Michelle Zatlyn: Scaling Cloudflare to a $70B giant and building a better Internet

In this episode of Inside the Network, we sit down with Michelle Zatlyn, Co-founder and President of Cloudflare, one of the most iconic Internet infrastructure companies in the world. From its launch during the depths of the 2009 financial crisis to today’s $70 billion market cap and 5 million+ customers, Cloudflare has become a cornerstone of global Internet security and performance.

Michelle’s journey is remarkable. Raised in a small farming town in Saskatchewan, Canada, she left behind plans to become a doctor and instead teamed up with Matthew Prince and Lee Holloway to tackle an audacious question: “How can we build a better Internet?” Fifteen years later, Cloudflare is the third most valuable cybersecurity company in the world, protecting millions of businesses and powering the modern web.

In our conversation, Michelle shares what it really took to build Cloudflare, why grit mattered more than expertise in the early days, how deep trust among co-founders carried them through the hardest moments, and why “just ship it” became a guiding principle that fueled rapid growth. She also reflects on how Cloudflare has avoided the innovator’s dilemma, continuing to reinvent itself even as a public company, and how AI is reshaping the web, including why she believes we need a new business model to create the right incentives for content creators in the age of large-scale AI crawlers.

Episode Transcript

Sid Trivedi (00:04):
Welcome to Inside the Network. I'm Sid Trivedi.

Ross Haleliuk (00:08):
I am Ross Haleliuk.

Mahendra Ramsinghani (00:10):
And I am Mahendra Ramsinghani. We have
spent decades building,investing, and researching
cybersecurity companies.

Sid Trivedi (00:19):
On this podcast, we invite you to join us inside the
network where we bring the bestfounders, operators, and
investors building the future ofcyber.

Ross Haleliuk (00:31):
We will talk about the hard parts of the
founder journey, launchingcompanies, getting to product
market fit, raising capital, andscaling to an exit.

Mahendra Ramsinghani (00:42):
And, yes, we will also be talking about
epic failures.

Sid Trivedi (00:46):
But, Mahendra, we're here to make the founder
journey easier.

Mahendra Ramsinghani (00:50):
That is correct, Sid. But we cannot make
it too much easier becausestartups are hard, and, of
course, you already knew that.Alright, YouTube. Enough. Let's
get

Ross Haleliuk (01:00):
started with this week's episode.

Mahendra Ramsinghani (01:06):
Our guest today is Michelle Zatlin,
president and cofounder ofCloudflare, a global Internet
security powerhouse boasting amarket cap of $60,000,000,000.
While getting an MBA fromHarvard, Michelle teamed up with
Matthew Prince and Lee Hollowayto launch CloudFair. The three

(01:27):
of them had an audacious vision.How can we build a better
Internet? One that would keepthe bad guys out.
Today, as the company enters itssixteenth year of operations, it
serves over 5,000,000 customersglobally and generates

(01:48):
$1,700,000,000 in annualrevenues. Building Cloudflare
and leading its go to market isnot the only thing that keeps
Michelle busy. She's a boardmember at Atlassian, a fierce
advocate for women in tech.She's been named a young global
leader by the World EconomicForum, and Forbes recognized her

(02:11):
as one of the 50 self madewomen. In our conversation
today, Michelle talks about theimportance of grit and how it
has helped her to build such aniconic company.
More importantly, she talksabout the art of accruing trust
with her cofounders. Despitemany differences across sixteen

(02:34):
years, they are still together,working hard, having fun, and
their vision is still the same.How can we build a better
Internet? Now as we tackle AI'sopportunities and challenges,
Michelle shares some novel waysabout how Cloudflare is on the
forefront of innovations. Afterall, Michelle has not just read

(02:58):
Clayton Christensen's all timegreat book.
She actually took a class withthe professor himself during her
days at Harvard. This is acompany that will never suffer
from the innovator's dilemma,and Michelle will tell you why.
Let's get started.

Sid Trivedi (03:14):
Michelle, welcome to Inside the Network.

Michelle Zatlyn (03:16):
Thanks so much for having me. I'm thrilled to
be here.

Sid Trivedi (03:19):
Well, we wanna talk about a whole bunch of things,
and Cloudflare will absolutelybe in that conversation. But
before we get into to Cloudflareand the amazing journey you've
had, we want to start by talkingabout your early influences and
how you even got into becoming afounder. You grew up in a very
small town, Saskatchewan inCanada, and hopefully I
pronounced that correctly. Howdid that early environment and

(03:42):
upbringing in a rural townreally shape who you are as a
leader today? And did any ofthose early years influence, you
know, your drive to eventuallystart a tech company?

