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  • Writer's pictureCreative Return


Tommy Humphreys at The Insider's Guide to Finance
Tommy Humphrey’s journey from web design to wealth, including his $17M exit, insights on entrepreneurship and mental health.

In this episode of The Insiders Guide to Finance, we have the pleasure of speaking with Tommy Humphreys, a true capital markets outsider turned insider. Tommy’s journey from a web design background to a prominent figure in the Canadian capital markets is inspiring. By fusing these two worlds together, Tommy founded, a leading stock market information service;  which, after a decade of growth culminated in a successful $17 million exit in 2022. 

“I think like-ability is one of the most common traits of the most successful people I know... I think in the capital markets, the salesmanship thing is really key.” — @tommyhump [0:19:10]

Beyond his entrepreneurial success, Tommy was an early investor in several successful public ventures, including Hive Blockchain, Lithium X Energy, Fiore Gold, and more. In our discussion, Tommy sheds light on crucial lessons learned about business, investing, and taking care of your mental health

Ego and envy are two character defects that are alive in all of us, right? And it's dangerous. Ego is not your amigo” — @tommyhump [25:00]

We discuss Tommy’s encounters with noteworthy figures in the industry, how he found his place in the media landscape in the early 2010s, and the challenges and rewards that come with acquiring wealth. Additionally, we learn about the origins of The Big Score newsletter and its significance in Tommy’s ongoing narrative.

What you think about is very powerful. And if your thoughts become obsessions you can make things come to reality that are both positive and negative for you. — Be very careful what you think about.” — @tommyhump [25:00]

To hear all of Tommy's insights on investment, capital markets, and entrepreneurship, be sure to tune in!


  • Tommy’s background in web design and how he entered the investment and trading sector.

  • How he successfully built and (to his surprise) exited CEO.CA.

  • Tommy’s experience of growing tired as an entrepreneur.

  • An overview of the media landscape and bank coverage in the 2010s.

  • How he addressed the vacuum in quality content during the economic downturn in the 2010s.

  • Standout lessons from Tommy’s interviews with key industry figures.

  • Reckoning with feelings of envy and caring for your mental health.

  • Unpacking what motivates high earners.

  • How wealth can reveal who people really are, and the challenges that come with it.

  • The contents of Tommy’s new newsletter, The Big Score.

  • Insights on key figures in Howe Street trading culture.

  • How the Canadian venture capital market has changed over the past few decades.

  • Tommy’s insights into the Toronto Stock Exchange (TSX) and how it functions.

  • A rundown of the books and figures that have inspired Tommy.


For more information on our sponsor, please visit Olympia Trust Company

Please note that the information contained in this interview is not financial advice but for entertainment purposes. I am not a financial advisor and make no warranties or representations concerning the accuracy or suitability of the information contained in this interview. I recommend that any and all investment decisions be made with the advice of registered investment advisors.


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