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My Monday Morning Battle: AI Agents, LinkedIn, and the Gritty Reality of Building Outbound

Wow. I made it to Monday. I made it till 11 AM on Monday.


That might not sound like much, but my morning involved carrying my kicking and screaming seven-year-old onto the school bus while the driver gave me a sympathetic, “You’re doing the right thing, dad.” It’s a challenge, you know? Getting structure and discipline in place. But as a dad, I gotta be firm.


And in a weird way, that’s exactly what building a business feels like. You can create all the content in the world, build the perfect product, but if you don’t drag yourself—kicking and screaming—into the promotion, the outbound messaging, the stuff that actually gets you out there, then you’re just creating in a vacuum. A big part of my success has always been outbound, and I finally decided today was the day. All the pieces were in place. No more excuses. It was time to launch back into active outbound mode.


So, I’m getting ready to build out the first piece of my new outbound strategy, and on the side, I’ve got this conversation going with my buddy Mike H. He’s all excited about AI and wants to build an AI agent. And I’m like, for what I do? Let’s try it. I thought, today, I’m gonna build the AI agent.


My Quick, Expensive Detour into Agentic AI

I started messing around, looking into what it would take. And honestly, it took very little time to come to the conclusion that this was not the way. At least, not for what I needed.


First, I looked at Google’s Agentic AI. Cool stuff. You pay a bit more, and you get these new capabilities. But I could tell right away it wasn’t going to do something as complicated as automatically sending a personalized LinkedIn message. You’d think that would be easy, but it’s not. Sure, an AI can create a LinkedIn post. I guarantee you that workflow is beat to death. But sending personal, outbound messages? That’s a whole different game. LinkedIn doesn’t want you to do this. They don’t make it easy. And trying to get Gemini Enterprise to even connect to LinkedIn? It just doesn’t do it.


That’s the crux of it, right? It’s always about how one system talks to another. External communications, security, APIs… that’s where these grand AI visions fall apart.


Then I stumbled on another tool, CrewAI. It’s part of a group that provides toolkits to build and run your own agents. It looked promising—like maybe this could work. But then I saw the pricing. The free plan gets you 50 workflow executions. The next tier, for $25 a month, gets you… another 50. I’m sorry, but that’s like 50 cents an execution. That’s crazy. Every time I send one message on LinkedIn, it costs me 50 cents? I can’t even wrap my head around it. The math immediately was clear to me: my other approach, the one that isn’t fully “agentic,” is the right one.


The Real-Deal: A Tech Stack That Actually Works

So, if a fully autonomous AI agent is a costly dead end for LinkedIn outreach, what does work? For me, it comes down to a more hands-on, robust stack that gives me granular control.


It starts with a virtual desktop. I use a service called Flexidesktop. It’s a virtual machine that’s always on. This is where my automation lives. You can’t run this stuff on your home computer; you need a dedicated environment.


Inside that virtual machine, I run LinkedHelper. Now, this is the key. LinkedHelper isn’t some far-off AI in the cloud; it’s a piece of software that essentially hijacks the browser. It’s like a wrapper. It opens an instance of LinkedIn and acts like a person—clicking, scraping, and messaging, all based on a workflow I design. It’s an idea that makes so much sense. Why reinvent the wheel with complicated APIs when a browser can already do everything you need? If an AI could just operate a browser like a person, everything would be so much easier. LinkedHelper is the closest I’ve found to that.


This isn’t a “set it and forget it” tool. It’s complicated. You have to play with it, test it out, and go small at first. But because it’s more advanced, you get a level of scale and a suite of tools—for scraping profiles, extracting group members, and managing complex sequences—that you just can’t get with simpler, plug-and-play solutions.

Here’s How I’m Firing It Up Today

So, my plan for today is to get this engine running again. I’ve already got my messaging crafted. Now it’s about targeting.


I’m using Sales Navigator inside my LinkedHelper browser to find the right people. For this campaign, I’m trying something a little different. Instead of just searching for job titles, I’m looking for influencers. For example, I might find an executive at a company who has 3,500 followers. That’s a good sign. His followers are likely a pre-qualified audience of people in his industry.


The next step is to use LinkedHelper to scrape a list of his followers. Then, I’ll build a campaign to send InMails to that list. I’ll start small, maybe 20 or 50 messages, to see what the response is like. The goal is to get to a hundred InMails for this target group. Because it’s running in a controlled way that mimics human behavior, it flies under LinkedIn’s radar.


It’s not as sexy as telling a magic AI agent to “go get me leads,” but it’s real. It’s a process. It’s that “chop wood, carry water” work that actually builds the foundation of a business. Once it’s set up, I can even look at bringing in my VA to help manage it, keeping the campaigns running every day. You have to monitor it, check on it, and make sure it’s all working. But the result is a consistent, scalable outreach machine that taps into a side of LinkedIn you didn’t realize was there.


So, that’s my Monday. A little bit of parenting chaos and a whole lot of focused, pragmatic business building. The shiny promise of AI is exciting, but for now, I’m sticking with what works: a powerful, browser-based approach that gives me the control to grow my business, one thoughtful message at a time.


Anyway, I hope you got some value out of this. If you want to talk shop about any of this stuff—strategic solution design, growth marketing, or how to make these products work—you can find me on LinkedIn.


Have a great Monday, everybody.


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