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

0:00 Wait, wait, Sam, you gotta clickbait it up. How five billlion dollar founder is using AI. To change his life. Well, are you a five but what are you guys worth now? Who knows? You know. You know. You you

0:15 I feel like I can rule the world I know But I want to I'm putting my law in it like a day's off on the road less travel never. Alright, we should do a little intro. So first do you is it? I've been saying zapier my whole life.

0:30 Is it Zapier or Zapier? Zappier makes you happier is the trick. It runs happier. Happier. Wow. Dude, how is that not your slogan? Here's your slogan is on your site. The automation layer for a genic AI. It doesn't really flow the same way as Zapier makes you happier. It doesn't.

0:46 We could so there's th two things from the name. We one, we just couldn't afford the second P when we started when the 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. 'Cause it's all connecting all the A these APIs and all that good stuff. I didn't even notice that. Didn't notice that. But also if you played Zapier makes you happier, I would have read it. As

1:13 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.

1:30 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 kinda 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 could 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

1:57 Several billions, maybe five billion was a number that I had seen at some point in time. And I I think you had bootstrapped a very long way. I don't Is it purely bootstrap or are you at some point took some money? I think the word

2:08 people call it now a seed strap. So we did go through Y C and we raised About a million in change. But that's all the primary capital we've ever taken. Yeah. So just incredibly to to raise a million bucks and then get to five billion in value is just pretty pretty wild. So Super cool, but we're here not to necessarily tell the whole story of How Zapier makes you happier, but

2:28 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 OG V one 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.

2:50 I haven't been using that. I also here's the other caveat. I'm kinda 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?

3:02 But they're smart at the same time. I have really good news for you though, like I think AI is This incredible gift to people who are kinda dumb. Because you can just agree, talk to it and say like Hey, I didn't understand that answer.

3:21 Explain it to me like I'm five. And so you can keep like Going down the dumbness sta stack, I guess, for like 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.

3:34 So okay. The sales pitch. You want the sales pitch. In the old world You know Zapier. You know, come in.

3:40 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 you know, Kodak or Cursor or or You know, open claw or w whatever it is that you like using, right?

3:54 And you're just talking to it, going back and forth. Most people start with that. AI as a chatbot is valuable, but it's only generally smart. It knows everything that the internet knows. It doesn't know anything about your business.

4:06 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 it questions about my first million and all this other stuff. You get not just generally smart answers, you get hyper specific answers.

4:27 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 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, use the native connectors, do whatever you want. The next layer And where this gets really powerful.

4:50 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. Like that's where you start to get the real magic.

5:03 And the reason you want to use Zapier to do that versus like any of these generic agent builders. What was an what's an example. I mean, like you know, Claude has routines or chat GPT has scheduled stuff. Like, you know, there's a bunch of these things that can kinda 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

5:24 Is Optimized to run more deterministically than agentally. And I don't think people have caught up on this yet, but you've probably experienced climbing up the IQ scale. I know, I know. Hang tight, hang tight, hang tight. Agents Agents. They kinda just guess what to do, right? And if they're smart enough, they guess right most of the time.

5:43 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 gonna write code for you and we're gonna write workflow logic for you, which means that it's gonna run. Like a machine runs. And so you're gonna get

6:02 It's not gonna burn tokens. It's going to be reliable and accurate, and it's only gonna use AI exactly where it needs to ru to to use AI. Got and you've got this. Um you can host it. on Zapir.com, so you don't have to sit here and like keep your laptop open to run these agents in the background. And so you just get this like rock solid infrastructure that Zapir's always been great at and the hookup of everything that we've always done.

6:27 But you can build Oh yell inside Claude. Which is like really nice because Claude just kinda The the natural language style of building is

6:36 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 the sell me this pen test and you you did a pretty good job there. So I appreciate that. I feel like I now actually understand it. So that that was good. Well and here's the magic. You can t if you didn't and you're just pretending and being nice You can take the transcript of this.

6:57 And you can plug it in a claw and say, Wade said this weird thing. I think it's a little bit more than what I'm telling what this guy was talking about. Tell me what he was really saying. And that's like the cool part of AI. Uh that is cool. You gave us a list of stuff. So we said Wait.

7:11 What are you what are you making? 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. How a five billion dollar founder is using AI.

