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The Evolution of Twitter creator Ev Williams and Medium



evolution of ev williams 2x1
Williams’ evolution.

Greene/Web Summit via Sportsfile; Samantha Lee/Business

  • Ev Williams invented Blogger in 1999, Twitter in 2006,
    and Medium in 2012. In many ways he created the digital content
    ocean we’re swimming in today.
  • But Williams believes social media has become toxic.
    “I’ve pretty much weaned myself off of being addicted to social
    media,” he tells Business Insider in an exclusive
  • “If you create a system that rewards attention, the
    easiest way to get attention is to be a bad actor. That
    underlies our media ecosystem, that underlies our political
    system, and it’s degrading society in so many ways,” he
  • Now, Williams has a solution. He has created a new
    business model for Medium that rewards high-quality content and
    suppresses trolls. If it works, the internet will become a
    better place to live.
  • He also told us how he’s trying to become a better
    manager, by reading anonymous feedback from his staff.

First, let’s correct a myth: Ev Williams definitely has
a desk.

Earlier this year, the New York Times reported that Williams —
the billionaire entrepreneur who founded Twitter and Blogger —
runs his new company, Medium,
from an office that has no desk
. The article included a photo
of Williams resting on a sofa at his headquarters, no desk in

It conjured an image of a mercurial Silicon Valley mogul,
controlling his minions from an iPad or a phone. Maybe, I
thought, he had discovered a disruptively unencumbered new style
of leadership. Perhaps “no desk” was the natural evolution from
“standing desk,” another Silicon Valley efficiency cliche. So I
went to Lisbon, where Williams was addressing the Web Summit tech
conference, to ask him about the future. Will we all eventually
find ourselves in a desk-less work environment, sprawling around
on office sofas, like Williams?

I first saw him at a party hosted by Brooke Hammerling. Her Brew
PR agency has long been a one-stop shop for high-level Silicon
Valley connections, and her annual Web Summit party did not
disappoint: It was at the
Chinese Pavilion, in Lisbon’s trendy Principe Real
, near a clifftop park that has a spectacular
view of the castle that dominates the city’s skyline.

Williams didn’t stay very long, although he talked to former
Twitter CEO Dick Costolo, who was also at the bar, along with

Juliet de Baubigny, the senior partner who just left Kleiner
to join Mary Meeker’s new VC firm. Rachel
Dodes-Wortman, the former New York Times and Wall Street Journal
writer who became head of film partnerships at Twitter (but now
runs communications at Knotel), was also there. It was more of a
work meeting than a party, and Williams left at around midnight,
after summoning a car on his phone.

The next day, I found Williams in a conference room backstage at
Lisbon’s vast Altice Arena. He is tall, skinny, and his face now
carries a middle-aged beard, highlighted with grey. He is, at 46,
literally one of tech’s legendary greybeards. He does not appear
to particularly enjoy talking to the media. So he picks his words
carefully, and talks in a thoughtful, deliberate way.

He is, conspicuously, sitting at a table that he is clearly using
as a desk.

And he is baffled by my question.

“I have a desk!” he says.

He looks over at his PR staff. “Did that get reported, that I
don’t have a desk?” They remind him that it was indeed reported
last year that he has no desk.

A light goes on.

“I didn’t have a dedicated desk,” he says, meaning that
he had a desk, but not like an official desk in a stereotypical
corner office, or something like that.

Free-desking didn’t last long. “I got a desk in the meanwhile. I
needed somewhere to put my computer.”

This is disappointing.

Williams has not discovered a magical new way to run a
company. He’s a normal human being, with a normal desk, just like
the rest of us.

If you’re distressed at the volume of digital media noise
funnelled at you each day, then Williams accepts the blame

Ev Williams
Williams prepares his
microphone backstage at the Altice Arena in

Greene/Web Summit via Sportsfile

Well, not quite normal.

Unlike the rest of us, Williams’ thoughts have had a surprisingly
large impact on the way we all think.

This is the man who invented Blogger, in 1999. At the time — the
early days of the internet, really — it was not obvious that
there would be a vast marketplace for people who wanted to
comment on news coverage originally published elsewhere. Or that
billions of people would want to read summarised aggregations
rather than the original reporting on which it was based. His
realisation that the internet needed high-quality publishing
tools for amateurs made blogging into the oxygen of the media
There are now 173 million blogs on the internet

And then, in 2006, he did it again. It was equally not-obvious
that anyone might want a micro-blogging platform which
constrained authors’ thoughts to just 140 characters. Yet now we
live in a world where much of our news is delivered first on
Twitter. There are 326 million Twitter users out there. It’s the
president of the United States’ favourite bully pulpit.

