Envoy Design Lesson One: Enjoy Being a Startup: Why the Startup Mentality Matters at Every Stage

Lesson One: Enjoy Being a Startup: Why the Startup Mentality Matters at Every Stage

25 years is a long time. During our first year, we poured everything into getting the business off the ground. As we grew, I was tempted to leave behind the scrappiness that defined our early startup days. With more employees and processes, things felt stable.

But losing our vital startup mentality could lead to stagnation. Technology changed often, and stagnation meant someone else would leapfrog us. I learned that enjoying being a startup is crucial because there are always new problems to solve. This wasn’t a “phase” but a way of life.

The startup mentality stemmed from why I launched my company. Key components include:
• Comfort with uncertainty
• Bias toward action
• Quick testing of ideas
• Willingness to fail fast
• Flexibility and openness
• Scrappy approach

These traits are vital for companies of any size to adapt in a changing world. Adopting a “permanent beta” mentality is essential. Complacency strikes when things feel comfortable, but that’s precisely when disruption threatens.

As we grew, something very human happened. Work became less about wild experimentation and more about keeping our successful business running. People grew resistant to change. Past wins became reasons why current approaches shouldn’t change. Innovation slowed, even with more resources.

This posed an existential threat, leaving us vulnerable to competitors taking the startup mentality we’d abandoned. Fresh experiments needed to become muscle memory across all teams, not just when growth plateaued.

Innovation is often glorified in myths about brilliant entrepreneurs having “eureka moments.” That is bullshit. While glimpses of genius happen, no company can depend on lightning bolts to stay ahead. Innovation must be a process integrated across the business.

As LinkedIn founder Reid Hoffman said, “if you’re not embarrassed by the first version of your product, you’ve launched too late.” Companies can institutionalize rapid experimentation. Everything can evolve – from products to systems. That awkward first attempt might become a breakthrough.

Nurturing teachability was foundational. This means maintaining an insatiable appetite for learning. This starts at the top. Only at the top. If this has to flow upwards, it won’t likely do that.

The window of viability shrinks fast. Adopting an attitude of “we’re all always learning” positions us to evolve ahead of market shifts. Our professional edge WAS the constant evolution, not informed BY the evolution.

The startup mentality isn’t just a phase – it’s critical at every stage. Let that hustle permeate every decision. If you nurture this mindset, growth stays organic. Your odds of year ten rise when nobody loses that lean startup mentality.

The world moves rapidly. The only strategy certain to fail is assuming past knowledge can coast you through what lies ahead. Innovation is an endless journey. Our most ‘startup-y’ days might still lie ahead.

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