AI in eCommerce marketing isn’t about “better prompts” anymore, it’s about better systems. Brett sits down with returning guest Russ Henneberry (TheClick.ai, co-author of Digital Marketing for Dummies) to unpack what’s new and what’s next: Claude Cowork, agentic workflows, skills that “self-improve,” and what happens when your AI can actually use your files, tools, and data — not just chat about it.

If you’re a DTC founder, CMO, or operator trying to scale performance without scaling headcount, this episode is a blueprint for how modern teams are building repeatable AI routines for content, reporting, and decision-making.

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Chapters:

(00:00) Intro

(02:05) What Cowork is: agentic plans, local files, and “skills”

(05:20) Skills that self-improve, plus persona + offer as core context

(08:10) Cowork as a “brain” with version control, shared across workflows

(10:10) Connected sources: Notion transcripts, Zoom notes, and MCP-style integrations

(15:10) Parallel agents and context windows: why this runs faster than chatbots

(18:05) Skill marketplaces, sharing zips, and the security caution

(23:10) OpenClaw/Open-source talk: the 4 “levels” (chatbot → cowork → code → open source)

(28:05) Hardware reality: Mac Minis, Apple silicon, and “processing power” as leverage

(31:05) Content system: Source → Structure → Format → Polish (newsletter example)

(38:30) Click.ai membership, team training, and closing thoughts on revenue/employee

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Connect With Brett: 

• LinkedIn: https://www.linkedin.com/in/thebrettcurry/ 
• YouTube: https://www.youtube.com/@omgcommerce 
• Website: https://www.omgcommerce.com/ 
• Request a Free Strategy Session: https://www.omgcommerce.com/contact 

Relevant Links:

• Russ’s LinkedIn: https://www.linkedin.com/in/russhenneberry
• theCLICK: https://theclick.ai/
• Digital Marketing for Dummies: https://www.amazon.com/Digital-Marketing-Dummies-Business-Personal/dp/1119235596

Transcript:

Russ Henneberry:

I think cowork will be the place where most business people will park it and say,

Brett Curry:

"Wow." Well, hello and welcome to another edition of the eCommerce Evolution Podcast. I'm your host, Brett Curry, CEO of OMG Commerce. And today I have a returning guest, a multi-time guest, maybe like fourth or fifth time. My good friend for a long time, fellow Missouri resident, Russ Hinnaberry. And for those who don't know, Russ, Russ led some teams at Digital Marketer, used to help run the Traffic and Conversion or TNC Summit back in its glory days, which that was just a rich, fun time- RIP. ... in this industry. RIP to TNC, it's so true. But you and I met in 2010 or something at a marketing conference in St. Louis, Missouri, The Lou,

Brett Curry:

And really connected then. But more recently, you are the founder of the Click.ai. You're also the co-author of Digital Marketing for Dummies. And when I have AI questions, when I want to know what are people doing with AI inside of agencies and inside of marketing orgs, I talked to Russ Henneberry. And so with that, Russ, welcome back to the show. And how's it going? Real good, man. How are you? Dude, I'm doing good. Doing good. Just feel like every day is going to unlock something new on the AI front and exciting, disorienting, scary, but mostly exciting. And so-

Russ Henneberry:

I mean, I didn't know how bored I was with marketing until we got like this. Yeah. Yeah. This technology has reinvigorated me for sure.

Brett Curry:

Yeah. And it's also one of those interesting things where obviously AI is progressing very rapidly. I heard someone say on a podcast just yesterday, they were like, "No, 2026 is going to be the year of the most rapid disruption ever on AI." And I'm like, okay. Yeah. And then there'll be more disruption this year than all the AI years past or whatever. So buckle up, which is fun for sure. So I want to dive into a few things. I want to talk into agentic AI and kind of how things are flowing and then just some of the latest news. But also you're plugged into agencies, marketing orgs, brands, and you're seeing how they're using AI and what you're doing with AI. But I think maybe the first place to start, because I know this is something you were just absolutely bullish on as MI, and that's Claude cowork.

Brett Curry:

And so it's just absolutely ripping right now. All my business friends are using it. I just started testing it actually just this past Saturday, started tinkering with it and holy cow. So for those that don't know, what is Claude Cowork? And then let's dive into some applications.

Russ Henneberry:

Well, so there's a few things about Cloud Cowork. We've probably all used regular ChatGPT, regular Cloud, regular Gemini or whatever. The new thing about Cloud Cowork, so it's a desktop app right now only available on Mac. And the big three differences I think to think about with Cowork is first that it is far more agentic. So it makes plans and unfolds those plans right in front of your eyes. So you can ask it far more ambitious for far more ambitious tasks than you could with a regular chatbot. And the reason it's able to pull this off from watching it work is that it works with your local files. So it can create files, it can delete files, it can move files around. And one of the most important types of files that it produces is called a skill.md file or a skill file. And that skill file, you can think of it like you would think of a custom GPT or a Gemini Gem, but it's just a set of instructions as to how you want something executed.

