The True Value of Support: Simon Squibb on Building Your ‘Winning Circle’

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Simon Squibb

LinkedIn Author

On a mission to help 10 million people start a business for free

In a recent LinkedIn post, Simon Squibb explores the critical importance of identifying and cherishing genuine support systems, particularly during challenging times. Squibb, an entrepreneur known for building and selling successful companies, shared a personal reflection on who truly matters in one’s journey to success.

He highlights how external validation and relationships can shift dramatically based on one’s circumstances, emphasizing that true loyalty is revealed when one has little to offer.

“The people who believed in me before I made it are the only ones I trust now.”

Squibb recounts his early experiences, including a period of homelessness at 15, where connections were scarce and often limited to fellow individuals facing similar hardships. This period, he suggests, laid the foundation for understanding the nature of genuine support.

The Test of Adversity

The entrepreneur details the skepticism he faced when launching his first business. According to Squibb, many dismissed his venture, advising him to pursue more conventional employment. This experience further solidified his belief that those who offer support amidst doubt are the most valuable.

As Simon Squibb notes, “The few who didn’t laugh and supported me. They’re still in my life today.” This underscores a core theme in his message: the enduring significance of early, unwavering backing.

The Shifting Tides of Success

Squibb contrasts his early struggles with the reception he received after selling his company. He observes a marked increase in attention and apparent camaraderie from individuals he had not previously encountered.

“When I sold my company, suddenly everyone wanted to be my friend. People I’d never met acted like we’d known each other for years.”

This phenomenon, in Squibb’s view, serves as a stark illustration of how success can attract superficial relationships, while true connection is forged in less glamorous times.

Defining Your Inner Circle

Central to Squibb’s message is the concept of a “circle” – a group of individuals who provide authentic encouragement and constructive feedback. He prompts readers to reflect on their own networks.

“Look around you. Who pushes you? Who believes in you? Who will tell you the truth, even when it’s hard?” Squibb asks, guiding his audience to assess the quality of their relationships.

According to Simon Squibb, these are the individuals who form the essential support system necessary for achieving significant goals. He argues that cultivating and maintaining this core group is not just beneficial, but fundamental to winning in both business and life.

“And the right circle is how you win.”

Squibb’s post serves as a powerful reminder for business leaders and aspiring entrepreneurs alike to recognize and nurture the relationships that offer genuine support, especially when facing adversity. The insights shared underscore a timeless principle: true allies are those who stand by you, not just when you’re succeeding, but when you have nothing.

📝 About This Content

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

📅 Originally posted on March 22, 2026 | View original post on LinkedIn →