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November 5, 2025 45 mins

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.

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_01 (00:00):
We all have our battle scars from dialing for
dollars and sitting in like awet room back in, you know,
2000, just like somebody pick upthe phone.
I I think that's gonna be a lostart.
I just don't think people aregonna get it because they're
just gonna find these cheatcodes and be like, well, I've
got an ICP that has three orthirty thousand customers.
And what's really cool is if youuse an AI to say, I've got

(00:22):
thirty thousand customers, gogive me a battle card on Jake
and help me craft a messagethat'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 (00:35):
Every seller today is becoming more and more
terrified of the same thing.
And that is becoming less andless 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 beauthentic.
And that is why I am superexcited for today's episode of

(00:58):
AI Powered Seller.
Uh, today's guest, Mr.
David Abbey.
David, CEO, co-founder ofEndless and Penny AI.
Um, this guy was in the AI gamebefore AI was Gen AI, right?
So he spent the last decade atthe intersection of technology,
social commerce, AI.
And what I love about thisconversation we're gonna have is

(01:20):
David also deeply understandssales and deeply understands
what it takes in 2025, 2026 tobe successful in creating
authentic communication.
So in today's conversation, weare gonna go deep on like what
does authenticity even mean?
You know, he we'll talk aboutyou know digital avatars and you

(01:42):
know, they they do influencermarketing.
So, what does the future of thatlook like?
We're gonna talk also about moretactical day-to-day use cases of
hey, where should I 100% beusing 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 conversationtoday.

(02:04):
It's gonna be a good one.
You're gonna want to get outyour digital notepad or your pen
and paper because today'sepisode is gonna be a fun one.
All right, David, welcome to theshow, man.
I'm looking forward to theconversation.

SPEAKER_01 (02:14):
Thank you very much, Jake.
I'm uh yeah, I've been lookingforward to this as well.
I'm excited to be here.

SPEAKER_00 (02:18):
Yeah, this is gonna be a fun one.
I think this I, you know, we'rein this very AI era, obviously,
for all of you tuning in.
That's why you're here is tounderstand, you know, what does
the future look like around GenAI?
Uh, how am I gonna use ittactically in my role?
And I think, you know, today'stopic around authenticity,
right?
And what it means to beauthentic authentic.

(02:39):
I think we're gonna, I thinkwe're gonna have a pretty good
conversation here, as manypeople I know are somewhat
struggling with this, I feellike, 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 ifthe line's blurring or something
like that.
I I you know, I've got somefeelings about this, but I want

(03:00):
I want to start with you.
Some feelings about it as well.
Yeah, and like what got you intothis?
You know, what got you intothis?
You know, you've built twocompanies now with you know,
Penny and Endless.
You know, um how did you whatgot you into this?
This kind of automation versusauthenticity challenge, you
could say.

SPEAKER_01 (03:19):
Uh my wife, actually.
Okay so uh Penny AI is acompany, um worked uh
exclusively in the directselling vertical.
Um so multiple marketing, sothink Tupperware, New Skin,
Avon, Arbon, Damway.
Um, and it was when my wife andI, we had three kids in diapers,
and she was working with uh acompany called Rodan and Fields.

SPEAKER_00 (03:41):
She's she's a uh yeah, I remember that one.

SPEAKER_01 (03:44):
Redanana Fields, Dr.
Rodan and Dr.
Fields, like brilliant,brilliant people.
Um, my wife is a nurse.
We had three kids in diapers, soshe couldn't work, so she
started that business.
And it was actually watching hertry to build relationships in a
scalable way while being a newmother three times over.
Um, and she literally said tome, David, I need you to build

(04:07):
me something that tells me whatto do.
And uh a good friend of mine,Chris Noble, who's our my my
co-founder and and CTO, he uhhad ran the labs and innovation
team at Hootsuite.
He understood social incrediblywell.
Um, he brought in one of hispartners from Hootsuite, a guy
named Andrew Draper, who hadbeen in the e-commerce and D2C
space going back to thebeginning of D2C.

(04:30):
Um, and the companies of thosesizes have so much data that
they're sitting on, likeRandonfield specifically.
Um, but their distributedworkforce is a volunteer
workforce that is working offnot even the side of their desk,
they're working in moments oftime.
And when you think about thatauthenticity question, it's like
someone is trying to build apersonal relationship to sell

(04:51):
them a product, whether it's ayou know, a uh a regular
business, a car salesman, or inthe in the direct selling
industry for Red End and Fields,where AI really comes in to
create the opportunity to beauthentic 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

(05:15):
keep track of it to save herlife, wanted to have authentic
conversations.
And what we did, and this wasthe big data machine learning
era back in 2017, 2018, is howcan we surface the information
that we have uh vis-a-vis fromBernan and Fields to tell people
what to do every day and givethem information so that when

(05:36):
you know Terry reached out toJake, she's quickly able to look
at his order history.
She can look at her notes, likea pretty, you know, the the
fundamentals of a CRM, but doingit in a daily way.
And Penny was the name of thecompany, Penny was your virtual
assistant, Penny would tell youhow to do this, Penny would link
and sync with your socialnetwork so you could easily
gather information.
And that's where it started.

