Pressable: A Radically Different Culture Inside Automattic

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Hey, Vic, welcome to the program.

Thanks for having me, Matt.

CEO of Pressable, first podcast ever.

I am delighted to have you here
as the as the first podcast.

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In the show notes, when I interviewed
Jess Frick a few months ago, we talked

about sort of Pressable as sort of having
like the startup culture vibe, like a

startup within a startup, even though
Automatic is a billion years old in

tech terms, is that a, is that a culture
that you, that you really latch onto?

Is that a vibe you really latch
onto as the CEO of Pressable?

How do you do it?

Uh, is there a sort of North Star for sort
of being like, You know, the, the, the kid

in the classroom amongst the 2, 000 other
automaticians that are at the company.


Vik: absolutely.

I think, uh, we focus.

On trying to be really
rapid with anything we do.

So, you know, I think in a larger
organization, you have to, you have to

coordinate with, in this case, a couple of
thousand people to make a lot of changes.

And in principle's case, because
we're, we're isolated and, uh,

we treat it like a true startup.

We can just say, Hey, we're,
we're going to go build something.

And We don't need to think about
it after that, we just go do it.

Uh, and so that lets us, I think,
go to market with features and

functionality and marketing changes
and anything a lot faster than a larger

Matt: organization would.

You all recently did, recently again
within a couple months, a sort of

redesign of the dashboard and an
approach of how folks can manage

their sites, uh, through Pressable.

I assume if that was like a dot com
rollout, it would have been years

for that to like go out versus
maybe your team is a lot more.

A lot more agile.

Do you have to like, run things through
the auto automatic org chart to make

those changes or it is, like you said,
like we can rapidly deploy this as

long as it's sensible, you know, UI
customization or upgrades to the platform.

Vik: Yeah, the latter.

We can, uh, I think in the case of
the dashboard project, uh, our front

end designer Wayne, uh, just, you
know, one night was thinking about it.

He didn't talk about it with anybody.

Just a couple of days later, he came to us
and says, Hey, I've got this great idea.


Honestly, I think within six or eight
weeks or so, he had a functioning

version of what you see today.

And, you know, it was just
a quick, yeah, let's do it.

No, no coordination with
anybody inside Automatic

Matt: for that.

One of the things that was interesting
when I talked to, to Jess is.

That, you know, at Automattic, and, and
recently Matt made this post, he's going

on or has gone on sabbatical, but he
made this post about cards in Automattic.

It's the only way I know how to say
it, you probably have the right term

for it, but cards in Automattic,
where there's a bunch of hosting

companies that a lot of people probably
just don't think of off the top,

immediately off the top of the head.

Pressable, of course.

com, VIP, which sometimes people
can forget about if you're not

really talking about enterprise
in WordPress a lot of the time.

And then maybe the WP
cloud project, is that?

Does Jesse Friedman and
team get hosting cards?



Vik: they're actually the help
the host because they're, they're

trying to, they're trying to make
every host out there successful.

Whereas pressable VIP and.

com are more the be the host.

Matt: And where I was going with this
is like stitching that communication

across the organization, right?

So pressable might have a customer,
let's say whale of a customer, right?

I used to be a sales guy for.


Whale of a customer.

And then somebody at VIP goes,
Hey, hey Vic, who's that?

Who do you have over there paying you
30, 000 a month on your infrastructure?

Why don't we slide them over
to, you know, the VIP side?

It's just an interesting dynamic
to have these multi brands

across Automatic for Hosting.

How do you all communicate?

Do you have like, these are my customers,
this is my customer type, so we're

going to keep it on our infrastructure,
and if they were a large publisher,

then sure, they can go over to VIP.

How do you split that sharing
of customers and approach?

Vik: Yeah, you know, I
think it's pretty simple.

And the way we approach everything is
what's best for the customer, which

business or which platform is going
to serve the customer's needs best.

And that's what matters, right?

It's not about where does the
revenue belong or which one's

going to drive more revenue.

You know, I think a good example, we
had a lead come into Pressable a few

months ago, and it was very clearly an
enterprise site, it government related.

We could have hosted it without any
challenges, but you know, we thought

they would be better served by VIP.

So we, we sent it over to
them and they're now with VIP.

Matt: What about WooCommerce?

Do you have an approach
when you're building out?

whatever solutions for WooCommerce,
whether it's in the dashboard or the

hosting infrastructure, do you have
the flexibility to say, Hey, we, we

can come up with our own way of doing.

WooCommerce hosting or is
automatic as a whole saying, no,

like we're going to usher in this
hosted WooCommerce experience.

Or do you have that freedom to to create
your own Woo kind of implementation?

Vik: I think we have the freedom to
create our own implementation and to

work pretty closely with the Woo team
on sites that You know may not be best

for WooExpress, but they're not quite
at the VIP level And so we work with

with Woo and those customers pretty
closely to put them on Prestable today

Matt: I'm trying to illustrate this
picture, especially against the canvas

of these cards that Matt just launched.


If you have a host card at Automatic,
you are part of one of the hosts,

and your job is to encourage
folks to host with your brand.

So Vic is probably going to have the
Pressable hosting card, and he's going

to encourage you to host with Pressable.

You might run into another
Automatician who has helped the

host card, and that's to help with.

With any host, right?

Is that the thing?


Vik: absolutely.

And so I think in the example of Woo,
they may have a customer that comes in.

That's at some third party host, uh,
I think WP engine or Kinsta wherever.

Uh, and if we can solve the problem
for them while they stay at that host,

you know, we're going to do that,
obviously, if, if we think they may be.

And I think that the goal is
very much to be, uh, neutral

in, in that, in that sense.

So they're helping the customer
regardless of where they are.

So ultimately we're
helping all the hosting

Matt: companies.

And if you're at like PocketCast, you're
like, yeah, I just go host at Wix.

Doesn't matter.

It doesn't matter to us.

Every WordPress is special.

I think it's as Matt put it, right?

It's like this rising tide, you
know, lifts all boats and it's

sort of a, just another Yeah.

You know, we've seen this, um, in the
industry for a while where, uh, automatic

invests so much, uh, time and resources
that, you know, one might feel like, well,

you know, if we're another web host, why,
why, why would we work with automatic

when they have their own hosting?

So it's, it's competitive, you know,
but you could flip the table and

say, well, you're profiting way more
than automatic is on this hosting.

So as a sort of neutral way of saying,
Hey, look, are all of automatic will help.

because we want just WordPress to thrive.

However, if you're on
the pressable team, the.

com team, the VIP team, we
will say our product is great

and you should host with us.

And I think that's a fair
way, a fair approach to it.

Vik: Yeah, absolutely.

And I think, you know, the, the thing
we, I think want to convey to everybody

in the community is WordPress as a
whole, this open source project is

Vital and the entire community needs
to exist and be successful for,

for anybody to exist in it, right?

It's not just about automatic.

It's about all the theme and
plugin developers and all the

other hosts being successful

Matt: as well.

It's a good, uh, transition,
uh, how WordPress is vital.

I mean, part of the reason why I do what
I do here at the WP Minute is because

it's not just, Hey, I love WordPress.

I love to tinker with WordPress.

I love to build with WordPress.

That's an element of it.

But WordPress as an open source.

app that's so widely used.

It doesn't mean people care about it.

I mean, it doesn't mean like the
person running their WordPress

website, like loves WordPress like
we do and like cares about it.

But there's a freedom that they
don't really fully understand

what they have that this tool is
built largely out in the open.

with thousands of developers
contributing to it.

And then, then there's a pool of sort
of what I'll say, third party, the

community, which also supports it,
which you just don't get from any

other crucial app in your life, right?

You don't, unless you run
it, unless you're the diehard

geek and you just run Linux.

Uh, on your, on your laptop, you know,
in your, in your home devices, right?

But you, you don't get
it from a Microsoft.

You don't get it from an Apple.

You don't get it from the computer
that runs your car or your television.

Like this stuff is so vital, I think,
to, to humanity from the software side,

from the publishing side, it blows my
mind that people in tech still don't get

this press media, other startup founders.

They don't understand the, the gravity of.

of WordPress, which is still
boggling to me in 2024.

It seems

Vik: pretty fundamental,
especially in the web.

I think it's, I don't know what the
current status, but 40, 45 percent of the

web is powered by, by WordPress today.

And you look at some of these closed
platforms that exist out there that then

own your data and you're limited in how
you build your site, how you can market,

whether it's SEO or whatever it may be.