Michelle Zatlyn (03:53):
Yes. Yeah. No. Thank you. Yes.
I I grew up in Saskatchewan,Canada. It's a province, and
it's a pretty small province,about a million people across
the entire province. And thecity I grew up in was about
30,000 people. And so you don'tfind that many tech
entrepreneurs coming out of outof where I grew up, but that's
okay. That's okay.
And I think where you grow updefinitely shapes who you are as

(04:14):
a person. And so as I reflectback as my journey as a founder
and and kind of the connectionsto my upbringing, I definitely
see strong connections to thepower of community and the power
of hard work. Saskatchewan's afarming community and our
agricultural community. It'svery cold in the winters. And so
this idea of really had to workhard there both in the physical

(04:37):
sense of having farmland andjust doing a lot of things for
yourself, but also the power ofcommunity.
And I think that's actually beenamazing lessons as a founder
where today founders have to beable to work hard. Sometimes
that's maybe the only thing thatdifferentiates you. And so this
idea of hard work never scaredme of that grit, which I love
that word, but then howimportant people are and

(04:59):
relationships are. And so Iactually think, it wasn't
obvious in the moment, butlooking back, I actually think,
Saskatchewan was a great great,test bed for for being an
entrepreneur.

Sid Trivedi (05:09):
And was tech in any part part of that upbringing?
Was there ever any kind ofcomputers and tech, or when did
that influence get started?

Michelle Zatlyn (05:18):
Yeah. You know, I loved video games. So I had a
lot of video game consoles, andthen at some point, I wanted to
design video games. So I wasdoing that with the computers.
And so so, yes, my, you know, myparents were were were super
open about having you know, Iplayed a lot of games growing
up.
How about that? And, you know,this is, I guess, power of of
these programs. But even, youknow, my mom put me in junior

(05:40):
achievement after school when Iwas in, like, kind of junior
high. And these programs are itwasn't a tech company that we
built out of junior achievement,but it was this idea of taking
an idea, working with others,making it come to life, having a
business plan tied to it. And Ithink just getting access to
that was helpful.
Having said all of that, Sid, atthat point in my life, I thought
I was gonna be a doctor. So I,like, liked doing all that work

(06:02):
and all the projects andbuilding things and shipping
things. I love the satisfaction.But in the back of my mind, I
was gonna be a doctor. So thatwas, like, all just extra credit
sort of stuff for me.
I really ended up kindadiscovering technology. I mean,
I was in I went to university inCanada, so at McGill, and I was
in college when, like, the wholetech boom was happening in
Silicon Valley. It was and Iremember we got lapped. That's

(06:25):
when we were getting kindacomputers at school, and my
sister was doing her MBA out inSilicon Valley. She was at
Stanford at the time.
And so I kinda got a taste of itmore through her being here and,
of course, reading in the media.But I was I was going to
university at the time, and thenthe field started to burgeon
more. And so so I definitely nottied to my background, but it
wasn't like I had no idea. Butit just was kind of it was it

(06:47):
was just kind of exposed, butdidn't really think that that
was the one.

Ross Haleliuk (06:51):
Michelle, you you earned a chemistry degree at
McGill. So, I'm going to assumethat was still the time when you
were thinking about becoming adoctor. But then eventually, you
went into marketing, you wentinto product management, then
you did an MBA at Harvard andended up starting Cloudflare.
I'm curious, did you always planto start a company out of
business school, or did you haveother plans at the moment when

(07:12):
you realize that you're probablynot going to be a doctor?

Michelle Zatlyn (07:15):
So I like telling the story because I
think there's I've met so manyfounders over my life, and
there's a bunch of folks who,like, know they wanna start a
company. And I, like, love thosepeople, and I'm I'm almost
envious of those people who,like, have this plan. And it's
like they will stop at no endunless it works. That was not
me, Ross, as you just described,where I was more about open to
the opportunity. And I thinkthat there's a bunch of folks in

(07:35):
that bucket too where it's, hey.
Don't know exactly what I wannado and I'm open to different
sorts of opportunities thatpresent themselves. So I was
definitely in the open toopportunities that present
itself. So I did collect a lotof experiences. And actually,
think career should I thinkactually some of the richest
careers are where you collect alot of experiences. And so in
this kinda open to differentopportunities, I tried a lot of

