Why Humor Is the Most Underrated Sales Tool | Will Aitken

Will Aitken breaks down why authenticity—often expressed through humor—is the ultimate go-to-market weapon. He explains that humor isn't just about telling jokes, but rather showing self-awareness and adapting to your buyer's tone without losing your identity. True personalization requires a level of human effort that mass automation simply can't replicate. By doing the "last mile" of outreach, like sending personalized videos or picking up the phone, sellers can immediately stand out in an inbox flooded with AI-generated garbage. Ultimately, the goal of sales outreach isn't just to get a meeting; it's to uncover the truth, even if the truth is a fast "no." Aitken advocates for skipping rigid rules, like hiding pricing on the first call, to deliver real value to buyers immediately.

Discussed in this episode

• Why humor acts as a sign of self-awareness and helps cut through B2B noise.
• How to balance your authentic personality with mirroring your buyer's tone.
• The inherent danger of relying entirely on AI automation for cold outreach.
• Why doing the 'unscalable' work, like recording custom videos, drives replies.
• How to identify the root cause of poor sales performance instead of blaming symptoms.
• Why uncovering the absolute truth is more valuable than forcing a positive response.
• The reason blanket rules against giving pricing or a demo on the first call are outdated.
• How to prevent scope creep by auditing the entire sales process before engaging.

Episode highlights

1. 0:00 — Intro and why funniest people are smartest
2. 2:30 — Balancing authentic humor with buyer mirroring
3. 5:45 — Losing bad deals vs. winning the right ones
4. 8:10 — What is actually working in cold outreach today
5. 10:20 — It works because it's work: Video outreach strategy
6. 15:30 — Co-authoring Gap Prospecting with Keenan
7. 19:00 — Why any reply isn't a good reply: Seeking the truth
8. 23:45 — Uncovering root sales problems vs. treating symptoms
9. 28:00 — The danger of B2B SaaS tool fatigue and vibe coding
10. 32:15 — Debunking the 'no demo on the first call' rule

Key takeaways

• Humor shows awareness and builds trust.
• Mirror buyers without hiding your personality.
• Outreach works when you do the work.
• Seek the truth, not just a reply.
• Give buyers real value on the first call.

Transcript

Welcome back to another episode of the Bridge the Gap podcast powered by none other than revenue reimagined. And today, we have a really special guest with us. Probably the funniest person to ever join in our presence. It's Will Aiken, co-founder of Salesfeed, CEO of williaken.

com and probably the only person I know who's helped more sellers get better by making them laugh first. From going viral with cold call skills to now leading training strategy and keynote content for B2B brands around the world. Will has built a go-to-market platform on clarity, humanity, and maybe just a little bit of chaos, Will. So we're going to dig into what works in modern sales, where most reps are going to screw up, and how humor, if you do it right, not wrong, is probably the most underrated go-to-market weapon out there.

Will, thanks for joining, man. Oh, that was quite epic. I like that intro, right? Dale would say, you said that Dale was a danger, is the best thing you did.

That was pretty impressive. Listen, record it, take it with you, use it as your walk-on for any events that you do. I'm good with it. Uh, you don't even have to give me the credit.

We'll we'll we'll just let you take it. Heck yeah, I will. Thank you. Hey Will, thanks for joining.

So, one of the things Adam was just talking about is the funniest people in B2B are also the smartest. Um, so let's talk about tone a little bit. Why does humor like punchiness through messaging, sales messaging, flow through the best? Like why does that like break the barriers?

I think uh humor is a universal language. Um, there are obviously some nuances culturally, but I also think humor is often a sign of awareness and awareness sales sometimes as well. Um, so not everyone can do it, but it's also a sign that being funny if it's part of your personality that you're showing up real, and I think showing up real is a is is one of the things that cuts through the noise these days. So, less so humor, more so being yourself, it just so happens that I am sometimes funny.

I I think one of the things you just said there, not everyone can do it, right? Like we have worked with, like we had a client in higher education. Um, and one of the sellers was for lack of better terms, very, very, very regimented. Now, if this guy tries to get on a call and crack a joke, like it's going to be so obvious that it's fake.

And like, you're naturally funny. I'm naturally the loud, boisterous sales guy. Dale's naturally a little more low-key. How do you balance that while still stepping out of your comfort zone to meet your buyers where they are?

Because not every buyer wants like, listen, like Dale and I said this when we started R&R, like I might close a deal with my, you know, boisterous personality, but when we get in the deal, the buyer might just drive better with someone who's more mellow. How how do you find that balance? And stay true to yourself. I think uh you can it's not so much changing yourself, but it's just toning down to mirror, essentially.

