The Stoic Startup: Building Unbreakable Companies from the Inside Out

An Upstart Collective Lunch and Learn event (free to all Portland entrepreneurs and founders, just bring your own lunch)

The Stoic Startup: Building Unbreakable Companies from the Inside Out

What if the secret to startup resilience isn't found in market analysis or funding rounds, but in ancient philosophy?

Most entrepreneurs obsess over the externals: What product to build? Which market to enter? How much can we charge? Where's the funding? They architect business models and competitive strategies, yet overlook the most critical design decision of all—what kind of company they're actually creating.

Here's the inconvenient truth: Companies built to chase external results—profit, growth metrics, market dominance—become reactive, fragile, and burn out their people pursuing outcomes they can't control.

But what if there was another way?

Enter the Stoic Startup. Instead of optimizing for external validation, these companies are engineered for internal excellence. They cultivate virtue as their core operating system, creating organizations that don't just weather disruption—they get stronger because of it.

Everyone claims they want to build a "great" company. But without a clear definition of greatness, how do you architect for it? Just as you wouldn't ship code without specifications, you can't build an excellent company without intentional design.

This talk reveals the blueprint for what we call the Unbreakable Company—and why the Stoics had it figured out 2,000 years before Silicon Valley existed.

Ready to build something that lasts?

Erick Cloward is a leadership coach, host of the Stoic Coffee Break podcast, and author of Stoicism 101. A former CTO and software engineer with over 25 years in tech, he's worked with startups across Oregon, the Netherlands, and London. His mission is to help leaders build resilient, unbreakable organizations by blending Stoic philosophy with practical leadership.