(05:58):
And it started with my wife, andwithin um I I think a matter of
months, we had tens of thousandsof users because we solved a
real problem.
Because that vertical, thedirect 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 kindof hit the nail on the head.

(06:19):
And from 2018, all certainly allthe way through the pandemic,
um, we solved a very seriousproblem because people genuinely
want to have greatrelationships.
It's the access to informationat scale that makes it
challenging.
And that's where I think AI isbrilliant, is it can just
surface the right information tobe very meaningful.

SPEAKER_00 (06:41):
Yeah, I mean, like I think that's where a lot of this
starts is, you know, we'retrying to actually that's a
really good note for people tothink is that, you know, we use
this word, I think, AI andautomation in a lot of the same
sentences, but you know, whenused correctly, what we're
really talking about is using AIto have better relationships or
strengthening relationships andyou know, surfacing things that

(07:02):
it's not that you couldn't havefound this information, it might
have been public or sittingsomewhere, but you know, it just
pulled it together faster foryou.
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 tohaving to just figure it out
themselves.
And, you know, so then as theystart to think about this

(07:23):
automate human combo, I thinkthey struggle with it.
And I think this is a good kindof follow-up here is, you know,
when you think about Pennyfirst, right?
And we talk about that, youknow, how did you think about,
and this is before like Gen AI,right?
So Penny was, you know, ahead ofits time.

SPEAKER_01 (07:39):
This is before Gen AI, yeah.

SPEAKER_00 (07:40):
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 thethings that, you know, you think
about automation?
Obviously, there's things likeresearch, 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 thatthings that people should not be

(08:02):
trying to automate and keep, youknow, human only or
human-assisted?

SPEAKER_01 (08:10):
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 mygod, like head in the hands,
like, okay, I gotta turn thisoff.
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

(08:32):
have to run every aspect oftheir business.
So we automated as much as wecould without ruining um the
relationship.
And one thing we took a stancevery early on in is we are not
going to be an um email blastingsolution.
We are going to integratedirectly with LinkedIn and
Twitter and Facebook andInstagram.

(08:55):
And if you want to messagesomeone, we even got to the
point when Gen AI started comingout.
We would recommend content thatyou could say, like scripts.
We could recommend content youcould share, but we never allow
people to blast it to everybodybecause that ruined
authenticity.

SPEAKER_00 (09:10):
100%.

SPEAKER_01 (09:11):
We would be like, here's Jake, here's why you
should talk to him, here's whatyou could say, but you can't
send this to everybody.
And that, but we got them allthe way to the line, and then
we're like, now it's on you togo and have this one uh one
conversation.
And we got it so many times fromour users, they're like, Thank

(09:31):
you so much.
Like, you knew you recommended Italk to this customer I hadn't
spoken to in three years, and Iforgot.
And I reached out to them onFacebook.
And when I opened up theFacebook, and the cool thing is
when you go in and have aone-to-one message with someone,
those apps do such a great jobof indexing your entire history
with that person.
And they just be like, I jumpedin and I instantly realized, you

(09:54):
know, this was such a greatfriend of mine, and I just lost
track because I had been in thehamster wheel trying to build my
business.
And we always want to get you asfar as we can, but we didn't
want to take away the humanconnection of it.
And we used as much access toinformation as we could to make
you do that more efficiently.
So my wife's classic line waswhen I have five minutes in the

(10:14):
high school pickup line or inthe school pickup line, she can
open up do something that ismeaningful that drives her
business forward.
And in the the the topic ofauthentic authentic ways, hey
Jake, it would, you know, Ihaven't talked to you in a
while, but we would be able toserve her information to be
intelligent and be accurate.

SPEAKER_00 (10:36):
Yeah, I think again, that's where I feel like
outbound today, I mean, inparticular, right, is the lack
of that.
I feel like there's almost justa lack of like reality or
appreciation of understanding.
Like, no, no, no, like the humanhas to be in the loop here.
Now, if you're just doing someblanket approach, it's a
transactional sale.

(10:57):
You know, I can make an argumentthat, you know, some of the
outbound AI or automation stuffis is could be more applicable,
you know, potentially.
But I do feel that it's not, andI say that from personal
experience.

SPEAKER_01 (11:10):
We tried um two of the you know, venture-backed uh,
you know, digital workforce uhemployees, and they I haven't
seen a piece of software sawfall that flat on its face that
quickly, and it's not there,it's not there at all.
I I saw one of my LinkedInmessages, and it's like, hey,

(11:31):
something about me going totheir church and a fellow, you
know, right or something, and Iwas like, what is happening
here?
And they except to my LinkedIn,right?
Which means they obviouslydidn't look at my profile.
But it was just thehallucinations were so far out
there, and I think a lot ofpeople are it's a cheat code,

(11:53):
but I also think anyone cominginto B2B sales and outbound
sales, like we all have our ourour battle scars from dialing
for dollars and sitting in likea sweat room back in you know
2000, just like somebody pick upthe phone.
Uh I think that's gonna be alost art, and I just don't think
people are gonna get it becausethey're just gonna find these
cheat codes and be like, well,I've got an ICP that has three

(12:15):
or thirty thousand customers.
Send.

