Jason Calacanis
2 Cent Dad Podcast
download episode

Editorial Summary

December 27th, 2019

Despite what they tell you, the world is a Zero Sum game. That is what Jason Calacanis, a notable angel investor, would make you think. Do you believe him? Jason went from broke to a millionaire, so he knows a thing or two about surviving. Now he is raising his kids to outperform against their peers. How? Take a look at the Smash Notes below and you will find out!

Did you know Smash Notes is a podcast too? Subscribe ->


Who is Jason Calacanis? 01:11

Jason is a serial entrepreneur, Angel investor, and author. He has recently wrote a book called, Angel.


What is the greatest investment we can make? 01:59

Kids are the greatest investments.


Why did Jason write Angel? 02:27

Jason says that writing Angel was his way of sharing how he, essentially, went from rags to riches. In the book’s case, rich to mega rich. He is the first successful Angel investor to write a book about it.


At the age of 46, what has Jason learned? 03:09

That people tend to not remember mistakes, but will rally around your victories.


Why are podcasts becoming so popular? 03:41

Because people like to have meaningful discussions that are not like a screaming match on Twitter. Instead, podcasts allow people to be heard.


What are some problems when it comes to investing? 07:28

Finding investors is not the problem, it’s understanding what makes them tick, how they make decisions, and having empathy for them. Most founders do not take these factors in account.


As a parent, how can you prepare your children for the changes in society? 18:07

Jason is teaching his twin teenaged daughters on how to make their way into the world. As for his seven year old daughter, he explains to her about his business. He is providing her with more advanced knowledge than what school offers and teaches for people to consider to pursue as a possible career.


What are the wrong things that people are focusing on? 23:46

These include status and competition, which are all shallow concepts. Parents obsess over their children getting into college, taking AP courses, and hitting unhealthy achievements.


Why aren’t the Palo Alto suicides mentioned in the book? 25:47

When you write about the topic of suicide, more people view this as an option. The Palo Alto school leads the country in suicide death rates due to the students’ parents being highly successful people that pressure their kids to get into top schools.


What does Jason say to parents obsessed with their kids going to a great university? 29:55

Jason went to public school and he was not the top of his class. Yet, he has had significantly more success than some who graduated from Harvard.


Who are the people that are going to be happy in life? 30:49

It's the people who feel a sense of mastery, that they have control over their destiny. They have realized that they don’t need to be better than the person next to them. Instead, they should judge themselves on the work they’re doing in the world, how it aligns with their own interest, and wake up every day with a sense of joy.


What kind of world are we living in? 31:49

We live in a world with peer pressure and social media influence. People feel like they need to live this Kardashian lifestyle, Jason uses as an example. This is not what life is about. Self-worth is being determined by what's being worn and what events people attend each year.


What does Jason want his daughters to grow up to be? 33:10

He's raising them to be bosses, not bossy. He wants them to feel like they can accomplish anything, to know what motivates them, and for them to be super confident in their abilities.


What are the things that will kill us? 39:45

As the idea of dying a tragic death and of starving to death are ideas that have gone down significantly, the things that are self-inflicted and highly avoidable will kill us.


What should be offered in schools? 50:43

Jason believes that schools should adjust their operating hours and also be open seven days a week to fit both the parents and children’s schedules and needs.


What should society start cherishing? 58:34

We should start cherishing the pursuit of skills and education. Calacanis states how America was once proud to work hard and obtain new skills.


Without role models, how can a dream be discouraging? 01:01:11

If you don’t see people who look like you or are doing what you want to do, then you dismiss your idea or possibility because you don’t see any higher influences doing what you dream of doing.


What is the “burn it down” mentality that society has right now? 01:06:37

Jason thinks that people don’t want to hear that there are possibly solutions to society’s problems since things have been bad for so long. This mentality is toxic because we have lost the ability to collaborate or use common sense to solve problems.


What is a theory going around in Silicon Valley? 01:11:25

That Facebook was paid to post fake ads that they reviewed for fake news that targeted a certain area of people.


What is a piece of advice for first time dads? 01:15:30

Jason says that kids value this four letter word the most: time. In his mind, love is spelled as time. It doesn’t matter how many hours you spend with your children, what matters is how present you are with them.

Suggested Episodes

Sign up for the newsletter!