In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss autonomous AI agents and the mindset shift required for total automation.

You’ll learn the risks of experimental autonomous systems and how to protect your data. You’ll discover ways to connect AI to your calendar and task managers for better scheduling. You’ll build a mindset that turns repetitive tasks into permanent automated systems. You’ll prepare your current workflows for the next generation of digital personal assistants.

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What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode.

Christopher S. Penn [00:00]: In this week’s In Ear Insights, let’s talk about autonomous AI. The talk of the town for the last week or so has been the open source project first named Claudebot, spelled C L A W D. Anthropic’s lawyers paid them a visit and said please don’t do that. So they changed it to Maltbot and then no one could remember that. And so they have changed it finally now to Open Claw. Their mascot is still a lobster. This is in a condensed version, a fully autonomous AI system that you install on a.

Christopher S. Penn [00:35]: Please, if you’re thinking about on a completely self contained computer that is not on your main production network because it is made of security vulnerabilities, but it interfaces with a bunch of tools and hasn’t connected to the AI model of your choice to allow you to basically text via WhatsApp or Telegram with an agent and have it go off and do things. And the the pitch is a couple things. One, it has a lot of autonomy so it can just go off and do things. There were some disasters when it first came out where somebody let it loose on their production work computer and immediately started buying courses for them. We did not see a bump in the Trust Insights courses, so that’s unfortunate. But the idea being it’s supposed to function like a true personal assistant.

Christopher S. Penn [01:33]: You just text it and say hey, make me an appointment with Katie for lunch today at noon PM at this restaurant and it will go off and figure out how to do those things and then go off and do them. And for the most part it is very successful. The latest thing is people have been just setting it loose. They a bunch of folks created some plugins for it that allow it to have its own social network called Mult Book, where which is a sort of a Reddit clone where hundreds of thousands of people’s open Claw systems are having conversations with each other that look a lot like Reddit and some very amusing writing there.

Christopher S. Penn [02:12]: Before I go any further Katie, your initial impressions about a fully autonomous personal AI that may or may not just go off and do things on its own that you didn’t approve?

Katie Robbert [02:24]: Hard pass period. No, and thank you for the background information. So I, you know, as I mentioned to you, Chris Offline, I don’t really know a lot about this. I know it’s a newer thing, but it’s like picked up speed pretty quickly. I thought people were trying to be edgy by spelling it incorrectly in terms of it being part of Claude, but now understanding that Claude stepped in and was like heck no. That explains the name because I was very confused by that. I was like, okay, you know, I, I think a lot of us have always wanted some sort of an admin or personal assistant for paperwork or, you know, making appointments and stuff. Like, so I can definitely see the potential.

Katie Robbert [03:10]: But it sounds like there’s a lot of things that need to be worked out with the technology in terms of security, in terms of guardrails. So let’s say I am your average, everyday operations person. I’m drowning in the weeds of admin and everything, and I see this as a glimmer of hope. And I’m like, ooh, maybe this is the thing. I don’t know a lot about it. What do I need to consider? What are some questions I should be asking before I go ahead and let this quote unquote, autonomous bot take over my life and possibly screw things up?

Christopher S. Penn [03:54]: Number one, don’t use this at work. Don’t use this for anything important. Run this on a computer that you are totally okay with just burning down to the ground and reformatting later. There are a number of services like Cloudflare, with Cloudflare’s workers and Hetzner and a bunch of other companies that have, they very quickly, very smartly rolled out very inexpensive plans where you can set up a open clause server on their infrastructure that is self contained and that at any point you just, you can just hit the self destruct button.

Katie Robbert [04:27]: Well, and I want to acknowledge that because you said, you know, you started by saying, like, any computer, I don’t know a lot of people besides yourself and other handful who have extra computers lying around. You know, it’s not something that the average, you know, professional has. You know, some of us are using, you know, laptops that we get from the company that we work for and if we ever leave that job, we have to give that computer back. And so we don’t have a personal computer.

Speaker 3 [04:59]: So it’s number one.

Katie Robbert [05:01]: It’s good to know that there are options. So you said Cloudflare, you said, who else?

Christopher S. Penn [05:06]: Hetzner, which is a German company, basically, anybody that can rent you a server that you can use for this type of system. What the important thing here is not this particular technology, because the creator has said, I made this for myself as kind of a gimmick. I did not intend for people to be deploying clusters of these and turning into a product and trying to sell it to people. He’s like, that’s not what it’s for. And he’s like, I intentionally did not put in things like security because I didn’t want to bother. It was a fun little side project. But the thing that folks should be looking at is the idea. The idea of. We’ve done some episodes recently on the Trust Insights livestream about Claude Code and Claude Cowork, which Cowork, by the way, just got plugins.

