It’s maintaining the mindset of an entrepreneur.
In its early days, a new venture makes its own energy. Every entrepreneur can tell you startup tales: a band of enthusiastic innovators, setting out on this great adventure. Who cares if workspace is small and the food is terrible and the hours are constant. It is exciting. Adventure always is.

When the new business evolves into a true, steady business, that sense of adventure can fade. Now, that same group, joined by many more, is not really on an adventure. They are a group of people who come to work every day. It’s not an adventure any more; it’s a job.
Maintaining the Entrepreneur Mindset
That perhaps is the biggest danger to any business – mine or anyone’s.
How can you keep the entrepreneurial mindset even when the early days are past?
  • Manage for it: At Rakuten we created tools that encourage entrepreneurial behavior. We want all employees to deliver value to the company. This can be done in many ways: identifying new merchants and categories for Rakuten Ichiba; finding new technologies or companies we can invest in; or proposing ways the company can be more efficient, even by changing light bulbs to save on energy costs. So our assessments look closely at results. People who are not creating real value for the company may not have a future here.
  • Talk about it: I talk about getting “back to venture” all the time. It’s the subject of my weekly address to the company. It comes up in meetings. It’s a topic of my speeches. I stop employees when walking through the halls or during lunch and ask them what they’re doing and what they’re seeing that’s new. How can we innovate? How can we maintain the startup feel at Rakuten? It’s amazing how employees are unafraid to share their ideas.
The greatest challenge of being an entrepreneur is staying an entrepreneur – even when your company gets big. It’s the challenge facing us all. By making entrepreneurship a part of everyday workplace conversation, you’ll never lose the mindset.