7:28 Change his life. Well are you a five but are you guys worth now? Who knows? You I mean you I don't I don't know how the markets behave right now. They're like up and down all sorts of ways. Like I'm gonna be I don't think about it, honestly. Like I I'm just like how do we build stuff that makes our customers successful? I knew you were a sweet guy. I didn't think you were a liar, though. Yeah. Because I I know you think about it. Under oath. You know, no. There's the there's the old saying, right? Like in the short term, the markets are a voting machine, in the long term, they're a weighing machine.

8:02 I'd rather you just tell me F off than give me these lies. I know you think about it. But don't don't piss on my back and tell me it's rainwade. Honestly don't. That's fair. Since the last time you guys got value. That was a secondary number. Sale that happened. And Twenty twenty one, maybe?

8:27 Okay. Our 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 as a high functioning CEO.

8:43 Okay. Let me share screen on some of this stuff. So we'll get into the to 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

8:57 Help me demo this stuff. And so This is this is what it came up with. It's like here's the stuff you should actually go 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 CO CEO CRM that I built that

9:17 Helps me. stay really close with our enterprise customers. Um I've got um like an AI that argues back. I think this is a really important thing that Every like leader needs to 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.

9:36 And so you need to Um J like there's a few ticks and tr tips and tricks you can do to like force it to like scrutinize your thinking rather than Just tell you, Yeah, you're 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

9:51 Tasks. Internally. So Yeah, I I would probably start with the robot staff. I think this is like cool to to dig into. The first thing and we'll we'll I'll show the complete version of this. Where I think most people start is kind of the morning brief.

10:05 You know, it's super simple. It's a good It 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 Yeah, any meeting.

10:18 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 six A. M. in the morning and then it sends me A Slack message. Yeah, I call I call this waking up like the president. Like the president wakes up, it's a gets a daily brief. Here's what s sir, here's what you have on your your plate today. Nine thirty, you're talking to this person, ten AM, this person's here, here's what they want to talk about. That sort of thing. And so waking up like ever now everybody gets to wake up with a presidential briefing.

10:44 Exactly. And so, you know, these things run 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 it doesn't do it all the time. And I also have this woman named Ari conveniently because I told uh I t I wanted to make it come from Like a a person and the person they made. Is that weird for you? That Sam named his agent after you? The person they selected looked at looked like Ari.

11:14 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 Bridge. There you go. Now so the cool thing, I'll actually show you. So I I have the link out to this one. This is you know, this is running on zap here. And you can see

11:30 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 AM. It goes and fetches all the calendar events. And then here it's um writing some specific code and hitting the AI to like 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

11:50 In the past, like you couldn't do this with Sapper. Now, I've not actually looked at any of this code. Like this is actually the first time I pop this open and even taken a look at what this is. So you don't have to know. What's going on here? Um, but again, it kind of speaks to the value prop of Zapper is 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.

12:15 And way more cost effectively than than most agents. So can I use this instead? Like the problem that I have with clot 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. Mm-hmm. Would would doing it on Zapier just be like in lieu of using like Open Claw or having a Mac Mini? There you go. Exactly the the point. You can just deploy these as appre and we run them in the cloud for you. That sounds way better than using Open Claw or having a Mac mini. So way, way simpler, right?

12:46 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 up to a five billion dollar 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 the scripts that he's talking about, and we put it into a really easy document. So you just copy and paste everything. So there's 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 can just copy and paste all the stuff. Just click the link in the description or scan the QR code. All right, back to Wade.

13:32 While it is running deterministically. If For whatever reason it breaks, like say an API is down or Yeah, something doesn't work right. It falls back.

13:43 To having an AI try and troubleshoot for you. And so it'll automatically apply fixes. you know, when things don't work quite the right way. And so there's this like really nice blend of like traditional software and like agentic software here that is just Um yeah, super well done. By by the team over here.

14:01 So I I definitely would say, Hey, if you're if you're struggling with your open claws, if you're like keeping your laptop open all the time. You should definitely installs Appier into like your you know, agent or AI of choice and and give this a try. Okay, what else? So you get the morning brief. That's pretty standard, I would say.

14:20 So I think the morning breach is pretty standard, but the one that I really like is The the evening brief in the scribe. So Yeah, 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.

14:39 Breathing. And the reason why is you can actually have the AI help you do stuff. So Yeah, it

14:46 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-do's 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.

15:02 And it s 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 what 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. But the second thing that it's doing Is

15:23 It's actually taking action on them 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?

15:36 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 I'll just do that for you.

15:52 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 Yeah, just trying to catch up on every little Ticky Tack thing that I sort of got roped into and now that like two hours at the end of the day.

16:14 Is down to like Fifteen minutes. So y you think this is legit saving you two hours a day almost? I yes. Yes.

