The AI content machine that turns ideas into posts that don't sound like slop | Alex Lieberman

1. 0:00 – 2:35

   Introduction to Alex Lieberman

   1. ALAlex Lieberman0:00

      Creating content has afforded me so many opportunities, but I am capped on the amount of time that I can spend creating content every day. And so I've been basically thinking about how can I re-engineer my content process to be AI native or AI assisted? The other problem I've been trying to solve is how do I make it as easy as humanly possible for employees to be creators while they have full-time jobs? And so that was kind of the genesis of this content machine idea, was optimizing for these two problems.

   2. CVClaire Vo0:26

      I do read your posts. They're quite good. So they don't strike me as slop, but prove it live. How would we go through this process?

   3. ALAlex Lieberman0:32

      So the first step of the content machine is called the Oracle. The Oracle just does a scan of the last seven days of information from all of the channels that I'm in, and it ranks a short list of ideas. And it has, like, a whole scoring system for what it defines as a good content spike. Gives it a positive score. I basically get 15 content spikes.

   4. CVClaire Vo0:53

      AI is just out of the box pretty terrible at writing. How do you get it to not write slop?

   5. ALAlex Lieberman0:59

      The only time, in my view, that the content machine actually produces slop is more of an indictment of the person not sharing good enough ideas during the interview step than the AI writing bad stuff.

   6. CVClaire Vo1:09

      Uh-oh. So what you're saying is we are actually the slop.

   7. ALAlex Lieberman1:13

      My take is that AI slop is hilariously people just pointing the finger at themselves and saying, "I'm not intelligent enough."

   8. CVClaire Vo1:22

      [upbeat music] Welcome to How I AI. I'm Claire Vo, product leader and AI obsessive, here on a mission to help you build better with these new tools. Today, I have Alex Lieberman at Tenex, and he's gonna show us how he climbs Cringe Mountain, AKA builds a content machine at his company by using AI. And guess what? He doesn't get AI slop out. This is an awesome workflow for anybody trying to market their company and get an edge on distribution. Let's get to it. Quick word from today's sponsor, Firecrawl. If you're building with AI agents, you've probably hit the same wall. Your agent needs data from the web, but the right pages are difficult to find, buried in JavaScript, or blocked behind logins. Firecrawl is a web data API that lets agents search, scrape, and interact with the web at scale, and get that clean, structured data they can actually use. Over a million developers, including myself, build on it. It's open source, and it's free to start. Stop fighting the web for data, and start powering your AI agents and apps with Firecrawl at firecrawl.dev. Use code HOWIAI to get 10,000 free credits

2. 2:35 – 6:56

   Why Alex built a content machine

   1. CVClaire Vo2:35

      today. Alex, I am excited about this episode because I tell everybody, in order to make it, certainly as a bootstrapped entrepreneur, you have to do one thing, and it's not vibe code. It is climb Cringe Mountain. You have to post. You have to post on X, you have to post on LinkedIn, you have to talk about yourself. And I will say, as a true engineer's engineer, I will build literally anything to avoid talking about my business. [laughs] People are surprised about this. So please tell me, how have you started to use AI? Why did you start to use AI to build the content engine at your company?

   2. ALAlex Lieberman3:16

      Well, first of all, thanks so much for having me. So I, first of all, I totally ascribe to climbing, uh, AI Cringe Mountain. I, I probably, uh, move on, like, the totally opposite side of the spectrum, which is, like, I am happy to be cringey and just, like, shoot as many shots on goal to, to sell kind of what I'm doing because my belief is people who believe that, like, if you build it, they will come, I just ... In a world in which distribution is more im- important than ever, ever before, I don't think that's necessarily the case or isn't most of the time. So basically, there have been two problems within the context of Tenex that I've been trying to solve. And just for folks that don't know what Tenex is, applied AI company helping mid-market and enterprise companies go through their AI transformation, and we do everything from strategy to for deployed engineering. So the first is I have been creating content on the internet for the last 10 years, basically since I started, um, Morning Brew when I was in college. And I think creating content has afforded me so many opportunities, but I am capped on the amount of time that I can spend creating content every day. Like, I would say 25% of my time can be spent creating content, and so I've been basically thinking about how can I maximize the value of that 25% of my time? And what I've thought a lot about is how can I re-engineer my content process to be AI native or AI assisted while making sure that I'm not putting out AI slop? Because, like, I think that's what creates so much aversion to AI for people, especially around creating content, is that it is just gonna spit out kind of just really mid stuff that sounds like everything else that's been said on the internet. The second is, you know, every business I build, whether it's a media company or a non-media company, I think we need to think more about building media companies on top of our businesses in the future, and the reason for that is in a post-AI world where technology gets more commoditized than ever before, there are fewer moats in business, and I believe that trusted distribution is one of them. So overall, I am building a media company on top of Tenex, and I think that, you know, I'm gonna do all the obvious things, like bring full-time creators onto staff, writers, we're gonna have a newsletter, all of these things. But I don't think enough companies think about turning their own employees into creators if they want to do that. And so the other problem I've been trying to solve is how do I make it as easy as humanly possible for employees to be creators while they have full-time jobs? And so that was kind of the genesis of this content machine idea, was optimizing for these two problems.

