Note: Ben Graham wrote about all these decades ago. (It doesn't make this article less true, etc. -- just if you're interested in these basic rules of investing, then read 'The Intelligent Investor'.)
I thought Ben Graham, and the Intelligent Investor, was the absolute antithesis of high risk Venture Capital.
From the introduction to that book:
"Our text is directed to investors as distinguished from speculators, and our first task will be to clarify and emphasize this now all but forgotten distinction. We may say at the outset that this is not a “how to make a million” book. "
and
" “An investment operation is one which, upon thorough analysis promises safety of principal and an adequate return. Operations not meeting these requirements are speculative.”"
Fred Wilson is in a very, very different space then Ban Graham was discussing in the Intelligent Investor.
They are both speculators, just different time horizon.
My epiphany came when a few years ago I had a conversation with a friend who is a brewmeister and restaurant manager for properties owned by his family's trust. (If you live on the Peninsula, you have probably had his beer.) His grandfather had set up a trust in order to pass his Monterey-area produce farm to his children, and the trust and farm are still going, and growing. My friend mentioned he was spending the weekend at a family retreat with some of his siblings and cousins that were the current trust management. The topic for the retreat was identifying which of "the cousins" (the pre-teen and teenage children of the next generation) were likely to be future manager-trustees, and which were likely to be passive trustees. The goal being to start identifying and grooming the next generation of management.
So my definition of investor: If you are managing the asset with the intention that someday your as-yet unborn grandchildren will be taking over and managing the asset, you are an investor. All else is speculation, just on various time horizons. An investor is never looking for liquidity, ever -- only speculators expect to turn an asset into cash in the foreseeable future.
How do you define liquidity? If there is no way to take your investment, and turn it into liquid cash in the form of a stock sale, or dividend, then what is the purpose of said entity? Sounds more like a foundation with some broader goal (societal, religious, environment, etc...) than a financial investment to me.
If sale of the asset is the only way your asset returns cash to you, then it is certainly speculation by my above definition. Have you not considered operating a business as an on-going entity producing profits on a regular basis? Or have you become so blinded by the VC model that you can't imagine doing anything other than selling your stock to the greater fool? I can assure you that my friend's brewery produces liquidity in the form of cash as well as libations. Well, the latter turns into the former, to be most precise.
It is striking that actual operating profits have become such an insignificant part of the asset valuation process that some people forget the existence thereof.
What purpose are profits if you don't liquidate them? Unless you are Scrooge McDuck and you just enjoy diving into vaults of moola. (not sure if I'm dating myself with that reference)