I run a $180M+ company...here's how I'm using AI on a daily basis
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All right, we should talk about AI because you used to tweet about like boring, steady, any cashflow businesses. And I feel like for this one, you just ripped off your clothes and you're streaking through the pool right now. So what is your take on AI? ♪ I feel like I can rule the world ♪ ♪ I know I can be what I want to ♪

♪ Falling in like no days off ♪ ♪ On the road, let's travel, never looking back ♪ - Dude, I am, for the first time in a while, I'm waking up grinning every single morning, just like stoked to get to work. I was saying to a friend, I was like, "This is like somebody just invented a new internet or something, like that's how big this feels." And he goes, "No, no, no, no. Someone just invented fire." Right? Like it's freaking crazy. And the best quote that I've heard on this is,

It's like we've discovered a new continent with 10 billion people on it, and they're all geniuses and willing to work for free, right? And so everyone's talking about this, you know, agents, right? Agents is like a meme right now. And what we're really talking about is digital employees and digital people.

And when you shift your mindset like that, you go, holy crap. Like not only is this an incredibly exciting time to be an entrepreneur, but the implications are going to be absolutely crazy. Like, you know, that saying there's decades. What is it? What is it? There's decades where nothing happens. And then there's days where decades happen. And I feel like right now, decades are happening, you know, like crazy. And here's the way I'd put it. So

If we just paused AI, we shut down all the AI labs and all we focused on was just rollout of what already exists. I think probably between self-driving cars and AI agents, 20% of all current jobs are gone. What can you explain examples of the way that you're using it now to save and make yourself more productive both personally and in a business level? Or is this mostly like theoretical where you're like, it's almost there?

Well, it's a bit of everything. So I'd say like we're in the AOL dial-up phase right now, but like AOL dial-up, it's still pretty freaking cool if you've never used the internet. You know, basic stuff that everybody should be doing. Like I'm an agent that preps me for every meeting. So 30 minutes before every meeting, I get a text and it says, hey, you're meeting Sean and Sam. You...

We're emailing them about this topic. You're going to invest in their company. And here's two bios on them. It goes to LinkedIn and just summarizes it. So something very basic that otherwise a human would do. Previously, my assistant would do that. I have it monitor my stock portfolio. I have it tell me about local events.

For the first one. So how did you set that up? How did you, what tool are you using to do the meeting prep? 30 minutes before you get a text saying, hey, you have this meeting with these people about this. So you guys know Zapier? It's basically Zapier for AI agents. So Zapier is freaking amazing. Andrew, you introduced me to someone who worked at Lindy and her name was Lindy.

And I was like, wait, you, I don't understand that. We got 25 minutes into the conversation before I realized it was just a woman named Lindy who worked at this company called Lindy. They founded the company and they were like, oh, like your name is an awesome name for a company. Let's just call it that. But it's also super confusing because she runs the sales team.

Yeah, I was like, wait, so you're, are you Smutterchild? Most people, it'd be like a quick two second thing. It's like, oh, Lindy, yeah, yeah, that's cool. How funny. And then they move on and get into the sales demo. Whereas Sam for 25 minutes is like, hold on, you're Lindy or this is Lindy? Like would not let it go for 20 minutes.

All right, so when I ran my company, The Hustle, I think we had something like 2 million subscribers and we made money through advertising. We didn't actually make that much money per person reading the newsletter because advertising in general is kind of a crappy business model. And so I remember sitting down and I'm like, what are all the different ways that I can make money off The Hustle that aren't advertising? And so to make sure that you don't make this mistake,

Sean, me, and the HubSpot team, we went and looked at a bunch of different ways to monetize your business. And we put it all together in a really cool document where we lay it all out along with our research. And we call it, very appropriately, we call it the Business Monetization Playbook. Go to the description of this episode and you're going to see a link to that Business Monetization Playbook. It's completely free. You just click the link and you can see it back to the episode. ♪

So yeah, like, so think about, think about Lindy, like Zapier, except you can build AI in between. So Zapier might be when I press this button on my phone, go to the internet and do this action or whatever, but it can't think. Lindy can add thinking in between. So for example, you can make a Lindy that looks at your calendar. So the way it would work in this instance is look at my calendar an hour before any event starts, go on perplexity.

go to LinkedIn, and I want you to write me a bio. And then I want you to look at my email inbox and tell me what we're talking about. So that's like pretty basic. And what we're really talking about at this point is removing admin work, right? So the agent that I have built is basically by cobbling it together with duct tape and dental floss. It's basically doing a lot of stuff my assistant would otherwise do. And my assistant's amazing. But the problem with

a human is they you'll give them direction and you'll say, I want you to send me these meeting briefings, or I want you to write my calendar like this. And over time there's drift, they get busy, you give them more projects and it just doesn't happen. And so now all those things that let's be real are not really worthy of her time are now just being totally automated. So that's like the basic level. And I can name some of the other tools I'm using to do this, but that that's where I'm at. So

I use Lindy to build these things when it's something I want that's custom. Are you an investor in Lindy? No, I'm not an investor in Lindy. I'm just like a power user and I'm obsessed with it. Like here's an example. So there's some restaurants in town where they still require you to call in to make a reservation. They're not on open table. I made a Lindy bot where I can type in, hey, make me a reso around 5 to 7 p.m. tonight, this restaurant, and it will call.

and an AI voice will talk to them, book the reso, put it on my calendar and invite the people I asked it to invite. And if the person says, are you AI? It'll explain that it, yeah, it works for me. And if it asks for allergies, it knows my allergies. Like it's pretty cool. And then other tools. So I use this one called Howie.ai and it's basically like a, you CC it and you just say, Howie, can you find time for me and Sam to go get a coffee? And

And it'll book all that stuff. I use Fixer, F-Y-X-E-R. It's this British startup. It basically reads every single email that comes into your Gmail. It sorts it based on whether you need to respond to it or not.

and then it drafts responses. So let's say Sean said, "Hey, do you wanna get coffee?" It'll draft a rejection or an acceptance of that in my language and it gets better over time. So those are like three tools that I'm using that are awesome right now and they're really just replacing basic admin. - This is crazy, I'm looking at this right now. Sean, where does this land with you? Do you use any of this stuff? And does this make you fearful of somewhere?

No, not really. I think everything just evolves, right? Like ultimately, you know, this diagram that's always stuck with me is like a K-shaped future. So what's a K-shaped future? So if you imagine the letter K and you say, all right, this is where we are now. That's the first line. And then it's basically like there's a fork in the road with the K, right? If you learn how to use these tools, you're going to accelerate and go up at a way faster pace than you would have otherwise.

And if you don't, if you just stick your head in the sand and pretend that these tools don't exist and that your job is always safe and that your business is going to run with all humans doing all jobs, then you're going to go down because you're going to get out-competed by companies that are going to do something different. I personally use it less for my personal and more for my business. So basically in my business, I almost have like my own eval. So Sam, you know what an eval is?

No. It's just like when a new model comes out, like when Lama drops their new model, they always post with pride like,

Oh, here's how we do on the benchmarking test, the evaluation test. And it's like some number, you don't really know what it's based off of. It's just this like abstract, like, oh, we're a 73. And the last model from GPT was a 71. So we're the best model now. And is there a standard? Like is an eval like a third party standard? I have my own little eval, which is in my businesses. I basically picked a few tasks that I'm like today humans in my companies do these tasks.