Because not, you're right, every so often you jump on a call and you know someone's not going to drive with the sarcastic jokes and the and the and the playful banter. At which point, not going to just completely change who I am because that's just uh acting, it's almost like a form of lying. But I'm just not going to go as heavy on the uh the uh being not going as loud, let's say. I'm going to tone it down a little bit.

That's all. Um, because you're right, there are definitely opportunities where I've I've probably lost them because I've been a bit too much of that uh playful. That's true. Yeah.

But I also think that's good. Especially when you it's a little bit different when you work for yourself, right? Because when when you show up as yourself and you work and you work for yourself and you're the one who's going to be helping deliver on the services, etc. Well, then if someone's not driving with you, that's probably a good thing.

You've established that there isn't a fit. When you're selling software or or selling on behalf of another company, I think at that point you have to be a little bit more careful in how you show up. But still, be true to yourself, because otherwise you're just going to get tired, burn out, there's a reason why a lot of that comes from performative. Yeah.

Dale and I have had a couple of people that don't get our banter and they just look at us like, are you guys for real? Okay. Yeah, I think I'm going to go with the other guys. Who's the other guys?

Will, when when did you realize um, people would take you more seriously if you led with humor or even like respond to you? Like, when was that flip point for you? Hmm. I'm not sure that was necessarily a flip point.

I think uh you know when it's working because you got you got get a room full of Zoom people people a Zoom meeting full of people laughing and you know you're in a good kind of spot regardless the deal. Now, I don't think relationships alone close deals, but they certainly help because they get you faster to truth transparency and um people just being forthcoming with information is going to be helpful to you to establish fit quicker. Um, and and build trust quicker. Um, so when when it's worked, you can tell.

Um, you know, it's almost like and it also makes it a lot more fun. I think where it became really clear was when I was doing more more and more content and then using that in in in both my sales process and to attract new customers as well. Did you have sales leaders that were like, did you have sales leaders like, no, you shouldn't be doing that. I can't like, that's not the way we do it.

No, I've honestly since since I was I I think it was encouraged anything that's seen as a competitive differentiator. So I don't think I've ever had anyone slap my hand. I've definitely had a few meetings where I've been like, I've had the self-awareness and and coaching from others to be like, maybe that one wasn't the the time to use that that that joke or or do that. I'm also aware that sometimes being funny, as I've said, it's it's it's a it's a push pull, right?

So it's a balancing act. You're going to push away as many people as you attract, essentially. Um, there are definitely cases where whether it be in a sales process, I have blown up a deal for trying trying to be too cheeky. Um, and there are times where the stuff I put out online is probably lost me as many opportunities as it got me, but the ones it got me were really good fits.

And the ones that it lost me probably would have never bought from me anyway. So I want to go off script for a second. I think what you just said is really important. Like, it it might have cost you opportunities, but it won you opportunities, but there's this balance of remaining true to yourself, right?

Like you you probably and I'm probably similar. I'm never going to be the guy that's going to come in all buttoned up and perfectly prim and proper and never crack a joke and never curse and like, I I know my audience and, you know, like one of our partners does not like the cursing as much as Dale and I and like, I know when I need to tone it down, but like, I tell customers, like the only way that I am the typical CRO is I curse like a sailor. And if that makes you uncomfortable, generally speaking, I can tone it down, but if cursing as a whole makes you uncomfortable, I I'm the wrong person. If the funniness makes you uncomfortable, we're the wrong people.

So I love that balance that you call out of, you know, mirroring so to speak, but at the same time, remaining true to who you are. Because if you don't do that, it's it it it is lying. Yeah, I think I think um people get this idea of mirroring when it when it's been taught that you're meant to act like the other person, right? But I think it's more so just matching the other person but staying true to yourself.

So like the pace, the the language, the the the mood. It's more more those things. And you can still change all those things without changing who you are as a human being. I think.

There's there's a reason I have a collared shirt hanging in this room, certain clients I have to have it. Other clients you don't. You mirror. There you go.

I don't have And then and then you're like, why are you wearing a collared shirt? You look so weird. Yeah, this is why I accepted Dale's when I booked the call with Adam J. Very very very rare um that I put one on on the flip side.

It's very rare that Dale is not in one. Um and if you get Dale in person it's very rare that he does not have a sport coat on. Good to know. Good to know.

All right, let's let's let's shift gears a little. Let's let's talk about cold outreach, right? So all the rage, all the topic. And we now have filters and spam and noise and AI and AISDRs and you know, just load it into Clay and send out 100,000 emails.

What in your opinion is working in outbound right now that most people are too lazy, too scared or just don't want to try? So, although a lot of the problems are being caused by things like mass automation, I think there's still a place for those to help you speed things up. I just think most people misuse them. Most people see that, oh yeah, we'll use that for everything.

