You Never Forget Your First

When I started my entrepreneurial journey in 2019, I did what all the good podcast ads tell me to do: launch a website on Squarespace. For almost seven years, that was good enough. Sure, there were lots of weird workarounds I had to bang together to get all my different tools working together (I'm looking at you, Code Embed Block), but overall, it got the job done.

Part of why I chose Squarespace was because I am a proud non-coder that knows just enough about coding to be dangerous. I tinkered with HTML back when I was a wee little Geocities kid, I understood conceptually how CSS worked, and I could fake my way through a conversation about Javascript at a bar, but could never write the code myself. I knew roughly what was possible, but not how to get there.

This summer, however, I decided several things:

• I didn't want to pay Squarespace anymore
• I wanted to see if I could vibe code my own website
• I needed to embrace my new business identity as an organizational AI adoption consultant

I didn't decide this but learned it anyway:

• The "I can" feeling is a non-negotiable for becoming AI fluent.

My most important KPI for relaunching a website was not the website, but the feeling of launching a website for the first time.

If you've ever built and launched a website before, you know how easy it is to stand up a page on the internet. But for normies, to whom websites are a deeply technical and arcane construction, it seems impossible. To go from idea to code to URL is magic and only magicians/codemonkeys know the way. Squarespace's entire brand identity is "Anyone can start a website when you use our platform" and I saw myself as an 'anyone' because I'm not a software engineer.

Remember, I'm a proud non-coder that causes problems for real coders.

In August when I got my annual renewal notice from Squarespace, I challenged myself to see how far I could go with just using Claude. I had no idea how to set up the infrastructure, I barely understood the difference between a domain and a host, but I had pluck and a Max subscription so let's gooooooo

I asked Claude to teach me how websites work. I asked Claude to teach me- using diagrams- how my website infrastructure would fit together. I asked Claude to do some design mockups. I asked Claude to help me with brand positioning. I asked Claude to keep things so simple a 4th grader could understand it. I asked Claude to configure my DNS. I asked Claude to fix the misconfigured DNS (my fault!) and then teach me about DNS like a 4th grader (my penance).

When I walked a Claude-generated HTML page to Cloudflare and saw my test site appear, my first reaction was, "Wait, that's all it took?!"

I started to believe: maybe I could accomplish things that I previously thought were exclusively in software land, a not-me place. I wouldn't go so far to call myself a web developer, but I started to see myself as "a guy who could develop a website."

In the learning trade, we call this self-efficacy. The "I can learn this" energy that, when paired with a patient teacher, lets you accomplish things previously thought to be impossible. It's a really important mindset when in the training room, otherwise people don't take risks or challenge themselves.

That "I can learn this" feeling, though, is ephemeral and it vanishes into a subconscious self-image. You probably don't think of yourself as someone who has the potential to type anything you want. You just type, fluently, and feel bad for people who can't.

Even here, in this newsletter, I am vibrantly aware that in early August I struggled to differentiate a domain and a host and by mid-August I was able to explain and fix Domain Name System (DNS) errors. It took a few nights to get it all ironed out, but struggle is how self-efficacy becomes mastery.

After seeing a lot of "let's learn AI!" classes, it's clear that a lot of AI teachers have lost (or never had) a sensitivity to learner self-efficacy. They've forgotten how scary it is to write your first-ever prompt to AI. They've internalized jargon like "context window" and "agentic workflow" which causes AI newbies to just tune out and say that the training was too technical, I'll pass on AI for now, thanks.

Without learners believing that they can learn AI, they will never master AI.

I was reacquainted with this self-efficacy feeling through this website project. I experienced, multiple times, the turning point of "I thought this was impossible" to "Holy smokes I did it!" If you've lost touch with that magical moment, here's how it feels:

• Thrilling
• Empowering
• Confidence-building
• Curious about what else you could do

I see these emotions on the faces of people who come to Show Me Something Cool With AI and my paid trainings, but seeing it and personally experiencing it are very different things.

Let me be clear: these are need-to-have feelings. When people aren't thrilled with their work, or feel disempowered, lack confidence, or couldn't care less, that's how organizations wither. They fail to catch little mistakes (or big mistakes), they don't share feedback up the chain, they don't take risks, and they don't stay after 5pm if they don't have to. Over time, this culture spreads to your high performers.

