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Aug 26, 2026 1 hr 9 min

How a $5B founder is using AI (3 tutorials)

from My First Million Hosted by Hubspot Media

How Wade uses AI (steal his prompts): https://clickhubspot.com/efcd Episode 856: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Wade Foster ( https://x.com/wadefoster ) about how he uses AI to save himself hours of work every day. — Show Notes: (0:00) intro (2:27) The sales pitch (7:04) My Robot Executive Staff, Waking Up Like The President (14:13) Evening brief (17:39) AI that argues with you (19:32) War Council skill (31:53) How to use AI to hire better (48:15) being a billionaire before 40 (51:17) a case for not having a chip on your shoulder (54:36) 1-dimensional winners (1:00:55) recommended reading — Links: • Zapier - https://zapier.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Media Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

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How a $5B founder is using AI (3 tutorials)

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Wait, wait, Sam, you gotta click bated up. How a $5 billion founder is using AI to change his life. Well, are you a five, what are you guys worth now? Who knows? You know, you know, you, you.

You. I feel like I can rule the world. I know I can be what I want to. Put my law in it like a day zone. Let's travel.

All right, we should do a little intro. So first, is it, I've been saying, save your my whole life. Is it Zapier or Zapier? Zapier makes you happier is the trick. It's happier.

Happy, wow. Dude, how is that not your slogan? Here's what your slogan is on your site. The automation layer for a Gentic AI. It doesn't really flow the same way as Zapier makes you happier.

It doesn't. So there's two things from the name. We just couldn't afford the second P when we started. Which domain was available. But the other, like, we were too clever for our own good is it has API in the name, which we always thought like, oh, that's neat.

Because it's all connecting all the APIs and all that good stuff. I didn't even notice that. Didn't notice that. I also didn't even notice what he was missing. But also if you put Zapier makes you happier, I would have read it as, see, maybe you're happier.

Maybe you're happier. I've gone over your neck. But we're happier here. Thank you. The short story is you're the sky who's built this really cool, started off as a very simple idea.

Where you can make different apps connect with each other. What does that really mean? Let's say I have a business and people submit a form over here on my form thing. But then I kind of need that form thing. I need all the people who submitted the form.

I need that data to go over here in this other unrelated app. And you guys built those universal plugs. And you can just plug in anything to anything else. And it was just incredibly useful. Same use that I used it.

We didn't realize, all right, and realize how monstrous of a business this had become. I believe you guys are worth several billions. Maybe $5 billion was a number that I had seen at some point in time. And I think you had bootstrapped a very long way. Is it purely bootstrapped or you at some point took some money?

I think the word people call it now is seedstrapped. So we did go through YC. And we raised about a million in change. But that's all the primary capital we've ever taken. Yeah, so just incredibly to raise a million bucks and then get to $5 billion in value.

This is pretty wild. So super cool. But we are here not to necessarily tell the whole story of how Zapier makes you happier. But to show us what you do with AI. Can you give me a public sales pitch real quick?

I'm requesting a sales pitch. And what I want is I know how OG V1 of Zapier worked. We connect one app to another. You're saying, hey, we have this new AI product that you use with Claude, presumably makes your Claude or Chetubt usage more powerful, whatever. I haven't been using that.

I also, here's the other caveat. I'm kind of dumb. So imagine talking to somebody with half the IQ of yours. He's like, can you give me a pitch to someone who's sort of dumb and doesn't listen? He's smart.

At the same time. Confidence of a smart man. I have really good news for you, though. I think AI is this incredible gift of people who are kind of dumb. Because you can just agree.

Talk to it and say, hey, I didn't understand that answer. Explain it to me like I'm five. And so you can keep going down the dumbness stack for lack of a better word until you understand it. And then go, OK, now teach me back up to where I need to go. So OK, the sales pitch.

You want the sales pitch. In the old world, you know Zapier. You know, come in, build integrations, connect apps. The new world has a lot of the same things, but it's different. Nowadays, you're hanging in Claude.

You're hanging in Kodax or cursor or Open Claude or whatever it is that you like using, right? And you're just talking to it going back and forth. Most people start with that. AI is a chat pod is valuable, but it's only generally smart. It knows everything that the internet knows.

It doesn't know anything about your business. So the next step that you need to go to is to start connecting your tools. You start connecting your CRM, your help desk, your email, your team chat, all this stuff. And you feed that context in today. Now, when you start asking questions about my first million and all this other stuff, you get not just generally smart answers, you get hyper-specific answers around how your business works.

So if you install Zapier into this, you can hook up any of the tools that we have, right? So that's the first thing, the first bit of value. And the first thing that people sort of experience is like, oh, connecting stuff makes sense. But you can do native connectors and all that other stuff. So use Zapier or use a native connectors, do whatever you want.

The next layer, and where this gets really powerful, is not where you're sitting, having this back and forth conversation. It's when you're actually deploying automations and agents to actually go operate for you while you sleep. Like, that's where you start to get the real magic. And the reason you want to use Zapier to do that versus like any of these generic agent builders. What's an example?

I mean, like, Claude has routines or chat, you get stuff like, there's a bunch of these things that can kind of do agents or pseudo-agents these days. But the nice thing about Zapier is that if you use us, we are going to make it so that whatever you build is optimized to run more deterministically than agentically. And I don't think people have caught up on this yet. But you've probably experienced it. You're climbing up the IQ scale.

Hang tight. Hang tight. Agents, agents, they kind of just guess what to do, right? And if they're smart enough, they guess right most of the time. But sometimes the agents guess wrong.

And the second thing is agents are using tokens, right? We probably heard token maxing, right? And so they're really expensive. But if you use Zapier, we're going to write code for you. And we're going to write workflow logic for you, which means that it's going to run like a machine runs.

And so you're going to get, it's not going to burn tokens. It's going to be reliable and accurate. And it's only going to use AI exactly where it needs to use AI. And you've got this, you can host it on dapper.com. So you don't have to sit here and keep your laptop open to run these agents in the background.

So you just get this like rock solid infrastructure that's always been great at the hook up of everything that we've always done. But you can build a yell inside Claude, which is like really nice because Claude just kind of isn't the natural language style of building is I don't know, just way better than the no-code style stuff that we were doing in the past. Well, you're not the Wolf of Wall Street, but that was a pretty good sales pitch. I gave you the sell me this pen test, and you did a pretty good job there. So I appreciate that.

I feel like I now actually understand it. So that was good. Well, here's the magic. If you didn't, and you're just pretending and being nice, you can take the transcript of this, and you can plug it in Claude and say, wait, I think I can do it. Tell me what he was really saying.

And that's like the cool part of AI. That is cool. You gave us a list of stuff. So we said, wait, what are you making? And it doesn't always have to be like this crazy game-changing stuff, but what are you making with AI?

