ClickUp’s $1M Bet on the 100× Marketer

Summary

Podcast Summary: ClickUp’s $1M Bet on the 100× Marketer

AI-Driven Marketer: Master Practical AI Marketing Skills
Host: Dan Sanchez
Guest: Ken Fre
Date: July 24, 2026

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Episode Theme & Purpose

Dan Sanchez and Ken Fre dive into ClickUp's much-discussed "100X Marketer" job post—a bold move promising a path to a $1 million compensation for a solo “artisan” marketer who can replace an entire team by orchestrating AI systems. The episode explores whether this is a sign of the future for marketing, analyzes the feasibility and implications, and offers candid thoughts on what it means for marketers’ careers.

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Key Discussion Points & Insights

1. Setting the Stage: What is the 100X Marketer?

• ClickUp’s Job Post:
  • ClickUp (project management software company) posted a role seeking a single “artisan” CMO who would own the entire marketing function, orchestrate AI at “hyperspeed,” and produce output equivalent to a team of 50.
  • Directly quoted:

    “One person who builds the systems that produce world class marketing at scale and reviews everything with taste sharp enough to know the difference between great and garbage.” – [01:00] “…operates AI systems like instruments. Fast iteration loops, rapid evaluation, continuous course correction which takes a team of 15 six weeks takes artisans days…” – [02:18]

• Role Expectations:
  • Not managing a team—full end-to-end ownership: brand messaging, campaign strategy, social content, email, content pipelines, and review systems.
  • Compensation path up to $1 million, not guaranteed at start.

2. Initial Reactions: Is This for Real?

• Skepticism and PR Stunt Hypothesis:

  “I thought it was a prank.” – Ken [04:58]

  • Both hosts wonder if this is a genuine job or clever PR.
  • Concern whether one person can realistically replace an entire team by leveraging current AI tech.

  • “This person’s going to be set up to fail because I don’t think the tech is there yet to do everything that this person wants to do.” – Ken [05:16]

• Potential Impact on Current Marketing Teams:

  “What are all of the marketing people at ClickUp right now thinking?…Should they start looking for jobs right now?” – Ken [08:45]

  • Anxiety about the internal messaging and morale for current staff.

3. Polling the Community: Industry Sentiment

• LinkedIn Poll Results (74 respondents): [06:16-07:08]
  • Absolutely: 12%
  • Yes, but with sacrifices: 18%
  • Maybe in a year or two: 14%
  • Absolutely not: 54%

  • “Well over half are like, no way, not even close. Just no, hard pass.” – Dan [06:52]

• The Consensus:
  • It’s not something people think possible—now or soon—without major compromises in quality, depth, or both.

4. Feasibility: Can One ‘Super Marketer’ Replace a Team?

• Skill Set Requirements and Rarity:

  “There’s only a few that are this good marketing-wise and even less that have serious AI chops that can orchestrate agents…” – Dan [10:10]

• Why Would Such a Person Take the Job?

  “If you’re that good at marketing and that good at tech, you already freaking figured out how to do it solo… Why the heck would you work for ClickUp?” – Dan [11:36]

• Scale and Review Bottlenecks:
  • Reviewing AI-generated content (especially video) at required scale is humanly overwhelming.

  • “There’s not enough time in the freaking day to watch all the videos. Even at 2x.” – Ken [21:26]

  • “That’s the problem… There’s just not enough hours in the day for one person.” – Dan [22:13]

5. The Limits and Tradeoffs of AI Marketing Systems

• Sacrifices in Human Touch:

  “There’s a human element… I don’t think AI could ever pull that off. That needs a human touch for comedy and jokes and just the way they frame things.” – Ken [20:20]

  • AI can’t replicate all elements of humor, brand voice, or contextual cultural understanding, especially across diverse formats.

• Quality vs. Volume:

  “If anything, I want to slow content down and focus. Like, what can I do that no one else can do?” – Dan [35:26]

• Ethics and Authenticity Concerns:
  • Discussion of unethical solopreneur AI marketing example as a cautionary tale—use of fake endorsements and testimonials [27:35].

6. AI Skill Building and Career Takeaways

• Skills Stack:
  • Keep building expertise in existing marketing verticals with AI—stack new skills atop foundational ones before jumping into others.

  • “Continue your expertise, whatever it is, use AI to make that faster, more agile—then move to another adjacent skill set.” – Ken [31:22]

• Managing Up & Internal Reality-Checks:
  • Marketers must “manage up” with leadership—set realistic AI expectations internally.

  • “If you don’t do that…people are all of a sudden going to feel the pressure that they have to perform in 100x when the tech is not even there yet.” – Ken [32:10]

• Focus on Bottlenecks, Not Just Productivity:

  “The way you become a hundred x marketer is not by orchestrating agents and systems, it’s by fixing bottlenecks. Because if you fix enough of the bottlenecks, you could 100x them.” – Dan [35:06]

  • Use AI to unlock constraints, not just mass-produce content.

7. The Human Side: Role of Decision-Making & Burnout

• Decision Fatigue:
  • Solo “100X” marketers would face thousands of decisions daily—a massive source of burnout.

  • “It’s not that you might not have the expertise, but the 5,000 decisions that you have to make every single day for every little piece is going to be exhausting.” – Ken [36:18]

• AI Can Multiply Work, Not Always Reduce It:

  “It seems like AI is multiplying work. It ain’t doing the opposite.” – Dan [37:40]

  • The reality is that top AI orchestrators are working harder, not less.

