Jason Calacanis: Greatest Angel Investor

    Technology keynote speaker, angel investor, and entrepreneur Jason Calacanis helps founders and business leaders build innovative startups, scale companies, and invest in breakthrough technologies.

    Jason Calacanis - Image 02 (June 25, 2026)

    Quick Facts:

      • International keynote speaker on entrepreneurship and technology
      • Angel investor in more than 300 early-stage startups
      • Early investor in Uber, Robinhood, Trello, and Calm
      • Co-founder of Weblogs, Inc., acquired by AOL
    • Formats:
    • Keynote Speaker | Entrepreneur | Angel Investor

    • Audiences:
    • Entrepreneurs, startup founders, venture capital firms, executives, innovation teams, technology organizations, investors, universities, and business conferences.

    • Outcomes:
      1. Learn how successful startups identify opportunities and achieve sustainable growth.
      2. Understand the fundamentals of angel investing, fundraising, and venture capital.
      3. Gain practical insights into innovation, emerging technologies, and entrepreneurial leadership.
    Reading time: 5 min
    Reviews: (0 reviews)
    • Travels from: San Francisco, CA
    • **Fee range: $75,001 - $100,000

    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.

    Talent Short Bio

    Jason Calacanis is one of the world’s most influential angel investors, technology entrepreneurs, startup advisors, and keynote speakers. Renowned for identifying transformational companies at their earliest stages, Jason has invested in more than 300 startups, helping founders build category-defining businesses while shaping the modern technology ecosystem.

    Widely recognized as one of Silicon Valley’s leading early-stage investors, Jason’s portfolio includes companies such as Uber, Robinhood, Trello, and Calm. His investment philosophy, entrepreneurial experience, and deep understanding of startup growth have made him one of the most respected voices in venture capital, innovation, and technology.

    Jason began his entrepreneurial journey by co-founding Weblogs, Inc., one of the pioneering professional blogging networks. The company’s successful acquisition by AOL helped redefine digital publishing and established Jason as an influential entrepreneur during the early evolution of online media. He later expanded his impact through startup investing, founder mentoring, and technology education.

    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 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.

    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.

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