   3. CVClaire Vo5:56

      I, I love this because, one, I, I went through this myself. You know, I am a @chiefproductofficer on TikTok. I went through this phase where I was like, you know what? Part of my job as an executive when I had those jobs was to be the marketing face of the company. And you know, I used to say in SAS you were, you weren't buying the product, you were buying the roadmap. And what I would tell my team is they're not buying the roadmap, they're buying the team. Which is, like, they believe this team can execute on the vision, and so they wanna bet with either a subscription or an engagement or whatever on the team. And I talk to a lot of CEOs right now that are really unsettled by the current state of marketing, where existing channels have diminishing returns. They're not seeing the old stuff really work, and I'm ... Every single one of them I tell, "Your number one marketing channel should be your employees." And so I love that you're investing in this. Now, my, my big concern is, um, and I have a little bit of a, a, you know, content distribution engine going as well with some AI

3. 6:56 – 9:00

   Alex’s thoughts on AI slop

   1. CVClaire Vo6:56

      in it, is AI is just out of the box pretty terrible at writing compelling copy. And I think we've all seen this. We're all really critical of it, but it seems like you've figured this out, so I'd love to hear just a little bit of your process, where you think I- AI fits, where it doesn't, and how you get it to not write slop.

   2. ALAlex Lieberman7:14

      Yeah, totally. So I have a few thoughts here. We were talking about this before, which is Lulu Musservey has talked about this idea of it's a shame when the best writers in the world use AI because they cap their ceiling. And so her view is, is AI will raise the floor of bad writers, but then cap the ceiling of great writers. I think I agree with that with nuance. The, the first thing I'll, I'll say is that writing and creating content is a multi-step process which we'll go through, and I think just saying that y- using AI in any part of the content process is going to lower your ceiling is not necessarily true. I think if we were to say for the actual drafting or editing part of the content process, using AI lowers your ceiling, I can buy that and I can understand if you're a gifted writers in the top 1% of writers, how basically just banking on a model that's been trained on the entire corpus of the internet, and so by definition will be average versus you being a above average or an exceptional writer, Y would be worse. Totally get that. But there are many parts of a content process, and I think some of these parts you can use AI and still continue to actually raise your ceiling, not lower it. The other piece of it is I always think about, like, alternatives. So the alternative for, you know, our team at Tenex, and, and we can talk a little bit in a, uh, in a bit about how we're incentivizing people to create, but the alternative before this content machine was people just not creating content. And so it's like if I have two options, get people to create content around their expertise and the things that they're doing in work or not create, of course I'm going to take the first every single day of the week.

4. 9:00 – 13:24

   Mapping the workflow from scratch

   1. ALAlex Lieberman9:00

      And so what I can do is kind of take you through how I thought about my content process, and then how I transformed it. And even though we're talking about it in the context of using AI for content, m- our, our view at Tenex and my view is, like, you kind of use this kind of process mapping and then rebuilding for any process in your work. I ... This is just kind of the world that I know. Okay. So this is ... When I started this process, I basically just drew out exactly how the content process works today. So for anyone creating content, you basically start by finding inspiration. And historically speaking, the hardest thing for not even just people who are trying to create content for the first time, but, like, anyo- uh, I would actually say especially people who are creators, is finding new ideas that feel novel and interesting and just don't feel like tired regurgitation of what's been said is really hard. So first step is finding an idea. Second step, or, like, one B, is if it is an idea related to a lived experience where you feel for- fully informed about the idea, then you can skip the research step, but for a lot of ideas you'll actually have to research. Then the next step is you're gonna get all of your thoughts out on paper, um, where it's kind of like the, the, the mental vomiting of your thoughts around the idea. Next step is you decide what is kind of the anchor format that you want to create a piece of content around, whether it's long form website, LinkedIn, newsletter, et cetera. Then you write the piece, then you review a draft. You revise it, so you go through the editing process. You publish it, and then, um, as kinda Gary Vee talks about in this idea of the content pyramid, you take your anchor piece of content, you turn it into microcontent, and you distribute it across all social platforms or platforms where people consume. So this is the way ... And whether it's video or writing, this is how the process of creating content goes. And so I started with this to basically be like, this is what things look like today. Where does it make sense for AI to live in this process? And then should AI be the driver or should AI be the copilot?

   2. CVClaire Vo11:06

      I would love to just pause here, because let's put content aside. This is the exact process I tell everybody to go through when trying to figure out how to apply AI in a function, in their day-to-day, in their company. It is like taking this workflow first approach is just the most tractable way to get AI into a system. And so I'm like literally write it out.

