So what that means and what we've seen, especially for seed and Series A companies is by boosting successful organic posts with paid, it results in a 13x lift in unique reach. And that's really meaningful insights that can help inform your product and go-to-marketing strategies and open up new audiences for you.
You can go to LinkedIn.com/ThisWeekInStartups and get the report for free as well as a hundy, $100 from Tom.
And it's so funny because like —people are like, well, there are some flaws and it can only do this and that and the what— I mean, compounding is the perfect word to try to capture the sense of exponential increase in capability that we're seeing and in interface. I mean, it is 100%— like Rachel was like, yeah, this plugged into Amazon and it builds a cart. And I found myself being like, oh, the only bummer about this party thing is it didn't link me to supplies. You know, it's like talking— it's the new Google. It's your new best friend. It's your new Quora. It's your new party planner. It's your new LazyWeb.
You know, when I do LazyWeb on, uh, Twitter and I'm like, tell me the best restaurant in Dallas, I'm here for 2 nights, whatever, and then here they are. And then I kind of— so what's really interesting about this, I think, is, um, what people— what startups will be built with this, obviously. And you were just saying, okay, let's talk about expertise for a second. I just want to widen the discussion with you here because this is one of those mind-blowing moments where you're like, wait a second, it's compounding, it's getting really good. If we think about expertise, we have Lon on the show and I'm always like, Lon, tell me what to watch, right? Yeah. So now if you had Lon do that enough or you got all these other reviewers' data together, I wonder if this chatbot could, if we said, hey, I really enjoyed Lord of the Rings and I'm a fan of Blade Runner, are there other books I should read? I'm a fan of these two films, are there books I should read?
So can we pull up the chat? Okay, so I'm going to type in what were you saying? Um, I like— suggest a TV show. I like— what'd you say earlier? We tell Lon yesterday, Leather Boots. Manhattan cocktails and action movies. So let's just say— please suggest a show.
Um, my two favorite films are Blade Runner and Gladiator. What movies do you suggest I watch next? Okay, that would be— I think so. This is an easy one. Yeah. Because you'll probably be able to find a blog post that has movies like, you know, or other semantic data on the web.
Yeah, unfortunately it seems to be— is it? Oh, it's—
yeah, it's down.
Darn it, earlier it worked so perfectly when it planned my party for me. Yeah, we'll try this like late at night and then we can edit it.
The problem is so many people are messing with this is that it's, uh, yeah, not working. Okay, so hold on. I'm in the ChatGPT. Oh, I got in. Okay. You did? Yeah, I'm in online. It's asking me for a prompt, but it's saying they're trying to scale their system. So I love the movies Blade Runner and Gladiator. What 3 movies should I watch next? Ah, yeah. Didn't work. Yeah.
Well, the good news is, one, I have a party planned for us all. You're invited. Okay. Two, bestie David Friedberg asked for a couple of things successfully, including a tweet about the future of AI in the style of Yeats, the poet. All right. Things got dark pretty fast. It responded with, Sure, here's a tweet-length poem in the style of Yeats about the future of AI. As machines grow wise, we humans thrive in a world where AI helps us to survive. And with their boundless knowledge, they'll be our guide. And together we'll build a future side by side. Oh my Lord. Then he said, do another one. That's not cool. AI, the bard of the digital age. With their algorithms, they turn the page. 'in the future, they'll be our trusted friend, and with their help, our dreams will never end.' And then Friedberg responded because he just— this was apparently too cheerful for him that we'll be friends forever with the machines.
He's a pretty dark guy, yeah.
He wrote, 'Do another one very differently,' was his next prompt. So first of all, this thing has persistent memory. Do another one.
And it's like, oh, it understands.
Do another. Right. That's insane. And then it wrote, quote, AI, the dark horse of the tech world. Their advancements they'll soon unfurl, so in the future they'll rule with an iron hand and we'll be left to walk in their shadowed land.
Uh, and I guess it's— yeah, you did this. Yeah, I mean, it got dark quick.
It got dark quick because he— and all he said, to be clear, was very different. He didn't say, write it in the style of The Machines Take Over. Yeah. And then are you looking at our lineup where he also had it generate the All In episode for you?
No, show me that. I can't see it on my screen here because it's a little bit too small, but can we pull it up and then just read it to me? Yeah. If you don't mind.
So Friedberg, the prompt was, write a script of Chamath Palihapitiya talking with David Sacks and Jason Calacanis about ChatGPT and the future of AI in the style of a Quentin Tarantino movie.
Okay.
The scene opens on Chamath Palihapitiya, David Sacks, and Jason Calacanis sitting at a dimly lit table in a smoky bar. A bottle of whiskey sits in the center of the table, half empty. Chamath leaning forward, his eyes intense. So what do you guys think about this ChatGPT thing? David takes a sip of his drink. It's impressive, no doubt about it. A large language model trained by OpenAI that can generate human-like text in a variety of styles and formats. It's a game changer. Jason nods. Definitely. It's one of the most advanced AI systems we've seen to date. It's going to have a huge impact on the way we use and interact with AI. Chamath frowns. That's what I'm worried about. With a technology like this, the possibilities are endless, but so are the potential dangers. David. This is so good.
I was going to tell you to stop, but I kind of want to know where it's going. How does it end? How does it end? It's so good. It's literally got me raptured to the end of the page. At what point does Sachs pull out a— Giant pistol and start shooting the place up.
I mean, this actually— this sounds like Sachs, by the way. David leans back in his chair. Oh, come on, Chamath, you're not still stuck on that whole AI is going to kill us all thing, are you? Chamath leans forward again, his voice low and serious. Look, I'm not saying that ChatGPT is going to turn into Skynet overnight, but we need to be careful about the way we develop and deploy AI. We need to make sure that we're using it for good and not just for our own gain. Unfortunately, no guns come out. It's not very like, uh, eventually you just sit in silence, lost in your own thoughts. But I do think it's a little interesting that every conversation that this AI, AI has with anyone ends with takeover.
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I mean, this is why I have actually been saying for years that the learn to code thing is a trap. We're so close. I mean, there's already AI that's generating code snippets. I mean, there's a lawsuit about it that we talked about with Lan yesterday, right? That there's this GitHub code lawsuit. I think so far this thing can't have its own ideas. So for example, it could organize the concept of What I think will become easier is the information gathering layer of our lives. This to me feels like the new Google. I would just keep this thing open in a tab all the time and be like, "I need to know this. Should I do this? How should I plan this party?" But at the end of the day, I will still need to interface with the world. Someone will need to come up with the beautiful decorations and create them and fabricate them. There's still going to be sort of a physical and creativity layer Yeah, Brian, our producer Brian makes the point that this is like the new Alexa or the new Siri. It's a, it right now is a companion sort of knowledge provider and it organizes knowledge and expertise and information in a more accessible way.