And about every sort of three to six months, we go back and we run through it again. We say, take the latest model, take the latest product everyone's excited about and see like, what's the real deal Holyfield? Can we actually automate that task? Can it actually be offloaded from the human being yet? And there's basically like a spectrum. There's like, can't do it at all.

There's you can do it, but you wouldn't actually do it. It's not good enough. Like the person, you know, that, oh, you wanted to use AI photography for your brand, but every model has nine fingers, you know, two mouths. It's like, all right, well, I'm not actually going to put that on my website. So like cool in theory, but not in practice. Then there's, you could do it if there's a human on top of it. So you could train a human to like be in the loop, to tweak it, to work with it, to make it better. And then there's, oh, we don't just, we just don't need a human doing this anymore.

And so what I've done is basically figured out, all right, here's like 10 tasks that are real tasks that we do that have a real cost and a real human doing it in my companies. And I will know for myself as we get closer to AGI, because those I'll just go from zero out of 10, which is where we started to like three out of 10, six out of 10, eight out of 10. Once eight out of those 10 tasks are like, yep, we just set up an agent and like, we don't need to have a person doing those anymore. Right.

That's when I know, oh my God, we've had real, real breakthroughs. Because that's the real test for me versus, I don't know exactly how these evals work, but it's like an abstract thing. Or it'll be like, they can pass the LSATs. It's like, that's cool, but I don't need it to pass the LSATs. If the opportunity is AI agents in my business, then I'm going to test it on

What can these AI agents do in my business? So what's the example of one of these things that you would want to automate? The simple example I gave is like e-commerce. So photography. So every month we pay photographers to do shoots. Real costs somewhere between, let's say, $5,000 to $10,000 all in for e-commerce photography. And you have basically product photography or you can have models in it, whatever, right? So there's like a little bit of a range there. So just product or models.

And so I want to know, like, when can I get rid of that 10 K a month? So when can I basically just show it my product on a blank and be like, cool, put this on models. Or we have other ones where it's like photos and videos. So I, you know, you've seen these models where you give it a static image and it

And it turns it into a video and you see the demo on Twitter and it's amazing. It's just a girl posing. And then she starts like strutting with, it turns into AI video and it looks awesome. Cool. But then like you do it in practice and yes, she starts strutting, but then her face starts morphing. Like she's like being eaten by lava. It's like, okay, I'm not gonna put that on my website. Like that would be a,

a bad thing right to do that did you see the uh ai meme of mark zuckerberg staring at bezos's wife's boobs he like leads in extra hard to like smell him do you watch that video it's literally his eyes they dart back down for a microsecond yeah and some guys made videos of him like not stopping it just continually going in it was um that's pretty badass what are we saying

Like another example would be in e-commerce, you have inventory forecasting. This seems like a data problem, right? How much inventory should I order? When should I order? And let's say, let's pretend you have five colors of a product. Which color should I be ordering? Well, it looks like an AI problem. You've got a whole bunch of historical data. You have real-time sales data that's coming in and then you should be able to forecast. And like to

Today, we employ two human beings to do that forecasting. They're not perfect at it. It's a very difficult problem to solve. Can AI make them smarter and do it better? Can I go from two humans to one human plus AI? Or can I replace the two humans and just have AI give us more accurate demand forecasting? This is a problem that every physical products brand in the world has this problem, whether it's Hershey's chocolate bars or it's North Face jackets. It doesn't matter. Everybody's trying to figure this out. How do we order the right amount of inventory and not be stuck with too much inventory?

It feels like we're talking about solar power. You remember like five, 10 years ago, everyone would be like, well, I mean, solar is really cool and all, but I mean, like, it's still not cost competitive. But if you look at the graph, it just keeps going. Cost goes down, down, down, down, down. And if you just project it.

and you look at the rate of progress with these tools, like we've been exploring for AeroPress doing the same thing. So we spent a lot of money on big expensive photo shoots and usually it's just an AeroPress sitting there really well lit with nice coffee in it. So we've been looking at Flare and some of these other tools

And I've been pretty blown away with where I can get to. And I agree there's definitely like a last mile problem, but it'll be there in the next six to 12 months, I think. And when it does, I think it's really cool for your business, but it also represents competition.

Because it just becomes infinitely easier to compete in all businesses. And we'll talk about this more, but like, I think that's, what's crazy about all this stuff, by the way, the most solved one of these is meeting meeting minutes. Like, I don't know, Andrew, if you used to do this, but I used to invite my assistant into our meetings and say, Hey, can you take notes, jot down any action items or followups that we're going to need to do? That's completely gone off her plate, which for her, it basically freed up, you know, four hours of time for my assistant a day on average, let's say.

And if now she's got four hours back that she can spend doing the other things because I'm using Fathom and Fathom just sits in my meeting, records all the notes, purges

It's perfect transcript with highlights, with a summary, with action items, ready to go 24 seven, never misses a beat. And not only did it replace him, it's way better than my assistant could do it because she'd be trying to keep up and it just was not going to be good enough. The level of accountability you can get to, right? Like I hate that feeling where it's like, oh, I did a board meeting with the CEO six months ago and I swear to God, I swear to God, they promised me this one thing. And then they're like, no, no, I don't remember that. And being able to pull that up

I just did a really cool thing, actually. Me and my girlfriend did a relationship offsite, which sounds really lame and nerdy. Patrick Campbell actually was the one that gave me the idea. But we basically would talk about, hey, what are our big strategic goals for the year, for our relationship, for family, for life in general and stuff? And we recorded the entire thing with Otter, which is a similar tool to Fathom. And I was blown away.

away. We just chatted for three hours and it was able to spit out, here's all the action items, here's all the things that need to come out of this. Then we're able to put it into Claude and it built a plan for us. Very cool. By the way, I was giving you a hard time. It does sound nerdy. And also I do the exact same thing. We have relationship meetings as well. You have the local news business, the newsletter. Sean and I both owned newsletters. When I did it,

AI didn't exist. And I felt like, you know, hiring writers was actually the hardest part, like who could write in my voice. Now I would hate to be in the newsletter business because I see this stuff and I'm like, it's almost ready to roll, but it's definitely ready to roll as an editor.

Are you using this for your newsletter now, for the local news newsletter? I'm not right now, but that's what I'm working on. So like the pieces that I'm, the more advanced stuff I'm doing are like, I've got a social media manager agent. I've got a marketer agent. I've got a tax advisor and investment analyst agent.

And I mean, these are roles I previously would have hired for where I either didn't renew someone's contract or I didn't make a new hire for them. So it's already replacing people that I would have hired otherwise. Wait, can you explain a couple of these? Explain the tax advisor one and then explain the social media one.

So, social media is very simple. It's like I post on X all the time and I'm lazy. I don't like cross-posting on LinkedIn. I often forget. I'll tweet about something and then not include it in my newsletter. And so, what I've done is I built a Lindy bot that looks at my Twitter, all my other channels, and then once a week,

It summarizes all the stuff I've been talking about and asks me, hey, what do you want to include in the newsletter? And then it can give me a first draft. And it's trained on my previous writing. So it can write. And it's not perfect, but it's like 80% of the way there. And if I didn't care about my personal brand, like many people just want like a quick and dirty newsletter, it would be totally sendable. And it's completely engaging if you prompt it right.