And you gave us a list of like three or four things. You said you have robots. You've got to click-bait it up. How a $5 billion founder is using AI to change his life. Well, are you a five-bit what are you guys worth now?

Who knows? You. I mean, you know. I don't know how the markets behave right now. They're like up and down all sorts of ways.

What would your guess be? I don't think about it. Honestly, like I'm just like, how do we build stuff that makes our number of success? I do you're a sweet guy. I didn't think you were a liar, though.

Yeah. Because I know you think about it. I guess under oath, you know. There's the old thing, right? Like in the short term, the markets are a voting machine.

In the long term, they're a weighing machine. I'd rather you just tell me F off and give me these lies. Because I know you think about it. But don't piss in my back and tell me it's rain waves. Honestly, don't tell me it's out of my business.

I'd accept it. All right. It's none of your business, right? That helps. Are revenues slightly up, way up, down, way down, since then?

The revenues are up. OK. All right. Click the headline holds. OK.

Continue on. So how you're actually using AI as a high-functioning CEO. OK. Let me share screen on some of this stuff. So we'll get into the fun bits.

One of the cool things is, because I work with my agent all the time, I can say, hey, I'm going on my first million. Help me demo this stuff. And so this is what it came up with. It's like, here's the stuff you should actually go demo. And so you can see I've got four potential things we can show.

One is the robot staff. This is kind of like my chief of staff that does a whole bunch of different automations and agents for me. I've got the CEO, CEO CRM that I built that helps me stay really close with our enterprise customers. I've got an AI that argues back. I think this is a really important thing that every leader needs to build.

I think there's a lot of CEOs out there, a lot of leaders out there that are talking to an AI that just agrees with them all the time. And so you need to, there's a few tips and tricks you can do to force it to scrutinize your thinking, rather than just tell you, yeah, you're totally right all the time. And then I've got a bunch of skills that I run for a whole bunch of random tasks internally. So yeah, I would probably start with the robot staff. I think this is cool to dig into.

The first thing, and we'll also the complete version of this, where I think most people start is kind of the morning brief. It's super simple. It's a good way to experience your first agent. You hook it up to your calendar. You hook it up to your email.

You hook it up to your meeting notes you've got, any prioritization, like a to-do list that you have. And then in this case, it runs at 6 AM in the morning, and then it sends me a Slack message. Yeah, I call this waking up like the president. Like the president wakes up, it's a daily brief. Here's what you have on your plate, 930.

You talk to this person, 10 AM, this person's here. Here's what they want to talk about. That sort of thing. And so waking up like everybody gets to wake up with the presidential briefing. Exactly.

And so these things run, in my case, I have it send me a Slack message. You can have it send you an email. I mean, you could probably have it fax you something if you really want to feel like the president. I have it set up so at Prince. But it doesn't do it all the time.

And I also have this woman named Ari conveniently, because I told her I wanted to make it come from a person in the person who made it. Is that weird for you? That same name just agent after you? The person they selected looked like Ari. So I was like, it's Ari.

So I have Ari that sends me a pump up speech as well for the day. So I love these daily briefs. There you go. Now, so the cool thing, I'll actually show you. So I have the link out to this one.

This is running on Zapier. And you can see what this actually looks like. It kind of looks like, you know, classics app here a little bit. It runs every day at 6 a.m. It goes and fetches all the calendar events.

And then here it's writing some specific code and hitting AI to write the Slack in a very particular way. Now, what is different about this is we can poke over here. This is all code, which in the past, you couldn't do this with Zapier. Now, I've not actually looked at any of this code. This is actually the first time I popped this open and even taken a look at what this is.

So you don't have to know what's going on here. But again, it kind of speaks to the value-proposed appers. It's turning all of this stuff into a deterministic workflow. And it's only using AI in the places that you really need to use AI, which means this runs way more reliably, way more consistently, and way more cost effectively than most agents. But can I use this instead?

Like, the problem that I have with Cloud or Perplexity or whatever is that my computer has to be open for a lot of these routines to run. Exactly. And it's a pain in the ass. Would doing it on Zapier just be in lieu of using Open Cloud or having a Mac Mini? There you go.

Exactly. The point. You can just deploy this as apper. And we run them in the Cloud for you. That sounds way better than using Open Cloud or having a Mac Mini.

It's way, way simpler, right? You can look up here. All right. Hold on. Just a second.

I know what you're doing. Wade, who started a company, grew to a $5 billion valuation. He's telling you all these amazing AI prompts that he uses for his business. You're probably taking a lot of notes right now. That's exactly what I was doing.

And so what we decided to do was take all of those notes, all of the scripts that he's talking about, and we put it into a really easy document. So you just copy and paste everything. So the prompts where he talks about AI arguing back with him, where he can stress test different decisions by having a seven-person AI executive committee kind of help him figure things out, and then your own life coach. So you can have a better day. So if you want this exact AI workflow, again, you just copy and paste all this stuff, just click the link in the description, or scan the QR code.

All right. Back to Wade. While it is running deterministically, if for whatever reason it breaks, say an API is down, or something doesn't work right, it falls back to having an AI try and troubleshoot for you. So it automatically apply fixes when things don't work quite the right way. And so there's this really nice blend of traditional software and agentic software here that is just super well done by the team over here.

So I definitely would say, hey, if you're struggling with your open clause, if you're keeping your laptop open all the time, you should definitely install Zapier into your agent or AI of choice and give this a try. OK. What else? So you get the morning brief. That's pretty standard.

So let's talk about, so I think the morning breach is pretty standard. But the one that I really like is the evening brief in the scribe. So I've had it. I played with a couple of versions of it. One is it runs after every meeting, and then I have another version that runs at the end of the day.

I actually think this is way better than the morning brief. And the reason why is you could actually have the AI help you do stuff. So this loops over all of my meeting notes from the day. So I'm using granola for all of my meetings. It loops over all of the to-dos that are still in my to-do list for the day.

It loops over all of the outside and emails that are in my inbox for the day. And then it prompts me and says, hey, how did the day go? So there's two key things that it does for me. One, when I say how the day went, I basically said it was a good day for this reason or it's a bad day for this reason. So now all that stuff is getting logged.

And it's learning how to tune my day to help me have more good days than bad days. The second thing that it's doing is it's actually taking action on them stuff. So it says, hey, you were in a meeting with Sam and Sean yesterday, and they asked for an intro to your buddy over at this company, do you want me to go ahead and make that intro for you? Great, please do that. So it's drafting those follow-up emails, it's drafting all these other things.

And so this is where AI starts to get really helpful, is it's not just giving you a brief and sort of teeing it up for you to do. It's now saying, I'll just do that for you. And this is where I think you start to really feel the power of AI is when you can actually put it to work. So I love scribe, those sort of post-meeting follow-up or the end of the day wrap up, because it just, I don't know. I used to spend two hours at the end of my day just like, just trying to catch up on every little tiki-tax thing that I sort of got roped into.

