Experience — Rent It Or Buy It?

Big Red Car here. Been a little chilly and rainy in the ATX. Phooey!

Will be 70F today but cloudy. Tonight it gets into the 30’s.

So The Boss is talking to a couple of his brilliant CEOs and they get on the subject of “experience.”


Boss says experience figures into running a company, a startup, thusly:

Wisdom is the exercise of good judgement over a protracted period of time. Really good CEOs are wise.
Good judgment is the product of experience. It takes a long time to develop good judgment.
Useful experience is often the product of bad judgment.

If you wanted to be a wit you could say that wisdom is ultimately the product of the experience gained as a result of bad judgment. Therefore, run amok and exercise a lot of bad judgment chalking it up to tuition. No, that is not correct but it is interesting.

The Boss was a CEO for over 33 years and before that he was in the Army and ran platoons and companies commanding combat engineer troops in the US and overseas. The Boss has been garnering experience running things for longer than most startup CEOs have been alive. In the process you learn a few things.

The good things you write down, remember and duplicate because you like the outcomes.

The bad things you avoid because you don’t like the outcomes.

You learn continually but you have a base of knowledge — experience — to inform your learning so when you are confronted with something completely new, you can call upon your experience to inform you as to likely outcomes. You are flying on calibrated instruments, not flying blind.

And that is the value of experience.

Rent it or buy it?

Like almost anything in life or business, you can either rent or buy experience.

Take a second and see whether you agree with that.

You buy and pay full retail when you muddle through things and learn something in the process. The challenge is whether you’re going to learn the first time and whether you and the company are going to live through the experience. Sometimes you can’t afford to take the learning route.

You can seek counsel, ask a lot of questions, get some advice — classic “rent” behaviors — before you decide whether jumping off the Golden Gate Bridge is the best way to take a dip. An extreme example but one you can identify with because of its inherent absurdity.

Real world

Let’s talk about a real world example. One that almost every CEO will ultimately be challenged by.

Every year The Boss has several CEOs who are confronted with the necessity to modify their founder organizational structure. Sometimes they may have a co-founder who somehow plants the idea that the organization needs to either re-define roles or jettison him or anticipate he is going to jump. The bottom line is this — there is going to be a change at the co-founder level.

In the first few years of a startup this is so normal and to be expected as to be the base case rather than the exception.

The Boss has guided many CEOs and founders through this process.

Often it starts with co-founders reading documents, yelling at each other, writing shitty letters, getting lawyers involved. That is usually — no, always — the wrong approach.

How does The Boss know this? Because he has had decades of dealing with this actual real world experience. Co-founders getting divorced, co-founders being the wrong fit for the team, co-founders not paying attention to the business at hand because the company has been a little too successful too quickly, bad fit with skill sets and a lot more. Throw in a bit of “bad” behavior and the list of “why’s” gets very long.

What The Boss knows is this is always an emotional and difficult transition to make but it will get made if done correctly. Done poorly, nobody survives the experience.

The key is to understand it is a multi-step process — the classic five to seven touch process. If you let the lawyers get involved it will be messy, ugly and hateful. It will be expensive. It will leave scars. It will ruin reputations. It may wreck the business.

You have to regress back in time to when everything was sweetness and light and the promise of tomorrow was all optimism. From that point in time — a mental instant in time only — you can then reason with your friend making a tiny bit of progress each of the five to seven touches until finally all involved see the light at the same instant. Do not become impatient. Be thoughtful and jump halfway to the lettuce each touch.

Sometimes this may entail the CEO firing him or herself. Sometimes the process requires the lens through which the problem is being viewed to become a mirror. The Boss can see that coming long before you can because he has the experience.

The reason I use such a desperate example is because it does not have an obvious answer. It is not a calculus problem. It is not even really a rational problem. It is emotional.

Experience is the only way to be confident that chaos can be made back into order. Only The Boss’s actual experience in dealing with this kind of issue informs his optimism it will get done. Only his actual experience in dealing with startup CEOs and founders every year for the last three years informs him YOU can get through it with your sanity intact.

This particular example is only one example of the opportunity to rent v buy experience. It is not the most important but it is a common one.


CEO coaching is a way to “rent” experience but only if you are being coached by someone who actually possesses relevant and useful experience. If you are being coached by someone who has been a lawyer, an accountant, a psychologist or an author — you will get good legal, accounting, psychological and writing advice but you will not get good CEO advice.

Seek out someone who has been a CEO and who has walked in your moccasins because there is nothing like being a CEO to provide relevant experience. You cannot be a commercial fisherman and advise CEOs effectively. It is an entirely different kettle of fish.

If you need some advice or coaching, give The Boss a call or drop him an email. He’s got a little experience garnered in 33 years of CEOing and if he can’t help you, you will at least have a nice chat.

[email protected]

Tell him a Big Red Car sent you. [Pro tip: do not seek advice or unburden yourself to someone who can fire you. That is why The Boss only works directly with CEOs. They need a safe harbor.]

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car.  Be good to yourself, it’s hard being a CEO.

10 thoughts on “Experience — Rent It Or Buy It?

  1. Pingback: Situational Awareness - The Musings of the Big Red Car

  2. Jeff was my CEO coach at my last startup and he will be my CEO coach at my next one too. I’m a CEO who has raised venture funding, managed a board, fired a co-founder, hired rock stars, closed big deals and having the counsel of Jeff allowed me to do much more than if I had to go at it alone. Oh man the mistakes I would’ve made had it not been for Jeff.

  3. Trick is for the Ceo to know & recognize what they don’t know, first. Then they’ll be more open and self-conscious about getting help.
    Yes, mistakes are costly, but some people only learn that way.

    • .
      The smart CEO would not likely undertake his own legal work because he knows what he doesn’t know. Not too many CEOs will perform their own surgery should they need a mole removed.

      The really smart CEO would have a CEO coach, like Tiger Woods has a swing coach, from the beginning.

      Alas, knowing what we don’t know is the biggest challenge that many of us have.

      Stay well, Wm.


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