Jason Calacanis is a prominent American entrepreneur, angel investor, and media personality, best known for his significant contributions to the startup ecosystem and his role in shaping the venture capital landscape. He rose to prominence as the founder of Silicon Alley Reporter and co-founder of Weblogs, Inc., which was acquired by AOL for $25 million. As an angel investor, Calacanis is celebrated for his early investments in companies like Uber, Robinhood, and Calm.
In addition to his work as an investor, Calacanis is a thought leader in the tech world, hosting the popular podcast This Week in Startups (TWIST), where he interviews entrepreneurs and venture capitalists. He is also the author of the book “Angel: How to Invest in Technology Startups”, offering insights into startup investing. Through his LAUNCH Accelerator and LAUNCH Festival, he continues to mentor and support the next generation of entrepreneurs.
Who is Jason Calacanis?
Jason Calacanis is a well-known American entrepreneur, angel investor, author, and podcast host. He has had a significant impact on the startup and technology industries, becoming one of the most influential figures in venture capital.Media Pioneer: Calacanis founded Silicon Alley Reporter, a tech publication covering the burgeoning New York City tech scene in the late 1990s. He also co-founded Weblogs, Inc., which was a network of blogs that included popular sites like Engadget. This network was acquired by AOL for approximately $25 million.Angel Investor: He is best known for being one of the earliest investors in Uber, which became one of the most successful startups in history. He has invested in numerous other successful companies, including Robinhood, Wealthfront, and Calm.
Jason Calacanis Net Worth
Jason Calacanis net worth is estimated to be around $100 million to $200 million, though the exact figure can fluctuate due to the success of his investments and ventures. A significant portion of his wealth comes from his early investment in Uber, which became one of the most valuable companies in the world. In addition to his investments in Uber, he has backed several other successful startups, including Robinhood, Calm, and Wealthfront. His role as an entrepreneur, particularly with Weblogs, Inc., which was acquired by AOL, also contributed to his wealth. As a prominent angel investor and founder of LAUNCH Accelerator, Calacanis continues to earn from his portfolio of tech investments while expanding his influence in the startup world.
Early Life and Education
Jason Calacanis was born and raised in Brooklyn, New York, where he developed an early interest in media, business, and technology. Growing up in a vibrant and competitive environment, he was exposed to the fast-paced nature of entrepreneurship and innovation from a young age.
He attended Xaverian High School, a private Roman Catholic school in Bay Ridge, Brooklyn, known for its strong academic programs and emphasis on leadership. During his time at Xaverian, Calacanis displayed a keen interest in communication, problem-solving, and networking—skills that would later prove invaluable in his career.
Following high school, he enrolled at Fordham University, a prestigious Jesuit institution in New York City. He pursued a degree in psychology, which provided him with insights into human behavior, decision-making, and interpersonal dynamics. His studies, combined with his natural curiosity and drive, helped him develop a deep understanding of consumer behavior—knowledge that later influenced his ventures in media, startups, and investing.
Although his academic background was rooted in psychology, Calacanis was deeply fascinated by the evolving landscape of the internet and digital media. This passion would later propel him into the world of technology startups, journalism, and venture capital, shaping his career as a prominent entrepreneur and investor.
Wiki
| Attribute | Details |
| Full Name | Jason Calacanis |
| Born | November 28, 1970 |
| Birthplace | Brooklyn, New York, USA |
| Education | Fordham University (Degree in Psychology) |
| High School | Xaverian High School |
| Profession | Entrepreneur, Angel Investor, Podcaster, Author |
| Notable Ventures | Silicon Alley Reporter, Weblogs, Inc., Mahalo, Inside.com |
| Major Investments | Uber, Robinhood, Thumbtack, Wealthfront, Calm |
| Podcast | This Week in Startups (TWIST) |
| Book | Angel: How to Invest in Technology Startups (2017) |
| Startup Programs | LAUNCH Accelerator, LAUNCH Festival |
| Industry Focus | Startups, Venture Capital, Tech Media |
| Notable Acquisition | Weblogs, Inc. sold to AOL for ~$25M |
Entrepreneurial Ventures
Jason’s journey as an entrepreneur began in the tech media space. He founded Rising Tide Studios, a media company that published online and print magazines focused on the technology industry. His Silicon Alley Reporter, a newsletter that expanded into a full-fledged magazine, gained prominence during the 1990s tech boom. However, the collapse of the dot-com bubble forced its closure, leaving Jason with financial setbacks.
Undeterred, he co-founded Weblogs, Inc. in 2003 alongside Brian Alvey. The blogging network gained traction quickly and attracted investors like Mark Cuban. In 2005, AOL acquired Weblogs, Inc. for $30 million, marking Jason’s first major financial success.