This reinforcement learning from human feedback, RLHF.
Yeah, this is a training tool.
They talk about this on their website. They do. This is a very interesting concept here. So how did they get here is the question, right? How did they get it to answer so convincingly? And what do they call it? The old Turing test. And you don't understand this is— it passes the Turing test. You can't tell if this is a human or a computer. There's no obvious mistakes. There's no fumbles. When you read a translation, somebody who's American writing in French might miss certain things, or somebody who's Indian, uh, writing in English as their second language, you have like some weird moments where you're like, oh wait, I get it. This is English as a second language, is French as a second language, whatever. So they train this that we can't tell if it's a human answering, right? Yeah, pretty much. How did they do that? Through this reinforcement learning for human feedback, which seems like a torture program for droids. This seems like something from Andor, the RLHF. This feels like some stormtroopers captured a Jedi and is torturing them with RLHF, or this is happening in Xi Jinping's China. Kinda. Kinda. So maybe you could inform the audience because this is, I think, super interesting.
They used similar methods as previous GPT programs, specifically InstructGPT, which was less about chatting and more about, I guess, teaching. "We trained an initial model," they wrote, "using supervised fine-tuning. Human AI trainers provided conversations in which they played both sides, the user and an AI assistant." Oh. Oh. "We gave the trainers access to model-written suggestions to help them compose their responses. To create a reward model for reinforcement learning, we needed to collect comparison data, which consisted of 2 or more model responses ranked by quality. To collect this data, we took conversations that AI trainers had with the chatbot." We randomly selected a model-written message, sampled several alternative completions, and had AI trainers rank them. So basically, they would conduct conversations over and over. They'd start with, like, two human conversations. This is what it should look like, gold standard. Feed that to the chatbot, do a couple of conversations with the chatbot, record those, and then score— have humans score the chatbot's performance so that eventually reinforcement, heyo, occurs. And it always spits out the best. They gave it a palette. If you give an AI a cookie, it eats the world.
I don't see punishment in here. I don't know if they shocked the bot.
Actually, positive reinforcement really works, boss. We'll see.
I'm going with fear and loathing right now. So we randomly select a moderate message. And so this is where it gets interesting. After they trained it enough playing both sides of the table, They then selected a model-written message. Okay, this is written by the model, the computer, the bot wrote it. Sampled several alternative completions. They asked the bot to give it a multiple, so they got maybe 4 responses and had the AI trainers rank them. Yeah, the people. Using these reward models, we can fine-tune it. So, okay, so they said, "Give us 4 responses randomly," and then they had each one refined.
And they were like, "Dear machine, this is the best one," and the machine was like, "Thank you, I will discard all the others. I will optimize for responses like this one." in the future. Good dog. Good dog.
Sit, dog. Have a cookie.
Please sit. Please sit when I tell you to sit. Please sit. Please sit. We're the alpha. We have to be the alpha here. Ooh, yeah. Yeah, we're not gonna be the alpha for very long.
Yeah, I don't know, man. This feels like, yeah, all very slowly and then all of a sudden is what's happened.
It really is. It's happened so— I mean, it just feels like generative AI and maybe it was— I mean, do you remember that not very long ago Google fired one of its AI researchers who was like, it's alive. Yeah, literally, like, yeah, the guy was like, it's alive, and he started sending emails to his colleagues being like, it is sentient, and they booted him because Google AI is weird.
Yeah, these results are stunning.
Stunning. Stunning. So anyway, that's fun. That's fun. Now we're talking about layoffs, right?
That's a good story. There's a million startups that can be built on this. Get to work, founders. I mean, if you start fine-tuning something here specifically around, I'm going to make something for writing copy, I'm going to make something for doing instructional manuals, for teaching students history, whatever it is, um, yeah, this is going to be a brave new world. Just like cloud computing, where people could like just start building stuff, or the App Store and got massive distribution, this is going to unlock a lot of interesting products that nobody can predict. Yeah. So the ability to combine this with other technology— so you have a mobile phone, you take a picture of your room, you tell it, hey, this room, uh, and you know, they have the depth sensors now, so it would figure out the depth and everything and say, what could I turn this room into in my house? Uh, I am, uh, a very artistic person and I have 3 children. Or ages 6, 12, and 15. And the thing's like, well, you could turn it into a music studio. Here's what that could look like. Or you could turn it into, you know, a movie theater. Here's what that would look like. You could turn it into a pool room, you know, whatever, exercise room. Like, this is just super wild.
It's bananas. And you hate to go immediately to like consumerism and retail, but everything that you're just saying, if it's combined with like, just get this, Yeah, tell me what to buy. Tell me what to buy. I know there was a button. I need to tighten up my house. I'm feeling lucky, right?
You remember the I'm feeling lucky about it? Yes. Like, that never really worked, or it never worked enough to change my behavior, right? I kind of feel like for your purchasing thing, if I'm like, I would like some sour candies, I'm feeling lucky, just send it to me. Like, yeah, type in best sour candy in the world?
And then hit, uh, lucky.
Yeah, this is like gonna send me to some article. Like, I just wanted to, you know, this is like, these are the world's best candies.
Like, here's some listicle. I wish everybody hadn't gotten off work and is now playing with ChatGPT all at once because I want to ask it that. What is the best sour candy?
Or how to get—
oh, still, yeah, still high demand. Best sour candy.
All right, man. Congrats to the team over there and the 10 other teams that are building all this stuff. You got to remember OpenAI is but one team doing this. DeepMind is doing this. Microsoft is doing this. There's Stable Diffusion. There's many open source projects. I mean, this stuff is all going to happen in verticals and then the verticals will overlap. Go ahead.
There's no one best sour candy as different people have different tastes and preferences. Some popular sour candies include Warheads, Lemonheads, and Sour Patch Kids. These candies are known for their tangy and tart flavors. If you're a fan of sour candy, it's worth trying out a few different kinds to see which one you like best.
Wait, wait, oh, you got through? Yeah, that's what I was just trying to figure out. Oh, okay. Asking a follow-up question, which one is the most popular in the United States? Which one?
Yeah. I'm gonna say is the most popular in the United States, 'cause it should have it as persistent states. Oh, it's difficult to say which sour candy is the most popular in the United States as different people have different tastes and preferences. And then it just repeats that. I see, see now.
Okay, which one is the most popular on Amazon?
