The Life and Times of Jason Calacanis: A Biography

Jason Calacanis giving the peace sign.

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The Life Story of Jason Calacanis

When discussing angel investors and businesspeople, Jason Calacanis is commonly mentioned.

Calacanis got involved in several ventures, creating his own businesses or investing in just the right ones.

Calacanis is a man that saw potential in various businesses and made his fortune out of it. Even though he has a net worth in the millions, he is not as well-known as other investors.

However, his fortune has grown steadily and quickly over the past few years, showing his potential. In this article, we will talk more about Jason Calacanis and how he came to be so successful.

 

“When I was coming up as an entrepreneur, I had to fight for everything I got, and there was no clear roadmap of how to be successful.” ~  Jason Calacanis

 

Early Life and Background

Calacanis had a very good start in life, which later added to his success. Born on November 28, 1970, in Bay Ridge, New York, Calacanis was surrounded by entrepreneurs for most of his life. His parents were of Irish and Greek origin, and thanks to their encouragement and support, Calacanis obtained a good education.

He graduated in 1988 from Xaverian High School, continuing his education at Fordham University with a bachelor’s in psychology. That degree helped him understand people, and he used his ideas to set up his own business.

Growing up, he valued hard work and knowledge. As a result, he laid down the foundation for his entrepreneurial success from the moment he finished college.

However, before that, he dabbled in various ventures that would bring him some experience. During school, he began working selling books to New Yorkers door-to-door. He would also pick up the occasional job, such as selling cookies.

“Imagine being 30 years old, thinking you were a media titan, and now you are labeled a ‘scam artist.'” ~  Jason Calacanis

 

Early Career

After graduating from college, Calacanis entered the workforce and began his professional journey. He obtained jobs that gave him the foundation and insights necessary for his eventual triumph in the tech industry.

His initial employment was at Starwave Corporation, a technology startup. Although his tenure there was relatively short, this experience laid the groundwork for his future accomplishments.

Calacanis’s career kicked off in the 1990s when he worked as a reporter in New York, focusing primarily on the Internet sector. While at the New York Post, he identified the lack of a single website aggregating news. This observation sparked the idea for Weblogs.

Subsequently, Calacanis established Rising Tide Studio, a media company he founded to publish online and printed materials. The platform achieved considerable success, leading to Calacanis being endearingly referred to as the “yearbook editor” by the Silicon Valley community.

The Rise of Weblogs Inc. and Calacanis’s Ascend to Fame

Calacanis laid the foundation for Weblogs Inc., the company that would eventually skyrocket him to fame, on September 24, 2003. He co-founded this company alongside Brian Alvey, with financial backing from angel investor Mike Cuban.

Weblogs generated more than $2,000 per day from AdSense. The company was sold to America Online, led by Time Warner, in 2005, with Calacanis receiving over 25 million dollars. He was still the CEO for one more year, and in 2006, he resigned.

 

“I don’t want someone taking half a sentence or paraphrasing me… Just too much risk.” ~  Jason Calacanis

 

Angel Investing and Venture Capital

Aside from his journaling interest, Calacanis also began gaining more interest in venture capitalism. In 2006, after quitting Weblogs, he joined Sequoia Capital, a famous venture capital company. He was their EIA (entrepreneur in action), a position he would maintain until 2007.

During his time at Sequoia, Calacanis invested approximately $25,000 in Uber, the company founded by Travis Kalanick. Initially, the value of the company was not substantial. However, as time passed, the deal escalated to over $100 million, ultimately yielding a significant return on Calacanis’s investment.

In 2007, Jason Calacanis launched Mahalo, which means “thank you” in Hawaiian. This web directory would raise about $20 million in venture capital from numerous investors, including Elon Musk, Mark Cuban, CBS, News Corp, Sequoia Capital, and more.

The company peaked at around 15 million visitors, obtaining maximum profitability in 2011. However, the company steadily declined after the Google Panda search algorithm update that year. Eventually, Mahalo shut down its business in 2014.

