We’ve seen many new entrepreneurs emerge as prominent figures in Silicon Alley and then disappear without a trace over the years. Rarely do we see someone like Jason Calacanis, who has retained his presence in the tech world for decades at this point.
During our research on Jason, we discovered multiple success stories such as his online blogging company Weblogs, Inc., which he sold for 25-30 million USD in 2005. Jason is also an angel investor (with a significant stake in Uber), as well as a podcast host with multiple successful podcasts on tech and business.
There is no denying that Jason Calacanis is a self-made millionaire. But just how rich is he? Join us as we analyze his most impactful projects and investments over the years in hopes of estimating his net worth. Let’s get started!
Early Life and Career Beginnings
The story of Jason Calacanis began in November of 1970, in the Bay Ridge section of Brooklyn, New York. From what we know, his parents were of Greek and Irish origin.
While little is publicly known about his early education, we do know that he graduated from Xaverian High School in 1988 and later received a Bachelor in Psychology from Fordham University.
Early entrepreneurship
We can find the sparks of entrepreneurship that later shaped Jason into the person we know today from his early life. During school he worked as a door-to-door salesman, selling books to the residents of New York. We even found reports of him picking up any gig that fell his way, like selling cookies.
Career beginnings
Jason’s career started in the 90s as a reporter at the New York Post. The primary focus of his journalism effort was directed towards the quickly growing internet sector. The internet at that time was vastly different from the endless collection of knowledge as we know it today.
During his job as a reporter, Jason also identified the lack of websites that aggregate news from around the web. This idea would later on inspire the creation of his first majorly successful venture; Weblogs.
Rise as a Tech Entrepreneur
As mentioned above, his experience as a reporter in the Internet sector led to the creation of Weblogs. But, there is another venture that came before that.
After moving on from his reporting job, Calacanis established a media company by the name of Rising Tide Studio. The primary business of this company was to publish both printed and online content.
Despite this being his first major venture, Rising Tide Studio was a decent success and put Jason’s name on the board.
From what we’ve seen, the thing that made him truly famous was the 1996 release of “Silicon Alley Reporter.” This was a 16-page newsletter that quickly grew into a 300-page magazine, documenting the progress of New York’s Silicon Alley.
We even found reports of Jason Calacanis being dubbed the “yearbook editor” by fans of this magazine. But, little did those fans know that this magazine was just the start of a decades-long media presence.
Ventures and Investments
So far, we’ve discussed the origin of Jason’s involvement in the tech media industry. Now let’s shift gears and talk about the major ventures that turned Calacanis into a self-made millionaire.
Weblogs
Calacanis co-founded Weblogs with fellow entrepreneur Brian Alvey in September of 2003. It was a blog network that published online content on a variety of topics, including tech, pop culture, video games, and even automobiles.
Initially, the company received capital from the angel investor Mark Cuban to get it off the ground. With the benefit of hindsight, this investment was a complete success. After just two years in the business, Weblogs was earning over 1,000 USD in revenue per day from Adsense alone.
This explosive growth put Weblogs on the radar of Time Warner's America Online which later acquired the company for 25-30 million USD in October of 2005. Unfortunately, we weren’t able to find the precise sum of this deal. That said, 30 million USD in 2005 is equivalent to over 47 million USD when adjusted for inflation.
After this acquisition, Jason worked at AOL (America Online) for another year as the CEO of Weblogs — retiring in November 2006.
Uber
After retiring from Weblogs, Jason would join EIA (entrepreneur in action), a venture capital firm that would lead to his most successful investment to date. During his time with this firm, Calacanis would invest 25,000 USD into Uber. Yes, the Uber that many of you use on a frequent basis to order food and get around town.
According to our findings, today this relatively small investment of 25,000 USD is worth more than 100 million USD. That is an investment turnover of nearly 400,000%.