16:22 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 um like I remember

16:35 Ninety like about n about ninety 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? It was like sure, and it did all that stuff. And then I gave it to my assistant and I said, Hey

16:54 Here's like Please make my days look Like more good days versus bad days. Wha what were your good days and what were your bad days? So for me, like the single most important thing is I I'm a morning person. And so I do my best work in the morning, I'm most focused. Um yeah, once once after lunch comes around

17:11 You know, I I'm just not gonna get anything like serious done. And so the most important thing is I don't want a meeting until eleven AM. And so You just give me that morning time where I can knock out The most critical things. And the day's gonna go great. Like I will win the rest of the day. But if I have to like

17:28 You know, it if 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 eleven AM. Ha ha. 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?

17:51 That someone is usually and it's due tomorrow. Well, the breeze assistant from HubSpot can help. It works right inside HubSpot. You can draft a 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 agentic customer platform for growing businesses.

18:11 Can you show us? How to get the AI to challenge you instead of uh Let's do that. So Coming back, AI that argues back. So this is pretty simple, right? I use

18:23 I use Cursor as my daily like agent, but in if you're using Claude, if you're using ChatGPT, 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 as the agents MD. That's kind of what it uses everywhere. Claude has a Claude MD MD. And basically I have a file that's like how to work with me.

18:43 And You know, I You know, have it be direct and honest. I need the truth. My co workers 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 disag like disagree when you genuinely disagree. And these things are like goal seeking entities.

19:00 And so if you tell it like what I want from you is this It's gonna say, Okay, well that's what Wades wants, so I'm gonna 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.

19:18 Yeah, it 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.

19:31 Right. So this is like something that It should definitely like say, Hey, press pause. Like that that's a 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, it's a big move off a pretty thin signal.

19:45 Before you draft anything, I want you to I want three things on the table. So like, you know, br 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.

20:02 you know, these um 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 Yo, I'm thinking about hiring this person. Here's all the like

20:19 Notes that I've got on them from the interview panel. Like, help me figure out if this person's gonna raise the bar or not. And what it will do, the war council Is this a actually let me poke back. I think I have the war council skill in here. Uh yeah, here it is. Um okay. I It didn't actually pull the skill up. So

20:36 This if you go to uh Zapier's GitHub, you can get a copy of the War Council. But what this does is it spins up Sub agents. And these sub agents take on personas.

20:47 There are Seven sub agents that get spun up. So seven personas. Some of them are standing members. So for example, I have Uh the wartime COO. is a standing member of the war council.

20:59 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 in To be generated dynamically. So based on the prompt. It will decide.

21:14 Who else 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 Kalannick transcripts or something? Like what what did you how did you do that? In my case, I ha it's a gen it's a generic version. But you could do whatever you want, right? If you want it to t to have like travels. What does generic version mean, though? You just said you become a I just said these are the traits of I said this is the traits of a wartime COO. And it like I said I actually what I did was said I want a wartime CO.

21:44 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 This is this is you're seeing the like the 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 like, you know.

22:07 this sort of thought partner that is a little more bit more like ruthless because that's not my 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 the this is this is like who you would want on your team when when you want them to spin up. Quick uh stupid question. You said I use cursor for my AI. I thought cursor's a coding tool, uh but you're it sounds like you're using it to chat and make decisions. Am I just wrong about what cursor is or Yeah, I mean cursor you can use cursor, claude code, codecs, like these are all ostensibly coding agents.

22:44 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

22:55 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 cloud code or codex. To be the engine you delegate things to. Where it's like you 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.

23:15 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. 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 GT or Claude or anything. I mean mostly, especially when I'm at my desktop, I'm mostly talking to Cursor. Most of the time.

23:35 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 talker? I I'm I do a lot of voice to text these days. So I use this um

23:50 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, um I don't know. It just like It it just gets me.

24:03 Um I don't know, like I don't know of a better way to describe it. Quick side note. I think this is gonna be like an interesting thing about software for the future. Like when it is so cheap to build software. I think you're gonna see more software that has Like a personality to it. You know, you think about like

24:22 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 gonna be more software that kinda

24:41 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 I remember I was watching uh this Blake One Eight Two documentary last night. Do you guys remember Hurley? Sean, do you remember Hurley's shirts? They're they're everywhere. And I and I was watching the show last night. I'm like

25:02 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 us so much? And that's i I think that's a good point. That's how we're gonna think about um B2B, even B to B boring software. Well that's that's I think it's a really fascinating point'cause it always was differentiated on either Features. Or price. Right. Those are kind of the the two main axes of competition. And then design got layered in and I feel like there was like a wave where

25:28 better design, better UIUX became a differentiator and then 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 um Kind of brand or like status.

