My First Million - How a $5B founder is using AI (3 tutorials)

Episode Date: August 26, 2026

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 /

Wait, wait, Sam, 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-b... What are you guys worth now? Who knows? You know. You know. You.

I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel. Never left. All right. So, first, do you, is it? I've been saying Zapier my whole life.

Is it Zapier or Zapier? Zapier makes you happier is the trick. It rhymes with happier. Happy, wow. Dude, how is that not your slogan? Here's what your slogan is on your site. The automation layer for Agentic 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. One, we just couldn't afford the second P when we started. 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 these APIs and all that good stuff. I didn't even notice that.

Didn't notice that. Yeah. Honestly, didn't even notice the pee was missing. But also, if you put Zapier makes you happier, I would have read it as Sabier makes you happier. It's got it on with your day. But we're happier here. Thank you. The short story is you're this guy 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 like universal plugs and you can just plug in anything to anything else. And it was just incredibly useful. Sam used it. I used it. We didn't realize or I didn't 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 at some point took some money? I think the word people call it now is seed strap. 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 is just pretty wild. So super cool.

But you're here not to necessarily tell the whole story of how Zapier makes you happier. but to show us what you're doing 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 OGV1 of Zapier worked, where you connect one app to another. You're saying, hey, we have this new AI product that you use with Claude,

presumably makes your cloud or chat GPT usage more powerful, whatever. I haven't been using that. I also, here's the other caveat, I'm kind of dumb. So like 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? But things are smart at the same time. The confidence of a smart man. I have really good news for you, though.

I think AI is this incredible gift to people who are kind of dumb. Because you can just talk to it and say like, hey, I didn't understand that answer. Explain it to me like I'm five. And so you can keep like going down the dumbness stack, I guess. as for lack of a better word, until you understand it, and then go, okay, now like teach me back up to where I need to go. So, okay, the sales pitch, you want the sales pitch.

In the old world, you know, Zappir, 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 clawed. You're hanging in, you know, codex or cursor or, you know, open claw 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 as a chat pot 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 to the AI. 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. Okay? 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 look, you can do native connectors and all that other stuff. So, you know, use Zapier or use the native connectors, do whatever you want. The next layer, and where this gets really powerful, is not where you're sitting having this,

like, back-and-forth conversation. it's when you're actually deploying automations and agents to actually go operate for you while you sleep. That's where you start to get the real magic. And the reason you want to use Zapier to do that versus any of these generic agent builders. What's an example?

I mean, like, you know, Claude has routines or ChatGPT has scheduled stuff. Like, you know, 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. Climbing up the IQ scale. I know, I know, hang tight, 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 Zapier.com, so you don't have to sit here and keep your laptop open to run these agents in the background. And so you just get this like, rock solid infrastructure that Zapier has always been great at and hookup of everything that we've always done.

But you can build inside Claude, which is like really nice because Claude just kind of, the natural language style of building is, I don't know, it's just like 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 to 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, and 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 a claw out and say, Wade said this thing.

Tell me what this guy was talking about. 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, Wade, what do you make him? And it doesn't always have to be like this like crazy, like 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 staff. You got to clickbait it up. How a $5 billion founder is using AI to change his life. Well, are you a five billion? What are you guys worth now? Who knows? You.

I mean, you do. I don't know how the markets behave right now. They're like up and down all sorts of ways. What would you a guest be? I don't think about it, honestly. I'm just like, how do we build stuff that makes our customer successful? Wait, I knew you were a sweet guy. I didn't think you were a liar, though.

Yeah. Because I know you think about it. We're doing this podcast under oath. You know what, right? There's the old saying, right? Like, in the short term, the markets are a voting machine and the long term, they're a weighing machine. I'd rather you just tell me F off than give me these lies because I know you think about it. But don't, don't piss on my back and tell me it's rain, Wade.

I honestly don't. Just tell me it instead of my business and I'd accept it. All right. It's none of your business, right? Okay. That's fair. Since the last time you guys got value. Where did the $5 billion number come from in the first place?

