Angel Investing legend Jason Calacanis is an entrepreneur who sold his second business Weblogs to AOL for $30MM in 2005. Jason then founded multiple other companies and along the way, became an angel investor in companies like Uber, Robinhood, Calm and 300 others give or take. He’s the author of Angel, where he lays out his playbook for turning $100k into over $100MM. You may also know Jason from the All In Podcast with Chamath Palihapitiya, David Sacks, and David Friedberg or his other podcast This Week in Startups. The man is busy. It was a real thrill to learn about angel investing from one of the greats. I hope you enjoy this discussion with the multifaceted Jason Calacanis. IN THIS EPISODE, YOU'LL LEARN: 00:00:00 - Intro 00:03:35 - The advantages of being an outsider 00:13:25 - The realities of running a startup 00:19:16 - What makes up a founder and the ingredients for success 00:31:53 - Why so many startups fail and how to look for the signs 01:01:36 - Startup deal terms and syndicates 01:08:10 - Common traits of Jason's many billionaire friends and colleagues 📌 Get the freshest roasted and ethically sourced beans from America's best local roasters with Trade Coffee. To get started, take their quiz at https://drinktrade.com/TIP, and start your journey to your perfect cup. Plus, you get to enjoy a total of $20 off your first three bags! ✔️ Subscribe to Bitcoin Fundamentals/We Study Billionaires podcast show: https://open.spotify.com/show/28RHOkXkuHuotUrkCdvlOP 🖊️ Access our free show notes and transcript here: https://www.theinvestorspodcast.com 📖 BOOKS MENTIONED: - Angel: How to Invest in Technology Startups by Jason Calacanis - https://amzn.to/3549MN7 Disclosure: the link above is an affiliate link that we may earn commission from. This helps keep our show going! 😁 ▶️ PAST EPISODES MENTIONED - TIP 354: Building Berkshire 2.0 W/ Chamath Palihapitiya - https://youtu.be/wKHCCZnGzzE - Paypal Mafia w/ Jimmy Soni (TIP417) - https://youtu.be/vpsW23u7r08 💡OTHER RESOURCES - This Week In Startups Podcast - https://thisweekinstartups.com/ - All In PodcastThis Week in Startups - https://thisweekinstartups.com/ - The Syndicate Website - https://thesyndicate.com/ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ LISTEN 🎧 TO OTHER SHOWS FROM OUR NETWORK: ₿ If you're interested in Bitcoin, checkout our Bitcoin Fundamentals podcast show: https://youtube.com/playlist?list=PL_xlkwLDH1F8wOLjjwNCM5B1qFdrtTdTZ 📚Dive into value investing and learn more about billionaires with our We Study Billionaires podcast show: https://youtube.com/playlist?list=PL_xlkwLDH1F9dDPFYGAHRbrWoToCe2uoU 🏘 Learn the ins and outs of real estate investing with our Real Estate 101 podcast show: https://youtube.com/playlist?list=PL_xlkwLDH1F8Yw_8xO2nk-RD7fhb3yktn 💸Get introduced to the world of investing with our Millennial Investing podcast show: https://youtube.com/playlist?list=PL_xlkwLDH1F_p00VYv3psJ8rhDAGOvR5W ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ FOLLOW US ON SOCIAL MEDIA📱: 💻 Facebook: https://www.facebook.com/groups/theinvestorspodcast 👔 Linkedin: https://www.linkedin.com/company/the-investor's-podcast 🐦Twitter: https://twitter.com/tip_network ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ Download Stig & Preston's 1-page checklist for finding great stock picks: https://www.theinvestorspodcast.com/form-youtube-checklist/ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ ⏤ DISCLAIMER: This show is for entertainment purposes only. Before making any decisions consult a professional. This show is copyrighted by The Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting.