My AI Agent Experiment (and What You Can Learn From It)

From automating sales calls to onboarding clients, here’s how agents might reshape our work

It feels like AI agents have become one of the buzz terms of 2025. Everyone is talking about them, but if you ask ten different people what an “AI agent” actually is, you will probably get ten different answers. For most people, the mental image is just another chatbot or digital assistant. The reality and the opportunity is much bigger.

Think about how AI has evolved over the past few years. We started with basic chat assistants: type in a question, get a response. Then came more advanced assistants that could summarize, draft, or pull information.

Agents take it a step further. They don’t just respond. They act. An AI agent can complete a task for you and take care of the mundane, everyday work. They can make cold calls, send emails, or organize files and data. At some point, we will each have thousands of agents running in the background, quietly doing different things for us.

My First Experiment

I ran a fun experiment using What’s Trending, my media company, and HighLevel’s AI Agent. I uploaded documentation, pitch decks, and sponsor pricing sheets into the system. Then I set up the AI agent as if someone was “calling” to ask: How do I partner with What’s Trending?

Instead of just answering questions, the agent could:

  • Send over the right sponsorship deck instantly

  • Follow up with a customized email on my behalf

  • Even schedule a follow-up call

All without me needing to lift a finger, because the agent had everything it needed to own that process.

Now, my company is not exactly a service-based business, so the experiment was more for fun. But I do think this can work well for a variety of different service-based industries. Brick and mortar businesses, restaurants, hotels, salons, and spas could have agents handling bookings, reminders, and upsells.

  • Retail shops could have agents answering product questions and processing returns

  • Creators and coaches could have agents managing client onboarding, FAQs, and follow-up tasks

Anywhere a business relies on back-and-forth communication with customers, as well as specific follow-up, AI agents can step in to save time, reduce friction, and streamline operations. AI agents can help manage your internal workflows too: sales pipelines, lead nurturing, and all the unglamorous admin tasks that usually fall through the cracks.

Reality Check

Of course, it is not all smooth sailing. There have been some very public missteps with AI agents—from Anthropic’s vending machine experiment that behaved unpredictably to enterprise pilots that failed to deliver results at scale. One Carnegie Mellon study even found agents missed nearly 70 percent of basic office tasks.

As Jeremiah Owyang, Venture Capitalist at Blitzscaling Ventures, shared, some of these mistakes are par for the course. Innovation always comes with false starts and failures. In fact, in disruptive cycles, the stumbles usually signal that the technology is being pushed into real-world use cases.

The winners will emerge, and for all of us, the real question is how we stay curious enough to learn, test, and adapt our workflows. Most businesses will have fewer people and more tools, and AI agents will be a core part of that shift. That is why I do this newsletter. I want to try things, share what works and what does not, and help all of us get a head start on what is coming next.

The Takeaway From My AI Agent Experiment

What stood out to me about HighLevel is that the agent lives directly inside their CRM. Because all your customer data, messages, and processes are already in one place, the AI actually has the context to act like part of your team.

For industries built on relationships, service, and repeat customer interactions, this could be a game-changer. And for creators and marketers like me, it is at least worth experimenting with, especially when it comes to sales, business development, and launching products, events, and courses.

They are about to end their summer promotion on September 1, where you can get 30 days to try it out for free. Here is a link for my community. Go check it out—you do not know what is possible when it comes to AI without playing with the tools.

Sponsored by HighLevel: HighLevel is an all-in-one sales and marketing platform trusted by thousands of businesses worldwide. Their new AI agent tools help you automate customer interactions, streamline workflows, and close more deals—all under one roof.

RSVP to join me in San Francisco!

I’ll be in San Francisco on September 4 with Creators 4 Mental Health! We’re hosting an invite-only mixer and panel bringing together creators, press, and industry leaders to tackle burnout, launch CreatorCare.co, and highlight new creator-first tools.

Big thanks to Collective Voice and Bay Area Creator Economy for partnering with me on this.

Plus, vote for my SXSW panel…

It’s that time of year again. SXSW is coming up fast. I’m excited to share our panel on how creators are balancing making content with being human. SXSW PanelPicker Community voting is open through August 24, and I’d love your support.

Other headlines to check out:

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Creator Economy

Web3 

🎧 New Episode of The AI Download: From Hype to Reality: Investing in AI with Jeremiah Owyang

On this week’s AI Download, I sat down with Jeremiah Owyang, venture capitalist, technologist, and founder of Llama Lounge, the largest AI event in San Francisco. We got real about the AI boom. Yes, billions are pouring in, but what is actually working and what is just hype?

We broke down how lean AI startups are pulling in millions with only a handful of people, why top talent is in such crazy demand, and why community and networks matter as much as the tech itself. Jeremiah and I also dug into the tough stuff, including the ethics, the pressure on founders, and how AI agents are already reshaping work and customer service.

Listen to the full conversation now:

Gentle Reminder 🙏

“The best way to predict the future is to invent it.” — Alan Kay

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