Right. Like you can even say, like, give me a subject line that will force the person to open the email. Right. And it's really good. What about the accounting thing?

The accounting thing is freaking like blew my mind. So basically I exported, I use Xero for all my accounting and for my personal like financials and my personal holding company, it's like a rat's nest. Like I have like 200, 300 random investments, all sorts of weird assets and stuff in there. And so I exported Xero.

All of it is a CSV out of zero. I trained a cloud project on it and I started asking it questions. Did you upload like a book, like a Warren Buffett book or like what did you? No, no, this is like basically to replace like right now. So I have a woman who runs my family office and I might ask her, hey, how much should we spend on software last week? It'll be, let's say it's a Saturday and I'm kind of bored and doing a deep dive.

I'll email her on Saturday and I've got to wait until Tuesday to get an answer. And so I was like, oh, I just want to be able to query Claude. And so I was like, hey, I want you to rank the top 25 things I spend money on. Or I want you to look at my structure and I want you to tell me if there's any ways that I could save on tax.

And so one, it was crazy. I actually saved $100,000 a year of cash taxes by moving an investment from one hold code to another. Thanks, Claude. Right. So it is very quickly becoming tax advisor, investment analyst. I can get it to write a deal. I can get it to draft legal documents like these. I mean, everyone's doing this, but like it is getting faster.

It's getting so good that I don't hire people. Let's put it that way. Weren't you hiring for like an AI back office person? Like you have some role I saw that you put up there. What was that? Yeah. So the woman who runs my family office, she's got a family situation. So she's got to transition out of the role. And so me and my president were like, okay, what do we really want out of this role? And when we thought about it, we were like, we actually just want someone who's like an AI nerd.

to automate away all the accounting and bookkeeping and stuff that nobody enjoys doing. You and Trigo came up with that? Yeah, that's right. Exactly. I hired him right out of office. But anyway, yeah, we're hiring like an AI first CFO, basically. Somebody where their job is basically just to build automations, financial automations. You guys probably have someone who works for you who just basically manages Zapier.

And like Zapier, the problem with Zapier is that it's awesome when it works, but like for some reason shit breaks all the time, which I don't understand how, like I don't understand enough about technology to know like why does shit break all the time? And then the systems were so complicated that if that person left, it was like, oh,

Oh, fuck. What's the stuff that we gotta go uncover because they've automated so much shit where it's like, we just rely solely on this one person. And it becomes actually an issue where it's kind of all automated, but it's sort of duct taped together and the duct tape comes undone and there's so much duct tape that I gotta go and fix. It's like when your Lego breaks, you gotta like, dude, I gotta like fucking rebuild this whole shit. I don't know where this one little fucking piece goes.

Totally. I've had the same experience. Like anytime I got really into no code, like four years ago or whatever. And, you know, we'd build all these automations where, oh, it'll go to this one place and then a Zapier automation will move the data into air table and then you manipulate it in XYZ way. And I think the difference here is that like

Claude will just figure it out, right? So if you say like, hey, it's not working, it'll just sort it out or tell you how to fix it. Whereas before I had that exact same problem and totally agree. Usually the automations just cause problems. How are you guys using it at Hampton right now? I mean, it's basically just like glorified Zapier, basically. So like it connects Airtable to HubSpot to this website, update these records in HubSpot. Like it's basically all backend operational stuff.

which I think is under utilizing it. Because like what I would do if I was you is I would get a... Claude has this thing called, I forget what it's called, Model Context Protocol or whatever. And you can basically build a database of all your members and then just have a way to query it where you can say, hey, we need a speaker for this event in LA. Who would be good? Or who's got a business in this space? And just have like a live database of people in an LLM. That'd be sweet. So what I'm working on though, like the next...

piece here is actually like Sean, I'm basically lining up what are the roles that we can not need in the future. And most of this is not firing people. It's actually just not hiring people we otherwise would. But if you graph this out, you can see that we're all going to have virtual employees very, very soon. And that's what's crazy. I was watching an interview with

Dario Amadei from Anthropic yesterday at Davos. And he basically said in the next 12 months, you will have AI coworkers in Slack.

Now, if you just project that out right now, it's text, right? These are not people, but pretty quick, it'll be someone on Slack that you're messaging. Hey, can you make some new product images? Hey, do you mind checking out the AdSense? Can you write a report? And I think that within 24 to 36 months, these will be 4K video people that are indistinguishable from a human that you'll talk to on Zoom. Now, I know that sounds crazy, but

But I really believe that's what's coming. And I think if you just think about the implications in terms of business moats and businesses that are going to be disrupted, it's just staggering. All right, let's take a quick break because I got to tell you about a friend of the pod who's got their own podcast. If you know Steph Smith, she is a legend. She's been on MFM many times and she's got her own podcast called the A16C Podcast.

And it's all about technology. If you think about it, technology has evolved like crazy. I mean, I grew up in the 90s. I had CDs. Phones had cords. You couldn't use the Internet if your mom was on the phone. And now there's like 3D printers and there's rockets that could go up into space. AI. There's so much crazy stuff going on. And you got to have a place that helps you stay ahead of the curve. And that's what the A6Z podcast is trying to do.

It's a podcast from the VC firm, Andreessen Horowitz. And it's trying to give you an inside look at the trends that are shaping our future. They've had guests like Mark Cuban and Neil Stevenson on, and they talk about topics like deep fakes or the science behind GLP-1s or autonomous drones. No small boy stuff at all. Steph is the host. She's awesome. I think you'll enjoy the podcast. So check it out. It is the A16Z podcast. And I like this tagline to say, it's like eavesdropping on the future. That's pretty cool. That's a good tagline. So check it out. The A16Z podcast, wherever you get your podcasts.

Do your guys' parents use it or like your 10-year-old cousins? Like how? My mom uses it. In what way?

Well, my mom's, you know, she, her first language was Hindi, right? So she speaks English. She speaks it well, but she, if she needs to write, it's kind of stresses her out. She's like, oh, I got to write something, got to write an email. I got to write a letter, respond to something, write a note to the doctor. And she's like kind of slow with writing. And she feels a little bit insecure that like her writing is going to be like well formatted, well, you know, grammar's correct and clear. And so she was early on chat GPT to just be like,

Oh, great. I can just tell it what I wanted to write. And then it just writes a beautiful email for me. And then I, what she does is she has to like kind of mess it up a little bit to get it back to real. But my mom has been using it in that way, but that's kind of all she used it. But I think what you're getting at is like, even though for us, a lot of these things we're saying right now seem obvious that you're, you're kind of right. I think if, if I know where you're going with this question, which is like, you know, my sister, my mom, like how much has it crossed the chasm? Like my sister uses it in her schools to create curriculums.

