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How Jason Calacanis turned $100K into $100M

Lessons from Jason.

  • Create, don’t wait. Just about every entrepreneur has created tons of projects that have failed and were forgotten. You only need one success to make an entire career, so just keep creating.
  • Stick with it. Most companies don’t fail because they run out of money, or they have a bad product. They fail because the founders quit. The magic happens after doing it 100s of times.
  • Do the work. There is a direct correlation between how hard you work, how many hours you work, and how successful you are. The majority of the time, being extremely successful requires you to work 6–7 days a week. Your 20s are the time to put in 60–70 hour work weeks.


  • From the beginning, Jason was always a voracious networker.
  • Since his early days, Jason read constantly and was always trying to grow his skill stack.

Book recommendations.

  • The Fish That Ate the Whale — Rich Cohen
  • Born Standing Up: A Comic’s Life — Steve Martin
  • The Lean Startup — Eric Reis
  • Shoe Dog — Phil Knight

Jason’s 20s.

With early angel investments in companies like Uber and Robinhood, Jason Calacanis managed to turn 100 thousand dollars into 100 million.

Many, himself included, call him lucky.

However, the connections made and the lessons learned during his early years as a journalist later helped him gain access to the best founders and the best deals as an investor.

While in night school at Fordham University, Calacanis was looking to discover how wealth was created and how people became powerful. Back then the best place to hope to find answers for those questions was in magazines, better yet, through small, independent, photocopied magazines called zeens.

It was at one of these zeens, Paper Magazine, where he cut his teeth in the world of publishing.

Calacanis eventually graduated to form his own independent magazine; a meager consortium of 16 pieces of photocopy paper stitched together covering New York City’s Dot Com era called Silicon Alley Reporter.

While at Silicon Alley Reporter, with basically no money, Jason would network by throwing parties and hosting dinners. He would invite people that he considered to be more important than him and then would use their names to invite even more important people. This trait of hyper networking created a flywheel of connections that would last multiple decades.

Calacanis was offered $20 million for Silicon Alley reporter, but he didn’t take it. A short time later he sold it in a fire sale for just around 500k.

This hard lesson led him to sell his next company, Weblogs, inc., just 18 months after its founding. Now with millions now in hand, he was dangerous.

Jason then joined Sequoia Capital as a scout and as an entrepreneur in action where a short time later he made his infamous $25K investment in Uber when the now $89B was only valued at $5M.

The rest is history.


Listen to the full podcast with Jason.

Here’s a 1999 New Yorker article on Jason.

Jason Calacanis at 29



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