The dollars speak clearer. MIT's Project NANDA looked at 300 enterprise AI initiatives last year and found 95% of custom enterprise AI tools never made it out of pilot. Everyone quoted that number, because it's quotable and if it bleeds, it ledes.

Nobody quoted the row underneath it: general-purpose chatbots, the ChatGPT-and-Claude stuff, reached deployment 40% of the time.

The AI that works is the AI where one person sits down and does a thing in something we all have access to today.

Same report, same 52 companies: the number one barrier to scaling AI, ahead of model quality and executive sponsorship, was "unwillingness to adopt new tools." Only 40% of companies had bought an AI subscription, but employees at 90% of them were using AI anyway on personal accounts while the official pilots stalled. And the deployments that succeeded started with power users, people who'd already had their holy smokes moment on their own time.

MIT named the problem "the learning gap" and meant tools that don't learn. There's a second learning gap, and it's people who don't believe they can.

Believing is the first step to successful change. Believing is the first step to ROI.

A year from now I won't remember what it felt like to fix a simple DNS error for the first time. It'll be like typing: I'll just do it, fluently, and feel bad for people who can't.

For 78% of you, this is exactly the problem. The people teaching AI in your organization have already forgotten what it felt like. That's not a character flaw. It's how mastery works. But it means the most knowledgeable person in the building is often the worst possible teacher, and the "wait, that's all it took?!" moment is the one thing they can no longer see but desperately need to relive.

I'm going to keep building things I'm bad at. Partly because I like it, but mostly so I don't forget that thrilling/empowering/confidence-building feeling.

If your people need a little dose of self-efficacy, perhaps some AI Fluency for a 100% Human Workforce is the inspiration they need. And if they're MA-based, it's free.

A TL;DR from the CRO

I don't need to be reminded about self-efficacy because I know that I can do anything.

-Roman Noodles, Chief Ruff Officer

Show Me Something Cool With AI: Next Week!

On September 25th, our monthly "holy smokes it's that easy?!" is happening at 1pm ET. This month's optional challenge is inspired by my own holy-smokes moment: Build a landing page.

Landing pages are used all over the place. They're a highly-targeted web page designed to get someone to do something. You might find yourself on a landing page after scanning a QR code, typing in a memorable URL, or clicking an ad.

​With AI, it's incredibly easy to make landing pages, so for SMSCWAI, try making one! Simply go to your AI tool of choice and say, "I want you to make a landing page designed to get people to [action]." Have some fun! Your call-to-action could be:

​"eat more broccoli"
"welcome new souls to hell"
"become a foster parent"
"believe in the most extreme AI hype possible"

​Don't worry about hosting the landing page (unless you want to go the extra mile), just have fun designing a webpage+CTA with AI. Bonus points for interactivity!

​In the last TL;DR, I waxed poetic about being terrified to ride a horse at summer camp, inspired by an upcoming wedding I was going to attend at a summer camp. Fortunately, there was no horseback riding (but there was a pony named Rollo that was so fat and cute that I might have popped).

For three days, I transformed into a more pure version of myself. I jumped into a lake from a rope swing. I decorated my cabin with streamers and tinsel. I allowed my competitive side out during the Color War. I did not get anyone to do camp cheers but I tried.

What was most surprising was discovering that far fewer of my friends were summer camp kids than I suspected. I assumed most people had some lightly-supervised-in-the-woods experience as a moody teenager, but that was my myopic little worldview.

For three days, my whole identity dialed into a sharper focus than it's ever been.

See, I went to more than five summer camps as a kid. My parents would drop me off at a sleepaway camp and I had to build trust and camaraderie with total strangers wicked fast. My formative summers involved establishing or conforming to shared norms, learning to cohabitate with people from wildly different backgrounds, showing up on time and prepared for whatever camp activity was happening, and personally handling failure after getting into LOTS of trouble 😈.

When you look at it that way, no wonder I am who I am.

No wonder other people aren't quite as extra as me.

I was practicing self-efficacy since I was 11.

Your perennial 4th grade summer camp kid,

=Dan from Learn to Scale​

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​PS. Let's meet your camp accountabilibuddy!​