Patrick McGinnis. He’s the author of The 10% Entrepreneur which focuses on living your startup dream without leaving your day job, which was just published by Penguin Portfolio. He’s also credited for coining up with the term “fear of missing out”. He’s a graduate of Harvard business school and is living in New York City. Famous Five: Favorite Book? – The Lean Startup What CEO do you follow? –  Sheryl Sandberg Favorite online tool? — Quip Do you get 8 hours of sleep?— 6-12 If you could let your 20-year old self, know one thing, what would it be? – Patrick wished he had more confidence in his abilities and more open to trying new things   Time Stamped Show Notes: 01:30 – Nathan introduces Patrick to the show 02:10 – Patrick is a Wall Street refugee 02:21 – Patrick has his own advisory firm 02:29 – Patrick built up his portfolio of over 20 investments 03:04 – Patrick worked with his friend in Real Influence for free 03:14 – They sold $300K-$400K 03:19 – The business didn’t push through and Patrick sold his shares 03:35 – Patrick was 33 03:46 – After a year, Patrick’s friend asked him if he was interested in investing in a startup 03:51 – Ipsy has raised $100M 04:08 – Patrick is one of the first investors of Ipsy 04:32 – Ipsy’s co-founder is Michelle Phan 04:49 – Patrick’s friend who is the CEO of Ipsy met Michelle through Funny or Die 05:46 – Michelle’s huge fan base made Ipsy spend zero on CAC 06:00 – How Patrick decided to invest in Ipsy 06:03 – Patrick’s friend was already raising a round 06:33 – Patrick’s friend already had a lead 06:38 – Patrick started his venture capitalist path in 2000 06:48 – Most of the deals Patrick looks at are simple deals 06:53 – Patrick invested in Ipsy in 2012 07:50 – Ipsy is one of Patrick’s most successful investments 08:00 – Another one of his investments was Bluesmart 08:24 – He also invested in Affinity which is a big data company 09:04 – How many deals do you have to make to ensure there’s a big exit in the portfolio? 09:12 – When Patrick started investing, he thought of the possible mistakes he could make as an investor 10:03 – As an investor, you have to invest in your area of expertise 10:08 – Second, think of the deal as a commercial deal, even with friends 10:21 – Third, don’t follow other people 10:39 – Stay away from “will-to-be” syndrome 11:09 – Patrick was working with AIG’s private equity fund 11:41 – Patrick shares why he wrote a book 11:48 – Patrick always talks to people about what he does as an investor 12:12 – As Patrick met with more and more people, he realized that he could actually help people believe in what he does 12:25 – “It’s been a blast actually and I love writing, anyway” 12:56 – Patrick shares why he decided to have a publisher rather than self-publish his book 13:02 – Patrick wasn’t a well-known media figure and a publisher would help his credibility 13:12 – Patrick got a great editor 13:24 – Patrick wanted to go global 13:34 – Patrick has sold an average of 50K copies 13:40 – A book update is given every 6 months 14:00 – Patrick gets around 10% royalties on sales 14:26 – Patrick’s book is a bestseller in South Korea 14:48 – Patrick had an advance of around $100K prior to his book launch 14:58 – Patrick has an agent who is with UTA 15:38 – Patrick met his agent through his friend 16:02 – If you are generous to the world, it comes back to you in so many different ways 16:25 – “If you want to publish a book, you should know how hard it is” 16:40 – Publishing a book is like running a startup 16:54 – Patrick shared on a couple of podcasts which boosted his sales 17:03 – Patrick’s book is in physical bookstores, too 17:20 – Patrick was also live in CNN Espanol in South America 17:37 – Amazon’s ranking is always updated 17:44 – Patrick also has a group who does social media for him 18:22 – Launching a book is a process 18:56 – Patrick has a day job that covers the bills 19:12 – “Freelancing is great in terms of flexib