capital unless I really believed in the
investor. I hope that in the future we can
find alternative sources of funding, that
it becomes easier to self-fund, and that
people can get to profitability earlier.
When you invested in startups, what
mistakes did you see entrepreneurs
The worst was when entrepreneurs tried
to postpone solving di;cult problems,
hoping they’d just magically disappear.
That never happens. Especially the peo-
ple issues—those get worse unless you
have a conversation with those involved.
And even then it’s 50-50—but if you don’t
have the conversation, you can be 100
percent sure that it will get worse.
Also, don’t spend your money just
because you have it. Be frugal, because
your runway is really important. You
don’t want employees who are there just
because you’re spending a ton of money
on events or on alcohol or on a fancy chef.
You want people who are there to do their
work and not for the fringe benefits. Focus
on giving them great work to do and
valuing the work that they are doing.
You left Reddit in 2015, after becoming
interim CEO and trying to crack down
on the site’s widespread hate speech.
How have the large social media
platforms changed since then?
They’re more siloed, and more artificial.
The idea of having authentic interactions on these platforms is less realistic. Instead, we see people marketing
propaganda, or pushing for their idea
in a way that might not be truthful.
It makes me really sad, because the
What does that mean for the people
internet is such a powerful tool, and
it introduced this idea that you could
connect with anyone. And it’s been
turned into this weapon used to hurt
and harass people.
who run these companies? How
should they be responding to the
abuse on their platforms?
You always have an obligation to keep
your users safe, to make sure they are not
going to be harassed or shoved o; your
platform for expressing their ideas, or
attacked in real life by people sharing
their private information.
Those should have been principles
from the beginning. I do think the people
who started the internet thought it was
going to be a force for good, and I don’t
think they anticipated the level of harassment and invasiveness and harm that
people would use these platforms for. But
at the minimum, you want to prevent bad
things from happening on your platform.
What limits on free speech, if any, are
acceptable in trying to curb online
harassment and bullying?
The definition of free speech has
become convoluted. It originally meant
protection of the press from government
intervention. Now it’s come to mean that
people should be able to say whatever
they want on tech platforms, which are
run by private companies. This idea, that
private companies have this obligation
to allow any kind of speech, is actually
not something that is legally required.
Tech companies created some confu-
sion early on, because a lot of founders
used “free speech” as a marketing angle.
“Express whatever ideas you want!” But
when you make it a free-for-all, people
unfortunately come out with their most
terrible insults, and this horrible online
harassment that we’ve seen get worse
and worse over the past several years.
There has always been some censorship on platforms. They have always taken
down spam and some child porn. It’s just
when you get into certain types of content
that people get really upset.
One of the big problems is that
these platforms were built by homogeneous teams, who didn’t experience
the harassment themselves, and who
don’t have friends who were harassed.
Some of them still don’t understand what
other people are experiencing and why
change is so important.
Is it possible to create a place where
people can safely express any ideas
online, no matter how controversial?
I don’t think it’s possible anymore
except at very small scale, because the
nature of interactions at scale has
become very attention-focused: “The
angrier and meaner I am online, the
more attention I get.” This has created
a high-energy, high-emotion, conflict-oriented set of interactions. And there’s
no clear delineation around what’s a
good or a bad engagement. People just
Are any tech leaders taking this
I have been really impressed by [Medium
founder and Twitter co-founder] Ev
Williams’s coming out and saying, “Look,
we didn’t understand back then what the
internet was going to become, and we
really need to rethink what we’re doing.”
Another problem is that employees
who manage the behavior on these plat-
forms are not valued. It’s hourly work,
and the people who do it aren’t necessarily
trained that well. So you’re expecting
people who are clocking in and clocking
out to figure out hate speech—which
constitutional law professors are still
On top of that, you’re asking them to
deal with hate and harassment directed
at them personally. At Reddit, we had
employees who got doxxed [had their
private information published online].
So there’s a lot of fear, and it’s justified.
Meanwhile, the employees don’t see an
upside; nobody really seems to be hold-
ing them accountable for making sure
“For women in tech, this will be a really important year. Now people are actually open to change.”