Um, I think I think that the thing that works really well for for myself and some of the reps I've coached is is just the things that that automation still struggles to do well, which is often times like video, in person, actually showing up. Uh making calls yourself, obviously. Like all those things are really where I see the difference between the the the folks who are struggling or average and the great folks. The people who are willing to to to to lean into the things that other people won't, basically.

But I think video is the probably biggest untapped opportunity right now. Every rep I tell to use video they're, oh, I'm uncomfortable. Well, get F'in comfortable. Stand out from the damn noise.

Yeah, I think uh it works because it's work is is is one of the things I've been saying lately. If it's like that it works because it's, I'm writing that down. Yeah, yeah, it's work, it works because it's work. I I don't know if I thought of that or it was a comment or something like that.

So. I'm going to give you the credit for it. I'll take it. I'll take it.

Yeah, 100%. Write that down. Give me one of those like uh images of a beach. It works because it's work, Will Akin, 2025.

Um, That that will be the post this week. I'm in. But but I think with cold calling and and videos especially and and showing up in person and and and getting FaceTime with folks, it it it's again it turns back to what we were just talking about about leaning on the things that make you you. It's really hard to do that with emails and DMs frankly.

So the more uh involved the channel is, the more the more you actually separate yourself against all the rest of the chaff. It's uh, yeah. It's it's interesting because I I like as we go deep into AI, I just find people taking the same lazy tactics that they've taken for like using SalesLoft or Outreach or like and they're like now it's just like, oh, look at this N8N post that someone put up and like, let's try to like replicate that and then all of a sudden, actually, um, Jake, our other business partner put up that uh, um, Replit actually deleted someone's production database and like, you know. So, stuff's going to happen like that that you have no no control over.

And so, it's just laziness. Hmm. I think that's it. And buyers can tell as well.

If you put zero effort into the the stuff that you've sent them or or reach out to them with, what makes you think they put any effort into reading or We we just fired an outbound agency that for a client literally their messaging was, you know, the equivalent of, hi Adam, because you're the CEO at Revenue Reimagined, I saw that you struggle from this, oh, and PS, I see that you live in West Palm Beach. Totally, like, like, What is it, 2021? Get it together. Garbage, garbage, garbage, garbage.

Yeah. So what's a thing, like, a lot of that stuff, like, you can be a little bit like, you can be a bit more forward with the with the product forward stuff when you actually put effort into doing the work. Like, if you send it to someone a video and they know it's you because you're outside walking, it's not some of those AI avatar things with the mouth that moves a little bit weird and a little bit. Like, no no offense to those, I'm sure there's a place for them.

I think it's probably not what people try and use it for, but you can be a you can get away with being a bit more up front because you're actually putting effort into the average, and they know it's for them because frankly, how could you possibly record 40, 30-second videos where you call out someone out and be a smiley human being, you know? Um, that's that's really the question that people have is, is this for me? So when you do things that can only be for them, and it doesn't mean personalizing and saying, hey, West Palm Beach, wow, nice. It's more like just putting effort in, and then people give you effort in in hearing what you have to say.

But to to your point, it's there there's different kinds of personalization, right? Like, I I absolutely think there's a place for AI to go scrape 10K reports and scrape LinkedIn posts and listen to podcasts and all of that stuff. And that has its place. That's very different than what you're talking about where I, even if it's 30 seconds, I took the time to show you that I'm a real human being, standing out, walking outside, hey, Will, it's Adam, just wanted to really quickly thank you for the connection request, blah blah blah blah blah, or connect accepting my connection request, blah blah blah, done.

That is much more real than, hey Will, I see that you know, you have these really cool mouse pads that I happen to have one of on my desk, and like something that everyone else can can can write. There you go. I mean, like, no everyone could write that because I've only sold 50 of them. Um, but you know, I only have 49 of them.

I think the AI and automation stuff is cool. It does have its place. I I I actually, in fact, when I send videos to people it's a step in a sequence for a list that I've built using AI. Because I want to make sure I'm talking to the right people.

And and and I still want to have the highest chance of of of that message actually resonating with them. So I'm still going to use all the 10K scraping and the lament, you know, job ad keyword searches and all that. But like doing the extra work with it after you've done that, like video, like actually making calls, right? That's where you're going to stand out.

It's really the uh, the last mile. Like, you think about like that last mile is like super important to ensure that you like are standing out from everybody else. Like it's the one, 2% that's that last mile that's going to do the work. And if you don't do that last mile then what the hell are you being paid for?

Yep. 100%. Well said. I'm I'm curious where gap prospecting came from.

