
Damn, what a situation. Poor guy. Hopefully he's connected with some experienced traders as well. This kind of story is as old as time. There are a lot of really helpful tools and perspectives out there.
https://www.youtube.com/watch?v=JVvwCkB-JLE
https://www.youtube.com/watch?v=qTV7afiYE6A
There's also a fantastic story about someone navigating an even more scary scenario in the first chapter of Schwager's _Stock Market Wizards_.
Also http://www.trendfollowing.com/
Trading is very hard. Markets are efficient at a first approximation and where they are not efficient, simple arbitrages do not exist. You are up against smart, well capitalized people. Once you find an edge your irrational brain cuts in.
Books: "Investing by the numbers" by Jarrod Wilcox. "Trend Following" by Covel. "The only three questions that count" by Fisher. And of course the "[Stock]Market Wizards" books. Typically the top traders seem to have read a couple of hundred books on the topic and have done thousands of hours of research.
Your assumption that you will lose at first it probably right. But that's better than winning at first, which is likely to falsely convince you that you're a genius.
Beware the following which can look like skill for a while. 1. Randomness (temporary luck) 2. Excessive Leverage (-> gambler's ruin) 3. Selling insurance without realizing it eg selling out of the money options.
In this thread I've seen 'day trade', 'don't day trade', 'index funds' , 'don't do index funds'. Realise that all this advice is contrary, and only applicable to the specific people providing it. What matters is finding something compatible with your belief system, not twisting your mind to try and accept somebody else's belief system. Because when the pain and stress arrive, if you're not fully aligned with your strategy, then you're going to make the wrong choice.
Once you've decided you're going to put some effort in, then you need to work out a strategy that aligns with your personality. This needs to evaluate things like:
- your risk tolerance
- your expectations of returns
- your starting capital
- your analytical skills
Everyone is different, and the only people who succeed are ones who find an approach that works for their personality, and then take the time to get rid of their mistakes.
As for books, here's what I recommend:
- Intelligent Investor by Ben Graham - the take away in this book is the 'margin of safety' concept
- Trade your way to Financial Freedom by Dr Van Tharp - the take away in this book is that active management by position sizing and risk setting dictates more of your return than your actual strategy.
- Market Wizards, The New Market Wizards and the Stock Market Wizards, all by Jack Schwager. These books are all a series of interviews with top traders in commodities, currencies, funds, stocks and probably something I've forgotten. By understanding how an incredibly diverse set of traders have made astounding returns in the same markets should make you realise that there is no one approach that works, there are only approaches that work for specific people.
Good luck, and pray your first trade is a failure, not a success. Because you need to learn the pain of loss and how to minimise it before you taste the sweetness of profit.
I recommend basically reading books by:
Peter Lynch, Phil Fischer, and then chapters 8 and 20 of the Intelligent Investor. The book, Applied Value Investing, is also a pretty good place to start that actually does a lot of things well, combining both theory with practical case studies. -Reading the Buffett Partnership letters (not the Berkshire letters) is very helpful for someone managing small sums of capital, say below $10M
In addition, you need to read and learn about financial accounting and valuation. John Tracy's How to Read a Financial Report is a good starter... for valuation Aswath Damodaran has a pretty good book that can be combined with McKinsey's book on the subject. Beyond that, some more advanced accounting books, especially forensic stuff is great to know. Financial Shenanigans and Creative Cash Flow Reporting are where I'd start with that.
To be really good you also need to read quite a bit about psychology/mental models. Look for speeches/lectures by Charlie Munger. Books like Stock Market Wizards/anything that contains a ton of interviews with investors are also great. Reminisces of a Stock Operator is pretty good for giving you an account of the ups and downs that come with investing -- the guy the book is based off of blew his brains out. Studying financial history is also a must, especially with learning about prior bubbles.
Finally, you just have to commit to reading a whole lot, every day, and becoming a learning machine.