After selling his first company, James Altucher went from having $15 million in his checking account to a balance of $143 within a short period. Then, he managed to build himself back up and sell another company only to lose it all again. Although he failed many more times, James never let fear stop him from taking action. His commitment to consistent experimentation led him to make several bold leaps, from web development to business, and from finance to standup comedy. In this episode, James and Ilana talk about how he is able to master new skills and reinvent himself quickly despite the fear of failure.  James Altucher is a bestselling author, serial entrepreneur, LinkedIn influencer, and venture capitalist. He has written over 20 books, including his most recent, Skip the Line.   In this episode, Ilana and James will discuss: - How he lost his fortune twice  - Lessons he learned from hitting rock bottom - The ‘10 ideas a day’ practice that changed his approach to life and business - The four areas he focused on to get himself out of a rut - Taking action in spite of fear - Execution as a subset of ideas - Hacking mastery by becoming the best at intersections - Having freedom no matter how many times you fail - The importance of being honest about imposter syndrome - Experimentation to prove your abilities to yourself - His crowdfunding experiment to buy Greenland - Thinking of luck in terms of experiments - His many leaps across diverse fields - The art of developing thick skin - And other topics…   James Altucher is a bestselling author, serial entrepreneur, LinkedIn influencer, and venture capitalist. He hosts The James Altucher Show, a popular business podcast. He has also authored over 20 books, including the Wall Street Journal bestseller Choose Yourself, ranked as the second-best business book of all time by USA Today. James has founded 20 businesses, 17 of which have failed, but continues to actively advise or invest in more than 30 companies across sectors such as technology, energy, healthcare, and biotech. Connect with James: James’s Website: https://jamesaltucher.com/  James’s LinkedIn: https://www.linkedin.com/in/jamesaltucher/  Resources Mentioned: Choose Yourself! https://www.amazon.com/Choose-Yourself-James-Altucher/dp/1490313370  James’s Books: Skip the Line: The 10,000 Experiments Rule and Other Surprising Advice for Reaching Your Goals: https://www.amazon.com/Skip-Line-Experiments-Surprising-Reaching-ebook/dp/B08BLLF3RD