   3. ALAlex Lieberman11:29

      Yep.

   4. CVClaire Vo11:29

      Um, and then make those decisions of, like, human, copilot, automation. The other thing that I recommend to people is I say, like, "Don't, don't workflow what you do now given your current constraints. Workflow what you would do in an ideal world given no constraints. Like, given no constraints, of course you would cut all this content into multi-channel, like-

   5. ALAlex Lieberman11:53

      Totally

   6. CVClaire Vo11:53

      ... little microcontent. Um, of course in given no constraints you'd have a researcher always on looking and mining for ideas. And so I think those two things, writing out your workflow and then also, like, removing existing constraints from how you design the workflow is really important. We have this episode with Um, Matt, the CEO of Suzy, and he does this in his marketing team where he's like he takes a, a call transcript, and he's like, "Well, how much can I extract out of this?" Not how much can my team extract out of it, but, like, in theory, and then kicks off, you know, 100 different things off of-

   7. ALAlex Lieberman12:26

      Totally

   8. CVClaire Vo12:26

      ... one piece of content.

   9. ALAlex Lieberman12:27

      Yeah, 100%. And what we've found in kind of doing this process mapping process with companies and with clients is, first of all, you end up realizing that a lot of efficiencies are found outside of even thinking about using AI because most people have not actually done the process of mapping their processes before, and AI was just, like, the force function to get them to do it, and then they find all of this waste in their process. So yeah, I totally agree with this, and this is, like, the unsexy thing to do, but I actually don't know how you reimagine the work you do if you don't start here. It's also why, like, when we talk about job loss and all of these things with AI, the only reason I was able to do this is because I've done the process of creating content, you know, thousands of times. And so it shows you the importance of, like, being a subject matter expert and having vertical expertise. That knowledge, at least right now, is really needed, otherwise you can't reimagine the work.

5. 13:24 – 23:11

   The six-step Content Machine setup

   1. ALAlex Lieberman13:24

      Okay, so basically I took this, and the next step in the process was, like, again, assuming no constraints, rebuild the entire thing. And so what came out of that was this thing called the Content Machine, and I'm gonna just show you kind of how it works just as, like, a, a visual, and then I'll take you through, like, me actually running the machine. So basically, here is how the Content Machine works. So the first step of the Content Machine is called the Oracle, and the whole idea is that the Content Machine, which is just a directory of skills, um, it is a plugin in, uh, you can either do it through the CLI or through Claude Code or Cowork, is it is connected to all of my systems of record at 10X. So my Slack, my Notion, my meeting notes, uh, Linear, Git, Gmail. It is connected to all of these things. And basically what happens is the Oracle just does a scan of the last seven days of information from all of the channels that I'm in, and it ranks a shortlist of ideas, uh, that it believes are good content spikes, and it has, like, a whole scoring system for what it defines as a good content spike. Like, if there's a story or an anecdote related, it gives it a positive score. If there's a strong point of view, it gives it a positive score. If there's specific examples, it gives it a positive score. And so every day I basically get 15 content spikes. Half of them are from the Oracle looking at my internal systems, and then the other, other half of them are doing what's called internet reading, where I have provided the Content Machine a list of the accounts that I follow on X, LinkedIn, and just the websites I go to, and it will go and look at all of the content that's been created by these people over the last seven days and share those as spikes as well. So, like, you're, you're one of the people in my internet reader, it will look at everything that you've posted in the last seven days, and when it thinks there's a good content spike for either me to do a, quote, retweet on one of your posts-

   2. CVClaire Vo15:21

      Yeah

   3. ALAlex Lieberman15:21

      ... or respond, it will share that in the list. So that's the first step in the process. That on its own is maybe the most helpful thing-

   4. CVClaire Vo15:31

      Yep

   5. ALAlex Lieberman15:31

      ... in the entire, like, in this entire system.

   6. CVClaire Vo15:34

      Yep.

   7. ALAlex Lieberman15:34

      And going back to the, the point of even if you believe that AI will create AI slop and you don't want it drafting your content, just helping you go from-

   8. CVClaire Vo15:43

      Yeah

   9. ALAlex Lieberman15:43

      ... blank page to concrete idea, I think lowers the friction so much that you'll actually get in the habit, habit of creating.

   10. CVClaire Vo15:50

       Yeah.