Williams’ thinking has made him rich. He owned 43.7 million
shares of Twitter when it went public at $26 a share in 2015,
making him an instant billionaire. (He has since sold at least
30% of his stake.) Not bad for the boy who grew up on a farm in
Clarks, Nebraska.

If you’re distressed at the volume of digital media noise
funnelled at you each day, and the way Twitter reduces everything
to a shallow take, shorn of detail, context or nuance … then
Williams accepts much of the blame.

He once said of President Trump’s use of Twitter
, “It’s a
very bad thing, Twitter’s role in that … If it’s true that he
wouldn’t be president if it weren’t for Twitter, then yeah, I’m
sorry.” He had believed that Twitter’s ability to let anyone say
anything, to a wide audience, would mean that “the world is
automatically going to be a better place.” But, “I
was wrong about that
,” he said.

“If you create a system that rewards attention, the easiest way
to get attention is to be a bad actor. That underlies our media
ecosystem, that underlies our political system, and it’s
degrading society in so many ways.”

Ev Williams
Williams has all but given
up on social media. “I’ve pretty much weaned myself off of being
addicted to social media for instance, which I was at one time,”
he says.

Greene/Web Summit via Sportsfile

Later, on the 20,000-seat centre stage at Web Summit, he was
asked, How do we get out of the “attention economy” feedback-loop
cesspool? His reply is incredibly insightful, and it’s worth
reproducing in full:

“The fundamental problem that we’re focused on is a microcosm of
one of the biggest problems in society, which is simply that we
have created a world in which attention is rewarded in
quantity. Meaning it’s not the quality of the
attention, it’s not how you make people feel. It’s whether you
get their attention. And we’ve optimized these systems —
traditional media, social media, online and offline — where
attention is rewarded, and what we can measure is rewarded. And
we can measure whether people are paying attention by what page
their browser is on, or what social media they’re liking, but we
can’t actually measure how they feel, we can’t measure if they’re
getting smarter, we can’t measure if they’re understanding the
world better. So we’ve really created this system in society
where the class clown, the disruptive kid in school who is very
effective at getting attention, but not effective at helping
people, that becomes the winning play. … Obviously, if you create
a system that rewards attention, the easiest way to get attention
is to be a bad actor. That underlies our media ecosystem, that
underlies our political system, and it’s degrading society in so
many ways.”

Today, Williams has all but given up on social media, he tells
Business Insider. “I’ve pretty much weaned myself off of being
addicted to social media for instance, which I was at one time,”
he says.

That’s an astonishing thing for the founder, former CEO, and
current board member of Twitter to say. It is akin to Mark
Zuckerberg announcing that he tries to not spend time on

Now he limits — or tries to — how much time he spends looking at
his phone.

“The kids are the biggest forcing function, and I’m faulty on
this as well, but I’ll usually make my kids breakfast and try not
to be on my phone while doing that, so that’s good, and then
they’re gone and then I’m like in work mode,” he says. “I’ll look
at my email before I leave the house and when I’m walking to the

The good news is, Williams does, in fact, believe he can fix
this. So it’s worth exploring the evolution of his thinking.
Twice he has been ahead of the curve and created media tools that
altered our universe.

Now he is trying a third time.

Monetising the value of “How I Got My Husband to Actually Do His
Share of the Housework”

Ev Williams
By audience size alone,
Medium is already in the same league as The New York

Greene/Web Summit via Sportsfile

If Blogger was an iteration of the “traditional” digital
publishing done by news organisations, and Twitter was an
iteration of blogging done by amateurs, then Medium is a further
iteration of both. It’s a publishing platform that specialises in
long, thoughtful, one-off posts by writers who are not producing
a stream of frequently updated content.

And it is huge.

Twenty-thousand articles are published on Medium every day, there
are 20 million stories in the archive, and the site has 90
million unique readers per month. That’s roughly the same as the
New York Times, according to ComScore, but with only about 100

The addition of subscribers to Medium is the new innovation that
is being most closely watched by competitors in the media. You
can read three articles on Medium for free, every month, before
you encounter a paywall. Normally, companies that charge
subscriptions are offering a high-quality stream of useful,
fact-checked, niche-themed content, so you know what you are
getting. (The Wall Street Journal and Business Insider both want
you to pay for business news, for instance.)

