#155 - My AI Dream Team

Welcome back to another AI-forward edition.

Before I dive in, on my flight to a wedding in Puerto Rico last weekend, a woman in front of me was sketching an apple on her drawing pad. She was completely locked in. Headphones on, stencils out, eye-level reference photo, literally focused af.

Her work was incredible, and while I almost told her that "AI could never beat that detail," I held my breath. Because while AI can generate a perfect image of an apple in two seconds, it can’t recreate the human spark I felt watching her create it or the smile she gave me when I complimented her work.

I sat there thinking, AI can’t give me the human exchange that made that image unforgettable; only people can.

Moral of the story: AI is fast, but it doesn't have a soul. Nothing replaces the "score" of a sincere human interaction.

Now, let’s get After It. 

My 2026 AI Team

I’m breaking down my 2026 AI toolkit, not as some tech guru, but as someone who spent a decade of their career underwriting at one of the largest financial service companies.

Most AI content feels like a 300-page sports playbook of jargon, but I’m here to simply give you the "score" in plain English. Like I’ve told you before, my goal is to bridge the gap for non-tech people, showing how these tools can actually complement our human skills rather than replace them.

As I go deeper into how I’m using AI, my aim is to help you in your journey with these tools. Hopefully, the insight can help you see where AI fits into your life, not how everyone else says it should.

So here’s my team as of this writing:

1. ChatGPT is still my Personal Assistant. To me, it’s my go-to for quick searches for my personal needs (traveling, cooking, etc.). I just love how simple it is. 

• The Score: Create "Projects" to bucket your common tasks, like cooking or travel. This keeps your history organized and ensures the AI remembers your specific preferences for each category, making it a better experience overall.

2. Perplexity Comet is my Research Assistant. You can download this incredible browser in the App Store or right to your laptop/desktop. I use this browser because I treat it as my workspace.

• The Score: I keep this browser dedicated to work I do outside of my day job. No bookmarks for Instagram, YouTube, banking websites, etc. (I use Google Chrome for that stuff). By stripping away the digital noise, I’ve found greater focus, and my performance has skyrocketed. This move has done wonders for me, and I believe it can for you, too.

3. Replit is my Coder. I used it to make a writing app and a time-saving holiday tool called Elphie. Even though I’m not a developer, Replit acts as my translator, turning my plain-English ideas into working code so I can build the exact tools I wish existed. Replit can bring your idea to life via an application or even a website in minutes. Wild stuff.

• The Score: Don't wait for a company to build the software you need. If you have a repetitive task or a "manual" headache at work or in your personal life, describe the problem to Replit’s AI agent. You’ll be surprised how fast you can build a custom solution that does the heavy lifting for you. Extra Point: Use ChatGPT to help you create a prompt for your app idea. Brain dump your entire vision to ChatGPT and ask for a simple prompt to copy and paste into Replit to get the app going. Super effective to use the AI with AI.
  

What Else I’m Scoring On

I’ve slowly begun to incorporate Google’s Gemini and Anthropic’s Claude into my rotation. These are other LLMs (large language models) similar to ChatGPT, each with their own strengths.

I like to try other models because they each have their own updates. They’re always making improvements in areas like writing, graphic design, and coding, so whenever I see an update, I jump into the tools and see how they can improve my work. I treat these tools the way athletes treat new gear: try it in practice first, keep what performs best, and bench what doesn’t.

I’m also leaning further into automation behind the scenes. For example, I’d love to build an AI agent that helps with the heavy research lifting for some editions, from gathering sources to summarizing long reports. I believe that would be cool and would save me a ton of time.

But beyond my own setup, I’m really curious how AI can give small, local businesses an edge, things like better customer follow-up, faster content creation, or better inventory and scheduling. With friends and family running small businesses, that’s a space I’m seriously considering exploring more.

In sum, I am so fascinated by what these tools can do for us. I’m enjoying the exploration because I made the decision to have fun with it and not fear it. I’m not looking at this from a doomer POV, I’m looking at this from an optimistic lens. So if you can learn how AI can complement your work, life or anything in between, you won’t just keep up, you’ll quietly start to pull ahead.

The thing that stands out to me most about Dan’s dream team is that Dan is still the MVP of the squad. His teammates make his life easier, but they can’t do all the work while he sits back with his feet up.

• ChatGPT can give him information, but Dan needs to have analyzed the problem, know what to look for, and prompt it accordingly.

• Perplexity Comet can make research easier, but Dan needs to have identified what information is missing or what’s needed to drive his points home.

• Replit can write the code, but Dan needs to have a well-thought-out idea and then articulate it clearly and specifically in the prompt.

This is the part where I tell my students: this is why reading, thinking, problem-solving, and writing are still important! These skills are far from obsolete! Keep challenging yourself and developing your language and critical thinking skills!

But you didn’t sign up for my class, so I won’t do that to you…

(As an aside, I don’t have a dream team. I have a doubles partner, and it’s Perplexity. After trying all the LLM apps, I liked Perplexity the best and have since gotten comfortable. I also like that it has a Google News-ish feature that helps me stay informed. That said, I need to take Dan’s advice and check for updates because I could be missing out!)

Before You Go!

Thanks for reading. Next week, we’ll be back focused on human skills (with AI serving in a more subdued, complementary role.)

In the meantime, if you have any stories, ideas, or things you’ve read that you believe would benefit our readers, feel free to shoot us an email at [email protected]. We’d love to feature you the same way we featured Tim’s story last week.

As always, see you on Tuesday.

Find Dan on LinkedIn

You are now On The Fly & In The Know.