SPEAKER_00 (12:19):
That's right.

SPEAKER_01 (12:20):
What's really cool is if you use an AI to say, I've
got 30,000 customers, go give mea battle card on Jake and help
me craft a message that's uniqueto 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 (12:36):
Yeah.
Well, the funny part is like ita lot of it's not really a cheat
code if it sucks, you know, witha lot of these things.
Like, I think I think peoplethink that they're they they
think that that they're a cheatcode, but you hit it on the
head, man.
And we're, you know, we do a lotof generative AI deployments for
our clients.
And, you know, that's a lot ofwhat we say is like, look, let
us get you to the point whereI've got like some amazingly

(12:58):
relevant piece of insights.
Like we've got a client um thatuh does website speed um
optimization, right?
And so let's use AI to go andscrape the, you know, scripts
that are running, highlight thetwo or three that, you know,
what a rep would have had to goinspect Elements.
They would have had to go try tothink about what are the two or
three that we should optimize.

(13:19):
And then you turn your brain on.
And here's the template, and itpulls 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 fashionapparel.
And this thing is why we'rerelevant to fast fashion versus
athletic.
You know, I'm just like makingup an example.
But I I I think that that iswhere the the teams that are

(13:41):
winning and outbound are eitherjust, you know, they're smaller
companies that just torch theirTAM initially because they're
like, forget it, we'll figureout how to get to 10 million or
15 or whatever it is.
Um, and then they have nosustainable way to continue the
growth.
Or is the company doing what Ijust mentioned?
That, you know, they're the fithe fire, you know, the the the
the flamethrower approach canonly work to a certain extent.

(14:04):
And then you have to be able tohave people turn on their brain
if you want to win.

SPEAKER_01 (14:07):
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 verypassionate chef at home.
I just use ChatGPT now.
How do I make this?
I don't even think about itanymore.
But the I think the companiesthat are gonna do really well is
that you instead of torchingyour TAM, and this is where

(14:28):
we've we've been testing theiterating messaging nonstop
because endless is still arelatively new entrant in the
influencer commerce space.
Um, we are taking sets.
You know, hey, here's X numberof companies.
We're testing this language andthe but we're using AI to write
it all.
We're you know, hey, this is theICP.
We're getting the AI to do afull breakdown of the ICP with

(14:49):
the messaging, the valueproposition, and the business
objectives that our reader isgoing to be going after.
Let's test this messaging.
Okay, this kind of worked, thesethings hit.
Now let's do V2, V3, instead ofjust everybody we are being very
methodical in our approach, butthe speed at which we can do it
that's right, um, is completelyridiculous because yeah.

SPEAKER_00 (15:14):
It's and the quality, right?
It's like the ability to pullout.
I always talk about thesub-industry trends, right?
Like instead of, oh, you know,other manufacturing companies or
CPG brands, it's like, no, likewhat type of consumer good is
this?
No, not health and beauty.
It's actually, you know, youknow, Rodan and Feel.
It's it's facial cream orwhatever, you know what I mean?

(15:35):
Like, and the ability to get tothat level to whereas you're a
newer rep or a newersalesperson, that I can get, I
really believe, and again, inand to make them actually smart,
I can get a rep up to speed onan industry faster than ever,
because then, you know, afterthey craft that message, maybe
for the first month, I then tellthem, I say, and I want you to
create a 15 question or 10question trivia game that

(15:56):
teaches me what the actualtrends are for this persona in
this sub-industry, and they takethree minutes to do that.
And then wait till you see thequality of the conversations in
six to eight weeks.
Because again, I think thatthat's it.
You know, David, you hit it onthe head.
It's you know, MIT is, I wasliterally talking to one of my
people earlier today on thisexact topic.
And um, you know, MIT has putout stuff about how our brains

(16:19):
are becoming, you know, moremush.
And it's like, well, I think oneof the things that you and I are
fortunate of is we are we havean an index of experience to
pull from.
So we have some like context tobe able to do better prompting
or better context giving becausewe have an expertise around
something.
Um, but I think no matter what,you can teach yourself it and
just catch yourself to thenteach it, teach yourself the

(16:41):
thing.
And if you just do that, if youjust take an extra step and you
don't have to do that oneverything, I think that is how
you really become like AIsuperpowered versus you know, a
hundred percent.
And you as a chef, it's like,this is amazing.
What if I added, you know, Herbede Provence, you know, to it as
as well, too, right?
That's what takes it from a youknow eight to nine shadow.

(17:04):
That's like my go-to.
That's like my go-to.
You know, I'm like, what shouldI season?
And like Herbe de Provence.
You know, it's just kind of agood like catch-all.
I don't know.
Is that like a cheat?
Is that like a cheat as a chef?

SPEAKER_01 (17:14):
My opinion.
That's it.
Everything from Provence.