So, uh, she has it do curriculums and lesson plans and gives that to her teachers to, um, to work off of, which is something like either they would do kind of either procrastinated or, or, you know, half, or she would have to do herself. And so I think that was a big win for her, but you know, it's, it's kind of like you find your one use case of chat GPT or, you know, and you go there. Another one, like my mom was giving it like her Kaiser, like

data test results. So like, you know, you go, you get blood work done or you get a, you get some procedure done, you get this result in your app and you have to wait for this doctor to call you to tell you what the heck this means. It's kind of a scary gap of time. And we just upload all of the screenshots into chat GPT. We're like, what does this mean? And it gives us beautiful, perfect bedside manner explanations, more patient, more thorough than the doctor. You can ask follow-up questions at your own leisure and,

I mean, that's been another one that was like pretty, it was just like night and day. It's like, okay, I'll never not do this anymore. This is so much better. I'll never not do this. Andrew, you had on here that software is going to be a worse business over the next 10 years. What's your like premise here of it being a worse business? Let me zoom out a bit. So,

In a free market, the amount of competition basically defines how good a business is, right? So, you know, everybody loves to shit on restaurants, but if you own the only restaurant in town, let's say that there was one restaurant license given out in every major city and you own that restaurant. So you have excess demand. You have no competition. That would be a phenomenal business. You could have 40, 50, 60% margins. Basically, as long as people don't riot, you can charge whatever you want and the food can be bad, right? So,

I think that same thing applies to software businesses and startups, right? So if I remember, you know, 15 years ago, I started a productivity software company and it was a terrible business because every single week new VC backed companies like Asana, monday.com, et cetera, would come out and compete with us and drive us into the ground.

And where there's been a lot of wealth generated in software is in vertical markets. So what does that mean? Like, that's like, um,

weird niche businesses where nobody is competing. So for example, like funeral home management software, golf course management software, random like dam and infrastructure software. And these are great businesses because not no like amazing developer wakes up and no amazing designer wakes up and is like, I'm going to go and build this software. And so basically you're the only game in town. You can charge whatever you want and nobody switches off of you.

And so for the last 30 years, that's been the best business ever. You might have heard of Constellation Software. They built like a $70 billion behemoth public company and all they do is buy businesses like this. Don't they buy like 100 a year? They buy 100 a year. They increase the prices on a schedule. They hold them. They don't really do anything crazy or improve them in it.

in any particular way. And they're buying like $3 million a year software companies. Three to 10, sometimes bigger, but they have a formula. And so I believe let's just take funeral home software, right? So let's say that there's one developer who built funeral home software and he's had no major competition for 10 years. With tools like Replit, you

You can literally go in like, and you can reproduce basic software very, very easily. Right. If, if your software is like highly algorithmic and complicated. Yeah, maybe not, but something basic like funeral home management, where it's like case management, basically, um,

is incredibly easy to replicate in 10 or 20 minutes in Repl.it. And so my belief is basically that as more and more people don't need to learn how to code and can build software, software will become more and more commoditized. There'll be way more competition and it'll be a way harder world for software businesses. And I think that...

Ultimately, it just comes down to time. For us, all of our software businesses we've bought, we've generally bought them in a way where we've de-risked, we've paid ourselves back, or we have some sort of unique competitive advantage or cost advantage or something. Like, for example, we own a framework called

a hosting company for a framework. And a lot of people have standardized and built software on that framework. They're gonna keep hosting with us because we support that framework and nobody else does, right? There's things like that. Personally, when I'm underwriting software deals now, I am being incredibly conservative. And honestly, I'm much more focused on communities and social networks as a result. We still look at software when there's like a hardware component or there's some kind of lock-in,

but I'm much less enamored with software right now because of this. Do you guys think I'm like out to lunch on this? Am I totally overthinking this or... Say the thought out loud. What's the specific thought, right? Well, I think it's pretty wild implication that we may have...

Mass disruption in terms of jobs and mass disruption in terms of every business that we know that we think of as a good business may not be a good business. And it's not a long term, right? This is not 10 years. We're talking about a two year time horizon. So let's take the business side of it, right? The business side of your argument was basically this.

Software for the last 30 years has been an incredible business to be a creator of or an owner of, whether you're buying or building software businesses. And you're saying, I think that's going to change because if it becomes so easy for anybody to build software that they need, then they're not going to be buying $5,000 a year or $50,000 a year software anymore.

And so maybe this one thing, vertical software, VMS, right? Or other categories like that, where it's like more of a simple CRUD database where

with a user interface on top of it, that those are going to become less valuable. I totally agree with you that those are less appealing than they were before. I don't think it goes to zero because in reality, it's sort of like anytime you've actually built software, it's the last 10% that takes you. You can get 90% of the way there. You feel like you're almost there, but then the last 10% will take you as much time as the first 90. It's just like a rule you see over and over and over again. And it's the same thing with products, which is that

to actually make something work and solve all your problems that you need, that you're used to your current software solving. It will take time, effort, love, care, and whether it's just might just be somebody else building software that's a competitor to you or, you know, if it's somebody in your own company going to build that. I think it's,

less likely that that becomes like a major disruption to all of software. Because like you were saying, like some software, like social networks or communities, the value is not the app, the value is the people and the connections and the habits that they formed. So you have software where there's already habits, those will be safe. Software where the value is the people or the data, those will be safe. Software where the value is in the enterprise relationship, the service that's on top of it, or the like fine tuning and tailoring and the CYA, which is that

If I buy enterprise software, I don't need to save 40% on this bill as much as I need to not get fired for being like, yeah, we homebrewed our entire CRM and like the security wasn't very good, right? Because we didn't, I made this in fucking Claude instead of it being software I bought from a vendor that's been doing this for 15 years and has actually like solved the security vulnerabilities. And so I think that enterprise software will be safe. So I think a lot of software will be more safe than software just as a category goes to zero.

Yeah, I would generally agree with that. Although I think it's going to be a lot easier to offer incredible sport, incredible sales, etc. On the other side of it, you get the market expands, right? Because it's not just that, oh, there's going to be more competition in this fixed pie. It's that now a whole bunch of software that really wouldn't have made sense to build because...

Coders didn't understand the problem, so they weren't working on it or you would have need too much funding to build it. It's not really worth it. So all this new software is going to get created that was not really feasible or wasn't really easily accessible before. Like I'll give you like a stupid example. I went on Replit the other day and Replit's amazing because it's literally chat GPT except for when you tell it something, it makes a website for you or makes an app for you.

And so I had this like, you know, first world selfish problem, which was that I like to log my meals. I take photos of my meals when I, when I eat them to be able to send to my coach. But then my entire camera roll is just shitty pieces of chicken and my kids. It's like beautiful pictures of my kids and then ugly pictures of chicken. And I'm like, all right, this is kind of annoying that that's there. So I just told Reply, I said, make an app that when I open up the app instantaneously, the camera is on. I don't want to like

type in stuff. I just like open the camera, take the photo, show me a thumbs up or a thumbs down where I can rate my own meal and then save it in a calendar view where I can see like a streak of, you know, if I've been doing roughly good, make it green. If I've been doing bad, make those red. And can it make it an app that it gets approved in the app store? So that was so immediately represents like, Hey, I can't make iOS apps yet, but I can make it as a website. You could add it to your home screen and you could use it on your phone, but it'll just be a website you open up. I was like, all right, deal.

And then it made that app for me. And it's like, you know, it's not perfect. Like I ran into some walls where that replates like, Hey, I don't know why it's not working. I'm like, yo, it actually is working. And it's like, you're, you're just being crazy, but like, you know, okay. You get through the craziness and it's not exactly good enough. I would say like, I I'm using it every day and telling you guys how amazing this, this tool is, but nine months from now, pretty sure I'm going to be able to just do that. Right. So like I can be a software creator without knowing how to code. That's already a big, big deal because of that.