Um, is that something like where you're like hanging with Keenan and you're like, let's do gap prospecting. Oh, it was it wasn't quite hanging with him. It took me a year to convince him to do it. Um, but, you know, a few years ago when I first got into to SAS sales, I I read Gap Selling, um, during my interview process and it did change a lot of the ways I thought about things.

I just thought it was a very well-written book that that was a page turner, which I can't say about a lot of the sales books I've read. Um, and uh I was going to write this thing anyway, uh frankly, don't tell Keenan this, but guys, it's on a podcast, but he won't listen to it. He's too busy. Um, but he wasn't my first pick.

I I was like, Jen, come on, Jen, just write it with me. We fucking have to. Jen doesn't read. So she didn't feel like it was true to herself.

All right. Doesn't read. You're my you're my rebound. Uh, do you want to do this thing?

And then uh he said no. And he was like, I'm not going to let someone else put their name on a book that I wrote. And he and he also had his question, he was also questioning the effectiveness of cold outbound as well, but he did some of his own research and then eventually I gap sold him on the idea, I guess. And uh he said he was open to it and then I committed to probably a year of work with him.

So. To my perspective, it helped me a lot. Yeah. How how'd that progress?

Uh, it's interesting. I mean, Dale's been writing a book for the past decade, so. Yeah. I think I think when there's two people, it's a little bit different, right?

You know how you feel about stuff. I think it actually makes it a lot better. Even when we disagree, it means that we come to a conclusion that is actually often times better than either one of us on its own. Yeah, cuz you live in a silo, like you're in this little echo chamber if you're trying to write on your own.

It's perspective, right? I think we could all do with some more perspective in our lives. Um yeah. Which is why I'm also like, be careful with fucking using ChatGPT too much too much because that thing you go to it for perspective and it starts validating every loving crap out of you.

Well, when you tell it, no, don't validate me. It'll just do what you want it to do eventually. Yeah. They're like, yes, you're great.

This idea is amazing. It's like, Oh my gosh, I'm amazing. And then you start a new chat and send it the same thing. It's like, this is kind of shit, all right?

And if you thought about this. I write this and then you're like, don't validate me. And it fucking flips 180, does a 180 and you're like, yeah, you're right, that's crap. Yeah, even with the don't validate me, like, it it it it amazes me that all of these, whether it's G P T, whether it's ChatGPT, Gemini, Claude, none of them can understand a couple of prompts in my opinion.

Number one, they don't always validate me and no matter how many times you tell it not to use those damn M-dashes, I I I could put it in all caps 17 times. I'm still getting the fucking M-dashes. I'm like, I like to like tone it a little bit when it does that. I'm like, what the hell read that back.

How many M-dashes? He's like, no M-dashes. I'm like, read it again. Really?

Really pets? It's like talking to one of my kids or like being like, teachers, you know, do you want to try again? You sure? You know.

Um, but yeah. Uh, point being perspective is good, and that's why I'm I'm glad I got Keenan involved in it and not just launched on my own thing. It would have been crap, frankly, by comparison. Last question on outreach, um, before we shift gears.

So, a lot of uh outbound agencies or uh outbound sellers or BDRs will tell you the goal of outbound, the goal of cold email is to get a reply. Any reply. How how do you measure what what is actually a good message versus, ooh, I got a reply. Uh, yeah.

It's it's almost like the the the meme of sales ops going, this sequence is amazing. It's got a 20% reply rate. And all the replies are like, I rate out of office and unsubscribe. Yeah.

I I got a 92% open rate. Because all the spam checkers opened your email. All right. So here's here's here's my take on that.

Objections and replies, even negative ones, are good when they are the truth. Right? Is that they they're not interested and that's the truth because they've got something in place that's actually working really well. They just do not have the problem that you help solve.

Awesome. That's still a positive response. That's still a positive result, should I say, right? Because you've you're essentially you've categorized, not a fit.

That's okay. Put them on the back burner. You've got more people to go after, right? Ideally.

Um, but the issue is, I think a lot of those aren't always the truth. They're just ways to get rid of you and hope that you don't message again. Same thing on the phone. Same thing when someone tells you, oh no, we have something in place.

Everyone's got something in place. Is it working? Did you even hear what I said? Or did you just have that little response ready for me the moment you picked up the phone and heard this might be a sales call, right?

Now, would you be cheeky enough to say that to someone of like, Dale, of course, everyone has something in place. I would say. No. I would I would probably say like like, yeah, I'd be like, yeah, I I I actually would have guessed that you would have been doing something.