SPEAKER_00 (17:16):
That's right.
Yeah, everything.
Well, let's talk about endless,man.
So we're kind of jumping intothe B2B, you know, kind of world
here.
Um, and obviously, look,influencer marketing, you know,
why it's the few, you know, thefuture or it's here and now, you
know, what does it mean to be aninfluencer?
You know, you think about howthe algorithms have evolved over
the last few years with, youknow, you're only as good as

(17:38):
your last video, you know, asopposed to I have a million
followers, right?
You know, it the the the averageperson on you know TikTok or
Instagram, et cetera, can youknow start to get pretty decent
sized followings pretty quicklyif you know how to, you know,
get in the in the the for youpage.
Um so how how does AI fit intothis world, right?
You're seeing like the virtualuh avatar people, you know, like

(17:58):
people are creating fakeinfluencers now, you know, as a
part of this.
So like, you know, how does AIfit into like your world today?
You know, how how are you allthinking about you know where it
fits in with your clients andyou know how you as a brand or
as a company think aboutestablishing trust and you know
to sell products?

SPEAKER_01 (18:18):
Well, if you would have asked me this question two
weeks ago, I would have saidthat AI video creation, I don't
think it's there yet.
And I think it's really theskill 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 (18:34):
Um 100%, man.
And the voice stuff too, thevoice, like pure voice, 11 labs.
I'm just like, that sounds likeme.
You know, like I've done it,I've voiced one.

SPEAKER_01 (18:44):
In every regard, but um the the creator in in this
world, they've obviously thereally good ones, the ones that
stand out, they are trueartists, right?
Like I could not make a videolike that to save my life.
Um, I think the ones that areusing AI to do, again, access to

(19:06):
information.
I've got an opportunity to do abrand.
Uh I'm wearing an Arcteryxsweater right now.
I have an opportunity to do acampaign with Arctaryx.
You know, give me all theresearch on Arcteryx, give me
all the research on theircustomers, give me all the
research on the products, um,give me five ideas that identify
with this, like they can get totheir own content creation

(19:26):
faster.
They can obviously shoot theircontent, they can then edit it
faster.
And a really high-functioningperson, even at a mid-tier, I'm
not talking like I've got a teamof production people, I'm
talking someone who's got 50,000or 100,000 followers.
If they're using it to elevateand augment their own ability,
um, they might do a, you know, apaid campaign with Arctaryx

(19:49):
where they're putting theircontent out everywhere and
Arctaryx is boosting it.
But behind the scenes, theymight be doing five CGC
campaigns with, you know, afootwear company, a pamp
company, where they're notactually posting it on their own
social, they're just selling thecontent like a commercial
factory.
And the better those individualsget at augmenting every step of
the process, and then by thetime Sora 3 comes out, it's just

(20:12):
gonna be David's AI avatar, andI'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 thebeach, and he's wearing an
arcteric sweater, and youprobably wouldn't even know.

SPEAKER_00 (20:24):
That's right.

SPEAKER_01 (20:25):
Um, I think that is gonna have a really big impact,
but it's just gonna increase thethe the quality and the output
of the really great people.

SPEAKER_00 (20:34):
That's right.

SPEAKER_01 (20:35):
There's the people that are always gonna go viral
because they just hit the thethe like lottery in that regard.
Um, from the brand side, whenyou flip that on that, where we
help um is AI search.
So when a brand is looking forsomeone like David, they can
come into our platform and justyou know type in natural
language I'm looking for, typein the criteria.

(20:57):
Um, and then the other side thatreally helps the brands is we
use a lot of gen uh genai in themessaging.
So creators today are bombardedwith uh inbound from uh from
brands that want to work withthem because they are the new
currency in marketing.
Like it's no longer influencermarketing, it's marketing.
Um so what we do is we have anice little AI that, you know, I

(21:18):
find Jake and you want to writehim a message, it'll write a
message to Jake, but it'll alsogo to his social handle and pull
in information like I love yourlast video about this, and
personalize it because it's youknow, we're trying to get you to
the authenticity part where yougot a message of hi Jake, I'm
David from so-and-so, and wehave a campaign.
And would you like to be in thatversus like, hey Jake, we really

(21:40):
like that last video you createduh about surfing on the beach on
the west coast of Canada.
I think you'd be a great fit forthe brand.
And that's how we're augmentingit for the for the for the brand
side.
But it's it's the whole space.
I've said it for a while, Ithink it's still it's it was in
its infancy, infancy, it'sstarting to mature, and the pace

(22:00):
at which AI is now um evolvingin content creation, it's it's
it's gonna be wild to see.
But I think in a year from nowyou won't be able to tell the
difference between David's videoand David's AI video.
And what Sora did last week, Iguess it was earlier this week,
was unbelievable.

SPEAKER_00 (22:21):
We're but I think what one thing that you said I I
hope people listen to that, youknow, I was talking to this
person on my team today, and Icould tell like he was, you
know, I don't know, discouraged,but definitely like in despair
of like, well, what does thismean?
You know, and I'm like, well,you know, I I think it I don't
think it changes a lot.

(22:41):
Like you're just gonna have tobe good.
Like you've got competition,like maybe we could get by, you
know, with like maybe working alike less or less hard or
trying.
And it's like, yeah, the bar israising.
And so I feel like, look,there's plenty of room to
compete and jobs that will beavailable and you know, areas
for humans to add a ton of valuein the sales process.

