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Jason Calacanis - Entrepreneur turned Investor shares his insight about success, hard work, education, and the future.

Do you want to get inspired? This episode is for you.

Jason Calacanis is a serial entrepreneur and angel investor. He was one of the early believes in Uber, Calm, Robinhood and many others. He is a host of the show This Week in Startups, and the author of Angel, a founder of Launch.co, Inside.com, and a friend to many rich and famous folks in Silicon Valley.

On this episode, Jason shares his views and wisdom, advice that he's accumulated throughout his career, and lessons learned from other successful entrepreneurs like Elon Musk, Mark Cuban, and Jeff Bezos.

Updated on March 24
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Key Smash Notes In This Episode

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It all depends on your aspirations. If you desire to start a billion-dollar venture backed high-growth company, you are going to have to work harder. If you are satisfied with a small business that just makes money to live off, chance are you won't work as hard.

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Jason speculates that we are now living in a society where surviving has gotten so easy that it removes the edge and fear.

On the other hand, work, entrepreneurship, and capital has become portable, and you are now competing with anyone who can do your work, around the world. It could be demoralizing.

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"Bootstrappers are my people." ~ Jason.

There are two groups of people in the world: people who write checks and people who are so good at what they do, the are so resourceful, they build it themselves.

Jason loves to invest in people who were able to elevate themselves without a handout.

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The most successful founders are opportunistic and take control of the world. They never feel victimized.

Who you hang out with changes how you think about the world.

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"It's not even necessary money over people, because that would be like looking at it in the most first order, you know, superficial way. It's if a large number people lose their jobs cannot afford health care. Stop going to Dr Start abusing opioids or alcohol. Ah, full into depression commits suicide because they go bankrupt like you can actually track these things.

It just takes a moment of taking a deep breath and saying, Oh, there are second order effects and buried water effects of every action, and we have to think holistically when we do things in different systems in the world. So for every time you put an incentive out there, it could have dire consequences that you didn't expect the unintended consequences of actions at scale are things you really need to theorize in question and debate. And now you've got people who don't want to do that because crazy like you were talking about taking major action here, Should we be canceling?

Whoa, ah, student debt. Should we be giving businesses blank checks? Where should we be buying equity? Or should we be giving them loans? Should be giving them loans with no interest rate or some interest rate. If we have loans with that with an interest rate than people who have savings,

get interest that they could then spend if we don't have interest within, businesses can take money for free money and build more companies and build the economy faster. Okay, which is better? It's like, Yeah, I don't think anybody actually has the answer to that question of having no interest rate and more people investing in building things or having a modest interest rate or a medium interest rate that allows people to make money off of their savings, which they can then put to work.

And it promotes a healthier environment where people save more. Right now, there's no incentive to save. Obviously, if you've got 10% or 15% on the money you have in the bank, people like I'm gonna try to get 100,000 in the bank so I could make 15,000 on my interest. Now it's what I put 100,000 in the bank and get back $94,000 in 10 years. That doesn't make any sense."

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Jason's Syndicate is analogous to Angel List and is the main driver for how Jason now aggregates angels to invest in his deals.

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"Brian Alvey would come over, he came over, I think 29 times on I would do about two or 3000 words. He would come over. He'd edit them real quick, and then we talk about it. Then we go for a walk. We'll get some Mexican. True, both, Like Mexican food.

Then we walked back to my house and talk about it a bit more. And what other topics you want to do? This. I'd say I got about 80 70 or 80% of it done in those 30 days on."

They were going to write more chapters, but the editor read it and said it was the perfect time to publish!

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YouTube! Open YouTube and look up how to do whatever it is that you need to do. There is a video out there for mostly everything.

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Jason and family are big on Montessori and Reggio activities, tools and techniques which center around the child. Anything the child can do, let them do it.

His 3 year olds cut food, while the 10 year old bakes their dinner. They know how to do it, and it's really rewarding to see your kids take care of themselves independently.

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When you practice martial arts or you learn how to use a firearm, you learn how fragile you are. You learn how dangerous the world is and how to avoid those situations.

Being able to assess a situation, and to get through it on their own, without help, is what would give kids their confidence.

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Jason wants founders who are resilient, and hungry for the opportunity. The founders gotta know their numbers, have revenue, and be proactive about chasing their dream. They have to be serious about their mission.

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When Jeff Bezos was still angel investing, he offered to meet Jason in Seattle if Jason was ever in town. Immediately, Jason booked a flight and was on his way to Seattle.

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He loves them, and he will always be there with them, and that they can do anything if they put in the effort, and do the work.

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