$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 explored various directions: modern pop, Gen-Z, nostalgia, retro computer UI, etc. The Stickies × 90s Retro (Share Your Pain below) worked well for pain-sharing (we called it Painfession), but retro computer UI gave us more flexibility to house multiple 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 with a repeating Harold face pattern to maximise visual impact. I initially resisted—it challenges conventional aesthetics.

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

Pre-launch and official launch version

When Everything Changed

We spent months building Pain Quests and the Painfession system. Then we got 48 hours’ notice for the presale airdrop. We had to pivot hard: Painfession submissions moved to X and a web form. Only side features stayed on the website.

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 (and mobile version) where users could:

  • Experience authentic retro interactions: Draggable windows, pixelated graphics and period-appropriate typography.
  • Engage with narrative-driven features: Use features wrapped in Harold’s meme mythology.
  • Discover Easter Eggs: Find easter eggs on unready features and the 404 page.
404 Page: The classic blue screen of death
Pain Pack: Messenger stickers

The design showed how UI aesthetic shapes how users perceive and interact with the story.

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” doesn’t always mean “intuitive and beautiful”. Sometimes it means creating something so visually arresting that users can’t help but 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