My understanding is at this level it's about personal connections and grooming an image. With that in mind, does it become harder to attract great executives on a go-forward basis for Uber?
A good analogy would be attracting candidates for coaching positions in sports.
If you're a team in a bad situation, you'll have to settle for candidates that don't have the experience usually required for the position, or people who've done it before who haven't had huge success.
Also most great execs are already in a great position - why would they step into a bad situation unless you gave them a higher title or more power?
Basically you get either a placeholder or an unknown quantity. The unknown quantity is just that. They might be awesome (everybody has to have had a first head coaching job) or completely overwhelmed.
If a losing team wants a winning coach, they will either have to settle for someone inexperienced, or pay up to get someone experienced in turnaround situations.
Same with companies, except with turnarounds the most substantial part of compensation is the company's stock. If the turnaround is successful, the executive will get wildly rich as the stock appreciates (and rightly so).
With Uber, the stock is greatly overvalued, which means anybody coming in is trying to turnaround the company, but only to maintain the current imaginary valuation. Where's the upside?
To your point, in the business world, if you've already gone through the turnaround experience, you're probably already very well compensated.
The one big thing that you can dangle in front of good candidates is a more powerful position or more responsibility. Hire a COO into a CEO position, or give a proven head coach power over personnel decisions. Other than that, there really isn't much of a carrot you can dangle. A move from a CEO of a successful company to a CEO of a failing company is a strictly negative move. EDIT: all other things being equal, of course. You could get a CEO of a small successful company to run a large failing company, but that'd be similar to getting a successful high school coach to run a college team.
The only case I can think of where execs jump around fairly quickly in "turnaround" situations are those who specialize in getting a company ready for a sale.
And you have a name and a position and a network and influence at your company.
Money is worth peanuts compared to that!
What's the risk of taking an hypothetical 50M from Uber, it's gonna be trying to fuck you over with ISOs and sexually harass you, whereas you can take 5M a year at your current company safely and with great success for the next decade.
Keeping a successful ship successful is hard work. There is nothing a distressed ship has to offer you.
If you were offered the job of President of Uber, say at the same salary you make now, would you take it?
I'm sure a lot of people would say yes.
Success or fail, you would now have "President of a multi-billion dollar company" on your resume.
The people who are qualified for the job or would be even considered in the first place are likely to be in one of two career trajectories at the moment: aiming upward to become the CEO of a major corporation or on a downward path and trying to maintain the power, respect, and lifestyle to which they have become accustomed. People in the former category would avoid Uber like the plague, so you are looking for someone in the latter group who is talented enough to catch a falling knife but somehow overlooked by companies making a similar search but not quite as desperate as Uber happens to be at the moment. Tough order to fill...