Jason Calacanis

Tagline: Greatest Angel Investor

Talent Highlights

  • Advisor to Elon Musk, Executive at Twitter. Greatest Angel Investor & Bestselling Author. Host of This Week In Startups
  • Jason Calacanis is a member of the trusted inner circle for Elon Musk and possibly the next CEO of Twitter.
  • Jason authored the best-selling book Angel: How to Invest in Technology Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000.
  • Calacanis has invested in over 300 early-stage startups including several that have achieved billion-dollar valuations, including Uber and Thumbtack.
  • He is also host of the business podcasts All-In and This Week in Startups, which was featured in the Fortune article “The Ultimate Guide to the Best Business Podcasts.”

Keynote Topics

  • What does it take to create a successful tech company?
  • And how do you know if a tech company is worth investing in?

From the dot.com boom to his top podcast This Week in Startups, Jason has been an observer of what it takes to succeed in Silicon Valley.

He has invested in over 300 companies, with several of them being valued at over 1 billion dollars.

In this talk based on his career as an angel investor, Jason will share the cold hard lessons of Silicon Valley: what works, what doesn’t, when to dive in, and when to cut your losses.

In this fireside chat with Jason Calacanis, audiences will dive deep into the world of Silicon Valley, tech companies, and angel investing.

Jason shares stories about his journey from tech company creator to tech company angel investor. Learn the secrets of Silicon Valley and the process Jason uses to evaluate tech companies and their founders when investing.

Travels from:

  • San Francisco, CA

Fee Range:

  • Fees* $75,001 - $100,000




Jason Calacanis is a prominent figure in the technology and startup ecosystem, renowned for his success as an angel investor, entrepreneur, and thought leader in the tech industry. His influence as a top business speaker and tech visionary has made a substantial impact on the world of startups and venture capital. Jason Calacanis is a […]

Jason Calacanis is a prominent figure in the technology and startup ecosystem, renowned for his success as an angel investor, entrepreneur, and thought leader in the tech industry. His influence as a top business speaker and tech visionary has made a substantial impact on the world of startups and venture capital.

Jason Calacanis is a top business speaker and tech thought leader known as the “greatest angel investor.” His book Angel: How to Invest in Technology Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 was an Audible bestseller. And his podcast This Week in Startups was featured in the Fortune article “The Ultimate Guide to the Best Business Podcasts.”

Proclaimed “arguably the world’s greatest angel investor” by The Twenty Minute VC, Calacanis has invested in over 300 early-stage startups. Several have achieved billion-dollar evaluations, such as Uber, Robinhood, Trello, and Calm (the meditation app).

Jason got his start in angel investing with the top-tier, venture-capital firm Sequoia Capital. While working as a scout, Jason’s invested $25,000 in Travis Kalanick’s company, Uber, which is now worth around $100 million.

Jason Calacanis | Greatest Angel Investor

Weblogs, Inc.: A Pioneering Venture

Jason Calacanis is perhaps best known for co-founding Weblogs, Inc. in 2003, a company that would later become a major player in the blogging and online media landscape. Weblogs, Inc. was one of the first companies to create a network of professionally edited blogs covering a wide range of topics. The company’s success and eventual acquisition by AOL in 2005 marked a significant milestone in the evolution of digital media.

Angel Investing and Venture Capital

Calacanis is often referred to as the “greatest angel investor” due to his early investments in a number of now-iconic startups. Some of his notable investments include:

  • Uber: Calacanis was an early investor in Uber, the ride-sharing giant that has revolutionized the transportation industry.
  • Thumbtack: He invested in Thumbtack, an online marketplace that connects consumers with local service professionals.
  • Robinhood: Calacanis also backed Robinhood, the fintech company that popularized commission-free stock trading.
  • Trello: He was an early investor in Trello, a project management tool that was later acquired by Atlassian.
  • Calm: Calacanis invested in Calm, a meditation and sleep app that has gained immense popularity.
  • Inside.com: He founded Inside.com, a news aggregation service that aims to provide concise and informative news briefs.

Jason Calacanis knack for identifying and supporting successful startups has earned him a reputation as an astute angel investor. His investments have not only been financially rewarding but have also contributed to the growth of innovative companies that have reshaped industries.

Thought Leadership and Speaking Engagements

In addition to his accomplishments as an entrepreneur and investor, Jason Calacanis has established himself as a sought-after business speaker and tech thought leader. He frequently shares his insights and expertise at conferences, webinars, and podcasts. His thought leadership covers a wide range of topics, including entrepreneurship, angel investing, the tech industry, and startup strategies.

Controversial and Candid Style

Jason Calacanis is known for his candid and sometimes controversial style. He doesn’t shy away from expressing strong opinions and engaging in debates, making him a polarizing figure in the tech and business communities. His willingness to challenge conventional wisdom and provoke discussion has contributed to his influence as a thought leader.


Jason Calacanis’s journey from a young entrepreneur to a top business speaker and angel investor underscores the dynamic nature of the tech industry. His contributions to the world of startups, digital media, and angel investing have left an indelible mark. Calacanis continues to be a prominent voice in the tech and business world, offering insights, investing in promising startups, and sharing his experiences with audiences eager to learn from one of the industry’s most influential figures.

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