And now that like two hours at the end of the day is down to like 15 minutes. So you think this is legit saving you two hours a day almost? Yes, yes. And furthermore, that like, what's good about my day, what's bad about my day part? It just helps me stay focused on the things that matter.

So both the AI is helping me with that. But I also will send, like I remember about 90 days after I started doing this, I said, hey, I had this thought. I was like, you know so much about like, what makes me have good days and bad days? Can you like summarize like, what is common about my good days and what is common about my bad days? And it was like, sure, and it did all that stuff.

And then I gave it to my assistant and I said, hey, here's like, please make my days look like more good days versus bad days. What were your good days and what were your bad days? So for me, like the single most important thing is I'm a morning person. And so I do my best work in the morning. I'm most focused.

You know, once after lunch comes around, you know, I'm just not going to get anything like serious done. And so the most important thing is I don't want to meeting until 11 a.m. And so you just give me that morning time where I can knock out the most critical things and the day's going to go great. Like I will win the rest of the day. But if I have to like, you know, if that time starts to get sucked into like firefighting mode, you can tell I'll just be grumpy at the end of the day where I'm just like, like, I'm not being successful.

And you'll notice this podcast started at 11 a. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, everyone's aligned, and you realize someone still lets us down and actually create all the content? That someone is usually you and it's due tomorrow. Well, the breeze assistant from HubSpot can help.

It works right inside HubSpot. You can draft campaign, copy, blog posts, emails, all in your brand voice, all using your actual customer data. So you don't create just content, you create content that converts. Check out HubSpot.com, the agent customer platform for growing businesses. Can you show us how to get the AI to challenge you instead of a.

Oh yeah, let's do that. So coming back, AI that argues back. So this is pretty simple, right? I use, I use cursor as my daily like agent. But if you're using Cloud, if you're using Chatship D, if you're using Jim and I, they often have like a system prompt or a way that you can sort of tune like how it talks to you.

And so in cursor, I have a file that's the agent's empty. That's kind of what it uses everywhere. Cloud has a Cloud in D. And basically I have a file that's like how to work with me. And you know, I have it be direct and honest.

I need the truth. My coworkers are afraid to tell me. I need to challenge my assumptions. I need to poke holes in my thinking. I need you to disagree when you genuinely disagree.

And these things are like goal-seeking entities. And so if you tell it like what I want from you is this, it's going to say, okay, well, that's what waits one. So I'm going to try and give him that goal. But if you don't tell him this, if you don't make this configuration, it's going to just genuinely try and like placate you because it thinks that's what you want. And so you do have to tell it, you know, you sort of guide it a little bit.

So like here's an example of like, you know, a live prompt I ran ahead of time for this. I said, hey, I'm thinking we should kill our entire free tier this quarter because one of our competitor raised prices, help me draft the announcement, right? So this is like something that it should definitely like say, hey, press pause, like that's a bad idea. And so when I do that, here's the, you know, pushback that it gives me. It's like, hey, that's a big move off a pretty thin signal.

Before you draft anything, I want you to, I want three things on the table. So like, you know, bring me the data, you know, tell me like what the actual problem you're trying to solve is, you know, pricing announcements are wrong. Like, you know, is there a smaller experiment you can run? That's great. Yeah, it's just like helping you think through, you know, these problems and then you know, I have this other skill that I made, which I call my work council skill.

And so this is like an even like more specific version of this that I will often invoke. So I could say, hey, you know, I'm thinking about hiring this person. Here's all the like notes that I've got on them from the interview panel, like help me figure out if this person's going to raise the bar or not. What it will do, the work council is, this is a, actually let me put back, I think I have the work council skill in here. Yeah, here it is.

Okay, I didn't actually pull the skill up. So this, if you go to Zappars GitHub, you can get a copy of the work council. But what this does is it spins up subagents. And the subagents take on personas. There are seven subagents that get spun up.

So seven personas, some of them are standing members. So for example, I have the wartime COO is a standing member of the work council. There's the ruthless CFO is a standing member. There's a contrarian board member that are standing members of the work council. Then I leave four personas to be generated dynamically.

So based on the prompt, it will decide who else do I need to get advice from? That wartime COO, you created the persona you described its characteristics or you trained it on Travis Kalanik transcripts or something like, what did you do? In my case, it's a generic version. But you could do whatever you want, right? If you wanted to have like, Travis.

What does generic version mean though? You just said you be more high COO? I said this is a trait of a wartime COO. And it like, I said, actually what I did was said, I want a wartime COO, generate that persona. And then I looked at what it created and just made some like.

Like a pretty chill, generally happy, positive outlook. Like. Like. This is you're seeing the like, the internal competitor inside of me, right? Like this is the Kobe Bryant, Mamba mentality, like, you know, like coming through.

I like having this like, you know, this sort of thought partner that is a little bit more like ruthless because that's not my default mode, right? I want to have that kind of checks and balance there. And as a CEO, you're not always gonna have people who are comfortable, available, skilled in that way around you, right? Like this is like who you would want on your team when you want them to spin up. Quick, stupid question.

You said I use cursor for my AI. I thought cursor is a coding tool, but you're using it to chat, make decisions. Am I just wrong about what cursor is or? Yeah, I mean, cursor, you can use cursor, or clock code, code acts, like these are all ostensibly coding agents, but they have this like agent mode where you can just talk to it. And the thing is it talks to it, but because it can write code, it can do stuff for you.

And so the way, the way I try and talk to people who are not engineers and say, hey, you should try using this is don't think of it as a tool for, you know, engineers to build stuff. Think of it as like you're hiring cursor or clock code or codex to be the engineer you delegate things to. Or it's like, you probably have engineers you've worked with. You like to tell that engineer go build this for me like that's why I use cursor is because it goes and builds stuff for me, not because I'm using it to actually go build a bunch of stuff. I don't really write any code.

So your default when you just need to like talk to an AI or chat or ask a question, you go straight to cursor, you don't do just your claud or anything. I mean, mostly, especially when I'm at my desktop, I'm mostly talking to cursor most of the time. It has like different models that you can sort of toggle back and forth on, which I like. So I can test a bunch of different models and things like that. Are you a type or a talker?

I do a lot of voice to text these days. So I use this app monologue. Why monologue? I don't know, I like it. I tried a few of these.

I tried Whisperflow and Super Whisper and monologue. I don't know. It just like, it just gets me. I don't know. I don't know if a better way to describe it.