Aside from Mahalo, Calacanis also laid the foundations for ThisWeekIn.com. The company temporarily shut down in 2012 but returned a few years later. It is now available to be heard as a weekly podcast.

 

“There’s nobody who has as big of a real-time logistics network than Uber.” ~  Jason Calacanis

 

Personal Life

While the exact date is unknown, Calacanis is married to Jade Li. The couple prefers to keep a low profile on their personal life, and we only know that they tied the knot somewhere around 2006-2009.

Aside from a few pictures on Instagram, we do not know much about his wife. The couple does have a daughter, as people were able to see from his Instagram posts.

Calacanis also has a brother with whom he spent most of his childhood, although little is known about him. He sparked controversy due to an association with Jeffrey Epstein after his name appeared in Epstein’s Black Book.

Calacanis denied any close connection aside from a Ted Talk conversation. He also admitted to a casual ping pong game with Epstein’s alleged accomplice, Ghislaine Maxwell.

Current and Future Endeavors

Calacanis has quite a few regular endeavors nowadays. He founded This Week in Startups, a TV show that Calacanis began co-hosting with Molly Woods. In 2023, Woods left the show, giving no specific reason. Calacanis became in charge of This Week in Startups.

Calacanis is also the founder of Inside.com, which offers thematic newsletters. The company eventually raised more than $2.6 million through its publishing. Calacanis also partnered with the NSW government, creating the Sydney Launch Festival, where startups can find investors.
Impact and Legacy

Calacanis has passed some fairly impressive milestones throughout his life. Many were yearly awards, but he also received an award that would last him a lifetime. This was the Henry Bloch Award for Lifetime Achievement in 2017, where he was recognized for his accomplishments. The award would also acknowledge his ability to create opportunities for others.

Calacanis impacted various businesses that would not have been such a success without his involvement. He was among the first investors in companies such as Uber, Evernote, and Thumbtack. He saw potential in many companies, however small, and his involvement allowed them to succeed.

Moreover, Calacanis wanted to help young investors, not just the business owners. As a result, he wrote a book called “Angel: How to Invest in a Technology Startup.” This would gain him even more respect and recognition in the world of business.

 

“For three or four decades, we’ve been sitting here in front of this TV consuming a one-way medium that we had no control over.” ~  Jason Calacanis

 

Conclusion

With a keen eye for potential, Jason Calacanis created a fortune through hard work and smart decisions. Not only did he succeed in his own business, but he also helped numerous other businesses achieve success. Without his involvement, there is no saying what would have happened with multinational companies such as Uber. His hard work made him an example for business owners and investors alike.

Key Points

  • Jason Calacanis is a successful angel investor and entrepreneur who has built a fortune in millions.
  • Born on November 28, 1970, in Bay Ridge, New York, Calacanis had an entrepreneurial upbringing and a strong education.
  • After graduating from Fordham University with a bachelor’s in psychology, he began his career at Starwave Corporation, a technology startup.
  • He made significant strides in the 1990s, working as a reporter focusing on the Internet sector, and later founded Rising Tide Studio, a media company.
  • Calacanis’s fame rose when he co-founded Weblogs Inc. with Brian Alvey in 2003. The company was sold to America Online in 2005 for over 25 million dollars.
  • Post-Weblogs, he joined Sequoia Capital as their EIA (entrepreneur in action) and invested approximately $25,000 in Uber, which later escalated to over $100 million.
  • In 2007, Calacanis launched Mahalo, a web directory that raised about $20 million in venture capital. However, the company shut down in 2014 after the Google Panda search algorithm update.
  • He founded ThisWeekIn.com, now available as a weekly podcast, and Inside.com, a thematic newsletter company.
  • Calacanis is married to Jade Li, and the couple has a daughter.
  • He is currently in charge of This Week in Startups, a TV show, and has partnered with the NSW government to create the Sydney Launch Festival.
  • Calacanis was awarded the Henry Bloch Award for Lifetime Achievement in 2017 and has written a book titled “Angel: How to Invest in a Technology Startup.”
  • Not only has he built his own successful businesses, but Calacanis has also invested in and supported various others, including Uber, Evernote, and Thumbtack.