(23:03):
But you better be good.
You know, like if you're notgood and you're not adding
incremental value and you're notstudying 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 digitalDavid.

SPEAKER_01 (23:18):
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 theperson.
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 abeer and talk this deal through.
Versus someone who just does notand cannot build that rapport
with a client in the in a B2Bsales world, you're gonna

(23:40):
struggle and it's gonna showreally quickly.
You might be the best outboundSDR ever, but just don't put
Dave on a call with peoplebecause he can't talk, because
he doesn't know how to talk,because he AI is everything.

SPEAKER_00 (23:53):
He AI at everything.
Sounds like a genius.

SPEAKER_01 (23:55):
AI's everything.
Yeah, he's he yeah, send AI Daveto the meeting because regular
Dave just is not gonna be ableto come on.

SPEAKER_00 (24:01):
That's all that's gonna happen five years from
now.
It's like my AI being like, allright, man, let me talk to you.
And then other AI, like, I don'twant to hear this.
You know, it's like all uh allinteracting.
And this is actually a good, agood 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 likeuniversal principles, you know,

(24:23):
that you feel like or you know,use cases where you know AI is
just the superpower, likeregardless of like sales
context, like you know, Jake,here are like the top two or
three areas, and then we cankind of dive into to each one of
those.

SPEAKER_01 (24:39):
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 AIto replace the job that a human
is doing, I think you're gonna Ithink it's gonna blow up in your
face.
Um like um great example, uhvibe coding, hot, super hot

(25:00):
topic.

SPEAKER_00 (25:01):
Yep.

SPEAKER_01 (25:02):
You can't really release a vibe coded app into
production and think it's gonnawork great.
There was a there's a couplestories in TechCrunch in a few
weeks where it app blew upbecause you you just like, hey,
make me an app, and all of asudden there's security breaches
and everything blows up.
Um the experiences I had usingAI SDRs, full of code copilot,

(25:22):
it was terrible.
Um, you gotta empower youremployees just to work more
efficiently and just be likethis AI is meant to elevate you.
Let's take some of the mundanethings away from you and put you
on higher value work or morestrategic work.
Um, like in endless, right?

(25:43):
Don't spend all day just coldemailing people hoping they
respond.
The AI will fire off you know ahundred messages by the time you
personalize three.
Um, that is probably one of thebiggest ones for me, especially
when you think about all thethings you could do with it.
Um I think one of the otherthings is I think you should

(26:05):
test everything because it'smoving, keeping pace with
everything that's happening.
Like um OpenAI is announcementyesterday with the new uh that
again is gonna change absolutelyeverything.
You're like, how's that gonnachange my workflows?
How's that gonna change myinbound?
How's that gonna change my onwebsite conversations?

(26:25):
How's that gonna change myconversion optimization?
Like everything is changing.
So I think you just have to keepkeep pace.
I I've got three kids at home,and in the evenings I'm an Uber
driver and a bit of a DoorDashdelivery driver getting these
kids around.
I I don't have the time to evenkeep up with it.

SPEAKER_00 (26:44):
That's right, though.
I mean, yeah, and it's a a good,you know, we've got an AI
certification program uh that weliterally just launched for
leaders and for reps.
Uh six-week program, you'llbuild assistance, you'll
actually build workflows in inAiden or whatever platform you
have access to.
So, and and I was I was talkingto someone yesterday, and it's

(27:04):
like, well, Jake, what you know,how should I think about this?
And I I basically said, youcan't afford not to learn this.
Like, I think we all have torealize like we are all going
back to school, and you have todedicate the time, you know,
like you have to dedicate thehours to learn this stuff.
And to your point, if somebodyyou know runs a consulting firm
that does this, you know, allday long.

(27:25):
Somebody asked me in a session acouple 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'mdrowning.
Like I still feel like I'm not.
And and I always feel like Ican't, but I know that you just
have to keep paying attentionand that we have to, you have to
in today's day and age bededicating time.
I don't care if it's an hour aweek or two hours a week to

(27:48):
getting better because thistool, and very quickly, if
you're a a B plus player, a Cwho's really, really good at
leveraging and contextualizingdifferent ways to leverage AI,
will just outpace you.
Like they'll just be able tomove at just such a speed that,
like, yeah, David's, you know,technically better, but Jake is

(28:11):
8x more productive.
So I sorry, David, like if youdon't, you can't keep working
like this.
Like I can't employ you.
And and I feel like that's thearea of opportunity for a lot of
these folks is just to learn thethe of how to try to stay up to
speed, you know, and just makingsure you're taking the time, and
especially for all my leadersout there, you know, where I
feel like our time inparticular, like you said,

(28:31):
you're in an Uber and you know,DoorDash, and I can I I've got
two two young kids, so I canrelate.
Um it's it's uh it's tough, butI would just I would just
caution everyone, it'snecessary.
Like, yeah, you can't again,like the you can't not know,
like, okay, well, what whathappened here and what did what
happened?
Because I think what happenswith a lot of salespeople, once
they once we start to talk tech,salespeople's eyes just glaze

(28:54):
over.
And it's like, wait, I I got acode.
It's like, no, you don't.
But if you can understand howall these things work together,
you can start to think of theart of possible.
And that's really the skill setthat I think is creativity,
strategic thinking.
These are the ones that AI isnot going to be able to
replicate.
It can be a thought partner andit is creative, but you know,
creative ways to apply it.