That was a secondary number sale that happened in 2021, maybe? Okay. Are revenues slightly up, way up, down, way down since then? Revenues are up, yeah. Okay, all right, good, so we're doing well. All right, the clickbait headline holds. Okay, continue on. So how you're actually using AI as a high-functioning CEO.

Okay. Let me share screen on some of this stuff. So we'll get into the fun bits. One of the cool things is, you know, because I work with my agent all the time, I can say, hey, I'm, you know, going on my first million. Like, help me, 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, you know, four potential things we can show off. One is the robot staff. This is kind of like my chief of staff that does like a whole bunch of different automations and agents for me. I've got the 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, like, there's a few tips and tricks you can do to, like, force it to, like, 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 like cool to dig into. The first thing, and we'll, we'll show the complete version of this. Where I think most people start is kind of the morning brief. You know, it's super simple. It's a good, it's a good way to experience like your first agent. You know, you hook it up to your calendar. You hook it up to your email. You hook it up to your email. You'll look it up to your, you know, any meeting, like notes you've got, any prioritization, like a to-do list that you have. And then, you know, in this case, it runs at 6 a.m. 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 gets a daily brief. Here's what, sir, here's what you have on your plate today. 9.30, you're talking to this person. 10 a.m. this person's here. Here's what they want to talk about. That sort of thing.

And so waking up like every, now everybody gets to wake up with a presidential briefing. Exactly. And so, you know, these things, like, in my case, I have it send me a Slack message. You can have it send you an email. I mean, heck, you could probably have it fax you something if you really want to feel like the president. I have it set up so it prints. But it doesn't do it all the time. And I also have this woman named Ari conveniently because I told, I wanted to make it come from like a person and the person they made.

Is that weird for you that Sam named his agent after you? The person they selected looked like Ari. So I was like, it's Ari. So I have Ari that sends me like a pump-up speech as well for the day. So I love these daily briefings. There you go. Now, so the cool thing, I'll actually show you. So I have the link out to this one.

This is, you know, this is running on Zapier. And you can see what this actually looks like. You know, it kind of looks like, you know, classic Zapier a little bit. You know, 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 the AI to like write to 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, like, you couldn't do this with Zapier.

Now, I've not actually looked at any of this code. Like, this is actually the first time I popped this open and even taking 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 prop of Zapier's. 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? The problem that I have with Claude 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 like in lieu of using like OpenClaar or having a Mac Mini? There you go. Exactly the point. You can just deploy these Zapper and we run them in the cloud for you. That sounds way better than using OpenClaw or having.

a Mac Mini. It's way, way simpler, right? You can look up here. It's also agent managed. So one of the nice things is... 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 them 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 can 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, like say an API is down or, you know, something doesn't work right, it. falls back to having an AI trying troubleshoot for you. And so it automatically apply fixes when things don't work quite the

right way. And so there's this really nice blend of like traditional software and like 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 installs Zapier into like your agent or AI of choice and give this a try. Okay, what else? So you get the morning brief. That's pretty standard, I would say.

So let's talk about, so I think the morning brief is pretty standard. But the one that I really like is the evening brief and the scribe. So, you know, I've had, I played with a couple 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 can actually have the AI help you do stuff. So, you know, 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 outstanding 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 is 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. But the second thing that it's doing is it's actually taking action on stuff on stuff. So it says, hey, you know, 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. Right. So it's drafting those follow-up emails. It's drafting. all this 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, the sort of like post-meeting follow-up or the end of the day wrap-up because it just, I don't know, I used to spend like two hours at the end of my day just like, you know, just trying to catch up on every little tic-tack 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, you know, what's good about my day, what's bad about my day part? It just helps me stay like focused on the things that matter. So both the AI is helping me with that.

But I also will send like I remember 90, like 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 a 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, ugh, like I'm not, I'm not being successful. And you'll notice this podcast started at 11 a.m. 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 has to sit down and actually create all the content?

