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A
All of these, you know, people that have made their careers talking about methodologies that are 10 years old, they're going to go away. And I think it's going to be harder to find people that can speak on what the future looks like, because it's not all of the graybeards. It's not all the people that have experience. It's going to be none of those people, because they can't or they won't, or they aren't reinventing themselves. The only way to do that is get in the tool. I'm just a big believer that this is so different. It's an alien language and it's so capable that like, hey, Rev Ops person, go figure this out.
B
Yeah. And those people are going to be the ones that are sought out. And if you're not, you know, reinventing that, you're not going to be invited to the party, for lack of a better term. And. And I think it's very important to think about that. I don't agree with the whole, like, you know, you gotta do something doomsday sort of thing with AI, but it's where we are as a culture. Like, you need to get your shit together.
A
I've seen the pattern. And basically the pattern is that these people become AI natives, and then they leave because they're like, no one else gets it here. Because I'm trapped in this organization that thinks a 10% improvement, quarter on quarter, is going to work. And those people are like, I don't want to work in that place anymore. And so it's like, once you've had the Kool Aid, once you've experienced it, you can't go back. And it's really hard to work with people that don't see it, that don't feel it, that aren't using it, that haven't experienced it. Because you're like, why is everything moving so slow? You're listening to GTM Live, a podcast by Passetto.
B
Hey, Jordan.
A
Hello.
B
Oh, man. We're in the middle of the desert. You can't walk too fast.
A
I always walk as if I'm trying to get somewhere, even though I have nowhere to go usually.
B
So thanks for doing this with me.
A
Sure. I mean, I have to get home. So as a captive audience, we're at
B
Chili Palooza in New Mexico, which is Chili Piper's unconference conference, and Jordan is here, of course, and I said, hey, will you come back on the show? Because people, our customers, always talk to us about the episode that we did.
A
Oh, great.
B
And how much they love it. So. Yeah. So what's been going on with you?
A
Well. Well, I launched a new substack. I'm now in the top 100 in less than a month in the business category. I'm. Oh, we're gonna get run over by a car. Let's.
B
It's okay. We'll edit it out.
A
No, no, don't edit. People hear about Dangerous.
B
Yeah. Maybe I should give some more context.
A
No one records a podcast in a dangerous situation, so I think that it's not full mission on mission possible, but those are people that are getting rides.
B
We're using our feet to give some more context. If you hear background noise or not, we're at a remote resort.
A
There's going to be some audio engineers to do, like, the Lord's work, to make excuse. Like, there's some person that has, like, 300 headphones on that's going to have to make sense of this.
B
Well, we don't have a person that we paid to do that, so.
A
So, okay, you asked me what I'm up to. 100% of my job now is just talking to cloud code and teaching my clients how to do that. So that's everything.
B
Yeah. And you're, like, automating your brain.
A
Oh.
B
And yes, definitely want to hear more about the substack and the projects that you have going on. It sounds like you're productizing yourself more and more. Is that a fair analysis?
A
Productizing myself? Yeah. I mean, substack is powered by a wiki that was based on Andre Karpathy's LLM sort of wiki document that basically is designed to help you structure, organize your knowledge. Well, it turns out that every cloud code session that you have has a default retention rate of a month, and you can change that to be kind of unlimited. And since literally everything I do is captured because I talk to cloud code, that means that all of the context about the problems I'm trying to solve and the difficulty in solving them are captured. So I basically wanted to share that with people, and I wanted people to have the sort of whole history of what it's like to get inside of the dryer that is Claude code, because it's just an experience of tumbling around. You just kind of keep tumbling. So I wanted people to see, like, well, what are the outputs of this thing? And for the first time, as far as I've been alive, and maybe as far as I know that our biggest constraint now is our imagination when it comes to building things. And that's never been the case before. And so there's whole areas of exploration that just were never available to you because the effort required to make them come to life was just enormous. And that's kind of not the case anymore. And because it's not the case, we now our jobs aren't at risk if you feel inspired in what you do, because that inspiration will lead you to build things that you never thought possible, and that will make you unfirable. And I just don't think people have got there yet because they haven't played around enough with the tool.
