The Entrepreneurial Journey: Grit, Investments, and Contrarian Ideas

This chapter explores the essential qualities of grit and resilience that entrepreneurs need to navigate failure. Through personal stories and a strategic investment in an ambitious tech company, it highlights the importance of early connections and visionary thinking in overcoming challenges.

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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.

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