Does college matter? What happens when 50% of current jobs disappear? What does the future look like? These are the kinds of questions that people across the country need to be asking, but many don't even know where to start looking for the answers. To help fix that problem, Glenn has started to seek out strange bedfellows, many of whom are on the cutting edge of shaping the future. Jason Calacanis is an angel investor, entrepreneur, and blogger. He knows better than most what the future holds, and more importantly how to prepare.

Start listening to the interview at 1 hour 36min into today's podcast:

Below is a rush transcript of this interview

GLENN: This is crazy. I don't want to make this about politics. I want to make this about the future. Does college matter really? Or is it what -- how you learn to think and can you remain nimble enough in your thinking. I don't want someone who's gone to college and just learned how to think in a box. If you can go to college and learn to think outside of the box, great, but too many times college is making you just draw this straight line that everybody is going down. The world is not like that anymore. We have Jason Calacanis on. He is really the father of the blog. He started one of his web logs back in -- I don't know when. Sold it to AOL for $30 million in 2005, and he's an angel investor, has been investing in some of the greatest new technology around. And he also runs something call This week in start-ups. He's also one of the biggest entrepreneurial festivals that go on called Launch Festival, and Launch Festival happens in march. I am actually going to speak there in San Francisco. 10,000 entrepreneurs come to this, and think out of the box.

So I wanted to start with Jason there. Does college matter in the future to the extent of you would be concerned about someone who didn't finish college?

CALACANIS: Great question. Thanks for having me, Glenn. One of the major issues is the value proposition. $10,000 for four years or $20,000 or whatever you paid and I am a little younger than you, maybe $30,000 for four years for me, as a product of Fordham University.

One year salary. Maybe it seems like an okay thing it would for a couple of years, as you mature, but do go into debt, the equivalent of five year's salary, no, makes so sense. Then if you look at what truly matters in the world, to make it today, a combination of skills that are in demand, that go out of demand probably every five, ten, 15 years for some of these very specific skills, programming a specific computer language, using a specific peat of design software. What you need to have is grit, ethics, morality, leadership and resolve. When I look at entrepreneurs, people always ask me hey, how did you pick Thumbtack or Uber or some of these? I said I picked the individuals, not the ideas. If you look in someone's eyes and you can feel the passion and you can hear the logic and the decision-making and problem-solving they approach a space with, whatever the space happens to be -- for you, it would be media. For me, it would be angel investing -- their approach and resolve and problem-solving leadership ability, these are the things that matter. We have to re-optimize the school systems for those things and even if we do, the fact is, we are going to live in a world with much less employment and that's going to be a scary thing for everybody, independent of party mines, so I know this show gets a little political at times, but when you look at just the world and the flattening of the world, which means hey, everybody is going to trend towards the same arrow we wage at some point, and that is happening, and there's too many workers in the world, we are going to live in a negative job economy.

GLENN: What does that mean? I was just talking to my son last night. He's 10. We were talking about great cars. I said when you are my age, you will tell your kid, when they are your age now that you remember when your dad drove cars, and you drove a car, but you probably won't -- you may live in a world where you are not allowed to drive a car anymore. And as I was having this conversation, what I really wanted to say to him -- and by the way, it will be a scary world, because by the time you get out of college, if you go, 50% of all the jobs that are currently available, are going to be gone. I can say that, but I don't know what that really looks like. What does that mean, that we are going to be in a much more jobless world?

CALACANIS: You can see what it looks like. If you go to the Middle East, if you go to some of the underperforming European countries, referred to as the pigs, perch gal, Italy, Greece, Spain, and you see what happens when 20-something-year-old males hit 20, 30, 40% unemployment, it means riots in the street. And it could mean people hanging out, drinking coffee all day, getting a stipend from the government, looking for somebody to hate for their lot in life. And having a lack of purpose in life is dangerous. Those are the people who can get picked up presently easily by people who are using religion Todd bad things in the world and drugs and just whatever?

GLENN: So who is doing anything on that?

CALACANIS: Very interesting question. Now you are getting to the heart of it, which is hey, we have a lot of rich people in the world, right? Polarization of wealth is happening. What do the billionaires think? What do the people in true power think, the people running these huge companies? They are staying up late about it. I have had many after night thinking about this issue, and there are some creative solutions. I think we will work it out and we'll be in a beautiful world in the future. What's going to happen, we'll have to-start thinking of creative solutions. I am kind of against this as a workaholic, group up with an Irish-Catholic for work ethic, we will move to a four-day work week. If you give everybody three days offer, we have created 20% more employment on a mass basis. Another one, double the number of teachers, double the number of health care workers. And you do that, then the number -- amount of time they each have to have with each of the people that are working with would double or triple. Those would be good things for society. Of course, if you say anything creative like that in the environment that we live in -- and you are part of that environment as someone who talks about this at stuff -- you have to be careful. If I said that, oh, you are a socialist. I would say I don't know what you mean by that word in this context N 2015, but the world is moving awfully quick. When a lot of people are under employed and you see Operation Wall Street, that was like our little preview of what happens when a group of people gets disenfranchised. That was a completely ad hoc poorly run organization. That's why none of us are thinking about it all that much today, but they had a great moment in New York -- I mean effective. I'm not endorsing it necessarily -- but they went to Bloomberg's house, put 30, 40 people out of his town house and started protesting. When that happens, someone like Mike Bloomberg will be like if you are taking it to my front porch and I have to deal with this, okay, that four day work week thing works well. Or let's think about -- the really scary one, which I was dead set guest, now I am kind of starting to think about, is minimum income. This is a super-interesting --