Quick side note, I think this is going to be like an interesting thing about software for the future. Like when it is so cheap to build software, I think you're going to see more software that has like a personality to it. You think about like consumer goods. It's like how many places can you buy jeans from or how many places can you get, you know, whatever from. There's like not that many differences, but you choose like you might choose one brand and I might choose a different brand.

And it's just because like I like it better, but it functionally does the same thing. I think there's going to be more software that kind of like feels that way. Yeah, I mean, I think that's a good point. It's like the Adidas and the Nike shoes do the exact same thing, but like, you know, or like t-shirt brands. Like do you remember, I was watching this like when I did documentary last night, do you guys remember Hurley?

Do you guys remember Hurley shirts? They're everywhere. And I was watching the show last night. I'm like, why do we love those shirts so much? Isn't that crazy that we got obsessed with it?

It was just that stupid logo. And why did that matter to us so much? And that's, I think that's a good point. That's how we're going to think about B2B, even B2B boring software. Well, I think it's a really fascinating point you know, as someone who plays around with a lot of the models, I'm starting to find myself have some preferences for like different tasks.

Like if I'm asking it to actually go do an engineering task or I don't need to talk to it, there's models I like that. You know, like Fable is fantastic. Like you're going to give it a really complex like, you know, engineering task. I'm like, great, have Fable go take a swing at this. It's going to nail the thing.

But man, I do not want to talk to Fable. Like it is not fun to talk to at all. We all have coworkers like that. The crush it at some tasks, but you're not just, not a great hang. Yeah, exactly.

But then there's other like models where you're like, hey, if I want to sort of like go back and forth and have like a discussion and a debate around like what we're doing, I'm like, okay, I feel like I can, you know, tolerate that discussion a lot better and like try to talk to Fable where I'm just like, oh my God. Are all the phrases like when Clyde talks to me, it's like, what are the phrases? It's like, it's not just that. Or here's the thing that's quietly really the problem. Yeah, the load bearing, you know, yeah.

Like, let's get to the spine. Are those specific to AI or to the model? To the model for sure. Like you can tell most models, I think are derivative of either the, you know, like anthropic series or GPT series. And so like, you know, those two kind of have two distinct personalities, but if you go use, you know, any of the like open source tools or things like that, you can kind of see like who they've been distilling a lot.

And like it sort of inherits the personality of, you know, the one above. Dude, I've noticed that my coworkers are starting to say, like the Claude, like someone the other day is like, let's get to the load bearing part or like something like, like when they're talking out loud and right. Yeah. Yeah. Yeah. I noticed that when they start saying things, I'm like,

that's Claude and these. And it's sort of like, yeah, like, or they're trying to talk that way. So then they can like use Claude's writing and be like, no, it's really me. Who is training who, right? Are we training the AI's or are they AI's training us?

And I think like, I think you can go a step further where, actually, let me show you this other use case. Cause this is interesting too. So this is a bunch of synthetic data. So it's not real, but you know, I have a real version of it. It's got a list of accounts and you can kind of click into the accounts and see what's going on with it.

So if we click into, you know, Acme Logistics here, you can see, you know, a bunch of stuff about it. It's like, oh, you know, you just down 34%, there's a renewal of 45 days, here's all the apps they're using, here's the people in the organization that you need to care about, et cetera. But then like, here's the interesting part. It's got the suggested CEO outreach where it's like, you should email Jordan and, you know, check it on him. See what's up?

And so this is where, you know, I think AI gets really interesting because in some respects, who's the boss now? Like am I the boss or is AI the boss? You know, every Sunday morning now, I wake up with a list of, you know, 10 customers that I want to get in touch with. And it got proposals for what I should say and what I should do and why I should do it and all that sort of stuff. And I can't really love it.

Like this is stuff that was really hard for me. Like I'm not naturally a person who's just like, you know, ultra networker like you guys are where I'm just like, I gotta keep in touch with everybody. And so now I've kind of put an agent in the loop and said, like, hey, help me be better at this stuff. And yeah, I just, I literally wake up in my Sunday morning briefing, it says, here's all the accounts you need. I've already drafted the emails in your inbox.

You just need to review them and make edits or press send. And I think there's like something to this where, you know, if you do a good job of like building these tools up, they'll kind of start telling you what to do. And you do have to keep your brain on because if you turn your brain off, you'll probably sound dumb from time to time. But by and large, I think these things make pretty good bosses for certain use cases. Well, Brian Halligan, one of the founders of HubSpot, he either came up with this idea or it was in an interview or Jack Dorsey from Twitter came up with the idea on his on Brian's podcast.

But they basically said, a lot of people are confused. They think it's going to be a human brain or a CEO in the center and then all these agents running around doing stuff. He was like, that's not the way to look at it. AI is the brain. AI is going to be the CEO.

In these humans, their job is just giving it information and then making some judgment calls if it wants to listen to the AI. But in general, the AI should actually be making the hard decisions because it's likely to do a better job. And so that kind of like changed how I thought about it. It sounds like that's sort of what you're saying without saying it that way. Well, I think so, right?

If you are able to hook up all of your company's institutional knowledge to the AI, it's going to be able to reason over way more information than a human CEO. It just can. It can look at every single commit into the code base. It can read through every single customer conversation. It can scan every comment about you on Reddit or X or LinkedIn or whatever.

So it just knows way more than you as a human is ever going to know. And so that's going to make it way more useful for certain types of decisions. To start right now, it's like you use it as an assistant to help you make these decisions. But it seems pretty plausible to me that you might start saying, hey, I'm going to take a suggestion more often than not in certain places. Yeah, I think that's what you're.

I wonder if AI is going to have like, because the upside would be AI is not going to have the emotional rollercoaster that a human would have or fears that would hold it back from doing the right thing or avoiding conflict or different things that humans have as their biases. And then I wonder if we're going to have to come up with the cognitive biases of AI to watch out for. Like, we know we have this sort of sunk cost fallacy and we have this bias for recency bias. What is AI? Because we're going to need to be aware of those the more we sort of turnover decision making to AI.

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How many decisions are you making a day that's actually weighed versus AI? Well, I would say like any high stakes decision, the AI is weighing in on now. Like, there's sort of a seat at the table and the exact meeting and the board meetings and all that sort of stuff where we're asking the AI like surface those things. Is there an example where AI kind of changed your mind or got to the right answer that you weren't at and you decided to go with it? Here's an example of a place where I find AI to be really useful.

Let's go back to the hiring example. So we run a par-raiser process where I approve every job offer that goes off, but like exact team members sort of is on the final part of the hiring loop and it's intended to audit the hiring process in addition to sort of figuring out, hey, is this person going to elevate the culture, the work, et cetera here, et cetera. Now, in the past pre-AI, when I would go through those approvals, I would often, you know, if I would come across a candidate where I was not so sure on, I could kind of smell something is wrong. I've just done enough interviews now. I've interviewed thousands of people.

