Jason Calacanis: Greatest Angel Investor

  • 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.

Travel & Fee Range:**

  • Travels from: San Francisco, California
  • **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.

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 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.

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.

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.

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.

Contact us at Speakers Inc and follow us on Twitter

Jason Calacanis | Greatest Angel Investor

Videos

Interest to Book? Send us your enquiry

Speaker Contact Form

Enquiry Form

Talent resources available for download

In order to view the below you must be logged in.

  • Powerpoint Slide – For meeting and event planners
  • Gallery Images
  • High Resolution Images
  • PDF Files
  • Books and Magazine Links
  • Music List
  • Podcast Shows
  • Courses
  • + more

View further speakers

  • (22)
Chef Stephanie Izard

Chef Stephanie Izard is a culinary force to be reckoned with in the culinary world. With her innovative approach to cooking and an impressive list of accolades, she has earned a well-deserved reputation as a talented and influential chef. Her journey in the world of gastronomy has been marked by creativity, hard work, and a […]

  • Travels from: Chicago, IL
  • Chefs Speakers
  • (53)
Colonel Gregory Gadson

Colonel Gregory Gadson , a Chesapeake, Va., native; served our nation in the United States Army for more than 26 years. Col. Gadson’s service culminated as the Garrison Commander of Fort Belvoir, where he oversaw the daily operations of the post, a strategic sustaining base where more than 50,000 military personnel and employees provide logistical, […]

  • Travels from: Richmond, VA
  • Military Speakers
  • (43)
Kina Hart

Kina Hart’s professional journey is a powerful narrative of resilience, transformation, and unwavering commitment to workplace safety. The day that changed her life began unremarkably, much like any other workday. Yet, what unfolded was an unexpected workplace accident that left an indelible mark on her life. Now, Kina channels her experience into a potent message […]

  • Travels from: Ione, WA
  • Safety Speakers
  • (18)
Jessica Kriegel

Dr. Jessica Kriegel is a renowned workplace culture strategist, researcher, and speaker dedicated to transforming company cultures for business success. With a dynamic presence and an evidence-based approach, she has helped Fortune 100 companies, global brands, and industry leaders foster intentional cultures that drive performance, innovation, and employee engagement. Her expertise lies in decoding organizational […]

  • Travels from: Sacramento, CA
  • Culture Speakers
  • (63)
Eric Davis

One of the most exciting players of his generation, Eric Davis elicited comparisons to Willie Mays as the centerfielder for the Cincinnati Reds. From 1986 to 1990 he averaged 30 home runs and 40 stolen bases, won a pair of Gold Glove awards and led the Reds to a World Series victory in 1990. Injuries […]

  • Travels from: Phoenix, AZ
  • Sporting Speakers
  • (28)

Marco Tempest is an internationally renowned magician who blends illusion, technology, and storytelling to create unforgettable experiences. With a unique blend of expertise in both traditional magic and cutting-edge technology, Tempest has established himself as a pioneer in the field of techno-magic, captivating audiences at conferences, corporate events, and high-profile gatherings around the world. His work […]

  • Travels from: New York, NY
  • Motivational Speakers
  • (83)
Rawi Abdelal

Rawi Abdelal is recognized as one of the world’s foremost authorities on how globalization and geopolitics affect businesses, economies, supply chains and social structures Herbert F. Johnson Professor of International Management at Harvard Business School, faculty co-chair of the Bloomberg-Harvard City Leadership Initiative and faculty chair of the Harvard Business School/YPO Presidents’ Program Work focuses […]

  • Travels from: Cambridge, MA
  • Political Speakers
  • (23)
Dave Noll

Dave Noll is an Emmy Award-winning creative mastermind with a remarkable career spanning decades. His visionary contributions to the television and media industry have left an indelible mark. With over 60+ television series and an astonishing 3500+ episodes to his name, Dave’s portfolio is a testament to his unparalleled talent and unwavering dedication. Co-creating the legendary CHOPPED franchise, […]

  • Travels from: New York, NY
  • Celebrity Speakers
Disclaimer
The profiles and images embedded on these pages are from various conference entertainers and other talent.

These remain the property of its owner and are not affiliated with or endorsed by Speakers Inc.

Fee ranges where listed on this website are intended to serve as a guideline only.

All talent fees exclude VAT, travel and accommodation where required.

Subscribe to our Newsletter and get connected:

Your subscription could not be saved. Please try again.
Your subscription has been successful.

Newsletter

Subscribe to our newsletter and stay updated.

We use Brevo as our marketing platform. By submitting this form you agree that the personal data you provided will be transferred to Brevo for processing in accordance with Brevo's Privacy Policy.

Our Mission:

We are your partner creating memorable and engaging experiences that go beyond the event itself.

© All rights reserved 2025.  Designed using Voxel