Blind Optimism Fuels Greatness, Not Cynicism, According to Simon Squibb

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Simon Squibb

LinkedIn Author

On a mission to fix the education system & help 10 million people start a business for free

In a recent LinkedIn post, Simon Squibb discusses the often-underestimated power of optimism in achieving ambitious goals, contrasting it with the limitations imposed by cynicism. Squibb, an entrepreneur known for building significant businesses, argues that while cynics may possess intelligence, their inherent skepticism prevents them from reaching their full potential.

Squibb shares an anecdote from a brainstorming session with TikTok’s Zach King, who adheres to a strict “yes, and” rule for video creation. This principle, Squibb explains, is crucial for fostering an environment where innovative ideas can flourish without immediate dismissal.

“You can only say ‘yes, and.’ Not ‘that won’t work,’ or ‘we don’t have the budget’ Because that language kills great ideas, and with enough outside-the-box thinking, you can achieve anything.”

The Power of “Yes, And” in Innovation

Simon Squibb elaborates on how the “yes, and” approach actively combats the destructive nature of negative feedback. He posits that language directly influences ideation, and phrases that shut down possibilities are detrimental to creativity. According to Squibb, when practical limitations are temporarily suspended, creativity can expand exponentially, leading to the generation of truly groundbreaking ideas.

To cultivate this environment, Squibb mentions the implementation of a “creativity corner” in his office. This designated space is intended to be a safe haven where even the most unconventional or seemingly “stupid” ideas can be shared and met with support rather than criticism.

Building a Life on Illogical Ideas

Squibb provides personal examples to underscore his argument that embracing seemingly illogical optimism has been foundational to his success. He recounts moving to Hong Kong at 23 with no resources, eventually building and selling the largest agency in Asia to PwC.

“I moved to Hong Kong at 23 with no money, a job, or a place to stay. ( I then built the largest agency in Asia and sold it to PWC for more than I could ever need)”

Another example cited is the decision to start an agency with someone he had known for only a month, granting them a 50% stake. This partnership, Squibb notes, led to a successful marriage and shared wealth.

“I started an agency with someone I’d known for a month and gave her 50% (She is now my wife and we became rich together)”

He further illustrates this point with the purchase of a non-functional staircase for a significant sum, an investment that ultimately yielded substantial reach and impact.

“I bought a staircase for £25,000 that went nowhere (This helped us reach millions of people and helped thousands with their dreams)”

Optimism vs. Cynicism in Achievement

In conclusion, Simon Squibb asserts that while cynics might be the most intelligent individuals in a given room, their outlook prevents them from achieving the same level of success as optimists. He acknowledges that cynics can often identify valid reasons why something might fail.

However, Squibb argues that this critical perspective rarely leads to the construction of anything significant. In his view, it is often a form of “blind optimism” that provides the necessary impetus to build something truly great, challenging conventional wisdom and overcoming perceived obstacles.

📝 About This Content

This article is based on insights shared by Simon Squibb on LinkedIn.

📅 Originally posted on April 28, 2026 | View original post on LinkedIn →