My windscreen wipers on my car recently stopped working. Being the lazy chump that I am I did not bother to repair them for a few days, and when I eventually had time I was unable to fix the problem myself. I proceeded to drive to work the next morning, but upon finishing it was raining: I was stranded.
The first point to make is never be stubborn or lazy: it never works out in the long run. Anyway, the long and the short of it is that I got the car to a garage, and the next day was informed the cost of repairing a wiper was £260 !! (~$400). To put that into perspective, about 1/8th of the value of the car! Now I did not really have a choice, and have since had the car repaired. So where does this all fit in?

When I invest money I am fully aware of the risks associated with the specific investment, such that if I lose it is my own fault. In domaining, my successes have significantly outgrown my failures. In the stock market, my hope is likewise. In real life finance however, I seem to have significantly more ridiculous outgoings/losses such as the above relative to my income.
Were I to have lost that £260 on a domain, or on the stock market, then fine. On a windscreen break that was not even my fault, not fine!
Now I do not intend to get into the psychology of losing. . . but this showed me that having money hanging around doesn’t get you anywhere. Every so often you get completely random outgoings, and thus your net money can not, and will not go up if you simply leave it. For that, you have to take a proactive approach and invest… invest hard.

Being a seasoned domain investor I have recently been put into a position whereby I have had to weigh up my financial position, and investment opportunities.

I have a certain, significant amount of cash sitting in my paypal account. My choices are essentially invest it in domains, or withdraw it to my bank account.

Domains
In the current climate the value of domains has dropped quite significantly. What is more, they are significantly less liquid than they previously were. Finally most people with the best domains, simply are not selling.
I have had these funds in my account for upwards of 2 months, and they have only slowly been decreasing. I would like to have a few great opportunities present themselves such that I can have clearly defined investment positions.
This feeling is to such an extent that I nearly put all my money into a great domain, that was slightly overpriced, and completely un-liquid… The only reason I didn’t is because such a domain is only worthwhile should you have the time to develop and market it to MAKE it worth the cost.

Every so often I buy great domains at great prices, from various non-domainers who I contact via email. These are the kind of domains I want: they are generally cheaper, and of better quality than the names being traded between ‘domainers’.
The problem is there are not many of these left, and they are extremely hard to find. Perhaps I will find another few great deals, but is it worth simply holding my cash online and waiting, or would it be best invested elsewhere?

Stocks
The stock market is another investment opportunity I have been seriously considering. The common statement with the stock market is don’t invest more than you can afford to lose. I could invest a few thousand pounds, and I could lose it (although I’d prefer not too..)
The banking sector worldwide is in turmoil, but I feel bank shares could be a great money making opportunity such that I may consider investment in HSBC, or RBS. These are extremely risky, but potentially seriously rewarding opportunities. It is perfectly viable to double your money in the long run, but again you could simply lose it.
I have also compiled a list of shares that seem interesting to me, as potentially profitable companies. I will research them more, and perhaps I will make some investments as opposed to punts

Being new to the stock market, I have very little idea as to its workings. I have done a lot of reading, and research. One great book being ‘The Naked Trader’. I intend to use the prophecies contained within to aid me in my first stock market investments.
I hope it goes well, and that I make significant gains. Sadly success is not a certainty.

When I started in the domain business, I was naive, and down-right idiotic. I have come a long way, and today have what I believe is an amazing portfolio. This is in a maximum of 3 years..
I thus feel success in the stock market is perfectly viable for me if I take my time, and do my research.

The question is do I maintain my domain holdings in the hope their value recovers, and invest my current free funds in the stock market? Do I sell my un-liquid assets at reduced prices to fund a larger investment in the stock market? or Should I maintain my position, continue looking for great domains and forget the stock market altogether?

Cheers