This was my response to the above question on Quora
The only way to make money as an investor in startups is to have a portfolio of investments. If you invest only in one and hope that it works out well, well, the chance are rather slim.
Startups by design are experiments … a set of assumptions that are being tested in the market by someone who has the conviction about a concept. Sometimes the experiment works, often it does not. But that is the only way new ventures get created… by testing many ideas.
So, if you want to make money by being an investor in startups, think of investing (or better co-investing with other angel investors) in 15–20 startups over a 3–4 year period. Some of the companies you invest in will shut down. Some will struggle to keep afloat, but will amble along. Some will become good businesses for the entrepreneur, but will not give any return (exit) to investors. Only a very few of these investments will give multi-bagger returns making up for the losses incurred in those who did not do well in the market.
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Author: Prajakt Raut
Prajakt Raut is the founder of Applyifi.com, and author of the book for startups - ‘Starting Up & Fund Raising’
Prajakt personal goal in life is to encourage and assist a 100,000 people to become entrepreneurs.
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Prajakt is the founder of Applyifi - an online platform that provides startups a 36-point scorecard and assessment report on the venture's investment readiness [www.applyifi.com], and helps them improve their odds of getting funded.
Prajakt is also the founding partner of The Growth Labs, a platform where growth-stage companies get sharp, incisive advice from senior professionals and experienced entrepreneurs. [www.thegrowthlabs.in]
Before starting Applyifi, Prajakt was the head of operations at IAN, founding member of a leading incubator, and the Asia-Director for TiE (2004 - 2007). Previously Prajakt had co-founded Orange Cross, a healthcare services company, and was part of the founding team member of Idealake Technologies. While in college Prajakt had founded a printing business and has spent over 10 years working in leading advertising agencies.
Prajakt’s book, ‘Starting Up & Fund Raising’, helps startups understand an investor’s perspective, and helps them improve their odds of getting funded. The book also helps entrepreneurs understand the building blocks of a business.
View all posts by Prajakt Raut
thehubforstartups.com 
YES A GAMBLE WITH YOUR MARBLES I SUPPOSE……AND BOTH THE INVESTOR AND THE ENTREPRENEUR PLAY THE GAME WITH THE SAME OBJECTIVE TO EXIT FAST WITH MAX ROI!