So, I've never worked in a startup, but I've done my time in a large conglomerate. While I was there, I noticed a pattern that I believe translates fairly well:
Business teams make decisions that are based at least as much on the resources that are available to them as on what makes business sense. A really well-funded software team will buy itself a bunch of expensive computers, and proceed to write a to-do list app that assumes it's running on high-end kit. A really well-funded marketing team will throw huge blowout after-hours parties at trade shows even though the target audience is people who go to bed at 8pm. All well-funded teams hire too many people too quickly, and then waste productivity on failing to do a good job of keeping everyone coordinated. The corollary to this is that the best-funded teams have a tendency to underperform. (Or at least that's the impression I get.)
My sense is that it's similar with individual companies: The best way to create a train wreck is to find a really promising up-and-coming startup, and help it become a well-capitalized up-and-coming startup.
Business teams make decisions that are based at least as much on the resources that are available to them as on what makes business sense. A really well-funded software team will buy itself a bunch of expensive computers, and proceed to write a to-do list app that assumes it's running on high-end kit. A really well-funded marketing team will throw huge blowout after-hours parties at trade shows even though the target audience is people who go to bed at 8pm. All well-funded teams hire too many people too quickly, and then waste productivity on failing to do a good job of keeping everyone coordinated. The corollary to this is that the best-funded teams have a tendency to underperform. (Or at least that's the impression I get.)
My sense is that it's similar with individual companies: The best way to create a train wreck is to find a really promising up-and-coming startup, and help it become a well-capitalized up-and-coming startup.