B
Oh, yeah. Do you think it's a matter of, like, giving yourself time to play around with tools, or is it you actually just have to believe that you have something that's worth experimenting with, or you have actually a creative imagination? Because to be honest, I don't know that a lot of people will ever get there.
A
Well, I think that a lot of people are in jobs that they don't really want, they don't really enjoy. They don't wake up thinking, I get to go to work today. I was with someone a long time ago, and she talked about the Sunday scaries. It's like, oh, you go on Sunday and you're like, oh, my gosh, I got to go to work on Monday. And that's an awful feeling.
B
Yeah, it's a horrible, sinking feeling.
A
Yeah. And you can't get inspired from that place. And honestly, you're just in the wrong thing. You're at the wrong company, you're in the wrong job, you're doing the wrong things, like. And it's not a blame. It's just kind of how it worked out for you. And so. But that's the kind of beauty of this tool, is that you can go explore what excites you. It doesn't matter if it's your work, it doesn't matter what it is, and you can just start building. And that's the only way that I've ever figured out how to find out what you want to do in your life is to just go play around with it. And Cloud code is one of these weird tools where it's really intimidating until you get into it, and then it's really intimidating until you ask it to do something, and then results come out, and you're like, oh, my gosh. And so, like, I kind of think there's sort of two categories of people in B2B SaaS. There's 80% of people that are just like, I don't want to be here. I don't really want to do this. I never really enjoyed this in the first place. I just, you know, couldn't make money running a horse stable or something. I don't know. And then other people are like, I want to do so much more and I'm constrained. And those are the people that are going to do exceptionally well. And the other people are going to have to find the thing that excites them.
B
Yeah, well, that's really eloquent way of saying that. So I love to talk about sales and prospecting, and we talked about that a little bit.
A
Sure.
B
Last time we were on. So I feel like we still see so much all the time that prospecting is just. You're kind of just like out there. And, you know, we talk to marketers that are really don't know the volume of the prospecting efforts that are happening. Right. This. The like, AI Clay, there's like, seems like a really big divide between agencies, you know, that know how to execute on that well or go to market engineers to execute on it well. And then there's everybody else. And we had a customer asking us the other day, like, we're all in on SDRs. And then they see the volume and just like, what the team is wasting a bunch of time on, and they're like, well, what do we do with our SDRs if this isn't working? So maybe not just focusing on SDRs only, but what do you think is the role of. What are sellers not doing when it comes to prospecting?
A
Well, you kind of have to go back and trace what the customer cares about and the situation that the customer is in. And that's the thing that I think no one does. We are so focused on us. And there's a really easy test here. You just look at your message and you do two things. You say, would I reply to this if I was the prospect? That answer is usually no. And the other test is what percentage of this message is about me? And what that means is that you don't understand the value that you provide your customer and the situation that the customer was in to need you in the first place. And so the question, like, hey, we've hired these SDRs and we don't really know what they're. We don't really know what they're doing. We don't really know. We're not really getting a lot of value out of them. The reason that that is this seems like a problem that is both recent and indefinite, like it's been around forever, is that we never really gave them any insight in the first place. We just hired a bunch of them and said the ones that could figure it out are the ones that got to stay. And we never knew how they figured it out. We didn't really understand why what they were doing. It's just like, you're making your quota. We're not going to ask questions. But the beauty of these tools is that there's like three levels of trust. The first level of trust is what's in the CRM. The second level of trust, which is a higher level of trust, is what the customer said. But the best level of trust is what the customer did. And so when I start with my customers, the very first thing I do is like, I don't actually care at all who you think your customers are. I don't care what problems you think they have. I'm going to compile, I call them dossiers. I compile customer dossiers, which is a timeline. It's in a JSON format, which is just allows me to charge more money because I can say the word JSON. It's a CSV, it's a fancy CSV. And it's every single interaction that the customers had on a timeline. What the CRM was updated and when, what they said and when, the full transcript, all the speakers labeled what they did in the product and when. So that what you do is you say, when a customer came to me, what did they say? And you divide this by closed one, closed, lost or churned. And you basically just say, well, what are the customers that are successful do and say? And what are the customers that unsuccessful do and say? And then all you do is you ask the model, how could I have determined that before they ever came in my door? And the models are great at this. It says, well, these are the situations the customers are in. Here's how you could have known publicly. And suddenly if you do that, the only thing that you're ever doing is you're just telling the next person why the last person bought you sort of in this situation, you know, it's like you had just filed the New Mexico business entity and you're in Delaware, but you're gonna have to manage taxes in New Mexico. And most people get this wrong when they do that. And this is the problem that they were struggling with. So that's everything. That's the whole kit and caboodle. But now we don't have to rely on STRs like testing. We just can take our customers words and actions and come up with like reasonable hypotheses.
