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:


  1. How to pick a billion dollar founder or startup
  2. How to bounce back from failure
  3. 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:

  1. Get the book: https://amzn.to/2QpLqkX
  2. The book: Angelthebook.com  
  3. @jason on Twitter
  4. 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 steve@collectivecamp.us or tweet me on Twitter @steveglaveski or @future_squared

Follow me on Instagram: @thesteveglaveski

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



September 16, 2017




Steve Glaveski

Future Squared


Episode #276: The Corporate Startup with Dan Toma

Episode #252: Floptus Sport and the Five Whys

Episode 85: Ketones - All You Need To Know: With Joe Rogister

410: The Sh*t They Never Taught You with Adam Jones and Adam Ashton

Why and How to Get Your Brand into the Metaverse