Jason Calacanis on the new Inside.com, the state of the media and what's interesting to investors

Do you collect emails? Angel investor and entrepreneur Calacanis says it's the way to success.
 By 
Kerry Flynn
 on 
Original image replaced with Mashable logo
Original image has been replaced. Credit: Mashable

Jason Calacanis, who sold his company Weblogs to AOL for $30 million in 2005 and was an early investor in Uber and other tech startups, said he doesn't need to work again.

But as a serial entrepreneur who cut his teeth as journalist before launching several publications, he has dedicated himself to creating another media company, Inside, and building it into a profitable business.

"I really want to set journalism on a path that's more sustainable where publications cannot survive on advertising," Calacanis said in a recent interview with Mashable's Biz Please podcast.


You May Also Like

In this week's episode, Calacanis explains why he thinks the media industry has fallen in a trap, once again, and how they can get out of it. He also shares other investment trends in Silicon Valley. For example, Calacanis recently invested in robotic coffee maker, Cafe X, that he says aligns with the current interest in robotics and automation.

Calacanis takes us through his personal experience navigating the search engine optimization revolution (which propelled the reach of new online publications like his own Weblogs) to the era of optimizing for social media and now the present state of relying on third-party platforms like Facebook's Instant Articles, Google's Accelerated Mobile Pages and Snapchat Discover.

The entrepreneur's latest bet does not involve entrenching itself into third-party services, and it's not about making your own mobile app. In fact, that was the original idea of Inside until Calacanis discovered that less than 1 percent of users opened the app daily.

Inside is, instead, a network of email newsletters where the topics will be selected by readers. It launched Monday with eight newsletters serving an audience of more than 100,000. Any subscriber can go to Inside.com to vote on a new topic.

Calacanis said he hopes to grow that base to 250 newsletters with 10,000 to 1 million subscribers each over the next three years.

"It's going to be a very boring business but I hope it can be a very boring profitable business that has incredibly high editorial ethics and an incredible focus on reporting the truth and high quality," Calacanis said.

For more Biz Please, subscribe to the podcast on iTunes and find them here on Stitcher

Mashable Image
Kerry Flynn

Kerry Flynn is a business reporter for Mashable covering the tech industry. She previously reported on social media companies, mobile apps and startups for International Business Times. She has also written for The Huffington Post, Forbes and Money magazine. Kerry studied environmental science and economics at Harvard College, where she led The Harvard Crimson's metro news and design teams and played mellophone in the Band. When not listening to startup pitches, she runs half-marathons, plays with puppies and pretends to like craft beer.

Mashable Potato

Recommended For You
Elon Musk found liable for defrauding Twitter investors
Elon Musk arrives at federal court on March 4, 2026 in San Francisco, California.


'The Wrecking Crew' review: Jason Momoa and Dave Bautista resurrect the buddy-cop comedy with a BOOM
Dave Bautista and Jason Momoa star in "The Wrecking Crew."

Jimmy Kimmel has a damning response to Trump's State of the Union 2026
A man in a suit stands on a talk show stage.

'Over Your Dead Body' trailer: Samara Weaving and Jason Segel are a totally toxic couple
Over Your Dead Body poster cropped

Trending on Mashable
NYT Connections hints today: Clues, answers for April 3, 2026
Connections game on a smartphone

Wordle today: Answer, hints for April 3, 2026
Wordle game on a smartphone

NYT Connections hints today: Clues, answers for April 4, 2026
Connections game on a smartphone

Google launches Gemma 4, a new open-source model: How to try it
Google Gemma

Wordle today: Answer, hints for April 4, 2026
Wordle game on a smartphone
The biggest stories of the day delivered to your inbox.
These newsletters may contain advertising, deals, or affiliate links. By clicking Subscribe, you confirm you are 16+ and agree to our Terms of Use and Privacy Policy.
Thanks for signing up. See you at your inbox!