Christopher S. Penn [05:58]: So all those skills and things, that’s for another time, but when you start looking at how we use things like Claude code. This morning when I got into the office, I fired up Claude Code, opened it in my Asana folder and said, give me my daily briefing. What’s going on? It listed all these things and I immediately just turn on my voice memo thing. I said, this is done. Let’s move this due date, this is done. And it went off and it did those things for me. Someone who hated using project management software like this now, I love it. And I was like, okay, great, I can just tell it what to do. And it does. And I actually looked. I opened up an asana looked, and it not only created the tasks, but it put in details and descriptions and stuff like that.

Christopher S. Penn [06:44]: And it now also prompts me, hey, how much time do you think this will take? I’ll put that in there too. I’m like, this is great. I don’t have to do anything other than talk to it. Something like openclaw is the next evolution of a thing like Claude Code or Open or Claude Coerc, where now it’s a system that has connection to multiple systems, where it just starts acting like a personal assistant. I’m sure if I wanted to invest the time, and I probably will, I’m going to make a Python connector to my Google Calendar so that I can say in my Asana folder, hey, now that you’ve got my task list for this week, start blocking time for tasks.

Christopher S. Penn [07:26]: Fill up my calendar with all the available slots with work so that I can get as much done as possible, which will make me more productive at a personal level. When people see systems like OpenClaw out there, they should be thinking, okay, that particular version, not a good idea. But we should be thinking about how will our work look when we have a little cloud bot somewhere that we can talk to, like a PA and say, fill up my calendar with the important stuff this week.

Speaker 3 [07:58]: Right?

Christopher S. Penn [07:59]: Yeah, because you’ve connected it to your son, you’ve connected your Google Calendar, you’ve connected to your HubSpot. You could say to it, hey, as CEO, you could say, hey, open agent, fill Up. Go look in HubSpot at the top 20 deals that we need to be working on and fill up John’s calendar with exact times that he should be calling those people. Right.

Katie Robbert [08:24]: I’m sorry, in advance. I’m gonna do that.

Christopher S. Penn [08:27]: He’s been saying, hey, it looks like Chris has gotten some time on Friday open agent. Go and look in Chris’s asana and fill up his day. Make sure that he’s getting the most important things done. That as a manager, you know, with permission, obviously is where this technology should be going so that you could, like, this is the vision. You could be running the company from your phone just by having conversations with the assistant. You know, you’re out walking Georgia and you’re like, oh, I forgot these three things and I need to do lunch here and I do this. Go, go take care of it. And like a real human assistant, it just does those things and comes back and says, here’s what I did for you.

Katie Robbert [09:10]: Couple questions. One, you know, I hear you when you’re saying this is how we should be thinking about it. You are someone who has more knowledge than the most of us about what these systems can and can’t do. So how does someone who isn’t you start thinking about those things? Let’s just start with that question. You know, and I know that this, know I always come back to. I remember you wrote this series when we worked at the agency and it was for IBM. So you know, for those who don’t know, Chris is a, what, eight year running IBM champion. Congratulations on that. That is, I mean that’s a big deal.

Katie Robbert [09:56]: But it was the citizen analyst post series that always stuck with me because I always, I’d never heard that terminology, but it was less about what you called it and more about the thinking behind it. And I think we’re almost, I would argue that we’re due for another citizen analyst, like series of posts from you, Chris, like, how do we get to thinking about this the way that you’re thinking about it or the way that somebody could be looking at it and you know, to borrow the term the art of the possible, like, how does someone get from. There’s a software, I’ve been told it does stuff, but I shouldn’t use it. Okay, I’m going to move on with my day.

Katie Robbert [10:41]: Like, how does someone get from that to, okay, let me actually step back and look at it and think about the potential and see what I do have and start to cobble things together. You know, I feel like it’s maybe the difference between someone who can cook with a recipe and someone who can cook just by looking inside their pantry.

Christopher S. Penn [11:01]: I, the cooking analogy is a great one. I would definitely go there because you have to know when you walk into the kitchen what’s in here, what are the appliances, what do we have for ingredients, how do those ingredients go together? Like for example chocolate and oatmeal generally don’t go well together. At least not as a main. It’s kind of like when you look at the 5PS platform we always say this in most situations do not start with the technology, right? That’s, that’s a recipe usually for not things not going well. But part of it is what’s implicit in platform is that you know what the platforms do, that you know what you have. Because if you don’t know what you have and you don’t know how to use them, which is process, then you’re not going to be as effective.