Russ Henneberry:

And here's the crazy part about this is that when you're working inside a cloud cowork and you do something, or you can even describe something that you want done, it can build that skill file and then just save it into your directory. So it starts to organize this entire set of folders and files. And one quick tip on this is that when you do go to start to play with this, go slow and just kind of think through how you want that folder set up, that structure set up. Because if you've worked with something like ChatGPT before and you create a custom GPT that does X, like let's say it writes hooks for ads or something. So it's a custom GPT that's really good at writing ad hooks. Maybe it's personalized for your business and your persona and all these things. So it's an excellent GPT.

Russ Henneberry:

But the problem is with it is that it's saved in the cloud and if it's not performing properly, you have to go back over there, edit it, and you got to go in there, figure out where it's messing up and change it. Well, you don't do that in Claude cowork. So if it produces an output and you say, "You know what, you're being way too hypey with those hooks. Those hooks are way too hype. I like this one because it's a little more down to earth and that's a little more on brand." It'll go back and edit the skill. So it'll ask you for it. Say, "You want me to go and adjust the skill so that I just nail this for you every time?" And so these skills are almost like self-healing, right? They build themselves pretty much. They ask you, "Do you want me to build a

Brett Curry:

Skill?" So self-improvement or recursing at most.

Russ Henneberry:

Yeah. Right. And it all is happening on your local machine. In other words, there's a version control part of this as well. So one of the things I've always recommended with AI is that the very first piece of information that you need to feed any AI when you're doing anything about marketing or business growth is a persona document. You need to know who you're talking to.

Russ Henneberry:

So it always boggles my mind when people are like, "Oh, my AI doesn't give me very good output." And it's like, well, does it know anything about who you're trying to reach or who you're talking to, who you're writing to, who you're planning for? The second document that I always recommend is a document that clearly outlines your offer. So what do you sell? What's the cost? Do you have a guarantee? What are the deliverables, et cetera. Those two pieces of information, and most of us have kind of caught onto that, that we could feed the AI this and we feed it that and it gets much, much better. The problem has been that there's a version control problem. So you build a GPT and you attach these persona and offer over here, and then you build another GPT, you got to attach the second one and the third one.

Russ Henneberry:

But in Claude Cowork, since you're working from a file system and it's basically just plugging a brain onto Claude cowork, there's a single persona.md file, a markdown file, or it could be any, I guess it would be a text file if you wanted it to be, but Claude Bill's markdown files that you can adjust that one place. And anytime it needs that persona or it needs that offer or it needs this skill or it needs this spreadsheet or it needs whatever, it just goes and finds it. It's very, very, very good at understanding when it needs a particular piece of context that's located somewhere in your brain.

Brett Curry:

It's amazing. Amazing. I think it's still a little bit trippy for people and they're still maybe not fully wrapping their heads around it. But I mean, Claudco work can really become your personal assistant in a lot of ways, your research assistant, your marketing assistant, your copywriter, all those things. But more than just a chatbot, it's just like doing things, right? It's just running things. And so maybe you could talk through some specific examples, like either where, how have you used Claude Cowork? I'll explain what I was experimenting with this weekend as well, but how have you used it? What are some of the best use cases you've seen from agencies and brands? What can this do for us?

Russ Henneberry:

Right. So one of the other things about Claude is that, and I think this is the Cloud ecosystem in general, is how good they've gotten at connecting to external sources. So for example, I've connected my notion to it, and so Claude Cohort can just go fetch something out of ... So for example, when I start a Zoom meeting now, my Notion starts to transcribe those notes using Notions AI, which is cool. But at the same time, do I do anything with that? Do I do much with it? And so my workflow now though that I've got Cloud connected to Notion is, I jump on a Zoomie. I did a webinar today, a training today with some people and 90 minutes on ChatGPT projects and I was going through that and then Notion's transcribing, and then at the end I can run a skill through my Claude cohort that just says, "Go grab that transcript and do X to it.

Russ Henneberry:

" So I think that's really the unlock here, is to understand that we have to have sources of material. Where is the source of some idea, some data, some source, and how can we plug that in and then what do we want to happen? And if we know those two things, what do we have to put into the AI and then what do we want to happen from there? Even if we can just describe it, the AI will figure it out from there and then it'll ask you, "Do you want me to just build a skill that just does this every time?" So you talked about, before we jumped on, like doing things with your financials and stuff like that. So dropping some source material into your claude brain, if you will, spreadsheets, et cetera, and then pointing Claude cowork at it and saying like, "I want you to transform this into whatever." It could be charge graphs, insights, whatever.

Russ Henneberry:

And then at the end saying, "Write that up as a skill or even a full routine." So I mentioned about trying to get a little more ambitious with what we're asking

Brett Curry:

You. What's the reason why a skill and a routine? Can you talk about that real quickly?

Russ Henneberry:

Well, a skill would be the technical term for it inside of Claude, but I do think about these things as routines. So for example, when I arrive at my desktop, I just open Claude co-work and I say good morning. And that triggers a routine, but it's really a skill. So it's written into a skill file, but I think of it as a routine because what it does is it greets me, it puts my manifesto out, which is like this thing that I like to read each day. And so it's got steps and then the next step pulls my weather because I'm always wanting to know what the weather is when I'm sitting inside at my desk all day.

Brett Curry:

Isn't that funny, but Will, but we both live in Missouri, right? So typical Midwest, it's like it's going to be 70 degrees a few days from now. It was like negative five a couple weeks ago. It's just crazy. But like it matters. We're sitting in the AC or the heat, so we're fine, but we still want to know. But yeah, you want to kind of run this skill or this routine, right? So yeah, what else does it do for you in the morning?