B
Wow, that's Amazing. Thanks for that. Feels like you can be so much more effective with so much less. And I wonder if that's potentially also trips people up because you're just used to just making it feel so complicated having to do so much.
A
Well, I mean, the thing is, this is all. I don't know if you look a lot of like LLM outputs and it's like an ungodly amount of information. Usually it's like, oh, look, now I can tell you everything that this company has ever done. It's like, so what? What am I going to do with that? And so in many ways the large language models have made our job harder because we have to sift through more golden garbage. But the way that I think about this is just that I don't know if what I ship is right, but you can test it. And so when I do this with customers, I usually bring on a cold caller. If I'm selling them campaigns, I bring on a cold call and I'm like, my guy will reliably make a hundred to $200 a day and I'll know if I'm wrong by day two. So the cost of getting it wrong is so low. It's like, okay, well, yeah, maybe he targeted the wrong person or. And the large language models make a bunch of mistakes. But there's a great VC that said this to me the other day. It stuck in my head. He's like, you can beat every grandmaster in chess if you get two moves for their one. And I think that we just need to start thinking like that, which is like, if we can launch campaigns at such a higher velocity, like high quality hypotheses at much higher velocity, well, suddenly we can get things wrong faster and eventually we'll stumble on what's right.
B
Yeah, that makes sense. It's the high quality aspect, you know, that I was thinking of earlier. It's not that you're doing more, you're being more effective because you have higher quality. And when you're putting it out there,
A
I mean, I would say higher quality is such an interesting concept because I don't know, like, I would say you have a higher velocity of like above average experiments. So it's not that any given experiment is like a hundred x better, it's that you can do a hundred of them at 30 to 50% better than what you would have done in the previous world. And so the large language models will still get a lot of stuff wrong. It's like, ah, this title is wrong. And. But it almost doesn't matter. Or for this particular case, because your reps will know it immediately and you just update it. So, like, I had a customer and they called and they said, hey, you've given us all these accounts, but we found that we can find much better context if we just search the web. And I'm like, okay, tell me where. Tell me where are all the websites that you're finding this, like, how are you doing it? And they gave me 50 of those. And so I just said, yo, Claude, like, go take all this and update everything in the total addressable market. And I shipped them a new list the next day. And so the consequence of me not providing the very best list on day one is, like, low, because on day two, I can do that again. And so I think that we just need to think about, like, we're just going to exist in a world that's going to be a little sloppier, right? It's like, you've probably seen this. A lot of your software, like, LinkedIn's been, like, buggier for me. And I think that we're just going to live in a world that's, like, not as polished. And the way through this is we have to adapt to. Ship things to customers and try. And I'm not saying, you know, throw the customer under the bus, but what I'm saying is that if reps call and they call 50 of the wrong people because the script didn't match the phone numbers in the row, who cares? Just fix it tomorrow. And we have to get used to that. That motion.
B
Yeah, thanks for that. So I don't really have any more questions at this point. I feel like we've done it.
