Why Startups Win

The Fallacy of Stability

When I worked with Condé Nast International, helping President Sophia Liao oversee the product and engineering teams, I saw firsthand how ego often derailed long-term strategy. Directors and VPs were more focused on securing their bonuses and promotions than advancing the company’s long-term vision. They protected the status quo because it was safer, personally rewarding, and less risky.

The leadership team often saw greater downside risk in exploring new ideas than the potential upside in embracing them. They weren’t incentivized to experiment with new products or distribution channels. Their compensation hinged on leveraging what already worked, not disrupting it. They were paid to boost margins, not reinvent them.

Complacency vs. Reinvention

Success can be a company’s biggest trap. When you’re “right” for too long, you stop paying attention to how the world is changing. It’s why many companies rise to prominence, only to later fall into irrelevance. They get good at playing one game, but the market keeps shifting, and they fail to adapt to new rules.

The real danger is that success reduces the appetite for risk. Why would a company that’s doing well gamble on risky ideas, especially if those ideas challenge their proven business model? Instead, they double down on what works, fine-tuning and iterating instead of innovating.

Here’s how big companies typically operate:

• They chase trends, mistaking them for long-term competitive advantages.
• They get excited about new ideas but resist adopting new ways of thinking.
• They believe they can easily cater to multiple generations of customers with the same playbook.
• They obsess over data and hate being wrong, so they avoid risks.
• Internal politics slow down or sabotage real progress.

The result?

• If a new idea can be easily bolted onto an existing tool, they go for it.
• If it threatens to upset internal power structures or challenge responsibilities, it stalls.

Why Startups Win: Mastering the Art of the Unknown

In contrast, startups win because they aren’t afraid to take risks or venture into uncharted territory. They aren’t constrained by legacy business models or bogged down by internal politics. The most legendary founders don’t set out to improve on what already exists; they aim to create something entirely new.

To build something truly transformative, you must ignore the trends and the data. Those numbers represent the past. If you focus on the existing market, you’ll find yourself competing with companies that have far more resources. You end up trying to win at their game, with their rules, rather than defining your own.

Instead, focus on what can’t be copied or easily replicated. If you want to create a new category, ask yourself:

• Can I design a category where I have the chance to dominate in the long term?
• What unique leverage can I create that others can’t replicate?
• How can I ensure that advantage compounds over time?

Legendary companies like Tesla, SpaceX, and OpenAI didn’t emerge by chasing trends or obsessing over the competition. They succeeded because their founders focused on creating new categories and solving problems no one else dared to touch. They didn’t just aim to participate in the market—they aimed to redefine it.

In a world where the pace of change is accelerating, following the playbook of the past is a recipe for irrelevance. Success comes not from improving what’s already out there but from envisioning something entirely new—and having the courage to build it.