25:43 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 gonna be a new axis of competition, which is personality. Uh you know, who do I like the feel of? When I when I interact with it versus which model has more parameters and, you know, a higher, you know, benchmark score on the evals is not gonna be how people are gonna choose these things. Cause I'm already doing that. You're I think you're absolutely right.

26:06 Well, and it I certainly feel it like You know, as someone who plays around with a lot of the models. I 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.

26:22 There's models I like for that. You know, like Fable is fantastic. Like you're gonna give it a really complex like, you know, engineering task. I'm like, great, have Fable go take a take a swing at this. It's gonna 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 co workers like that. They 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 I feel like I can, you know, tolerate that discussion a lot better. And like trying to talk to Fable where I'm just like, Oh my God.

26:58 I I are all the phrases Like when Claude talks to me, it's like What are the what are its phrases? It's like um It's not this, it's that. Or here's here's the thing that's quietly really the problem. Yeah, the honest the load bearing, you know. Yeah, like here's let's get to the spine. Uh are those

27:18 Specific. To AI or to the model? To the bottle for sure. Like you can tell Most models I think are derivative of either either the um 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

27:35 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 Yeah, the one above. Dude, I've noticed that my co workers are starting to say Like the clawed like someone the other day said like let's get to the load bearing part. Or like something like of like

27:53 Like when they're talking out loud, not in writing. Yeah. Yeah, yeah, yeah. I notice that too. I've noticed that. Where they start saying things, I'm like, That's Claude. Yeah. Like or 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 are the AIs training us? And 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

28:23 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, usage is down thirty four percent, there's a renewal in forty-five days, here's all the apps they're using, here's the people in the organization that you need to care about. Etc. But then like here's the interesting part. It's got the suggested CEO outreach where it's like you should email Jordan.

28:51 And You know? Check in 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?

29:01 Like am I the boss? Or is the AI the boss? Yeah, 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.

29:16 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 gotta keep in touch with everybody. And so now I've kind of put an agent in the loop and said, like hate me help me be better at this stuff. And

29:32 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 in. And I think there's like something to this where You know, if you if you do a good job of like building these tools up They'll kinda start telling you what to do.

29:52 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, the um one of the founders of HubSpot.

30:07 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 gonna 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.

30:28 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 be actually be m be making the hard decisions'cause it's likely gonna do a better job. And so that kind of like 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.

30:54 It's gonna be able to reason over way more information than a human CEO. Like it just can. Like it 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 gonna know. And so

31:15 That's gonna make it way more useful for certain types of decisions. Like at 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 I'm gonna take it suggestion more often than not in certain places.

31:33 Yeah, I think that's not true. I wonder I wonder if AI's gonna have like 'Cause you you know, the upside would be AI that is not gonna have the emotional roller coaster that a human would have or fears that would hold it back from doing the right thing. Or avoid you know, avoiding conflict or you know different things that humans have as their biases. And then I wonder if we're gonna have to come up with the cognitive biases of AI to watch out for. Like, okay, we know we have this sort of sunk cost fallacy and we have this Bias for recency bias.

31:58 What is AI is gonna be because we're gonna need to be aware of those the more we sort of turn over decision making to AI. Yeah. Today's podcast is brought to you by my friends at Mercury. Uh, 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 Fargo and Chase. I'm just all in on Mercury.

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32:48 Mercury is a FinTech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column NA, 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 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 kinda changed your mind or

33:20 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. Um, let's come back to the hiring example. So Yeah, we we run a bar raiser process where I approve every job offer that goes off, but like exec team member sort of

33:38 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. It's up here. Now In the past, pre AI, when I would go through those approvals

33:54 I would often, you know, if I would come across a canet 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 l looked over thousands of applications where I just have more reps than most hiring managers have. Like most most hiring managers hire hire one or two people in a year. It's like I'm 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.

34:19 But I can still smell it. I'm like Ar and so I would often go to these folks and be like Are you sure? Something is 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

34:34 I stand by this person, like, wait, are you just gonna make the hiring decision? If so, like you just if you don't wanna hire him, don't hire him. 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 so you know efficiently answered it, then I will back you. Let's go hire this person. But if you haven't

34:59 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? Right. And I'm and I'm like So anyway, that's kinda what it was happening pre AI. Post AI.

