1) Typical big-company guy fails to adapt to startup life. A year ago, Flexport's tech team was 400 people. That's minuscule compared to what Dave's used to at Amazon. He came in, insisted on a bunch of unnecessary hiring, bloated the tech team with deadwood, internal kingdoms and politics, and a "move slow and don't break anything" mentality. Founder got fed up and showed him the door, though presumably they were gracious enough to let him hit his 1-year cliff
2) Almost-CEO-of-Amazon tries to build the next Amazon. Makes a bunch of wildly risky investments into random moonshots, because he doesn't want to settle for a single-digit-billion company. Founder is initially taken in by bigshot's vision. But after 1 year of minimal progress and changing market conditions, founder tells CEO to get back to basics and focus on freight logistics. CEO decides that's not sexy enough for him. Waits for his 1-year cliff, then resigns
Exited to hear more wild theories from others.