He wouldn't survive in Silicon Valley or the technology industry. He probably fits in more with Wall Street.
I guess you're right, his antiquated campaign strategy doesn't really fit in with the innovative culture. He's more an institutional type, maneuvering arcane rules and systems.
As to the OP--I'm absolutely positive Mitt would make over a million dollars within a few years. What keeps most people from making money is risk.. they assume they need to have a job from an employer and collect a paycheck, because rent is due, so they sell their time. At $8.45/hr, the amount of time you have to spend to make a living doesn't give you much time to do much else so you get stuck there.