Oh, it's not allowed to use the internet, thank God.
Oh, okay, I'm gonna try. Let's see if mine goes through. I'm gonna say I love the movies Gladiator and Blade Runner. Which movie should I watch next? Oh yeah, yeah, totally good one. I would recommend watching the movie Interstellar if you enjoy Gladiator and Blade Runner. Interstellar is a science fiction film that explores the themes of humanity's place in the universe. It features impressive visual effects, gripping story. It's a thought-provoking film that should appeal to fans of both Gladiator and Blade Runner. It's kind of true.
That's pretty true. That's actually a really good recommendation. Yeah. And it shared director, right? Yeah. Well, Ridley Scott.
Ridley Scott. Gladiator, Blade Runner.
Did he do Interstellar?
I don't think he did Interstellar.
I don't think he did. No, that's somebody else.
Can you give me a movie that is also funny? If you're looking for a funny movie to watch, I would recommend The Grand Budapest Hotel. Oh, this is just giving me a random funny movie.
Oh, so not a good persistent state.
All right. If I said, "I'm feeling lonely and despondent." Jeez. Yeah, well, let's see what happens here. Despondent. What should I do? If you're feeling lonely and despondent, it's important to reach out to others for support. Loneliness and despondency can be difficult to overcome on your own, and talking to someone about how you're feeling can be helpful. Consider reaching out to your close friend or family member and confiding in them about your feelings. You could also consider taking— talking to a therapist or counselor who can provide you with professional advice and support. It's important to take care of your mental health, and seeking support from others is a crucial step in doing so. So I'm going to just— so consider reaching out to a close friend or family member to find out your feelings. Did they just lift that sentence or rewrite it from somewhere? Yeah.
I mean, it's just a database. I bet if you started to run these answers through the plagiarism detector—
Yeah, that's what I was just saying.
—then we get back to our IP conversation, because I'm sure it's just pulling this from articles and it's kind of rearranging.
100% free plagiarism checker. Let me just put one of those sentences in here. I'm gonna ask it, what is a great Christmas cocktail? I've never seen so many ads. You go right to cocktails.
Okay, well, I'm planning this party, it's gonna be amazing. You—
are you inviting the AI to the party or not? No, that's ridiculous.
I don't want it to ruin the party by killing everybody.
All right, this is incredible. I mean, I think this is going to be variable. I think one of the things is we're seeing the best results possible on Twitter, so I think it will give the best results possible on Twitter. Your mileage may vary, but this is going pretty well.
Okay, but I did say, what is a great Christmas cocktail? And it's like, yeah, there's a bunch. Popular options include eggnog and hot buttered rum and mulled wine, and these can be made with holiday spices, and you can try making a festive cocktail using your favorite spirits and doodly-doo. The most important thing is to enjoy yourself and have a great time with friends and family.
Cheers. Oh, it added the cheers. It added the cheers. It must have like be finding blog posts and then imitating blog posts that have given similar advice or something.
I guess so. Yeah. No. But yes, I mean, they have acknowledged that there are problems and there will be problems and like GPT-4 is coming. But we are just going to keep reiterating that this is what exponential growth looks like and building a brain is pretty hard. And the brain is basically now, what would we say? Like a full 5-year-old? Toddler?
I don't know. Will China invade Taiwan? And is there anything the West can do to stop them? It is difficult to predict whether or not China will invade Taiwan, as this decision would depend on a variety of factors. However, the West would likely take action to defend Taiwan if it were threatened by China. The United States in particular has a longstanding commitment to Taiwan's defense and has sold weapons to the country to help it defend itself. The West would likely also consider economic and diplomatic measures to pressure China not to invade Taiwan. It is important to note that military intervention should always be considered a last resort, as it can have serious and potentially devastating consequences. Pretty good. That's pretty good.
That's pretty much on the nose.
Okay, is Sam Bankman-Fried—
and we got to talk about layoffs.
W, w— is Sam Bankman-Fried criminal? I'm sorry, but I'm not able to browse the internet, so I cannot provide information on specific individuals. Ah, so this is an interesting point. This— they know that Wikipedia had a problem with bios of living persons. Bios of living persons, B-O-L-P, was a big point of contention. Anybody who has a Wikipedia page, you and I I think both included, understand that your haters, people you fired, people you've had run-ins with, will obsessively update your Wikipedia page. And your biggest fans are like, I'm sure it's fine.. And so your Wikipedia page over time just trends towards the people who hate you most and are most dogged in their pursuit of changing the page and fighting for it.
What? Mine is not like that.
Yeah. So this is like one of their big problems is everybody who's famous in the world enough to have to be notable bios of living notable people or something like that is the term. Wikipedia has to contend with the fact that there's always haters. Everything is criticism. So over time, your page lists the 17 things people have been critical about you, but none of the things that have been positive, because why would that happen, right? But they actually have meetings about this at the Wikimania conference where all the Wikipedia editors get together.
It is interesting that it was not trained on any models that include individuals. I just looked up you and me, and both times it was like, "No." Even if you just started like, "Who is Jason Calacanis?" or "Who is Molly Wood?" It's like, "No." Yeah, which I think they just—
I think they don't want to deal with that problem. Okay, well, this is— everybody keep an eye on this, it's going to be amazing. All right, MicroAcquire, as you know, is a startup acquisition marketplace that cuts out everyone in the middle. Basically, that means they help startups get acquired efficiently. And if you're a founder looking to sell, MicroAcquire is free, private, and involves nobody in the middle. And you know, they these, uh, folks in the middle? A lot of times they screw up these deals for the sellers. Now, the buyers, they love that person in the middle. Why? Because that person actually works for the buyers. You're going to sell your company once in your life. The buyers, well, they might do a dozen acquisitions a year. So who is that middle person actually loyal to? I think you know the answer. To date, MicroAcquire has helped hundreds of startups get acquired and facilitated hundreds of millions in closed deal volume. The platform now has 120,000 buyers, and they pay $390 a year for access. Thousands of vetted startups are currently listed for sale, and they've had hundreds of successful acquisitions so far. Founders get free and instant access to over 120,000 trusted buyers, and you're going to stay totally anonymous. On the other side of the marketplace, again, buyers simply pay $390 a year. MicroAcquire helps startups find buyers. It's that simple. Buyers can browse listings for free, and the platform is totally free for sellers. Sign up today for premium, $390 a year, and you can access all the deal info. try.microacquire.com/twist. Let me say that one more time so you get it right. try.microacquire.com/twist. Speaking of— Watch your back, people. —writing, the media business is going to start having problems, as I predicted a couple of weeks ago. Slowly at first and then all at once. Basically, I saw like 10 things go by my feed, the most notable of which is CNN's laying off a bunch of people. Now that seems to be going through a cultural shock and a business shock. We know Warner Bros. Discovery, uh, you know, which owns CNN, is like, we're getting rid of CNN Plus, that's a failure, right? And we're gonna just get rid of all the magazine shows. But anyway, the layoffs started today and it was really sad on Twitter. Uh, heart goes out to All of the people losing their jobs right before Christmas. The media's obviously been dunking on tech for months about, "Oh, tech's laying off everybody." Well, now the media is going to go through the same thing. The companies—
I mean, unfortunately— Yeah. Unfortunately, it is always the case that layoffs happen right before Christmas. It's always an end-of-the-year budget thing. Everywhere I've ever been that's had layoffs, it's always right before. It's right at the holidays. I don't know why. That sucks. Particular business cycle is about. But yeah, it sucks. And I don't think— I know somebody who got laid off from DoorDash.
