AI-Powered Seller

Authenticity in the Age of AI

• Jake Dunlap

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In a world where every seller is told to “automate everything,” how do you stay authentic? In this episode, host Jake Dunlap sits down with David Abbey, CEO and co-founder of Endless and Penny AI, to explore the future of human connection in a Gen AI-powered sales world.

David was building AI solutions long before it became mainstream—helping sellers and creators strengthen relationships, not replace them. Together, Jake and David dive into what it really means to balance automation and authenticity, where AI adds value (and where it destroys it), and why being “more human” might just be your ultimate competitive advantage in 2025 and beyond.

You’ll learn:

  • How AI can surface insights to make your interactions more personal and meaningful
  • The red flags of “too much automation” and how to avoid losing your human touch
  • Why the future belongs to sellers who master context and creativity
  • How influencer marketing and digital avatars are reshaping trust and communication

Whether you’re a rep looking to up your game or a leader rethinking your team’s AI strategy, this episode is packed with real talk, tactical advice, and future-forward insights.

Tune in to learn how to use AI to amplify authenticity—not replace it.

SPEAKER_01:

We all have our battle scars from dialing for dollars and sitting in like a wet room back in, you know, 2000, just like somebody pick up the phone. I I think that's gonna be a lost art. I just don't think people are gonna get it because they're just gonna find these cheat codes and be like, well, I've got an ICP that has three or thirty thousand customers. And what's really cool is if you use an AI to say, I've got thirty thousand customers, go give me a battle card on Jake and help me craft a message that's unique to him. I think there's value in there, but I think it still has to come from you. AI-powered selling.

SPEAKER_00:

Every seller today is becoming more and more terrified of the same thing. And that is becoming less and less human and being asked to be more and more of a robot. And let me let me tell you this, my friends, buyers can tell, and they are begging for you to be authentic. And that is why I am super excited for today's episode of AI Powered Seller. Uh, today's guest, Mr. David Abbey. David, CEO, co-founder of Endless and Penny AI. Um, this guy was in the AI game before AI was Gen AI, right? So he spent the last decade at the intersection of technology, social commerce, AI. And what I love about this conversation we're gonna have is David also deeply understands sales and deeply understands what it takes in 2025, 2026 to be successful in creating authentic communication. So in today's conversation, we are gonna go deep on like what does authenticity even mean? You know, he we'll talk about you know digital avatars and you know, they they do influencer marketing. So, what does the future of that look like? We're gonna talk also about more tactical day-to-day use cases of hey, where should I 100% be using AI to create more authentic interactions? And also, where should I stop? Where are those red flags? So let's jump into it. I'm excited for the conversation today. It's gonna be a good one. You're gonna want to get out your digital notepad or your pen and paper because today's episode is gonna be a fun one. All right, David, welcome to the show, man. I'm looking forward to the conversation.

SPEAKER_01:

Thank you very much, Jake. I'm uh yeah, I've been looking forward to this as well. I'm excited to be here.

SPEAKER_00:

Yeah, this is gonna be a fun one. I think this I, you know, we're in this very AI era, obviously, for all of you tuning in. That's why you're here is to understand, you know, what does the future look like around Gen AI? Uh, how am I gonna use it tactically in my role? And I think, you know, today's topic around authenticity, right? And what it means to be authentic authentic. I think we're gonna, I think we're gonna have a pretty good conversation here, as many people I know are somewhat struggling with this, I feel like, this concept of like, am I cheating? You know, or is this, you know, like where does authenticity begin? Uh, I think is I don't know if the line's blurring or something like that. I I you know, I've got some feelings about this, but I want I want to start with you. Some feelings about it as well. Yeah, and like what got you into this? You know, what got you into this? You know, you've built two companies now with you know, Penny and Endless. You know, um how did you what got you into this? This kind of automation versus authenticity challenge, you could say.

SPEAKER_01:

Uh my wife, actually. Okay so uh Penny AI is a company, um worked uh exclusively in the direct selling vertical. Um so multiple marketing, so think Tupperware, New Skin, Avon, Arbon, Damway. Um, and it was when my wife and I, we had three kids in diapers, and she was working with uh a company called Rodan and Fields.

SPEAKER_00:

She's she's a uh yeah, I remember that one.