35:19 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 in the panel. Did not.

35:34 Scrutinize this. So you need to go scrutinize this and it would s you know it'd give like a score of like here compared to everyone you've hired at Zapier, here's how here's how likely I think they're gonna be successful or not. And so now I could take that to the hiring panel and say like Hey.

35:51 The the AI said this, I agree. Like what are 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.

36:03 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 be maybe because it's not Maybe because it feels like arguing with an AI is easier than arguing with a CEO, or maybe because it's more eloquent and it like actually

36:21 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 the the eye 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.

36:44 Ray Dalio has his version of it, whatever. And there's like Mm. 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've 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

37:04 When it comes to hiring, do you guys buy into this at all when it comes to um 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 I go the the other way, meaning it's not really about personality tests per se.

37:22 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.

37:31 Just get more cameras, let's get LIDAR, let's get radar, let's get sonar, let's g you know put a what else do we do? Taste test. Wha what what are all the different possible sensors you could 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 s the reason that Elon says that he Did it was because when you have too too many sensors, you get too much conflicting data. And

38:00 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 then train the train the hell out of them.

38:11 That's kind of my approach to hiring. Where I now simplify I need less time. to ho to spend with somebody and I look for fewer things and but those have to be home runs. Otherwise I'm just not gonna hire the person. So what doesn't matter. 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? Okay, so how do you gather that information?

38:35 So again, stealing from Elon, he He talks about the you want evidence of exceptional ability. So all I'm looking for, I'm not looking for like So the fur 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 gonna 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 that thing? And if you really haven't done anything exceptional, the odds of this being the place where you have the the final the you know the first exceptional thing of your career is not really a bet I'm excited to go take.

39:13 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 uh you know, gut gut feel of like Do we have creative chemistry? Do I feel like this person is a good to have in the room when I'm trying to figure something out or

39:33 Do I feel like they don't they're not 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 is signal. But uh obviously, like I'm not running the size of org that way it is. And I'm I'm using I'm working with people who are working directly with me in a s very, very small team where everybody has to be You know, ten X. 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

40:02 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 Berkman that we've done at times. I have found it to be Moderately useful. I have a CEO buddy who

40:16 runs this public company in Colombia that does disc 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 day. 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 you can score whatever you're gonna score, but you still need to be good.

40:42 Yeah. 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

40:56 With somebody who has like Uh complimentary traits? I'm gonna be way better because they're gonna have my backside. In places that

41:04 I I I don't know if like 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'em of hers are different. And she does like have She like likes doing things that I don't like doing.

41:21 And she's good at those things. that I don't like doing. And it ends up being like pretty helpful because I think it's kinda like in sports where it's like, you know, if you basketball team it's like, Well, you need somebody that's gonna

41:33 You know, Michael Jordan's gonna shoot all the shots, but you need Dennis Radman 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 what are you going to do? different hiring managers are probably doing it somewhat like by like organically. Yeah, but it is not a science for us. I've a I've an idea for how I think

41:55 companies could use AI to improve their hiring. I don't know if this was like fully Like legal. I don't know if you could do this exactly the way I'm d gonna describe it, but Here here's the exercise. I'm in. You you go through your team. So you have all the pr all the past hires you've you've made in the last, let's call it three years. And

42:12 You could Stack rank, who's exceptional. Who's acceptable and who's kind of like been a source of kinda hit or miss Performance.

42:21 I'll say. Cool. So you could stack rank employees. And your team and you can say, Great. You also have maybe the the transcripts or the m the recordings of all the interviews that they did. Right. So you have this historical pattern. Um that you that you have with all of them.

42:36 And then you have new people that are coming in. And like so'cause uh when I was at uh Twitch, they used 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 standardized the h the hiring process, but also like Provide.

42:54 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 the the role the role in mind.

43:08 And I just think AI is gonna be way better at that than people. I think it's gonna be like dramatically better at that. And I'm surprised that people aren't Using Bye. Kind of the training data of your existing

43:20 Team. To inform the next hire. Do you think it would work? Like I I don't know for sure if the if AI would be good at that, but I I I kinda think that would That would be helpful. I mean

43:30 I 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 talent where there was like

43:52 only like an in of like a hundred people in that domain. And it's just like their hit rate was better because it was like, Well, there's just only a hundred people that do this thing. And so I don't find that a very satisfying answer. Ha. Like it feels like there should be something to what you were saying.