Um, And then you compare it to
WordPress and there's such a

huge, huge advantage that I don't
think everybody truly appreciates.

Luckily though, I do think the, at
least the WordPress community largely

does appreciate, especially everybody
who's contributing back to core.

Matt: One day when Matt is
on a TechCrunch interview.

I hope they finally understand since
they've been running on WordPress for a

decade plus because I helped build the
first version with 10 up years ago when

they actually ported over to WordPress.

I hope that one of the reporters or
podcasters there finally understands

like dot com dot org and the
value of open source WordPress.

It drives me bonkers, uh, that we're still
having to define that and define the.

the value of having open source.

I saw somebody on Twitter the other
day, you know, saying I haven't

touched WordPress in eight years
and I logged in and it's a mess.

And you know, screenshots showing
all this, the frustrations.

One, you haven't touched
it in eight years.

What, what did you expect?

Uh, but two, he's like, I'm a developer.

Why should I use any of this when
I can get web flow and all this.

Because it's open source, man.

Like we can all do this together.

You're not going to love every
nook and cranny of WordPress, but

it's yours and you can participate
and help make this thing better.

I get really emotional when I start
talking about this stuff, when I see it,

uh, especially when I see it on Twitter.

But man, it's like, I think you, the
The human race needs to get educated

on data ownership and lock in.

Like you have to make these, you
have, there's no, you can't just,

Oh, Facebook, here's all my stuff.

Here's all my photos.

Here's all my videos.

You have to understand what
you're doing with this stuff.

You can't just like throw it out
there and then say, well, whatever

happens to my data happens or I don't
care if I have to pay absorbent fees

if they just keep raising price.

We have another solution.

It's not perfect, but it's there.

In my

Vik: opinion.


And, you know, you talk about data, data
archive, like there's this data liberation

product or, uh, concept now, uh, and, you
know, over the years I've, I've talked

to many, many business owners who are
running e comm stores and they move from.

Woo or magenta or whatever, it's a Shopify
and then a couple of years later, they

want to get back and they want to get
out of it and go back to something like

WordPress with with Woo because, uh, they
can't do so many things within Shopify.

But they're locked into it and they didn't
realize and understand just how Hard it

was going to be to move away from it.

So the I think this data liberation
Focus for this year is is a big one

to help people Hopefully understand
but at least give them opportunities

to get out of some of these closed
platforms and support the open source

Matt: community Let's
unpack that a little bit.

Was that sort of like a And all my air
quotes for those watching, was that

like an all hands for automatic to
say, like, just like this host thing,

we all have to be part of this data.

Like, is there a, I don't know.


I don't want to say okay.

Are, but is there like a KPI?


Are that that pressable has to do to
help with the data liberation project?

Is that an all hands kind
of thing across automatic?

I think the

Vik: desire is if we have any tooling
that exists to help migrate, uh, aside

from one platform to another, that we
should be contributing it, contributing

it to the, um, To the project.

I don't know if there's KPIs or something
like that around it, but, you know,

I think it is, it's a very important
focus for the community to be able to

survive because as time goes on, people
who are building their sites at Wix

and Squarespace or, you know, Shopify,
wherever are ultimately going to realize

that it's great for very specific needs,
but as your business grows, uh, it's

probably not best for your business.

Matt: Yeah.

I'll never understand how.

And this was another thread
and I saw Matt chime in on it.

I forget which e commerce.

Store it was, but I think they
said they were hosting with,

uh, maybe it was VIP or dot com.

Maybe neither, and they just had
WordPress, and they were doing a lot

of revenue with, with WooCommerce.

And, um, they just, like,
hey, we've, we've hit this.

Ceiling and now we're moving to
Shopify . It's just like, what?

This WordPress was great,
but it was a bottleneck.

And, and then we, we just, we
found this bottleneck and now

we're, we're moving to Shopify.

'cause obviously Shopify can scale,
but then you're locked in and then

when you wanna adjust in the future.

It's going to be more costly, more
challenging, and then God knows what's

going to happen with the platform.

Again, I know I'm biased to,
to WordPress, and this is sort

of like an education thing.

People just don't realize that things
can scale, and I'm sure there's

developers out there going, Oh, memory
buffer on MySQL eventually hits it.

