TIP433: The Art and Science of Investing in Startups w/ Jason Calacanis

The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network

Stig Brodersen

Business, Education, Investing

4.6 • 3.6K Ratings

🗓️ 25 March 2022

⏱️ 60 minutes

🔗️ Recording | iTunes | RSS

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Summary

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. SPONSORS Support our free podcast by supporting our sponsors: HardBlock Human Rights Foundation Vanta Plus500 Netsuite Shopify HELP US OUT! Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Transcript

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0:00.0	You're listening to TI-P.
0:03.2	On today's show, we have Angel investing legend Jason Callacannis.
0:07.2	Jason is an entrepreneur who sold his second business web blogs to AOL for $30 million
0:11.9	back in 2005, and then he went on to found multiple other companies, and along the way, became
0:16.6	an angel investor in companies like Uber, Robin Hood, Calm, and 300 others give or take.
0:22.1	He's the author of Angel where he lays out his playbook for turning $100,000 into over
0:26.0	$100 million.
0:27.0	And you may also know Jason from the All-In podcast with Chimoth Paul Habatia, David
0:31.4	Sacks, and David Friedberg.
0:33.2	Or his other podcast this week in Start-ups.
0:35.8	In this episode, we discussed the advantages of being an outsider, what makes up a star
0:40.1	founder, and the ingredients for success, the realities of running a startup, why so many
0:44.9	startups fail and how to look for the signs, common traits of Jason's many billionaire friends
0:49.7	and colleagues, startup deal terms and syndicates, and a whole lot more.
0:54.4	He was a real thrill to learn about angel investing from one of the greats.
0:57.9	So I hope you enjoy this wide-ranging discussion with the multifaceted Jason Calicanas.
1:07.1	You are listening to the Investors podcast, where we study the financial markets and read
1:12.2	the books that influence self-made billionaires the most.
1:15.4	We keep you informed and prepared for the unexpected.
1:27.7	Welcome to the Investors podcast.
1:29.4	I'm your host, Tray Lockerby, and today I'm super excited to have with me on the show,
1:33.6	Jason Calicanas.
	...

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