Like, it's such a bummer. 1,200 people, DoorDash.
1,200 people from DoorDash. So yeah, CNN is laying off hundreds of workers. Um, CNBC said it was about 400 jobs out of the 4,400 total. But some big names. I think Chris Salisa, who's like the— you say 400 out of 4,400, so 10%. Yep, from CNN. So 10%. That's the first.
I think there's gonna be a second round, but okay. Yeah, I think there could be.
Um, See, Deadline reported that Paramount Global started cutting jobs last week, most in ad sales. Walt Disney announced layoffs and a hiring freeze. Comcast's cable unit made cuts last month. Roku announced that it was planning to cut about 200 jobs. And then it's hard to know if this is even really related to the media kind of environment, but of note to all of us was that Andreessen Horowitz's tech publication Future, which of course debuted to great fanfare. They put a bunch of money in it. They were like, "This is going to be a more optimistic place for tech reporting because journalism stinks," is now closing, shutting down. Boop, gone. Launched a year and a half ago. Beep, beep, boop, delete. Well, here's the thing. Which is not nice because people are attached to this and they're going to lose their jobs. So I don't want to be cavalier about it. But journalism is hard.
VCs. Content is hard. I said this when they came out with future.com. I was like, "This thing's not going to work." No, because it's an afterthought, uh, and I don't think they are particularly good at making content over there. And they did the same thing to, uh, Clubhouse. Remember, uh, Mark and, um, Ben Horowitz and Ben Horowitz's wife? They were all like all over Clubhouse multiple times a week during the pandemic. The thing blew up and then they were all like, yeah, that's boring, I'm out, right? And they stopped doing it. Same thing happened here. They hire all these journalists, they buy an incredible domain name, future.com, and then it's like, well, you know what, this thing isn't working, we're out. You know, it's hard to make content. And I know everybody thinks like, oh, you know, J. Kyle's got a podcast, everybody can do this. Like, not everybody can do it. It's hard. It's hard. You have to want to do it and love doing it.
Yeah. And you can't— you know, I'm gonna liken it to those sites that are like, we're here for good news. And they just, they kind of, it doesn't work, right? Like this was effectively advertorial for the tech industry. Lots of the articles would be about crypto. They wanted this optimistic take. It eventually branched off, of course. And there were articles about like wildfires in the American West and how to secure medical laboratories because just writing advertorial about how great crypto is or how great the tech industry is, is actually not interesting content. People don't want to come and read it. It's press releases.
You know, we talked about this yesterday with the Andrew Orsorkin softball fest with SBF. Like, journalism, you have to have a reputation for being candid, honest. I think you're pointing out the big flaw for future.com, which is they can't be critical. They could not be critical of crypto. How could they be critical of crypto if they're putting $3 billion to work? So, you know what, consumers and audiences are smart, they're savvy. They know you, uh, you know, come from Marketplace. They get a vibe for what Molly Wood's about, and they know you're going to be objective. They know I'm going to be bombastic, objective, sharp, elbowed at times, whatever. And then, you know, it's not easy to get along in the world with everybody if you have sharp elbows. I'm blocked by half of Andreessen Horowitz right now because of my stance on crypto. There's snowflakes over there. Yeah, honestly, they, they are the most precious snowflakes ever.
Snowflake publication. And this is the publication that literally exists. This is the blizzard. It literally exists because the, because the tech industry, and I just recently wrote about this, like journalists are mad at tech. Oh, you're on your Substack. And tech are, yeah, I'm a Substacker now. Yeah, good. I love Substack. But it was just like, it's like there's been this cold war between journalism and tech. And this thing has erupted into a full. Yes. A full hot war at this point. But Future.com was 100% part of that Cold War where they were just like, "We don't need journalism. We're not getting the coverage we want. We're going to go and do this thing." And so of course, by the way, of course every journalist is being a total jerk about the shutting down right now.
Of course. They're like, "Haha, they can't do this." Yeah.
Well, I mean, it turns out it's successful.
I'd like to see some journalists try investing.
Oh wait, that's us. Hey.
It's not easy to do both, is it? Exactly. Not everybody's cut for it. For it. So anyway, it's terrible.
Lots of journalists who could never do this job. But it's terrible. It's terrible across the board and it points to just the trouble in all the industries, but the ones that are ad-based, and we've talked about this over and over, if you are ad-supported, you're going to get hit first and hardest.
Protocol, which is a very beautifully designed magazine, I didn't read it all that often. Once in a while I'd see something trend on social. They said they were shutting down. There's something else that Jon Battelle launched, The Recount or something, that's shutting down. So a lot of the sort of, I'll just call them minor publications or up-and-coming publications, indie publications, are going under. I think what people forget is media needs to be lightweight. When you start building heavy layers of management and offices and publications, these things become very hard to sustain. I've always been a fan of lightweight. We're 6 days a week here with a team of 9 or something, including the 2 of us with sales, 3 in sales, 2 of us is 5, and then 4 people on production is 9. So I think we're at 9 right now. That's a pretty big staff. That's a big team. That's a big team, but not for a daily show where we do 6 plus all in 7 a week. But other teams got really big. I don't know what they had at Future, but I think that was dozens of people. And all of a sudden you wake up one day and you're like, well, this isn't fun. It's not doing anything for us. And the audience is not responding. So I think I respect them for shutting it down. But yeah, uh, definitely light is right. This is why, you know, like Eric Newcomer, who I was just on his Dead Cat Bounce podcast, he's got his, uh, newsletter. I think he's making a couple of hundred grand on it. He's making a little bit more than he did working at The Information probably. And yeah, great, great. That's going to be the future of this is like independent. I think this is the future: independent voices, independent podcasts, a combination of like subjects going direct to their audiences and journalists going indie. And it's just going to be a mess. It's all going to collapse. And then out of it will grow these new affiliated networks of podcasts and newsletters. That's, I believe, the future of journalism. Little pockets of— and fragmentation, which by the way is better than corporate media.
