Jason Calacanis

Today’s guest is Jason Calacanis, a serial entrepreneur, angel investor, and author of Angel, a book about making investments and spotting trends. We talk about what the future holds for jobs, parenting, and education.

Jason’s 2 Cents

Kids value time the most. Love is spelled T-I-M-E in my mind. Leave your device off. Go on a hike. It’s not the number of hours, it’s how present you are. Kids are going to follow your lead. My daughter and I hike for two hours and then get lunch. I also do meditation with my daughter, which has been great for her focus issues.


The reason I wanted to have you on is because as an Angel investor you spot future trends
Anyone who is listening who is a father knows that this is the most important job title we have.

Let’s talk about the book.
* The book was my way of sharing how i went from rags to riches. But in this case from riches to mega riches.
* I had been a successful entrepreneur
* I’ve made mistakes, too, and what i have learned at the age of 42 is that people tend not to remember the mistakes, and tend to rally around your successes.
* Things right now have been a bit nasty in dialogue. I think podcasts are in renaissance right now partially because people want to have meaningful conversations.
* I’ve been ahead of the curve quite a few times, and being ahead puts you ahead of the crowd. In terms of Angel investing there are maybe a dozen people more successful than me, but none of them have chosen to write a book.
* I’ve hit six unicorns, which is what got me the opportunity to write this book for Harpercollins.
* When I was growing up I had no idea how wealth was created, and this is my way of sharing that.

How do the founders that read this book carry those principles into their company to see what’s coming?

  • It’s super easy for someone who is a founder to identify who angel investors are today.
  • Finding them isn’t the problem, the problem is understanding them and what they want.
  • Founders tend to bend the truth to impress investors. 2 or 3% of the companies i do due diligence on i find are lying about the state of their business.
  • If you’re an angel investor, the opportunity is investing in potential. The expectation is that things won’t be perfect.
  • As gen Xers, we were trained that wealth is created by a good job, frugality, and owning a home, paying it off, and investing in more homes.
  • My parents paid $45,000 for their brownstone in Brooklyn on blue collar jobs. Combined income was about 1x the cost of the home. If they put 10% towards the home they’d be done in ten years.
  • Now that brownstone is worth about 1 million. Blue collar combined income around $100,000. It would end up being 10x blue collar income. That way to make money is gone.
  • 30 million jobs in retail and driving are going to evaporate. So cashiers fight for a living wage, and then those companies replace cashiers with kiosks.
  • So now people won’t have to sit in a tollbooth, drive a truck, or make you a coffee–work hard jobs. So what are they going to do?
  • Our kids are going to live in a world that flips three times. Internet, AI, Biology, etc.
  • How do we prepare our kids for that?

What has to change to adapt to that future?

  • I believe the education system will not serve them well–reading, writing, arithmetic, socializing are all essential of course. I don’t think the school systems served us well. I see a lot of middle aged contemporaries of mine are being aged out in Silicon valley.
  • I have taken it upon myself to teach my 7 year old and 16 month old twins about business.
  • My daughter, I took her to my incubator and told her that she could either go to college or start a business.
  • If she wants to be an artist she’s privileged enough to have a dad who can underwrite that–I didn’t have that. My options were firefighter, cop, bartender, etc. I ended up in computers and this is where I am.
  • Right now my daughter is going to start an ice cream business with her $300 in savings. We’ve been doing market research, she’s going to learn cost of goods and unit economics, marketing, customer support. We’re going to go to a pop up store or farmers market. I don’t think anything she’s learning in school would allow for that kind of focus.

What are the trends in the schools that you’re seeing to help with these changes?

  • I see a lot of people focused on exactly the wrong thing, which is status and competition.
    People are obsessed with kids getting into colleges, ap classes, math achievement, etc.
  • They’re obsessed with their kids being in the schools of billion dollar founders’ kids.
  • Lots of keeping up with the joneses
  • There is a high suicide rate in Palo Alto because of high competition. For one of the most affluent places in the country to lead in suicide rates for children should make the parents reassess.
  • In my mind it’s the parents’ fault. Collectively/culturally.
  • I tell parents who are freaking out about where their kids will go to school, i tell them about my background. I went to public schools and did poorly in high school. I have more success than most of the people i meet from Harvard. Ivy league is not all that. The people who are happy have a sense of mastery, and a sense of joy that they get to participate in something purposeful that matters to them. We don’t need to live a Kardashian lifestyle. The Kardashians are not a happy family–that’s not what we need to be like. It’s a mixed message of what success is.
  • I want my daughters to feel like they can accomplish anything and not be distracted by all the crap.
  • We follow a reggio style education system. If the kids are interested in orcas, teach math or reading by using examples of orcas. It makes them excited about going deep.
  • So I sit down as a mentor with some of my employees and ask them what success looks like for them. I don’t think enough people have thought about what success looks like for them.

