The Innovator’s Dilemma

Three lessons for leaders on speed, experimentation, and creativity

Author

Reade Milner
September 23, 2025

This 3-minute read brought to you by the team at Rogue Pine

In this issue, you'll learn:

The Innovator’s Dilemma (and Other Observations)

Startups win by moving faster than bigger companies. 

But speed alone isn’t enough. 

Companies need the right mindset about risk, experimentation, and how creativity connects to the market.

Check out these three observations that will shape how leaders think about growth in 2025 and beyond.

1. Speed as a Competitive Advantage

Smaller companies move in hours and days. 

Mid-sized companies move in weeks and months. 

Large companies move in quarters and years.

That difference is the gap. 

If you’re leading a startup or growth-stage business, the ability to move faster is your built-in advantage.

The key is asking: How can we get this done faster without breaking things? 

The companies that find and maintain the right momentum win.

2. The Innovator’s Dilemma

In large organizations, the cost of failure is high. 

A new initiative can take six months to build, only for it to flop after the first test.

However, in smaller, faster companies, that same six months can hold 50 experiments.

Most of them fail quickly, but one will work—and that one will fuel growth.

That’s the innovator’s dilemma: the bigger you are, the harder it is to innovate. 

Which is why leaders of smaller, fast-moving companies must create cultures where testing—and even failing—is encouraged, as long as it moves the business closer to a breakthrough.

3. Capitalists vs. Artists

Artists create for beauty and meaning. Capitalists create for the market.

The best leaders find the overlap. 

They apply creativity to make something people actually want.

Steve Jobs is a perfect example. In any other life, he might have been a starving artist. 

But he paired creativity with a sharp sense of what the market wanted, and then he built products that reshaped entire industries.

Leaders who master both perspectives—artistry and market awareness—are the ones who last.

The Takeaway

  • Use speed as your advantage.

  • Encourage experimentation, even when it fails.

  • Balance creativity with market demand.

That combination is what turns a good idea into a movement.