$PAIN: Redefining Meme Coin Aesthetics with Windows 3.0 Nostalgia

I led the design of $PAIN’s launch site—the official meme coin* of Hide the Pain Harold, the iconic internet meme figure, creating a Windows 3.0 visual language that broke from the typical 8-bit pixel aesthetic.

Key Highlights:

  • 🚀 185,976 $SOL raised in 48 hours (record-breaking meme coin presale at the time)
  • 🎨 Created Windows 3.0 interface in meme coin space
  • 👥 Led design team alongside the Head of Product, PM and engineers
  • ⏱️ ~6-month project timeline (launched in Feb 2025)

The Challenge

The meme coin market was saturated with 8-bit pixel art aesthetics. $PAIN needed to differentiate visually while capturing Harold’s “enduring pain” meme culture.

The core question:

How do we create a launch site that builds the hype to drive pre-launch engagement and token sales, while appealing to both crypto speculators and meme culture enthusiasts?

In meme coin culture, visual impact drives social media shareability. Without an immediate “wow” factor, the project risked being ignored among competing launches.

The timeline pressure: We had a ~6-month runway to build comprehensive features, only to face a sudden 48-hour deadline for the presale airdrop that forced us to pivot dramatically.

Research & Insights

Competitive analysis showed most meme coin sites relied on ’90s web aesthetics, but not so many had committed to a specific OS interface.

Harold would have used Windows 3.x in his early career. This aligned perfectly with using the technology of Harold’s generation to present his meme coin.

Windows 3.0 interface (credit Internet Archive)

Visual Direction Selection

I explored multiple styles: modern pop, Gen-Z, nostalgia and retro computer UI. Stickies × 90s Retro UI (Share Your Pain below) was strong for pain-sharing (Painfession), but retro computer UI offered superior flexibility for housing multiple features within a familiar desktop metaphor.

The chosen direction:
A fully functional Windows 3.x desktop interface where each feature lives in its own draggable application window.

PainShare OS draft

This direction was later validated when PepeCoin followed the retro Windows OS interface concept for their own site.

Feature Narrative Packaging

Working with the Head of Product, I transformed functional requirements into narrative-driven applications:

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

The “New Ugly” Decision

After the pre-launch, the team replaced my subtle blue background with a repeating Harold face pattern to maximise visual impact. I initially resisted—this challenges conventional aesthetics.

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

Pre-launch and official launch version

The Six-Month Pivot

After building Pain Quests and Painfession system, we faced a 48-hour deadline for the sudden presale airdrop. This required us to pivot: Painfession submission moved to X and a web form instead of the website, while only side features remained on the website.

Features prepared but not launched:

Cross-Functional Leadership

  • With Head of Product: Translated high-level concepts into narrative experiences
  • With PM: Detailed requirement confirmation for complex flows
  • With the Designer: Delegated features while maintaining quality oversight
  • With the CEO: Adapted to direct design modifications, ensuring implementation quality

I also established Art Direction and created social media templates, OG image and meta tags for visual consistency across channels.

The Solution

The final $PAIN launch site presented a fully interactive Windows 3.x desktop (and mobile) where users could:

  • Experience authentic retro interactions: Draggable windows, pixelated graphics and period-appropriate typography.
  • Engage with narrative-driven features: Each function is wrapped in Harold’s meme mythology.
  • Discover Easter Eggs: Fun surprises 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 user perception and interaction with the story being told.

Outcome & Impact

  • Record-breaking presale: 185,976 $SOL raised in 48 hours (highest meme coin presale at the time).
  • Business outcome: Established Stakeland’s service credibility, leading to implementation, marketing, GTM and consulting opportunities.
  • Industry influence: PepeCoin’s subsequent adoption of the Windows XP interface validated our approach.
PepeCoin website

Reflections

Scope resilience
The six-month pivot taught me that in crypto, being able to strip a product down to its essence within 48 hours is a survival skill. The Windows 3.x aesthetic carried the experience even with drastically reduced 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, even if it breaks every conventional design 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-month. (pre-launch in Feb 2025)
Websitepaintoken.com