Right. say send out invoices with, buddy Adam, right now. I hope you're sending invoices at least, right? If you weren't, I'd be really worried and probably wouldn't be a good fit for me cuz how are you going to pay for them for the software?

But a lot of people is is it that you feel like this is already doing it well enough? You feel like that's not an issue? Or is it more so that I've kind of got you a really rough time here and it doesn't matter what this is about. You just don't fancy having this conversation.

Like just to like, basically give them a couple of more options and get to the real truth, right? And if it's the ladder, that's okay as well. Like, shit, okay, cool. Is there a better time for me to call back?

What would you prefer for me to reach out to you where you can give this some time and thought? Yeah. Yeah. Love it.

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com. The truth is the goal, not a meeting, not a positive response, just the truth. You're up next, Mr. J.

No, I'm not, sir. Absolutely not. He's not. I'm I'm I'm happy to take your I'm happy to take your segment.

No, it's good. It's good. I I see you switching shit up. It's it's good.

People people forget to He's always trying to throw me under the bus, Will. Is there a dock in the background being changed right now? Like, shit. He said truth.

You're going to ask Matt how to lie. There there there is a dock of course of show prep. I did not change it. Hand to God, I have not touched the dock since we started.

Dale just I don't know, maybe he needs his glasses changed or something. Yeah, hold on, hold on. Okay, now I can see. Let's see.

Okay. that's actually way better. Yeah, take the glasses on, man. Make makes Adam look better, I'll tell you.

Right? Yeah. I have a I have a face for radio, Will. Yeah, that's why that's why the intro is is killer.

Um, what's the biggest mind shift that your clients go through when they, you know, forget that you're this world-class, you know, trainer that you're executing on? What's that biggest mind shift that your clients go through when they're like, I think I know everything that I have and then they bring you in to kind of do their training and then at the end of it, they're like, shit, I didn't know what the hell was going on. How do you get them to do that mind shift? It's funny because so often people come to me go, yeah, we need help with cold calling.

We need our reps to get cold calling. I'm like, oh you know, I think it's part of the thing if you're doing a sequence or any kind of multi-channel outreach, I'd be curious to see your emails. like, yeah, you can see them but they're great. They're great.

They're awesome. They're amazing. ever A plus A star, you know, the top of the class kind of emails. I read them like, these are the worst fucking emails I've ever seen in my entire life.

I don't know why I haven't cut them. Um, but that they're like, I I I feel like there's it's not anyone's fault. But like, it's also probably maybe trying to keep scope down as well sometimes. Yeah, we hear that.

You I I would say it's often almost always more than what they thought they needed. It's the biggest mind shift. And it only you only get that by asking questions, taking a look and then you can't just be like, yo, your emails suck. You have to be like, while I was taking a look at them and I had this thought here, like, for example, and then show them and they go, do you do you see how that would work?

And then like, just even showing often times, but it doesn't come from me like asking questions live on the course. It's often times for me looking afterwards. Yeah. And then that's great news for them and and for me, frankly, because it does mean a little bit higher scope sometimes, and it does mean that they get better results from the entire outbound idea instead of just one part of it that they thought they had the issue with.

It's very difficult. We have we have a similar challenge where it's like, why am I going to pay you X dollars for Y? And it's like, we're like, our sales process is okay. It's like, and then you get in and you're like, why do you have that stage there?

And where's your exit criteria? It's like the same thing that we get into and then we'll go in and we'll do an audit, cuz we've learned. We're like, we can't do a scope without like, we can't do our complete thing without an audit cuz your scope will just increase. Cuz when they find you're good, then they're just adding a bunch of shit to your plate.

You're like, hold on. Yeah, it's it's scope creep. They're going to throw a bunch of stuff for free, basically. And then you end up hating the work and then doing a half-assed job of it.

You don't like doing half-assed stuff. You want to do work you're proud of. Yeah. Um, another common one is like, oh, we just need help with outbound.

But then I find like, they're like, well, a lot of the outbound leads we book aren't qualified. And then I'm like, okay, why aren't they qualified? Let me listen to a call. And then I'm like, oh crap, what the hell is this call?

Right? And then it's like, there's always something else. It's never the one thing that someone comes to you with. And often times the other Is a domino effect.

more of an impact. Yeah. Yeah. It's a domino effect.

Have a clear how to ask a question of an outbound lead. They're like doing the classic qualification or just treating them like they've got all the interest in the world just because they agreed to a call from a cold call. I'm I'm convinced most of the problems people think they have are symptoms of really the root of the problem. The root of the problem is much deeper and once you once you fix like the symptom part, you're like, or you see the symptom part, you're like, okay, you're you think your problem is leads, but your problem is really workflows and HubSpot or something's getting overwritten.