(07:55):
different things.
I tried different types ofcompanies. I tried different
types of jobs. Some of thecompanies I joined were growing,
like, growth companies, and thatwas fun. There's others that
were losing market share. Youlearn a lot in those situations
too.
I tried different roles. And soI actually was really open to a
lot of different opportunities.And so in each one, I was just
saying, what can I learn fromthis? I knew it was it was not

(08:16):
where I was gonna end my career,but I was like, k. I'm here for
a couple years.
What could I learn from it? Andso two things. I wanted to be a
doctor because I really wantedto help people, and I really
wanted to be a doctor because Ithink the science, you're using
a lot of brainpower to solveproblems. Like, I love that. Why
I ended up falling in love intechnology is for the exact same
reasons, actually.
You work with really smartpeople. You work on really hard

(08:37):
problems together, so I lovedthat. And then the the second
thing is is I love helpingpeople at scale, and it turns
out technology can help peopleat scale. And so fast forward to
I didn't think I was gonna starta company out of business
school, but I was open to thatopportunity. And when this
opportunity presented itself towork with Matthew Prince and Lee
Holloway of saying, hey.
Could we create a service thatactually stops malicious actors

(08:59):
online, make it better foreveryone? The literally, litmus
test to myself is would I beproud to be part of this
company? And I said, wow. If Ican make the Internet a safer
place, a better place foreverybody, I absolutely would be
proud to be part of that. Andthat's kinda how the I traded in
my my lab coat for maybe somemore digital laptops, but gosh,

(09:20):
couldn't be happier.

Mahendra Ramsinghani (09:21):
And, Michelle, speaking of, you know,
what can I learn from theseopportunities? You once admitted
that you knew nothing aboutcybersecurity as you got
started. Now that requires a lotof courage, and and especially
speaking of courage and gender,you know, women also struggle
with challenges where they don'texpress themselves that boldly.

(09:43):
Take us back to that time. Tellus, you know, how you got up to
speed and what kind of thingsyou did to adapt to this new
world of Cloudflare.

Michelle Zatlyn (09:52):
Yeah. No. I think I did say that once, and I
kinda regret saying it becauseit keeps coming up all the time.
And I just thought it'd luck.It's not the perfect message.
And so it's so I was definitelynot an expert in this field. And
and so maybe the lesson learnedfor folks listening is I think
sometimes opportunities presentthemselves and people decide not
to take them because they'relike, oh, I don't know enough

(10:13):
about it. And I maybe maybe thethe the lesson learned is, well,
you should really challenge thatassumption. And I think what was
interesting in my situation iswhen we started to work on
Cloudflare, I was not an experton the topic of the subject
matter. I just wasn't.
But Matthew and Lee, my twobusiness partners knew a lot
about it. And it turns out thatI brought different skills to
the table. And so and I broughtdifferent skills to the table,

(10:36):
and then I was able to learn alot about the subject matter
expertise. And so, you know,over time, I ended up learning a
lot more about it. And now Iwould say I am a world leading
expert even though I didn'tstart as one.
And I think that this is one ofthose things where sometimes I
meet founders or people whoreally wanna start something,
and they only look for ideas orproblems to solve in spaces they
already know a lot about. And Ithink that's totally makes

(10:59):
sense. I also think it's okay ifyou surround yourself with
people who know a lot about itand you bring something else to
the table, that's an okay pathtoo. And I think that's maybe
the, something that doesn't getspoken enough about and that's
really that's the real insightthat I hope listeners take away.
That's why I told that story toencourage others, like, if you
don't know everything better,it's okay.
Still go for it. And actually,you know, even if you're not a

(11:21):
founder, I think about that evengoing to work at a company.
Sometimes it's like go work forthe place where you're you could
be proud to be part of thatteam, where you're gonna learn a
lot even if you're not an expertif you really want. And and I
think that that takes courage,back to your word, but I'm not
the only person in the worldwho's done that. And so what I
often end up saying is thatcuriosity or your rate of

(11:43):
learning actually ends up beingthe superpower.
How fast can you learn? And, youknow, I'm I'm sick of fifteen
year well, Cloudflare is turning15 years old this year. So I
kinda have this hindsight of Iwas the founder and and these
questions are bringing me backto those very early days. And
now today, we have 4,500 people.You know, we we did
1,600,000,000.0 revenue lastyear.
We're publicly traded. I havethis huge job, and I kinda think

(12:05):
about me today. And I think thatthe rate of what you learn
actually is the biggestsuperpower. If I could choose,
hey. Are you a really curiousperson with grit, but you don't
know everything about thesubject matter versus someone
who knows a lot about thesubject matter but doesn't have
the grit and isn't curious?
I would pick the first personevery day of the week. And so I
think that's one of thoseinsights that sometimes people

(12:27):
forget about.