   11. ALAlex Lieberman15:50

       Okay, so then you select an idea, and then you go into something called the Interview Panel. And basically what the Interview Panel is, is I had six world-class interviewers codified each as skills, where there's Tim Ferriss, Joe Rogan, Michael Bar-Bar-Barro, uh, Barbara Walters, Howard Stern, and they just one by one will ask questions about this topic to you until they feel like they've gotten enough information to create a piece of content. One other thing I'll add here that's just not here is it goes straight from Oracle to the Interview Panel. If it is a topic, and I'll show you what this looks like in a minute actually in Claude, but if you pick a topic that you don't actually feel like you have all the information on already, you can run the research assistant, and the research assistant will give you a full brief into the topic. So okay, we go through the Interview Panel. Uh, basically what I do is I yap to text all of my answers, um, using Wispr Flow. Then it drafts in, in my voice. And so the way that this works with the Content Machine is basically the entire process, like, all of these steps are what live in the Content Machine repo that everyone on our team has kind of pulled down onto their computer. But separately, all of us have per... a personal folder that has codified our voice, our style guide, and, like, our sources that we wanna pull ideas from. And so when a voice is actually drafted or when a piece is actually drafted, what's happening is it's actually going into my specific voice and style guide file and using that to create the piece of content. And so just to show you what that looks like. So my style guide here is, you know, this is who Alex is. Th- uh, this is his role in the company. These are the owned assets that he's going to want to promote. These are his main anchor types of content. Here are his key integrations. Here are the social handles that he follows, follows. You see Claire's there. You know, people who give enterprise and exec lens. So that's the first, and then the second is the voice guide. And so what this is, is basically when I launch the Content Machine, it's studied. So this is all of my top performing X posts and LinkedIn posts were studied, has executive summary with voice and tone, hook formulas, content structures, latent patterns, topic categories. And so this breaks down the top 10 per- best performing X posts I've had of all time, my best performing LinkedIn posts, what my core DNA is, my Number one rule, which is writing like you're texting a friend, and then examples of, like, the language that I use, self-deprecating confidence. Like, it really goes into depth into this file. Like, this is, this is my full voice codified.

   12. CVClaire Vo18:31

       Yes.

   13. ALAlex Lieberman18:31

       And then we'll get to it in a minute, but the, the other really important piece of this whole process is when a piece of content is drafted by the content machine for me, I will give it feedback, and it will have a reinforcing loop from that feedback. And so one other file that's in the content machine is the content lessons Markdown fold, uh, Markdown file. It is all of the things that I've said it messed up when drafting my content in the past. It logs that as lessons, so around tone, where I've said the tone wasn't right, structure and flow, when that wasn't right. And so it will always check the content lessons Markdown when editing a piece of content to make sure it's not making the same mistake again.

   14. CVClaire Vo19:13

       And is this generated as you go through the editing process with a skill? Like, is it, like, if you identify some piece of feedback, are you manually populating that? How is that getting created?

   15. ALAlex Lieberman19:23

       Yeah. So the way that the content machine works is basically after a piece of content is drafted and then it goes through the editing process, which I'll show you in a second, I get the final piece of content. What I will do is I will give it feedback on that final piece of content. Once it's all done and I'm like, "This is good to go. This is good to publish," there's basically a job that's kicked off as part of, like, kind of this, uh, th- these, like, chained together skills, and it's the, the lessons loop. And the lessons loop is let me look at what the, the diff is between the original piece that we provided to Alex versus the new piece. What are abstractable lessons we can take from that? And then we ask Alex, "Do you want these lessons to be added to the lessons file?" If he says yes, then we add them in. So that's how that works. And then just to finish taking you through the process, and then I can kind of show you in practice, that's how my voice is drafted. Then the next step is, so I've share... I've picked an idea. I've yapped to text, um, all of my thoughts around the idea as I'm interviewed by this panel of interviewers. Then I pick, say I wanna create a LinkedIn post. Uh, it's drafted in my voice using my style guide, my voice Markdown file, and my content lesson Markdown file. Once the draft is done, it goes through the Writer's Council. So similar to how there's the six interviewer personas I created, there's six writer personas I created. So it's, like, David Perell, Shaan Puri, um, Morgan Housel, the, uh, the AI slop allergist, and they go through, they read the content, and they score it one to 10. If the aggregate score is under a nine out of 10, it runs a revision loop until it scores a 10 out of 10, and then it's done. And then once the piece of content is done, then I can repurpose and distribute, which means there's just a step where I can say, "I wanna repurpose this." It a- the content machine asks, "What do you wanna repurpose it into?" I could say, "Three short tweets, two long LinkedIn posts," and it will go look at what my format of writing in these different, uh, post types was in the past and write in that style.

   16. CVClaire Vo21:24

       I think, again, this is just a reflection of a, a couple things I would say. One, map your workflow. Two, w- with AI, you can bring in basically a council of experts without having a council of experts.

   17. ALAlex Lieberman21:37

       Yep.