But Medium’s content is random. On November 14, Medium’s front
page had articles such as, “How
I Got My Husband to Actually Do His Share of the Housework
Do Our Sex Dolls Go After We Die
?” and “The
Books That Saved My Life in Prison
.” It has also published a
lengthy, impressive dissection of
the sham behind the infamous Stanford Prison Experiment

Will people want to pay for a product that consists entirely of
surprises, of varying quality, from writers who don’t work
full-time? Williams says yes. “The whole system is growing, both
topline uniques, visits, posts, and subscribers,” Williams says.
He declines to talk about revenues, however.

Growth is not the same as profit, either. Williams has so far
taken $134 million from investors since 2012, and he confirmed to
Business Insider that the company remains unprofitable. The
investment is a massive sum for what is, in many ways, a
magazine-format media company. And six years is a long time to
run without finding a way to sell your product for more money
than it costs to make.

Williams says he will be seeking more investment soon
. It is,
perhaps, not a coincidence that he did the media tour at Web
Summit in November. Good publicity often helps companies persuade
VC investors to part with cash.

Medium abandoned its previous business model, advertising, over a
year ago. Advertising could have been good for Medium. With 90
million users, even if the site ran only automated “programmatic”
ads, it would have generated revenues in the millions of dollars.
But Williams didn’t go programmatic. Instead, he offered
sponsored content — handcrafted stories written specifically to
please brands — which Medium then promoted around its unsponsored

Williams has a bewildering explanation of how this worked:

“Sponsored content is a particular type of content that we could
charge to have created. So what we did was package creation,
hosting, and distribution. And so the creation of that content
isn’t the creation of other content, it’s the creation of
sponsored content. So the only way for that to pay for
non-sponsored content is by advertising the sponsored content on
the non-sponsored content. Meaning, we could get paid for
creating sponsored content but we couldn’t pay someone who was
creating non-sponsored content, except by putting ads on the
non-sponsored for the sponsored content, and then that is being
monetised. So our company is being monetized with sponsored
content, the content that is not sponsored is being monetised
with an ad.”

He pauses for a beat, and adds, “We stopped all that.”

His former girlfriend once told The New York Times: “He’s not CEO

Ev Williams
“I’ve screwed up in many,
many, many ways in terms of managing people,” Williams admitted
in 2010.

Greene/Web Summit via Sportsfile

“We stopped all that” are four words that cover a tough period
inside Medium. Fifty people — one-third of the workforce — were
laid off in 2017 as Medium pivoted away from advertising. He cut
ties with a number of publishing partners. He made a lot of
people angry.
Sources told Business Insider at the time
that they regarded
Medium as a “s—show” and a disorganised “vanity startup.”

Read more:

INSIDE MEDIUM’S MELTDOWN: How an idealistic Silicon Valley
founder raised $134 million to change journalism, then crashed
into reality.

The episode also burnished Williams’ reputation as
not-the-best-CEO-who-ever-walked-the-Earth. In addition to being
Twitter’s creator, he was also the CEO from 2008 to 2010, a time
remembered for infighting between the founders. Current Twitter
CEO Jack Dorsey — who still sits on the board with Williams — was
once asked by The New Yorker what he was thinking in 2010 when he
helped persuade the board to force Williams out of the chief
executive’s chair in favour of Dick Costolo. “Was
I thinking, Screw Ev? Emotionally, was I asking that? I don’t
know. Maybe
,” he said.

“I’ve screwed up in many, many, many ways in terms of managing
Williams admitted in 2010
. Even his girlfriend agreed: “It
was bitter, horrible and tough. He’s not CEO material. It doesn’t
play to his strengths. He’s a better inventor; he’s better at
coming up with ideas,”
Meg Hourihan told the Times

But that was eight years ago. Things have changed. Williams has

The stuff that gets the most traffic is often the most awful
content on the net: Porn. Clickbait. Politically biased news.

Ev Williams
Williams wants to reward
the best content — financially.

Greene/Web Summit via Sportsfile

The real problem with advertising on Medium, Williams says now,
is that “I didn’t think it would ultimately create the incentive
structure we were trying to do, which was to really reward the
best content. You can build a business around it, but it doesn’t
directly support great content.”