Christopher S. Penn [11:46]: And so you do have to take some time to understand what’s in each of the five P’s so that you can make this happen. So in the case of something like an open claw or even actually let’s go, let’s take a step back. If you are a non technical user and you’re, let’s say you decide I’m going to open up Claude Cowork and try and make a go of this, the first question I would ask is well what things can it connect to? That’s an important mindset shift is what can I connect this to? Because we’ve all had the experience where we’re working like a chat GPT or whatever and it does stuff and it’s like fun and then like well now I got go be the copy paste monkey and put this in other systems.

Christopher S. Penn [12:29]: When you start looking at agentic AI that where do I have to copy paste? This should be a shorter and shorter list every day as companies start adding more connectors. So when you go to Claude Cowork you see Google Drive, Google Calendar, fireflies, Asana, HubSpot, etc. And that’s your first step is go what does it connect to? And then you take a look at your own process in the 5ps and go of those systems. What do I do? Oh I every Monday I look in HubSpot and then I look in Google Analytics and then I look here and look here and go well if I wrote down that process as a standard operating procedure and I handed that sop as a document to Claude in cowork. I could literally asking, hey, how much of this could you do for me?

Christopher S. Penn [13:21]: And just tell me what to look at. So first you got to know what’s possible. Second, you got to know your process. Third, you have to ask the machine can how much of this can you do? And then you have to think about and this is the important question, what, Given all this stuff that you have access to, what could you do that. I am not thinking about that. I’m not doing that. I should be. The biggest problem we have as humans is we do not. We are terrible at white space. We are terrible at knowing what’s not there. We. We look at something we understand, okay, this is what this thing does. We never think, well, what else could it do that I don’t know? This is where AI is really smart because it’s been trained on all the data.

Christopher S. Penn [14:09]: It goes well, other people also use it for this. Other people do this. Or it’s capable of doing this. Like, hey, you’re asana. Because it contains a rudimentary document management system, could contain recipes. You could use it as a recipe book. Like you shouldn’t, but you could. And so those are kind of the mindset things. And the last one I’ll add to that. There’s something that I know, Katie, you and I have been talking about as we sort of try and build a. A co AI person as well as a co CEO to sort of the mirror the principles of trust. Insights is one of the first things that I think about every single time I try to solve a problem is this a problem that can solve with an algorithm? This is something that I Learned from Google 15 years ago.

Christopher S. Penn [14:56]: Google in their employee onboarding says we favor algorithmic thinkers. Someone who doesn’t say, I’m going to solve this problem. Somebody who thinks, how can I write an algorithm that will solve this problem forever and make it go away and make it never come back? Which is a different way of thinking.

Katie Robbert [15:14]: That’s really interesting.

Speaker 3 [15:17]: Huh?

Katie Robbert [15:18]: I like that. And I feel like. I feel like offline. I’m just going to sort of like.

Speaker 3 [15:23]: Make that note for us.

Katie Robbert [15:24]: I want to explore that a little bit more because I really, I think that’s a really interesting point.

Speaker 3 [15:31]: And.

Katie Robbert [15:31]: It does explain a lot around your approach to looking at this. These machines, as you’re describing, sort of the people are bad with the white space. It reminds me of the case study that was my favorite when I was in grad school. And it was a company that at The Time was based in Boston. I honestly haven’t kept up with them anymore. But it was a company called Ideo and ido. One of the things that they did really well was they did basically user experience. But what they did was they didn’t just say, here’s a thing, use it. Let us learn how you’re using the thing. They actually went outside and it wasn’t the here’s a thing, use it. It’s let us just observe what people are doing and what problems they’re having with everyday tasks and where they’re getting stuck in the process.

Katie Robbert [16:28]: I remember this is just a side note, a little bit of a rant. I brought this case study to my then leadership team as a way to think differently about how, you know, because were sort of stuck in our sales pipeline and sales were zero and blah, blah. And I got laughed out of the room because that’s not how we do it. This is how we do it. And, you know, I felt very ashamed to have tried something different. And it sort of was like, okay, well that’s not useful. But now fast forward jokes on them. That’s exactly how you need to be thinking about it.

Katie Robbert [17:03]: So it just, it strikes me that we don’t necessarily, yes, we need to understand the software, but in terms of our own awareness as humans, it might be helpful to sort of maybe isolate certain parts of your day to say, I am going to be very aware and present in this moment when I’m doing this particular task to see.

Speaker 3 [17:31]: Where am I getting stuck, where am.