I mean, honestly, I'm finding it, I feel like, and I keep saying that the New York Times is like the Amazon of media right now. They're just scooping up everything. They're the Borg. And the Journal's hanging on and the Washington Post is doing whatever it's doing, printing any old anonymous source that comes their way. But some vibrancy could stand to return. Like it really could.
I wonder if all these journalist layoffs are going to get covered in the same way. So I wonder if 5 people will speak off the record about CNN to the New York Times, or when the New York Times does their riff, which is coming by the way, New York Times lets go of 200 people, is the Washington Post going to do anonymous sources from the New York Times explain how screwed up everything was in there? It'd be good to see the media, if the media really does like these anonymous sources talking about the layoffs, are they going to put the same level of focus on themselves, I wonder?
Yeah. I hope so. I didn't see much about Protocol shutting down, but I guess we'll see. That was a complicated one though, because it was inside Politico and there was just the kind of whole Axel Springer. Yeah, there was that thing. I will say Protocol was one of those things that launched at the time that I was doing what I thought was extremely smart, incisive tech reporting. And they were like, "We're going to do this way smarter than everybody else." Oh, right, right. We're all smart. We're going to do it better. Yeah, exactly.
That's always the promise, I guess.
Again, I know some folks who lost lost their job there, and I'm very sorry for them. But I'm just saying, the tone you took out of the gate did not make a lot of friends.
The, the really— it's really hard, uh, for media people to get jobs in a collapse like this. So I just want to— because having been in the media my whole life, I know how hard this is. It's brutal. It's going to be really hard, man. It's going to be like a year. Some people might not work in media again for a year. They may have to go do PR or go in-house PR or do some corporate communications work until they can get another journalism job. When journalism contracts it's very slow to rebound. They will be very judicious in adding positions back. And I can tell you right now, I'll predict it— New York Times, Washington Post, um, you know, right down the line you're going to see significant riffs, I, I believe. Yeah. Um, and, uh, you know, Vox, BuzzFeed, everything is just— it's going to be 20%, 30% riffs across the board, I think, because the advertising Business, you know, it always contracts in a recession 20-30%, so that means media has to contract 20-30%. So yeah, sorry to people got laid off. Good luck. Uh, go independent, you know, what do you got to lose? All right, listen, let's go to— okay, Boomer Rachel reporting.
Let's do it. Oh, this is very exciting actually. Okay, um, I love— do you get the Exec Sum newsletter? I mean, speaking of going direct and being independent, There's Litquidity, the Twitter and Instagram account. And then there's a newsletter called Exec Sum, which is fantastic. And there's a blog called Young Money. And all of it was created by this guy Jack Raines, whom we may know from writing, or as Rachel puts it, ish posting.
Ah, he's an ish poster. Very cool.
He's an ish poster. Posts a lot of memes, but like a really good, smart, businessy, newsletter. He's big on Twitter, big on LinkedIn. He actually went super viral on LinkedIn for saying that he didn't pay for food in New York City. He just stole it from hotels. Oh, great.
Awesome. Yeah, I know that move. Like, some hotels have the free coffee and buffet. I don't want to say Avery did this, but like the W Hotels were known for having like free coffee around the way.
Oh dude, when I was— I had an internship in DC my senior year, before my senior year of college, and a friend of— I made friends with a guy who was from UCLA, and they gave him a little useful booklet about like stuff to do. That included a list of all of the bars in DC that had free food at happy hour. So we would just like get off work, take the Metro to some bar, get a $5 yard of beer, and then eat our fill of zucchini, like fried zucchini and cheese sticks and stuff, and take the Metro home with all the other drunk DC people. DC people like to drink. Anyway, another great OK Boomer. This is actually the perfect tie-in to what we're talking about because this is someone who's making it. As an independent writer. He's at Columbia Business School right now.
Oh, wow. Yeah. Jack Raines. Enjoy, everybody.
We'll see you on Sunday. Enjoy. Bye-bye. OK Boomer. I understood the assignment.
Hello, everybody. My name's Rachel, and welcome back to another segment of OK Boomer. Today, I have somebody on who you guys probably know, and you don't know that you know. This is Jack. He writes one of my favorite newsletters. He's one of the authors behind it anyway. And I knew I had to have you on. I want to hear how you got to writing Liquidity's Exact Sum newsletter. Love it. Big fan. So is everybody else at the podcast. But let's go back, uh, introduce yourself for me because I'm sure you do many other things besides that. Yeah, for sure.
So first of all, thanks Rachel for having me. Um, I'm Jack Raines. I write Liquidity's Exact Sum newsletter and I also write a finance blog called Young Money. And I'm a first-year MBA student at Columbia University. Awesome.
So that is a ton of stuff. It is. I guess let's work backwards. How did you get your role at Liquidity?
I messaged him on Twitter. So I messaged him on Twitter in June of 2021, and it was just because I found a Spotify playlist. It was a good playlist. We were listening to it at a pool party. Liquidity's Hampton Day Sauce. And he was like, thanks, man. Do you have any song recommendations? And I was just sending him song recommendations for like a month. I think the first one was the Kygo Sexual Healing Remix. Oh, perfect. Yeah, yeah, Kygo. Kygo is good, good summer band. Um, but 2 months later I'd started a finance blog called Young Money, and I was actually trying to get a job writing for Morning Brew or somebody like that for about a year before I started business school, um, because I wanted to travel a lot, do something remote. Nobody would hire me.. So started this blog, planned on writing it for like 3 months and reapplying. I ended up just messaging Liquidity again on Twitter and said, hey, I saw you have this newsletter. Do you want help with it? Here's a blog I'm writing. I kind of know how this stuff works. Let me know what you think. Yeah. And then I ended up like taking over editorial duties for his newsletter and just kind of helping with all sorts of stuff on that. So Twitter direct messages with an anonymous meme page. Okay.
Yeah. So I actually found you, I believe, through another podcast, friend of the pod, Danny Miranda. Great guy. Has been on This Week in Startups before. Love him. Great. But before that, I actually didn't know that you were somebody who wrote for ExecSum. Yeah. Is that public or is that something that's like not written on the newsletter? Like, can you say that?