That bit about “reward the best content”?

That is key to understanding why Williams has eschewed the
simplest, most lucrative way — advertising — of monetising his
site. To make advertising pay, sites need to rack up huge
audiences. The problem is that the content that gets the most
traffic is often the most awful content on the net: Porn.
Clickbait. Politically biased news. That’s how a bunch of
in Macedonia got rich in 2016,
 by pumping out fake
pro-Trump stories for gullible Americans to click on, such as
was caught cheating with Eric Holder — OBAMA IS FURIOUS!!!

And that’s
why Williams regards the internet as being like a “car
Everyone stares at car crashes. But the internet
interprets this as a demand for car-crash content, and supplies
ever more of it. Williams wants to turn that on its head and
create a virtuous cycle in which people are rewarded for
supplying only the highest-quality content. People are happy to
tolerate advertising alongside free porn. But they are generally
only willing to pay to read reliable, helpful material.

He is rewarding that content financially, too. A team of editors
now assigns paid freelance articles, just like a magazine. And
anyone can sign up to Medium’s “Partner Program,” which gives
writers a slice of each $5 subscription based on how deep a
subscriber’s engagement went.

“Our content spend in 2018 will be more than $5 million. We are
budgeting multiples of that for next year,” Williams says.

As an example, Williams talks about a recent article on how to
set up your iPhone for minimal distraction. “It was a 73-minute
read. It was deep, meaningful content but it can be curiosity
driven, it can be utility driven, it can be every topic under the

“I’m still just obsessed about how I use my time”

Ev Williams
Williams regards himself
as a former social media addict.

Greene/Web Summit via Sportsfile

“Minimal distraction” is a subject close to Williams’ heart. As
an ex-social media addict, he is trying not to use his iPhone.

He has switched off many of its notifications and tries not to
take it with him to events with friends or children

“I’m still just obsessed about how I use my time,” he says.

And does he really wear a wristwatch so that he isn’t tempted to
look at his phone to see the time?

“I do wear a watch. It’s a regular old-fashioned wind-y watch.”
Then he gestures to the watch with his free hand, in a jokey way,
as if he’s trying to sell it on a cable TV shopping channel, and
says, “It’s a Vacheron. A Swiss watch. It’s very nice. I
sometimes wear a Swatch, but this is my fancy watch.” And we all

He doesn’t know which model of Vacheron Constantin he is wearing
— “It’s the very thin one?” — but a cheap Vacheron retails for
£16,500 ($21,000) and an expensive one will run you to £69,300

Williams says he has not been successful in leading a
distraction-free life.

“I try to but just like all of us, I’m faulty.”

That obsession with time well-spent recently reared its head
inside Medium’s HQ. Williams was trying to solve a problem
regarding Medium’s recommendation system. Readers who like what
they find on Medium can offer “claps” (similar to likes), or
share it on social media (like Twitter), or respond with a
comment. Every website has something similar.

Read more:
Here’s how the other Twitter cofounders reacted to Jack Dorsey
becoming CEO

But Williams believes that Medium’s comments ecosystem has a
unique advantage. On Medium, comments are called “responses,” and
they don’t thread like other comments sections. It suppresses
trolls and insults, and promotes positive, helpful responses.
Comments don’t get shown to other readers unless the author
approves them and if the reader follows the commenter. The author
has control over what responses are elevated above the rest, by
either clapping or responding to the conversation. Other comments
— negative criticisms, random bulls–t — can be removed by the
author, or are otherwise “buried” a click away from the story
itself. At the same time, writing a comment on Medium involves
creating something that looks like a separate post, making the
writer feel self-conscious about using the format for a quick
insult. When you log in, other users reward you with
notifications if they think your comments are good.

Put those two things together: A revenue system that rewards
high-quality work; and a recommendation ecosystem that suppresses
trolls and promotes constructive behaviour: That’s Williams’
latest evolution.

Meetings that last as long as an entire working day

Ev Williams
He also likes really long

Greene/Web Summit via Sportsfile

Williams got to this place in part by instituting his favourite
new management trick: Meetings that last as long as an entire
working day.

“Here’s a thing I believe in and want do more: Have fewer but
longer meetings,” he says.

Most people hate meetings. There’s a whole management school
ideology around holding meetings while standing up, or walking
outside, or banning PowerPoint, to make them shorter and more
focused. Is he serious?

“Longer meetings, yes,” he says.