SPEAKER_01:

Redanana Fields, Dr. Rodan and Dr. Fields, like brilliant, brilliant people. Um, my wife is a nurse. We had three kids in diapers, so she couldn't work, so she started that business. And it was actually watching her try to build relationships in a scalable way while being a new mother three times over. Um, and she literally said to me, David, I need you to build me something that tells me what to do. And uh a good friend of mine, Chris Noble, who's our my my co-founder and and CTO, he uh had ran the labs and innovation team at Hootsuite. He understood social incredibly well. Um, he brought in one of his partners from Hootsuite, a guy named Andrew Draper, who had been in the e-commerce and D2C space going back to the beginning of D2C. Um, and the companies of those sizes have so much data that they're sitting on, like Randonfield specifically. Um, but their distributed workforce is a volunteer workforce that is working off not even the side of their desk, they're working in moments of time. And when you think about that authenticity question, it's like someone is trying to build a personal relationship to sell them a product, whether it's a you know, a uh a regular business, a car salesman, or in the in the direct selling industry for Red End and Fields, where AI really comes in to create the opportunity to be authentic is the speed of access to information to be authentic. And that was the whole premise. So my wife's name is Terry, massive customer base, couldn't keep track of it to save her life, wanted to have authentic conversations. And what we did, and this was the big data machine learning era back in 2017, 2018, is how can we surface the information that we have uh vis-a-vis from Bernan and Fields to tell people what to do every day and give them information so that when you know Terry reached out to Jake, she's quickly able to look at his order history. She can look at her notes, like a pretty, you know, the the fundamentals of a CRM, but doing it in a daily way. And Penny was the name of the company, Penny was your virtual assistant, Penny would tell you how to do this, Penny would link and sync with your social network so you could easily gather information. And that's where it started. And it started with my wife, and within um I I think a matter of months, we had tens of thousands of users because we solved a real problem. Because that vertical, the direct selling vertical, people either love it or hate it. And the people that love it, love it, and there's a lot of them. Uh, they had a problem. And we were, you know, we kind of hit the nail on the head. And from 2018, all certainly all the way through the pandemic, um, we solved a very serious problem because people genuinely want to have great relationships. It's the access to information at scale that makes it challenging. And that's where I think AI is brilliant, is it can just surface the right information to be very meaningful.

SPEAKER_00:

Yeah, I mean, like I think that's where a lot of this starts is, you know, we're trying to actually that's a really good note for people to think is that, you know, we use this word, I think, AI and automation in a lot of the same sentences, but you know, when used correctly, what we're really talking about is using AI to have better relationships or strengthening relationships and you know, surfacing things that it's not that you couldn't have found this information, it might have been public or sitting somewhere, but you know, it just pulled it together faster for you. And I think a lot of yeah, exactly. And I think a lot of people, um, I think that are struggling with AI adoption are just so used to having to just figure it out themselves. And, you know, so then as they start to think about this automate human combo, I think they struggle with it. And I think this is a good kind of follow-up here is, you know, when you think about Penny first, right? And we talk about that, you know, how did you think about, and this is before like Gen AI, right? So Penny was, you know, ahead of its time.

SPEAKER_01:

This is before Gen AI, yeah.

SPEAKER_00:

You know, uh for this stuff. How did you think about that? About, and and even, you know, feel free to extrapolate to today, too, where what are the things that, you know, you think about automation? Obviously, there's things like research, pulling together data. I think most people are like, cool, I hate research, I hate pulling together data, right? But how do you think of that things that people should not be trying to automate and keep, you know, human only or human-assisted?

SPEAKER_01:

I think my one comment there is I've seen a lot of people, and myself included, be burned on full autopilot AI. Um, where I was just like, oh my god, like head in the hands, like, okay, I gotta turn this off. Um in the going back in penny, you've got to think of uh anyone in the direct selling vertical, they are a one-man army and they have to run every aspect of their business. So we automated as much as we could without ruining um the relationship. And one thing we took a stance very early on in is we are not going to be an um email blasting solution. We are going to integrate directly with LinkedIn and Twitter and Facebook and Instagram. And if you want to message someone, we even got to the point when Gen AI started coming out. We would recommend content that you could say, like scripts. We could recommend content you could share, but we never allow people to blast it to everybody because that ruined authenticity.

SPEAKER_00:

100%.

SPEAKER_01:

We would be like, here's Jake, here's why you should talk to him, here's what you could say, but you can't send this to everybody. And that, but we got them all the way to the line, and then we're like, now it's on you to go and have this one uh one conversation. And we got it so many times from our users, they're like, Thank you so much. Like, you knew you recommended I talk to this customer I hadn't spoken to in three years, and I forgot. And I reached out to them on Facebook. And when I opened up the Facebook, and the cool thing is when you go in and have a one-to-one message with someone, those apps do such a great job of indexing your entire history with that person. And they just be like, I jumped in and I instantly realized, you know, this was such a great friend of mine, and I just lost track because I had been in the hamster wheel trying to build my business. And we always want to get you as far as we can, but we didn't want to take away the human connection of it. And we used as much access to information as we could to make you do that more efficiently. So my wife's classic line was when I have five minutes in the high school pickup line or in the school pickup line, she can open up do something that is meaningful that drives her business forward. And in the the the topic of authentic authentic ways, hey Jake, it would, you know, I haven't talked to you in a while, but we would be able to serve her information to be intelligent and be accurate.