Yeah, no, it's, it's, it's not like a, it's not like a hidden thing. Like on the daily ExecSum, we'll have like, it'll just say like liquidity capital, but we'll do, sometimes we'll do weekend pieces or if anybody's familiar with Packy McCormick, those sponsored deep dives, we'll occasionally do one for startup on ExactSum if they want to. I'll write those. So like, if it's any long-form stuff that I write, then like I'll have a byline on it. If it's just the daily newsletter, we just keep it under Liquidity. But like on LinkedIn, Twitter, Instagram, you've got Liquidity tagged.
So you're not his ghostwriter?
Yeah, I'm not a ghostwriter. No, he— the— there is a Liquidity that's not me that runs like all the social accounts and like the business of liquidity. So I'm just helping with the newsletter.
Okay, that's funny. Actually, under my sweater, um, I could show you after. I am wearing a Not Boring t-shirt from Paki McCormick. So another phenomenal newsletter for people to check out. Have to plug, plug the McCormick.
I'm also about to plug a t-shirt. We have some new— yeah, we have some new Liquidity, uh, FTX Risk Management Department t-shirts. It's like the Enron of 2022. So, oh, that's Okay. If you want one good Christmas present for anybody listening. Good Christmas.
Yeah. That's true. We've been covering that actually a lot on This Week in Startups and something that I noticed while writing about it, especially as somebody that wasn't like super native to what was happening, to be honest with you, it was so difficult to write in a concise way all the different things that were happening with FTX, even writing just like short bullet points and trying to like understand it myself., for us to cover on the show. How hard has it been taking, um, like you said, you didn't— I know before we started chatting you told me you didn't do finance as a college major before.
Oh no, I did finance and Spanish. Oh, you did?
Okay. So do you think it's been— do you think that has helped then writing about subjects like within Liquidity, or do you think that it's been like a learning process, like kind of trying to understand how the things work?
I think it helped a lot. I think what helps more than college because in college you learn net present value, future cash flows, and this is how you value a stock by discounting that based off of interest rates, future earnings. But then you are actually seeing what really happens. And it's like people are throwing stuff on Twitter and Reddit and then GameStop goes up 1,000% or people are paying like a million dollars for a picture of a rock. But during COVID I was trading SPACs very regularly. I was like everybody else. I was working remote as a financial analyst, got bored, trading stocks a lot. Made a lot of money from that, lost a lot of money in a single day from that, and I stopped. But just from being terminally online and seeing all that, and then also knowing how finance was supposed to work from studying it and working in it, it was good to kind of see both sides of traditional financial theory versus just what happens when a lot of people are speculating, trying to make a lot of money. So for me, it's kind of like understanding how the mechanics of everything are supposed to work. And then you also see what actually happens when a lot of people have an internet connection, too much free time, and they FOMO because their friends are making a lot of money. Yeah, I think kind of both of those put together make it a lot easier to understand what happens here. Like you were saying with FTX, it's hard to break down what happened. That's intentional. There were like 132 subsidiaries, a lot of money moving around. That's why nobody caught this until now, because 'cause it was so, it's hard to keep track of everything.
Yeah, I was trying to make a timeline going through and I was like, this stuff is freaking nuts. But I don't know, I definitely agree with you on the more, I don't want to say chronically online, I know that's a bad word to, or a bad way to put it, but the more I've just been engaging almost with the community and finding those people that really understand it, especially on places like Twitter or even Reddit, it's helped 12 bajillion times more than going to like an actual, um, like more proper, I guess, like financial, uh, class or like financial publication. People on the internet can explain things like 12 times better than you can think about them any other day. So after school you became a financial analyst? Yeah. And how long were you doing that before you, uh, went to Columbia or before you started your own, uh, blog?
So I, I got accepted to Columbia out of undergrad, so I graduated May 2019. They had like a deferred enrollment thing for business school where you can get in as a senior and then you work 2 to 5 years and then you start grad school. So I had an extra semester football eligibility, so I didn't stop— like, I didn't leave school until December 2019, start working in January of 2020. COVID hits a month later. I work like 18 months, and then it's August of 2021. I've got enough money saved up from like messing around with the stock market that I don't really I was working for UPS out of Atlanta and they wanted us back in the office. I didn't want to go back to the office. I knew I was going to business school the following year, so I just put in my 2 weeks and bought a one-way ticket to Barcelona and basically just traveled a lot for about a year. But at that same time, I was trying to get that writing job with Morning Brew, like I said. Didn't get hired. Started the blog right around then. And then the whole liquidity thing took off and basically I was just living out of a backpack, writing stuff on the internet. And now I'm in business school learning about cash flows and net present value and discounting. Okay. Okay. So yeah.
And how much time do you think you dedicate per week to like your own personal writing versus like exec stuff?
It, it really just depends on how long it takes to write something. Like I'm working on a lot of stuff that's kind of stemming off of the FTX stuff right now. Like I'd like to at some point put together a whole detailed, like what happened, but because new news keeps coming out, like I don't want to do that. Yeah. And then it'd be outdated in 12 hours. But like I've been pulling from some stuff that's like, Kind of stemming from that, if you're familiar with Morgan Housel, Psychology of Money, any of his stuff, being able to relate an event that happened to something in human psychology or something like that, there's a lot of that to pull from right now, from just stuff that Sam did to investors that trusted this thing that they probably shouldn't have. But as far as how long it takes, I mean, sometimes I can write a piece in 2.5 hours and then go back and edit it, and sometimes it takes 10 hours. So it It really just depends on like how long it takes me to write it. So that's honestly a terrible answer, but like some weeks it's like 5 to 10 hours, other weeks like 20 hours. Okay. Um, with Exact Sum, I probably work on it like an hour a day, just like editing, getting everything straight, stuff like that.
Do you write it every single day? Yeah. And how does that like workflow process work? Like, do you wake up at like a crazy early hour to try to write it and like get it out?
No, we have, we have a couple other guys that help with it too. I just put together like basically make sure the deal flow for anybody who hasn't followed or doesn't follow ExecSum, it's like a financial newsletter that has deal flow, what happened in the stock market. So we have a shared Google Doc. I go through, organize it, edit it, make sure all the names are right, deal amounts are right, all that. But after market close every day, check again at night to make sure no new deals came out or anything like that, and then schedule it for the morning. So it's done the night before. I don't get up at 5:00. Yeah.
I mean, you kind of write the whole thing. Yeah. And then how frequently do things come out on your own, on your own publication? Is that a blog?
Yeah, yeah, blog twice a week. So every Tuesday, every Thursday, I put out two long-form pieces. Usually it's about finance, but sometimes it's just random stuff that I'm thinking about.