I've looked over thousands of applications where I just have more reps than most hiring managers have. Like most hiring managers hire one or two people in a year. It's like, I'm just looped over like way, way more volume. And so I don't always have the language to say like, why it's wrong, but I can still smell it. And so I would often go to these folks and be like, are you sure something is off?

Like I don't think they have this or that. And it was interesting that interaction with my staff was always a little bit fraught. Like folks would be like, well, I stand by this person, like wait, are you just going to make the hiring decision? If so, like you just, if you don't want to hire them, don't hire them. And it sort of would be like, well, that's not really what I want, right?

Like I want you to make the decision. I'm just trying to like give you some guidance here. And I want you to sort of be able to, you know, reason through this problem. And if you've answered it, like if you have confidence that you have, you know, officially answered it, then I would back to you. Let's go hire this person.

But if you haven't, then I want you to like, take this into account and go figure out like, you know, is there more information you need to get or do you need to adjust your course, et cetera. But that's not often how it would play out. It would just sort of play out as like, well, does Wade want me to hire this person or does Wade not want me to hire them? And I'm like, ah, like, no. So anyway, that's kind of what was happening pre-AI.

Post-AI, I'd run the work council or like my hiring committee over these folks. And then I would notice like, it's just more articulate than me. It could sort of say, hey, I noticed that, you know, this person has these traits and the panel did not scrutinize this. So you need to go scrutinize this. And it would, you know, it would give like a score of like, here, compared to everyone you fired is happier.

Here's how, here's how likely I think they're going to be successful or not. And so now I could take that to the hiring panel and say like, hey, the AI said this, I agree. Like what's going on here? And I noticed all of a sudden the behavior shift where people would go like, oh, interesting. I think that AI did get this and this right.

But I think it's wrong on this. And here's why, because I have this other context that it doesn't have. And I'm like, great, that's all I was wanting to know. And maybe because it's not, maybe because it feels like arguing with an AI is easier than arguing with the CEO. Or maybe because it's more eloquent.

And it like actually has a way of talking that makes it like easier to address the specific points. I'm not exactly sure. But I did notice the way we made decisions around hiring got better in part because we added the AI to the look. I don't know if you guys were ever like believers in some of these personality tests. Like there's this thing called culture amp.

I think it's called where it's like a software where you do personality test before you hire someone. Radalia has his version of it, whatever. And there's like tends to be, it's like a scale people fall in where they're like, I don't believe in anything involving like personality tests. And notice with AI, I've fallen closer to the side of like I follow what it says because I've done somebody's personality test and I've used it to train my AI and it's helped me a lot. But when it comes to hiring, do you guys buy into this at all?

When it comes to personality tests and like figuring out if a person could get for the job because that makes, with AI, it makes the process so much easier. What do you think, Sean? I go the other way, meaning it's not really about personality tests per se, but I find that, you know, like with self driving, one approach was let's put all the sensors on the car, let's get cameras, let's get more cameras, let's get LiDAR, let's get radar, let's get some on R, let's give you know, what else do we do? And the test load approach was basically like, it needs vision, it needs eyes only. And one of the reasons why people thought it was for cost, which was I think a factor that LiDAR was very, very expensive, so it's not practical in the long term.

But the reason that Elon says that he did it was because when you have too many sensors, you get too much conflicting data and you don't know which one to trust, it makes it more faulty, more error prone. And actually what you should do is take only the minimum number of sensors needed but then train the hell out of them. That's kind of my approach to hiring, where I now simplify, I need less time to spend with somebody and I look for fewer things and but those have to be home runs, otherwise I'm just not going to hire the person. So what do you do? Yeah, yeah, answer the question though, like how do you, okay, what you're saying is instead of looking at like hundreds of questions, you're looking at three questions.

Are you good at this? Okay, so how do you gather that information? So again, it's doing for me, Lon, he talks about evidence of exceptional ability. So all I'm looking for, I'm not looking for like, the first filter is just evidence of exceptional ability. So I'm not trying to assess culture fit right now, I'm not asking, do I like them, I'm not asking like, do they have the relevant experience?

All I want to know is have you done some exceptional shit before and then tell me that story and in that story, I'm going to try to understand, did you do it or were you on a team of people doing it or were you writing somebody else's co-tales doing that thing? And if you really haven't done anything exceptional, the odds of this being the place where you have the final, you know, the first exceptional thing of your career is not really a bet I'm excited to go take. And so that's the very first filter that I'm looking for and that's not personality test driven. Then after that is a kind of personality test of like, do I try to do something with them where I get the, you know, gut feel of like, do we have creative chemistry? Do I feel like this person is good to have in the room when I'm trying to figure something out or do I feel like they're not not elevating that conversation when that happens?

And so I'm really just kind of like a two step filter and that's it and that's all I want to signal. But obviously like I'm not running the size of Oregon. It is and I'm using, I'm working with people working directly with me in a very, very small team where everybody has to be, you know, 10x or better. Otherwise it's just not worth having them on the team. And so that's the, I've learned that kind of the hard way because I used to do it very differently.

Yeah. We, so we've done some work with this. So like we've done like Myers Briggs type stuff internally at times. We've done, there's one called Berkman that we've done at times. I have found it to be moderately useful.

I have a CEO buddy who runs his public company in Colombia that does dis profiles for every hire and he's like, it's like, I have an accountant, they need to be this profile and stuff. It's like, if they're not, they're not going to be a good fit on the team. I'm not gone that far. I think what I, where I net out is that, I mean, you do need somebody who is exceptional first and foremost. Like everybody's got a personality type, but it doesn't tell you if you're good or not.

Like, you know, you can score whatever you're going to score, but you still need to be good. Yeah. But I do think that like teams matter. Like, and when I look at my, my personality or my way of working, there are things where I am exceptionally good at and there are certain defaults that I have where I know that if I am partnered up with somebody who has like a complimentary trades, I'm going to be way better because they're going to have my backside in places that I don't know if like there's any science behind this. But if you look at my EA versus my, like Myers-Riggs, she has three different letters than I do.

So there's four letters in that and three of them hers are different. And she does like have, she likes doing things that I don't like doing. And she's good at those things that I don't like doing. And it ends up being like pretty helpful because it gets kind of like in sports where it's like, you know, you basketball team, it's like, well, you need somebody that's going to, you know, Michael Jordan's going to shoot all the shots. Well, you need Dennis Rodman who's going to like lock down D and grab boards.

What are you doing that when you guys are hiring? We don't do it. And so I'm like, I'm going to have people like take a test and say like, Hey, what are you going to do? Different hiring managers are probably doing it somewhat like by like organically, but it is not a science for us. I have an idea for how I think companies could use AI to improve their hiring.