SPEAKER_00:

Yeah, I think again, that's where I feel like outbound today, I mean, in particular, right, is the lack of that. I feel like there's almost just a lack of like reality or appreciation of understanding. Like, no, no, no, like the human has to be in the loop here. Now, if you're just doing some blanket approach, it's a transactional sale. You know, I can make an argument that, you know, some of the outbound AI or automation stuff is is could be more applicable, you know, potentially. But I do feel that it's not, and I say that from personal experience.

SPEAKER_01:

We tried um two of the you know, venture-backed uh, you know, digital workforce uh employees, and they I haven't seen a piece of software saw fall that flat on its face that quickly, and it's not there, it's not there at all. I I saw one of my LinkedIn messages, and it's like, hey, something about me going to their church and a fellow, you know, right or something, and I was like, what is happening here? And they except to my LinkedIn, right? Which means they obviously didn't look at my profile. But it was just the hallucinations were so far out there, and I think a lot of people are it's a cheat code, but I also think anyone coming into B2B sales and outbound sales, like we all have our our our battle scars from dialing for dollars and sitting in like a sweat room back in you know 2000, just like somebody pick up the phone. Uh I think that's gonna be a lost art, and I just don't think people are gonna get it because they're just gonna find these cheat codes and be like, well, I've got an ICP that has three or thirty thousand customers. Send.

SPEAKER_00:

That's right.

SPEAKER_01:

What's really cool is if you use an AI to say, I've got 30,000 customers, go give me a battle card on Jake and help me craft a message that's unique to him. I think there's value in there, but I think it still has to come from you. That's exactly right. I'm all about e-codes.

SPEAKER_00:

Yeah. Well, the funny part is like it a lot of it's not really a cheat code if it sucks, you know, with a lot of these things. Like, I think I think people think that they're they they think that that they're a cheat code, but you hit it on the head, man. And we're, you know, we do a lot of generative AI deployments for our clients. And, you know, that's a lot of what we say is like, look, let us get you to the point where I've got like some amazingly relevant piece of insights. Like we've got a client um that uh does website speed um optimization, right? And so let's use AI to go and scrape the, you know, scripts that are running, highlight the two or three that, you know, what a rep would have had to go inspect Elements. They would have had to go try to think about what are the two or three that we should optimize. And then you turn your brain on. And here's the template, and it pulls in this part for you, but then you've got to say, oh, okay, it's not apparel, it's not that type of apparel. It's actually fast fashion apparel. And this thing is why we're relevant to fast fashion versus athletic. You know, I'm just like making up an example. But I I I think that that is where the the teams that are winning and outbound are either just, you know, they're smaller companies that just torch their TAM initially because they're like, forget it, we'll figure out how to get to 10 million or 15 or whatever it is. Um, and then they have no sustainable way to continue the growth. Or is the company doing what I just mentioned? That, you know, they're the fi the fire, you know, the the the the flamethrower approach can only work to a certain extent. And then you have to be able to have people turn on their brain if you want to win.

SPEAKER_01:

Um Yeah, well, unfortunately, we're all getting dumber because of AI. That's a fact. Uh, I feel it every day. I don't like I'm a very passionate chef at home. I just use ChatGPT now. How do I make this? I don't even think about it anymore. But the I think the companies that are gonna do really well is that you instead of torching your TAM, and this is where we've we've been testing the iterating messaging nonstop because endless is still a relatively new entrant in the influencer commerce space. Um, we are taking sets. You know, hey, here's X number of companies. We're testing this language and the but we're using AI to write it all. We're you know, hey, this is the ICP. We're getting the AI to do a full breakdown of the ICP with the messaging, the value proposition, and the business objectives that our reader is going to be going after. Let's test this messaging. Okay, this kind of worked, these things hit. Now let's do V2, V3, instead of just everybody we are being very methodical in our approach, but the speed at which we can do it that's right, um, is completely ridiculous because yeah.

SPEAKER_00:

It's and the quality, right? It's like the ability to pull out. I always talk about the sub-industry trends, right? Like instead of, oh, you know, other manufacturing companies or CPG brands, it's like, no, like what type of consumer good is this? No, not health and beauty. It's actually, you know, you know, Rodan and Feel. It's it's facial cream or whatever, you know what I mean? Like, and the ability to get to that level to whereas you're a newer rep or a newer salesperson, that I can get, I really believe, and again, in and to make them actually smart, I can get a rep up to speed on an industry faster than ever, because then, you know, after they craft that message, maybe for the first month, I then tell them, I say, and I want you to create a 15 question or 10 question trivia game that teaches me what the actual trends are for this persona in this sub-industry, and they take three minutes to do that. And then wait till you see the quality of the conversations in six to eight weeks. Because again, I think that that's it. You know, David, you hit it on the head. It's you know, MIT is, I was literally talking to one of my people earlier today on this exact topic. And um, you know, MIT has put out stuff about how our brains are becoming, you know, more mush. And it's like, well, I think one of the things that you and I are fortunate of is we are we have an an index of experience to pull from. So we have some like context to be able to do better prompting or better context giving because we have an expertise around something. Um, but I think no matter what, you can teach yourself it and just catch yourself to then teach it, teach yourself the thing. And if you just do that, if you just take an extra step and you don't have to do that on everything, I think that is how you really become like AI superpowered versus you know, a hundred percent. And you as a chef, it's like, this is amazing. What if I added, you know, Herbe de Provence, you know, to it as as well, too, right? That's what takes it from a you know eight to nine shadow. That's like my go-to. That's like my go-to. You know, I'm like, what should I season? And like Herbe de Provence. You know, it's just kind of a good like catch-all. I don't know. Is that like a cheat? Is that like a cheat as a chef?

