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224. Inside the Mind of a Serial Entrepreneur with Tash Courtenay-Smith


I love picking my clients’ or colleagues’ brains when they’re experiencing massive breakthroughs in their lives or businesses, and my guest this week isn’t just having a breakthrough. She’s constantly living in it.


Tash Courtenay-Smith is a UK entrepreneur who went from being a journalist at the Daily Mail to starting her own journalism and media business at 27 years old, which she then sold in 2014. Since then, she has started several other businesses, sold two more, built a seven-figure marketing agency, runs a couple of retail stores on Notting Hill’s iconic Portobello Road, and runs a free program called Biz Kids where she teaches entrepreneurship to kids.


Join us on this episode to bear witness to the way a serial entrepreneur like Tash thinks about and approaches business. We’re exploring what her entrepreneurial journey has looked like so far and the keys to her success, how to make decisions quickly, and Tash’s insights on what it looks like to come up with new ideas, evolve, and put them out there in the world. 


The 2025 group of The Masterful CEO $chool is now open for enrollment! The next live event will be in Costa Rica in January 2025, and you can enroll by clicking here!


What You’ll Learn from this Episode:

  • Behind the scenes on Tash’s entrepreneurial journey.

  • Tash’s thoughts on the secret to getting any business off the ground.

  • What has allowed Tash to be passionate yet unattached to specific outcomes in her businesses.

  • Why she doesn’t think of closing one of her businesses as a failure.

  • How to get more exposure to different ends of the business world.

  • Tash’s tips for staying an excited serial entrepreneur.



Listen to the Full Episode:


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🌟Catch up with Coach Jess:



Full Episode Transcript:




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