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Notable Quotes & Memorable Moments

• “I love that they’re pushing into it… It is an interesting idea. I think eventually agents will be more and more capable. So, in time, maybe as agents get better… but for now, there will still be sacrifices.” – Dan [19:41]
• “If there’s a CMO who could do this, why would they come work at ClickUp? They’re already doing their own thing.” – Ken [10:47]
• “No human can juggle that much context in their brain effectively. Also, if I'm replacing 50 people, I’d certainly need more than $1 million a year.” – Finn McKenty (quoted) [24:24]
• “I rarely get stuck anymore because AI is able to get me unstuck so much faster…” – Dan [34:43]
• “As you’re fixing the bottlenecks and using AI, it is becoming so much easier for you to lose being in the driver’s seat… you’re supposed to be driving the whole situation.” – Ken [35:37]

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Practical Advice & Takeaways

1. Keep learning AI, but stack new skills on what you’re already good at before shifting verticals.
2. Manage leaders’ expectations—keep them realistic about the limits and actual uses of AI marketing.
3. Focus AI efforts on fixing business bottlenecks rather than mass content production.
4. Beware of burnout and context overload—no single person can (or should) replace the nuanced contributions of an entire marketing team.
5. Stay human: AI is a tool to enhance, not replace, creativity, artistry, and strategic judgment.

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Timestamps for Key Segments

• Job post reading & breakdown: [01:00 – 04:46]
• Initial reactions & skepticism: [04:58 – 06:16]
• Industry poll results & analysis: [06:16 – 07:18]
• Deep dive: feasibility discussion: [09:00 – 14:32]
• Review bottleneck & practical limits: [21:15 – 22:44]
• Soft skills, managing up, bottleneck focus: [32:07 – 35:05]
• Burnout, decision fatigue, and human-AI balance: [35:37 – 38:22]

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Overall Tone

Candid, skeptical, humorous (“job posting the thousand-x CEO”), occasionally irreverent, but ultimately constructive and realistic; both hosts emphasize humility, continual learning, and pragmatism as AI continues to reshape marketing.

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For marketers: ClickUp’s post is a loud signal—AI will keep accelerating, but excellence requires more than just tech chops or tool orchestration. Focus on thoughtful skill-building, human judgment, and tackling real business problems. The future’s bold, but don’t believe every headline hype.

Transcript

[A]

Welcome back to the AI Driven Marketer. I'm Dan Sanchez and I'm joined by my friend Ken Fre.

[B]

Yo, what's up bro?

[A]

And today we're talking about being a hundred X marketer. If you didn't see from LinkedIn posts and just general news going around. Is that ClickUp? Yes. That big software company that is like a big.

[C]

I don't even know what to explain.

[A]

ClickUp, they kind of do a little bit of everything these days, but it's kind of like an interactive, I don't know, Excel sheet in the sky kind of a thing.

[C]

That's what they started as and now

[A]

it does a lot of stuff. Project management system. Is that fair, Ken? I mean they're table competitor.

[B]

I'm biased. ClickUp management system known to make on.

[C]

I tried it once and it was clunky as all get out but it's a big company.

[A]

Lots of people love ClickUp.

[C]

It's fine.

[A]

It's up there with Airtable and Monday.com.

[C]

it's kind of in that realm.

[A]

But they've gone all in on this AI deal and they recently posted a job description which is kind of causing a little bit of a stir. My good friend Ashley Foss sent this to me and she's like, dude, what do you think about this? And I saw it and I was like, what? And I was like, well, maybe. But with that in mind, I just need to read it to you. So I'm going to read it here on the podcast and then we're going to talk about it because this is kind of a big marker of what we could be looking at for the future. But we have to ask the question, is this an indicator of what's to come? Is this where we should be thinking about aiming our careers as marketers? That's what we're going to talk about. But first let me actually just read the job description. Okay, so it starts off from ClickUp and the title of this job title is 100X Marketer Chief Marketing Officer. Okay, so that's the title. And then we see from zeb Evans, the CEO we're executing on the 100x.org. I'm looking for one person to own the entire brand marketing function at ClickUp, not manage a team of 50, not sit in meetings all day, not write brace for other people to execute. One person who builds the systems that produce world class marketing at scale and reviews everything with taste sharp enough to know the difference between great and garbage.

[C]

Good copywriting right there.

[A]

Good alliteration. We call this person an artisan. What is an artisan? An artisan is not just a quote unquote good marketer. An artisan is someone with whose taste and judgment are so refined they can orchestrate AI systems at hyperspeed while maintaining quality that lesser teams can achieve at any speed. Taste. They know what good looks like before it exists. They can evaluate 50 AI generated options and immediately identify the two worth publishing. They're internalizing the craft so deeply that quality assessment is instantaneous Judgment. They know what to build, not just how they understand the audience. The market, the trade offs is well enough to make high stakes calls without committees. Speed of orchestration. They don't just prompt AI, they op. They operate AI systems like instruments. Fast iteration loops, rapid evaluation, continuous course correction which takes a team. 15 team of 15. 6 weeks takes artisans days ownership, breath. An artisan owns a surface end to end. Not the social part, not the email part, the whole thing. Strategy, systems, execution, quality. Fewer people means fewer handoffs. Fewer handoffs means faster better output. This is the marketing equivalent of what an A10X and engineer does. Own an entire product surface. I did execution live. The only two things that matter. Yeah it says only two things that matter is systems.

