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From rags to riches?

Updated June 2026

By Jim Connolly | April 26, 2025

rags to riches, richard branson, self made, rags to riches story, 2025

Photo: Shutterstock 

This article gives you a behind the scenes look at those rags to riches stories we love. Plus, why they’re not always quite what they seem!

People love a good story. So much so, that facts are often changed in order to make the story more compelling.

Now, with some types of story, it’s unlikely to cause us any problems if the story we hear has been embellished. If that prince was a little less hunky in real life than in the story, it’s okay. Similarly, if the fish Bob caught wasn’t quite as big as he told us, that’s fine. But what if it’s a fact that Sir Richard Branson was actually born into a very, very rich and influential family?

Rags to riches… really?

Where we have a challenge, is when the stories we hear are intended to provide us with a business lesson, yet they have a key piece of information missing. Like the rags to riches stories, which contained no rags!

2 Types of business story

There are 2 types of story, which are commonly highlighted in business books, self improvement seminars and business blogs:

  1. The first kind of story is by far the most popular. It’s where we hear about the kid, who is born into poverty, yet goes from rags to riches. We love these stories, because many of us start off with nothing and aspire to make a success of our lives. As the son of penniless immigrants, I know I found these stories inspirational. They helped me believe anything was possible, even starting from zero.
  2. The second kind of story is also powerful and used as a warning. It’s the story of those wealthy business owners who self destruct.

However, there is a third type of story: a story which is seldom told, because it seems to lack the obvious impact of the other two.

Today, I’d like to salute a third group of people, whose stories don’t neatly fit into either of those 2 popular stereotypes. I’m talking about those who come from a super-wealthy or privileged background, but elect to use it as a springboard for something even greater.

Wealth to extreme wealth

Such is the demand for rags to riches stories that many riches to greater riches stories have been incorrectly retold, usually for the sake of emphasis.

I remember listening to the charismatic Easyjet founder, Stelios Haji-Ioannou being introduced on a radio program as ‘a poor kid who did good‘. Stelios politely interrupted the interviewer, to remind her that he was in fact, the son of an extremely wealthy shipping magnate. Stelios’ father gave him £30MILLION to start up his shipping business.

However, our desire to believe that hard working people like Stelios, must have come up the hard way, means these stories often mutate into one of rags to riches.

Sir Richard Branson is no rags to riches story. FAR from it!

Like Stelios, Sir Richard Branson’s success story is often referred to incorrectly, as rags to riches. Nothing could be further from the truth. Sir Richard was actually born into a wealthy, extremely influential family. He is the grandson of The Right Honourable Sir George Arthur Harwin Branson and the son of a leading UK barrister. Sir Richard’s story is one of wealth to extreme wealth. His achievements have been impressive, but we gain nothing in learning from his achievements, if we change the facts to make the story sound better.

Back in 2020, Sir Richard Branson’s family home was valued at over $5Million. Even that was a low, pandemic valuation. His parents bought the home in 1963 from a viscountess!

Sir Richard Branson childhood home
Sir Richard Branson’s childhood home

As we all know, many people born into that kind of wealth, choose to sit on their butt or self-destruct. Others spend their lives travelling the world spending their trust fund and then their inheritance, which is their prerogative. Few have done as Branson did (starting at age 16) and put their unearned assets to work for them, to grow multiple successful businesses, in many different industries worldwide. That should be a good enough story, without story tellers inventing a rags to riches beginning to the storyline.

Seth Godin is no rags to riches story

Seth Godin’s business career started with a superb business education at the best place possible. Seth’s late father, the highly-respected businessman William Godin, was the multi-millionaire owner of the largest business in its niche, in the whole USA. This saw Seth educated at the world famous Stanford Business School (see Stanford Graduate School for Business). For those who don’t know, Stanford is regarded by many as the finest business school in the world. Seth’s fellow Stanford students went on to become CEO’s of; Microsoft, eBay, Paypal, Trader Joe’s, Gap, Nike, Wells Fargo, Ford and countless other multinational corporations – plus at least 1 President of The United States. It’s a great place to get a world class business education and build a priceless network of super-influential, super-wealthy contacts.

Seth started his blog with a bang, thanks to super-influential contacts. For example, he wrote his first blog post, sitting next to Google’s co-founder, Sergey Brin: a fellow Stanford student. Seth’s story is regularly shared as one of rags to riches. The reality is very different, with Seth enjoying access to many of America’s most influential people and starting off with the support of his extremely wealthy family.

We learn nothing from incorrect information.

The true stories behind the success of people like Stelios, Sir Richard and Seth Godin, contain lessons we can learn from. My point, is that these stories do not need to be repackaged. Godin never needed to say he didn’t grow up in a rich family. He didn’t need to say he was so broke when he started his business that he couldn’t afford to eat healthy food. Branson didn’t need to say he came from humble beginnings. Their past doesn’t need to be retrofitted with poverty, to make their success more relevant. They stand up as they are.

This is really important

On a more serious note, by repackaging those stories, so they sound like rags to riches, the stories can become toxic.

New entrepreneurs often find themselves stuck, wondering why they are not seeing the kind of results that their inspirational, rags to riches role models did. They do this because they’re unaware that their role model may have started off with a world-class business education, the most influential contacts imaginable, the support of wealthy family and friends – or all of those assets.

For instance, it’s easier to sell a company for millions, when you have contacts who have budgets worth millions, which they need to invest.

In short: Be careful measuring your progress against anyone, but especially people you do not know. Rags to riches stories are often not what they seem.

IMPORTANT: If you want to make more sales, boost your profits and grow an amazing business, this will help you!

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Jim Connolly

Hi! I'm Jim Connolly and I help small business owners to increase sales, boost their profits and build amazing businesses. Read more here.

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