When discussing influential entrepreneurs and angel investors in the tech industry, the name Jason Calacanis inevitably comes up. As a prominent figure with a diverse career path, Jason’s education has played a significant role in shaping his success. In this in-depth article, we will explore the foundations of Jason Calacanis’ education, how it has influenced his career, and the lessons aspiring entrepreneurs can learn from his journey.

jason calacanis education

Early Life and Education

Born on November 28, 1970, in Brooklyn, New York, Jason McCabe Calacanis spent his childhood in the Bay Ridge neighborhood. His parents, John and Linda Calacanis, were of Greek and Irish descent, and both worked hard to provide for their family. This upbringing instilled a strong work ethic in Jason from an early age, which would later contribute to his accomplishments.

Jason Calacanis’ education began in public schools, including P.S. 185 and P.S. 104, before he went on to attend Xaverian High School. As a private Catholic school, Xaverian provided him with a solid foundation in academics and discipline, which would influence his work ethic and approach to business.

After high school, Jason was accepted into Fordham University, a prestigious private research institution in New York City. He majored in psychology, a field that has since informed his understanding of human behavior and decision-making. This knowledge has proven invaluable in his entrepreneurial journey, enabling him to build successful businesses and make sound investment decisions.

Professional Beginnings

Upon graduating from Fordham University, Jason Calacanis began his career as a writer and journalist. He founded the New York City-based magazine, “Silicon Alley Reporter,” in 1996. This publication was dedicated to covering the emerging tech scene in the city and helped establish Jason as a prominent voice in the industry.

Jason Calacanis’ education in psychology also played a pivotal role in his next business venture, Weblogs, Inc. In 2003, he co-founded the company with Brian Alvey, tapping into the growing trend of blogging as a form of online communication. By understanding the motivations behind why people share their thoughts and experiences online, Jason and his team were able to create a successful blog network that attracted millions of readers.

Weblogs, Inc. was eventually acquired by AOL in 2005, which catapulted Jason Calacanis into the limelight as a respected entrepreneur and angel investor. This marked the beginning of his prolific career in investing and advising startups.

Angel Investing and Entrepreneurial Success

As an angel investor, Jason Calacanis has made numerous successful investments, with over 200 startups in his portfolio. Some of his most notable investments include Uber, Tumblr, and Evernote. His keen understanding of human behavior, coupled with his experience in entrepreneurship, has helped him identify promising startups and support their growth.

In addition to his investment activities, Jason has also co-founded several other companies, including Mahalo, a human-powered search engine, and Inside, a mobile news app. His diverse educational background in psychology and journalism has been a key driver in the success of these ventures, as he can effectively analyze market trends and consumer preferences.

Contributions to Education and Mentorship

Given the crucial role education has played in Jason Calacanis’ career, it is no surprise that he is an advocate for education and mentorship. He has shared his knowledge and experience with aspiring entrepreneurs through various platforms, including his podcast, “This Week in Startups,” and his book, “Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000.”

In his podcast, Jason interviews successful entrepreneurs, venture capitalists, and other industry experts, providing valuable insights and advice to listeners. His book, “Angel,” offers practical guidance on how to navigate the world of angel investing and identifies the key factors that contribute to a startup’s success. By sharing his knowledge and experiences, Jason is giving back to the entrepreneurial community and helping to shape the next generation of business leaders.

Jason has also been involved in various initiatives that promote education and mentorship. He is an active speaker at tech conferences and events, such as TechCrunch Disrupt and Launch Festival, where he imparts his wisdom and engages with aspiring entrepreneurs. Additionally, Jason has participated as a guest lecturer at universities, sharing his insights on entrepreneurship, investing, and the tech industry with students.

Lessons from Jason Calacanis' Education

There are several key takeaways from Jason Calacanis’ education that aspiring entrepreneurs can learn from:

  1. Leverage your educational background: Jason’s degree in psychology provided him with a unique perspective on human behavior, which has been instrumental in his entrepreneurial and investing endeavors. Embrace your academic background and consider how it can inform your approach to business and investment decisions.

  2. Embrace lifelong learning: Jason’s continuous pursuit of knowledge, as evidenced by his podcast and participation in industry events, highlights the importance of staying informed and adapting to the ever-changing business landscape. Aspiring entrepreneurs should commit to ongoing personal and professional development.

  3. Value mentorship and networking: Jason’s success as an entrepreneur and investor can be partially attributed to the strong relationships he has built within the tech community. Seek out mentors, advisors, and peers who can support and guide you on your entrepreneurial journey.

  4. Give back to the community: Jason’s commitment to sharing his knowledge and experience with others demonstrates the value of giving back. Aspiring entrepreneurs can contribute to the broader entrepreneurial ecosystem by mentoring, investing in, or advising other startups.


Jason Calacanis’ education has played an essential role in shaping his successful career as an entrepreneur and angel investor. His background in psychology has provided him with unique insights into human behavior, which has informed his business and investment decisions. Aspiring entrepreneurs can learn valuable lessons from his educational journey, including the importance of leveraging one’s educational background, embracing lifelong learning, valuing mentorship, and giving back to the community. By understanding and applying these lessons, the next generation of business leaders can cultivate their success in the ever-evolving world of entrepreneurship and technology.