Frankly, I have some reservations regarding "speculators" as Chief Executive Officers.
I have two data points.
The company I used to work for spun off a major subsidiary. Buried in the fine-print was a tiny bit of verbiage that guaranteed the mother company would re-absorb the unionized employees and their legacy costs (medical, pension) if the spin-off declared Chapter 11 within five years. The mother company considered the risk to be non-existent because of the huge number of highly favorable supply contracts that the mother company had let to the subsidiary.
The former subsidiary hired a hedge fund manager as a CEO. Four-point-five years into the spin-off he preemptively filed for Chapter 11. The reason given in the filing was that they would not be able to make payroll (and cover legacy costs) at some point in the future if they stopped winning contracts. Duh!
A short time later, the mother company also filed for reorganization. There were two main causes. One was the economic slowdown of 2007-2009. The second cause was the torpedo below the water-line of the legacy costs associated with a 70% increase in the rolls of the unionized workforce.
As a personal note, two of my brothers-in-law worked for the former subsidiary as managers. One of them was on the verge of retiring after working for forty-five years. They lost their entire pension. They got NOTHING.
The CEO was amply rewarded for his prescience in proactively filing Chapter 11 in order to trigger that clause. In some circles he is a hero.
Several year later, after reorganizing, the company I worked for hired a hedge fund manager as a CEO. My boss dressed me down for telling him that something could not be done. He had just attended a video "cheerleading" meeting where the CEO had berated the entire chain-of-command for fear-of-failure. He told them, "I never want you to tell me something cannot be done. I want you to come back and tell my you tried but failed."
There are three scenarios where this makes sense. One is suicide missions. One is Design-of-Experiment where very small and firewalled experiments are run. The other is when the speculator can simply walk away from an investment-gone-bad.
I was directed to fail. I did. From my perspective it felt like a suicide mission. From the CEO's perspective, it was a logical extension of his history of being able to divest out of collapsing positions with no penalty. Early abandonment is a winning strategy for a speculator. There are many other investments out there. A more orderly and structured approach is appropriate for CEOs.
Trump
I am leery of guys like Trump. How many organizations has he taken into bankruptcy?
My coffee drinking friends suggest that the US is bankrupt. They think that Trump is exactly the guy we need. He has been there and done that.
My concern is that he will be like the CEO of the subsidiary, that he will roll over when it most benefits himself rather than battling to the bitter end. There is no dishonor in losing because you sent your last bit of ordinance down range. The dishonor is when you refuse to yank the lanyard because you are on the take.
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