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WATCH: Uber Investor Jason Calacanis — ‘Millennials Want To Change The World’ Without Doing Work 

As the king of angel investors, Jason Calacanis knows that unicorns exist.

He knows this because he has invested in some unicorns, the term for startups valued at more than $1 billion.

Jason Calacanis has invested in popular ride-sharing app Uber, smartphone stock trading app Robinhood, and 3-D metal printing company Desktop metal. These companies, among others, serve as his diamonds in the rough that have paid off well. On Bold Business’ live show, Jason talks about his book Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 and shares his advice for millennials. Watch here on our Facebook page.

Where he started

Jason began his career as a journalist in New York, but he quickly made a smooth transition into the startup world. The skills he accumulated as a journalist allowed him to have a competitive edge in the startup space. Jason developed a keen eye for authenticity, something that is fundamentally crucial in the hunt for successful startups.

In fact, Jason noted that what journalists do is essentially the same as what angel investors do. Activities such as asking the right questions and attentive listening carry over across the two fields, while the pay scale, of course, does not.

What to look for in startups

Jason identified two key things to look for to adequately predict a startup’s chance of success. The first, passion, can be seen right away in how a founder or lead member of a startup speaks of his or her own company. Many are enamored with the startup space, but few are willing to rough it out through the hardships that come associated with being an entrepreneur. When it comes to starting a business, hustle is essential, and investing in hustle can pay off well.

The second key thing to look for is the quality of work. To succeed in the startup world, you need to invest in doers. That’s because doers get things done, and they care about results. Attention to detail is essential because even the little things can make or break a product.


Jason Calacanis has a history of startup investments that serve as examples for the rest of us. Investing is a game of risks, but Jason’s record of success shows that it’s all about knowing which risks to take. And maybe, if you read his book, you’ll become a star angel investor, too.

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