I don't know if this is like legal. I don't know if you could do this exactly the way I'm going to describe it, but here's the exercise. I mean, you go through your team. So you have all the past hires you've made the last let's call it three years. And you could stack rank who's exceptional, who's acceptable and who's kind of like been a source of kind of hit or miss performance, I'll say.

Cool. You also have maybe the transcript of the recordings of all the interviews that they did, right? So you have this historical pattern that you have with all of them. And then you have new people that are coming in and like, so when I was at Twitch, they use the Amazon bar raiser thing that you described and they're trying to do like the human version of this. It's like, here's this guy who's seen a thousand interview panels who will come in and kind of like standardize the hiring process, but also like provide the most experienced voice on hiring.

And then they're kind of checking this candidate against this pattern of past candidates as well as against your values and you know the role, the role in mind. And I just think AI is going to be way better at that. I think it's going to be like dramatically better at that. And I'm surprised that people aren't using like kind of the training data of your existing team to inform the next hire. Do you think it would work?

Like I don't know for sure if I would be good at that, but I kind of think that would be helpful. I mean, I remember Google sharing like a lot of their hiring insights where they did a ton of tests around this stuff like this. And I think what they found was that no hiring managers were like, had an edge over any other hiring managers with one exception. And the one exception was that there was like this hyper specific specialized group of like technical where there was like only like an end of like 100 people in that domain. And it's just like their hit rate was better because it was like, well, there's just only 100 people to do this thing.

And so I don't find that a very satisfying answer. Like it feels like there should be something to what you were saying. Also something that I've been thinking about a bunch like I was thinking a large percentage of the people who work at my company, which is like 35 or something. They we work here in this office out here and they're here because basically I'm bored and I want someone to hang out with most days. Like that's like probably somebody for the reasons why I have a company just because I want someone to hang out with.

Because I'm not good at friends. Yeah, like I'm like I'm like hard employees are here at the heart starting LLCs is easier. Which sounds like a joke, but like I'm sure Sean you agree. Sean has a guy who works with him. He's like you can work for me if you move here and we hang out every day.

Yesterday I was like I'm kind of done working. I'm just like four night before night for a couple hours. I need a pickleball partner. Can you come be my employee? I mean that's kind of how it is.

I just want like a lot of people. But when you have, okay, now I want you to put like let's be the CEO war console and I need you to be like crazy Wade, not real Wade. So anything said for the rest of the section you can be you can kind of go on hinge. Unhinged mode. Okay.

Yeah, but we're always yeah. I don't know how many employees you have now, but you used to have 700. No. It's like seven, 30 or something like that. So when you have like remote employees like for the most part you only know them as just like slack avatars right like you don't know all 700 people and many of you then don't know you other than like this guy on zoom and someone who blogs occasionally.

It kind of like begs the question like what if they were all just like or like him like one person just be like 10 or 30 different agents that they monitor and you only have like 20 employees. I think that there's definitely a school of thought where I've heard that. I do think there's limits to this. And the way I think about the limits is that it's kind of like how a manager has like an ideal span of control where it's like I can only have like you know, I don't know the rule books as eight. I think you know you're seeing people push the limits now to have like you know 10 or 12 or if you're Jensen you've got 60 or whatever.

But there's still a limit where it's just like I just cognitively cannot like keep up with like this many people. But you don't keep up with that many people anyway like when you have a company like there's stuff happening that you don't even know about why wouldn't you just have it be one of your agents. Well, so you could but the thing is you're only going to be able to keep up with what 20 agents because it's going to keep us on you tasks and more things to do and more things to do. More things to do is like a there still is like a limit. But I'm not saying that it would be like just weighed but I'm saying like do you think that there's a world where let's just say that hypothetically you guys do close to half a billion in revenue.

Is there a world where like 20 people could do that? For company like Zappier I'm not sure but definitely like a company could certainly do that. In fact we've already seen companies that are gotten to like that size on very small numbers of revenue. Which ones? Well I mean shoot like Minecraft back and before Microsoft bought it was like I don't know how many people but it was like less than 100 I think and it made it you know a whole bunch of money.

There was that New York Times story that came out this summer about that guy who was selling like GLP one stuff. Yeah we had them both as a guest on the podcast and that article came up the day before and he canceled on us. Well so yeah like he's doing like I don't know how many employees he has but I think it was like maybe one or two. Yeah how many inmates does he have now? Two inmates?

Yeah how many cell mazes do you have? But I mean you also could think of someone like Taylor Swift like Taylor Swift has a very small team from what I understand and is you know printing you know billions a year or something like that or at least that her peak was. So I know I think it just kind of depends on this. Maybe just the philosophical thing of like do you think that the way so the way work worked before was you start off as an individual contributor and then you can become a manager where you manage a fleet of individual contributors. Yeah.

And maybe in the corporate world your value was proportional to how good you were at managing people. Yeah. Is the new world where your value the thing you get the amount you get paid is based on how well you manage AI agents right like how big of a fleet can you manage and how effective is that fleet is that the new managerial skill. Yes I feel pretty confident that that is the direction we're heading to. Sort of saying I mean I don't want to put words in your mouth but you just had the same thing.

We got there. We got there. And again this is a realist way so you don't want you to like think that you have to like hedge or apologize but. There's still different roles in a company right like you know you're think of like your sales team. Like I still think that for certain purchase categories we still want to talk to a human we still want to buy from a human.

Do you want your sales reps everyday waking up and managing fleets of agents or do you want them talking to your customers and helping build those relationships and close out trust and all that. For that role I think I kind of want you to build in the human relationship more so than like doing a bunch of AI stuff. I definitely want you to do some AI stuff but it's not necessarily like hey you know Mr. Miss like sales leader or like frontline sales like go manage these 20 reps that are going to actually do the sales for you. Can I switch gears for a second?

How old are you? I turned 40 this year. Okay so you were if $5 billion is your value you were in the ballpark of being a under 40 billionaire. Give or take. Does that feel strange because you seem like a guy who does not particularly even though I was teasing you you seem like a guy who doesn't particularly care about money or success other than have a good time.

I mean it feels honestly it feels a little fictional to even here you say that or I'm like I don't think of myself like that way. It sort of is like so much is like tied to like the paper worth of zap or any given moment in time. It's like the voting machine. Like I don't have liquid dollars that look like that. You know I have some amount that's liquid.

Describe your psychology around money. So how do you think about it? How do you use it in a way that improves the quality of your life? How do you avoid it so that it doesn't mess up certain parts of your life? Make us a little smarter just share your perspective.

Yeah I think look it's a lot of this stuff is like highly personal and like what do you care about in life. And for me then like things one two and three are my family. And so I want to be around my family have like you know provide for them. You know make sure that they sort of are able to sort of live a good life by whatever definition I have of that. And truthfully like once you get to like a certain amount of wealth like more wealth doesn't change that equation.

