The Art of Failing Fast: Lessons from the Trenches

By Douglas Gan | February 4, 2026

"Fail fast" is a cliché in Silicon Valley, but in Singapore and much of Asia, failure is often a taboo. I know this because I've lived it. Before I was the CEO of GBCI Ventures, before I sold ShowNearby, and before I was recognized as a "Young Professional of the Year," I was a founder who had to learn the hard way.

My journey didn't start with a unicorn; it started with selling marbles and Dragonball cards in school. I made $20,000 by age 16, but I also learned that markets shift, trends die, and if you're holding the bag when the music stops, you lose.

The VanityTrove Pivot: A Case Study in Agility

One of the most defining moments of my career was with VanityTrove, a beauty sampling business I co-founded. We started with a simple model: subscription boxes. Customers paid a monthly fee to receive a box of curated beauty samples. It was a hot trend, and we grew quickly.

But then, the data started to tell a different story.

We realized that while the subscription model was great for consumer discovery, it was a logistical nightmare and the unit economics were becoming squeezed. We were shipping heavy boxes, dealing with inventory, and the churn was real.

The Decision to Pivot

We had two choices:

Keep pushing a model that was bleeding margins but had top-line growth.
Fail the model fast and pivot to something scalable.

We chose the latter. We looked at our assets—a massive community of beauty enthusiasts and a platform for reviews. We pivoted VanityTrove from a subscription box company into a digital beauty community and media platform.

This wasn't easy. We had to tell our investors and our team that the "core" business was changing. But because we moved fast, we survived. We transformed into a platform that connected brands with influencers and consumers directly, cutting out the heavy logistics.

Global Lessons in Pivoting

We weren't the only ones. History is filled with giants who only survived because they killed their darlings quickly.

Slack: The Failed Game

Stewart Butterfield didn't set out to build a workplace chat app. He raised millions to build a game called Glitch. It was a beautiful, quirky MMORPG, but it wasn't growing. The "failure" was the game. But the "success" was hidden inside their internal communication tool.

They made the hard call: shut down the game (failing fast) and pivot entirely to the tool. That tool became Slack, which sold to Salesforce for $27.7 billion. If they had stubbornly stuck to the game for another year, they would have died.

Airbnb: The Cereal Hustle

In 2008, Airbnb was dying. Investors didn't get it. They were broke. To keep the lights on, the founders didn't just code; they sold novelty cereal boxes—Obama O's and Cap'n McCain's—during the election.

They realized their initial idea of just "airbeds" wasn't enough. They iterated rapidly on photography, trust, and payments. They failed at the "bed and breakfast" part multiple times until they realized the real value was in belonging. They didn't wait for permission to change the model; they did whatever it took to survive.

How to Fail Smart

Failing fast isn't about being reckless; it's about being data-driven.

Set Kill Criteria: Before you launch a feature or a campaign, define what failure looks like. If you don't hit X metric by Y date, you kill it. No emotions.
The $2 Lesson: When I was 4 years old, I sold a toy car to a classmate for $2. It was my first "exit." But I also had ventures in school that went nowhere. I learned early that time is your most expensive capital. If an idea isn't getting traction, you are paying for it with your life.
Transparency: When things aren't working, tell your stakeholders immediately. I've found that investors respect a founder who says, "This isn't working, here's why, and here's what we're doing next," far more than one who hides the bad news until it's too late.

From Failure to $100 Million Fund

My failures taught me more than my successes. They taught me risk management, resilience, and the importance of unit economics. When I founded GBCI Ventures and launched a $100 million smart city fund, I wasn't looking for founders who had a perfect track record. I was looking for founders who had scars.

I wanted to know: When did you fail? How did you handle it? And how fast did you get back up?

If you're building a startup today, don't fear the failure. Fear the slow death. Fear the zombie startup that is neither growing nor dying.

Fail fast. Learn faster. And then build something that lasts.