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Timeline.Jason Calacanis

November 28, 1970:

Jason Calacanis is born in Bay Ridge, New York.

1988:

Calacanis graduates from Xaverian High School.

Early 1990s:

Calacanis begins his career as a reporter in New York, primarily focusing on the Internet sector. Around this time, he also starts working for Starwave Corporation, a technology startup.

Late 1990s:

Calacanis establishes Rising Tide Studio, a media company that publishes online and printed materials.

September 24, 2003:

Calacanis co-founds Weblogs Inc. with Brian Alvey.

2005:

Weblogs Inc. is sold to America Online (Time Warner), resulting in Calacanis receiving over 25 million dollars.

2006:

Calacanis resigns as CEO of Weblogs Inc. and joins Sequoia Capital as an entrepreneur in action (EIA). During this year, he also invests approximately $25,000 in Uber. He also gets married to Jade Li, the exact date is between 2006 and 2009.

2007:

Calacanis launches Mahalo, a web directory. He also leaves Sequoia Capital this year.

2011:

Mahalo, Calacanis’s company, reaches its peak profitability.

2012:

Calacanis’s ThisWeekIn.com temporarily shuts down.

2014:

Mahalo shuts down its business.

2017:

Calacanis receives the Henry Bloch Award for Lifetime Achievement.

Unknown year post-2012:

ThisWeekIn.com returns as a weekly podcast.

2023:

Calacanis becomes the sole host of This Week in Startups after co-host Molly Woods leaves the show.

Throughout his career, Calacanis also invests in various businesses, notably being among the first investors in companies such as Uber, Evernote, and Thumbtack. Additionally, he pens a book titled “Angel:

How to Invest in a Technology Startup,” aimed at assisting young investors.

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Life Lessons

  1. Recognizing potential in various businesses:
    Calacanis had a knack for identifying potential in different ventures and making successful investments. This teaches us the importance of spotting opportunities and having the confidence to pursue them.
  2. The value of hard work and knowledge:
    Calacanis valued hard work and knowledge from a young age, which laid the foundation for his success. This highlights the significance of continuous learning, dedication, and putting in the necessary effort to achieve goals.
  3. Gaining experience through diverse ventures:
    Before finding his niche, Calacanis gained valuable experience through various ventures, such as selling books and cookies. This teaches us that diverse experiences can contribute to our skill set and provide insights that may be beneficial in future endeavors.
  4. Seizing opportunities in emerging industries:
    Calacanis recognized the potential of the internet and emerging technologies, which led him to establish successful companies like Weblogs Inc. and invest in startups like Uber. This emphasizes the importance of being adaptable and proactive in identifying and capitalizing on trends and emerging markets.
  5. The power of networking and partnerships:
    Calacanis formed strategic partnerships and gained financial backing from notable investors, which played a significant role in the success of his ventures. This teaches us the value of building relationships, seeking mentorship, and leveraging networks to foster growth and opportunities.
  6. Embracing entrepreneurship and resilience:
    Calacanis demonstrated the entrepreneurial spirit by founding and leading multiple businesses. Despite facing challenges and setbacks, such as the decline of Mahalo after a major algorithm update, he continued to adapt and explore new opportunities. This teaches us the importance of resilience, adaptability, and a willingness to learn from failures.
  7. Sharing knowledge and giving back:
    Calacanis wrote a book and hosted a TV show to share his experiences and insights with aspiring entrepreneurs and investors. This highlights the significance of giving back to the community, mentoring others, and sharing knowledge for the collective growth and success of the industry.
  8. Recognizing achievements and leaving a legacy:
    Calacanis received awards and recognition for his accomplishments, including the Henry Bloch Award for Lifetime Achievement. This teaches us the importance of acknowledging and celebrating milestones while striving to create a positive and lasting impact in our chosen fields.

Overall, the life story of Jason Calacanis offers valuable lessons on entrepreneurial mindset, seizing opportunities, networking, resilience, and giving back to the community. These lessons can inspire and guide individuals pursuing their own business ventures or seeking success in the world of investments.

