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Kevin O’Leary, aka Money Expert Mr. Wonderful and Shark Tank USA Investor on succeeding as an entrepreneur

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Giants, Ram Castillo here. This is episode #68! Today’s guest is a Canadian businessman, author and TV personality from Shark Tank USA. He co-founded the technology firm SoftKey – which was later acquired for more than $4 billion dollars. He has since launched O’Leary Funds (an investment fund company), O’Leary Fine Wines – and a best-selling book series on financial literacy which covers everything you need to know about making, saving, and growing money. He’s even stepped his foot into the world of politics (which we briefly talk about).


He has a current investment portfolio of 29 companies (possibly more from when I interviewed him 2 months ago to now). He first learnt about entrepreneurship at a young age after his step-father advised him to not become a full-time photographer – a story I won’t spoil as our guest delivers it so well. And now he is on a mission to educate the next generation of entrepreneurs to truly succeed.

Some of the topics we spoke about include:

  • The common mistakes he sees people aged 20 – 35 make with their money
  • His advice for going ‘all in’ professionally in your creative craft
  • The best and worst investments he has made
  • The three common attributes all successful pitches have on Shark Tank


So if you’re thinking about making a success out of your creative craft – or are looking for ways to grow your financial freedom through running a business, then this is for you – as we uncover what truly makes an entrepreneur successful.

I present to you … the brutally honest, relentless and generous … Kevin O’Leary!



More on Kevin can be found via the links below:

LinkedIn: Kevin O’Leary 

Kevin’s Facebook Page 

Twitter: @KevinOlearyTV 

Instagram: @KevinOlearyTV 

Cold Hard Truth on Family, Kids, and Money 

The Cold Hard Truth on Men, Women, and Money 

Subscribe to The Giant Thinkers Podcast on iTunes.



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About Ram Castillo


Ram is an award winning Design Director, Blogger, top ranking Podcaster, Speaker, Instructor and Author of two internationally acclaimed books 'How to get a job as a designer, guaranteed' and 'How to get a mentor as a designer, guaranteed'. He's based in Sydney, Australia and in 2012, started the blog which helps thousands of design students and graduates be employed. Ram has since been featured in Communication Arts, HOW magazine, Herman Miller, deFrost*, and Apple.

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