Jason Calacanis, Super Angel & Podcast Host

Angel Invest Boston

Learn About Sal's Syndicates: Link to Sal's Syndicate Page

Silicon Valley's angel-investing phenomenon Jason Calacanis is our guest. Hear how he turned $700K into a portfolio worth $100 million. We had an inspiring conversation about building companies and investing in them.

Highlights include:

• Sal Daher Introduces Jason Calacanis as his Guest on Angel Invest Boston
• How Jason Built the Stellar Team that Makes His Success Possible
• Sequoia Capital Picked Jason Calacanis to Scout for Promising Ventures
• How Jason Calacanis Turned $700,000 into $100 million
• Jason Calacanis Once Thought Angel Investing Was Stupid
• The Odds of Success for Founders and for Angels
• “…we live in a time when people believe in balance, and they believe in getting Olympic-caliber rewards…but they only want to commit to putting in 40 hours a week.” Jason Calacanis
• Investment Syndicates versus Funds
• VC Returns Have Note Been Spectacular
• “If you want to be active, you can do syndicates…”
• “My personal goal is to train 10,000 people to be active investors in thesyndicate.com. We've got 3,300 members.”
• Why Jason Leads Syndicates Despite Having Raised Several Funds
• Syndicate Members Act as Scouts, Bringing in Interesting Companies Jason Would Not See Otherwise
• Syndicate Members Can Be a Resource to Founders
• As His Syndicates Develop, Jason Calacanis Hopes to Match Investor Background to the Needs of Companies
• “For me, media is my leverage…” Jason Calacanis
• Success Brings More Success
• How “This Week in Startups” Podcast Came About
• The Responsibility That Comes with Success
• “And I watch my contemporaries, and I hold many of them in contempt for the cavalier nature of which they go through their work. They must take the work seriously.” Jason Calacanis
• Jason Calacanis’ Launch Accelerator – Sam Bogoch of Axle.ai Found It Very Useful
• Jason Calacanis Recommends “Skin in the Game” by Nicholas Nassim Taleb
• “Angel” by Jason Calacanis, a Manual on How to Be an Angel Investor
• How Y-Combinator Plays the Odds
• Jason Is Building His Organization So He Can Start Delegating Investment Decisions
• Delighting Your Clients Is Essential, But It’s Not Enough: Luxe Valet
• The Unit Economics Has to Work for a Company to Make Delighting Its Customers into a Business
• “I think we could have at least 10 times the number of people participating in angel investing than we do here in the United States”. Jason Calacanis
• “Start small and start slow. Yes. And you know, it's just like learning how to play poker or blackjack”. Jason Calacanis on Angel Investing
• Jason’s Advice for Angels & Founders
• Distinctions Between a Life Style Business and a Venture Business