SPEAKER_01:

My opinion. That's it. Everything from Provence.

SPEAKER_00:

That's right. Yeah, everything. Well, let's talk about endless, man. So we're kind of jumping into the B2B, you know, kind of world here. Um, and obviously, look, influencer marketing, you know, why it's the few, you know, the future or it's here and now, you know, what does it mean to be an influencer? You know, you think about how the algorithms have evolved over the last few years with, you know, you're only as good as your last video, you know, as opposed to I have a million followers, right? You know, it the the the average person on you know TikTok or Instagram, et cetera, can you know start to get pretty decent sized followings pretty quickly if you know how to, you know, get in the in the the for you page. Um so how how does AI fit into this world, right? You're seeing like the virtual uh avatar people, you know, like people are creating fake influencers now, you know, as a part of this. So like, you know, how does AI fit into like your world today? You know, how how are you all thinking about you know where it fits in with your clients and you know how you as a brand or as a company think about establishing trust and you know to sell products?

SPEAKER_01:

Well, if you would have asked me this question two weeks ago, I would have said that AI video creation, I don't think it's there yet. And I think it's really the skill of the creator. And then I saw the Sora 2 ad, and I was like, oh, I don't even know what's real anymore.

SPEAKER_00:

Um 100%, man. And the voice stuff too, the voice, like pure voice, 11 labs. I'm just like, that sounds like me. You know, like I've done it, I've voiced one.

SPEAKER_01:

In every regard, but um the the creator in in this world, they've obviously the really good ones, the ones that stand out, they are true artists, right? Like I could not make a video like that to save my life. Um, I think the ones that are using AI to do, again, access to information. I've got an opportunity to do a brand. Uh I'm wearing an Arcteryx sweater right now. I have an opportunity to do a campaign with Arctaryx. You know, give me all the research on Arcteryx, give me all the research on their customers, give me all the research on the products, um, give me five ideas that identify with this, like they can get to their own content creation faster. They can obviously shoot their content, they can then edit it faster. And a really high-functioning person, even at a mid-tier, I'm not talking like I've got a team of production people, I'm talking someone who's got 50,000 or 100,000 followers. If they're using it to elevate and augment their own ability, um, they might do a, you know, a paid campaign with Arctaryx where they're putting their content out everywhere and Arctaryx is boosting it. But behind the scenes, they might be doing five CGC campaigns with, you know, a footwear company, a pamp company, where they're not actually posting it on their own social, they're just selling the content like a commercial factory. And the better those individuals get at augmenting every step of the process, and then by the time Sora 3 comes out, it's just gonna be David's AI avatar, and I'm prompting what I'm, you know, David is surfing in uh, you know, the west coast of BC, and there's a bear on the on the beach, and he's wearing an arcteric sweater, and you probably wouldn't even know.

SPEAKER_00:

That's right.

SPEAKER_01:

Um, I think that is gonna have a really big impact, but it's just gonna increase the the the quality and the output of the really great people.

SPEAKER_00:

That's right.

SPEAKER_01:

There's the people that are always gonna go viral because they just hit the the the like lottery in that regard. Um, from the brand side, when you flip that on that, where we help um is AI search. So when a brand is looking for someone like David, they can come into our platform and just you know type in natural language I'm looking for, type in the criteria. Um, and then the other side that really helps the brands is we use a lot of gen uh genai in the messaging. So creators today are bombarded with uh inbound from uh from brands that want to work with them because they are the new currency in marketing. Like it's no longer influencer marketing, it's marketing. Um so what we do is we have a nice little AI that, you know, I find Jake and you want to write him a message, it'll write a message to Jake, but it'll also go to his social handle and pull in information like I love your last video about this, and personalize it because it's you know, we're trying to get you to the authenticity part where you got a message of hi Jake, I'm David from so-and-so, and we have a campaign. And would you like to be in that versus like, hey Jake, we really like that last video you created uh about surfing on the beach on the west coast of Canada. I think you'd be a great fit for the brand. And that's how we're augmenting it for the for the for the brand side. But it's it's the whole space. I've said it for a while, I think it's still it's it was in its infancy, infancy, it's starting to mature, and the pace at which AI is now um evolving in content creation, it's it's it's gonna be wild to see. But I think in a year from now you won't be able to tell the difference between David's video and David's AI video. And what Sora did last week, I guess it was earlier this week, was unbelievable.