44:06 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 thirty five 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 seventy percent of the reasons w why I have a company is just'cause I like want someone to hang out with. Because I'm not good at friends. Yeah, like Friends are hard, employees are easier. Starting LLCs is easier. Which sounds like a joke, but like any you know, I'm sure Sean you agree. Like you Sean has Sean Sean has a guy who works with him. He's like

44:42 If uh you can work for me if you move here and we hang out every day. Dude, yesterday I was like, I'm kinda done working. You wanna play Fortnite? We just played Fortnite for a couple hours. Like I need a pickleball partner. Can you come be my employee? I mean that's kinda how it is. I just want to like hang out with people. But when you have okay and 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 the rest of the section, you can be you can kinda go unhinged. Unhinged mode. Okay. Yeah, but war weight.

45:13 Yeah. I don't know how many employees you have now, but you used to have seven hundred. What do you have now? It's like seven thirty or something like that. It's not that many. 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 seven hundred people and they d many of you then don't know you other than like this guy on Zoom and someone who blogs occasionally.

45:37 It kinda like begs the question, like what if They were all just like Or if like can like one person just be like 10 or 30 different agents that they monitor and you only have like twenty employees? I I think Th there's definitely a school of thought where I've heard that.

45:55 I I do think there's limits to this. And The way I think about the limits is that It it's kinda like how a manager has like an ideal span of control. Where it's like oh I can only have like

46:07 You know. I don't know, the the rule book says eight. I think, you know, you're seeing people push the limits now to have like you know, ten or twelve, or if you're Jensen, you've got sixty or whatever. But There's still a limit where it's just like I just cognitively cannot like keep up.

46:22 With like this many People. But you don't keep up with that many people anyway. Like Um When you have a company, like there's stuff happening that you don't even know about

46:33 Mm-hmm. One of your agents. Well, so you could, but the thing is You're only gonna be able to keep up with what, twenty agents? 'Cause it's gonna keep assigning you tasks and more things to do and more things to do. And so there's still is like a there still is like a limit.

46:50 But I'm not saying that it would be like just Wade. But I'm saying like Uh 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 twenty people could do that? For a company like Zapir, I'm not sure, but definitely like a 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.

47:15 Which ones? Well, I mean shoot, like Minecraft back in before Microsoft bought it was like I don't know how many people, but it was like less than a hundred, I think, and it made it cr 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, he we had him booked as a guest on the podcast and then that article came out the day before and he canceled one of us. Well so yeah, like you know, he's doing like

47:41 I 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? Yeah. Yeah, how many cellmates does he have?

47:52 W but I mean you also could think of someone like uh Like Taylor Swift. Like Taylor Swift has a very very small team from what I understand. And it is you know. printing, you know, billions a year or something like that, or at least at her peak was. So I know I think it just kinda depends on the business. Maybe just the philosophical thing of like do do you think that the way

48:13 So the way work worked before was you start off as an individual contributor and then you can g become a manager where you manage a fleet of individual contributors. Yeah. Is the then and maybe in the corporate world your value was proportional to how good you were at managing people. 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 how how big of a fleet can you manage And how effective is that fleet? Is that the new managerial skill?

48:40 Yes. I 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're just said the same thing. Yeah. We 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 apologise, but

49:00 There's still different roles in a company, right? Like you're you know, you're Think of like your sales team. Mike, 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 fleets of agents, or do you want them Talking to your customers and helping build those relationships and close that trust and all dah da.

49:20 For that role, I'm like, I think I kinda 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 sales leader. Or or like frontline sales AE like go manage these twenty reps that are gonna actually do the sales for you.

49:38 Can I switch gears for a second? How old are you? I turned forty this year. Okay, so you were If five billion dollars is your value. you were in the ballpark of being a under forty billionaire.

49:53 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 or success other than having a good time. Ha. I mean it the it feels Honestly it feels a little fictional to even hear you say that. Where I'm like, I don't I don't think of myself like

50:13 That way. Like so much is like tied to like the paper the paper worth of Zapir 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 I have some amount that's liquid. Describe describe your psychology around money. So how do you think about it?

50:32 How 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. Yeah. I think Look it's

50:44 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 Yeah, I wanna

50:54 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.

51:10 Wh 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 a million bucks. And you know, d do quite well. I mean shoot when I I when I was I remember when I just got out of college My my dream was if I could only make a hundred thousand dollars a year.

