$PAIN: Redefining Meme Coin Aesthetics with Windows 3.0 Nostalgia

I led the design for $PAIN’s launch site, the official meme coin* of the iconic internet meme figure, Hide the Pain Harold. Instead of following the crowd with 8-bit pixel art, we built a Windows 3.0 interface. It worked.

Key Highlights:

  • 🚀 185,976 $SOL raised in 48 hours (record for meme coin presales at the time)
  • 🎨 Created Windows 3.0 interface in meme coin space
  • 👥 Led design team alongside our Head of Product, PM and engineers
  • ⏱️ 6 months of work, launched Feb 2025

The Challenge

Every meme coin website looks the same. 8-bit pixel art everywhere. $PAIN needed to stand out visually while capturing Harold’s “enduring pain” vibe.

The core question:

How do we build hype for the pre-launch? How do we get crypto speculators and meme culture enthusiasts to actually care?

In the meme coin space, visual impact drives social shares. No “wow” factor means getting ignored.

The timeline pressure: We had about six months to build everything, until a surprise 48-hour deadline for the presale airdrop forced us to pivot dramatically.

Research & Insights

Most meme coin sites used ’90s web aesthetics, but not many of them went all-in on a specific OS interface.

The insight: Harold would have used Windows 3.x in his early career. Using the technology for his generation to present his meme coin just made sense.

Windows 3.0 interface (credit Internet Archive)

Art Direction Selection

I tried a bunch of directions—modern pop, Gen-Z aesthetics, pure nostalgia, retro computer UI, etc. The Stickies × 90s Retro (Share Your Pain below) was great for the pain-sharing feature (we called it Painfession), but the retro computer UI won out because it could actually house all features inside a familiar desktop metaphor.

The chosen direction:
So we built a fully functional Windows 3.x desktop interface. Every feature lived in its own draggable window.

PainShare OS draft

PepeCoin later followed the retro Windows OS approach. That validated our direction.

Feature Narrative Naming

I worked with the Head of Product to turn boring functional labels into narrative-driven apps:

FunctionTraditional LabelOur Name
Navigation MenuMenuPain Manager
Meme GeneratorGeneratorPain Generator
Music VideoVideoPain MV
Photo GalleryGalleryPain Tour
Video ClipsVideosPain Player
IntroductionAboutRead Me

The “New Ugly” Call

After pre-launch, the team swapped my subtle blue background for a repeating Harold face pattern to maximise visual impact. I hated it at first—it looked wrong.

But meme coin audiences don’t want a pretty design. They want something so visually obnoxious that they want to share it. The “ugliness” became the point.

Pre-launch and official launch version

When Everything Changed

We spent months on Pain Quests and the Painfession system. Then we got 48 hours’ notice for the presale airdrop. Everything changed. Painfession submissions got dumped onto X and a basic web form. The website kept only the side features.

Features built but couldn’t be launched:

Working with Everyone

  • Head of Product: Translated concepts into narrative experiences
  • PM: Nailing down requirements for complex flows
  • Designer: Delegated features while checking quality
  • CEO: Adapted to direct design feedback, making sure implementation matched intent

I also set the art direction and built social media templates, OG images and meta tags for consistency across channels.

The Solution

The final $PAIN site was a fully interactive Windows 3.x desktop (with a mobile version too). Users could drag windows around, mess with pixelated graphics and hunt for easter eggs.

The UI wasn’t just decoration. It was the story.

404 Page: The classic blue screen of death
Pain Pack: Messenger stickers

Outcome & Impact

  • Record-breaking presale: 185,976 $SOL raised in 48 hours. Highest meme coin presale at the time.
  • Business outcome: Established Stakeland’s credibility. That led to implementation, marketing, GTM and consulting opportunities.
  • Industry influence: PepeCoin’s later Windows XP interface proved we were onto something.
PepeCoin website

What I took away

Scope resilience
The six-month pivot taught me that in crypto, stripping a product down to its essence in 48 hours is a survival skill. The Windows 3.x aesthetic carried the experience even when we had to cut most of the functionality.

The core learning
In meme coin design, “good UX” isn’t always about being intuitive or beautiful. Sometimes it’s about making something so visually arresting that people have to share it, even if it breaks every rule.

My RoleUI/UX Design Lead at Memeland/9GAG
TeamHead of Product, 1 PM, 4 engineers, 2 designers, 1 artist, 1 QA, marketing team
Time~6 months, pre-launch in Feb 2025
Websitepaintoken.com