Ep36: Rajeev Gupta – Missed Opportunity to Invest in Jack Ma

Rajeev Gupta has an immense 20-years experience investing and building technology companies.  He worked for almost a decade at Goldman Sachs in Hong Kong, Singapore and New York focusing on listed and unlisted technology companies.  He then moved at Tribeca & Merricks Capital where he ran global technology funds and eventually built his own 25-person technology start-up company, Geckolife.  He is also currently a Partner at an investment company, Alium Capital.  Rajeev graduated from the University of Sydney with an Honours degree in Finance & Econometrics. On the other hand, Rajeev spends his personal time with his four kids and is fond of traveling, watching tv and skiing.

In this episode, get to know Rajeev as he recounts why he considers meeting Jack Ma in 1998 his worst investment ever and his valuable realizations in it.  Listen and learn from this expert as he will tell you more why you should be investing in technology now. Hear this and more in this another great story of loss to keep you winning.


As an investor, you must be able to detect tenacity.

Rajeev Gupta


Topics Covered:

02:55 – Rajeev explains why he loves to meet 8-10 companies every day and what excites him to do that

03:49 – He shares how he ended up with his worst investment and the story behind it

05:04 – Telling what the key differentiator is in investing

05:55 – He reveals his 3 worst investments and his realizations on it

07:31 – Defining what efficient frontier is

08:21 – Why not having conviction is a very weak way of investing

10:14 – One important actionable advice in investing

11:43 – Andrew sums up his opinions on the topic

13:42 – Andrew narrates his personal story about tenacity and what he learned on it

17:02 – Wise parting words from Rajeev – “If you come across anything in technology that sounds dumb today, it can be almost guaranteed. You look back in 10 years and say, why did I not support it? So, if you think something’s done, don’t be dumb.”


Main Takeaways:

Lesson 1: As an investor, you must be able to detect tenacity.Rajeev Gupta

Lesson 2: “So my worst investment has been a) not having conviction, b) not putting my balls on the line and c) not writing themes that you hear about, but do nothing about through that journey.”– Rajeev Gupta

Lesson 3: “Conviction to me is the most important part of investing both positively and negatively.  My worst investment is not putting more money to work in what was looking at me in the face.”– Rajeev Gupta

Lesson 4: “I think the best way to invest is have a big chunk of what you do and I’d say 50 percent or maybe slightly more in super risky stuff which will give you at an exorbitantly high return.”– Rajeev Gupta

Lesson 5: “If you focus on the risky stuff, the risky investments, yes, they can go to zero. But if you do your work, you have your conviction. You know that the magic you’re talking to companies will make an enormous return.” – Rajeev Gupta

Lesson 6: “If you’ve done the work and you believe in the thematic, I think you go hard and supersize positions as early as you can. ”– Rajeev Gupta

Lesson 7: “The first is a warning, warning, warning to the listeners.  Remember what he said was you’ve got to have your thematic right, and you’ve got to do your homework. Rajeev is not saying, just have a conviction.”– Andrew Stotz

Lesson 8: “Build your story, build your theme, do your homework.  But also, never be afraid to try to find someone that disagrees with your conviction and get their input.”– Andrew Stotz

Lesson 9: “If you can spot tenacity in a good, you know, and find a good person with a good idea, then you’ve probably got something you should back for long, long time.”– Andrew Stotz

Lesson 10: “There are only two times that you’ll have to worry about conflicts in partnerships – when you’re losing money and when you’re making money. Otherwise, you don’t have to worry.”– Andrew Stotz

Lesson 11: “Numbers can sometimes be very deceptive. I think numbers should be seen as something that’s supportive. You cannot ever trade person, individual, thematic and tenacity.”– Rajeev Gupta




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About the author, Andrew

Dr. Andrew Stotz, CFA is the CEO of A. Stotz Investment Research, a company that provides institutional and high net worth investors with ready-to-invest stock portfolios that aim to beat the benchmark through superior stock selection.

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