I have been mentoring a young man who aspires to own a business and be an 'entrepreneur' like many of his peers. I asked him once, 'What business would you like to create?' He said, 'Something online or get into property development. ' 

When I asked him why, he said he wanted to be rich, have financial freedom, and work for himself. These are now 'canned responses', especially from younger Millennials and Gen Z. 

Maybe it's the glut of social media influencers out there regurgitating this message supported by the 'algorithm' and mixed with some post-lockdown trauma yet to be defined.🤷🏾‍♂️ Whether it's content creating, selling on Amazon, building a property empire with no money down or trading dog coins.....it's clear to me that many people (young & old) are looking for a 'hack' or shortcut to a fortune. I suspect all of this is due to people feeling left behind (cost of living crisis) and without a clear path to get ahead. 

His dream is a noble goal and one that I can get behind. I am just not sure it was 100% authentic to him (more on this in the next post) - I then thought in a moment of self-doubt, 'What have I been doing working all these years for someone else' if being an entrepreneur is the only way to succeed? 

Searching for some cope online - I found this article from 2019: 

"the average age of founders of the most successful tech startups is 45" - Phew, I have time.

This interaction with my mentee got me thinking about one of the original WeWork values, 'Be Entrepreneurial':

"We are creators, leaders, and self-starters. We try new things, we challenge convention, and we’re not afraid to fail."

Thinking through these attributes and my experience, I returned to our A.I lord Google for a technical definition: 


1. characterised by the taking of financial risks in the hope of profit; enterprising

So, put the money up, take the risk and make a profit. This part of the definition sounds quite formulaic, albeit difficult to do. However, I think the key attribute to success is being enterprising. 

1. having or showing initiative and resourcefulness. 

I think back to when Roni Bahar (WeWork's Development Director, 2013-15) said to me: 

"WeWork is like a corporation with many entrepreneurs running small operations from within." 

Upon reflection, I've realised what that comment meant in practice. The company was entrepreneurial (by definition) and filled with employees who didn't take the financial risk but were extremely 'enterprising'. In my view, this was the oil for the engine that drove the success (what a wild ride). I witnessed that the 'culture' of an organisation is key, especially in the early days. 

Coming back to my mentee for a moment. My advice to him was twofold.
1) to be more specific about the business he wanted to create and 2) become obsessive about it daily and be resourceful. 

I shared with him that for 20 years, I've obsessed over a specific branch of design - 'Interiors' and if he can focus on developing the 'enterprising' attribute to go along with specificity, it will hopefully lead him to become an entrepreneur. 

Serious cope - Maybe it's advice for me.😅
Thanks for reading.


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