The man, who would only say that he had worked for "a search engine" and is "unemployed by choice," said "it kills me" for Congress not to allow of Bush tax cuts to expire, noting that he hopes "that will change."
After listening to Obama's response, the man also noted that has a lot of wealthy friends who feel the same way and would support a tax increase on themselves.
Obama said he appreciates the man's sentiment that "we're all in this together" and talked at length about the reason he and the unidentified man are successful -- because someone invested in their education.
"So often the tax debate gets framed as class warfare," he said. "Look, as I said at the outset, America's success is premised on individuals, entrepreneurs [who] get out there and are pursuing their dreams and making a whole lot of money in the process. As you just pointed out, we're successful becuase somebody invested in our education."
The income balance in the last few decades, Obama explained, has become overly tilted towards the rich while middle-class incomes have flat-lined. Meanwhile, taxes have declined during the last 15 years.
"And we are not talking about going too punitive rates that would somehow inhibit you from wanting to be part of a startup or work hard to be successful," he said. "We are talking about going back to the rates that existed as recently in the 1990's when, as I recall, Silicon Valley was doing pretty good. And well-to-do people were doing pretty well. And it turns out, in fact, during that period, the rich got richer. The middle-class expanded. People got out of poverty because everybody was doing well."
"So this is not an issue of do we somehow try to punish those who have done well. That is the last thing we want to do. It is a question of how can we afford to continue to make the investments that are going to propel america forward. If we don't improve our education system, for example, we will all fall behind. We will all fall behind. That is a fact. And the truth is that on every indicator -- from college graduation, math and science scores, we are slipping behind other developed countries."
Watch the video below.