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Facts

  1. Jason Calacanis is commonly mentioned when discussing angel investors and businesspeople.
  2. Calacanis got involved in several ventures, creating his own businesses or investing in others.
  3. He saw potential in various businesses and made his fortune out of it.
  4. Calacanis has a net worth in the millions.
  5. His parents were of Irish and Greek origin and supported his education.
  6. Calacanis obtained a bachelor’s degree in psychology from Fordham University.
  7. Before starting his own business, he worked selling books and cookies.
  8. Early in his career, Calacanis worked at Starwave Corporation, a technology startup.
  9. He worked as a reporter in New York in the 1990s, focusing on the Internet sector.
  10. Calacanis identified the lack of a single website aggregating news, leading to the idea for Weblogs Inc.
  11. He co-founded Weblogs Inc. on September 24, 2003, with Brian Alvey.
  12. Weblogs Inc. was sold to America Online in 2005 for over $25 million.
  13. Calacanis joined Sequoia Capital as an entrepreneur in action (EIA) in 2006.
  14. He invested approximately $25,000 in Uber and achieved a significant return on his investment.
  15. Calacanis launched Mahalo, a web directory, in 2007, raising about $20 million in venture capital.
  16. He also founded ThisWeekIn.com and later turned it into a weekly podcast.
  17. Calacanis is married to Jade Li and they have a daughter.
  18. Calacanis received the Henry Bloch Award for Lifetime Achievement in 2017.
  19. He was among the first investors in companies like Uber, Evernote, and Thumbtack.
  20. Calacanis wrote a book called “Angel: How to Invest in a Technology Startup.”
  21. He founded This Week in Startups and is the founder of Inside.com.
  22. Calacanis partnered with the NSW government to create the Sydney Launch Festival.

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Questions and Answers

The information in this post answers many of the questions about Jason Calacanis. In addition, this section provides a summary and any further information.

Sure, here are some questions based on the text provided:

  1. Who is Jason Calacanis?
    • Jason Calacanis is a prominent angel investor and businessman known for his significant success in the tech industry.
  2. Where and when was Jason Calacanis born?
    • Jason Calacanis was born on November 28, 1970, in Bay Ridge, New York.
  3. What did Jason Calacanis study in college?
    • Calacanis graduated from Fordham University with a bachelor’s degree in psychology.
  4. What was Calacanis’s first job after college?
    • His first job after college was at Starwave Corporation, a technology startup.
  5. What was Jason Calacanis’s significant career breakthrough?
    • His major career breakthrough came when he co-founded Weblogs Inc., which was later sold to America Online for over 25 million dollars.
  6. How did Jason Calacanis start his journey into venture capitalism?
    • After leaving Weblogs Inc., he joined Sequoia Capital as an Entrepreneur in Action and began to invest in startups like Uber.
  7. What was Jason Calacanis’s biggest investment success?
    • His investment in Uber, initially $25,000, escalated to over $100 million, marking his most significant success.
  8. What is Mahalo, and what happened to it?
    • Mahalo was a web directory launched by Calacanis in 2007, but it eventually shut down its business in 2014 after the Google Panda search algorithm update.
  9. Who is Jason Calacanis’s wife, and when did they get married?
    • Jason Calacanis is married to Jade Li, though the exact date is unknown; they tied the knot somewhere around 2006-2009.
  10. What is Jason Calacanis’s current venture?
  • He is currently involved with This Week in Startups and Inside.com, and he also partnered with the NSW government to create the Sydney Launch Festival.
  1. What are some of Jason Calacanis’s notable accomplishments?
  • Apart from his successful investments and companies, Calacanis has been awarded the Henry Bloch Award for Lifetime Achievement in 2017 and has written a book titled “Angel: How to Invest in a Technology Startup.”
  1. What impact has Jason Calacanis had on the tech industry?
  • Calacanis’s keen eye for potential has not only brought him success but has also facilitated the success of many businesses, including companies like Uber, Evernote, and Thumbtack. His investment strategies and insight have made him a valuable figure in the business world.

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