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     What do you want to hear from the My Worst Investment Ever Podcast? Tell us here! Resources:  My Worst Investment Ever Book myworstinvestmentever.com   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 exorbitantly high return.”– Rajeev Gupta Lesson 5: “If you focus on the risky stuff, the risky investments, yes, they can