Any idea I have, I can make come to fruition. So a whole bunch of new ideas are going to come into the market that didn't exist. And I could do it for like other problems that weren't going to get solved maybe through like, you know, if you look at software today, it's like a lowest common denominator. Like I need to serve the most customers who are willing to pay. So I'm going to like shave off all the edges and make some product that's what I think most people want, even if it's not what I personally want, right? Or what me and a cluster of people like me really want.

And so I think the overall market for software gets bigger because you can create way more stuff. So, so that's the other counterpoint to like software being bad. It's phenomenal for consumers, right? As a consumer, I'm so excited. It's more, if you're buying these businesses and you're underwriting 10 years of returns, continued profit margins, all that kind of stuff. I think it's,

It just got a lot harder because before it was like, look, there's only so many programmers out there, right? There's only so many competent Mac OS, iOS, whatever programmers. And I'm with you in terms of like where Replit is at right now, where it's like, yeah, you gotta fiddle a lot to get it to a point where it's shippable. I've built a lot of stuff that is 90% that I can't put out into the world because it's not there yet. But I think it's a little bit like stock photos.

Two years ago, stock photos generated by AI were terrible. Now I would not want to be in the stock photo business because it's perfect and it's only getting better. I will say one other thing. This same thing happened with media. Before, only people who could make media were media companies. There was limited TV channels, newspapers. If you owned one of them, it was amazing. If you didn't, it wasn't. You're right that owning those legacy media businesses...

kind of sucks in the world of social media where anybody can create content. And so those businesses went down, but then suddenly new businesses, which are social media based, emerged and the set of social media based businesses are way bigger than the set of legacy media businesses. And if you're interested in whatever weird niche, you don't have to rely on the Wall Street Journal to write about it.

Right. So I think it nets out way ahead. I don't know if you guys heard Larry Ellison yesterday when he was like going off about AI, like people like, well, what are you excited about AI? And he like did this little rant, which I don't know how well versed Larry Ellison is in like

What's actually possible with AI versus like Masa-san showing a picture of a golden goose laying eggs and being like, that's why I'm investing. But he was like, with AI, here's what's going to happen in the next few years. He was like, you're going to be able to do early detection of cancer. Then the AI is going to sequence what cancer you have. It's going to be able to design a personalized vaccine for your cancer and cure you of cancer.

So why am I investing a hundred billion dollars? Because I want that. And I want a hundred other things like that.

And it was just like a very compelling rant he did outside. Did he deliver it in that type of compelling way? Well, nobody's me, but yeah, he did the Larry Ellison version of it, the B plus. But he did do like, he was able to dumb it down. He was basically like, it was like he was shaking somebody and be like, do you hear what I'm saying? Do you know what this is? Get this in your little head. It's not about an investment for a data center. It's

We're going to cure cancer with this shit. Okay. And it's going to save your, like your mom's life. Like you were, that's what we're going to do with this thing. Okay. That's, that's why we're doing this. Let's not get caught up in project Stargate and politics and the, the investment amount and the infrastructure. Like, okay, all that's a means to that end is kind of the way he was saying it.

Dude, this shit's so exciting. He also, I think he's obsessed with living forever. I think he's one of these guys who's like into that and is the 10th richest guy in the world. So he can kind of throw his weight behind a lot of that stuff. And I think that's pretty badass. And that's probably a huge motivator. Andrew, can we do one more? You had this great thing in your notes that I want to hear you explain. You said AI hedge. Basically, you were looking for investments, given that you think, okay, software might not be the best place to be investing.

Where are you investing? And what is all the stuff I see here down below your AI hedge notes? Sure. So I feel like there's a bunch of different scenarios here, including that this scaling slows down and it's a moderate disruption. We've got a couple of years of some people being unemployed and then they rescale. They go do different things. Like you said, the economy gets bigger, whatever.

There's another possibility that there's what's called an AI fast takeoff, which is like Masa's graph of like the singularity happens and it's crazy. And if that happens, it's like, does capitalism matter? Does the free market matter? Does the AI basically just become this like communist overlord that allocates assets and stuff? But I've been thinking about, what do you wanna own in a world where that happens? So you can go out and you can try and buy secondary in Claude or...

or Anthropic or OpenAI, those are very expensive. You can buy Nvidia at 30 times earnings or ASML at 30 times earnings, some of these, or TSMC, but there's the Taiwan risk, all the other stuff. And so I've been trying to find stocks that I can buy that are actually affordable, but capture AI upside. And I found a really interesting one.

I love stuff that's miscategorized and misunderstood by public market investors. Public market investors are very simple in the way that they think about companies. They have a series of boxes and they filter you through the boxes. And there's a saying, you want to look like a duck and quack like a duck in the public market. They do not like complexity. And so if you say the wrong keyword, they're

their brain turns off and they just say, I'm not going to invest, right? And so a couple of those examples are cannabis, right? They just put you in a box. Biotech, oh, high risk. And Bitcoin is another one. There's all these crappy Bitcoin mining companies. Dude, when we sold the company to HubSpot,

one of the reasons we went into the year with millions and millions of dollars booked of advertising. And we were probably going to do $20 million the next year. And they were like, yeah, just cancel all those contracts and give the money away, give the money back. And we're not going to do advertising anymore. And I was like, but you could scale this to like a lot, to tens of millions or whatever. And they're like, yeah, we make billions of dollars a year. And also we would just have to report that. And that's a little too complicated and people won't understand it. So like the decision of them to not...

do that was worth more than the tens of millions of dollars of advertising revenue they could have made, which is wild. Have you ever met one of those like really ADHD young entrepreneurs who's pitching you on their business and they're like, oh, we do this, but we also do this. And also I've got a company that does this.

And we all, the older statesmen, we always are like, young Padawan, just focus and don't do that. Or if you're going to do that, don't tell me about all this other stuff because it just confuses me. I feel like public market investors are like that. So here's the business I found. It's called Iris Energy. The ticker is Iris.

I-R-E-N. And basically it's these two Australian guys who were infrastructure bankers and their thesis supposedly was that compute was going to be a big deal in the next 10 to 20 years. So presciently they went out, they secured a whole bunch of huge data center properties that were right next to mostly renewable energies.

So they'd find a power plant that's like a hydroelectric dam or something like that. And they would literally just buy a massive data center right next to it and build one. So for example, where I live in BC, they have one in Prince George right next to like a big hydro dam. And currently...

The best use for these data centers they've built so far has been mining Bitcoin. So they've been doing that and they're not Bitcoin bolts. They're not like MicroStrategy or someone like that. They don't hold the Bitcoin. They just mine it. They've got their GPUs and whatever, and they sell it immediately. And right now they're making somewhere in the range of $500 million of EBITDA annually doing that.

Now the stock trades at about a $2.4 billion valuation. So you can buy it actually quite cheaply based on the Bitcoin thesis, right? And Bitcoin would have to drop by about, I believe, I'm guessing based on some assumptions, but I think it would have to drop about 70% before they get to break even on mining these Bitcoin. So

Here's what's interesting about this business. So it's totally misunderstood by the public market because everybody thinks, oh, they're Bitcoin bulls, they're mining Bitcoin, there's all this risk or whatever. What's actually interesting here is they're going to flip, I hope,

or they've kind of publicly communicated to some degree that they're going to try and flip these data centers over to compute. So all these huge companies like, you know, Amazon and Microsoft and Anthropic and whatever, they all need data centers and they need the data centers to be centralized in one place. You can't have 10 computers here or 10 GPUs here and 10 GPUs somewhere else. For training, you need them all to be in a massive supercluster.

