The Courage it Takes to be an Entrepreneur

Life as a an entrepreneur can be tough, its not for everyone. There is no school that prepares you for the realities of entrepreneurship. You can read textbooks, join workshops, watch YouTube videos, but until you've given it a try first hand, your appreciation of what it takes will always be naive. Management skills don't make an entrepreneur great. Neither does access to capital or innovative thinking. There is something much more simple that differentiates the individuals that thrive, from those that struggle.

That one thing and one thing alone that every great entrepreneurs absolutely must possess is COURAGE


Courage is very rare in our world.  Numerous surveys of the population at large have shown that, above everything else, most people value security. Most people don't know that I live my entire life by a set of values that drive decisions, purpose and legacy. Values I took from Bushido, literally "military scholar road", is a Japanese word for the way of the samurai life, loosely analogous to the concept of chivalry. At the naive age of seventeen I chose to have my six values hand a calligrapher put on rice paper and framed. Then one by one, when I reach a meaningful milestone in my life I have them tattooed on my body. Value number one is COURAGE. Anyone that has worked with me over the past fifteen years has their own story or can relate to the courage I brought to everyday.

Most people will tolerate just about anything--a bad marriage, an intrusive government, a horrible boss, a job that they hate--if only that thing can make them feel more secure.

Throughout the ages, people have searched for the precise alchemy of ingredients that constitute great leadership. In measured proportions, great leaders are said to demonstrate bold but reasoned judgment, spirited but calculated risk-taking and an assertive but reflective disposition. Complicating the matter are the expectations and needs of those being led. Followers want leaders who make decisions decisively but inclusively, interpret situations with rational and emotional intelligence and exude confidence and humility.

By no means am I advocating I'm a great leader, or destined to change the world. This is merely an illustration of a value and trait I am immensely grateful to possess. Contrary to popular belief, courage is a teachable and learnable skill, and nearly everyone has the capacity to be courageous. Moreover, nearly all courageous acts represent one or more of three types of courage:

  • TRY Courage: The courage of initiative and action— making first attempts, pursuing pioneering efforts and stepping up to the plate
  • TRUST Courage: The courage of confidence in others— letting go of the need to control situations or outcomes, having faith in people and being open to direction and change
  • TELL Courage: The courage of voice— raising difficult issues, providing tough feedback and sharing unpopular opinions
  • Courage is one of those traits that is hugely influenced by the nurture from your experiences, community and spaces. So its given me an immense sense of pride to watch Hub Singapore grow the courage of Singapore's developing entrepreneurial community. Making it an ideal theme for the HUB's 2nd birthday. Over the past two years the space and community have grown into a pivotal part of entrepreneurship in the region. What I now refer to as 'family' help each other grow and develop ideas and people around the central theme of courage.

  • It takes courage to forego the predictability of a corporate job.
  • It takes courage to sacrifice your nest egg to your startup.
  • It takes courage to take the risk of failure.
  • It takes courage to make your dreams into reality.
  • And it takes courage--lots of it--to hand over the reins when your startup grows beyond your ability to manage it.
  • Here is to HUB Singapore on their second birthday, and the successful journey of build the regions courage.