What do you think that level is? I mean she would come live in Central Missouri it's not that much. Yeah I think you could do just fine with like a million bucks and you know do quite well. I mean she when I was I remember when I just got out of college my dream was if I could only make a hundred thousand dollars a year. That was my dream is like if I could make a hundred thousand dollars a year I was like man I'll be set.

I was mine too by the way it was it was like if I can get out and work at KPMG and get 60 grand I can make it to a hundred grand from 30 and then I am set baby. Yeah that was the goal. And I don't know like partly that's you know I don't have like a lot of vices I don't have like a lot of expensive hobbies and things like that. Do you do anything cool with your money? You know when I go to a restaurant I don't look at the how much the items cost.

Nice. And so you've raised money so you have to have some type of likely presumably you're going to you want to have some type of exit event whether that's IPO or selling the whole thing. Is there anything that you have on your bucket list that you'd want to like if you're like okay if I get over a billion dollars liquid I want to change this about my life or there's something interesting I want to do. No there's like nothing that I couldn't already do. You know like I remember my grandpa like his dream was always going to Safari and he never got to go on one.

I always thought like that was an incredible thing and so when my girls are old enough I'm like let's go on Safari. But I do that now I don't need billions of dollars to go on. The reason I like asking you about this stuff is because you are very well rounded and you seem like we had this like joke called like the total man it was like a buddy of ours or a podcast guest who was like kind of like the perfect package like they were like ruthless when they need to be ruthless they were sweet when they need to be smart but they were still a good hang and they were like I feel a good hang and like I said like Darmesh has that and you definitely have that too. So I like hearing your opinion on topics where most of the people are selves or myself included talk about it from up their broken they have a chip in their shoulder perspective whereas I don't think you have that you have a far more wholesome and positive outlook when it comes to the stuff.

That's why I like hearing you talk about some things where you don't typically peer an emotionally healthy person give their perspective on. I was really lucky like I grew up you know with a family that was all sort of like you know like my parents were married my two grandparents that were married I have like aunts and uncles and cousins that were all sorts of like really tight knit. But if I was like give a shout out to any of those like I got to talk about my granddad like you know my granddad's World War Two Vet but you know I didn't know him as that I just knew him as this guy you know who like always had time for his grandkids he died his 98 and half and he basically lived by himself the entire time I knew him he drove himself up until two weeks before he died he walked three miles a day every single day until two weeks before he died he did the New York Times crossword puzzle in Penn every single day and I remember going to you know after he died we were at the funeral home and they were trying to like playing out all this stuff you know most 98 year olds when they died it's like they don't got any friends there's nobody going to be there because everybody who's everybody who would have been there has already died.

You're 98 like they just he just made it a long time and I remember the staff saying like okay like you know we'll probably just do like a reset you know the receiving line or whatever will be you know like we'll just do like 30 minutes or an hour or whatnot and that receiving line is there for three hours people just like coming through non-stop and you know just members from every single walk of life like he had you know when he was a teacher he had all these teachers that were coming through that remembered him he was like big with the dare program so like all these I would patrol me coming through all these members of the church coming through all his extended family coming through and I remember that like standing out a lot to me where it was like here's a guy who you know was was great. And family and great at professional stuff and I just that's a me was like just a really good example of you know someone who got their like priorities that like like dialed in really really well.

We didn't have it all but he needed all it's like the things he cared about he nailed them and so to me that's always like stood out is like what what a good life looks like. Sounds like a good role model I think that you definitely seem to embody that we're like like I said you are great a business and also like don't have this jackass side that most people who are where you are seem to have. Right Sean? Yeah we first I love that story that you just told I was actually a really awesome and awesome story and also you know I think that the value of what you just said you said two things that you said he didn't have it all but he didn't need it all. And I think you know I've been thinking about this a lot lately which is that you're really only as as rich as what you don't need you know basically like if you don't that's whether that's material things are other right if you don't need the approval or attention of others.

You're free you're rich you know because you just don't need that it's not one of the things that you have to go pay the cost to go get. You don't have to go be super flash on social media because you just don't care for it. And so I think that's like such an underrated attribute and when you said that it kind of reminds me it sounds like you're going to have to have that kind of that way of life. And the other was you know they're defining what winning is so like if winning is just in the work domain or winning is just in one you know just in one of it you have to kind of decide what it is for you. And it sounds like pretty early on you got clear on that and the clearer you are the less likely you are to be blown around with the wind you know the media portrays Jeff Bezos or Elon Musk or whoever has like the Titans and then you say oh I guess that's what winning is and then you're you know soon enough on your you know multiple divorces and your kids whatever whatever you can go it's easy to go down a certain path if you didn't have like a really grounded belief system around what winning is and have examples of people who've won that way because you'll get a lot of examples of what I call one dimensional winners.

Michael Jordan the ultimate I'm a basketball fan so I grew up being like Jordan is the go he's the greatest he's the best and he is when he comes to basketball but he also had many things in spursalance I don't want to emulate so as much as I wanted to be like Mike on the court I did not want to be like Mike off the court I think it's worth the time to do what it sounds like you've done which is kind of like find find whatever that north stories for you so that you kind of have a clear picture in your head. It makes all future decisions really easy going I love that like you know define your own definition of winning and if you do that well like some of your decisions might look odd to others. They'll be like why are you doing that that way you could do this you could do that the other but you'll be a lot happier when you're just like this is what I want to be doing and you know what you want to be doing is you know running us off for company and you'll great go do that if you want to do is.

You know be a teacher you know help students do that like if what you want to do is. You know I don't know live on the coast or live on the coast like what is it that sort of a is winning for you do you have an examples of that I mean you are very successful you moved from San Francisco back to Jeff cities so that's like an obvious one but like are there any other like strange zapier or. Wade decisions that you've made that you think that the normal Silicon Valley guy would be like that's insane I mean like. I mean the sort of remote work story is one where we've just never had an office wait before anyone thought that was normal yeah we only raised the one round of money like that was like pretty odd at the time like you know we're building this business for like the long haul. And so I got constantly good question like what about I mean tech you guys are asking me about like what about the extra what's the valuation what's it and I'm like it'll be what it will be like we're here to grow it for customers like that's the thing I care about.

Not these other things and you know I think we do a good job of that then sure the numbers will follow but that's not the point like the point is like the work itself. I think that's you find that with anyone who loves what they do you ask them this is where I feel like the media gets a lot of this like narrative around billionaires wrong is there like you know they're holding money there's all this stuff. I mean look I don't know what billionaires I've gotten to meet a couple and you know Darmesh how you like you know guys like this who I don't think genuinely just seem like they like what they're doing and like they're going to keep doing that whether or not they make you know a little bit of money or a lot of money. The test has played out they did it before they were making any money and kept going when there was no clear line aside to money.