51:30 That was my dream. It's like if I could make a hundred thousand dollars a year, I I was like, Man, I'll be set. That was mine too, by the way. It was yeah it was like if I can get out and work at KPM G and get sixty grand, I might get to a hundred grand before I'm thirty, and then I am set, baby. Yeah. And I I don't know, like but 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 you do anything cool with your money? Uh you know, when I go to a restaurant I don't look at the

51:57 How much the items cost. Like. That kind of stuff. And so you've raised money, so you have to have some type of likely, presumably you're gonna ha you want to have some type of exit event, whether that's IPO or um Selling the whole thing.

52:10 Is there anything that you have on your bucket list that you'd wanna like if you're like, Okay, if I get over A billion dollars liquid. I wanna change this about my life, or there's something interesting I wanna do. No, there's there like N nothing that I couldn't already do.

52:25 You know, like I 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 can do that now. I don't need billions of dollars to go on a Savar. The reason I like asking you about this stuff is because

52:43 You are very well rounded. And you seem like We had this like joke called like the total man. It was like Like a buddy of ours or a podcast guest who is like Kind of like the perfect package. Like they were like

52:58 Ruthless when they need 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 um 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 no, I was really lucky. Like I grew up

53:32 you know, with a like a you know, a a family that was all sort of like you know, my my parents were married, my t 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 I I gotta talk about my granddad, like Yeah, my granddad's a World War Two vet But Yeah, well, I I d I didn't know him as that. I just knew him as this guy

53:54 You know, who w like always had time for his grandkids. He died as ninety eight and a half, and he basically l 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 un to until two weeks before he died. He did the New York Times crossword puzzle in pen every single day. And I remember going to You know, a after he died, we were at the um the funeral home and they were trying to like plan out all the stuff.

54:18 You know, most 98 year olds when they died, it's like they don't got any friends. There's nobody gonna be there because everybody who's uh 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 res you know the the receiving line or whatever will be You know, like we'll just do like thirty minutes or an hour or whatnot. And That receiving line is there for three hours. People just like coming through non-stop.

54:45 And You know, just m 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 It 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

55:08 Oh. You know, was was great at family. And great. At professional stuff. And

55:14 I just That that to me was like just a really good example of you know, someone who got their like prioriti like like dialed in really, really well. No, he didn't have it all, but he didn't need it all. It's like the things he cared about, he he he nailed them. And so to me that's always like stood out as like what

55:31 What a good life looks like. Sounds like a good role model. I think that you definitely seem to embody that where like Like I said, you are Great at business and also like don't have this jackass side that most people who are where you are seem to have right, Sean?

55:48 Yeah, yeah. We um I first I love that story that you just told. That was actually like a really awesome An awesome story. And also You know, I think that the value of what you just said uh you said two things I said out to me. You said he didn't have it all, but he didn't need it all. And I think that you know, I've been thinking about this a lot lately, which is that you're you're really only as

56:09 As rich as what you don't need. Yeah. Basically, like if you don't for you know that's whether that's material things or other, right? If you don't need the approval or 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.

56:26 Um right. Like you know, you don't have to go be s super flashy on social media because you just don't care for it. Um, and so I think that's like such an underrated attribute. And when you said that it kinda reminded me, it sounds like your grandgrandpa had that kind of that Way of life. You know. D s defining what winning is. So it's like if winning is just in the work

56:45 domain or winning is just in one you know, just in in in in one domain. If you have to kinda decide what it is for you and it sounds like pretty early on. You got clear on that. And then 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

57:08 you know, multiple divorces and your kids don't like it. 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 what I call one dimensional winners.

57:25 Michael Jordan. I'm a basketball. 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. 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 kinda have a A clear picture in your head.

57:51 It it it makes all future decisions really easy. Totally. I love that. Like, you know, define your own definition of winning. And Yeah, if you do that well, like some of your decisions might look odd to others. They'll be like, why 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

58:15 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 in the it's like what what is it that sort of like 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 wouldn't be that way.

58:42 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 raise 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 or what's the 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.

59:12 But that's not the point. Like the point is like the the the work itself. And I think that's you find that with anyone who loves what they do. Yeah, you ask'em I this is where I feel like the media gets a lot of this like narrative around billionaires wrong is they're like, you know, they're they're hoarding their money, they're doing all this stuff. I mean look, I don't know all billionaires, but I've I've gotten to meet a couple.

59:31 And you know Darmesh, Halligan, like you know, gu guys like this who I don't know, they genuinely just seem like They like what they're doing. And like They're gonna keep doing that, whether or not they make you know

59:42 A little bit of money or a lot of money? The 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. And when they made the money, they kept doing it. So it's 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 gonna keep doing it.

