Apologies to anyone not a "Little Britain" fan- for the rest the title of this post can remain enigmatic!
Investors will often look for a new manager for their enterprises who has a clear track record of a rip-roaring success, preferably two, in closely aligned businesses. Such an individual brings experience, contacts and potentially some personal investment- all undoubted positives.
However, I was speaking to an early-stage investor who's looking for new management to join a portfolio company- he very eloquently put the case that he was looking for someone who'd been successful, but who had only made a little money from running another similar company. The argument goes that anyone who's made a great deal of cash before is never going to care enough about making a success out of the new company. He cited the example of a major radio station which had been a big hit and had been sold for a large 8 digit sum, but where the CEO had made a modest 6 digit sum- enough to be a little more comfortable than most, but still to be "on a mission" to prove to themselves they could get rich. This was held up as perhaps an ideal model.
I have some , sympathy with this view, even if it makes the search for new management even more challenging! I've been lucky enough to have met hundreds of entrepreneurs who've had every level of success from small trade-sale to major IPO- studying them has been fascinating. During this time I could certainly see examples of people who had made lots of money and, perhaps as a consequence, were rather comfortable. They can have a tendency to have mainly used the experience of being successful to learn how brilliant their opinions are on any business-related topic. I can certainly think of examples who seemed to me to be rather quick to reach extremely strongly argued opinions on minimal data.
As primarily a seed/first round investor, it's really important to me how follow-on investors view management in general and specifically, but I think for now I'll keep trying to look beyond the "proxy markers" to understand the individual themselves: they/we may just have to make do with the only Pirate Memory Game in the shop!