[C]

And I'm going to spare the description of systems.

[A]

Can you or essentially can you build a mark marketing system that compound and two review. Can you judge quality at absurdly high bars? What you own, Brand messaging and positioning for everything ClickUp puts into the world. Campaign strategy, creative direction and systems that execute execute them. Social media presence, content and engagement, email marketing drip campaigns and lifecycle flows. Content production pipelines across all formats. Quality gates.

[C]

Nothing ships unless it meets your bar.

[A]

You build systems that do it. You are the taste. The agents are the hands. So this is the job description. It is up to a CMO title so not guaranteed CMO title and you get about a million dollar comp growth growth path. So it doesn't even guarantee a million

[C]

dollar salary at first. A million comp growth path as in

[A]

you'd grow into a million dollars.

[C]

So you probably wouldn't start that at the beginning.

[A]

And there's a few other things on this.

[C]

I skipped over a couple paragraphs explaining

[A]

systems and review but that's generally the resume. The hundred x marketer Ken Initial reaction to this crazy job post.

[B]

I thought it was a prank.

[A]

I thought they were just.

[B]

I was like well ClickUp does a bunch of random stuff. And then I was like it's gotta be it. It's gotta be like them just messing with us.

[A]

It could be a PR Stunt, that's for sure.

[B]

I wouldn't be surprised. I would be like, okay, cool. Like, it's a fun PR stunt, but man, I, I'm honestly, my, my, the, my real hot take was that, like, this person's going to be set up to fail because that. I don't think the tech is there yet to do everything that this person wants to do. And you got to find someone who's such an expert at so many different areas of marketing to be able to pull this off.

[A]

Well,

[B]

that's my initial. I mean, I could go into my own rant, but I'll let you give your input.

[A]

I went and polled the audience over on LinkedIn and we've had 74 votes. Not a great showing on the poll, but not bad.

[C]

I don't know, I haven't been regular

[A]

on LinkedIn lately, so my posts haven't been getting as much reach. And that's okay. 74 is good enough though. And I asked, I asked the crew, could a super marketer with insane tech chops replace a marketing team of 50 people?

[C]

Okay.

[A]

And then I also gave some context. This is like what ClickUp's hiring for. And maybe it's just a PR stunt.

[C]

What do you think? And.

[A]

But the options I gave them were four different options. Absolutely, yes, but with sacrifices. Maybe in two year or two. And then absolutely not. And the results are as following. Absolutely got 12%. Yes, but with sacrifices got 18. Maybe in a year or two got 14. And absolutely not got 54. So well over half are like, no way, not even close. Just no hard. No hard pass, you know, and a little chunk.

[C]

15%, it's not a big chunk.

[A]

Said maybe in a year or two. They're like, ah, someday maybe because they're

[C]

seeing where it's going.

[A]

I said, yes, but with sacrifices.

[C]

And, you know, a very.

[A]

The smallest portion of people. 12% said absolutely not or absolutely. So it's kind of like I'm kind of in the Absolutely yes, but with sacrifices and like asterisk, major, massive sacrifices.

[B]

Sure.

[A]

Could it be done?

[C]

Yes. Is it the best?

[A]

Is it worth it? No.

[B]

And I would say, like, if you had a marketing team of three, it might be better. But like, absolutely right.

[A]

Like 50.

[B]

I'm thinking of the whole architecture. You have someone who's so specialized in certain areas that like, you have a great copy copywriter, a great media buyer. You have certain people that could do such extreme, specialized skills. It's almost like saying to the CEO, hey, you don't need a cmo. You could do it just do it. Have AI do it. Why don't you just have someone set up the system and then you run it? It's that logical fallacy. Like I just gotta say this before I'm done by it.

[A]

If I were ClickUp's competitor, wouldn't it be funny if you were like airtable and you're like job posting the thousand

[C]

x CEO

[A]

just as like a reverse stunt? If it is a PR stunt, you

[C]

know, that would be really funny.

[B]

Well, you know, like there's two things that I that come to mind on the job description. They said fewer hands off means faster, better output. And I'm like, yeah, but that you're assuming that the CMO has the ability to interpret all that output. Like if they don't, it's going to come out like garbage. And it's sooner or later. It is. The second thing that I thought when I was reading this. What are all of the marketing people at ClickUp right now thinking? All their employees, if they see this.

[C]

Oh bro, I didn't even think about

[A]

the indicator of like, we don't value

[C]

you if you're not one of these a hundred X marketers.

[B]

Yeah, it's just like, should they start looking for jobs right now? Should they be on the hunt? Are they in on it? Like, there's just stuff.

[A]

A lot of tech companies have already

[C]

been sending the signals of like, we're going to be 100x orgs, we're going to be AI first, blah blah blah. This has been happening for over a year now.

[A]

So like if you work in tech, like, come on, the writing's been on

[C]

the wall that this is the expectation now. So everybody better be token maxing even if productivity isn't increasing just for the appearance of token maxing productivity.

[A]

Sorry. If you're working in tech, you've been

[C]

hammered lately because of this stuff.

[A]

So. But everybody else has to think about it because this is sending a signal. And other people, CEOs specifically start to think, borrow from other CEOs. This is going to have an impact even if it doesn't like have the, like everybody starts hiring it. It's going to start making CEOs think how they evaluate marketing teams because of stuff like this. I do think it's actually possible even for a company the size of ClickUp, which they need a lot of stuff.