A
I know we've answered all the.
B
I know it's getting late, but how do we find your new substack?
A
Yeah. Edge.blueprint GTM.com. i have a tier that I'm publishing basically daily, and I've got a tier that has all of the. Like, how you build this. And then I have another tier that's yearly. That is, it's me in your terminal, and I passively watch what you're doing. I mean, me, like, I'm not. I don't. I'm, like, not seeing you. It's a tool. It doesn't submit anything to me, but it listens and it queries. And if I have a piece of knowledge or a skill or a tool or something I built, it will say, hey, Jordan has an opinion on this. Do you want to pull it in? And you can also do this sort of on your own. And the whole goal is that as I build things, I want to make them available to people. Right. That in, you know, we were talking a while back here, but like, in the world where the distance between imagination and action is so short, the thing that will be irreplaceable is trust in someone. It will be like, you know, we trusted in news organizations or something. And so I'm not too worried about giving away everything I've ever done, because the reputation is irreplaceable. And so that's what I'm attempting to do.
B
Yeah, well, I appreciate it, and I think a lot of other people appreciate it, because even getting from zero to one is one thing, right? And then you release the knowledge about that. But then knowing, okay, so what, like, what am I going to do next? Or it's always something that's going to be a living and breathing thing. So.
A
Yeah, it's a good point. And so what is a great question. Because the thing is that I told this joke earlier that the creator of cloud code was reading a job description that said, must have 5 years experience in cloud code. And he's like, I'm not qualified. This is not five years old. And so I think that we just kind of need to remember that. That, like one of my clients said to me, jordan, I've always felt I've been on the very bleeding edge my entire career, but not now. That's why they hired me. And what I would say to that is that you can't learn AI. Like, that notion is, like, a little silly. I think you can do AI, and if we don't think, how do we master this thing? Because it's just an impossible. That's like saying, how do you master getting to know someone? It's like, you don't. You just go at it and you ask good questions. And so you just do AI. You get into it. And I think that the thing that people would do well with is to increase the scope of their imagination and just ask and see what the robot can do. And that's it. There's nothing else. There's nothing behind the curtain. There's no. Just like, don't believe these people online that say, like, oh, I built this thing. And it's. You can't replicate it. It's like everyone can replicate anything. There are some people that are better at it, but the delta between the people that are amazing and the people that are bad is surprisingly small. Like, it's.
B
It's a small number of hard skills. The rest of it is more an approach to your work, an approach to problem solving and thinking, not so much a hard skill.
A
Yeah, yeah. It's not, you know, it's like, if you, like, want to ride a horse, there's, like, a lot of things that are like, you got to, you know, there's the horseshoe and then you got to, like, get the saddle and then you got on the talk to the thing and, like, that's a world where you could be much, much, much better riding a horse than someone else because you have practice an ungodly amount of time. AI is weirdly not like that. It's not like that at all. The difference between the person that's really good at riding the horse and the person that's not is just how complex is your thinking. That's it. There's no. There's nothing else. There's nothing else behind the curtain. And so we just need to let go that this is unlike anything else ever. Right. You're just asking for an output and it's going to come back and it's going to be amazing, but not nearly as good as you want it to be. And ask again. That's the whole enchilada that people need to just. You won't get better at it because it's just your thinking. Like, that's it. There's nothing else.
B
Yeah. Well, thanks for doing this.
A
What do you think? What are the odds that this will come out?
B
I think it depends on the audio quality, so we'll see how much that came through.
A
But let's talk to the audio engineer here. If this. This is a show for you. If this is like, it's like midnight and you're like. It's like crunching and I'll just do it again. Just don't. Yeah, there's probably how. You got an audio engineer.
B
Yeah.
A
What's the story of that guy? That gal?
B
They'll probably just cut all the punchy parts or they'll say, this is unusual. I don't know. I'm not an audio engineer.