   18. CVClaire Vo21:38

       So again, it's like in this ideal world, I would be I- I would be interviewed by the best of the best. Well, guess what? You can approximate that in your process. I think finding the right reinforcement loops on as I'm building this process, how do I iteratively make it better, because you can make sense of inputs and outputs of unstructured data in a way you weren't able to do before, is really useful. And then, um, you know, AI's, like, multimodal, and so [laughs] ... And, and I mean that not just in, like, image-to-text or text-to-voice or voice-to-text. I mean it in, like, text to mini t- mini text, text to long text. And so using all those kind of components of, of LLMs, I think makes this particular use case a good one. This episode is brought to you by Customer.io. You're here because you'd rather use AI than talk about it. With Customer.io, you describe the campaign you want to build, and the AI agent creates it for you, the audience, the messages, and the timing. You review it, make any changes you want, and launch. Instead of spending hours stitching together tools and workflows, you can focus on the work that actually drives growth. Every campaign is tied back to results, so you can see what's working and what to do next. More than 9,000 brands use Customer.io to turn the data they already have into messages customers remember. Visit customer.io/howiai to try it today. Customer.io, more impact from every

6. 23:11 – 30:38

   Live demo: Oracle, Interview Panel, and Writer’s Council in action

   1. CVClaire Vo23:11

      message. I did tell you before we got on, I do read your posts. They're quite good. So they don't strike me as slop, but prove it live. Do it live. How would we go through this, this process?

   2. ALAlex Lieberman23:21

      Let me bring up my Claude, and I'll just show you h- one example of how it already ran it, and then we'll do it live also.

   3. CVClaire Vo23:28

      Mm-hmm.

   4. ALAlex Lieberman23:28

      And I will happily embarrass myself if this goes terribly wrong.

   5. CVClaire Vo23:31

      Great.

   6. ALAlex Lieberman23:31

      So, okay.

   7. CVClaire Vo23:32

      Yeah.

   8. ALAlex Lieberman23:32

      So basically, what we're looking at is the content machine running. And, and just so you can see, 'cause this may be helpful, like, the content machine lives as a plugin in 10X's, um, our internal Claude, and basically everyone has added it to their machine. Any time I'm basically pushing an update to it on Git, people can just auto-update it right from here. Um, so I was trying to figure out something that was, for anyone who is not technical in the business, was palatable enough to, as we push updates, to benefit from those updates. And we can talk about it in a second, like, how sharing this with everyone in the business is getting us closer to what... I think it was the CEO of Sendbird who went through, like, their internal Quest, uh, thing with you, like, how we're getting closer to that. But so let me go back to this for a second So basically what this did is it first looked at my sources internal sources. It pointed out spike ideas. So this was like a single player versus multiplayer AI framework that we talked about a lot. I talked to someone at a bank who's working with McKinsey, and McKinsey gave them an idea and was like, "This is gonna take six months to build." He said he rebuilt it in a week with Claude Code. Me saying to someone on a sales call that I may be the world's worst salesperson, that sounds like a fun one. After-- I said to someone on a call, after I sold Morning Brew, I was miserable. Like, that's a good content spike. So, like, you can see it's really latching on, like, specific stories. And then from the internet reader, it pulled from the different sources that I've given it, um, in my profile file. So one was, you know, Amazon putting a billion dollars behind FDEs. Aaron Levie versus, versus Ethan Mollick talking about, like, are FDEs the solution to every enterprise's problems versus not? Everyone's a builder now. Shipping is the hard part. And so then I would just select a content spike that I want to actually build out. And just so you know here, the other thing in the content machine is, while I'm gonna select one idea here to build out into a piece of content, there are several ideas here that I think are worthy of building out. And so part of the content machine is when everyone at the company sets it up for the first time, what's created is the vault, and the vault is literally just a Notion, uh, database. And every idea that is generated by the Oracle, even if you don't use it, is added to this vault, so you can go into that in the future to pull ideas out of. Okay, so I picked spike 13. Spike 13 I thought was interesting. Aaron Levie saying, like, "FDEs are God's greatest gift to Earth right now." Mollick being like, "No, it's not gonna solve all the problems." And so I picked this, and I wanted to do more research on the topic around, like, what are the different arguments around FDEs? Why do, uh, Aaron versus Ethan have different perspectives? So then the research, uh, step was started up, and you can see basically a research brief was created for me about their takes, what's been said, what are potential contrarian or novel angles that I can take here? What are open questions that I should try to answer? So I read this beforehand. I can also, as I'm doing the interview, if I think there are, like, really good quotes from this, I can pull that into my answers as well. So then I go in, and the interview starts. So I f-I forgot Larry King was in here also. So Le-Le-Larry King is like, "Levie says FDEs win because deploying agents is more technical than people think. Mollick says they'll disappoint because the real problem is org structure and expertise, not code." And he said, uh, "You said they're both right. Here's what, uh, what they're missing." So in one or two sentences, what are they both missing? I provide my thoughts on, like, are FDEs the solution to all? Why do I agree or not with Aaron and Ethan? And then the follow-up question is just playing off of my answer. So now it asks... And, and the interview panel is really trained to pull as much specificity and examples out of me as possible. So Tim Ferriss is like, "Give me the engagement where this was painfully true, a b- uh, a build your team te- nailed technically." So it asked me to, like, give a customer story, so I did that. So we go through. I was asked five questions. Then it says, "Interview's a wrap," and "Voice and lesson's locked in." So this is where it looks at my content lessons and voice MD file. And then LinkedIn draft MD is created. So here, two of the smartest people I follow just publicly disagreed about the hottest job in AI. They're both right, and that's exactly the problem. By the way, if I was to give feedback on this, I'd be like, "This feels kind of AI cringey." They're both-- Right? Like the, the sh- two... The, the punt... Yeah, the this/that is just-- is, like, the, the newest em dash. And so I'd give that feedback, and I'd say, "Add this to content lessons." This week, Amazon committed a billion dollars to a forward-deployed engineering org. OpenAI, oh, and Anthropic already did versions of the same thing. Google is hiring hundreds. And so just it includes basically all of my thoughts here. Like, one of my answers was, "What do companies need to set themselves up for success for AI transformation?" And it took my exact words, where it was like, "So if you're staffing an AI transformation, you, you need these things." One of the reasons that this doesn't write slop mostly is because I have basically trained it to only use my words. So I think that's a big thing also is, like, this whole content machine is built on the fact that the interview I do with the panel is just turned into a large Markdown file of the transcript, and the transcript really should be the only words that are used other than maybe the hook and the conclusion. And the job of the writer is really to almost be this, like, like, sha- like shaping the clay of the content, not inventing net new things. And so the only time, in my view, that the content machine actually produces slop is more of an indictment of the person not sharing good enough ideas during the interview step than the AI writing bad stuff.