SPEAKER_00:

We're but I think what one thing that you said I I hope people listen to that, you know, I was talking to this person on my team today, and I could tell like he was, you know, I don't know, discouraged, but definitely like in despair of like, well, what does this mean? You know, and I'm like, well, you know, I I think it I don't think it changes a lot. Like you're just gonna have to be good. Like you've got competition, like maybe we could get by, you know, with like maybe working a like less or less hard or trying. And it's like, yeah, the bar is raising. And so I feel like, look, there's plenty of room to compete and jobs that will be available and you know, areas for humans to add a ton of value in the sales process. But you better be good. You know, like if you're not good and you're not adding incremental value and you're not studying the craft and like how to be of value to your audience, people won't want to talk to you. I'd rather talk to digital David.

SPEAKER_01:

Yeah, in the sales world, you can use AI to craft all the great emails you want, but remember, you still gotta jump on the phone with the person. Uh, you still gotta be like, wow, like I read Jake's email. I got on a call with him, like, man, I really like that guy. I could absolutely go and have a beer and talk this deal through. Versus someone who just does not and cannot build that rapport with a client in the in a B2B sales world, you're gonna struggle and it's gonna show really quickly. You might be the best outbound SDR ever, but just don't put Dave on a call with people because he can't talk, because he doesn't know how to talk, because he AI is everything.

SPEAKER_00:

He AI at everything. Sounds like a genius.

SPEAKER_01:

AI's everything. Yeah, he's he yeah, send AI Dave to the meeting because regular Dave just is not gonna be able to come on.

SPEAKER_00:

That's all that's gonna happen five years from now. It's like my AI being like, all right, man, let me talk to you. And then other AI, like, I don't want to hear this. You know, it's like all uh all interacting. And this is actually a good, a good segue to kind of like your, you know, your um, you know, you've deployed AI to direct sellers, influencers, brands, etc. Like, are there any like universal principles, you know, that you feel like or you know, use cases where you know AI is just the superpower, like regardless of like sales context, like you know, Jake, here are like the top two or three areas, and then we can kind of dive into to each one of those.

SPEAKER_01:

My belief, I'm pretty pretty big on this one, is that AI is meant to augment, augment, not replace. The moment you try to take an AI to replace the job that a human is doing, I think you're gonna I think it's gonna blow up in your face. Um like um great example, uh vibe coding, hot, super hot topic.

SPEAKER_00:

Yep.

SPEAKER_01:

You can't really release a vibe coded app into production and think it's gonna work great. There was a there's a couple stories in TechCrunch in a few weeks where it app blew up because you you just like, hey, make me an app, and all of a sudden there's security breaches and everything blows up. Um the experiences I had using AI SDRs, full of code copilot, it was terrible. Um, you gotta empower your employees just to work more efficiently and just be like this AI is meant to elevate you. Let's take some of the mundane things away from you and put you on higher value work or more strategic work. Um, like in endless, right? Don't spend all day just cold emailing people hoping they respond. The AI will fire off you know a hundred messages by the time you personalize three. Um, that is probably one of the biggest ones for me, especially when you think about all the things you could do with it. Um I think one of the other things is I think you should test everything because it's moving, keeping pace with everything that's happening. Like um OpenAI is announcement yesterday with the new uh that again is gonna change absolutely everything. You're like, how's that gonna change my workflows? How's that gonna change my inbound? How's that gonna change my on website conversations? How's that gonna change my conversion optimization? Like everything is changing. So I think you just have to keep keep pace. I I've got three kids at home, and in the evenings I'm an Uber driver and a bit of a DoorDash delivery driver getting these kids around. I I don't have the time to even keep up with it.

SPEAKER_00:

That's right, though. I mean, yeah, and it's a a good, you know, we've got an AI certification program uh that we literally just launched for leaders and for reps. Uh six-week program, you'll build assistance, you'll actually build workflows in in Aiden or whatever platform you have access to. So, and and I was I was talking to someone yesterday, and it's like, well, Jake, what you know, how should I think about this? And I I basically said, you can't afford not to learn this. Like, I think we all have to realize like we are all going back to school, and you have to dedicate the time, you know, like you have to dedicate the hours to learn this stuff. And to your point, if somebody you know runs a consulting firm that does this, you know, all day long. Somebody asked me in a session a couple weeks ago about Jake, you know, how do you, how did you, how do you stay up to speed? And did it? I go, I always feel like I'm drowning. Like I still feel like I'm not. And and I always feel like I can't, but I know that you just have to keep paying attention and that we have to, you have to in today's day and age be dedicating time. I don't care if it's an hour a week or two hours a week to getting better because this tool, and very quickly, if you're a a B plus player, a C who's really, really good at leveraging and contextualizing different ways to leverage AI, will just outpace you. Like they'll just be able to move at just such a speed that, like, yeah, David's, you know, technically better, but Jake is 8x more productive. So I sorry, David, like if you don't, you can't keep working like this. Like I can't employ you. And and I feel like that's the area of opportunity for a lot of these folks is just to learn the the of how to try to stay up to speed, you know, and just making sure you're taking the time, and especially for all my leaders out there, you know, where I feel like our time in particular, like you said, you're in an Uber and you know, DoorDash, and I can I I've got two two young kids, so I can relate. Um it's it's uh it's tough, but I would just I would just caution everyone, it's necessary. Like, yeah, you can't again, like the you can't not know, like, okay, well, what what happened here and what did what happened? Because I think what happens with a lot of salespeople, once they once we start to talk tech, salespeople's eyes just glaze over. And it's like, wait, I I got a code. It's like, no, you don't. But if you can understand how all these things work together, you can start to think of the art of possible. And that's really the skill set that I think is creativity, strategic thinking. These are the ones that AI is not going to be able to replicate. It can be a thought partner and it is creative, but you know, creative ways to apply it. Um, you know, and you know, you mentioned a lot of these use cases too, about like where to apply it. And and my question kind of following up here is what's too far, right? So, like what are let's what are like what are the red flags? Like, what are the specific signs? It's like random insights that aren't actually applicable. That's a good one. But you know, uh, how should people, if they're listening to this, like, okay, like where where is that line? Because it sounds like uh, you know, I want to use AI to get to this point, but then I need to turn my brain on and do this. Uh where do you feel like that flag is of like, man, you gotta make sure you're not doing these these things? I always say copying and pasting AI, that if you're copying and pasting AI, that is the surefire way to be unemployed in the next two years. As a part of it. What else? What are some of the other use cases where you feel, you know, hey, avoid this or you know, make sure you're always doing this manual-ish?

SPEAKER_01:

My kind of rule of thumb is I avoid trusting AI fully where I don't have the raw skill set to do it. Right? Do I like that? If I go in and I'm like, hey, here's a spreadsheet, do a V lookup for me and tell me this. If I can't do that myself and I'm just gonna trust that the AI is doing the correct thing, and then I'm gonna send that to my boss or to a client, like you're like, fuck peace. Hopefully I'm done. And I think that's with every everything, right? Like I I when Lovable came out, I was playing around with that thing. Just it was so cool. And then it's like, oh, it's detected in an error. And then I'm like, well, then write a prompt to fix the error, and then it writes a prompt to fix the error, and then it fixes the error. But I have no idea what the error was. I have no idea how to fix the error. I don't even really know how to probably look in the code base. Like I'm I'm just blind trust, and I think it's in every vertical in your in your company, whatever you do. If you don't understand how to do the job to get the right output on your own, even if it's going to take you three hours or five hours, you can't just go in there and blindly trust AI to do it accurately because it's you you just can't afford to screw that up.

SPEAKER_00:

That's such a good call out. That's I I haven't heard anybody articulate that, um, which is you know you're going too far if you find yourself consistently blindly trusting and it's not something that you know how to do. And you know, you're having AI check its own AI, which look, in certain cases, that's okay. But if you also to, you know, if you don't have an understanding of what good looks like, um you're gonna have a real tough time spotting when AI is falling down, or where AI is just flat wrong, or AI it doesn't have enough context because you don't have enough context. And so because you don't have enough context, you're going down, you're you're going east and you should be going, you know, northwest, for example. Yeah, but I think that's a really good call at David.

SPEAKER_01:

Yeah, I'm not great at prompting, and I don't know what the output looks like, but F it, here we go. Like you just I think you could end up in a lot of hot water. And um prompting is obviously such an important skill set. And it's like I took my you know 100-hour course and did all the things, and I'm still not that good at it, to be honest.

SPEAKER_00:

But yeah, what we find consistently, this is kind of a tactical tip for everybody out there. The most important thing is we are just so used to speaking to machines in five words of broken English in Google, right? Like that is most of our how our brains are are hardwired, you know, to to and so we are unbreaking the pattern of like, no, give it another sentence and another sentence and then ask it to go deeper and give it another sentence and another. And so I think for a lot of people, just understand we're we're rewiring the way that we interact with machines. And I think that that's where I feel like a lot of people struggle is just continuing to, you know, I say you've got to keep pushing, keep pushing. One more sentence, two more sentences, more context. And and again, to your point, I still don't think I'm a 10 out of 10 at this by any stretch of the imagination. But um, we have to get better and better at again, giving the context. If you can't give the context, or if you're giving surface level context, you're gonna get surface level insights and answers. Like that's what's gonna be.