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Can you show us how to get the AI to challenge you instead of... Oh, yeah. Let's do that. So coming back, AI that argues back. So this is pretty simple, right? I use Cursor as my daily, like, agent. But if you're using Claw, if you're using Chattip 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 MD. That's kind of what it uses everywhere. Claude has a Claude MD. And basically I have a file that's like how to work with me. And I have it, be direct and honest. I need the truth my coworkers are afraid to tell me. I need you to challenge my assumptions.

I need you 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 Wade wants. 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 placate you because it thinks that's what you want. And so you do have to tell it, you know, it's sort of guided 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 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 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've made, which I call my war 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, y'all, 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. And what it will do, the war council is this is a actually, let me poke back. I think I have the war council skill in here. Ah, yeah, here it is. Okay.

It didn't actually pull the skill up. This, if you go to Zapier's GitHub, you can get a copy of the War Council. But what this does is it spins up subagents. And these 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 War Council.

There's the ruthless CFO is a standing member. There's a contrarian board member that are standing members of the War 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 like Travis Kalanic transcripts or something. Like what did you, how did you do that?

In my case, it's a generic version, but you could do whatever you want, right? If you want it to have like Travis. What does generic version mean, though? You just said you be a,

I just said, these are the traits of, I said, this is the traits of a wartime COO. And it like, I said, actually what I did was said, I won a wartime COO, you know, generate that persona. And then I looked at what it created and just made some like, do you have like a pretty chill, generally happy, positive outlook? Like, like, this is, this is you're seeing the like the, the internal competitor inside of me, right? Like, this is the, the Kobe Bryant, Mamba mentality, like, you know, like coming through. I like having 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 going to have people who are comfortable, available, skilled in that way around you, right? Like this is 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 it sounds like you're using it to chat, make decisions. Am I just wrong about what cursor is? Yeah, I mean, cursor, you can use cursor, cloud code, code, codex. 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 clog code or codex to be the engineer you delegate things to. Where it's like you probably have engineers you've worked with. You like to tell that engineer, go build this for me or go build that for me. That's why I use cursor is because it goes and build stuff for me, not because I'm using it to actually go build a bunch of stuff.

I don't really write any code. Wait, 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 chat GP or cloud 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, you know, test a bunch of different models and things like that.

Are you a typer 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. Like I've tried a few of these. I've tried like whisper flow and super whisper and monologue.

I don't know. it just gets me. I don't know I don't know of a better way to describe it. Quick side note. I think this is going to be 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, 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, it's, yeah, no, 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 Blake 182 documentary last night? Do you guys remember Hurley? Sean, you remember Hurley shirts? They're everywhere. And I was watching the show. show last night. I'm like, why did 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 it so much? And I think that's a good point. That's how we're going to think about B2B, even B2B boring software.

Well, that's what I think is a really fascinating point because it always was differentiated on either features or price, right? Those are kind of the two main axes of competition. And then design got layered in. And I feel like there was like a wave where better design, better UIUX became a differentiator and design, you know, got a seat at the table. And then, but if you look at like other products, non-software, it'll be either

kind of brand or like status, you know, like luxury. It's signaling something about you. That doesn't really exist in software. And it sounds like what you're saying is there's going to be a new axis of competition, which is personality. You know, who do I like to feel of when I'm going to interact with

it versus which model has more parameters and, you know, a higher benchmark score on the e-vals is not going to be how people are going to choose these things. Because I'm already doing that year. I think you're absolutely right. Well, and I certainly feel it like, 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 where I don't need to talk to it, there's models I like for 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, it is not fun to talk to at all. We all have coworkers like that. They crush it at some tasks, but you're 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 than like trying to talk to Fable where I'm just like, oh my God.

all the phrases, like when Claude talks to me, it's like, what are its phrases? It's like, it's not this, it's that. Or here's the thing that's quietly really the problem. Yeah, the honest truth, 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 said, like, let's get to the load bearing part or like something like of like, like, like when they're talking out loud, not in writing. Yeah.