[C]

They have a lot of social accounts, they have a lot going on.

[A]

I just don't think it'll be very good even if that marketer is like world class. Like so this, this person Also, even if it's possible, this person is going

[C]

to be incredibly rare.

[A]

Like, I've interviewed probably hundreds of marketers, lots of fantastic marketers. There's only a few that are this good marketing wise and then very. There's even less that are this good and have serious AI chops that can orchestrate agent. Shoot. I struggle to orchestrate more than one

[C]

at a time, let let alone create

[A]

these crazy loops that now loop.

[B]

Loop.

[A]

Loops are old now.

[C]

Do you hear what the new thing is? Grids.

[A]

I don't even know what that is yet.

[B]

Grid.

[A]

But people are like, loops are out, grids are in.

[C]

I'm like freaking, what does that even mean?

[A]

You know, have you heard?

[B]

I have not heard of grids. But you know, the thing I'm thinking about with this scenario is again, if there's a CMO who could do this, why would they come work at ClickUp? They're already doing their own thing.

[C]

That was my thought too.

[A]

I'm like, okay, even if you got a million dollar compensation package out of

[C]

the gate, like a million dollars a year, I don't know what, how much is that a month?

[B]

What? It's probably about a hundred k a month.

[C]

Almost a hundred k a month. Yeah, it's a little less, like 90k a month. It's so much money.

[A]

But even if you did, that person, if you're that good that you could actually crush it, is probably a multimillionaire already. Let's be honest. If you're that good at marketing and that good at tech, you already freaking

[C]

figured it out how to do it

[A]

solo and scale a little small organization that creates a lifestyle that you want. Why the heck would you work for ClickUp?

[B]

Yeah.

[A]

And all of a sudden have to bend to the whims of the CEO? Even if you report directly to the CEO, which you do in this position.

[C]

Right.

[A]

So it's like, like, how are they going to tempt this person now? I know because I posted about it and I asked this question. You know, there are a few people that were like, yeah. And I'm like, well, some of them. I'm like, well, like, are you. I don't know if you're this person. And some of them I don't know because I didn't know them at all. I'm like, well. He's like, yeah. And I'm like, did you apply?

[C]

He's like, yep.

[A]

I'm like, well, I don't know you. So I can't evaluate whether you got the marketing and the tech chops, but you know, million dollar comp packages will attract people, but will it attract the

[C]

person that can actually do do it?

[A]

Yeah, I think they probably will try to hire this person and see what they can do and it'll be very interesting. I'd rather do it as an experiment rather than, I don't know. Are they going to let go of their whole marketing team?

[C]

I don't know.

[B]

No. I mean I would assume that they would have this 100x marketer like doing their own thing. They'll have the other. They'll pretty much, if they were smart,

[A]

but fire the whole marketing team and be like, oh shoot, maybe we can't

[C]

outsource the whole marketing team to one person yet.

[B]

They would split, test it like split and check like who does better at what. But I, I, I have a feeling that this is a little bit more of a extreme, you know, like let's just do a little PR stunt. This person may end up being a marketer. They may get rid of, say they have 50 employees, they might get rid of 10 because this marketer cannot do this. But to have just one person is. And with a $4 billion company, you gotta know there's so much moving parts that is like from an organizational and operational structure. It just sounds like this person would

[C]

be working like 24, 7, 365 and have a miserable life.

[B]

Yeah. Just to get everything set up. And they also have a similar one

[C]

because a company this big doesn't have a lot of room for failure. So if you post something and it's not great, people are going to point it out. You know, at ClickUp size they would. But if you were doing this solo, like it's a lot easier because if you miss with your systems then you know, you just recalibrate and try again. But like a company at ClickUp size, it's a lot of focus on every social post. It's a lot of, there's, there's, there's gonna be it that's gonna be tough to iterate on the systems.

[B]

You percent agree. They also have another role like this called the Hundred x Chief of staff.

[C]

I didn't look at that one, but apparently you were looking at it just before we got on. You're like, dude, they have a lot of 100x roles. I'm like freaking. I know they have 100x.org going on. So now I'm like, okay, they're really pushing here.

[B]

I would have a feeling that they internally are talking to everybody and saying, listen guys, we're just testing something. Your jobs are not on the line.

[C]

I hope that's the conversation internally.

[B]

I would hope, I hope.

[C]

But you know, bad leaders do bad things sometimes and just sort of like,

[A]

this is where we're going.

[C]

We're hiring these people and everybody, everybody else is like, what? I need to get my resume out and leave.

[B]

I can't have a Hydrax leader who can think like that. Like, Common Sense 101.

[A]

Like,

[C]

oh, man, it's going to be a click, a burn, I think. Let's. We'll talk about the good things in a second. There's some things that you really should be thinking about for this, but one more slam on this before we head into the good parts of it is you and I talked about this right, just as we started, but neither of us are fans of ClickUp, the software.

[A]

So like, okay, 100 they hire 100x marketer, who's probably got their own systems

[C]

and agents and things that they do.

[A]

Are they going to force them to use ClickUp? Because that would be part of the sell, right? Like, oh, you have to use ClickUp. So even if you do find the

[C]

person and tempt them with the compensation

[A]

package and they come in like, are

[C]

you going to force them to use ClickUp?