Russ Henneberry:

It goes and grabs everything out of my calendar and displays that for me. And then it pulls top, I don't know, five headlines off of several sources about things that I'm interested in and pulls them in and gets my news and stuff. But not that this is tremendously groundbreaking. What it is is it's a routine. It's something that I told, do this, then this, then this, then this and this, right? And it just writes it into a skill file, sits it into my clog brain there. And then anytime I say good morning. So the same deal with my newsletter. So I write a newsletter each week. It's quite involved. It has several parts to it. And I used to have to have like 15 GPTs going and like different deep research prompts that I had to keep copying and paste. Instead now, once I ran through the process one time, the way I wanted it, I just said, "Create skills for that.

Russ Henneberry:

Create skills that format this into this, create skills that do this deep research." And so now it's just more or less like, "Hey, I'm building the newsletter." It's like, cool, where do you want to start? And it's like, let's start with this. And it goes out and does the research. And the thing is you can spin up multiple tasks at the same time. So it's like it goes off, does the deep research, open a new task, start something else up. And the way Claude is built, the way Cloud cowork is built is that it can work in parallel. So it does things a heck of a lot faster than you would think it would be able to do something because it'll spin up four, five, six agents at the same time. Each one, this might get a little technical, but each one has its own context window.

Russ Henneberry:

So in other words, this one's out there doing this. It's literally like running five clouds at the same time. Right,

Brett Curry:

Which this is actually important. So let's talk about Context Window a little bit, because I first heard about this on the Andrew Ferris podcast recently, but what I think a lot of people don't know is if you give Claude a really big file or maybe like a transcript from a really long call, it's not necessarily crawling all of that, right? It's maybe looking at the end and the beginning and maybe summarizing some things. And if you give Claude a whole bunch of stuff like all in one prompt or something, it's going to take shortcuts potentially instead,

Brett Curry:

But having multiple agents, you can have a lot more context that you're feeding the AI. Hey, thanks again for tuning in. This episode's brought to you by OMG Commerce. That's my agency. Hey, we're specialists at creating omnichannel growth for brands profitably. Now, the greatest brands we know are no longer just D2C. Yes, they're masters of D2C, but they're also growing and scaling on marketplaces and in retail stores. And we understand the complexities of how to grow in all of those channels from a campaign strategy, a creative strategy, and a measurement strategy. In fact, we recently won a Google Agency Excellence Award for helping Arctic coolers grow their retail sales in Walmart using YouTube. We've helped add almost eight figures in growth on Amazon for brands, and we've even helped a brand go from nine to 10 figures. And so we want to help you grow.

Brett Curry:

So if you're not satisfied with your growth in any of those channels or you're looking to unlock new growth, we should probably chat. Visit us at omgcommerce.com. Click that Let's Talk button. We love to schedule a strategy session with you. With that, back to the show.

Russ Henneberry:

Yeah. And the thing is, right now we have Opus 4.6. We've got Gemini three or whatever. We've got ... These models are all very, very intelligent, but CloudCowork really isn't a breakthrough in intelligence as much as a breakthrough in sort of architecture of how the tool works. It's not that the tool is that much smarter, although it's a little bit smarter. These tools get incrementally smarter every couple of months. They release something that's smarter, but it's the UI that's different, right? And it's sort of the what's under the hood that's different about Claude Cowork. And it does take a little bit of getting the hang of how it works, but once you get going, it's actually super good at kind of walking you through like, "Do you want me to do this? Do you want me to do that? " And so if you're going to play around with CloudCowork, I would just say start with a simple use case and just start to type and watch it start to build something out for you.

Russ Henneberry:

It's pretty amazing. The other thing that's really interesting about these skills is that they're extremely shareable. So for example, I've built out an entire workflow around building my newsletter and in my membership, I'm just going to give it to my people. So it's like, here's a zip file. It's got all the skills in it and all the context in it that it needs. And so just upload it, zip it, upload it, and now you have that skill. So

Russ Henneberry:

Pretty cool too, and there's little marketplaces springing up that are thousands of skills, like anything you could think of that are already there, you just download the zip, Zip uploaded inside of Claude as a new skill. And I think I'd be a little

Brett Curry:

Careful about that. It'd be good to go with the song there. Yeah. Be a

Russ Henneberry:

Little careful about downloading other people's skills because people do stupid stuff with the instructions and stuff like that. But it's a different way of working with AI that I think OpenAI sort of dropped the ball with not updating how custom GPTs work all this time. And now skills have come along and cloud coworks come along and the two together, it's a combination that's hard to

Brett Curry:

Beat. It's a winning combo. Yeah. So a couple of things I want to unpack and I'll kind of talk through a little bit of what I did this weekend and where I think this is going to unlock some pretty cool stuff for my agency. You talked about connections. And so basically what I wanted to do, we got this very detailed financial dashboard that's got everything in there, client revenue, cost of employees, cost of various costs of different service items. We kind of group our expenses into delivery or all the team, all the tools that deliver services into growth. So sales and marketing expenses and tools and payroll and then ops, right? So all the tools and overhead and employees and stuff that fit there. But I wanted to analyze some things. And so this is kind of hard, like what do we dump into what spreadsheet or whatever?

