Trey Lockerbie chats with Angel Investing legend, Jason Calacanis. Jason 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.

IN THIS EPISODE, YOU'LL LEARN:

• 01:38 - The advantages of being an outsider.
• 06:10 - The realities of running a startup.
• 09:28 -What makes up a star founder and the ingredients for success.
• 13:32 - Why so many startups fail and how to look for the signs.
• 37:56 - Startup deal terms and syndicates.
• 45:31 - Common traits of Jason's many billionaire friends and colleagues.
• And a whole lot more!

*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.

BOOKS AND RESOURCES

• Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members.
• Angel Book.
• This Week In Startups Podcast.
• All In Podcast.
• The Syndicate Website.
• Inside Newsletter Website.
• Jason Calacanis Twitter.
• Trey Lockerbie Twitter.

NEW TO THE SHOW?

• Check out our We Study Billionaires Starter Packs.
• Browse through all our episodes (complete with transcripts) here.
• Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool.
• Enjoy exclusive perks from our favorite Apps and Services.
• Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets.
• Learn how to better start, manage, and grow your business with the best business podcasts. 

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• Onramp
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