[A]

Because I doubt they do. I don't know any hundred X marketer slash tech people that are like rocking ClickUp as their main AI home base. It's all like Claude and MD files and. Or Open Claw, you know what I'm saying? Like, it's a collection of tools that. And they have to have a harness. And it's not.

[B]

ClickUp is not designed for it. No. And I, yeah, I would agree with you. There's going to be so many use

[A]

it as a database.

[B]

And you know, I will say I don't know the Clickups API. I will say that I've predominantly used it as the project management tool. And someone here might be like, well, that's why you don't like it because everything else is great. But I'm like, that's what ClickUp was known for, was like their spreadsheets. Then they moved to project management. Everything else has been like ancillary or they're like trying to get more money. But ClickUp is, I get why people like it, but it is clunky and

[C]

it is very clunky.

[B]

People who want to use AI do not like clunky. They like speed and efficiency.

[C]

Now the way they're positioning just to jump on ClickUp's website now is the software to replace all software. So this really is the goal that it's the database. I'm sure, I'm sure it's like, yeah, they're definitely trying to come after everything. So no, you're definitely, you're definitely going to have to use ClickUp. I'm like, dude, 100x marketer that's got all these agents orchestrated and tuned in. They're going to have to learn how to use your system. That's going to be tough because I haven't heard a single person in the AI space and I'm not like paying attention to everything. But I listen to a lot of podcasts, a lot of YouTubers newsletters. I'm trying to keep a pulse on the AI space and not. I like, I can't remember ClickUp being mentioned. Tell this job posting.

[B]

Yeah, I mean it looks like for ClickUp, if Go High level is the, the marketing SaaS product that can do all things. This is trying to be the, the operational side for a business. Yeah, that's what ClickUp is trying to. And I'm like, you're now going against Microsoft. You're going against, you know, just a whole bunch of different groups of people that I'm like, I mean it's a

[C]

big company, so a lot of people

[B]

do it and they might. But again, I haven't found anything that I've been like, this is awesome from ClickUp. There's other products that work way smoother.

[A]

So what I like about this job posting is one, it's. It's fun to see somebody push the

[C]

envelope and try radical things. It sounds like they're betting the whole org on it.

[A]

It's like, hey, sometimes bold bets win, sometimes bold bets sink ships. But it is fun to see someone. It is an interesting, I thought experiment to think like, oh, like what.

[C]

How would you orchestrate this?

[A]

Like, how could you do this right now? Like, it. It'd be fascinating if you're.

[C]

Listen, like, I'm almost tempted to just like interview three marketers to see how they would do it. Marketers that I think would actually be able to pull it off.

[A]

Like, okay, like there's going to be sacrifices because you can't automate. No matter how good you are with the tech and how good you are a marketer, there's going to be things that you're just going to be able to miss. Whether your agents get it wrong or they're just,

[C]

I don't know, like remember

[A]

one time I over automated infusionsoft and

[C]

we were working in higher ed and

[A]

the loop and it Got a little crazy and the, the audience kind of felt like you're feeling a little robotic. That's how it's going to feel 100%.

[C]

There's no way around it.

[A]

Like, you can't give enough voice and

[C]

brand and crap into context into it

[A]

to not make it feel like that. It's going to feel like that has

[C]

to at that scale.

[A]

But you know that maybe that's part of the jive. Like, I can get away with AI thumbnails on my podcast because it's an AI marketing podcast. So it's like it's, it's expected. So maybe they can get away with that because they're positioning themselves as like

[C]

the master database of all the AI

[A]

stuff and they can come across as

[C]

feeling a little bit more robotic. Like my thumbnails are fine being AI. And no, I don't pretend to be otherwise. Some other brands that I manage, like, I can't get away with that because their brands are more authentic. Like, I don't know, I can't say I'm inauthentic, but like their brand, because their brands are an AI, it would be perceived as inauthentic.

[B]

Yeah, they're more human. Human element.

[A]

Right. So like. But I love that they're pushing into

[C]

it and challenging it and coming up with the stuff. It is an interesting idea.

[A]

I think eventually agents will be able to be more and more capable. So in time you're like, maybe, maybe as agents get better and they have

[C]

access to more context and have bigger

[A]

context windows and more tools, they can

[C]

orchestrate things and spin off little agent swarms and accomplish things rel relatively well

[A]

in a way that's pleasing to you

[C]

because they know your taste and preferences.

[A]

Maybe today that's a sacrifice. A year from now, maybe, but there's

[C]

still gonna be sacrifices in the process.

[A]

But what would those sacrifices be?

[B]

Yeah.

[A]

What would they be leaving behind?

[B]

Oh, I, I feel like there's right now, because of the way I've seen the level of AI, it feels like they're sacrificing just about everything. Like I think their copy. I, if, if, you know, when I look at ClickUp social media, they, they do some funny reels or like some funny things that they do that I'm like, there's a human element to that, that whoever's doing the CMO role, like, I don't think AI could ever pull that off. Like that needs a human touch for comedy and jokes and just the way they frame things, I'm like, you're going to lose that, and I think that that's, I'm probably wrong, but I'm assuming that's actually worked in their favor that they, because they keep doing it. So clearly they got to have some metrics that this is working for them eventually.

[C]

Especially if you're doing a lot of medium video. And I don't know how much media and video ClickUp does, but I assume it's a lot, you know, with reels and all the video short posts and

[A]

video ads and YouTube and they do, they do.

