Future Squared Episode #181: $100K to $100M with Jason Calacanis

September 16, 2023

Future Squared Episode #181: $100K to $100M with Jason Calacanis

Jason Calacanis is a tech entrepreneur, wildly successful angel investor, and the host of the popular weekly podcast This Week in Startups. He’s the founder of a series of conferences that bring entrepreneurs together with potential investors.   

As a “scout” for top-tier Silicon Valley venture capital firm Sequoia Capital and later as an angel investor, Jason has invested in 150 early-stage startups including four that have achieved billion-dollar valuations (so far) such as Uber, Evernote and Tumblr.   Jason’s newly released book “Angel: How to Invest in Technology Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000” puts readers inside the minds of successful angel investors, helping to understand how they prioritize and make the decisions that have resulted in phenomenal profits. Jason provides a step by step roadmap, revealing how leading investors evaluate new ventures, calculating the risks and rewards, and explains how the best startups leverage relationships with angel investors for the best results.   

In this episode we go back to Jason’s rough upbringing in Brooklyn, NY in the early 80s and cover a lot of ground leading up to the present day so you can expect to learn a lot of things, including:   

How to pick a billion dollar founder or startup How to bounce back from failure 

What Jason thinks of and what advice he has for corporates investing in startups  

All topics discussed: 

Jason’s humble beginnings in Brooklyn, NY 

What got Jason into startup investing 

The alchemy of startup investing 

Why you should always wait for external validation from other investors before investing 

Why ideas are a dime a dozen and you should invest in startups that have demonstrated traction 

The biggest mistake first time startup investors make 

The changing nature of angel investing and venture capital 

On books becoming a business card for many people 

Why building quality deal flow is a popularity contest of sorts 

How to get started investing with little money 

The number one thing Jason looks for in entrepreneurs 

Other factors to evaluate startups and entrepreneurs, including Jason’s ‘four founder questions’ 

How Jason navigated his Silicon Valley Reporter going bust during the dot com boom 

How to ask good questions 

What Jason’s views on corporate venture capital are and what advice he has for corporates looking to or already investing in startups 

How to go about taking lots of small bets when diversifying and building your portfolio 

What Jason thinks about ICOs, cryptocurrency and blockchain 

Show notes: 

Get the book: www.amazon.com/Angel-Invest-Tech…tor/dp/0062560700

The book: Angelthebook.com   

@jason on Twitter 

Jason’s podcast: ThisWeekInStartups.com

Listen on iTunes @ goo.gl/sMnEa0 

Listen on Stitcher @ www.stitcher.com/podcast/future 

Listen on Google Play @  bit.ly/FSGoog 

If you’ve got any questions on this podcast feel free to send an email to [email protected] or tweet me on Twitter @steveglaveski or @future_squared 

Like us? It’d make our day if you took 1 minute to show some love on iTunes, Stitcher or Soundcloud by subscribing, sharing and giving us a 5 star rating. To sign up to our mailing list head to www.futuresquared.xyz 

For more information on Collective Campus, our innovation hub, school and consultancy based in Australia and Singapore check out www.collectivecamp.us

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Steve Glaveski

Steve Glaveski is the CEO and Co-Founder of Collective Campus which he established to help companies and their employees to create more meaningful impact in the world in an age of rapid change and increasing uncertainty. Steve also founded Lemonade Stand – a children’s entrepreneurship program, wrote the Innovation Manager’s Handbook vol 1 and 2, hosts Future², an iTunes chart topping podcast on corporate innovation and entrepreneurship and is a keynote speaker. He previously founded HOTDESK, an office sharing platform and has worked for the likes of Westpac, Dun & Bradstreet, the Victorian Auditor General’s Office, Ernst & Young, KPMG and Macquarie Bank. Follow him at @steveglaveski and Book a free 15-minute call with Steve to talk through your innovation objectives.

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