Other investments and ventures
While the creation of Weblogs and the investment in Uber are the crown jewels of Jason Calacanis’ impressive career, they are far from his only successes. After some in-depth research, we also uncovered a number of other involvements from Calacanis in the world of tech and online media.
In 2007, for example, Jason launched a web directory called Mahalo.com. This received up to 20 million USD in venture capital from well-known investors such as CBS, Mark Cuban, and Elon Musk. At its peak, the company was receiving 15 million unique visitors each month.
In the same year, Jason also launched Inside.com — a topical newsletter company that received over 2.6 million USD in investment. According to our research, this newsletter had over 750,000 subscribers at its peak.
Other than that, we also found reports of Jason’s investments in companies such as Evernote and Thumbtack. However, we were unable to find any specifics of his involvement in these ventures.
Media Presence and Public Influence
The focus of this article till now has been on Jason Calacanis’ successful investments and ventures. However, that is only a part of what makes Jason such a recognizable figure in the tech and media world. The other key reason behind his influence is his podcasts. These include:
This Week in Startups
This Week in Startups is Calacanis’ most well-known podcast and for a good reason. It was announced back in March of 2009 through a blog post and officially started in May of the same year.
As its name suggests, This Week in Startups is a weekly podcast for any and every topic relating to tech, business, online media, and new promising startups. The best part about this podcast is that it’s still going strong after more than 14 years. In fact, the current episode count is 1,847 at the time of writing.
Given its long history, This Week in Startups has amassed a significant loyal audience over the years. We gave a few of the latest episodes a listen and the information offered in this podcast is truly insightful for both new and veteran entrepreneurs.
All-In
Compared to “This Week in Startups,” All-In is a relatively new podcast as it launched in May of 2022.
From what we can gather, this is also a tech and business-focused podcast. But, the thing that differentiates All-In from “This Week in Startups” is that Jason is not the only host of this podcast. Instead, he co-hosts every episode with David O. Sacks, Chamath Palihapitiya, and David Friedberg — all successful entrepreneurs and venture capitalists in their own right.
Estimating Jason Calacanis’s Net Worth
While we aren’t even close to covering every noteworthy aspect of Jason Calacanis’ life, we have successfully touched on the most prominent aspects. With that in mind, it’s time for the big question. What is Jason Calacanis’s net worth?
According to our estimation, Jason Calacanis’ net worth is anywhere between 150 and 200 million USD. For those waiting for a concrete answer, this large gap of 50 million USD might be a bit disappointing. Unfortunately, this is as close as we can get within reason.
The thing about Jason’s earnings is that — aside from the Uber equity — a significant portion of it is tied to the popularity of his podcasts and his personal brand as a tech and business influencer.
Jason’s earnings from investments in companies like Evernote and Thumbtack are also not publicly available. So, for all intents and purposes, he could own assets surpassing 200 million USD with ease, but we have no way of confirming it.
That said, a net worth between 150 and 200 million USD is the most likely according to our research and estimation.
Philanthropy and Personal Interests
During our research, looking into Calacanis’ personal interests outside of tech and business yielded no meaningful return. He has always kept a low profile and doesn’t share much about his personal life in his podcasts either.
As for his philanthropic efforts, one venture caught our attention immediately — Founder University.
In essence, it is a 12-week-long program designed to help young entrepreneurs find their footing in the world of business. The initial tuition fee for this course is 500 USD, which doesn’t sound very philanthropic.
However, if you manage to become one of the top graduates, you will get your 500 USD fee back. Not only that, but the university — led by Jason — will also invest 25,000 USD in your business to help you grow faster.
Conclusion
To summarize, Jason Calacanis’ life is one of infatuation with online media and becoming a pioneer in the online blogging space with Weblogs. His investment in Uber is also a testament to his keen sense of potential as a businessman.
We would, however, argue that his most significant contribution to the world at large is his dedication to an informative, business and tech-focused podcast for more than 14 years. All-in-all, Jason’s story is a testament to budding entrepreneurs that you also have a chance to make it big.