Jason Calacanis is an American Internet entrepreneur and angel investor who has had his fair share of success when it comes to online businesses. After selling Weblogs Inc to AOL for around $30 million, Jason worked with Sequoia Capital before creating the Mahalo web directory, which received funding from the likes of Elon Musk and Mark Cuban.
Since then, Jason has made investments in several companies including Uber, Thumbtack and Tumblr. He’s also picked up some valuable domain names along the way. Here are our top five in no particular order.
ADay.com
Aside from being a memorable four-letter .COM, ADay.com could be considered as an excellent brandable domain name for a startup, or another venture that Jason may consider in the future. The domain is currently dormant, but Jason likely had a plan for it at some point in time. Should he ever choose to sell the domain, there are several potential suitors for the name including A Day, a New York based fashion company using the insipid ThisIsADay.com.
20.com
In 2006, Jason purchase 20.com for $75,000. At the time, that could be considered a fair amount to pay for a two-number .COM domain name. Fast forward to 2017 and it is a seven-figure name. In fact, Jason revealed that he has turned down several seven figure offers including a $3.4 million bid. In a NamePros interview, Jason told us that he initially wanted to start a Wikipedia-like search engine, where consumers could rank the top twenty links for a given subject.
Jason also revealed that he received twenty emails per week regarding the domain name, but none of the offers have motivated the angel investor to sell. Currently, the name holds a mailing list through which potential buyers can submit their information.
Annotated.com
Jason has owned this one-word .COM domain name for many years after almost starting a company based around the name. A 2008 edition of Jason’s newsletter revealed that he bought annotated.com after being inspired by the concept of Third Voice, a controversial web annotation service that allowed users to comment on a website in a sidebar, thanks to a browser plug-in.
The company never materialised, and the name now forwards to Calacanis.com, Jason’s personal blog.
Inside.com
This domain name was acquired by Jason from domain investor John Quail for a reported $90,000. Inside.com has housed a couple of incarnations since Jason bought the name. Initially, Inside.com was developed as a news app in 2014, which used human curation to help readers discover the best coverage. Since then, Jason’s company has moved to email newsletters, offering many specific newsletters that are sent out periodically to thousands of subscribers.
Mahalo.com
At the start of this article, we mentioned that Jason launched Mahalo. Given Jason’s history of using high quality .COM domains, Mahalo.com was always the preferred domain. Mahalo.com was created in 2007 and increased in traffic from 10,000 visitors per month to two million per month in January 2008. According to Wikipedia, Jason stated in 2014 that Google Panda updates were “killing” Mahalo, which once had $10 million in yearly advertising revenue.
Now, Mahalo is a part of Jason’s Inside.com network.
Since then, Jason has made investments in several companies including Uber, Thumbtack and Tumblr. He’s also picked up some valuable domain names along the way. Here are our top five in no particular order.
ADay.com
Aside from being a memorable four-letter .COM, ADay.com could be considered as an excellent brandable domain name for a startup, or another venture that Jason may consider in the future. The domain is currently dormant, but Jason likely had a plan for it at some point in time. Should he ever choose to sell the domain, there are several potential suitors for the name including A Day, a New York based fashion company using the insipid ThisIsADay.com.
20.com
In 2006, Jason purchase 20.com for $75,000. At the time, that could be considered a fair amount to pay for a two-number .COM domain name. Fast forward to 2017 and it is a seven-figure name. In fact, Jason revealed that he has turned down several seven figure offers including a $3.4 million bid. In a NamePros interview, Jason told us that he initially wanted to start a Wikipedia-like search engine, where consumers could rank the top twenty links for a given subject.
Annotated.com
Jason has owned this one-word .COM domain name for many years after almost starting a company based around the name. A 2008 edition of Jason’s newsletter revealed that he bought annotated.com after being inspired by the concept of Third Voice, a controversial web annotation service that allowed users to comment on a website in a sidebar, thanks to a browser plug-in.
The company never materialised, and the name now forwards to Calacanis.com, Jason’s personal blog.
Inside.com
This domain name was acquired by Jason from domain investor John Quail for a reported $90,000. Inside.com has housed a couple of incarnations since Jason bought the name. Initially, Inside.com was developed as a news app in 2014, which used human curation to help readers discover the best coverage. Since then, Jason’s company has moved to email newsletters, offering many specific newsletters that are sent out periodically to thousands of subscribers.
Mahalo.com
At the start of this article, we mentioned that Jason launched Mahalo. Given Jason’s history of using high quality .COM domains, Mahalo.com was always the preferred domain. Mahalo.com was created in 2007 and increased in traffic from 10,000 visitors per month to two million per month in January 2008. According to Wikipedia, Jason stated in 2014 that Google Panda updates were “killing” Mahalo, which once had $10 million in yearly advertising revenue.
Now, Mahalo is a part of Jason’s Inside.com network.