When they made the money they kept doing it. It's like it's really wasn't about the money because I just like doing it I think it's the same way like you look at like Olympic athletes. Olympic athletes make a lot of money but they just love doing it and they're just going to keep doing it no matter what you see it in you know professional sports where like guys are you know at the tail end of their career and they probably should be retiring but they keep playing because they just love playing and they'll take the lesser contract they'll do all this other stuff because it's like I just can't I just love this game like I love doing that thing. So Sean listen to this one time I think in 2000 and maybe 2019 Wade spoke at House of Khan in Oakland California and this was right I think before you raised your round.

I think but you guys were the hottest thing going and you came and talked and I thought it was awesome and I don't know if you remember this Wade but you and I sat backstage for like 10 hours and all the speakers would come and go and they would have to pass to this room and I think I don't know exactly if this is how you felt. I think you did the same thing I wanted to do which is like these people would come in and we would just stare and like observe how they were behaving because it was kind of fun to have like billionaires or like these big shot CEOs just like interacting with you having a normal conversation. It was really exciting it was like people watching on steroids and we're just we're kind of staring at them but I remember you sat with me I don't know if you remember this for like it was like eight or 10 hours. It's like the entire day and I was like you got somewhere to be and you're like nope I just like being here and I remember that you doing that and it seems like you have a change where it was like you were very successful then now you're incredibly successful but it was a very similar personality where you're still very curious.

Yeah I don't remember being eight or ten hours but I do remember all day like you got at nine I think we left at four so I was yeah. Yeah I mean you got to pull the good guests man like who would want to just like sit backstage and like listen to how all these people are running their companies and what's working for them and what's not I mean shoot I'm almost certain I had a book of ideas I sort of took back and was like you're taking this. Yeah I mean the awesome thing is like you know back when you were doing that like I feel like podcasts weren't quite as big a video but now like God you can just like pour over the stuff and you just have like notes for days on things that you can just go try. See if this works for me. What do you listen to and what do you consume on a regular basis book well my my favorite podcast whatever my favorite podcast I got to give a shout out to the acquired guys like I mean this just 10 out of 10 like you know most of those things they do a deep dive on are just these legendary entrepreneurs who have like you know did it for decades.

Give us a acquired episode we should listen to and maybe a book that you liked. Well then I fell episode if you like sports at all like you know that is a good entryway into acquired the probably my favorite series is all the retail ones so there's like a. Like I think it's Costco Walmart and Amazon and there's a right in there that are like all really really good as for a book. I recently finished this book make something wonderful it's a Steve Jobs like in his own words it's a really good one. Yeah I think Steve Jobs he sort of has like a larger than life reputation this book is literally just emails speeches literally just like his own his own thinking and it's sort of organized roughly chron chronologically and so you get to kind of just see his progression of like you know V one apple the Pixar years V two apple and you kind of just see how he changes sort of like over time.

You want to recommend. Yeah there's a book called the score. Have I talked about that here. See Ty when is the guy's name on the cover. It's called the score how to stop playing somebody else's game and this is a guy who the fundamental premise of the book is amazing he's talking about like the power of a game so he's like imagine a game.

Let's say we take a picture. We open up a game a picture and games are this incredible thing because they tell you what winning means so they tell you the rules what you're allowed to do they tell you the scoreboard so like how you game how you win in this game and like what your goal should be. So they dictate your goals they dictate your behavior and then they also sort of dictate who you need to be to be good at this game and he's like let's take a game like charades to be great at charades you're going to have to be loose you're going to be highly communicative you're going to be a great team player whether you're the the gesser or you're the actor doesn't matter but then let's say you play risk it's like you're going to have to be like ruthless dominating you're going to answer like it's amazing if you just take the idea of a game how it will change your behavior and he's like basically extends that to like the game's life and so he describes like when he was a professor he's like I got into teaching philosophy because I love philosophy that of course that's why who else becomes a philosopher he's like but then I discovered this leaderboard and it was like all the philosophy professors in the country and he's like suddenly I started well how do you get on that board right now I want to be not on the board and so you can kind of instantly is like oh you got to get published and he's like well then I realized like the way they get published the most in the fastest in these obscure publications about these types of things he's like suddenly a few years in I hate what I'm doing he's like why am I'm doing this like I'm doing studies about shit that I don't even care about to get published again on a leaderboard that doesn't matter why because I play games we all play games and so you have to be really careful about like games and the different types of ways you play and there's like.

Striving play which is like you play for the joy of playing versus like outcome based we're playing to win and like you know you want to be a striver for these reasons and that the strivers actually tend to win more too but they didn't play for that reason and like you can't just say well I'm not going to play any game because like it's no fun let's say we're playing charades and if you don't care at all about winning we're not going to have a good time like the trick is to care about it in the moment and then completely let it go afterwards and when you remember that oh the reason we're playing straight is so that we can have a fun time as a group hanging out not so that I got the most points in the game and so you know it's all this like nuance around the games and I think like because I think the biggest decision you make in life is what game you're deciding to play and how that will shape the next 10 years. Came out to the book came out like six months ago. Yes I'm taking that book right now I just finished I'll wrap up with this one way you might like this one I think you if I had a guess you listen to 22 that's good.

I did. Did you Sean. I mean who didn't. Yeah. I read the biography of the memoir of Mark Hoppis who is one of the lead singers of like 182 such a good book I read it in three days I couldn't put it down it was one of these books where like I had a force myself to put it down when I was going to bed at night because I was like staying up too late.

Why are musicians biographies so good. There's a lot of the more is whatever musicians and comedians. What else do you have. This is the hot chili peppers guy Anthony Gidis was that good long time ago I was in college I read this thing I loved it. This is his is good I think because he had a messed up any part of the rest of childhood.

So it's like riveting these guys they weren't really that messed up but they got really famous like really fast and he talks about it and he's like you know a lot of this is the way the chapter where I complain about fame and he's like just joking I love being famous. It was awesome. Like people go to me all the time they say they love my work it feels amazing and then you also later in life he got cancer he talks about like his cancer treatment. Oh such a good book if you guys want some fun read Mark Hopper's autobiography and if you want like. What's called.

Fair and height 182 I believe but anyway wait you're the man we appreciate you you have an invite whenever you want and thank you for everything. You bet thanks for having me guys. All right that's it that's a pod. All right let's take a quick break I want to tell you about marketing school is a podcast that's part of the HubSpot podcast network and it is run by Neil Patel and Eric Sue and these guys are both marketers who are running businesses and so if you want real world tactics from practitioners who are actually out there in the field doing it this is the podcast for you check it out. Wherever you get your podcast.

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This episode was published on August 26, 2026.

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