Venture Capital and Angel Investing
Following the sale of Weblogs, Jason took on roles in venture capital and tech investments. He briefly worked as the general manager at Netscape before joining Sequoia Capital as an Entrepreneur in Action.
In 2007, he launched Mahalo.com, a human-curated search engine backed by investors such as Sequoia Capital, Mark Cuban, and Elon Musk. Although it reached significant traffic milestones, a Google algorithm update in 2011 severely impacted its growth, leading to its closure in 2014.
Despite this setback, Jason shifted his focus to angel investing. His most notable investment was a $25,000 stake in Uber in 2009, when the company was valued at just $4 million. By the time Uber went public in 2019, his shares were worth an estimated $124 million on paper. He has also invested in startups like Thumbtack, UberMedia, Gowalla, and SignPost.
Podcasting and Public Influence
Jason has built a strong presence in the business podcasting space. Since 2009, he has hosted “This Week in Startups,” a widely followed podcast featuring discussions on tech entrepreneurship, venture capital, and emerging business trends.
In 2022, he joined Chamath Palihapitiya, David Sacks, and David Friedberg as a co-host of the “All-In Podcast,” where they discuss economic trends, technology, and finance.
Career
Jason Calacanis began his career in the technology and media industry during the early days of the internet boom in the 1990s. He initially worked as a technology journalist and entrepreneur, covering the rapidly growing digital space.
Journalism and Media Ventures
In the mid-1990s, Calacanis founded Silicon Alley Reporter, a print and online publication that covered the rise of the internet economy in New York City. The publication gained popularity for its in-depth coverage of startups, venture capital, and the tech industry, positioning Calacanis as a key figure in the Silicon Alley tech scene.
Silicon Alley Reporter eventually expanded but faced challenges following the dot-com bubble burst in the early 2000s. Calacanis later sold the publication and shifted his focus toward new media ventures.
In 2003, he became the general manager of Weblogs, Inc., a blog network he co-founded with Brian Alvey. The network, which included popular sites such as Engadget and Autoblog, became a major success. In 2005, Weblogs, Inc. was acquired by AOL for a reported $25 million, marking one of Calacanis’s first major exits.
Tech and Startup Investments
Following his success in media, Calacanis transitioned into angel investing and startup advising. In the late 2000s, he became CEO of Mahalo, a human-curated search engine designed to improve search results through expert-generated content. Despite initial success, Mahalo struggled to compete with Google’s algorithmic advancements and eventually pivoted into video content before shutting down.
Calacanis gained prominence in the startup ecosystem as an early investor in Uber, which became one of his most notable investments. He was an early advocate for the “angel investing” model, where individual investors provide funding to promising startups at their early stages.
In 2009, he launched This Week in Startups (TWIST), a podcast where he interviews founders, investors, and business leaders. The show became a must-listen for entrepreneurs and those interested in venture capital.
Launch of Inside.com and Angel Investing Success
In 2013, Calacanis founded Inside.com, a news aggregation and newsletter platform aimed at delivering high-quality, curated content on various industries.
In addition to his own ventures, he launched the LAUNCH Festival and LAUNCH Accelerator, programs designed to help startups refine their ideas, secure funding, and connect with investors. These initiatives further solidified his reputation as a mentor and connector in the startup world.
Through his angel investing firm, he has backed numerous successful startups, including Robinhood, Thumbtack, Wealthfront, and Calm. His investment strategy focuses on identifying high-growth companies at an early stage and providing them with guidance and funding.
Books and Thought Leadership
In 2017, Calacanis published “Angel: How to Invest in Technology Startups”, a book that provides insights into early-stage investing. The book became widely regarded as a valuable resource for aspiring angel investors.
As an outspoken and sometimes controversial figure, he frequently shares insights on tech trends, startup strategies, and investing through his podcast, social media, and speaking engagements.
FAQS
Q: Who is Jason Calacanis?
A: An entrepreneur, angel investor, author, and podcaster known for his role in the tech and startup world.
Q: What is Jason Calacanis net worth?
A: Estimated between $100 million and $200 million.
Q: What is his most notable investment?
A: His early investment in Uber.
Q: What is This Week in Startups?
A: A popular podcast hosted by Calacanis, focusing on startups and entrepreneurship.
Q: What is LAUNCH Accelerator?
A: A startup accelerator founded by Calacanis to help early-stage companies grow.
Conclusion
Jason Calacanis has built a reputation as a savvy investor, entrepreneur, and media personality. Despite facing ups and downs, his early bet on Uber and continued involvement in the tech world have solidified his status as a key figure in venture capital and startup culture.
Stay Connected and Alerts For More Updates. Pick Magazine