Okay, I get it.

But at least people can come in.

And you can bring in hardware, you can
attach other solutions to WordPress, and

it's not just WordPress is the problem.

It's the hosting infrastructure
that probably you built it on.

And there's, there's ways
around it for, for most

Vik: people.

Yeah, absolutely.

I think that's a common problem where
I've been, I've been hosting for, I

don't know, 20 years or something.

And, uh, in a former life, we
did a lot of magenta hosting, you

know, magenta was open source.

And, uh, as Shopify became more popular,
uh, a lot of people had the same,

same concept where I say, Oh, well,
I'm running into these challenges.

So let me Shopify.

Uh, and you know, like I said before,
over, you know, X number of months

or a year or two later, they would
come back and say, well, this is.

Like this sucks.

Like, aren't there, aren't
there better solutions?

Like, can't I use woo and, and make
this work and how much can I scale?


And it becomes just a question of the
infrastructure you're providing it.

And that's where, like in
a case of pressable, right.

The infrastructure scales up.

And so we have restores, you
know, running millions of dollars.

Transactions to them with zero problems.

It all comes back to the
development of the store and

the infrastructure behind it.

Matt: Years ago, I made a lot,
not just me, but a lot of folks

predicted that hosting companies.

would be, it's obvious to say like
the future of WordPress, like the

future of way people experience
WordPress hosting companies would

have their own way of doing WordPress.

Just like you log into.

com and it has like this Calypso
experience or whatever they dub it.

I would have anticipated, you know,
making that prediction five, six years

ago that every time you logged into a,
uh, web hosting companies, WordPress

install, it would be just like built a
little bit different for that company.

Pressable might have their own onboarding
sort of way of, of, of going about

it, maybe even have a different admin.

Is that something that you, that you
think is important for WordPress to

continue to thrive, to have these
sort of tailored experiences or do

we need to keep WordPress true to its
core experience so that everyone knows

you're using a WordPress website.

Let's let's not lose the branding
and experience of WordPress by

making our own flavors of it.

Vik: That's a good question.

I think it probably depends
on who's actually using or

building the site, right?

I think in the case of a developer or
an agency with their developers that's

building hundreds or thousands of
WordPress sites, they probably want and

need the same exact experience everywhere,
where, you know, I think somebody brand

new to WordPress, uh, might benefit from
a little bit of a tailored onboarding.

And so I think it depends on which
profile of customer you're, you're

pursuing and trying to serve.

Uh, not that I think
the experience should.

Uh, be so different from core for those
users, but I think for somebody brand

new coming into it, it can be sometimes
a little challenging for them to say,

like, wow, there's a lot of stuff here.

Where, where do I start?

Uh, and helping them just get started
and learn a little bit, I think is, is

Matt: probably beneficial to them.


Publishing with.

WordPress is probably like true
to its core experience, right?

Starting as a blogging platform, then
turned into this sort of platform to

develop websites and applications.

Now all these other bespoke
different use cases for WordPress.

There's a pub and I'm gonna
forget the name of it right now.

There's a publisher solution
in Automatic as well, right?

Is it Newspack.


How do they interface
with, with you as a host?

Like, do you work with them to say,
Hey, let's go and integrate like this

newspa is that a flavor of WordPress?

Vik: Yeah, I believe it
is a flavor of WordPress.

I think it's a It's tailored
based on what their need is,

but they use pack essentially
runs their own hosting as well.

It runs on the same underlying
infrastructure as pressable and,

you know, dot com and others.

It runs on WP cloud, but I think
they, they tailor their products

specifically for publishers.

Matt: They have a hosting card.

They have their own hosting card.

Vik: Yeah.


Matt: think so.


One of the things that has been
challenging for some folks through like

publishing content right still in the
year 2024, you know, still wrapping

our heads around the block editor
full site editing that experience

of WordPress feels like it's taking
a while to catch up to competitors.

It's funny, W3Tex, maybe you saw this,
they do their annual report on like the

biggest, or I guess it's a recurring
data that just constantly updates,

but they put out their biggest CMS
for the year and it was Elementor.

And W3Tex is sort of like, WordPress
is, and I'm just paraphrasing here,

but they said, hey, it's hard to see
WordPress grow when they're already

at 60 percent of the CMS market.