1:00:05 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're probably should be retiring. But they keep playing'cause they just love playing and they'll take the they'll take the Lesser contract will do all this other stuff because it's like I just can't, I just love this game. Like I love doing that thing.

1:00:23 So Sean, listen to this one time, I think in two thousand and maybe two thousand nineteen. Wade spoke at HustleCon in Oakland, California. And this was right I think before you raised your round. I I think but you were you guys were the hottest thing going. And you came and talked and I thought it was awesome. And

1:00:44 I don't know if you remember this, Wade, but you and I sat backstage For like Ten hours. And all the speakers would come and go and they would have to pass to this room. And I think I don't rem I don't 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,'cause it was kind of fun to have like, you know

1:01:07 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 were just we're Kinda staring at him. But I remember you sat with me, I don't know if you remember this, for like it was like eight or ten hours. It was like the entire day and I was like, Do you got somewhere to be? And you're like Nope, I just like being here. And I remember that you you doing that and it seems like you have a change where it was like

1:01:31 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 I don't remember it being eight or ten hours, but I do remember it. 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 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 I I'm

1:01:57 Almost certain I had a notebook of ideas that I sort of took back and was like, All right, we're gonna try this. We're gonna 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. Books, podcasts, whatever. My favorite podcast, I gotta give a shout out to the acquire guys. Like I I mean, this just ten out of ten. Like, you know, mo most of those

1:02:30 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 a 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 reta ones. So there's like a Like a cot 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.

1:03:02 As for a book, um I I recently finished this book Make something wonderful, instead of Steve Jobs like in his own words. That's a really good one. Yeah, I think Steve Jobs, he sort of he has like a larger than life reputation. This book is literally just

1:03:18 Emails, speeches Literally just like his own his own thinking. And it's sort of organized roughly cr chronologically. And so you get to kinda just see his progression of like, you know V one Apple

1:03:31 the Pixar years, V two Apple, and you kinda just see how he He changes sort of like over time. Sean, do you have a a book that you read recently you want to recommend? Yeah. Um There's a book called The Score. Have I talked about that here? C Tai Win is

1:03:48 The the 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 the fundamental premise of the book is amazing. He's so he's talking about like The power of a game. So he's like

1:04:01 Imagine a game, um You let's say we take uh Pictionary. We open up a game of Pictionary. Games are this incredible thing'cause they tell you What winning means. So they tell you the rules.

1:04:14 What you're allowed to do. They tell you the the scoreboard, so like how you gain how you win in this game and and like what your goals should be. So they dictate your goals, they dictate your behavior And then they s 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

1:04:30 charades to be great at charades, you're gonna have to be loose, you're gonna have to be highly communicative, you're gonna have to be a great team player, whether you're the guesser or you're the the actor, doesn't matter. But then let's say you play risk. It's like you're gonna have to be like ruthless, dominating. You're gonna 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 d 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 philosophy teacher? He's like, but then I discovered this leaderboard.

1:05:04 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 he's like, Oh, you got to get published. And he's like, Well, then I realized 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 to 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

1:05:37 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 gets 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 gonna 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.

1:05:57 We're not gonna 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 straight 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 and I think like Because I think

1:06:15 the biggest decision you make in life is what game you're deciding to play. And how that will shape the the next ten years or your own. The book came out like Six months ago. Yeah, so I'm 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 I think you if I had a guess, did you listen to Blake One Day Two as a kid?

1:06:35 I I did. Did you, Sean? I mean who didn't? Yeah. Uh I read the biography of The memoir of Mark Hoppis, who is one of the lead singers of Blink One Eighty Two. 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 to force myself to put it down when I was going to bed at night because I was like staying up too late. Dude, why why are m musician biographies so good?

1:07:01 There's no light more than whatever of musicians and comedians. What else do you have? The red hot chili peppers guy, Anthony Keetis Was that good? Long time ago. I I was like in college, I read this thing and I loved it. And he partying. Messed up childhood. So he was like riveting. These guys, they weren't really that messed up. Um, but they got really famous, like really fast and he talks about it and he's like You know.

1:07:28 A lot of I'm gonna this is really the chapter where I complain about fame and he was like Just joking. I love being famous. It was awesome. Like people come 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. Uh Mark Hoppas has a biography and if you want like the cliff notes. Fahrenheit one eighty two, I believe. But anyway, wait.

1:07:52 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. Alright, that's it. That's the pod. I feel like I could rule the world. I know I could be what I want to. I put my law in it like my day song On the road less 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 Battel 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 podcasts.

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