A
Okay. Well, we should, because they're going to listen to this. Actually, it'll be really unfortunate if they listen to this at the very end because then they'll be 90% done and they already will have spent an ungodly amount of time. They're like, son of a.
B
If they ever get through it. But.
A
Yeah.
B
Thanks for going out on a limb as always. Yeah.
A
Yeah.
B
What did you think about Chili Palooza? Any words on the event?
A
No.
B
You had to be here.
A
I think that the bar to create a really great event is only getting higher because digital channels are saturated. And I will say that if you can evoke a feeling in your buyer that that is the thing that will make all the difference. I totally, I probably shouldn't say this, but I'm a little embarrassed. We could cut it later. I said, I'm embarrassed. I'm here. I don't really know what you do. And it's like, well, shit, that sucks. You know, we're here gathered from someone that I immensely respect. And she's just gotta be one of the top builders, AI builders and thinkers. And I think that to thread these events is going to become harder and harder because of the speed that everything moves at. And I think that you're just going to find a few number of people that have an outsized, valuable view to the world. And that's not going to be democratic. Like you're going to want to listen to the 10 people. And so all of these, you know, people that have made their careers talking about methodologies that are 10 years old, they're going to go away. And I think it's going to be harder to find people that can speak on what the future looks like, because it's not all of the graybeards, it's not all the people that have experience. It's going to be none of those people because they can't or they won't, or they aren't reinventing themselves. The only way to do that is get in the tool. I'm just a big believer that this is so different. It's an alien language and it's so capable that like, hey, rev Ops person, go figure this out.
B
Yeah. And those people are going to be the ones that are sought out. And if you're not, you know, reinventing that, you're not going to be invited to the party, for lack of a better term. And, and I think it's very important to think about that. I don't agree with the whole like, you know, you gotta do something doomsday sort of thing with AI, but it's where we are as a culture. Like, you need to get your shit together.
A
I've seen the pattern. And basically the pattern is that these people become AI natives and then they leave because they're like, no one else gets it here. Because I'm trapped in this organization that thinks a 10% improvement, quarter on quarter is going to work. And those people are like, I don't want to work in that place anymore. And so it's like, once you've had the Kool Aid. Once you've experienced it, you can't go back. And it's really hard to work with people that don't see it, that don't feel it, that aren't using it, that haven't experienced it, because you're like, why is everything moving so slow?
B
Yeah, well, I was wrong. I did have more questions, and thanks for opening up about that. All right, we'll let you go, Jordan.
A
All right. Later, Sam.
Episode Theme:
A candid, thought-provoking exploration of how “AI natives” are disrupting traditional Go-To-Market (GTM) roles, methodologies, and mindsets—specifically how tools like Claude code reshape what’s possible for B2B SaaS sales and marketing. Jordan Crawford shares raw insights on productizing expertise, shifting job roles, and how organizations and individuals must radically reimagine how they work, learn, and build in the age of AI.
Timestamps: [00:00]–[02:21]
Timestamps: [02:22]–[05:28]
Timestamps: [05:28]–[07:30]
Timestamps: [07:30]–[11:55]
Timestamps: [11:55]–[15:30]
Timestamps: [15:37]–[18:46]
Timestamps: [18:46]–[19:49]
Timestamps: [20:16]–[23:22]
“For the first time… our biggest constraint now is our imagination when it comes to building things.”
– Jordan Crawford [04:38]
“The only thing you’re ever doing is you’re just telling the next person why the last person bought you in this situation.”
– Jordan Crawford [11:04]
“You can beat every grandmaster in chess if you get two moves for their one.”
– Jordan Crawford quoting a VC [12:57]
“You can’t learn AI… Just go at it and you ask good questions… There’s nothing else behind the curtain.”
– Jordan Crawford [17:37]
“The thing that will be irreplaceable is trust in someone… reputation is irreplaceable.”
– Jordan Crawford [16:36]
This episode is essential listening for B2B GTM leaders and operators looking to thrive—and not just survive—in the era of hyper-adaptable, AI-powered selling and marketing.