So now we're just going to start
recommending, now we're just

going to start showing you like.

plugins that run on top of it.

Like that's how big WordPress has gotten.

Do you see any particular challenges
or is there a particular competitor you

have your eye on that has an experience
that you say, you know what, be great.

If, if we had.

A newspack flavor at pressable or, or
we went after site builders and we had,

you know, Elementor things you would do
with Gutenberg and full site editing.

Do you have like a competitor
you keep your eye on?

They say, boy, they do a great
and maybe we should just watch

them to see what they do.

Vik: So one, we would probably watch.

The entire market pretty closely, but I
don't think we look at it as a, let's go

try to mimic one of the site builders.

We're very focused on the developers
and agencies who probably don't

need a tailored experience, right?

A lot of a lot of our
agencies use Elementor.

Uh, and a lot of them use
half a dozen of the other ones

that exist out there, right?

And so for, because, because we're so
focused on serving agencies and those

developers today, we don't try to modify
the, the core experience for them, right?

We want to give them a unopinionated,
uh, version of a, of core so

they can build how they choose.

Matt: Yeah.

Is agencies the, is that the, the
sweet spot for pressable agencies?


Vik: it has been for a little while.

We've been focused on building
the product to serve their needs.

And you know, most of our growth
has come from that market in the

Matt: last couple of years, sell
to one customer, get many, uh,

approach, you know, and for that.


Vik: And I think from a service
and support standpoint, right, we.

We try to shine ourselves or, you
know, one of our differentiators

is we want to provide customers,
those agencies specifically with

the best possible support we can.

Uh, and so when we have a fewer
number of direct customers, uh,

we think we can serve them better
than, uh, trying to serve every

individual out there and letting those
agencies ultimately generate revenue

Matt: themselves.


Do you.

Aside from WordCamps, um, does Pressable
have a presence in any other sort of event

or media that is focused on, on agencies.

I've been hearing about CloudFest lately.

Are there other events that you,
you go to or, or how do you reach

these, these agencies aside from
the massive flagship WordCamps?

You know, I think a lot of

Vik: it is word of mouth.

Uh, we, we have sponsored some
smaller agency specific summits like

the, um, digital mastermind group.

Which is a it's a very small community.

I think there's 30 or 40 or so
agencies in there and when we do

things like that We we try not to be
the salespeople selling the agencies

instead We're really soliciting their
feedback and trying to understand

what their What their pain points are.

What are their business needs?

What are their developers need
so we can build a better product?

And hopefully that ultimately
leads to, uh, more agencies

finding pressable and using it.

But really, for us, it's about
research and ensuring we're

serving what they actually need.

Matt: You all jumping into the, it's
kind of comical to say this now, but in

2024, but are you jumping into anything
extra AI on the pressable platform?

That's not included
inside of core jetpack.

Uh, cause I know jetpack comes
with every, uh, account at.

But are you doing an extending
any other features with AI?

We haven't

Vik: yet.

We, we've been good, obviously,
just like everybody else.

We're, we're watching very closely.

Uh, but you know, a lot of the
use cases that we've seen, I

think others are serving, right?

Or like this.

Site generating, you know,
obviously creating content,

uh, AI site generators, right?

But we think the agencies should
probably pick and choose what tools

they want versus us Trying to be
super opinionated and dictate.


Hey, this is this is the thing now
maybe as You know, if they're become

clear leaders, those might be things
we partner with or bring in later.

But right now, uh, most of our
customers aren't even talking about AI

Matt: with us.


Still, I'm skeptical.

I only use it for some content things.

you know, pulling stuff out
of a transcript, summaries,

ideation, stuff like that.

I can't see it being a part of my website
generation process because ultimately

I just feel like I'm going to do, I'm,
whatever you make me, I'm going to change.

Like whatever it comes up
with, I'm going to change it.

I know it's supposed to get smarter and
better and faster and all this stuff.

Uh, but at this point
it's still not there.

What could be interesting from like
outside the box of websites for pressable

would be like AI that summarizes or,
uh, You can interface with customer

stats, you know, is there a trend here?

Where's the site?

Where's this data coming from?

Or where is the traffic coming from?

That would be kind of cool.

Hey, this little chat bot
that you can have with stats.