(29:15):
Um, you know, and you know, youmentioned a lot of these use
cases too, about like where toapply it.
And and my question kind offollowing up here is what's too
far, right?
So, like what are let's what arelike what are the red flags?
Like, what are the specificsigns?
It's like random insights thataren't actually applicable.
That's a good one.

(29:35):
But you know, uh, how shouldpeople, if they're listening to
this, like, okay, like wherewhere is that line?
Because it sounds like uh, youknow, I want to use AI to get to
this point, but then I need toturn my brain on and do this.
Uh where do you feel like thatflag is of like, man, you gotta
make sure you're not doing thesethese things?
I always say copying and pastingAI, that if you're copying and

(29:56):
pasting AI, that is the surefireway to be unemployed in the next
two years.
As a part of it.
What else?
What are some of the other usecases where you feel, you know,
hey, avoid this or you know,make sure you're always doing
this manual-ish?

SPEAKER_01 (30:14):
My kind of rule of thumb is I avoid trusting AI
fully where I don't have the rawskill 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 andI'm just gonna trust that the AI
is doing the correct thing, andthen I'm gonna send that to my

(30:34):
boss or to a client, like you'relike, fuck peace.
Hopefully I'm done.
And I think that's with everyeverything, 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'sdetected in an error.
And then I'm like, well, thenwrite a prompt to fix the error,
and then it writes a prompt tofix the error, and then it fixes

(30:56):
the error.
But I have no idea what theerror was.
I have no idea how to fix theerror.
I don't even really know how toprobably look in the code base.
Like I'm I'm just blind trust,and I think it's in every
vertical in your in yourcompany, whatever you do.
If you don't understand how todo the job to get the right
output on your own, even if it'sgoing to take you three hours or

(31:19):
five hours, you can't just go inthere and blindly trust AI to do
it accurately because it's youyou just can't afford to screw
that up.

SPEAKER_00 (31:29):
That's such a good call out.
That's I I haven't heard anybodyarticulate that, um, which is
you know you're going too far ifyou find yourself consistently
blindly trusting and it's notsomething that you know how to
do.
And you know, you're having AIcheck its own AI, which look, in
certain cases, that's okay.
But if you also to, you know, ifyou don't have an understanding

(31:50):
of what good looks like, umyou're gonna have a real tough
time spotting when AI is fallingdown, or where AI is just flat
wrong, or AI it doesn't haveenough context because you don't
have enough context.
And so because you don't haveenough context, you're going
down, you're you're going eastand you should be going, you
know, northwest, for example.

(32:10):
Yeah, but I think that's areally good call at David.

SPEAKER_01 (32:13):
Yeah, I'm not great at prompting, and I don't know
what the output looks like, butF it, here we go.
Like you just I think you couldend up in a lot of hot water.
And um prompting is obviouslysuch an important skill set.
And it's like I took my you know100-hour course and did all the
things, and I'm still not thatgood at it, to be honest.

SPEAKER_00 (32:34):
But yeah, what we find consistently, this is kind
of a tactical tip for everybodyout there.
The most important thing is weare just so used to speaking to
machines in five words of brokenEnglish in Google, right?
Like that is most of our how ourbrains are are hardwired, you
know, to to and so we areunbreaking the pattern of like,

(32:55):
no, give it another sentence andanother sentence and then ask it
to go deeper and give it anothersentence and another.
And so I think for a lot ofpeople, just understand we're
we're rewiring the way that weinteract with machines.
And I think that that's where Ifeel 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 moresentences, more context.

(33:15):
And and again, to your point, Istill don't think I'm a 10 out
of 10 at this by any stretch ofthe imagination.
But um, we have to get betterand better at again, giving the
context.
If you can't give the context,or if you're giving surface
level context, you're gonna getsurface level insights and
answers.
Like that's what's gonna be.

SPEAKER_01 (33:31):
Yeah, but the machine's also gonna solve the
problem the same way you do.
Right?
It it could look at the problema completely different way that
you've never even fathomed.
And therefore certain you'regonna have a different output.
But again, context obviously isthe most important thing.
And you know, I want to do this,this is what I need to do, ask
any clarifying questions.

(33:51):
In doing that, you're gonna actlike this person.
This is my goal, pop, pop, pop,pop.
I just write it forever, andthen you'll get there.

SPEAKER_00 (33:59):
How can okay, this is a deep one.
If I'm early in my career, whatam I gonna do?
Like, okay, if I'm 23, okay, I'm23-year-old Jake.
I just graduated from let's gosomewhere cool.
I go, I went to like Ole Miss orsomewhere.
I don't know.
I live in Austin now.
Ole Miss just looks like a coolplace.
I don't know.

SPEAKER_01 (34:17):
I I agree with you on that one.

