Dwayne Holness

Thoughts

Thinking out loud.

01

Thought Leadership

19 May 2026 · 4 min read

The Secret to Winning Is Knowing How to Lose

Most people are never told that the moment you decide to play seriously, you sign up for a longer relationship with loss than victory. Here is how to lose well, and why it is the only path to winning anything worth winning.

02

Entrepreneurship

2 May 2026, 1:08pm · 4 min read

How to Kill a Snake

In 2010, my older cousin gifted me a $3,000 camera, then came back to take it. What jealousy taught me about altitude, family, and the favour on your life.

03

Entrepreneurship

29 April 2026, 9:30am · 4 min read

Busy But Broke: The Real Path to Runway

Most entrepreneurs spend years busy but broke. Here's the three-stage arc that actually moves you from rolling a ball up a hill to building real runway, and why three months is the line between operator and owner.

04

Entrepreneurship

10 April 2026, 9:00 AM · 6 min read

The 9-to-5 is the
Riskiest Bet You Can Make

Most people think entrepreneurship is reckless. But trading your one life for a paycheque you didn't negotiate, on a schedule you didn't set, for a vision you didn't write, that's the real gamble.

05

Thought Leadership

5 April 2026, 10:00 AM · 5 min read

Be Guided by Beauty.
Collaborate with the Best.

Two principles that sound simple and are rarely practiced: work with the best people you can find, and let the standard of doing it right be the aesthetic that guides everything you build.