Brett Curry:

And so basically I gave Claude, I was like, "Hey, this is a framework that I want to work within. Here's some of our goals. Net revenue retention is a number we're going to start tracking regularly." We did this in the past, but the calculations are actually kind of difficult and building that on a spreadsheet is also kind of a pain of the butt. But basically that's where you're looking at starting revenue for a beginning period of time. And so we just take the beginning of the year, what's our starting revenue? Over time then minus any churn, so logo churn or clients a churn minus contraction. So maybe a client didn't churn, but they reduced scope, so now they're spending less. So it's beginning revenue minus those two things plus expansion, meaning, yeah, but some clients actually add the scope and actually do more work with us.

Brett Curry:

And so then what is that that's net revenue retention? Basically I started like, "Hey, Claude, this is what I want to do. " Cloud cowork. It's like, "Oh, cool. Well, do you want me to connect with QuickBooks so I can connect directly to QuickBooks?" I'm like, "Well, why don't you just look at this Google Sheet first?" And then it's like, "Oh, this is a gold mine of information." And so then it starts spinning stuff out. And then I started talking about some of the sales goals and stuff and looked at our sales pipeline and the sales goal sheet that I put together and I started to say, "Hey, this is good. Here's where you maybe have some weaknesses." And so spit out these different analyses and I'm like, "Holy crap, this is awesome." And so right now I've just got to looking at our Google Sheets because you can do the browser plugin where it looks at the Google sheets and can read it, or you can upload a Min Excel file or you can plug it into QuickBooks.

Brett Curry:

So there's different ways you can run this. And so yeah, it's going to be a real unlock for financial insights because we don't have a huge finance team. And so it's going to be very, very powerful. Yeah.

Russ Henneberry:

Yeah. I mean, I think it's a good bet that every day that goes by, the people doing work at computers are going to spend a little bit less time outside of an AI tool than the day before. So as AI tools like Claude Cowork keep developing connections to other outside tools and they've already got that protocol in place called MCP and everybody's pretty much on board with it and starting to connect everything together, it'll just become sort of a push and pull type of a situation where I'm able to just pull this from here. And the nice thing is that you got this sort of central terminal with intelligence inside of it, and you can pull from disparate sources and pull things together and either create new things or get new analysis out of those connected things. And what it does is it's opening up things that you never would have had time to do without these tools.

Russ Henneberry:

So a small company now can do things that large companies have been able to do for a long time because they have a whole team of financial, you know what I'm saying?

Brett Curry:

Yeah. Yeah. You have a whole finance department

Russ Henneberry:

To go pull this out. A department there that's running all this analysis and doing all this stuff, but because they got to pull from all this stuff and it takes like human effort to get through all that. But what I would encourage you to do, and you probably did do, is as you're working through something manually, you can always pause and stop and say, "Okay, I got this kind of how I wanted it sort of manually, but even using the AI, so it's not completely manual, but you understand you're just kind of prompting through and you get to this sort of end state and you're like, that's what I wanted." That's when it's a good time to pause and reverse engineer into a skill or even if you're using ChatGPT, you reverse into a custom GPT, say, "I want you to take a look at everything we did here in the end output and I want you to codify this and create the instructions to get here like that.

Russ Henneberry:

" And the nice thing about cowork is it knows if you said something like, "I want to run the financial analysis again," or give it some other kind of name, it'll know to go grab that skill-

Brett Curry:

Shows what to do.

Russ Henneberry:

... and then it has a lot more autonomy. It'll go and run several steps up ahead and it might hit a point where it's like, I need some input back from Brett, and so it's going to come back and say, "Do you want me to do this this way?" And you just select that and sometimes it'll write that into the skill so it doesn't need to ask again. And so it's really quite intuitive in that way. And it's just a massive step change from what we're used to with regular just chatbots.

Brett Curry:

Totally. And then I want to get your take on OpenClaw in a second as well, and then a few other things. But you also said something that because tools like Cowork and there'll be others, I'm sure, they'll connect to almost anything. And over time, they're going to connect to basically every piece of SaaS you use, every other piece of tool, whatever. There is a realistic future where most of the interaction we have on our desktops or on our phones is with an AI and it's the one connecting to all the tools and pulling things together, doing what we want it to do. And so yeah, just really, really fascinating. What's your take on OpenClaude for those that have been following the news? There's a tool that's had what, like three or five names in the last week. It was Claude, C-L-A-W-D, bot. Then Claude, who we've been talking about was like, "Don't do that.

Brett Curry:

That sounds just like our name." And then it was Molt bot and then now I think they landed on OpenClaw. Who knows by someone else to this maybe something different, but what's your take on that? Because that has been wild. It's been such a big deal. Even my 23-year-old son who's in the roofing business in sales, he bought an Apple Mac Pro or whatever, a Mac Pro and he's running it on a local machine and it's doing some business development stuff for him. But what's your take on OpenClaw? Where is this taking us?