SPEAKER_00 (34:18):
You know, like, okay, I just graduated Ole Miss.
I got a marketing degree, andyou know, I did a couple
internships, I have a year ofexperience.
You know, how how does thisnewer sub, I'm gonna say
sub-five, sub-tenure experience?
Um, you know, kids coming out ofcollege are learning the Gen AI,
you know, in class, right?
How do I get context?

(34:40):
How do I, how can I use AI toget context without having as
much experience as you and Ihave?

SPEAKER_01 (34:49):
The I would say find a company where you are dialing
for dollars.
Like you are on the phones, it'syou're not cheating behind a
keyboard, and you have toactually learn skills, real-time
objections, and actually talk topeople.
And you need to bust your assharder than anyone else there to
get your stripes so that you cantalk, actually talk to people.

(35:13):
Yeah, it's it's a it's gonnabecome a lost art because we all
just hide behind a keyboard.

SPEAKER_00 (35:18):
That is good.
I didn't know where you're gonnatake it, but that was that's
exactly right.
Like I that's exactly what I wastelling that guy earlier today.
I was like, dude, the and youknow the answer is hard work.
Like the answer is you have youneed to go get it.
And and if you're at a place, Itell any seller listening to
this, listen to what that youknow, what David just said and
what I'm about to say.
If you are at a place that istelling you to hit send all on

(35:39):
templates, if you are at a placewhere they view the first
interaction with a potentialcustomer as a qualification
call, you need to runimmediately.
You are literally learningnothing.
You are not learning how tointeract, you know, you are not
learning how to consultsomebody.
That is the future.
The only future is consultativeselling.

(36:00):
And I don't care, you can callit spin selling, I don't care
what methodology you have, butthe only future is a human being
who can add so much value in thequality of the questions that
are that can be so nuanced thatAI might not pick up on.
They know the industry, they youcan connect.
Oh, hey, David, greatconversation.
Oh, hey, we work with six otherPSG companies.
Do you know Mike over at Yoda?

(36:20):
Like, that is it.
And so if you are in a sales joband you are not doing what I
just said, you have to leave.
Like, I don't, I don't know likehow else to say it.
David, you tell me what youthink.
But that that to me is where Ifeel like in three, four, five
years, you're gonna have ageneration of sellers who are
not going to be employablebecause they're not doing the

(36:41):
hard work, which is what youjust said.

SPEAKER_01 (36:43):
Yeah, well, what if the AI that I use that failed
miserably stops starts beingsuccessful?
And I don't need to hire youfresh out of college because
Dave, my AI avatar, who looksjust like me, talks just like
me, sounds just like me, can doit for me until I physically
need to show up at your office.

(37:04):
Like that's that's not out ofthe realms of possibility.
Like, why in three years, fiveyears?
Why why couldn't that happen?
I think 11x does did have avoice salesperson that I tested,
and I was like, this isterrible.

SPEAKER_00 (37:20):
Like, get there.
It'll never be worse.
I said that AI will never beworse than it is right now, and
it's pretty awesome right now.

SPEAKER_01 (37:28):
It's pretty amazing, it's pretty awesome as a part of
this for absolutely everything.

SPEAKER_00 (37:34):
Everything, right?
And that's it.
That's again with a lot ofpeople like AI.
Yeah, think about it.
It's it's again, I was talkingto right before we hopped on, I
was talking to a client of oursand we're doing kind of an
executive brief.
And I was like, which you haveto, you know, it's like, okay,
so you know, do I hire this ordo this?
I said, uh go look, you have torealize you're never going to
stop for the next two years.

(37:55):
All we are going to be doing asleaders is retraining every role
in our go-to-market teams how todo things a different way than
we all learned that made ussuccessful.
And so you have to realize thisAI journey that you're going on,
whether you're a frontlineseller, a leader, CEO, PE firm,
whatever, is we are going on amulti-year journey to completely

(38:16):
refactor the way that we solveall of our everyday problems,
whether that's an assistant thatwe interact with, an agent
that's doing things for us onthe side.
And so that's where, you know,you've got to just sign up for
the long haul.
Because to your point, as itevolves, if you're trying to
comprehend, you know, what we'retalking about a year from now,
and because you didn't investback here to kind of start to

(38:38):
understand or dabble, it'syou're gonna have a lot of
trouble.
You know, you if you're ifyou're not investing, I and that
that's really where, you know,I'm worried.
And this is actually a goodsegue.
We're almost at time here, um,which is what do you see as
next, right?
As AI gets better at mimickinghumans, does authenticity get

(38:58):
harder?
Does it get easier?
You know, where do you see thisgoing?
You know, whether it's with yourgo-to-market teams or, you know,
with your customers, and and howyou are going to help to guide
them through, you know, thisauthenticity, you know,
challenge.
Um, and you know, the only wayto grow their business or to to
grow their brand will be to beable to stand out whenever

(39:21):
everyone's using this type oftechnology.

SPEAKER_01 (39:24):
Where I see it going and where I want it to go are
two different things.
Where I see it is it's justgonna go, it's just the pace.
Everyone's like, oh, we're sobusy, we're so busy.
Well, you're gonna be busierbecause it's just everything's
gonna go faster.
Um, where I want it to go, whereI love to see it go, and I'm
kind of seeing it in in justgeneral, right?