   9. CVClaire Vo29:14

      Uh-oh, so what you're saying is we are actually the slop.

   10. ALAlex Lieberman29:18

       That-

   11. CVClaire Vo29:18

       That is-

   12. ALAlex Lieberman29:19

       Oh, oh, this is-

   13. CVClaire Vo29:19

       We are the slop

   14. ALAlex Lieberman29:20

       ... my take is that AI slop is hilariously people just pointing the finger at themselves and saying, "I'm not intelligent enough."

   15. CVClaire Vo29:27

       [laughs]

   16. ALAlex Lieberman29:27

       And so-- And then the other thing it does, and I just actually recently added this in as a content lesson, is I was like, "Start giving me more examples of hooks because I want to be able to choose and compare." So it provides hooks and closings. And so what I would do here... Oh, so it didn't even run the Writer's Council yet, so let's just even do that. Run the council. So what it's gonna do now is it has the draft, it has the hooks and closings. It's gonna run the editorial council. If it's above a nine out of ten, it'll give it to me as is. If it's not, it'll run a revision loop. And then what I would do after when I get it is I will give it feedback, like the feedback I gave you around that, like, if this, then that line being cheesy. I'll go through. I'll make sure they're added to the content lessons Markdown file. And then I'll take a final pass, and I'll post this. And then my view, and this is something I wanna add to the content machine, is right now the content machine is not... When I run the Oracle, it's not pulling previous pieces of content that I should, that should think about repurposing. That should be part of the run I do every single day. And so see, they're, they're all grading it right now, and I can already tell it's not gonna be a nine out of ten, and so they're gonna run a full revision loop

   17. CVClaire Vo30:32

       Oh my gosh, I love it. And then you're gonna get this live.

   18. ALAlex Lieberman30:35

       Yep. So, like I will ... Right after we are done with this, I will post

7. 30:38 – 36:45

   Employee advocacy: the Tenex Creator Cup and $5K prize pool

   1. ALAlex Lieberman30:38

      this live.

   2. CVClaire Vo30:39

      Well, and then what I wanna say, you know, maybe what I wanna cover after we've, we've wrapped this flow, which you've kinda showed us the end to end of like how, how do we discover a good idea?

   3. ALAlex Lieberman30:47

      Yep.

   4. CVClaire Vo30:47

      How do we extract, um, via, again, our friend Hillary Gridley, um, via the Yappers API-

   5. ALAlex Lieberman30:53

      Yep

   6. CVClaire Vo30:53

      ... all of our best ideas? How do we shape that in our voice and then get some critical feedback and ship it? But you're also ... It's not 100% AI. You also have your team, and you're changing team behaviors to all embrace this new model of content creation. So can you just walk us through some of like the non-AI parts of, of your content machine and some things you're-

   7. ALAlex Lieberman31:13

      Yeah

   8. CVClaire Vo31:13

      ... experimenting with at the company?