Russ Henneberry:

Well, for the people listening to this, I would probably be listening to this, right? I mean, the person who's hardcore and you want pure control and you want all that stuff, you're probably not listening to this show. But if you're a normal business person, you're running a company or you're in marketing or whatever, I think that there are essentially sort of four steps here that we can think about. So you've got your sort of chatbot. So regular ChatGPT 5.2 or whatever, regular Claude still available, that's level one, right? Level two would be to kick up the cowork. And I think by the end of this year, everybody will be in the working knowledge workspace, working on a computer, you'll be working in something like cowork. It may not be cloud cowork, but it'd be something like it. Yeah. Google's version of it or OpenAIs, version or whatever.

Russ Henneberry:

Then the third level would be something like ClaudeCode or over at OpenAI, it's called Codex, where you're going straight to the tap, you're kicking past any sort of UI user interface and you're just going straight to the source. And you're already starting to get into pretty hardcore when you're doing that because you're working in terminal and you're having to use some coding languages and stuff like that, but it's doable. If you really committed to it-

Brett Curry:

It's vibe coding, right? So I mean, you don't have to have a ton of programming knowledge, but maybe some, or you're understanding prompts in a different way. Could the average person just jump into Claude code or something similar or that's going to take a little bit of

Russ Henneberry:

Work? Yeah, I think you could. It would be a longer learning curve than Claude Cowork. Because what Cloud cowork is, is it's Claude code with a UI sitting on top of it. Yeah, I got it. And what happens when you do that is it puts some restrictions on you. You're not going straight to the source where it's just like you can do anything in here because you've got the restrictions of that sort of harness that's sitting over the top of Claude cohort. So going straight to Claude code is like level three. And then you get into the open source stuff where your son wants to buy an extra computer because he doesn't want that open source sort of no guardrails AI to be on his own machine, you want to create a

Brett Curry:

Combined space. We're pointing into his email. He's creating a separate email and a separate browser and a separate machine, but- Yeah, people are

Russ Henneberry:

Daisy chaining 10, 200 Macs together and creating armies of employees that don't exist with Slack accounts and email accounts and all these things. I would say the average person, level four is, forget about it. It's so powerful and it really is. It's not that it's not powerful, but it's precisely because it's so powerful that you shouldn't rush to install it. Just pump the brakes a minute because what's going to happen is some more secure company is going to release something. And Claude Code is already just insanely powerful if you just go straight to Claude code and you still have a lot of guardrails there. The thing that I would

Brett Curry:

Point out though- There's all kinds of unlocks, all kinds of stuff you can do, a whole world open up to you in those levels one through three that you don't need, or one through four, you don't need to go open claw just yet.

Russ Henneberry:

And I think cowork will be The place where most business people will park it and say, "Wow, this is quite a

Brett Curry:

Lot of power." And just so you know, we're not sponsored by Claude. We get no kickback from co-work. We're just like, this is awesome. We're geeking out about it using it. And so it's phenomenal. Yeah.

Russ Henneberry:

The one thing I wanted to point out though, the other comment about OpenClaw that it raised is that, so in the summer I started to realize I was doing so much hefty work with AI tools and running Zoom and other things that my laptop was a beast, but it wasn't able to keep up. And I do think that we as business people need to be thinking about our own tech the way that a lab thinks about how many GPUs they have. Starting to think about what is the processing power of your company, of any individual in your company. So I went ahead and bought a pretty hefty Mac Mini because I was like, "I don't want to be constricted by my computer." So that's kind of interesting that you start to think about your own ... I mean, you always think about you don't want your computer to be slowing you down, but at this point, it's sort of like you're going to see Apple just pick up a giant windfall from like- Yeah.

Russ Henneberry:

Well,

Brett Curry:

Their stock is already up just because so many people are buying Mac Minis.

Russ Henneberry:

Yeah. All the hardware that's needed. That Apple silicon is what everybody's after. Yeah, it's wild to think about somebody like your son who's young and starting out in a business, having essentially desks with nobody sitting at them, but there's people working.

Brett Curry:

And he just ended up, he's in roofing sales and so he's like, "Dad, I'm going to reach out to all these insurance agents and I want to get them an email here and then I'm going to drop by their office and get them donuts. I'm going to do these things. And then I want this to be able to respond via email over here and pull together my calendar and I've got these Notion apps." I'm like, "Love it. " I'm like, "This is awesome. This is great." And also I'm glad you're doing it on that machine because I'm not ready for Open Claw, not for OMG. Heck no. But I want to see it. And yeah, I'm all in on coworking and figuring that out. And so one quick thing though, using AI, still the ROI can be amazing and it's low cost compared to what it should be based on the power of the tool.

Brett Curry:

But we start using CoWork or OpenCall or whatever, you can start to, you're spending more on these tools. This is not necessarily the $20 a month subscription, right? What are you seeing since you're leaning hard into cowork? What has that done to your monthly fees and your usage and what kind of plans do you have to be on to make this work?

Russ Henneberry:

Well, I use the $100 a month max plan, but the fact they do have cowork now available at that $20 a month, you probably will find that heavy users of it. They're going to need that $100 a month plan. But I think if it's being used right, it's just a no-brainer for 100 bucks a month.

Brett Curry:

A month for an assistant. Okay. Yeah, plus.