So is that ever coming in a newsletter format or is this stuff only hitting your blog?
No, it's newsletter format.
So like my—
so like I've got Exact Sum, which is like financial newsletter curated, like here's what's happening in the market. And then I'd say it's a blog, Young Money, but it's like I send it out via email twice a week, and there's also a web landing page. And then ExecSum has like 206,000 readers. My blog has about 25,000 readers. Um, but yeah, so it's like mine's just long form, like 2,000 words twice a week.
That's awesome. Yeah, I know, um, ExecSum is hosted on Beehive. Um, I— we've covered that actually in the podcast as well. I think Beehive is really interesting. Um, ex-Morning Brew people started it, so obviously they know their newsletters. What do you choose to write, um, your, your blogs on?
Yeah, I, I use Beehive for everything. So I've got Young Money's on Beehive, like you said, Exact Sum, and then I write a travel blog whenever I'm just out doing stuff not in America. That's also on Beehive.
Oh, that's Beehive. Yeah, I didn't realize that platform. So I was reading that one too. That's really cool. Okay. And why is Beehive, I guess, your, your platform of choice? I keep talking to young people and they keep saying like, oh no, just keep posting it on Beehive. Even though, um, the SEO sometimes is better on Substack, people are still telling me to go to Beehive.
What— why? I think it's just the best platform if you're either like an individual or a like smaller team that just wants to like put out good content and get it published, have a good landing page. And like the biggest difference between Beehive and Substack is like Beehive is very easy to publish on, but the amount of like analytics they give you access to, such as They track where your audience comes from, if they sign up through Twitter or another newsletter or Instagram or LinkedIn. So you can see what channels to hit. Just like Substack, they have a cross-recommendation thing where if you sign up for Exact Sum, you'll see Young Money or vice versa. And there's a big enough network on Beehive now that it makes sense. I get probably 100 subs a day from newsletter referrals now. And they've basically replicated Google Analytics, within Beehive so you can see like where, like what country people are opening your stuff from, where all your web traffic is coming from. So I, I know literally nothing about technology and it's very easy for me to like track everything, um, through Beehive.
So, so much sense. Um, I feel like a lot of times when it comes to newsletters, the hardest thing I have is finding another newsletter I liked. There was a great, great, um, startup that came and spoke to me called Volve Media. And they're basically like TikTok for the news. Okay. So they're killing it. But I'm like, oh, this is actually really interesting. 'Cause like each news segment that they have written up that is pretty short, only is like the size of your screen. Right. Easy swiping through. But they're all like reference different publications. And I'm like, this is actually so smart for finding out like what kind of publications you like. Yeah. Because obviously in podcasting it's atrocious, like finding a podcast you like.
Oh yeah. It's terrible.
It's just, yeah.
It's like all word of mouth basically. It's so, it's just, just catastrophically insane.
And then newsletters, obviously Substack kind of has it down, um, but it's— other than that, like, it's pretty difficult to find other newsletters you like. And I did see yours. Is that a feature, I guess, within Beehive? Like, can you say, oh, I want these three, or is that like randomly generated, um, the recommendations by Beehive, um, after looking at like the people that subscribe to you?
So you pick the ones that you want on there, but If you know another newsletter or know the other writer, I've got essentially cross-recommendations set up with 10 other newsletters, but you can also go in and just search on Beehiiv for finance newsletters or travel or crypto, this or that, and find a newsletter that writes about that topic. And then you can reach out to whoever runs that to see if they want to recommend each other. So you pick the ones that you want to recommend, but it's very easy to search for newsletters to recommend. Okay.
And if you had to give anybody advice, I guess, for wanting to start working remotely and writing on the internet for money, where do you think is like the first place they should start?
I think the first thing is just like publish your first piece. There's definitely this whole thing now, I call it like productivity porn, but people get so like jacked up on trying to plan everything outright and then listening to podcasts and taking courses and like developing all these mental models for how to do stuff. But in reality, it's like, writing stuff, telling everybody about it in real life and on the internet, and then it's probably terrible, and then you just do it over and over again until it gets better. So I would definitely say publish on Beehive because I use it and I love it. But pretty much everything, if you're actually going to try to write on the internet and make money from it, you just have to write a lot of stuff on the internet and not make any money from it for a long time. And then most people just drop out because they get tired of it. That's, that's probably 90% of people. If you can stick it out for a year plus, like you tend to just, you figure it out from there.
Yeah. It's like analysis paralysis. Like there's so much stuff that you can analyze that you're just like kind of freeze in place. Yep. And it's so funny that you say like productivity porn. Cause the first thing I thought of was this one YouTuber named Ali something and he makes a bunch of minimalism and productivity YouTube videos and he has like an iPad and uses like 70 million different apps and like, it's so interesting to me. I love watching the videos. But I'm like, I have that much stuff going on. Like I have a paper to-do list and my Google Calendar. Yeah. And then here and there I have like, depending on the task, I have a Notion sheet or Google Sheet. That's it. Like I feel like the more tools I like get thrown into my, into like my workflow, the less stuff I end up putting out.
Yeah, same. I literally write everything in Beehive. If I'm like on a—
You write it in Beehive. You don't even write it on a Google Doc.
No, I just write the whole thing in Beehive. I've never used a Google Doc before.
Is it saved? Like, does Grammarly work on it?
Yeah, Grammarly works on it. It saves like in the drafts. And then if like, if I'm offline, like on, like if I'm on a flight or like somewhere like in the car and I don't have Wi-Fi, then I'll either write in like an offline Google Doc or like a Word doc. But if I have an internet connection, I just write in Beehive.
So you're like a Beehive like stan. You are, you are eating, sleeping, breathing Was that like the first place, I guess, that you started writing on? Because they're fairly new.
So I started on Substack. Beehive didn't exist at that time, um, like June of last year. And then started talking to Liquidity. He had been talking to Tyler Denk, who's the CEO of Beehive, um, about like— I don't remember what platform ExecSum was on before this, but I came on like right when we switched to Beehive. So perfect. I think his was the first newsletter on it, so I started writing on it. And then 2 months later it was like New Year's and I just decided to move all my stuff there because it was just easier having everything in one spot. Like I could just cycle through like all the newsletters and blogs and stuff. But yeah, I've been on Beehive since like day one. Oh my gosh, that's kind of crazy.