Katie Robbert [17:32]: I getting caught up, where am I getting distracted and then coming back to it? And so I think that’s something we can all do. And it sounds like, oh, that’s so much extra work, I just want to get it done. Well, guess what?

Speaker 3 [17:45]: Those tasks that you’re just trying to.

Katie Robbert [17:47]: Survive and get through, they are likely the ones that are best candidates for AI. So if we think back to our other framework, the TRIPS framework, which is.

Speaker 3 [17:57]: In this list somewhere, here it is.

Katie Robbert [18:01]: Found it. Trust, insights, AI trips, time, repetitiveness, importance, pain, and sufficient data. And so if it’s something that you’re doing all the time, you’re just trying to get through, may be a good candidate for AI. You may just not be aware that it’s something that AI can do. And so, Chris, to your point, it could be as straightforward as. All right, I just finished this report. Let me go ahead and just record voice, memo my thoughts about how I did it, how it goes, how often I do it, give it to even something like a Gemini chat and say, hey, I do this process, you know, three times a week. Is this something AI could do for me? Ask me some questions about it and maybe even parts of it could be automated.

Katie Robbert [18:50]: Like that to me is something that should be accessible to most of us. You don’t have to be, you know, a high performing engineer or data scientist or you know, an AI thought leader to do that kind of an exercise.

Christopher S. Penn [19:07]: A lot of, a lot of the issues that people have with making AI productive for them almost kind of reminds me of waterfall versus agile in the sense of, hey, I need to do this thing. And you know, this is this massive big project and you start digging like, I give up, I can’t do it. As opposed to a more bottom up approach, you go, okay, I do this as possible. What if I can automate just this part? What if I can automate just this part? What if I can do this? And then what you find over time is that then you start going, well, what if I glue these parts together? And then eventually you end up with a system. Now that gets you to V1 of like, hey, this is this janky cobbled together system of the way that I do things.

Christopher S. Penn [19:47]: For example, on my YouTube videos that I make myself personally, I got tired of putting just basically changing the text in Canva every video. This is stupid. Why am I doing this? I know image magic exists. I know this library, that library exists. So I wrote a Python script, said, I’m just going to give you a list of titles. I’m going to give you the template, the placeholder, I’ll tell you what font to use, you make it. This is not rocket surgery. This is not like inventing something new. This is slapping text on an image. And so now when I’m in my kitchen on Sundays cooking, I’ll record nine videos at a time. AI will choose the titles and then it will just crank out the nine images. And that saves me about a half an hour of stupid typing, right?

Christopher S. Penn [20:33]: That stupid typing is not executive function. I’m not outsourcing anything valuable to AI. Just make this go away. So if you think and you automate little bits everywhere you can and then you start gluing it together, that gets you to V1. And then you take a step back and go, wow, V1 is a hot mess of duct tape and chewing gum and bailing wire. And then that you say to with, in partnership with your AI, reverse engineer the requirements of this janky system that we’ve made to A requirements document. And then you say, okay, now let’s build v2, because now we know what the requirements are. We can now build V2 and then V2 is polished. It’s lovely. Like my voice transcription system V1 was a hot mess.

Christopher S. Penn [21:16]: V2 is a polished app that I can run and have running all the time and it doesn’t blow up my system anymore. But in terms of thinking about how we apply AI and the sort of AI mindset, that’s the approach that I take. It’s not the only one by any means, but that’s how I think about this. So when someone says, hey, open call is here, what’s the first thing I do? I go to the GitHub repo, I grab a copy of it, make a copy of it, because stuff vanishes all the time. And then I dive in with an AI coding tool just to say, explain this to me what’s in the box.

Christopher S. Penn [21:53]: If you are a more technical person, one of the best things that you can do in a tool like Claude code is say, build me a system diagram, analyze the code base and build me system. Don’t make any changes, don’t do anything, just explain the system to me and you’ll look at it and go, oh, that’s what this does. When I’m debugging a particularly difficult project, every so often I will say, hey, make a system diagram of the current state and it will make one. And I’ll be like, well, where’s this thing? It’s like, oh yeah, that should be there. I’m like, yeah, no kidding it should be there. Would you please go and fix that? But having to your point, having the self awareness to take a step back and say show me the system works really well.

Christopher S. Penn [22:39]: If you want to get really fancy, you could screen record you doing something, load that to a system like Gemini and say, make me a process diagram of how I do this thing. And then you can look at it with a tool like Gemini because Gemini does video really well and say, how could I make this more efficient?

