I very recently had as a guest on my radio talk show (taeradio.com) one of the world’s foremost gurus on the subject of high tech entrepreneurism, Mr. Jason Fried.

Fried’s latest book, entitled REWORK, is currently ranked sixth among all business books by the New York Times and debuted at #2 on the Wall Street Journal’s exclusive list of “Best Hard Cover Business Books”.

Not bad for a first-time author.

Himself an entrepreneur (Fried is co-founder/owner of 37signals, a software development and products company), Fried dedicates a chapter in his book to the conundrum faced by so many successful entrepreneurs; a conundrum I’ll simply label: “Should I sell it, or should I continue to build it”?

Fried generally advises his readers to continue building; making these points:

• Will money alone truly make you happy? (In my opinion, it doesn’t and can’t)
• Are you sure that you like money more than you like running your business? (Again my opinion - you won’t) and my favorite,
• Good things (e.g., a business you love) don’t come around all that often --- don’t let your business be the one that got away. (I totally agree!)

To these points, let me add my own. Some of what I am going to now tell you might seem obvious, some might not. But I can assure you that all of it is documented personal history:

• About ten milliseconds after you sell; the parasites will come out of the woodwork. They want your money (and not you - which is probably what you think they want) and they will want as much of it as they can get.
• And since this is the first time you’ve ever had what I call “Big Money”, you are almost assuredly going to be very bad at protecting it.
• And, since procuring investor money is pretty much ALL that the parasites do, they are in turn quite likely to be very good at getting it from you. Remember, these are probably the same people who were very good at talking the professor into an “A” after they failed the test, and not the people who did all of the hard work, studying and preparing beforehand.

I personally invested in about a dozen companies in the three years after I cashed out a very successful business. While some of these folks were sincere and hardworking, nearly all of them picked up on my desire to “continue the high” that I got from creating a fast-moving, high tech company. Hell, they really didn’t have to be all that prescient - I practically gave them a road map to my heart by telling them that “I want(ed) to be involved” in their start-up; I wanted to help them make decisions and I wanted them to “use me”.

They sure picked up on that last one --- ask, and ye shall receive.

The minute my check passed to their bank account, I was history. I would bet that some of the companies I invested in had a ritualistic burning of my contact information!

And while all of this is going on, the likelihood is probably also pretty high that you will, and consequent with your sell-out, raise your own personal lifestyle. In fact, I know of cashed-out entrepreneurs who raise it to the point where they almost need another “score” just so they can stay “retired”.

And so I say to anyone who cashes in his or her company, “take a look” at what I call the “Five “C’s”: Cars, Clothes, Cribs, Cash and Chums. Here should be the essence of your analysis:

• First, the “Big Three” (cars, clothes, and cribs) – All of which are just losing ways to employ one’s cash. Ask yourself, did my “investment” increase by more than 25% in the three years après sale? (And yes, that’s correct - a house is, sadly, no longer a good investment.)

• Cash – Do you find yourself forever picking up the lunch and dinner tabs? Are you now “taking care of” questionable “friends and family’s” business and personal “financial problems”? (Problems that your friends, by the way, never even seemed to have before your sale.)

  Look, just because you now have money is no reason why you have to work hard at getting rid of it. It is perfectly acceptable to defer the meal tab to someone else - even to someone who might have lesser means than you. And if these people are your true friends (see below), then they will understand. If not, then maybe they weren’t really your true friends in the first place.

  Just keep on repeating to yourself, “I worked hard for these dollars - I’m on a first-name basis with each and every ONE of them - and so if someone else wants them, well then, maybe they should just go out and do what I did.”

• “Chums” (I know that this term went out with winning Pirate baseball, but hell, I’m old and I needed a “C”!) – Finally, and this is usually the one that delivers the “coup de grace”, you must ask yourself if perhaps you may have abandoned your lifelong and loyal friends to instead run with what I’ll call the Whirl People (and hey, there is no one in town whom I respect and like more than my good friend and fellow entrepreneur – Jack Tumpson. In fact, we started our magazines the same month).

  Look, it is a proven fact that you simply cannot keep up with these kinds of people - for one thing, they are the practiced possessors of the “Old Money” - which means that: a.) they have plenty and endless supplies of that old money, and, b.) they have been coached since they were old enough to differentiate a Double Sawbuck from a C-Note, how to hang on to those “Old” dollars.

  Go ahead and try to get them to pay - I swear it will be your bucks, and not theirs, that disappear both the firstest and the fastest!

I have a word limit with this column or I would go on and on. But since I cannot, let me close my saying just one more thing and that is the fact that I have asked many, many entrepreneurs who have done one of the following three things whether or not they regretted their decisions:

• Sell the business
• IPO or ESOP the business
• Continue to have majority control and run the business

Since my survey was undocumented and informal, I guess that you might say that it lacks credibility. Except for one thing:

Each and every person I have ever surveyed said that they would prefer to just continue running their start-up - especially those who had somewhere along the way already traded “freedom for cash”.

So maybe CSN&Y had it right all along, eh?

(This column to be read to the tune, “Find the cost of Freedom”, by Crosby, Stills, Nash, and Young – circa 1970.)