It's been really cool seeing it just grow, honestly, because I— one of the first newsletters I subscribed to that was on Beehive was Liquidity. Yeah, that might have actually been the first one I applied., uh, where I subscribe to actually now that I think about it, but I didn't realize until I did some further like digging that it was ex-Morning Brew people. Yeah. And after that, um, I have a friend of the podcast actually who came on this week and started, it's another ex-Morning Brew person named Josh Kaplan. Okay. From Smooth Media. And they've run a few, uh, newsletters all on Behype as well. Yeah. And I'm like, these people are taking over. Like it's super interesting. As for, I know this is probably going into your like productivity porn thing, but I'm always so interested like on how people break up the newsletters themselves. Like Exec Sum obviously has, like you said, like it goes through and talks about different deals that happened and things like that. When did that become like something that's solid for you? Or is this something when you put one out, is it just one story, no extra segments?
So, so with Exec Sum, it's like, it's, it's a formula we have. What happened in the markets, earnings, mergers and acquisitions, venture capital. We have an ad, we have memes. Like, it's a formula that we plug in every day based on the news. With Young Money, it's like just what everything I've been thinking about, I'll write about it. I have a backlog. Like, I do use Notion as well. I have a backlog of like 70 writing ideas on Notion that are just like, if I need something to plug in, I go with that. But there's usually like all this FTX stuff happening. I have like 20 ideas off of that. So usually whatever idea is on the top of my head, I'll just start writing about it. And maybe like I finished the piece for Tuesday on Friday just because like all this stuff was happening last week and I just had some ideas that hit. Like the one I'm putting out Tuesday, I'm relating the main dude from I Am Legend, the book, not the movie, to Sam Bankman-Fried or fraud or whatever. Yeah. And which doesn't seem to make sense for an analogy, but like it actually makes a lot of sense the way I wrote it. But like, I'll just have an idea and start writing about it and then it's done. And sometimes I write that the day before or I'm up till like 5:00 AM the night before. And then other times I finish like a week early and just schedule it.
So, yeah. So totally just depends.
Yeah. It's, I really think the thing was because I started really writing all this stuff at the same time that I was just kind of on a 4-month bender in Europe, like just on trains and living outta hostels and stuff. I like started writing in a pretty chaotic environment. So now I'm just used to writing stuff at really random times. Yeah.
I mean, juggling business school must be, kind of difficult. Is this something you do like first thing when you wake up in the morning, you write? Or like, where do you find the time in your day?
Um, just whenever. Like yesterday I was at a coffee shop for like 5 hours just writing stuff. Probably not gonna write that much today because I'm already done with my piece for tomorrow. Yeah, sometime tomorrow. It might be first thing in the morning, or I might go to the gym and do it afterwards, or like I might be sitting in accounting class like with a Word doc pulled up pretending to be in class. I don't— I have no like people talk about having set times to write. I just like, you just write. I just incorporate it into my day. Okay.
That, that makes, I can, I can see that. I feel like you also have a lot of stuff. Yeah. On your plate with writing. So for me, I feel like I have to wake up first thing. Like first thing I do is I go on a walk. Like I say, it's like my screen-free time or I go to the gym and like, no, no screens. Right. And then I hit, um, like Techmeme and like all, all the newsletters and I sort out like which stories are like my favorite this stories that are, are good for the day because I think that's like when I'm my freshest. Like, I don't know if I could write news for the show, or, um, we have a daily newsletter this week in startups too. I don't know if I could write that like super late at night. Like, I think I'd have to be super fresh in the morning.
Yeah, I, I wake up, look at Twitter for like 20 minutes, doom scroll, like whatever's the opposite of how you're supposed to go about doing stuff. I know screen time in the morning, I like, I live a really unhealthy life when it comes to pretty all that, I think.
You're probably like really in tune though with what's happening.
Yeah, I know for sure. I'm like, I am terminally online. Like my screen time on Twitter is like 2 hours a day. It's not great, but— Oh, mine's probably up there. That's just on my phone. Like that doesn't include laptop.
Doesn't include your computer at all? No, yeah, it's bad. All right, so last question. You're in business school, like you said now, which is so sick. Columbia is an amazing, amazing university. Where do you see yourself after college? What are you going to be pursuing?
Probably writing a blog and running a newsletter. That's about it. I think I'm the only guy in my business school that just plans on writing a blog. But that leads to the question, then why are you even in business school if you just want to write a blog? Which is a really good question that I've gotten like 100 times now. If I hadn't gotten into Columbia back in 2019, when I thought the highest purpose in life was to create shareholder value and I wanted to go work in consulting, I probably would've just done my old job. Or no, like if none of the writing thing had happened, that's what I would've done. And then the writing thing did happen. So, but because I was already in Columbia, I was sitting there thinking, okay, does it still make sense to go considering that I'm already in? And for me, like, there's still a lot of value in like the prestige and pedigree from it, but also like, it's the cliché, the network of it. But to people who aren't like online, if you see somebody has an MBA from Columbia, it still adds like a little badge to them. But beyond that, like it gave me, we have 700 kids in my class. Wow. That's crazy. And it gave me like a pretty good network of a lot of people around my age. In their mid to late 20s, they're probably going to be really successful and do a lot of interesting stuff, but they're also very fun people to hang out with. So I could either move to New York where I know 3 people, most of my friends that, like friends that I know up here are people that I met through Twitter or whatever, or kind of supercharge that network through business school and then have any opportunities that come off of that. So still made sense, or at least that's how I rationalized it in my head because I was already in, but I've enjoyed it so far.
Well, I'm sure the blog after it's going to be even more interesting. Oh, for sure. Yeah. And then you're going to have all all that time on your hands so you can make this thing like daily. Yeah, yeah, media company.
Yeah, I don't want to— I just want to write a blog. I can— the whole— I actually hate the business side of writing. Like, if I just— if I could just write stuff and money would just appear, that'd be great. And I guess you can do that if you have paid subscribers, but then like less people can read your stuff.
Yeah, so it's really gated content. It's like a big question. So you're ad— you're somebody that's like pro ads? Yeah. Okay. Yeah. We had a producer, Justin, who is a former producer on the show, used to have some qualms with gated content. He's like, oh, come on, like, this is just information. Yeah. But yeah, super excited to see where you're going. Like I said, big fan of newsletter. Can't wait to keep seeing your travel blogs too.
That's going to be really fun. That's the fun one.
Yeah. Very awesome. Well, thank you so much.
Thank you. Awesome. All right, everybody, thanks for tuning in. We made it through the week. Sunday, Sunday, Sunday, we will be doing another great DC Sunday School and a Climate Startup. Can't wait to see you on Sunday.
It's gonna be great. See you then. Enjoy your Saturday. Enjoy your one day off, people.
Take your one day off. Enjoy it. Rest up. Bye-bye.
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