Sid Trivedi (12:27):
I wanna dig in a little bit more on the
Cloudflare origin story. Youalready talked a little bit
about this, but take us back to02/2009. The the world's dealing
with a major financial crisis.There's a big question on
whether people will have jobs.And you cofound Cloudflare with
with Matthew and and LeeHolloway, and Matthew is your
classmate at HBS.

(12:48):
How did the three of you come upwith the idea for Cloudflare?
Was there an initial problem?Was it Matthew's project on you
know I I think he had a projectcalled project Honeypot that he
was working on with LeeHolloway. Was it a class project
you're working on at HBS? Whatwas the the inspiration for this
this idea?

Michelle Zatlyn (13:06):
Yeah. No. It's so interesting. There's lot of
things back from 2009 when wedid start to work on Cloudflare
that are really similar totoday. There was, like, a lot of
uncertainty.
There was a it had just beenafter the financial crisis of
two thousand eight. So it's kindof a heavy time in the market.
Was just a heavy time. It wasjust heavy. And there was also a
big shift happening, maybe notquite as shift as the AI shift

(13:29):
we're seeing right now, butthere was a big shift of the
rise of cloud computing andmobile.
So, like, that was definitelyhappening at the same time. So
what's interesting is what wesaw in the moment was back to my
business partners, Matthew andLee, they had co created
something called ProjectHoneypot that tracks spammers
online, and they were reallyproud of it. Matthew and I were
going to school together, and hewas just so proud of this

(13:51):
project. He was always talkingabout it. And so back to being
curious, at some point, I waslike, hey.
Just tell me what is this? Andwe had this exchange of there
was a a part of the market thathad a lot of web spammers coming
to steal resources from them,and there weren't good
solutions. And, like, the bigwas, could we create a service
that uses the threat intel data,the threat intelligence data

(14:13):
that we had at a projecthoneypot to create a service
that actually stops maliciousactor? That was the And we went
to work on it at a schoolproject. And so it became very
clear that there was a problemupfront.
We went and talked to thesesmall business owners and we'd
get answers like web spammersmake me believe in the death
penalty. Now that's a prettyvisceral reaction. If you don't
know anything about the problemset, you give somebody a survey,

(14:35):
you get that answer back, you'relike, wow. There's a real
problem here. So so it's veryclear that there was a problem.
And then the next set of kind ofthe conversation was like, are
you doing to solve it? And ifyou were a small business, there
were no good solutions. Everyonewas doing it kind of a Band Aid
solution. So this was kind ofthe insight of, hey. Could we
come up with a technicalsolution to solve it?
And if you're a big company, youhad big teams, and you bought a

(14:57):
lot of hardware box, buthardware boxes cost at least,
call it, you know, $25,000 andabove. And if you're a big
company, that makes sense. Butfor a small business, they
weren't gonna pay that. That's alot of money. And so it was
interesting in retrospect.
It was such a great timing. AndI think sometimes when there's
these huge shifts in the market,it's such great timing for new
innovation to happen. Andbecause of the rise of cloud

(15:20):
computing, we basically said,hey. Let's create a cloud based
service that almost like becomesa digital bouncer and a personal
trainer for the Internet whereit's, hey. We will make it we
will protect all of ourcommunity from the online
attackers and we'll share datalike a neighborhood watch and
we'll make it stop in real timeand at the same time make it
spiffy for all your legitimateusers.