Russ Henneberry:

Yeah. I think that with the proper setup and structure ... See, I've always said that these AI tools are extremely useful, but even going back to my last time on this show where I was talking so much about context,

Russ Henneberry:

And I mentioned that a little bit today about how if you're not giving it any context about your offer, your persona, don't be surprised if you're just not getting anything out of it. And that sort of blows up when you start to think about how something like Cowork can access really any context when it thinks it needs it and it can find it. It can find it in your machine. So when you go back to your example around the finances, when you talked about your sales goals and all these different documents, I know how organized you guys are at OMG. It's impressive. And you guys document a lot of things and you have goals and you have rocks and you have quarterly and yearly plans and all that stuff. And that kind of stuff all can be brought into your Claude cowork space. And the way to do this, honestly, is when you're playing with it, is to ask.

Russ Henneberry:

Take something like a quarterly plan or something, drop it in and say, "Here's the quarterly plan, where do you think this should be most properly structured inside

Speaker 3:

Of

Russ Henneberry:

Claude?" And before you go and decide where it goes and where to put it, ask it to think it through. So to go analyze that file and start to connect it, well, and I see this skill over here where you run a financial analysis, I see this skill here, and maybe the best thing would be to organize it this way and it'll ask you, "Does that sound good?"

Speaker 3:

Yeah.

Russ Henneberry:

And it starts to build out ... There's a file at the very central core of Claude called the Claude MD file, claude.mdfile, which is basically, you could put anything in there, but what you do is you just tell Claude, keep updating that Claude MD file because what it's doing is it's telling Claude, how does this structure work? It's sort of like a central plan as to how Claude is supposed to interact with your ... So anytime you use Claude and it can, it will access that claud.md file. So that's the thing is that the more you give it, and there's definitely an unreasonable amount of stuff you could give it, but things like that, it's like, "Well, that's really something that I consult my own brain when I work on my finances." You might consider, should I drop this into the Claude Cowork space so that it has access to that?

Russ Henneberry:

And you should be shocked at like, wow, it realized it needed to go look at that and then go grab the skill and then connect over here to HubSpot and then ... You know what I mean? Right, right.

Brett Curry:

And

Russ Henneberry:

That's what I mean when I say agentic, right? So agentic.

Brett Curry:

It's amazing. Let's do this. I know you talked about a couple workflows that you built for content creation, and I think this maybe is around your newsletter, but do you want to actually share that? We had to talk through it for those people that are just listening and not watching, but would that be worthwhile to kind of dig into? Yeah. I'm curious while you're doing that, are you using Gemini at all? And are you leaning into Gemini gems or Gemini as a

Russ Henneberry:

Tool? Yeah. Yeah. So I use Gemini almost purely for image generation. Oh,

Brett Curry:

Nice.

Russ Henneberry:

Yeah,

Brett Curry:

A banana.

Russ Henneberry:

That nano banana model is still- It's pretty insane. ... the thing. But yeah, let me run through this workflow. Maybe it'd be helpful to a lot of people to see how ... Is that going full screen for you? Yeah,

Brett Curry:

Totally see it. Yep. So it's full screen. So for those watching on YouTube, they'll see it. For those listening, we'll do our best to describe it and make it come to life in your mind's eye.

Speaker 3:

Yeah.

Brett Curry:

Well,

Russ Henneberry:

So this is really about creating any content or copy of any kind. It could be text, images, video, audio. Any kind of content is ... I started to realize, as you know, if I had to be pegged to any one digital marketing discipline, it would probably be content marketing. And it's the biggest reason why I hopped on AI so fast because I saw it creating content and I was like, wow, this thing can actually create things. So as the years have gone by, I mean using this, I'm getting better and better and better at creating content and copy with AI tools. And I started to realize there's this underlying process that constantly gets used over and over and over again, and it's really this source, structure, format, polished, sort of steps. And the way it works is that the first step is the source. So if I'm going to create a piece of copy, like a sales page, an email, an ad, or a content like a video or anything, it doesn't matter.

Russ Henneberry:

There's got to be some source. And most people that are failing with content creation, copy creation with AI, they start with the AI and they start to say, "Well, come up with the idea and then write the idea or come up with the idea." And so it's like, well, where are you in this scenario? Where is your voice? Where is your brand? Where are you? And so when we think about setting up any sort of workflow to create something, the first step is to figure out, well, where am I going to get this source material from? And that source material can either come from you, in other words, your brain or you're from internally in your organization, or it could come from outside. It's the same as before, before AI.

Speaker 3:

Yep.

Russ Henneberry:

So from a standpoint of you, you might rant into your phone or something, some idea that you have, or you might, maybe you do podcast interviews like this one, right? Or maybe you shoot videos or maybe you do webinars or you write or something. There needs to be ... So if it's going to come from you, at some point, some ideas got to come out of your brain and essentially your mouth. If it's going to come from elsewhere, that's great too. You can go and grab source material from all over the ... I've said many times that the web doesn't necessarily need more content. There is a great service to be done in curation of content, right? Like this is good. I read 10 articles. Here's the one you should read. And so you can go and curate from elsewhere, but you've got to have something that the AI is starting with.