SPEAKER_01:

Yeah, but the machine's also gonna solve the problem the same way you do. Right? It it could look at the problem a completely different way that you've never even fathomed. And therefore certain you're gonna have a different output. But again, context obviously is the most important thing. And you know, I want to do this, this is what I need to do, ask any clarifying questions. In doing that, you're gonna act like this person. This is my goal, pop, pop, pop, pop. I just write it forever, and then you'll get there.

SPEAKER_00:

How can okay, this is a deep one. If I'm early in my career, what am I gonna do? Like, okay, if I'm 23, okay, I'm 23-year-old Jake. I just graduated from let's go somewhere cool. I go, I went to like Ole Miss or somewhere. I don't know. I live in Austin now. Ole Miss just looks like a cool place. I don't know.

SPEAKER_01:

I I agree with you on that one.

SPEAKER_00:

You know, like, okay, I just graduated Ole Miss. I got a marketing degree, and you know, I did a couple internships, I have a year of experience. You know, how how does this newer sub, I'm gonna say sub-five, sub-tenure experience? Um, you know, kids coming out of college are learning the Gen AI, you know, in class, right? How do I get context? How do I, how can I use AI to get context without having as much experience as you and I have?

SPEAKER_01:

The I would say find a company where you are dialing for dollars. Like you are on the phones, it's you're not cheating behind a keyboard, and you have to actually learn skills, real-time objections, and actually talk to people. And you need to bust your ass harder than anyone else there to get your stripes so that you can talk, actually talk to people. Yeah, it's it's a it's gonna become a lost art because we all just hide behind a keyboard.

SPEAKER_00:

That is good. I didn't know where you're gonna take it, but that was that's exactly right. Like I that's exactly what I was telling that guy earlier today. I was like, dude, the and you know the answer is hard work. Like the answer is you have you need to go get it. And and if you're at a place, I tell any seller listening to this, listen to what that you know, what David just said and what I'm about to say. If you are at a place that is telling you to hit send all on templates, if you are at a place where they view the first interaction with a potential customer as a qualification call, you need to run immediately. You are literally learning nothing. You are not learning how to interact, you know, you are not learning how to consult somebody. That is the future. The only future is consultative selling. And I don't care, you can call it spin selling, I don't care what methodology you have, but the only future is a human being who can add so much value in the quality of the questions that are that can be so nuanced that AI might not pick up on. They know the industry, they you can connect. Oh, hey, David, great conversation. Oh, hey, we work with six other PSG companies. Do you know Mike over at Yoda? Like, that is it. And so if you are in a sales job and you are not doing what I just said, you have to leave. Like, I don't, I don't know like how else to say it. David, you tell me what you think. But that that to me is where I feel like in three, four, five years, you're gonna have a generation of sellers who are not going to be employable because they're not doing the hard work, which is what you just said.

SPEAKER_01:

Yeah, well, what if the AI that I use that failed miserably stops starts being successful? And I don't need to hire you fresh out of college because Dave, my AI avatar, who looks just like me, talks just like me, sounds just like me, can do it for me until I physically need to show up at your office. Like that's that's not out of the realms of possibility. Like, why in three years, five years? Why why couldn't that happen? I think 11x does did have a voice salesperson that I tested, and I was like, this is terrible.

SPEAKER_00:

Like, get there. It'll never be worse. I said that AI will never be worse than it is right now, and it's pretty awesome right now.

SPEAKER_01:

It's pretty amazing, it's pretty awesome as a part of this for absolutely everything.

SPEAKER_00:

Everything, right? And that's it. That's again with a lot of people like AI. Yeah, think about it. It's it's again, I was talking to right before we hopped on, I was talking to a client of ours and we're doing kind of an executive brief. And I was like, which you have to, you know, it's like, okay, so you know, do I hire this or do this? I said, uh go look, you have to realize you're never going to stop for the next two years. All we are going to be doing as leaders is retraining every role in our go-to-market teams how to do things a different way than we all learned that made us successful. And so you have to realize this AI journey that you're going on, whether you're a frontline seller, a leader, CEO, PE firm, whatever, is we are going on a multi-year journey to completely refactor the way that we solve all of our everyday problems, whether that's an assistant that we interact with, an agent that's doing things for us on the side. And so that's where, you know, you've got to just sign up for the long haul. Because to your point, as it evolves, if you're trying to comprehend, you know, what we're talking about a year from now, and because you didn't invest back here to kind of start to understand or dabble, it's you're gonna have a lot of trouble. You know, you if you're if you're not investing, I and that that's really where, you know, I'm worried. And this is actually a good segue. We're almost at time here, um, which is what do you see as next, right? As AI gets better at mimicking humans, does authenticity get harder? Does it get easier? You know, where do you see this going? You know, whether it's with your go-to-market teams or, you know, with your customers, and and how you are going to help to guide them through, you know, this authenticity, you know, challenge. Um, and you know, the only way to grow their business or to to grow their brand will be to be able to stand out whenever everyone's using this type of technology.