“This is a counterintuitive thing,” he says. “Often there’s
complex problems. You have a series of meetings, you never make
progress because it’s like cleaning out a closet. You actually
have to get everything out, and get organised, and dedicate a
significant amount of time to actually crack the nut of a complex
problem rather than chip away at it incrementally and when you
identify those problems it’s actually a lot more productive to
get everyone together for half a day, or a day, and actually
figure something out, than to do it in your regularly scheduled
meeting. That’s a trick I am a fan of.”

“We had one of those … last week.” It was a half-day meeting on
the recommendation system, and it brought in engineers and
product managers, after months of development. Staff were asked,
“OK, what have we learned, what do we know? Rather than just the
weekly ‘what are we doing next?’ It’s complex, it’s big, and we
made a lot more progress in that meeting than we had for a
while,” Williams says.

“As we started focusing on subscriptions, rather than just
engagement, we found that the quality of stories mattered, not
just whether someone was interested in it (or even whether they
read it). Quality is, of course, still hard for machines to
determine, so in the last year we started doing a lot more human
curation, which has driven a change in our machine-based
recommendations,” he says.

“This year, we built a new recommendations engine from scratch.
It’s doing better than the old system, but we think it can be a
lot better. There are many ways we might go about this — from
focusing more on topics, to various NLP [natural language
processing] techniques, to author-follow relationships, to
collaborative filtering, and other [machine learning]-based
techniques. We have tried a whole bunch of things, some which
have worked, some which have not.”

“It takes time to get up to speed on what we’ve done and what
we’ve learned recently, it wouldn’t have worked to have a regular
one-hour meeting. And if we’d had a series of shorter meetings
instead, we would have had to reboot the discussion each time,”
he says.

The latest iteration of Ev is determined to learn from his
mistakes — so he gets anonymous HR reviews from his staff

ev williams
Williams has developed a
content recommendation system that promotes useful feedback and
suppresses trolls.

Diarmuid Greene/Web
Summit via Sportsfile

But do his staff like it? Or are they thinking, “Oh my god, Ev
wants another one of his endless meetings”?

He laughs, “As a CEO you never really know the truth, but they
said they liked it! I’ll have to get the anonymous feedback.”

That is another way that Williams has evolved. Now, he is more
determined to learn from his mistakes. He receives regular,
anonymous “360-degree” feedback from staff on what he is like as
a boss.

“I did one just recently,” he told us. “There was some bad stuff
so I assume there’s a least some truth. But it was super helpful.
The last one I did was probably a year and half ago [right after
the layoffs and the pivot from advertising] and then I just did
another one. It gets interesting when you actually see change.”

“The first one that I really took to heart was that I say I am
interested in the bad news and negative feedback but I don’t
actually act like it, so …” he tails off, laughing at himself.

“The bad tendency was to dismiss people’s concerns if I didn’t
believe they were valid. Before, I dismissed it. So now it’s
about listening better and acknowledging the concern, making sure
I acknowledge the validity of the concern even if I disagreed
that it was a problem.”

“There was less bad stuff. So either people are less truthful or
I made progress!”

Ev Williams

has also committed to listening more to his

Greene/Web Summit via Sportsfile

Since the Times’ “no desk” story ran, Williams has become
increasingly deskbound, in part because he wants to listen more
to his staff.

“We rearranged the office. I kind of wasn’t talking with my
executives enough so we put our desks altogether, so we have a
place just to have casual conversations. It’s in the open. I also
have a dedicated conference room that I call ‘my office.’ There
is this Silicon Valley image of, you just don’t have an office,
and you are mixed in with the people. But I need a place to meet
[privately] with people, also. It’s helpful to be able to close
the door and have conversations. I also make a lot of phone

On any given day, “I’m barely at my desk. I’m often in my
conference room,” he says.

At one level, the no-desk thing is trivial. He tried an office
without a desk, but now he uses a desk to help him communicate
with his people. So what? Big deal.

But it typifies the evolving, layered way Williams thinks. A desk
is just a thing you put your computer on, sure. But its position
also determines who gets to talk to you, and who does not; what
information reaches you, and what does not. (Pretty much like the
positioning of a publishing platform in a media ecosystem.)

Right now, Williams is trying to listen more. He thinks he is
succeeding. In the anonymous HR review he got recently, he tells
me: “There was less bad stuff. So either people are less truthful
or I made progress!”

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