Russ Henneberry:

Now, step two is to structure that in some way. So the fact is, if you go and rant into your phone an idea, that's a great way to create a source, but it's not in any structure that you can do

Brett Curry:

Something- Not usable, not valuable, not shareable really. It's just brain

Russ Henneberry:

Dog. Yeah. So typically a workflow might look like ... First I get this raw input, let's say it's a rant into the phone, and then I take that and I put some kind of structure around it. The two best ones, in my opinion, are a set of bullets or into a table. And so you just tell the AI, "Hey, take this input, whether it's a rant, a transcript, somebody else's YouTube video, somebody else's article, it doesn't matter if it came from you, but it's got to have a source and then take that and organize it in this structure." And that's a second pass with an AI. So the first pass is ingest this or go get this source. The second pass with the AI is, now organize it in some structured format. Then the third is to literally format thing into whatever structure you want, that piece of content, whatever's going to come out the other side.

Russ Henneberry:

So if I have a rant into a phone that's just me rambling and rambling, rambling as I'm driving up to the gym or something and I save that and then I drop it into the A. The first pass is to ingest it and then take it and organize it into a table or into a set of bullets. And then the third pass might be, "And here's how to take that and organize it into a LinkedIn post for me. " That's a third pass with an AI. So it's not one pass.

Russ Henneberry:

It needs separate instructions at each step along the way. And then that last step is to polish. So bring it up to publish quality, and that could be a combination of you and the AI, or it could be just you, or it could be just AI for those of us that are wanting to automate our lives completely away and just are publishing things to LinkedIn and elsewhere that ... But I have found that this structure reoccurs no matter what I'm building, is that I need to figure out where's the content coming from, where's the idea? How do I organize it in a way that's useful? How do I then transform it into whatever ... Do I want a script to come out of that? Well, that's fine. Do I want a written post? Do I want a cartoon? Do I want a slide for a presentation or a set of slides?

Russ Henneberry:

Anything is possible. I take the source, I give it some structure to organize it so I can look at it. Oftentimes there's some curation that happens here, by the way. You get it into a table and you're like, just take ideas three, 10, and 12, and then move it on to step three, which is, how do I take this? I mean, you almost think about this just a set of rules that you keep moving things through. And then that last step could be add a brand voice to it using AI or do like we have always done. Type. Actually

Brett Curry:

Edit the thing. Wait a minute. We're in there typing and editing. What's up with that? What is this? So what does this look like then? Is this maybe a four step process just inside of our favorite chat interface? Are we pulling something together that's a little more agentic? What are you recommending here?

Russ Henneberry:

Well, and that's going to depend on the tool and the actual process, but take a look at this. This is just how I put my newsletter together here. So the step one is deep research. That's a great place to go get a whole bunch of source material. So you tell an AI, "Hey, I want you to go out there." This is for a newsletter, this example. So I want you to go out there and find the 10 best stories about X. They're most popular. I want you to check Twitter. I want you to check here and it comes back and I want you to structure that

Brett Curry:

As- Do you have a favorite tool there? So for deep research, I know they're all getting better. They're all good, but what are you using there, John?

Russ Henneberry:

I use ChatGPT for that, but now with cowork, it doesn't ever call it deep research. It just goes into research mode. You know how in the past it's been like, I am now entering deep research. You know what I mean?

Brett Curry:

When you select it, I want you to do deep research. Go. Yeah.

Russ Henneberry:

Yeah. No, I mean, they sort of evaporated that because it's just over there doing things and it'll just enter into more of a deep research mode where it might be gone for 10 minutes. Like I said, I spin up another task and work on something else. But in this case, I use deep research. You can use any tool pretty much has deep research now. You create a prompt and you could create a prompt and save that prompt if something you use over and over again, have it come back. And my big thing about deep research is that it usually brings you back this report that's like, "Okay, I guess there's my afternoon to read this freaking report."

Brett Curry:

Take four hours to read that.

Russ Henneberry:

So what I'll do is I'll tell the AI, "Don't bring me back this big long report, structure it into a table." I love tables, right? I love organizing- Scannable. ... especially things that come

Brett Curry:

Back. Easy to digest. Yeah.

Russ Henneberry:

Yeah. So imagine in this scenario that I have 10 stories from various news outlets, not my ideas, this is other people's ideas that I went and had the AI go and grab together. And then this next step represents a set of rules as to how this particular story needs to be transformed. So I just pull up, I use Beehive for my newsletter and you can see this is a story that I ran last week, put this Jerry Seinfeld gift, OpenAI is putting ads in ChatGPT because GPUs don't pay for themselves. And there's a structure to how this story works. It's the facts and then why I think this matters to my audience. And so all I do is create another pass of the AI that says, "Go in here, grab whichever story that Russ wants." So Russ curated story three, let's say, and apply this set of rules to it.

Russ Henneberry:

And that set of rules then spits out on the other side a formatted piece of content. And then that last step is to polish it, edit it, get it right, check the links, fact check the story in this case, right? It's always different, but the same deep research is used to create another block of my newsletter called, it's actually called By the Numbers, but I used to call it Stat of the Week. And all I do is I take a story in here, let's say Story five in the list has a good stat in and I'm like, "That's good to share." And I say, "Okay, run Stat of the Week rules on Story five and it outputs a different output." Does that make sense?

Brett Curry:

Totally, totally. Yeah. And then it ultimately ends. We're telling it then, take these ideas, run this process. It's the source structure. What was the third one? Format. And

Russ Henneberry:

Polish it.