GLENN: Whoa.

CALACANIS: I know you are thinking -- what minimum income means is cancel all the social programs and just give everybody innocent country $1,000 a month. If all the social programs -- we have 300 million people, equals this amount of dollars, just give everyone $1,000 a month. Then, rich people get it too. Everybody gets it. You could probably waive it or something, but at least your rent and your health care, whatever would be paid for. Not necessarily endorsing its, but if we got to 40% unemployment and had to figure out what to do with everybody, oh, my God -- this is probably at the end of our lifetimes.

GLENN: This is -- I will tell you, this is something we do -- this is the kind of thinking that I think middle America needs to start hearing. Instead of just hearing the stat, there's going to be a loss of 50% of jobs buy the year 2025, someone has to start talking about what does that really mean. What does that look like. And what do people do? Because that's the -- what's happening right now, I think we are being led by the elites, and it's because nobody is talking about this with regular people. So they just -- we are just fed this technology and just like oh, we have this technology, but no one is thinking about the ethics of it, no one is thinking about the consequences of it, no one is thinking about what it means when it starts to punch in and what it means for our children, my child, who is 10, when they are 25. What does the world look like? Not the way it looks now.

CALACANIS: It will be completely different. If we put ourselves back in time when we were kid, 40 years ago, 50 years ago, whatever it might be, the idea that you didn't work for one company for your entire life and pick that company and get a gold watch an get a pension would be terrorizing, but we don't have pensions today and we don't stay with the same company. There's upside as well. You could go out on your own and be like I don't want to work for a big network or big radio conglomerate. That's the freedom you have got front this unbundling of society and moving away from the control state, where you have this limited number of options. The unbundling -- and you having all this freedom to do whatever you want, the Internet and technology treeing you also means that yeah, the old structures are gone. The unions are gone. We have to have this many people build a car, because a union person said that's how many people its takes to build a car, as opposed to an expert telling us. That's changed.

GLENN: The real challenge here is, if you really do have freedom and the state is not in control of everybody's health, insurance, information, and they have clamped down as a totalitarian state to keep control, then I think we have a chance. But I'm afraid of the growth of the state at the same time, because while people don't like to lose power, governments certainly don't like to lose power.

CALACANIS: One of the things -- I think that interesting is the technology industry -- not endorsing, where observing -- kind of taking over the government and having a big say, just like some of the big industrial companies did for the last 100 years. So Megan Smith previously worked at Google. I'm friendly with her. You will see Sheryl Sandberg, COO of Facebook, I think you will see her take a cabinet position in Hillary wins, which looks like she's got a pretty good shot. And so I think you are going to see the technology industry be very involved in government more.

GLENN: Which I have to tell you, scares --

CALACANIS: We're coming.

GLENN: I know.

CALACANIS: We have the money to pay the politicians.

GLENN: I know.

CALACANIS: You know how this thing works.

GLENN: I do. And the idea that it becomes cozy bed fellows with everybody having a back door is really disturbing. The NSA is very disturbing.

STU: Can I ask a more important question here? How the hell did you get the Twitter name @jason?

CALACANIS: Good story. I'm at brunch with my friend Evan and Biz Stone. He created a blogging company. And I was in blogging. And he said look. Biz will tell you he's -- I will tell you I'm having the oatmeal, and you tell everybody you are having the pancakes. The SMS -- it was all SMS-based at that point -- shows what you had.

I looked at him and said Evan, you are going backwards in your career. Look, you took this post and got rid of the blog. Do you realize every idiot in America is going to start telling us what they think in a -- can I curse on this show? I was about to say the F word. It's not even a full sentence. It's a fragment. This is going to be a cacophony of idiotcy. I would never invest in something with a name such as Twitter. That's when you learn nobody knows. And if you think you know, you don't. Therefore --

GLENN: I would love to have you on again. I would love to -- in San Francisco, it should be quite interesting with two of us in San Francisco, taught about what future holds. Thank you so how much. Jason Calacanis. Launchfestival.com is the web site and thisweekinstartups.com.