So, the other interesting thing is, you can't just go and build these super clusters you can't go build these data centers anywhere it takes a long time to get permitting and approval, and it takes a long time to build. And so basically there's a finite amount of this stuff to the point where you guys have probably heard like Bill Gurley talking about like trying to buy nuclear power plants and all sorts of crazy stuff. So, basically,

Basically, if they flip this business over to doing inference and to working with hyperscalers on training, this could be a massive boost to the business. And it could 5, 10, 20x, I don't know. But very significant if they sign some deals with hyperscalers, which I know that they're actively working on. They've communicated as much. So basically, if you believe in a fast takeoff, it's a very interesting thing.

way to kind of buy something with relatively low downside and very significant upside instead of buying Nvidia or Microsoft. Obviously... You sound like you're Leonardo DiCaprio in... Yeah, exactly. Do your own research. This is not investment advice. I do own the stock, but I think it's interesting. How much of the stock did you buy? I only bought like a million dollars, but I look at it as like a small... It's a very small position. It's like buying fire insurance. Yeah. What is this? A position for ants? Just a million dollars, Andrew? No.

well andrew i know that was not financial advice but i do appreciate the advice that you just gave me financially the last public stock we talked about i think was weight watchers and like

There was definitely a correlation from when the episode aired and when the stock... I don't know if it was causation, but there was definitely correlation. I wonder if that's going to happen here. You said the downside is like you have this Bitcoin mining free cash flow priced very fairly, right? You said like 3x free cash flow basically is the price. And then the upside is if they make this AI switch. One question, you said they...

It sounds like they're not huge super clusters, so. - Oh no, they are huge. So they have a massive site in Texas that they're working on building. Now here's probably the reason why it's trading lower is these profits do not just go to investors. They are almost all being pounded back into building out these data centers.

So if for some reason compute stops mattering or, you know, we move to distributed inference or something like that, there's definitely a downside scenario, which is why I'd say, think about this cautiously. Don't put your entire portfolio in it. But I look at it as it's like a good one to 5% position.

So I'm obsessed with being transparent about money, particularly with ultra high net worth people. The reason being is that there's not a lot of information on this demographic. And so because I own Hampton, which is a community for founders, I have access to thousands of young and incredibly high net worth people. We have people worth hundreds of millions and sometimes billions of dollars inside of Hampton.

And so every year, we do this thing called the Hampton Wealth Report, where we survey over 1,000 entrepreneurs, and we ask them all types of information about their personal finances. We ask them about how they're investing their money, what their portfolio looks like. We ask them about their monthly spend habits. We ask them how they've set up their estate, how much money they're going to leave to charity, how much money they keep in cash.

How much money they're paying themselves from their businesses. Basically, every question that you want to ask a rich person, we went and we do it for you. And we do it with hundreds and hundreds of people. So if you want to check out the report, it's called the Hampton Wealth Report. Just go to joinhampton.com, click our menu, and you're going to see a section called reports. And you're going to see it all right there. It's very easy. So again, it's called the Hampton Wealth Report. Go to joinhampton.com, click the menu, and then click the report button. And let me know what you think.

I need to look into it. That's not how I roll, obviously. But it was compelling and I...

I'm fascinated by their entrepreneurial story. I'm amazed how this was just launched in 2018 and how fast they grew. How much financing did they raise? I don't know how much they've raised, but I do know that they have no debt, which is quite impressive for a business like this. They have a lot of interest in retail, like a lot of retail buyers in the public market. And so they've been, every time they need to expand, they do what's called an at-the-market raise. So they basically just issue stock into the market and then they raise capital to do it that way.

Um, but,

But I mean, the way they die would be big amounts of debt. So they're avoiding that, I think. Well, I forget what that online stock market club is that like Bill Ackman and all these billionaires are part of where they got to pitch their stock and they have to make a compelling argument. And it's like really hard to get into. This is like if that and Beavis and Butthead had a baby, that's what this is right now. Have you ever been to Soan? It's a Soan conference, right? That's what you're talking about? No. Yeah, that's what I'm talking about. Is it online or in person?

I've always wanted to go, but it's an ordeal to go. Maybe this was your audition tape. Yeah, there you go. What do you think of it, Sean? I mean, I don't know anything about this company. I've never heard of Iren until Andrew talked about it five minutes ago. But I like the, I mean, the problem is Andrew's very persuasive. This is also the problem with me.

I can talk myself into anything. That doesn't mean it was a good idea. And I have done that to myself many times. You have to be careful. I apply basically a discount factor. It's like a charisma discount. So the more persuasive somebody is about everything, the more I have to discount to some degree. It doesn't mean I just throw it away, right? But I have to be careful not to get overly excited. And then the opposite is true in the other case. When somebody's got the David Blaine deadpan delivery of everything...

And then they're saying something that sounds exciting. I'm like, wait, if that sounds exciting coming from you, that means it must be 10 times more exciting than you're actually giving it. And there's actually like an amplifier there. So you got to be a little bit careful. This is why whenever I read Malcolm Gladwell books, I have to be like, wait, this is just a theory. This is just a theory. Like this is not a fact necessarily. That's pretty funny. What did you call that? The charisma, the what? The charisma discount. Yeah.

That's pretty awesome. Yeah, like our friend Jack Smith, whenever he tells me something, he'll be like, yeah, that's pretty cool. I think I like this. I'm like, do you love this? Yeah, I think I love it. Then I'm like, all right, I'm in. There's some people who pretty good means it's incredible. And there's other people who are like, oh, it's the fucking best. And that just means it's just another thing that they're doing. It doesn't mean anything, right? You have to like...

it's like an audio mixer has to turn some people's levels down and turn some other people's levels up on their microphone. Are you guys tracking those stock? You guys did that investment episode maybe six months ago. Yeah, TKO versus Ferrari. TKO won, I believe, Sean. I think. Yeah, it's up like 19%, I think, since we did that episode. That one did pretty well, but

I mean, it was funny that we did a stock picking episode, just stock, stock up a loser. And like, we just didn't just say the word Nvidia and then stop the recording. Cause that would have been, that would have been sufficient. And like, it was pretty obvious and in our face, but like,

when you try to be smart and make good content, that doesn't mean you're necessarily actually making the best advice. This is my fear of all YouTube doctors, by the way. And I like Huberman. I like Atiya. I like them, but also they're content creators now first. And so again, you have to apply the discount factor, which is that their job is every week to come up with new things to say. That doesn't mean that... I'm not saying they're wrong either. It's just that

The best advice might've been, you know, five minutes long said once and never, you know, and, or just repeated 15 times. Would it probably be more helpful than listening to the three hour podcast about how like, you know, getting UVB rays in your ears in the mornings is going to help you, right? Like those might not be the things that actually will help anybody at this point, but that doesn't make for good content. And so whenever somebody's primary job is content, and I say this as somebody whose primary job is content, you have to like

Remember that before you, before you, you know, get totally hooked and listen to everything that they say. This is the thing I remember in 2013 or something, I'd sold a business. I was sitting on like seven or $8 million of cash. And I was like, okay, I need to invest this. And I read this Tony Robbins book. I'm not a big Tony Robbins person, but he had that money.