Yeah, yeah, yeah, yeah. I've noticed that where they start saying things. I'm like, that's Claude. And it's sort of like... You want to plug them? 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 AIs or the AIs training us? And I think you can go a step further where actually, let me show you this other use case. Because 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. And 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, Acmeal logistics here, you can see, you know, a bunch of stuff about it. It's like, oh, you know, usage is down 34%. There's a renewal in 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 in on them, 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 the AI the boss? 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's 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 candidly 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've got to keep in touch with everybody. And so now I've kind of put an agent in the loop and said, like, 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 end. 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 where Jack Dorsey from Twitter came up with the idea and it was 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 the 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 going to do a better job. And so that kind of changed how I thought about it. And 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. Like, it just can. Like, 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. Like, to start right now, it's like you use it as an assistant to sort of help you make these decisions. But it seems pretty plausible to me that you might start saying, hey, I'm going to take its suggestion more often than not in certain places. Yeah, I think that's not true. I wonder if AI is going to have like, because, you know, the upside would be AI that 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, you know, avoiding conflict or, you know, 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

We know we have this sort of sunk cost fallacy and we have this bias for recency bias. What is AI is going to be? Because we're going to need to be aware of those, the more we'd sort of turn over decision-making to AI. Yeah. Today's podcast is brought to you by my friends at Mercury. They make the world's best banking product. I think you know this already. I use Mercury for all of my businesses.

I think I have like maybe seven or eight businesses. We use Mercury as our business banking across all of them. And now they actually just launched a personal banking account. So I have my personal account there. I moved off of Wells Far. go and chase. I'm just all in on Mercury. Why, I like products that are easy to use. I like products that get me and the problems that I have. So like very easy to make a joint account with my wife, very easy to spin up virtual cards, one click and I get savings yield. It just has all the stuff

that I need in one place. So if you're looking for the best banking product on the market, it's definitely Mercury. I will fistfight anybody who disagrees with me on that. Go tomerc.com slash personal and learn more. Mercury is a fintech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column NAA members FDIC. So you run a company that's worth billions of dollars. How many decisions are you making a day that it's actually weighed versus AI? Well, I would say like any high stakes decision, the AI is weighing in on now. Like, you know, there's sort of a seat at the table and, you know, the exec meeting and the board meetings and all that sort of stuff where we're asking the AI to 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 come back to the hiring example. So, you know, we run a barraiser process where I approve every job offer that goes off. But like, exact team member 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 at Zapier?

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, I've 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'm, but I'm, I can still smell it. I'm like, are, and so I would often go to these folks and be like, are you sure something that's off? Like, I don't, I don't think they have this, 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, and I'd kind of 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, efficiently answered it, then I will back 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 that person? And I'm like, ah, like, so anyway, that's kind of what it would. was happening pre-AI. Post-AI, I'd run the War 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, give like a score of like here,

compared to everyone you've hired its app here, 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, what's going on here? And I noticed all of a sudden the behavior shift where people would go like, oh, interesting. I think the 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. It's like, I want, like, what else, what else am I missing? What am I not seeing here? And I just found that like, 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 actually has a way of talking that makes it 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 loop. 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 tests before you hire someone, Ray Dalio has his version of it, whatever.

And there's like, tends to be, it's like a scale where people fall in where they're like, I don't believe in anything involving like personality tests. I have noticed with AI, I have fallen closer to the side of like I follow what it says because I've done some of these personality tests 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 test and like figuring out if a person could be good 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 test 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. Just get more cameras. Let's get LiDAR. Let's get radar.

Let's get sonar. Let's, you know, put a, what else can we do? Taste test. What are all the different possible sensors you can put on the car? And the Tesla 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, like, LIDAR was very, very expensive. So it was 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 more faulty, more error prone. And actually what you should do is take only the minimum number of sensors needed, but the 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, but those have to be home runs. Otherwise, I'm just not going to hire the person. So what I mean by that? Yeah, yeah. Answer the question, though. Like, how do you get, 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,

this or this or the. Okay, so how do you gather that information? So again, stealing from Elon, he he talks about you want 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 coattails doing that thing? And if you really haven't done anything exceptional, the odds of this being the place where you have, the, 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 don't, they're 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 a signal. But obviously, like, I'm not running the size of org that way it is.