Like it's so different. In everything. I mean, what what about the Dale? We had the customer in Will, this will resonate with you.

They were ready to fire the entire sales team. Sales team can't close anything. Every call they get on, they can't close. Listen to a dozen calls, go back, it's not a sales issue.

It's a freaking ICP issue. We're talking to the wrong people. That is a fundamental I won't even blame marketing. That is a go-to-market issue that needs to be looked at at a much higher level versus let's fire six sales reps because they can't close deals.

How about you put qualified people in front of them? Totally wrong as well. Like go in sometimes and like, oh, outbound just doesn't work at this company. We've got too big of a customer.

I'm like, how many like I just did an ICP map and it looks like you could probably sell to a few, you know, 20,000 customers fit your criteria. Like what do you mean you don't have enough customers? look at the emails and I'm like, okay, what kind of an even have you even given them? And they're like, well, we had this VP from X company who I won't name and they came in and tried outbound.

They hired six outbound sellers. No one did anything. I'm like, can I see some some of this stuff, please? And I'm like, okay, right.

Yeah, no shit that didn't work. Cuz it's straight from the 2019 playbook, all right? But like, the the the the willingness to just write something off because they tried something once as well is another thing I see a lot as well. And tried it badly for one.

Um like, imagine me going out and being like, all right, I'm going to be a pro league baseball player. And that swing and miss and swing and miss and swing and miss. You're out. I'm like, well, baseball's a crap sport.

Couldn't be me. Couldn't be me cuz I I I tried three swings up there. Do you see that guy? Didn't hit the ball once.

So baseball's a problem, not me. Come on. I love it. I love that.

What um, Will, is there anything that you've been asked to do like as part of scope creep at a sales org, um, that you've just turned back and said, nope, ain't going to do that. That's called some friction. Um, one of them was it wasn't, okay, I can think of two examples. Number one, I did a playbook for someone, they're like, can we make it pretty?

I'm like, come on. You can hire a designer to make it pretty. Yeah, yeah, yeah. Well, that's what I ended up doing.

I went and fucking hired a designer. I'm like, there you go, guys, well done. No, I was saying that, not you. I was like, here's 50 bucks.

But I hope you're happy now. The sales reps will never read this thing ever again because now it can't change cuz it's in a PDF. Their idea of a playbook is that you add and change it as time goes on as well. Like, come on.

Another one was um, most most scope creep issues are like I like to try and get those out of the way before I agreed to do work and that way, like, very clearly, if you if you do enough work up front, um, I think you can avoid a lot of those issues. But like, another one was like, oh, well we don't we want to do there was an issue where like a they wanted to do two separate two-day workshops, one in London, one New York for their the team and the pack team. And I was like, okay, two days. They're like, we want to do your one-day rate.

And I was like, I'm staying for two days. That's two days away from my kids. That's two extra days that I'm not in my office doing all the other work I have to do. Like, I'm going to have to charge more for that.

And they're like pushing back and they're like, oh, let's just do one full day. I'm like, you ever tried to keep fucking 20 people's attention for a full day. I think the two days are the right thing. You just going to have to pay more for it.

Come on, like, let's be realistic. Like, when was the last time you went to a full-day workshop and were happy at the end of it and not thinking about all the work that you just ignored for a day. There's a balance here. The thing is, the balance can just cost you some more money and that's okay, right?

Like, would you rather it be done well or or or just done quickly at a lower price. I love that mindset. We talk about that all the time. We're not trading time for money.

You're trading outcomes for money, right? Do you want it done right or do you want it done fast? And fast could be right, but you want it done right more than anything else. Yeah.

It's that classic uh slider thing that I I saw someone made it like a 3D printer one of like fast, good, cheap. Yep. Yeah, that was it, yeah. Um, and you can't have two without losing one, right?

Um, but the point there was just like I was just like, I'm not going to do it. That's all right. And then and then sometimes pushing back in that way shows like a level of respect because a lot of the other people they're talking to wouldn't have pushed back and they're like, they're just like, yeah, I'll do it. But like, I think that's that's also the benefit of just being in a spot where you just don't need any business.

Yeah. Like, don't need the business. Sure. I'd like to do a 50 grand deal there, right?

But I also I'm I'm going to be all right, you know. It's always good to flip it on on its head too. Like, would you do this work like if you had two days worth of work, would you do it for a day? Day rate?

Like, the answer would always be no. That's a great point. Yeah. So it's like, okay.

I don't why why are you why are you trying to why are you trying to nail me? Your guys are the one that have the problem, not me. Like, Yeah, it's it's it's it's like um I'm having some work done, I'm about to tell this how it's going to be weird to walk away from this room after being in here for so long. But um there's a drywall guy, right?