I think it was called Money Mastering the Game or something. And basically the whole book is just like buy index funds. I have this disease and I think most entrepreneurs do where they say, well, that's the obvious thing. That's for the normies. I'm going to go find door number three. And I look back like,

I read chip war, which is like all about semiconductors. I knew that NVIDIA was an amazing business. TSMC was an amazing business. I saw Facebook trading at five times earnings, but it's like, I have a really hard time going through door number one. And I think going forward, I want to be more, I just want to do the thing that makes sense and is obvious and then forget about it and stop trying to be clever. This is actually an instance of me trying to be clever. Yeah.

What did you want to invest in? And then you look back and you're like, Ooh, dodged a bullet on that one. Oh, where was the obvious thing? The wrong answer. Yeah. Cause it won't be the right answer. A hundred percent of the time. Nvidia was, yeah. Nvidia, Facebook, you look back and you think I should have known better, but where was it the opposite?

I don't think I've ever really messed up on the one that's obvious, that slaps me in the face. And I don't like, I'm actually really decisive when I see that. But it's interesting. Mostly it happens for me in private businesses. I think that's where my decision making is usually the strongest because I usually do what's obvious and will work for sure. But in public markets, it's very easy to get excited. Have you had one, Sean, where you're like, I almost did this and God, I'm thankful I didn't.

Well, I've had a bunch of those, but is it specifically where it was like an obvious kind of seemed pretty straightforward, but it was a mistake? Oh, I have one. Oh, so my first designer was this guy named Adam Saint and he's the best, the best dude. Like he was one of our designers, but also like a great friend. And he went off, he left after a couple of years at metal lab and he started this company called bench. And so he comes to me and he's like, Hey, we're doing, you know, basically AI accounting 10 years early. And I'm

I loved him. I loved his co-founder. I loved the idea. But I looked at it and I was like, oh, it's a services business for accounting and low margin. And this is going to be hard. So I didn't invest.

And for the next 10 years, I felt like an idiot because over and over and over again, I'd see these big Series A, Series B. Bain Capital buys them for a huge amount of money or whatever. But it turned out that when Bain invested, I don't think they got any money off the table, nor would I as a shareholder. And I think a lot of people saw this, but he just posted a big post.

post on LinkedIn about how the business basically went to zero and shut down overnight and was a total disaster. And that's an example of one where I was like, man, I wish I so badly wanted to be part of that business and I would kick myself for years. And then in the end, I'm like really glad that I didn't invest in it.

Well, I first want to co-sign what Andrew said. I think, you know, I have meddled in the overthinking Olympics many times and I, and more than anything, the reminder is to do exactly what Andrew is saying, which is like, stop trying to be clever and just simply asking what's the obvious here. What's the obvious move here? What's the obvious answer here? And if there's not an obvious answer, just move on. Like you don't have to do anything. Uh, no action is required in most situations.

And I'm struggling to come up with a time just like Andrew, I'm struggling to come up with a time where there was a obvious thing staring at me that I did and it turned out wrong, which almost just reinforces even more how hard that is. Whereas the opposite, if you said, Hey, tell me a time where you kind of thought you got a little cute. You tried to be clever.

And it didn't work out. Your buddy texted you at 11 o'clock at night and said, hey, rounds closing tomorrow. And these 10 cool people are in and it's this really cool founder. I can't even blame anyone. It's even simpler than that. It's I was a believer in crypto early. Sam, I was talking to you about crypto early for a long time. And then one year, last year, the year before something like that, where crypto had a dip, I was like, I'm a tax loss harvest.

So clever. You know what I could do? I could sell this shit. I could buy it right back. I still own the thing. And I booked this beautiful tax loss. Oh my God, I am 900 IQ. And I just, I'm, I am the guy. And so then I sell the thing and I booked the loss and I tell my accountant, I say, don't worry about this one. I advised myself on this. I got it. And they're like, okay, great. We'll make sure we have the, that booked for the year. And I'm like, cool.

And then I'm like, I should buy back in. I was like, you know, but I did just read this report. I think it's going to go a little lower first. Let me just wait. Just let it go a little bit lower. And the stupid goddamn tax decision ended up costing what probably saved me maybe, I don't know, hundreds of thousands of dollars in taxes cost me millions of dollars in gains because I didn't just do the thing. The obvious thing was sell the thing, book the loss, buy it right back. You're exactly where you were five minutes ago with additional tax losses.

The getting cute or clever was thinking, you know, the knife still falling. Let me let it fall a little further. And then it fell a little bit further and I just patted myself and I said, I'm so smart. I knew it was going to go down. It's going to go down a little bit more. I was actually reading this article the other day and I saw this guy on Twitter who's got a picture of a fucking cartoon and, you know, he said something pretty smart. Let me just hold on for a second. Let me just wait till it goes down a little bit more.

And then it went right back up way past where I bought it. And I ended up buying in at a much higher price. I would have been better off doing nothing. It's like, you know, Ross Ulbricht was in jail and just got freed, which is, I know, a big day for you, Sam. Big day. And so... I'm trying to... I've got to shave my legs for our first date. He's walking out of prison, by the way, holding a plant, which I love. I don't know what... He's just got a small house plant that he had, I guess. I don't know what that is. But...

you know, everyone's like, oh my God, you know, I'm so glad he's free. It must've been so tough, blah, blah, blah. And then somebody goes, well, government did do him a favor because he was basically forced to not sell his Bitcoin from 2011 or whatever, when he was running, you know, Silk Road and Bitcoin was like, you know, in the dollar range to now it's a hundred thousand dollars. And it's like,

Yeah, they also did give him a gift by not letting him sell. Wait, is that so he still he owns some still? I thought that Tim Draper bought it. No, that's what they seized. Presumably, they didn't seize all of the Bitcoin that this guy had, right? Like he could have had Bitcoin in multiple wallets. He could have had personal Bitcoin. Like they seized what they got from the Silk Road. That doesn't mean they had all of his crypto wallets necessarily. You know how people say like buying a home is forced savings. He just had prison was his forced savings.

Yeah, 24-hour lockdown, forced savings, my friend. For example, I had the opportunity to invest in Coinbase, not super early, but like, let's say, series A or B, somewhere there. And I remember doing the math and being like, okay, I believe in Bitcoin. Should I invest in Coinbase, the exchange, or buy Bitcoin? And again, tried to outsmart myself. The answer should have been just do a little bit of both and let it ride. And in the end, I did this analysis that showed me that you should just own the underlying asset, Bitcoin. It's going to grow faster than this exchange, which is going to have multiple competitors, their exchanges, et cetera, et cetera.

And actually I was right. Bitcoin overperformed. But the thing I didn't factor in was that I would have made more money had I just A, done both, but B, Coinbase, you couldn't sell your shares. So like Bitcoin price went down, you couldn't panic sell. And so the forced savings of just being a Coinbase stockholder turned out to be more beneficial than being liquid with Bitcoin where you were now at the mercy of your own brain. And there's been tons of examples like this. I have a good one. I talked about this a little bit, but Metalab-

Back in 20, I guess it was 2012 or 2013, we designed Slack.

And at the time, Slack was actually a failed gaming startup. And Stuart Butterfield was basically trying to do something with the remains of it and trying to build a chat tool. And so he comes to me and he's like, hey, I've only got $80,000 budget for this. And I was like, well, we normally, you know, this would cost quite a bit more, but we really, really want to work with you. We're like big fans. And so he's like, hey, what if we did some stock?