(15:42):
And there was no competition forthe the segment of customers of
small businesses. There's justthere there was no competition
because there was nothing thatexisted. But then over time, the
idea was like, but over time, wecan use the exact same solution
to help solve enterprisesproblems in a cloud based way
versus hardware. And so it was ashift of this rise of cloud
computing of saying, hey. Wecould become this integrated

(16:03):
platform that allowsorganizations to manage be like
the connectivity cloud andmanage anything they need to
stop malicious attackers online,but make it better for all the
legitimate visitors.
Let's start with this onesegment of customers and over
time move up to serviceeverybody on the Internet. And
that was a huge audacious visionthat honestly we've had since

(16:24):
day one. And it was interestingas Matthew and I thought it was
awesome. We and Lee was thoughtit was awesome too. We're like,
let's go do it.
And some people who would meetwould be like, this is awesome.
Let's go. And other people wouldmeet and be like, you guys are
crazy. And what's interesting iswhen you're a founder, you're
like, which one is it? Am Icrazy or is it awesome?
And it's hard to know early onbecause early on, you know,
there's highs and lows 15 timesin a day. Lots of things are

(16:45):
going wrong all the time. Ithink today, fifteen years
later, I feel really good thatI'm so glad we took the plunge
and decided to do it even thoughit was an audacious goal from
day one, but we weren't sure itwas gonna work and neither was
anyone around us. And almostthose are almost always the best
businesses, the ones where it'slike, I'm not sure this is gonna
work, but if it does work,you're gonna create something
very valuable. Actually, that'sa really good litmus test for if

(17:06):
you wanna set out to dosomething big of, god, I don't
know if it's gonna work, but ifit does, this will be huge.
That's a good place to be. It'sscary, but a good place to be.

Sid Trivedi (17:14):
And I love your point around during the
difficult times, that's whengreat companies are created. And
for our listeners, just forcontext, like, 2,009, you had
Cloudflare was founded, Uber wasfounded, WhatsApp was founded,
Nutanix was founded. I mean, itwas a very, very interesting
time to to to be in the startupspace even though it was so
difficult.

Michelle Zatlyn (17:33):
Yeah. And you have to have conviction. Like,
there it was you know, it's oneof these things where you when
when when everyone else is notdoing it, you really have to
have conviction. And for us, wewere, like, really curious about
solving this problem. We reallythought we we were onto
something, and we just we hadthis we were like, we have to
see where this goes.
And so even though everyone'slike, you guys are crazy.

(17:53):
Grazing money is hard. You'renever like, it's so hard. You
kinda are like, well, we hadeach other. Like, we already had
three people.
Let's just keep going. Like,that's progress. Right? And and
then and so we just kinda saidwe we kept going. And so you
really do need to have theconviction because there's so
many reasons.
There were so many outspresented to us. But I think
that's why some of the bestcompanies get started there
because it's like you the peoplewho stick with it can really

(18:16):
create something valuable. Nowthere's also, I think, bias to
that. So that SACS, there's abunch of things that started
that didn't go anywhere. Butjust, you know, just to give the
listeners a sense of how hard itwas, that year, we raised some
money from Benrock, and we were,like, one of the only tech
investments that they made thewhole year.
So it's just like money was wasnot widely available, and it

(18:37):
just was a it was it was a hardtime, but we had real
conviction. We were like, we'regonna go see if we can make this
happen. And and gosh. Isometimes I think back, like,
what were we thinking? But soglad that we we we we just
didn't we had we didn't know anybetter that we're like, we have
to see.
There's just something inside ofus. And I think it's back to
this word grit of, like, okay. Ihave to see where this goes.

Sid Trivedi (18:57):
On that topic of the three of you, you, Matthew,
and Lee, Matthew's said thisvery publicly multiple times,
but he said, we wouldn't havebuilt a company without
Michelle. She actually kept thetrains running and made sure
that we were doing something.You described a little bit of
that in the in an, you know,earlier part of the session, but
just give us a sense for kind ofhow did you divide up roles
between the three of you? Whatwas what were you responsible

(19:18):
for? What was Matthewresponsible for?
What was Lee responsible for?

Michelle Zatlyn (19:22):
Yes. Yeah. And so it's interesting. Like, if
the people who knew Matthew,Lee, and I were like, oh, I
like, I it's very obvious whateach of you would be doing. But
to the outside, it's notobvious.
So it's a really good question,actually. And so I like the idea
of a Venn diagram. I think that,like, that is back to kind of my
geeky science, my bit math thatI at least love with math and
science. It's like the Venndiagram, I can think, is a great

(19:43):
description for a founding teamof we all covered a lot of
surface area, but we hadoverlap. I think overlap is
important for shared vision, andwe trusted each other.
And so Matthew is incrediblystill to this day, incredibly
talented on the strategy side. Imean, he's technical. He's a
great storyteller. Heunderstands strategy, and he has
and he has this insane businessbackground. And so he's really