SPEAKER_01:

Where I see it going and where I want it to go are two different things. Where I see it is it's just gonna go, it's just the pace. Everyone's like, oh, we're so busy, we're so busy. Well, you're gonna be busier because it's just everything's gonna go faster. Um, where I want it to go, where I love to see it go, and I'm kind of seeing it in in just general, right? I'm 44. Um, a lot of my friends are moving off social media and going back to relationships, actually really spending time to connect with people. And like they're they're kind of just in the irony, of course, is I have an influencer marketing software that uses AI. I trust me, I that's not lost on me. But my my friend group is they're like, no, I'd rather, I'm I'm just not interested anymore. I'm really focusing on stronger, stronger relationships and just being present, like going to a show and actually watching the show, not filming the show and watching me filming the show versus like being at the show. Um, I I would love to see a byproduct of the pace at which AI is happening. More and more people go back to people. I mean, like, look, I I want my relationships. I built my career in this space. I can call Doug and Jim and Jake and Dave, and I could like, I don't know. That's just who I am as a person, though. I'm the I love going on the road for work. I love going out for dinner. I love building relationships with people. AI can never take that away. And I think, I think, well, Pendulum's gonna go over here and everyone's like, oh, automate, augment faster, bah. And then we're all gonna be like, I really miss talking to people.

SPEAKER_00:

Like, I think you're right. I think we're swinging back though. I I agree with you 100%, man. I I actually feel like what AI let me tell you how I see this manifesting in my own company as we're kind of AIing a lot of our work. We're there's two things that are happening. And one might be counterintuitive to what you just said. We're actually having less meetings. And and and but but what that's doing is freeing up people time to like have space to think and to work because I don't need to follow up with you on this thing or check in or do that. And so then when we are, you know, again, because we are busy, but then when we are meeting, I feel like the quality of the interactions are better. There's less catching up and you know, covering basic stuff. So I I do feel like, you know, the work meeting, yeah. I saw some stat, it was crazy. It's like since the 60s, it's like we have like 10x more meetings than people had in the 60s, which is like as wasn't it supposed to go the other way, you know.

SPEAKER_01:

Like you like we all work as same creeping.

SPEAKER_00:

We've got more tech now. But but I feel like it's it's it's it's helped there. And I and I think that that could be the promise of some of this too, David, is you know, imagine a world where if I'm not having to do that, that's dumb blocking and tackling stuff that sucked that extra 45 minutes every Thursday night or X amount a week and logging my expense report or you know, if I as we get rid of that, I actually think it will create more space for us to think and interact in a in a in a more human way as a part of it. So I actually I I see that coming back and uh you know, certainly to to some extent, you know, around people wanting to, you know, interact more, be more present. And and I think hopefully if we can automate that busy work, truly busy work, then we can spend more time thinking, which I think is where most of us would like to live, but we've just been so conditioned to live on the wheel that we we're not taking the time to build systems and processes that will ever get us off the wheel.

SPEAKER_01:

Yeah, and you said the dirty word for every salesperson is I gotta do my expenses. Like, that's what AI.

SPEAKER_00:

You know what it's your expense report is a part of it. That's the beautiful part about being a CEO, David. I do not have that problem. Like, I create that problem for my team. They're like, Jake, please stop, use this, not the Amex. I'm like, it's happening on the MX. I'm probably sorry.

SPEAKER_01:

Oh we must have the same people.

SPEAKER_00:

Exactly. Hey, this is my one thing I get, okay? The other rest of the time, you know, I'm catching all the you know, all the you know what, and light, you know, putting out the fires. But but no, this was awesome, man. I think we covered a lot of ground here. I think this conversation around where the human exists in the process today, um, how we should be thinking about AI, I think we've covered a lot of ground. And I think, you know, what I really enjoyed about this conversation is I think we got really tactical too, to where hopefully everybody listening is gonna be able to say, ooh, here's like one thing or two things that David said or Jake said that I'm like, I can now think about maybe reworking how I'm using AI, you know, where I'm showing up in my journey with customers and how I'm augmenting with AI. So I think, you know, I think people are gonna get, you know, a lot out of the episode. And David, you know, where where can people find you, learn more about you know what you're building?

SPEAKER_01:

And I think LinkedIn is definitely the best place uh uh for me. I'm relatively active on there. Yeah, yeah.

SPEAKER_00:

That's how we got that's how we got connected. And we'll make sure we'll we'll put a link in the bio for you uh, you know, as well too, and you know, link to endless and what you're up to there as well. So uh I really enjoyed it, man. I really, you know, i I I love the dialogue. It's fun to have a quick really the future-looking but also tactical conversation. So I really appreciate it. Thanks, man.

SPEAKER_01:

Yeah, well, I really appreciate having me on, and I really enjoyed this as well. So thank you very much.

SPEAKER_00:

All right. Thank you, everyone. That's a wrap. We will see you next week on the AI Powered Cellar.

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Jake Dunlap

Co-host