[C]

I mean, I think they do even big commercials like on TV and all that kind of stuff too, because they're big enough.

[A]

Like, how do you, how do you

[C]

have enough time to even watch all the variations of those videos to find the ones that actually run? And then you need a certain amount of variations to run a split test. I'm like, there's not enough time in the freaking day to watch all the videos. Even at 2x.

[A]

You think about it, because AI is going to spit out 20 and you need to find like he even said, like you need to be able to look at all the different variations and then judge the two of the 20. Yeah, he even said 50 pieces of output and immediately know which two are worth publishing. But what if those 50 pieces of

[C]

content are all video and some of them are 30 seconds and some of them are five minutes? Oh, you're gonna be screwed.

[A]

How do you have time for that?

[C]

It takes too long to review everything.

[A]

And that's you, you become this massive bottleneck of review. Like that's, and that's the problem that

[C]

I'm like, there's just not enough hours in the day for one person to do this.

[A]

Now if you had only one person in charge of just video, maybe, but

[C]

that person's got to be in charge of more than video. We're talking about billboard size stuff. We're talking about design and social and image ads and emails and all kinds of crap.

[A]

So like in order to accomplish it, you have to scale everything way back into a meaningful amount of work and have to prioritize, which means you're doing less. Even though the AI agents can move faster, they can only move as fast

[C]

as you can review everything.

[B]

Yeah, My, my guess, there's, there's two guesses that I have on this. Number one is if they find someone, it's going to be a young person who, because they said like, experience doesn't matter, it's just your output.

[A]

No degree matters. No experience, no resume, no, yeah, no required.

[C]

No resume, no degree.

[A]

Just we want to see systems plus review.

[C]

That's it.

[B]

So I could see that there might be one guy who makes their career. This launches their career. Guy or gal. It launches their career. So I could see that. The second thing I can see is they're trying to find someone super high level. But at the end of the day they'll end up maybe taking over one division of marketing. Like they're going to be crushing it in copywriting, for example. And they might get there, but like. And that whole team maybe goes away, but they're not going to like replace everything tomorrow if they found someone. I just haven't seen AI be able to pull it all off.

[C]

Yeah. And I definitely can't pull off the video. The video part's really hard. But it takes someone working with it really closely and evaluating a lot of stuff to be able to put together one good video.

[B]

Yeah. And I don't know a lot of marketers who are great at video who are also great at like ads, copy, you know, like those are just two different skill sets that like.

[C]

And then like there's, there's probably out there. I, I can, I can think of. There's one person who commented on my post. Let me see if I can find him. Give him a shout out because what did he say it was? Where are you?

[A]

Finn McKenty.

[C]

Oh, man, I like, I love this guy. He's got great LinkedIn posts. Go follow Finn McKenty. He's probably one of my favorite followers on LinkedIn right now. He says his. This is one of the people that I actually think could do it. He says, no way. I am for sure in the top.01% of AI users in context of marketing and it's just not possible. I actually believe them. The technology isn't the issue. You could build whatever you want. It's just that no human can juggle that much context in their brain effectively. Also, if I'm replacing 50 people, I would certainly need more than 1 million a year. He's one of the guys that like, he's financially well off enough. He's like, I freaking would never do this even if he could do it. Um, but again, and he's. I don't think he has previous CMO

[A]

experience, but like he's worked for.

[C]

Is it Amber Crombie? Amber Crombie and fit creative live. He had a huge YouTube following in the hundreds of thousands for the punk rock NBA, his fun channel.

[A]

So like he's, he's got serious chops.

[C]

I've seen his posts. The Guy knows what he's talking about. He's really good. He could probably do it, but he's saying no way. He's one of the people I would have nominated for it to see if it was even in the realm of possibility.

[B]

Yeah, I'm with Finn. Finn is, Finn is smart. Like, listen to Finn. Yeah.

[C]

The question is, will it be available to do a year from now then?

[B]

Yeah, I, I, you know, I think putting a definite timeline might be hard, but I think that will be the future. I, I think at some point it'll be able to not be just like an intern level, it'll be able to be manager director level when you have the appropriate skills to function well. I think the discernment piece, you're still going to need someone with high level of discernment and a human individual to execute certain things about the business. I just don't see that going away. And then even just like artistic taste, all that stuff is needed. Like all of us know the basics of AI that you get what you put into it. So you just need those people who can put really good stuff into it to have great output.

[C]

Yep. There's, so it sounds like the consensus is it definitely can't be done. Now we did have a company, Solopreneur, that made a billion, that was worth a billion dollars, generating revenue in the hundreds, maybe over a hundred million dollars for sure. And it was worth over a billion. So we have our first billionaire solopreneur and I think he has his brother as like an executive assistant kind of a thing. So I'm still going to count that as a solopreneur. The problem with this company was on the marketing front, he generated a lot of fake AI testimonials and endorsements, which is very unethical, and was selling like kind of questionable GLP1 type products, which is a hot market. And he hammered it and did it and it's like, okay, but the first Solopreneur billionaire, while it's now technically accomplished, did it unethically in a lot of different ways.