And I'm working with people who are working directly with me in a very, very small team where everybody has to be, you know, 10x or better. Otherwise, this is 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 this one called Burkeman that we've done at times. I have found it to be moderately useful. I have a CEO buddy who runs this public company in Columbia that does dis profiles for every hire. And he's like insistent where it's like if I have an accountant, they need to be this profile, this dot-da-da-da-da. And 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 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 traits, I'm going to be way better because they're going to have my backside in places that, I don't know if there's any science behind this, but if you look at my EA versus my like Myers-Briggs, she has three different letters than I do. So there's four letters in that and three of hers are different. And she does like have, she like 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's kind of like in sports where it's like you know

if you're basketball team it's like well you need somebody that's gonna you know Michael Jordan's gonna shoot all the shots well you need Dennis Rodman who's gonna like lock down D and grab boards but are you doing that for when you guys are hiring we don't do it no we don't actually 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've an idea for how I think companies could use AI to improve their hiring. I don't know if this was fully 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'm in. You go through your team. So you have all the past hires you've made in 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, let's say. Cool. So you could stack rank employees. and your team and you could say, great.

You also have maybe the transcripts or the recordings of all the interviews that they did. So you have this historical pattern that you have with all of them. And then you have new people that are coming in. And so when I was at Twitch, they used the Amazon Barraiser 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 the pattern of past candidates as well as against your values and, you know, the role in mind. And I just think AI is going to be way better at that than people. 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? I don't know for sure if AI would be good at that, but I kind of think that would be helpful. I mean, I remember Google sharing 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 talent 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, 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 70% of the reasons why I have a company just because I like want someone to hang out with because I'm not good at friends yeah friends are hard employees are easier starting starting LLCs is easier which sounds like a joke but like any you know I'm sure Sean you agree like you Sean has a guy who works with him he's like if 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 you want to play Fortnite and we just played Fortnite for a couple hours like yeah absolutely I need a pickleball partner. Can you come be my employee? I mean, that's kind of how it is. I just want to like hang out people. But when you have, okay, now I'm not, 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 could kind of go unhinged. Unhinged mode. Okay. Yeah. But Wade, War Wade. Yeah. I don't know how many employees you have now, but you used to have 700. What do you have now?

It's like 730 or something like that. It's not. 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 they, many of them 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, Kim, like, one person just be, like, 10 or 30 different agents that they monitor, and you only have, like, 20 employees? I think 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 rulebook says 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. Well, 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 assigning you tasks and more things to do and more things to do. And so there still 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 a company like Zapier, I'm not sure. But definitely like a company could certainly do that. In fact, we've already seen companies that have 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 GLP1 stuff. Yeah, we had them booked as a guest on the podcast. And then that article came out the day before and he canceled on us. Well, so yeah, like, you know, 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? You have two inmates? Yeah, how many cellmates does he 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 at her peak was. So, you know, I think it just kind of depends on the business. 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. Is that, 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 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 said the same thing. You're saying I'm right. I'm genius. Yeah. Like you're, I, we got there. We got there.

And again, this is ruthless weight. So I 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're, 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 every day waking up and managing flea? of agents or you want them talking to your customers and helping build those relationships and close that trust and all that, da-da-da-da. For that role, I'm like, I think I kind of want you building 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. or Miss, like front-line sales A.E., 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 it a good time. I mean, it feels, honestly, it feels a little fictional to even hear you say that where I'm like, I don't think of myself like that way. And And it sort of is, like, so much is like tied to like the paper, the paper worth of Zapier at 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 to 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, the, like, things one, two, and three are my family. And so, you know, 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, shoot, if you 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, shoot, when I was, I remember when I just got out of college, my dream was if I could only make $100,000 a year. That was my dream.

It was like, if I could make $100,000 a year, I was like, man, I'll be set. That was mine too, by the way. It was like, if I can get out and work at KPMG, and get 60 grand. I might get it to 100 grand before I'm 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.