Russ Henneberry:

And then the third idea here is the tool of the week. So if I find something that's like, okay, that's a bad, nice tool there, I've played with it, I want to bring it up. So I've got a structure on that. So it's the same set of research, three different outputs. And the difference is that this set of rules is different for each of those structures. And if you think about this from a standpoint of building any content or copy, what is the story? It doesn't have to be deep research. Of course, it could be a rant, it could be a transcript, it could be a YouTube video, it could be any place that we generate ideas, then take that, get it into some format. And again, I almost always recommend bullets or tables because from there, once you get that stuff into a table, you can then say, "Okay, apply these rules and apply these rules." Now, if I take this one step further and go into cowork and how cowork works, how cowork works, the way ChatGPT, let's first start with how ChatGPT still works, would be if I want to format it this way and this way and this way, I would need three different GPTs, I would have to stop and I would have to call that GPT or copy and paste a prompt.

Russ Henneberry:

Instead, what I do is I say, take story one, turn it into a news story format, take story four, turn it inot of the week, take story six and turn it into tool a week, and it's got all those skills saved in there and it just goes and runs and it's just like ... And if I get to the end and I'm like, "I really don't like how you're writing those headlines for the news story, I want you to change it so that it works this way." And then it'll just say, "Cool, I changed that and do you want me to update the skill?" And it's like, yeah, so that next time I run it, it's done. So it's sort of that self-healing idea that we talked about

Brett Curry:

Earlier.

Brett Curry:

I love it. I love it. This is fantastic. I could spend another hour going through this stuff. Actually, I would like to because I've got like a million questions for you now. I guess we are running out of time. So I guess the next thing is I got to have you back for the 10th time or whatever it is. So we'll for sure do that. But where can people find more? So you've got a community called the Click.ai. Talk to us a little bit about that. And then also your great follow on LinkedIn and other places. So talk about that as well.

Russ Henneberry:

Yeah. You can always find me on LinkedIn and even message me over there. I'm almost on LinkedIn all day long. The Click.ai has two components to it. It has a membership for individuals. And then I do team training and implementation for teams. So both of those things you can find on the Click.ai, the membership is really about using AI to do business work. These tools, they're general purpose technologies. They're like electricity or something. We have the electricities everywhere and it's used for dang near everything. So AI is the same, right? It wasn't built for business and it wasn't built for science and it wasn't built for education. It was built for all those things. And there's no instruction manuals out there for each one of these massive things that we can do. And this is a big time tech transformation. And so the membership is there for people that are trying to figure out, how do I use these tools to do real business work?

Russ Henneberry:

And I do think that we are entering in, you mentioned that the 2026 is going to be a big year. I do think this Cloud cowork jump is a big one. And we are going to start seeing a gap between both individuals and companies that adopt this stuff and start to get more out of the same team.

Brett Curry:

Totally, totally.

Russ Henneberry:

It's just crazy.

Brett Curry:

And that's what I've heard recently. It's like, we shouldn't be fearful that AI is coming for our jobs. Most people, there are going to be some exceptions, so don't want to downplay that. But hearing people talk on podcasts, the team members you have, the team members that really understand AI, and maybe they can both vibe code and use cloud coworker or whatever, they become worth two or three or four employees to you. And so that improves someone's marketability and someone's earning potential. It doesn't diminish it. And so yes, the gap is going to be widening between those that embrace this and Excel at it and the companies that embrace it and Excel and those that don't, the gap is going to widen for sure.

Russ Henneberry:

Yeah. An interesting number right now to look at is revenue per employee, right?

Brett Curry:

Yeah. I love that number.

Russ Henneberry:

How big can your ... You mentioned I was with digital marketer and I was texting with Richard Linder the other day, and we were talking about how many people would have taken for us to get DM to wherever we got it was like 25 million or something. And by the time we did that, we had like 80 people and we're sitting there thinking, man, we could have done that with four or five people maybe with these

Brett Curry:

Tools. It's crazy what's possible now. Crazy.

Speaker 3:

Yeah.

Brett Curry:

Yeah, for sure. It's awesome, man. Really appreciate it. I do want to even jam with you one on one because I've got some stuff we got to talk about, maybe get you in for some training. And so for those listening, do that as well. Check out the click.ai, hire Russ, put these tools to work for your business. With that, Russ, thanks, man. Ton of fun. Looking forward to the next time. Good to see you, buddy. Absolutely. And as always, thank you for tuning in. We'd love to hear from you, leave us a review on iTunes or wherever if you haven't done it. Also, if you found this episode helpful, share with somebody else you think will benefit from it. And with that, until next time, thank you for listening. Hey, as we wrap up this week's episode, I want to mention, if you're a great brand, if you're scaling high seven, eight, nine figures in D2C or Omnichannel, we should potentially talk.

Brett Curry:

We've worked with some of your favorite brands and we'd love to consider working with you as well. We are masters at unlocking new channels like YouTube, unlocking new scale on platforms like Amazon where we can add up to eight figures in new growth, and we've got multiple ways we can work with you. So we can do the full service thing and work like a partner with your team and really run everything, or we can offer consulting. So maybe you've got an internal team that really knows their stuff, but there's an area they don't know really well and they'd like to get some consulting. We can do that. We also have tons of free guides, free resources, free materials you can check out. All of that gets started at omgcommerce.com, and we can't wait to help you scale profitably.

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