[A]

So again, that's like it was possible,

[C]

but major sacrifices on ethics and integrity and quality and all that kind of stuff to the point where it's obvious because like you had like Professor Dumbledore giving endorsements with a fake looking Dr. AI photo, you know, so that's how they knew. They found a bunch of like funny names in there and tried to validate that they were real Facebook profiles and social profiles of all these doctors and they're like, this is totally AI. Slob. So. And that would, that's what would happen to ClickUp if they really try to push it. Now, I think based on what they're saying here, you're probably right. They're probably just going to give them a small section and then build it out. And then build it out and try to be like, that's the path, the million.

[A]

If you could get up to this

[C]

point, then you can earn a million dollars. But we're going to start you here at this comp package and we're going to give you this little section of the company to try to run with this. And we really want to see you scale this out. I think that's going to be the pitch and that's how they're going to keep themselves a little safer. Otherwise it would be way too risky.

[B]

Yeah. There's no way a $4 billion company would just get rid of their marketing team tomorrow and hire one guy. Like, maybe, maybe if the person. I'm going to be pretty blunt here, maybe the person's on crack, they would do that. But I think ClickUp has enough marketing chops that they wouldn't do that. That's just my guess. Like everything that they've done. While I may not be a big fan of their software, clearly they're smarter than I am because they have a $4 billion company. I do not. Right. And they have better marketing acumen. So I'm going to give them the benefit of the doubt in that aspect. I'm like, okay, there's a play here. And obviously we're talking about it. People are talking about it.

[C]

Yeah. But I think this sounds like one

[A]

of those things where they had an

[C]

off site brainstorming meeting and they were trying to come up with ways to become 100x org. They're like, well, let's find the best 100x talent out there and see what we could do. And this was, this was, this is coming out of one of those brainstorming meetings for sure. The question is like, what do we do about this? So let's get practical because I think people are going to continue to think this way. CEOs are seeing this kind of stuff

[A]

in their news feedback, which is going

[C]

to come back to us as marketers. And I think again, it's important to be honing AI skills and sharpening them and staying up to date. It's really difficult, like, even for someone like me, and I'm pretty technical. I like keeping up to date with it, but I can't keep up with everything. So, like I've just kind of honed into like Chat GPT and Codex now, the Chat GPT app with code mode I guess. And I'm using it more and more and I'm rebuilding my whole website and it's getting really exciting. I'm using Vercel. It's great, love it. And I'll be publishing a podcast on that soon on that process. So you need to be staying up to date and pushing the envelope with it and kind of just include, just don't stop, just keep learning. Try to do something new every, every week, every other week or so and keep pushing it. That's good. Don't fill the FOMO when you're like,

[A]

oh, I'm not spinning up agent swarms

[C]

and designing my own SaaS apps and all that kind of stuff like ah, like maybe build some little mini tools like keep going and just don't stop. And then eventually like what's hard now becomes easy a year from now. It used to be hard to prompt, now it's not. You can give crappy prompts and they still figure it out. Used to have to be super particular about how you talk to them. I spent hours refining prompts and instructions and now I don't. I just word vomit voice command into it and call it good, because that's easy now. But now I'm learning how to orchestrate systems and code and think through like, what do I want to have happen here and how do I help the agent orchestrate it all, you know, kind of a thing. Um, yeah, but I, the other thing

[B]

I was going to mention, I don't know if I interrupted your train of thought there.

[C]

Go, go.

[B]

But, but the other thing that I would say is what practical things you could do. You obviously said, number one, grow your skill set. And when I think about grow your skill set, grow your expertise before you start going a different vertical, right? Like continue your expertise, whatever it is, use AI to make that faster sm, like more agile, then move to another one, another, you know, adjacent skill set. But the other, other side of the coin that I was going to mention is don't forget about the soft skill of that. If you're talking with leaders, manage their expectations because if they're reading this stuff, you got to be ahead of the game a little bit and be like, well, hey, actually this is what AI is capable of. This is what they're probably doing. Like, like bring them back to reality a little bit.

[C]

It's very much a managing up situation.

[B]

It's a managing up situation because if you don't do that. What ends up happening is all these people are all of a sudden going to be like, feel the pressure that now they have to perform in 100x when the tech is not even there yet. So like, you might be able to 10x but a hundredx like, okay, let's, let's everybody calm down. This is a little like hyperbole that's going on in the world right now and you're falling into it hook, line and sinker.

[C]

Yep. The big thing I'm communicating now is bottlenecks and constraints. And it's funny because the CFOs love this conversation. Love this conversation. But essentially I'm like, we can't use AI just to be productive.

[A]

We want to use AI to tackle the most. The most.

[C]

The biggest bottleneck holding us back, the

[A]

biggest constraint that if moved, makes the biggest difference.

[C]

Because these are the things that we.

[A]

There's all these activities we have to do every week, every month. We got to continue doing those and we can use AI to speed those up, but it doesn't matter how eff those normal activities become if we don't address the bottleneck. Which is why I'm like beating this

[C]

drum on this now on LinkedIn here on the podcast.

[A]

Because if you don't fix those things, then no, no amount of productivity is gonna help.

[C]

Like, there's a constraint and you can

[A]

only go as fast as that constraint.

[C]

It's like you can only run a race so fast if you're doing it three legged, you know, and you have a band ride around. The reason why I say it's because I run a 6k with a 3 legged before random fact about Dan Chaz today because I'm weird.

[A]

Uh, but that was a major constraint. You can only run so fast tied to another person. You know that if I wanted to go faster, I'd have to cut that by paintballs.

[B]

Who was shooting those paintballs? I won't say if it was me or not.