Katie Robbert [22:59]: I think that’s a really good entry point for most of us. Most machines, Macs and PCs come with some sort of screen recorder built in. There’s a lot of free tools, but I think that’s a really good opportunity to start to figure out like, is this something that I could find efficiencies on?

Speaker 3 [23:19]: Do I even have documentation around how I do it?

Katie Robbert [23:22]: If not, take this video and create some and then I can look at it and go, oh, that’s not right. The thing I want to reinforce, you know, as we’re talking about these autonomous, you know, virtual assistants, executive assistants, you know, these bots that are going to take over the world, blah, blah. You still need human intervention. So, Chris, as you were describing, the process of having the system create the title cards for your videos, I would imagine, I would hope, I would assume that you, the human reviews all of the title cards ahead of, like, before posting them live, just in case you got on a particular rant in one video, it was profanity laced and the AI was like, oh, well, Chris says this particular F word over and over again, so it must be the title of the video.

Katie Robbert [24:14]: Therefore, boom, here’s title card. And I’m just going to publish it live. I would like to believe that there is still, at least in that case, some human intervention to go. Oh, yeah, that’s not the title of that video. Let me go ahead and fix that. And I think that’s. Go ahead.

Christopher S. Penn [24:29]: There isn’t human intervention on that because there’s an ideal customer profile that is interrogated as part of the process to say, would the ICP like this? And the ICP is a business professional. And so, you know, I’ve had it say, the ICP would not like this title and it will just fix itself. And I’m like, okay, cool. So you, to your point, there was human intervention at some point, and then we codified the rules with an ideal customer profile. Say, this is what the audience really wants.

Katie Robbert [24:54]: And I think that’s okay.

Speaker 3 [24:56]: I think you at least need to.

Katie Robbert [24:57]: Start with that for V1. You should have that human intervention as the QA. But to your point, as you learn, okay, this is my ideal customer, and this is what they want. This is the feedback that I’ve gotten on everything. Take all of that feedback, put it into a document and say, listen to this feedback every time you do something. Make sure we’re not continually making the same mistakes. So it really comes down to some sort of a QA check, a quality assurance check in the process before you just unleash what the machines create to the public.

Christopher S. Penn [25:31]: Exactly. So to wrap up Open Claw, Claudebot, Multbot, slash, whatever they want to call it this week is by itself not something I would recommend people install. But you should absolutely be thinking about, what does a semi autonomous or fully autonomous system look like in our future, how will we use it? And laying the groundwork for it by getting your own AI mindset in place and documenting the heck out of everything that you do so that when a production ready system like that becomes available, you will have all the materials ready to make it happen and make it happen safely and effectively.

Christopher S. Penn [26:09]: If you’ve got some thoughts or hey, you installed open claw and burned down your computer pot, drop by our free slot group Go to trust insights AI analytics for marketers where you and over 4,500 marketers are asking and answering each other’s questions every single day. And wherever it is you watch, listen to the show. If there’s a channel you’d rather have it on, said go to Trust Insights AI TI Podcast. You can find us all the places fine podcasts are served. Thanks for tuning in to talk to you on the next one.

Speaker 3 [26:40]: Want to know more about Trust Insights? Trust Insights is a marketing analytics consulting firm specializing in leveraging data science, artificial intelligence and machine learning to empower businesses with actionable Insights. Founded in 2017 by Katie Robert and Christopher S. Penn, the firm is built on the principles of truth, acumen and prosperity. Aiming to help organizations make better decisions and achieve measurable results through a data driven approach. Trust Insight specializes in helping businesses leverage the power of data, artificial intelligence and machine learning to drive measurable marketing roi. Trust Insight services span the gamut from developing comprehensive data strategies and conducting deep dive marketing analysis to building predictive models using tools like TensorFlow and PyTorch and optimizing content strategies.

Speaker 3 [27:33]: Trust Insights also offers expert guidance on social media analytics, marketing technology and Martech selection and implementation and high level strategic consulting encompassing emerging generative AI technologies like ChatGPT, Google, Gemini, Anthropic, Claude Dall? E, Midjourney Stock, Stable Diffusion and metalama. Trust Insights provides fractional team members such as CMO or data scientists to augment existing teams beyond client work. Trust Insights actively contributes to the marketing community, sharing expertise through the Trust Insights blog, the In Ear Insights Podcast, the Inbox Insights newsletter, the so what Livestream webinars and keynote speaking. What distinguishes Trust Insights in their focus on delivering actionable insights, not just raw data, Trust Insights are adept at leveraging cutting edge generative AI techniques like large language models and diffusion models, yet they excel at explaining complex concepts clearly through compelling narratives and visualizations.

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