Jason Calacanis, Entrepreneur and Angel Investor
Today, my guest is Jason Calacanis, a successful entrepreneur and angel investor. Born in Brooklyn, New York, Calacanis's first success was starting Weblogs, Inc., which was sold to AOL in 2005.
Since then, he has been an angel investor in numerous successful entrepreneurs and companies such as Travis Kalanick at Uber, Thumbtack, Tumblr and many others.
Jason is the CEO of Inside.com, has been a guest on Charlie Rose, has his own podcast This Week in Startups, his own entrepreneurs startup forum Launch Festival and is a frequent contributor and guest on CNN.
In this candid conversation, Jason shared the real stories behind his transition to an accidental angel investor, the secret to spotting billion-dollar founders, and his unique strategies for scaling his time.
1. Founder-Product Fit. Jason clarified he is an angel investor, not a venture capitalist, and shared what he believes is the crucial element of a successful startup. While many people focus strictly on finding "product-market fit," he argues that "founder-product fit" is actually even more important at the early stages. Because building a company is grueling "Jedi work" filled with unrelenting bad news, founders must be absolutely obsessed with their product—like Travis Kalanick at Uber or Elon Musk at Tesla—so they never give up when facing inevitable roadblocks.
2. The Open Angel Forum and Uber. Discussing his massively successful early investment in Uber, Jason attributes the opportunity to his long history of relentlessly supporting founders. Before platforms like AngelList existed, he created the Open Angel Forum, a free event where angels bought burgers and beer for founders debuting their companies. It was at this forum that Travis Kalanick pitched Uber; because Jason already knew Travis to be uniquely driven and "indefatigable" from his previous startups, he confidently joined the seed round of what became a once-in-a-decade company.
3. An Accidental Angel. Reflecting on the exhausting, sleepless nature of being a full-time entrepreneur, Jason admitted he considers it a "young person's game". He eventually transitioned into being an "accidental angel investor" after Roelof Botha from Sequoia Capital pushed him to become their very first scout. To effectively manage his massive portfolio today, Jason employs a proprietary time-management secret: instead of doing one-on-one meetings, he frequently takes five or six founders to lunch at the exact same time. This strategy not only heavily scales his own time, but actively builds a supportive peer network among the entrepreneurs.
4. Brooklyn Roots and Future Ambitions. Jason attributes his intense extroversion and love for energetic debate to his childhood in Brooklyn, where he entertained himself by sitting on the stoop or working in his father's bar "busting chops" and discussing the world. Looking toward his next chapter, he is currently channeling this immense energy into writing a book for Harper Collins, maintaining a strict pace of a chapter and a half every week. Unwilling to slow down, he already has ideas for two more books and eventually wants to dive into investigative journalism and documentary filmmaking.
