This startup veteran wants to use email to build the next media empire – Business Insider

Jason Calacanis


Jason Calacanis wants to build the next media empire on the back
of an old standby: email, specifically email newsletters.

On Monday, Calacanis launched a
site called, which
functions as a Kickstarter-style system for identifying topics
ripe for their own recurring “top news of the day” email
newsletter. Topics that snag 1,000 sign-ups will see their own
newsletters produced by Calacanis’ team.

The building blocks of the
newsletters will be two or three sentence summaries of stories
from major publications, and links out to those

“We are going to launch 250 of these [newsletters],” Calacanis
tells Business Insider. His current “beta” roster includes eight
newsletters, which range from “Inside San Francisco” to “Inside
Electric Vehicles.” Collectively they have built a collective
audience of over 100,000 over the past eight months, he says.

The problem with news apps

Calacanis is the active angel
investor and serial entrepreneur who sold Weblogs to AOL for $30
million in 2005. But it was a frustrating moment in his career
that led him to, not one of his successes.

“We tried to make a news app,” he
explains. “It would be the Uber or Twitter of news … Everyone
agreed with that premise. There was a whole cohort [of startups]
that were invested in to do that … And they have all failed
pretty hard.” Calacanis ascribes this failure to two thing:
app-building is expensive from a technical perspective, and
getting a news app into people’s daily workflows is
extremely hard.

“Half a million people downloaded
the app, and about half gave their email,” he recounts. “Only one
percent of them used the app every day.”

So Calacanis started an
experiment. His team would email the top 10 stories of the
day to the email addresses they had gotten. They saw 40% usage
versus less than 1% on the app. “40x the return,” he says. “And
it cost 90% less. We didn’t need any of the developers.”

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The audience relationship

Calacanis isn’t the only one to
discover the power of a lean email newsletter operation. For
instance, the “morning briefing” cult hit TheSkimm, which
launched in 2012,
had grown to over 3.5 million subscribers as of April

But Calacanis is banking on a
relationship with his audience to drive to

The first piece of that
relationship is letting the audience pick the newsletters
that get made through the Kickstarter-inspired system.

The second is the ability for readers to “reply” to any of
the newsletters and have their emails be read by the team.

“We are actually spending about a
third of our time encouraging people to reply and then
interacting with them,” he says. “If I reply, somebody will
actually get back to me. That really changed everything.”

Readers are correcting the
newsletters, correcting the source material, and participating in
an ongoing discussion about whether the newsletters are too
left-leaning. “Are we  treating Hillary with kid gloves?”
Calacanis asks. And he says this relationship will continue to

This intimate reader relationship
is also what Calacanis says will help his team lean away from

“People who sign up for the email
are opting into curation,” he says.

These readers aren’t just seeing
a headline pass them by on social media, so there’s not the
necessity for a big hook to get them interested. Instead, the
content of the email is focused on a succinct summary of each
story. “It’s an executive summary [of the news] in the vertical
or verticals that you care about,” he says. Even if
readers don’t click through to all of the articles,
Calacanis wants his readers to walk away informed.

And he’s not worried about
publications feeling he is stealing the meat of their stories.
“If you are fair to people, they will respect ‘fair use.’ If you
are unfair, people will sue you and write letters,” he

The money question

As to money, Calacanis sees
revenue coming from both ads and patronage. “1-5% of people who
consume media want to support it,” he says.

But the big key to success will
be keeping costs down, Calacanis says. “There’s no
infrastructure, no printing press, no fancy office, no big level
of mid-management. There’s two or three writers working on a
vertical, and they can hit publish.

“We think this is the key to
scaling it,” he says.


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