[C]

That was a different race, Ken. Different. Different paintball race. Yeah, no, I didn't get shot while I was three legged. That would have been too much. Um, yeah, sometimes now, now it's like we need story time with Dan and Ken.

[B]

Everybody's going to be like, what just happened?

[C]

But you have to find the constraints

[A]

of the company and then use AI, Help you find the problem. To find the problem, find it, define it, and then actually tackle the problem. And they're never easy. It always takes a long time to

[C]

actually usually fix the constraints. There's a Reason why the constraints, and

[A]

they haven't been fixed yet because they're

[C]

not easy and they take time. But the more of those you fix, the better things get.

[A]

Sometimes you need just a hundred little

[C]

constraints fixed in order to get a big movement.

[A]

Sometimes it's one big one that just

[C]

takes a freaking forever to finish.

[A]

But AI can help you with all those things, but probably not in complete automated mode. They just help you with bits and pieces of it. And you still have to drive the whole project manually with help and assistance

[C]

from AI, which is nice.

[A]

I find I rarely get stuck anymore because AI is able to get me

[C]

unstuck so much faster when I run

[A]

into techno problems or WordPress problems or CRM problems or why doesn't this work right now?

[C]

Problems.

[A]

And you can have it scan it

[C]

and bring you information and help you find the fix so much faster.

[A]

It's a amazing.

[C]

So it's getting me through the bottlenecks faster, but that's what people need to focus on.

[A]

And it's sad because I feel like

[C]

this a hundred x marketer, the way you become a hundred x marketer is not by orchestrating agents and systems, it's by fixing bottlenecks. Because if you fix enough of the bottlenecks, you could 100x them.

[A]

You could a hundredx the output, you know, and that's where you really should be focusing, not spinning up systems and

[C]

doing all the freaking content and stuff. I'm like, dude, that's.

[A]

If anything, I want to slow content down and focus. Like, what can I do that no one else can do? And then use AI to fix the

[C]

bottlenecks to get more lead flow going on, you know?

[B]

Yeah. And one thing that I would encourage, you know, something that you said that I don't want people to miss, is that as you're fixing the bottlenecks and using AI, it is becoming so much easier for you to lose being on the driver's seat and being coming out of the passenger seat that, like, people forget that you're supposed to be driving the whole situation. Dan. This happened to me, like this past week. We were texting each other back and forth about some podcast ideas, and I was like, throwing out these ideas. And you're like, this is not you. This is AI. Stop letting AI drive it.

[C]

And I'm like, I'm like, are you

[A]

leading this conversation or is chat. Because it sounds like chat's leading the conversation.

[C]

You need to take the reins.

[B]

And I'm like, oh, gosh, you're right. And then I was like, right I got a manhandle chatgpt and had to change the thing. But even myself, who's in it all day, every day, I think sooner or later we get decision fatigue, that we want someone to just give us advice and we pivot. And it's so subtle that we let AI do the work for us, that we have to be mindful of that as you're coming into it. So I think that's why when Finn said all those decisions that people need to make, I was like, he's spot on, because that's where people are going to get tired. It's not. Not that you might not have the expertise, but the 5,000 decisions that you have to make every single day for every little piece is going to be exhausting.

[C]

Dude, one thing that I've heard recently that's just given me so much freaking hope for the future, because sometimes I do get nervous. I literally will have, like, not panic attacks, but I'll have, like, moments of like, we're all going to lose our jobs. No one's going to have work, Economy's going to spiral out of control. I'm like, dude, I need to stop getting. I need to get on the newsfeed sometimes and go for a run. That's what I have to do to pump myself back up. Um, but something that gives me so much hope that kind of like, runs against that narrative in my head is the fact that almost everybody I know

[A]

who's, like, really into agents and harnesses

[C]

and is orchestrating that is freaking working way more hours, right?

[A]

And I'm like, it seems like AI is multiplying work.

[C]

It ain't doing the opposite.

[A]

So I'm like, ah, I don't.

[C]

I don't like working going away. We ain't going to undo the curse of work. Work will always have pain, and all humans are going to have to be involved, which is pretty much what historically has happened. Every time we've added new technology and automated grab, we've always just created more jobs and more work to do and more specialties and weird things. So I know this one's different because it's intelligence and who knows? And it's scaling across so many different ways in so many different sectors. So, like, I get it, I get why it's concerning, and I still understand that, but it just seems like right now the trajectory is that the smartest people using it are working way more. They've. They come. AI vampires, I think, or something like that.

[B]

Well, and. And part of it is, you know, we. We talked about this with ClickUp, but I. Everybody's creating harnesses and different tech stacks that now people are even creating their own tools because they don't want to use this tool. But, like, you're doing busy work and you're just adding stuff. And I'm like, well, just simplify life, man. Like, what's the thing that you need to change? What lever do you need to pull to, like, grow your business or grow your efforts or do the project, whatever you're doing. Focus on the accomplishment part. Not all the things that you're doing. This happened when I was trying to. I'm rebuilding one of my websites. I literally, you know, Claude started taking me on this bunny trail, and I'm like, whoa, whoa, what are we doing? This is not the goal. This is the goal. They're like, sorry, I just. It just started hallucinating and taking me down, down the wrong path. If I would not have caught that early on, I would have probably lost three hours in my day. And I think this is happening to a lot of people,

[C]

so I think that's good. Now I just need to go for a run and avoid getting shot by Ken in the woods.