Inside Steven Bartlett’s invite-only fireside chat for entrepreneurs in Singapore

The Botswana-born entrepreneur and The Diary of a CEO podcast host told Singapore founders why skills compound, stories magnetise, and quitting liberates.

On the morning of 19 September 2025, I walked into the Founder’s Playbook knowing this was private, invite-only, and the room was filled with Singapore’s most restless entrepreneurs, each of us curious about how Steven Bartlett would speak about building in today’s environment, where attention shifts faster than markets themselves.

As host of the popular podcast The Diary of the CEO, Steven is also an entrepreneur, investor, and the youngest-ever Dragon on Dragons’ Den.

When moderator Elston Sam asked him the first question—where he would start a business with zero dollars—Steven did not hesitate. He stripped the problem down to five buckets: knowledge, skills, resources, network, and reputation.

Then he delivered a line that landed like a hammer, knowing that knowledge and skills are the only two buckets that can never be emptied. In that moment, I felt the room collectively stop fidgeting because every founder there knew how often we chase the other three buckets at the expense of the first two.