Like, that kind of stuff. 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 to go on a 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 a safari. But I do that now. I don't need billions of dollars to go on a safari. The reason I like asking you about this stuff is because you are very well-rounded. And you seem like we had this joke called 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 needed to be ruthless. They were sweet when they needed to be sweet. They were smart when they needed to be smart. But they were still 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, ourselves, or myself included, talk about it from a, they're broken, they have a chip on their shoulder perspective, whereas I don't think you have that. You have a, you have a far more wholesome and a positive outlook when it comes to a lot of this stuff. So 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, you know, I was really lucky. Like I grew up, you know, with a, like, a, you know, a family that was all sort of like, you know, my parents were married, my two grandparents that were married. I have like aunts and uncles and cousins. that were all sort of just like really tight-knit.

But if I was to like give a shout-out to any of those, like I got to talk about my granddad. Like, you know, my granddad is a World War II 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 a 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 Pam. every single day. And I remember going to, you know, after he died, we were at the, the funeral home and they were trying to, like, plan 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, 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 nonstop. 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 highway patrolmen 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 great, at family and great at professional stuff. And I just, that to me was like just a really good example of, you know, someone who got their like priorities doubled, like dialed in really, really well. You know, he didn't have it all, but he didn't need it all. It's like the things he cared about, he, he nailed them.

And so to me, that's always like stood out as like what, what a good life looks like. Sounds like a good role model. I think that you definitely seem to embody that where like I said, you are great business and also like don't have this jackass side that most people who are where you are seem to have right Sean yeah yeah we um first I love that story that you just told that was actually a really awesome an awesome story and also you know I think that the value of what you just said you said two things that said to me you said he didn't have it all but he didn't need it all and I think that you I've been thinking about this a lot lately which is that you're really only as as rich

is what you don't need. Basically, like, if you don't, whether that's material things or 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. Right, like, you know,

you don't have to go be super flashy 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 reminded me. It sounds like your grandpa had that kind of way of life. And the other was, you know, you know, defining what winning is. So it's like, if winning is just in the work domain or winning is just in one, you know,

just in one of the way, if 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, if the media portrays Jeff Bezos or Elon Musk or whoever, as 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 don't Like, 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. I'm a basketball fan. So I grew up being like Jordan is the goat. He's the greatest. He's the best. And he is when it comes to basketball. But he also had many things in his personal life that I don't want to emulate. And 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 Star is for you so that you kind of have a clear picture in your head. It makes all future decisions really easy. Totally. I love that. Like, you know, define your own definition of winning. And, you know, 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, If what you want to be doing is, you know, running a software company and, you know, great, go do that.

If what you want to do is, you know, be a teacher and, 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, it's like, what is it that sort of is winning for you? Do you have any examples of that? I mean, you are very successful and you moved from San Francisco back to Jeff City. 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 way before anyone thought that 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, we're building this business for like the long haul. And so, again, I constantly get questions around, like, well, what about? I mean, heck, you guys are asking me about. It's like, well, what about the X or what's the valuation? And I'm like, it'll be what it will be. Like, we're here to grow it for our customers. Like, that's the thing I care about. Not these other things. And, you know, I think if 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. And I think that's, you find that with anyone who loves what they do, you know, 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 hoarding their money, they're and all this stuff. I mean, look, I don't know all billionaires. I've gotten to meet a couple. And, you know, Darmesh, Halligan, like, you know, guys like this who, I don't know, they genuinely just seem like they like what they're doing.

And 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 of sight to money. Then when they made the money, they kept doing it. They kept doing it.