How did you and your wife arrive at this? There’s a trend of lack of focus, people aren’t slowing down and asking themselves the important questions.

  • If you look at ADD and ADHD and aspergers. This inbound existence…it’s having an impact on people’s brains.
  • The idea of dying a violent death has gone down significantly, the idea of living in abject poverty has gone down, so much so that the things that will kill us are self inflicted and highly avoidable–like suicide. In the developing world where there are fewer regulations, more of these accidental deaths happen like commercial plane crashes. In Germany a suicidal pilot runs a plane into a mountain. It’s not because of the actual act of flying. It’s a long way of saying that our kids are going to live in a world where starving to death won’t be the cause of death, overeating will be the cause of death.
  • I was talking to an educational psychologist about our daughter who doesn’t like to sit still in the classroom, and she mentioned medication. How will she function as an adult in the world otherwise. We thought that was crazy, that a kid who runs around at age 7 years old is broken and needs to be medicated to sit down at school for 6 hours.
  • Workplaces are trending against this sit still for 8 hours thing. People are working in bust style fashions with intermittent physical activity.
  • We should rethink the classroom if the kids have this much energy. We need to accommodate the kids and their needs.

I am with you, that the schools aren’t changing. Who is tackling this?

  • I think the teacher to student ratio needs to be no more than 10 to 1. I would love if we would raise the tax rate on the country’s top earners, and then quadruple the number of teachers there are, and double the number of hours in school.
  • School should be available 7 days a week, 7am to 7pm. If you need to work on a saturday, drop your kids off on a saturday where they’ll do project based learning.
  • It would not cost that much for us to have schools available like this. Anyone who says it would cost too much just doesn’t understand the numbers.
  • The tax breaks we offer are criminal. I benefit from them, and they’re terrible. If you went to the top million earning americans and told them we were going to charge 4% more on your taxes, and we’ll have 7 days a week schooling available for kids, you would have 99% say yes, and 1% say “i earned mine!”

I would agree that our investments are so lopsided, what other things should change about the schools?

  • I think if you look at youtube, Lynda, conacadamy, treehouse, etc. corsera, edex, we’re living in a society where you can afford to acquire any skill online.
  • If we have all the information line to learn these skills, then why aren’t people doing it? I’ve heard that people don’t have enough time, that they don’t have it available, or they don’t have the precursor education. There is always time, and $25 a month is not a lot. It’s not an insurmountable hurdle. And often it’s free.
    People ask me all the time what they should be learning, and i say look at linkedin and see what people are looking for.
  • People used to be proud of working hard and acquiring skills. Everyone wants the kim kardashian private jet, but they’re not willing to put the work in.
  • When I was growing up this information wasn’t available for free, you had to go to college for it. Knowledge is so cheap and available, yet people don’t want to read books or learn skills.
  • So we’re at this crazy moment in time where one group of people are capitulating and feel helpless, and the other feels empowered.

Why do you think that is? What role do the parents have in that?

  • I’ve heard role models is one piece, so if you don’t see someone who looks like you in a role, then you might not even consider something as a possibility. Race, gender, etc.
  • I also think we live in a victim society where people feel that the world is against them. We’ve made it easier for the rich to get richer, and harder for poor and middle class people to move up. We’ve rigged the system at the same time that low income jobs will disappear at a high velocity. It’s very scary.
  • But there are solutions, but people don’t want to hear the solutions to society’s problems. There’s a burn it down mentality.

It feels a bit hopeless

  • It feels bad because we always expect things to get better, and for a lot of people it’s not getting better.
  • We are addicted to our social media, which feeds us terrible news and great news all at once…using an algorithm that is designed to mess with our emotions on a rage, sadness, and joy cycle. People who design these algorithms need to take a look in the mirror and think about what they’re doing. Fake news plays a role in this, too, which has serious consequences.

What’s one piece of advice that you would give to a new dad?

  • Kids value time the most. Love is spelled T-I-M-E in my mind. Leave your device off. Go on a hike. It’s not the number of hours, it’s how present you are. Kids are going to follow your lead. My daughter and I hike for two hours and then get lunch. I also do meditation with my daughter, which has been great for her focus issues.



Schools and Organizations


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