I’m going to be honest: I got bored.
For the last decade, I’ve built high-end B2B websites. And after a while, you start to see the same patterns over and over and over again. It’s the “corporate blue” color palette, paired with a clean, rounded font that screams “safety.” It’s the stock photo of diverse people shaking hands in a glass conference room.
It’s professional. It’s clean. And it’s completely invisible.
If you swapped the logos on company websites, would anyone notice? Probably not.
I realized that my own site was falling into the same trap. Don’t get me wrong—it was (and is) fine. As I’m writing this, 98% of it is still fine. But it wasn’t me. I’m a guy who grew up blowing into video game cartridges to make them work. I love design that feels tactile.
So, I decided to experiment with my website.
The website as a validator
I recently wrote about how your website is a validation engine, not a discovery tool.
The gist is this: Most people aren’t finding you through Google Search anymore. They find you on LinkedIn, or through a referral, or a podcast. By the time they click on your URL, they are looking to validate what they’ve already heard. They are looking for a reason to trust you.
But here is the catch:
Boring doesn’t build trust.
Boring builds indifference.
If I tell you I’m a creative partner who can help your business stand out, but my website looks like a template I bought for $49, I have failed the validation test. The medium has to match the message.
The Savannah Bananas Paradox
I love the Savannah Bananas. I’ve studied Jesse Cole’s approach to “Fans First” extensively. They have disrupted baseball by making it fun, chaotic, and unignorable. Their YouTube channel is a masterclass in entertainment.
But have you looked at their website (linked in January 2026)?
It’s… fine. Actually, it feels a bit like a standard sports league site from 2015. It is the only part of their brand that doesn’t feel like the rest of their marketing.
Now, obviously, it’s working for them. They have millions of fans on a waitlist. They don’t need a crazy website to sell tickets.
But I’m not the Savannah Bananas. And neither are you. We don’t have a stadium full of screaming fans (yet). We can’t afford to have a digital home that feels “stagnant” while our marketing claims to be “dynamic.”
Whatever is normal, do the opposite
This brings me to the uncomfortable part.
If you look at the homepage right now, you’ll see a retro, SNES-inspired hero section. It’s pixelated. It’s weird. And it completely clashes with the rest of the site.
You could call crap on me right now and say: “Chris, you’ve been preaching consistency!!! Don’t break consistency!!!”
Yep. I totally did.
But here is the shift: I’m doing it intentionally.
I’m treating the site less like a static brochure and more like a connected universe. Think of these changes as “Easter Eggs.” Right now, it’s just the header. But over time, I’m going to be intentionally breaking it more. There will be other pockets of surprises hidden throughout the site.
It might feel disjointed today. But give it six months, and it will feel like a world.
24 Experiments: A Manifesto for “Play”
I’ve always said a website shouldn’t stay stagnant. But in the B2B space, “updates” usually just mean “posting a blog.”
I want to do better than that.
What if I used the Classic City website the way the Bananas use YouTube? I’m never going to get you to save my URL to your home screen and check it daily. But, what if I gave you a reason to click over from a LinkedIn post? Not because I wrote 500 words on SEO, but because I built something that makes you think: “Hmm, I wonder what that’s about?“
So, here is my pledge:
I am going to run 24 micro-experiments on this website for the next year. For those of you who need to whip out your calculators, I’ll spare you the effort: That’s two hypotheses per month. That is 24 unique features, designs, or interactive elements added to the site.
- Maybe it’s a pricing calculator that actually works.
- Maybe it’s a page layout inspired by a dope comic book cover.
- Maybe it’s a hidden game.
I want to use my own business as the laboratory. I want to show you that B2B doesn’t have to be boring. I want to drive traffic through intrigue, not just information.
This is Experiment #1. The retro-style, video game header.
Stay tuned for #2. We’re just getting started.
