Jason Calacanis is a venture capitalist, entrepreneur, angel investor, author, blogger and has years of perspective when it comes to investing in start ups. His new book is “Angel: How to Invest in Technology Startups–Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000”. Even if you never plan on becoming an angel investor, his book is a great look at how the modern economy works. Technology is accelerating at an ever-increasing rate and Jason argues that there are approximately 30 million jobs that will disappear in upcoming years due to advancements in technology. He wrote his book to try and help people step away from the usual way of thinking and look at where the world is moving. For example, the cheapest car you could buy today is far and above more sophisticated than the most expensive car you could have bought 20 years ago. When Jason evaluates a company, he looks at a couple things: What is in the best interest of society? And what is the best technology that we can use to get there? What is Silicon Valley like through the eyes of someone living and breathing it? Jason talks about Silicon Valley as the center of the world. There is an infectious need to look for the next $100 billion dollar idea rather than the next million dollar idea. It’s also very liberal, political and quirky. It is where the largest amount of high power tech companies derive from. What is the biggest factor in becoming a successful angel investor? Success in angel investing comes down to portfolio diversification. You need to cast a wide net, knowing you are going to have a lot of loser companies. There are massive implied odds. The upside to finding a winning company far exceeds any amount of losses you may incur. Michael relates this to the Babe Ruth effect and Jason puts his own spin on it, “Finding a winning company is more like the equivalent of a grand slam scoring 100 runs rather than just four.” In this episode of Trend Following Radio: Creating a global footprint Who is able to export their ideas around the world Silicon Valley Chinese border controls Unicorn companies Portfolio diversification Risk aversion