   9. ALAlex Lieberman31:14

      So, so this actually, this conte- First of all, the ... I do not want to claim to be the inventor of employee advocacy. This has been around for a very long time. But I just think that the internet and the platforms on top of it have enabled it in a way that I don't think companies have caught up to it, or they worry so much about the risks of giving everyone in your company a megaphone that they don't end up doing it. And so I tested this for the first time at, um, one of my other businesses called Story Arb, where we did a campaign called Own the Internet, and the idea was that, uh, it was gonna be a six or eight-week campaign. Everyone at Story Arb had to post on LinkedIn, or not had to. They were encouraged to, and there was an opportunity to win money. Like, I think it was like 5,000 bucks the winner would get. And the only rule was that 50% of the content you create has to be within the world of what Story Arb does. And it ended up driving so much traffic for the business. It drew, in the quarter that we ran Own the Internet, it drove 40% of all of our inbound leads. It drove a ton of top-of-funnel for hiring. And so I just knew that I would do this. Like, any opportunity I have to do this, I will do it moving forward. And so we literally just started yesterday Tenex's version of this. And so I'll just share w- like what the, uh, details are behind it. So it's called the, uh, Tenex Creator Cup, and it's a month-long challenge to get everyone at Tenex posting. And the way you play is you just post on LinkedIn or X, and then we have a Slack channel internally called Reply Guys, and that's where everyone can just see everyone's, uh, post throughout the, uh, Creator Cup. And the way it works is every time you post, you get 10 points. Every time you engage with someone else in the company's post, you get three points. Every week, my co-founder and I will do an editor's pick of the best post of the week. You'll get plus 50. And there are weekly games, and then there's month-long games. And the whole point here is we want to encourage people to post where it's not just a race for impressions where if one person ends up crushing it with impressions, it's like y- y- we don't want people feeling like they don't have a chance. And we also want it to feel palatable for people, where just, like, playing the game is, is going to get you something. So even example this week is the week-long game this week is called Full House, where if at least 70% of everyone in the company posts at least once this week, then we unlock the one w- the week one prize where everyone gets a, a, um, lottery ticket, and we pull one person and they win a couple hundred bucks this week. And so we're giving out $5,000 of prizes this week. But the interesting thing here is, like, we were talking about this earlier w- and I, and I said, "Tenex, we're playing the game on hard mode." And what'd you say? You're playing the game on honest mode? Yeah, like I think ... So Tenex is fully bootstrapped, and I think it requires us to have to be creative with certain things, and one of those things is we truly have the best engineers that I've ever worked with in the world, and there's, there's a few reasons for that. But we do not have, like, the gravitas yet of a lab, right? Like OpenAI or Anthropic. And because we haven't raised a boatload of money also, we don't have, like, the visibility of being on TechCrunch and being mentioned by all of these top-tier investors. And so the question becomes, how do we attract top talent when we do not have all the advantages that a venture-backed company would have? Part of my view is is the way you do it is have your top talent show versus tell the cool work that they're doing. And so to me, even if the Tenex Creator Cup does not generate any leads for our business, if it just leads to more engineers knowing about Tenex and applying to Tenex, and in a perfect world if we hire one engineer from this whole campaign, well, then the $5,000 we would've paid at, we're paying out for Tenex Creator Cup is worth it so many times over, 'cause you think about what you would p- pay a recruiting agency to get one engineer. It makes it entirely worth it. And so yeah, like I just believe that, like, we le- we should lean into the bootstrapping thing, which is like have an underdog mentality, use guerrilla marketing, us all in this together to kind of create this aura around Tenex.

   10. CVClaire Vo35:27

       I just, as another bootstrap founder could ... Another bootstrap founder that's leaning on distribution as an edge, I, I completely, I completely agree. I think the other thing is we really underestimate what a employee teammate value proposition it is to say, like, "We actually encourage you to have a platform." So many companies are, like, shortsighted, because I, I actually hear CEOs saying, "Well, I don't want that person talking about how awesome they are-"

   11. ALAlex Lieberman35:52

       Totally.

   12. CVClaire Vo35:52

       "... 'cause somebody's gonna come recruit them."

   13. ALAlex Lieberman35:54

       Yep.

   14. CVClaire Vo35:54

       And I'm like, that is the number one thing that's gonna jump them out of this company is-

   15. ALAlex Lieberman35:59

       Yep

   16. CVClaire Vo35:59

       ... their inability to talk about all the amazing stuff that they're doing and build their own personal brands. And so I think that is just totally, totally spot on. And, um, again, I love to see another bootstrap founder do it. As I say, not on h- I mean, maybe on hard mode, but definitely on, on honest mode.

   17. ALAlex Lieberman36:15

       Totally. And, and even one of the things that I think about is, like, if I think about what even Anthropic has done really well on the internet is they've basically been incredible, whether, um, planned or not, at employee influencer Like, if you think about everyone surrounding Claude Code and Cowork, whether it's Tariq or Boris or Felix, right? Like, they are extensions of the brand now, and I trust their product more because they're talking about it and not just the company.

8. 36:45 – 42:56

   Lightning round: great engineers, AI use cases, slop fixes

   1. CVClaire Vo36:45

      Totally. Completely.

   2. ALAlex Lieberman36:46

      Yeah.