(39:46):
I'm 44.
Um, a lot of my friends aremoving off social media and
going back to relationships,actually really spending time to
connect with people.
And like they're they're kind ofjust in the irony, of course, is
I have an influencer marketingsoftware that uses AI.
I trust me, I that's not lost onme.
But my my friend group isthey're like, no, I'd rather,

(40:08):
I'm I'm just not interestedanymore.
I'm really focusing on stronger,stronger relationships and just
being present, like going to ashow and actually watching the
show, not filming the show andwatching me filming the show
versus like being at the show.
Um, I I would love to see abyproduct of the pace at which

(40:28):
AI is happening.
More and more people go back topeople.
I mean, like, look, I I want myrelationships.
I built my career in this space.
I can call Doug and Jim and Jakeand Dave, and I could like, I
don't know.
That's just who I am as aperson, though.
I'm the I love going on the roadfor work.
I love going out for dinner.
I love building relationshipswith people.

(40:49):
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 belike, I really miss talking to
people.

SPEAKER_00 (41:02):
Like, I think you're right.
I think we're swinging backthough.
I I agree with you 100%, man.
I I actually feel like what AIlet me tell you how I see this
manifesting in my own company aswe're kind of AIing a lot of our
work.
We're there's two things thatare happening.
And one might becounterintuitive to what you
just said.
We're actually having lessmeetings.

(41:23):
And and and but but what that'sdoing is freeing up people time
to like have space to think andto work because I don't need to
follow up with you on this thingor check in or do that.
And so then when we are, youknow, again, because we are
busy, but then when we aremeeting, I feel like the quality
of the interactions are better.
There's less catching up and youknow, covering basic stuff.

(41:44):
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'slike we have like 10x more
meetings than people had in the60s, which is like as wasn't it
supposed to go the other way,you know.

SPEAKER_01 (41:57):
Like you like we all work as same creeping.

SPEAKER_00 (41:59):
We've got more tech now.
But but I feel like it's it'sit's it's helped there.
And I and I think that thatcould 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 dumbblocking and tackling stuff that
sucked that extra 45 minutesevery Thursday night or X amount
a week and logging my expensereport or you know, if I as we

(42:24):
get rid of that, I actuallythink it will create more space
for us to think and interact ina in a in a more human way as a
part of it.
So I actually I I see thatcoming back and uh you know,
certainly to to some extent, youknow, around people wanting to,
you know, interact more, be morepresent.
And and I think hopefully if wecan automate that busy work,

(42:46):
truly busy work, then we canspend more time thinking, which
I think is where most of uswould like to live, but we've
just been so conditioned to liveon the wheel that we we're not
taking the time to build systemsand processes that will ever get
us off the wheel.

SPEAKER_01 (43:01):
Yeah, and you said the dirty word for every
salesperson is I gotta do myexpenses.
Like, that's what AI.

SPEAKER_00 (43:07):
You know what it's your expense report is a part of
it.
That's the beautiful part aboutbeing a CEO, David.
I do not have that problem.
Like, I create that problem formy team.
They're like, Jake, please stop,use this, not the Amex.
I'm like, it's happening on theMX.
I'm probably sorry.

SPEAKER_01 (43:20):
Oh we must have the same people.

SPEAKER_00 (43:24):
Exactly.
Hey, this is my one thing I get,okay?
The other rest of the time, youknow, I'm catching all the you
know, all the you know what, andlight, you know, putting out the
fires.
But but no, this was awesome,man.
I think we covered a lot ofground here.
I think this conversation aroundwhere the human exists in the
process today, um, how we shouldbe thinking about AI, I think

(43:45):
we've covered a lot of ground.
And I think, you know, what Ireally enjoyed about this
conversation is I think we gotreally tactical too, to where
hopefully everybody listening isgonna be able to say, ooh,
here's like one thing or twothings that David said or Jake
said that I'm like, I can nowthink about maybe reworking how
I'm using AI, you know, whereI'm showing up in my journey
with customers and how I'maugmenting with AI.

(44:06):
So I think, you know, I thinkpeople are gonna get, you know,
a lot out of the episode.
And David, you know, where wherecan people find you, learn more
about you know what you'rebuilding?

SPEAKER_01 (44:16):
And I think LinkedIn is definitely the best place uh
uh for me.
I'm relatively active on there.
Yeah, yeah.

SPEAKER_00 (44:27):
That's how we got that's how we got connected.
And we'll make sure we'll we'llput a link in the bio for you
uh, you know, as well too, andyou 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 lovethe dialogue.
It's fun to have a quick reallythe future-looking but also
tactical conversation.
So I really appreciate it.

(44:47):
Thanks, man.

SPEAKER_01 (44:48):
Yeah, well, I really appreciate having me on, and I
really enjoyed this as well.
So thank you very much.

SPEAKER_00 (44:52):
All right.
Thank you, everyone.
That's a wrap.
We will see you next week on theAI Powered Cellar.
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