Self made rich folks may be tight, but they also usually know when to spend money, and if it's going to benefit them they won't be hesitant. We all know that directors sometimes buy shares at times when they know they are getting a bad deal because it makes people think they're good value.
If I had a vested interest in a company, I wouldn't hesitate to spend $2M on shares which were only worth $500k if it meant I was going to make money out of it, say, because I already had $10M worth of shares and it was going to boost the value of my existing portfolio, or because the company was paying me a wage of $1M per year and I hoped to keep it for a few years. I would gladly pay $2M to buy a cushy job with a $1M P/A salary for a few years.
There are plenty of ways to make money by spending money, and they aren't all direct.
I'm not commenting on what the directors have done here, I am pointing out that we can't just assume that they were getting good value because the buyers are wealthy and knew what they were doing and would be unwilling to lose money even if it meant making more money indirectly.
As someone else said, if they were so smart and so stingy, why did they buy them for more than they're worth now?
How much has Yaeger been given by MAD? How much would you spend on keeping up appearances if you were getting that sort of deal?
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