It wasn't about the money because... I just like doing it. I think athletes are the same way. Like, you look at like Olympic athletes. Olympic athletes don't 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 HustleCon 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, you know, billionaires or like these, big shot CEO is just like interacting with you, having a normal conversation. It was really exciting. It was like people watching on steroids. And we were 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 was like the entire day. And I was like, do you got somewhere to be? And you're like, nope, I'd 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, you were 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 it being eight or ten hours, but I do remember it was all day. Like you got at nine, and I think we left at four. So however long that is. Maybe it was, yeah. Yeah, I mean, you got good,

you pulled good guests, man. Like, who wouldn't 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 notebook of ideas that I sort of took back and was like, all right, we're going to try this. We're going to do 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 of a deal. But now, like, God, you can just like pour over this stuff and you just have like notes for days on things that you can just go try and just like, all right, see if this works for me. What do you listen to and what do you consume on a regular basis? Books, podcast, whatever. My favorite podcast, I gave a shout out to the acquired guys. Like, I mean, it's just 10 out of 10. Like, you know, most of those things they do a deep dive on are just these legendary entrepreneurs.

who've like, you know, did it for decades. Leave us a, leave us with a recommendation, give us an Acquired episode we should listen to and maybe a book that you liked. Well, the NFL episode, if you like sports at all, like, you know, that is a good entryway into Acquired. Though probably my favorite series is all the retail ones. So there's like a, like a, like I think it's Costco, Walmart, and Amazon.

And there's sort of like a trifecta 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 That's a really good one

You know I think Steve Jobs He sort of He 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 chronologically

And so you get to kind of just see His progression of like you know, V1 Apple, the Pixar years, V2 Apple, and you kind of just see how he changes, sort of like over time. Sean, do you have a book that you read recently? You want to recommend?

Yeah. There's a book called The Score. Have I talked about that here? See, Ty Wynn, is the guy's name on the cover. But 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. So he's talking about the power of a game. So he's like, imagine a game. Let's say we take a Pictionary. We open up a game of Pictionary. 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 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 have to be highly communicative. You're going to have to be a great team player.

Whether you're the guesser or you're the actor, it doesn't matter. But then let's say you play risk. It's like you're going to have to be like ruthless, dominating. And so like he's 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 games we play in life. And so he describes like when he was this professor, he's like, I got into teaching philosophy because I love philosophy.

Of course, that's why, who else becomes a philosophy teacher? 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? I don't want to be not on the board. And so he kind of innocently is like, oh, you got to get published. And he's like, well, then I realize like the way to get published the most and the

fastest is 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 even doing this? Like, I'm doing studies about shit that I don't even care about. get published to get on a leaderboard, that doesn't even 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. There's, like, striving play, which is, like, you play for the joy of playing versus, like, outcome-based, where you're playing to win. And, like, you know, you want to be

a striver for these reasons. And that 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 when you remember that, oh, the reason we're playing strades

is so that we could have a fun time as a group hanging out, not so that I got the most points in the game. And so, you know, there's all this, like, nuance around 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 of your behavior. Looks like it just came out too. The book came out like six months ago. Yeah, so I'm digging that book right now. I just finished. I'll wrap it up with this one. Wade, you might like this one. I think you, if I had a guess, do you listen to Blake 1-82 as a kid? I did. I did you, Sean? I mean, who didn't? Yeah. I wasn't like going to concert. I read the biography of the memoir of Mark Hoppice, who is one of the lead singers of Blankwin 82. Such a good book. I read it in three days. I couldn't put it down. It was one of these books where I had to force myself to put it down when I was going to bed at night because I was like staying up to. late. Dude, why are musician biography so good?

I'm desperate for more. Whatever of musicians and comedians. What else do you have? The Red Hot Chili Peppers guy, Anthony Kedis. Was that good? Long time ago. I was like in college. I read this thing and I loved it. Well, his is good, I think, because he had a messed up and he partied.

Messed up 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, I'm going to, this is the chapter where I complain about fame. And he was like, just joking. I love being famous. It was awesome.

Like, people come up to me all the time and they say they love my work. It feels amazing. And then he also, later in life, he got cancer. He talks about, like, his cancer treatment. Oh, such a good book. If you guys want something fun to read, Mark Hoppus has a biography. And if you want, like, the cliff notes. What's it called?

Fahrenheit 182, I believe. But anyway, wait, you're the band. 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 the pod. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel, never looking back. All right, let's take a quick break. I want to tell you about marketing school. It is a podcast that is 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.