I'm getting him to patch some things and then I hold if I said that you I want you to get it done in a day for less because if he like, do you know that like drywall takes time to dry, you know? Like, no no no, you need to get it done in one day. It's one day's work, not two days. And he's like, yeah, but I'm not going to be able to sand it and then put another coat on.

I'm going to be like, just get it done. It's a great analogy. It would be like, no, what what I can do one coat for you if you want for less, but I'm not going to do the the it all in one day because it just won't work and it'll look like crap. So.

Well, let me ask you, so you you sit at like this intersection of content, tech, sales, psychology, I I I think you do a little bit of all of it and you you blend it all relatively well. What uh, what's a shift that's coming in your mind that most go-to-market leaders don't see yet. And and are going to be totally blindsided by? I I just I just think there's just the ball's going to drop at some point.

There's just too many solutions on the market. It's nothing that G T A teams can control. Personally, I don't think. Um, but I'm surprised every day that these things even exist sometimes.

Yeah, I'm I'm with you there. Is is AI going to kill the creativity or is it going to make it, you know, 10, 20X more important? My thoughts on AI I'm I'm a big user of AI, but I just don't think it's there yet, but I also see people vibecoding stuff and I'm like, this is better than a lot of products in that space that you just made this for, right? I think that that that has created a huge influx of solutions that's almost like highlighting how bad of a problem it is that there are so many solutions out there that just do like these one random thing that you didn't think was going to be a problem when you can actually go make this.

I think the the the challenge is that a lot of people out there are just not very aware. Like, we talk about this every day, like tech, vibecoding, all this this this great stuff. But like, a vet's office who need like a a vet time appointment management system to run all their their patients through. They're not out there going, I'm not going to buy vet CMS or whatever it's called.

I I don't I don't I'm going to vibecode it. Yeah, I'm going to vibecode it. They're not doing that, right? But but yeah, but but then like at some point that ball's got to got to drop, whether it's more they're getting more emails and the solutions are coming cheaper and cheaper and cheaper until until what now?

So I just think I think that I I think B2B B2B tech is an anomaly in itself because everyone's trying to get out in front of it, but you're right, like the blue collar working, even like a managed services, so we have a couple of managed service clients and they were behind in the tech game, right? They were in the GTM tech game, I should say, they were behind like no outreach, no sales loft, no like they didn't have any of the the shiny objects. And so actually Those companies still exist. Sorry.

Yeah, I know. They're the funnest to work for because you can immediately have results. You're like, yeah, I'm very confident we can we can do some big things with your business here, but. Yeah, so you actually jump like technology.

So like they're going from like more manual stuff all the way to AI. Like they're just skipping like a whole generation of of tech that that they don't need to have anymore. So, it's very interesting actually. I I think I actually believe that B2B tech is going to hurt themselves with the way they're doing things.

Because all this vibe coding and everything, look it, I've done a bunch of stuff. We were like some of our clients are asking for some things. Um, it gets it to a point, but it's not production ready potentially stuff. It's like, it will break at some point.

You're you know, blowing someone's, you know, production database away. Like, there's things that happen that you're going to you're going to struggle with even on the vibecoding side. Like vibecoding is only going to get you so far. You still need once again that that last mile to uh, to get the work completed.

So, I uh, yeah, yeah. I think that the things that I'd really like to see replaced are like the social media out there. But the the the issue with that is like the limitation is servers, huge huge databases, and that's that's probably not every man can every person can can just I just wish LinkedIn would be a better place than this fire garbage content place it's become. Yeah, I think that the real cause of that is the fact that the LinkedIn team doesn't have a fucking clue.

Yeah. Yeah. They're they're the most out of touch team, I think, in the entire world. Yeah.

Based on what's going on. Enough work for today. I I I'd like to call that a hot take, but I don't think that's a hot take. I think everyone outside of LinkedIn, if we were to all get on a call, in regardless of where you are on the influencer creator sphere, would say the exact same thing, who the hell are you building for?

Yeah, who the fuck is Like if you're going to go to build a procurement software, right? Let's say, you want to build like a vendor management software. Who what the hell would you be doing if you'd never ever ever had a conversation with a procurement person. Now, you'd have one on your fucking payroll, consultant, who's going to tell you, no, this is a problem that always happens to me, and I'd love a way to fix that, all right?

Like, but they're like, they're like, nah, nah, we know procurement people better than they know themselves. We got this, don't worry. Fuck it. Let's let's bring in like a, let's bring in a sales person to consult with us a little bit.