That's outside of the build
me a webpage kind of thing.

We're still early in 2024.

Is there anything that you have sort of on
the docket that's coming to the product?

Anything that you're excited
about headed into 2024?

Vik: Yeah, we've done a lot in the
last Six, eight months to help with,

you know, managing plugin updates and
adding our own little twister tag.

We think be helpful to, to customers.

But one of the things we're looking at
tying into that is security based updates.

So, Hey, there's a known vulnerability.

So only update those plugins for us.

And then other things that.

We were probably going to have in,
in the coming months where we're

going to improve our data sync.

So obviously staging the
production is a, it's a big deal.

So we're going to give people a
little more flexibility and, uh,

in what exactly is synced over
when, and that, that's a big one.

And then I think for some of the
agencies as a whole, right, there's.

We've agencies with thousands of sites
on the platform, and there are times when

they need to run an action across all
of their sites or a mass number of them.

And today that requires
them using our API to do it.

In a couple of months here, we're going
to give them a UI that'll let them do a

lot of those common things themselves.

Matt: Do you, do you have a,
uh, like a small use case,

like what that action would be?

Is it just updating content or is it?

I think

Vik: a simple use case is gonna be
like new, new core version comes out.

Today, Pressable manages that
core version update for everybody.

Uh, we let everybody stay on an old
version for, I think it's 30 or 60 days.

But in the case of a lot of our
agencies, they know 80 percent of their

sites are going to have no problem
with a, with an update to cohort.

And so letting them update that
80 percent with one click, uh,

will save them a lot of time.

And then they can go focus
on those other, other 20%.

The same for specific plugins, right?

They, they may say, Yeah, there's a,
there's a plugin they use across all

their sites and they know it doesn't
cause a problem for 98 percent of them.

So let them mass update those
things, things like that.

I think there's, there's a list
of probably a dozen items that

fall into that, that we're going
to roll out over the coming

Matt: months.

That's awesome.

That's cool.

And that's going to be
right into the UI, right?

Not like command line, so people
like me just melt my head looking

Vik: at it.

Well, it will be in
the API too, I believe.

So we, we try to, we try to
make almost everything that's

in the UI available in the API.

I think the, maybe the only limitation is
like updating your billing information.

Um, there's not much that's not available

Matt: in the API.

Very good.

Will Pressable have a
presence at WordCamp Europe?


Vik: don't know honestly well yet or not.

We're still debating.

We've, we've typically stayed at
WordCamp US just because of the

smaller team, but we're definitely
thinking about, uh, Europe and I'm

going to be at, uh, WordCamp Asia,

Matt: uh, this year.


We're rooting for you on the sidelines.

It's a, you know, it's a startup
within, within a startup.

And I've really enjoyed obviously my time.

And I'm not saying that because you
all are sponsors, but I've been using

it for, uh, using your platform for
a nonprofit site that I'm a part of.

And it's so easy.

Like the one click login saves my butt so
many times, uh, you know, like forgetting

the passwords that those, I know those
are simple things, but the UI is great.

And again, somebody who's been in the
host, ran an agency for a decade, was

in the hosting space, selling hosting.

I know.

how critical people can be just on
the, like the UI experience alone.

Like you'll have people tell you like,
Hey, you know, I remember being at

Pagely back in the day when it was God
awful UI and people were saying, when

are you going to update this thing?

Like we're, we're looking at competitors
and we're going to leave if you don't

give me like stats in a one click staging.

Um, But I also, on the flip side of
that, it's, it's not easy to just

like create and build this stuff and
integrate it into the infrastructure.

So I commend you and the team
for, um, you know, what you've

been doing with, with Pressable.

I think it's great.

Vik: Yeah, we appreciate
the, we appreciate that.

And the, the team works really
hard to bring a I think a world

class products to, to the market.

Hopefully it's a continues
to be easy to use.

And the feedback we get from our, our, our
current customers, future customers, and

even past customers is, uh, really helpful
to help continue, uh, refining products.

Matt: Some might say even
more enjoyable than dot com.

I'm just the one that's
going to say it, Vic.

You don't, you don't have to say it.

Vic, thanks for hanging out today.

Uh, it's been a pleasure meeting you
and uh, doing your first podcast.


Vik: for having me, Matt.

Matt: That's it for today's episode.

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