   3. CVClaire Vo36:46

      Well, Alex, this was awesome. This has given me so much inspiration. Um, I have a similar kinda content engine, uh, Open Claw-backed. Uh, his name is Max.

   4. ALAlex Lieberman36:55

      Love it.

   5. CVClaire Vo36:56

      But, you know

   6. ALAlex Lieberman36:57

      Hell yeah

   7. CVClaire Vo36:57

      ... same, same thing. Well, I would love to wrap with quick lightning round questions, and then we will get you out of here. One, you've said that you work with the best engineers in the world, or at least the ones that you've worked with. What do you think makes for a great engineer right now?

   8. ALAlex Lieberman37:10

      Someone who has, like, the ability to understand systems at a really deep level, like the foundational things that have made engineers always good, but who have the malleability to fully lean into making their workflows agentic. Like, I think you have a lot of really young engineers who are fully AI-pilled but don't have the foundation of knowledge that, you know, a staff or senior level engineer has. And then I think you have a lot of veteran engineers that are not malleable enough to change the way in which they work. And, and I think the other thing that comes to mind is, like, this idea of the forward deployed engineer is more important than ever before because AI transformation is only gonna happen by understanding a business' context. Um, and so yeah, that's one piece. And the other piece to it is I think the best engineers in the world wanna go long themselves. I think they wanna bet on their abilities, and that's why, like, we pay our engineers like salespeople at Tenex. People think we're crazy for doing it, but my view is I wanna self-select for people that are willing to bet on their own abilities.

   9. CVClaire Vo38:14

      I agree. You know how long I've said, like, PMs and engineers on variable comp?

   10. ALAlex Lieberman38:18

       Yep.

   11. CVClaire Vo38:18

       Forever. [laughs]

   12. ALAlex Lieberman38:19

       Yep.

   13. CVClaire Vo38:20

       Forever. I think it's the best.

   14. ALAlex Lieberman38:21

       It, it's incredible. And we still ... Like, again, there's a ton of people who give us shit about it. And look, there are trade-offs, but we have thought about all of them. And it has kept all of our people close to the frontier because the way they get leverage is by understanding what's possible with the technology.

   15. CVClaire Vo38:37

       Well, and I will hype up your people. We've had two other Tenex folks on the podcast, uh, both, both amazing. And you should go, go check out those episodes with CJ and JJ. Now, do you hire people that don't have two-letter initials names?

   16. ALAlex Lieberman38:50

       I was gonna say, I really ... I need to change my name to AJ. I really messed up the flow of the Tenex guests.

   17. CVClaire Vo38:55

       Well, I'm married to an EJ.

   18. ALAlex Lieberman38:57

       Wow.

   19. CVClaire Vo38:57

       So if you, if you need another-

   20. ALAlex Lieberman38:59

       Hell yeah. [laughs]

   21. CVClaire Vo39:00

       ... another, another J guy on the team-

   22. ALAlex Lieberman39:01

       Love that

   23. CVClaire Vo39:01

       ... um, we can do that. Okay, second question, which is, you know, you showed us your, your creative process. We've seen, you know, Cowork with JJ. We've seen coding with CJ. What about personal use cases? Like, what is an AI use case that you use in your personal life that you think is really unique?

   24. ALAlex Lieberman39:18

       So my, my wife was, um, recruiting for jobs for a period of time. She's worked in tech, and she was recruiting for jobs for a while. And I think one of the more interesting use cases that I built for her that I'm surprised a company hasn't done yet is the recruiting process is brutal. And finding com- uh, roles that are right for you is brutal. But I think we're in this age, like, people have always talked about when we're working on Morning Brew, like someone's gonna build the one of one newsletter. Like, the newslet- Like, everyone has their own customized newsletter in this world. But basically, what I built was a hiring board customized for her where every single day she got an email, and the email was 10 curated jobs based on her previous, uh, jo- like, her LinkedIn and what she's looking for and scored on that. And then she could click Apply from the email, and it would auto-fill out the initial application to the job. So that's, like, one specific use case. Uh, the other one, and this, I feel like this is, like, the classic one, is building a custom children's book. We have an 11-and-a-half month old at home. And, you know, the idea that, uh, our, our sweet Brooke can have stories that actually relate to her family, um, to me is such a cool use case as well.

   25. CVClaire Vo40:33

       Oh, I love it. You're gonna have to join our How I AI parent roundtable because-

   26. ALAlex Lieberman40:37

       Would love to

   27. CVClaire Vo40:37

       ... we have so many good use cases. Um, all right, last one I ask everybody. When your AI Oracle creative council is giving you straight slop, what is your prompting technique? Do you get mad?

   28. ALAlex Lieberman40:55

       Hmm. [laughs]

   29. CVClaire Vo40:55

       Do you cry?

   30. ALAlex Lieberman40:57

       Uh, I would say the honest answer is I will do ... It basically depends on how frustrated and how much time I have. If I'm-

Episode duration: 42:58