Let's try and build this for sales people. And then like, procurement's going to be like, what? No, I I need to see what how many vendors I have, when the contract terms are up. And and the sales person's going to be like, yeah, yeah, um, let's try and increase the spend in in the vendor, like, it's just going not going to work, is it?

Um, anyway. Okay, well, let's uh, let's you know, for some rapid fire? One one word answers? Let's go.

One word answers. All right. I don't know about one word answers. Less than less than ten words.

Let's try one word. We've never played that game before. Um, a couple of these may may have a couple of words, but what's a GTM opinion you're scared to say out loud? One word.

No. Under ten, under ten, under ten. No, I'm not scared to say anything out loud, Dale. You know, you know me.

I've got no fucking fear. Marketing sucks so bad so often. I love it. I I don't disagree with you.

Well, who's someone in sales that doesn't get enough credit? What's the one title that who who doesn't get enough credit? Probably a solutions engineer. If you need one.

I think a lot of people don't. They're just lazy. Okay, so going back to the LinkedIn thing, what's one piece of sales advice that should be deleted from LinkedIn forever? Hmm.

Let me just think, let me just go on LinkedIn and get some inspiration real quick. I haven't looked at it. I haven't subjected myself to the pain today. Um, just the entire idea that like you can't give a demo on the first call, you can't give a pricing on the first call.

Why is it the first call that matters? It's more so like don't do that until you understand them. I'd say. Because the criteria, not necessarily on which call.

I think that I think like the cool mindset is wrong. Sorry. Make sure this isn't coming across right. Call.

Um, because some people think I'm just saying cool like, you know. Cool. Cool. Yeah.

Uh, but car like, oh it's got to be on the first call, the first meeting, or the second meeting. I think that entire like idea is just stupid. Because a lot of the time these days on intro calls I don't get all the information I want. But I'm still going to share enough that they feel like they're not just being they didn't get anything from it as well.

Uh, sure, you can say, oh well, when I ask questions it helps them see the problem differently. Yeah, that's true to some extent. But also like they showed up for something. Like give them something to walk away with.

And then often times what I'm doing is getting text based straight away, texting them some mark questions I didn't get the answers to, which then makes them, oh, can we jump on another call between this and the next one? And then all of a sudden we're doing like a lot more, right? But I think this idea that you have to get it all done in one call and you shouldn't do this by that at that stage. It's it's not as black and white as that.

Adam loves this question. I get to ask every time we we finish up. No, no, you do the last question. No, no, no, hold on.

One one more first. One more first. Yeah. Well, you can ban one go-to-market buzzword forever.

What word is gone from the English dictionary? LinkedIn. It's not a go-to-market buzzword, Dale. I'm going to end my career, man.

I need this. I hate it, but I need it. It's like abusive relationship. Um, Let me just think for a second.

Blank led. Uh, just anything blank led. Product led. Product led.

Product led. Yeah. I don't fucking know. And just shut up.

It's the same shit. Just a new word. Come on. Please make it fucking stop.

You make me want to vomit. Um, yeah, you can't just like A A led sales. Like shut the fuck up, Will. Shut the fuck up.

Shut your fucking mouth, Will. Come on. This is just This is just spin again. Come on.

All right. Ask ask your damn question, sir. Dream vacation destination. Uh, you'd think that like we picked the number one episode and sent someone on a trip or something the way Dale asked it.

All right, let me just think. Let me just check some fight prices on uh, Skyscanner. Uh, probably like um, there's no reason why I shouldn't just go to that whatever place I say, but um, probably like Lapland, something like that. Or no actually, Somewhere in South America, somewhere mountainous.

I'd love to probably do like Kill him and Jar. Yeah, I did Killmanjar. Um, Africa's it's my number one. I I would I would love to do that actually.

That's what I probably a good one. Let me have a little bit deeper of a think, but I think South America, I haven't it's the the one continent I haven't been to and uh, Pretty cool. I just I just love to Prague slides are really cheap right now if you're looking at flights. Not not not that I was looking, but you could get to Prague for like 300 bucks right now.

you trying to lead my answer? You trying to lead the witness, Adam? I'm like, That's That's where we could afford to send you, Will, and that's awesome because we're going. And your two kids for flights to Prague.

We are we are we we we can send you to the Middle East. You might not come back, but we can send you. We need bachelor trips. uh, bachelor Prague.

I'll tell you so. Fast cheap and good. There you go. Will, Aiken, thank you for joining the show, my friend.

Thank you for sharing all this knowledge. Go check out Will, I believe, Will, you correct me if I'm wrong. It's williaken.com, right?

Super easy. For the time being, yeah. Ooh. Little tease there.

All right, sir. Thank you for joining. We appreciate it. I appreciate you too as well.

Always a pleasure.