And I'm like, no, no, no, no, no. Like, you know, we don't like metal lab would go broke if we just took stock. We don't do that, whatever. And so I said, no. And my thinking was, well, I want to get as much cash as possible so I can invest it in my own businesses. And if you think about what I was investing in at that time, it was my productivity software where I lost $10 million, right?

So I instead put it into this money losing productivity software. I could have made $100 million or something crazy because it was at like a 20 million valuation at that time. And it sold for $28 billion, I think, to Salesforce. That's a good one where it's like,

Maybe, maybe obvious. Actually, that's maybe not that obvious, but it's still, it's still a brutal one. My most recent one is Justin Mayer's True Med. He was raising for it at a, I forget what it was, reasonable valuation. Justin's my friend. I think Justin's amazing. I thought he had too much going on and I was like, no way are you going to focus on this? I pass. And he just told me how things are going. And I'm like, shit, like it was so obvious. You're a winner. I should have just said, yes, I'm in.

In my, uh, my e-com business, my, I brought in a friend into the business, gave him equity. He, he knew e-com a much better than I did. I thought, okay, my rate of learning is going to go up with this guy. And I was so excited for this like value add from this guy and his value add was like, he's super good at a bunch of things. One of the things he's really great at is marketing. So I was like, okay, he's going to be so helpful with marketing. And so we closed the deal, signed the docs and I set up the first session. I'm like, oh, I can't wait for this guy to come in and just

spill the beans on all the secrets that I don't know and make, and solve all of our marketing problems. This is going to be amazing. And he comes in and he has that first, first session. And, uh, instead of spilling the beans, he just opens up a Google doc and he's like, okay, what's the best product that you sell? And we were like, it's this one. And he's like, cool. What's the best photo of that product? We're like, what do you mean? He's like, just like, what's the best picture you have about that product? And he puts it in the Google doc and he's like, okay, if, um,

you know, like, what do people say? Like, why do people buy this? And we're like, well, I mean, the bike is great. He's like, yeah, but like, what, like, why do they buy it? Like, what do they say? And he writes down the caption and then he like goes and sets up a Facebook ad of that product with that picture, with that line of like what people say. And he's like, cool, let this run for like the next three months. And so then he, so that becomes our top performing ad. It took him five seconds and I'm like, okay, that was cool. But like, surely there's more. And so nine months go by and

And I hit him up and I'm like, dude, you're my great friend. And I was so excited for you to be in this thing. But like, honestly, I feel a little disappointed. Like, I feel like you could have done more. I feel like the expectation was you're going to do more, you know, like, and he's like, oh, I did so much. And I was like, wait, what do you mean? Like, what did you do? Like, where's the list of like, what, what do you mean? When you're saying you did so much, I'm saying you didn't do enough. What's the gap? And he was like,

Oh, I stopped you from doing all the dumb things. He's like, I didn't do extra things. He's like, remember when you got really excited about influencer marketing? I was like, oh yeah, that was awesome. I read this article and I met this guy who was crushing with influence marketing. I wanted to go all in on influencer marketing. He's like, yeah, I remember I just told you like, Hey, Facebook's working. Like keep that going. Like don't have you run into a wall with Facebook? No. All right then let's just keep doing that. Don't get distracted.

And he's like, that's what I did. He's like, the second thing, you wanted to expand your products. And like, actually, I just stopped you from doing that. And then you had this genius idea to go subscription. And I told you really like, hey, like this thing's working. So let's just keep doing the obvious thing here and just keep it going. And basically he laid out like four or five things that were all just simply like

him taking the knife out of my hand as I'm a toddler and preventing me from stabbing myself. And he was like, those were all super important moments that like this business would have gone a different way. And I was like, I don't know if you just Jedi mind tricked me into believing that you added a ton of value or, um,

You actually just said something very, very insightful to me. And I landed of, I think he's actually very, very insightful and that that is one of the best ways to help someone is to just simply prevent them from hurting themselves rather than solve their problems for them or give them some new tool that they've never seen before will solve all their problems.

Well, this is why I love investing in private markets, right? To Sam's point about houses being forced savings with a private business. There's so many of our businesses that I've owned where if I could press a red button, like a sell button, just any given day because I read something or I'm paranoid or whatever, I would have won.

way, way less wealth because I would have panicked over and over and over again. And when I look at my public market track record, I've actually had the right call over and over and over again, but then sold way too quick. Like I bought Chipotle stock when they had that health crisis, I doubled and then I just sold, right? I could have made way more money. Same with meta, all these other things. So I think that having a psychological lock-in creates, uh,

a really positive thing for people like us who are impulsive. There was a guy at the event we just threw and it was like, everybody was giving their claim to fame. It's like, okay, this guy built this thing. He's been spent 20 years building this. It's he's been grinding every day and he built this empire. And then this guy, he's building this, this empire. Jimmy's building this YouTube empire. And then this chocolate empire on top of it. And everybody's just like, go, go, go, go, go, try to figure it out. And then there was one guy there and it was like,

Yeah, he's one of the most successful investors in the world. He invested in all five of Elon's companies at the first round and didn't sell. And it was like, that's one way to do it. It's like identify the best operator in the world or one of somebody who you think is just like absolutely brilliant and obsessed. Invest in all their things. Don't try to judge rockets are going to fail, but this is going to work. Just invest in the jockey. Was it on Antonio? Yeah.

No, I can't say the name. One of the wealthier people there in a room of the wealthiest people in America, some of, and someone was like, what do you do? He goes, I'm like the CEO of my kids right now. I dedicate my life to my children. You guys work 16 hours a day on making money. I work 16 hours a day on making my kids happy and healthy and making sure they're well-loved and all this other stuff. And I was like, you're the greatest person I've ever met. Yeah, and he had that simple,

It's not the right way to describe it, but like a simpleton mindset, like the midwit thing, but like where it was like, this seems simpler. I'll go that route. Whereas many other people refuse to sit still and stay the course. What's the quote, Pascal? All of man's misery arises from an inability to sit quietly in a room. You know, this guy did not suffer from that. Guys, this is awesome. I could keep going. I just, I'm happy you're well, Andrew.

Yeah. Yeah. It's great to see you guys. I got to come back soon. That was fun. All right. Thank you. That's it. That's the pod.

Hey, everyone. A quick break. My favorite podcast guest on My First Million is Dharmesh. Dharmesh founded HubSpot. He's a billionaire. He's one of my favorite entrepreneurs on earth. And on one of our podcasts recently, he said the most valuable skill that anyone could have when it comes to making money in business is copywriting. And when I say copywriting, what I mean is writing words that get people to take action.

And I agree, by the way, I learned how to be a copywriter in my 20s. It completely changed my life. I ended up starting and selling a company for tens of millions of dollars. And copywriting was the skill that made all of that happen. And the way that I learned how to copyright is by using a technique called copywork, which is basically taking the best sales letters, and I would write it word for word. And I would make notes as to why each phrase was impactful and effective. And a lot of people have been asking me about copywork. So I decided to make a whole program for it. It's called Copy That. Copy That is...

It's only like 120 bucks. And it's a simple, fast, easy way to improve your copywriting. And so if you're interested, you need to check it out. It's called Copy That. You can check it out at copythat.com.