(20:06):
good at the vision, thestrategy, almost like the 100
foot thousand foot view.
It's like we're going there. Andagain, we we are ambitious
company. We want to buildsomething iconic. And again,
back to when you started, thisis his audacious idea. He, like,
just lived in that all the timeand could paint the best picture
around it.
So he was extremely good atsaying, here's where we're

(20:26):
going. Lee was the technicalarchitect. He was the one
figuring out how like,technically, how you're gonna
architect this and testing webservers. And at the time, for
anyone in the audience who'skinda technical at the time,
like, Apache was the web serverthat everyone used, but NGINX
was just emerging. And at thetime, his then wife spoke
Russian, and she heard about iton the Russian forum boards.

(20:47):
And so he's like, hey. I'm gonnatry NGINX. And he's like, wow.
This thing is performing 10,000to one compared to patchy. We're
like, no way.
Anyway, these little things thatlike little series of smart
decisions that helped usarchitectural decisions that
helped us in the early days makea lot of progress. So Lee was a
technical genius behindCloudflare making, like building
this vision that Matthew wouldset out. And then I was really

(21:08):
good at at making all the otherstuff happen internally. And so
it's this idea of, like, vision,innovation, and execution coming
together. And, again, on dayone, I didn't have, back to this
point of I wasn't a subjectmatter expertise.
Matthew and Lee knew a lot aboutit, then other the the next five
people we hired knew a lot aboutit. But I was really good at,
like, almost like the glue thatmade it all come together and

(21:29):
saying, okay. If we're goingthere, first of all, it was fun
to debate the the big vision andbe a thought partner on that.
Okay. If we're gonna do that,here's all the things we need to
do to make it happen and theorder we should do it in.
Turns out that actually is animportant skill set early on,
you know, and and how we'regonna do it. What's it gonna
feel like? And so this is one ofthose things where you really
diverse teams are a better placeto work and drive the better

(21:51):
business results. And I thinkit's one of these things where
we just covered a lot of surfacearea. And then every day, I was
learning a ton about the subjectand how we're doing it and
spending time with customers.
And then pretty soon, you'relike, oh, wow. I know a lot, and
actually, I'm adding a lot ofvalue on that side too. But
that's how it started. And sothat's how it started. So we
really covered a lot ofdifferent areas.

(22:11):
Today, in case you're curious,fast forward early like, fast
forward today, I run all of thego to market teams. So I spend a
ton of time with our customers,our customer facing teams, and
then our people team. And,actually, those are the things
that I love. I love the people Iget to work with and what's it
like working at Cloudflare everyday and then our customers
experience. And then Matthewruns all of the product
engineering, finance, legalreport up into him.

(22:32):
So it's actually today makesit's a little bit easier to
understand, but early on, that'show it worked. And and, again,
if you knew all of us, the threeof us, those of people in the
world who know all three of us,they're like, yep. That totally
makes sense. But externally, itwasn't that obvious. So it was
it was we made a really goodfounding team.
You know, one thing I'll justsay one thing because this
actually doesn't come up veryoften and again for the audience

(22:53):
if you if you're starting acompany, especially because we
had such different skill setsAnd that is a strength a source
of strength, but it's actuallyharder for the first year
because you just see the worldvery differently. Like we and
and it was one of these thingswhere, again, you don't know
you're onto something. Again, 10times a day, you're like, are we
crazy or are we onto something?And you're not sure. And I think

(23:14):
that's common for most earlystage startups of like, oh my
god.
This is amazing, and we're goingout of business, you know, flip
flopping many times a day.Again, the the highs and lows.
So if you're in that moment, Iremember that being normal. It
wasn't fun, but normal. That'sjust what it is.
And there's been a lot ofwriting about it in the startup
world. And so what wasinteresting is that first year
where we were all committed tothe idea, and there are certain

(23:36):
things Lee cared about, like,getting the technical
architecture, right, andobsessing over that and Matthew
caring about the strategy anddoing the right things and
maybe, like, we gotta do allthese things to make it all
happen. There were like, thatwhen it all aligned, it was
awesome, but there was timeswhere it didn't align. And so
you really had to figure out, Idon't understand why you care
about that so much. And by theway, there's a thousand things
to do and time to do a 100 ofthem.

(23:56):
So it's not like you can sitdown and have these
conversations. And so I so whileI think diversity is this huge
strength of a founding team, itis also harder upfront. And so
you have to kinda go throughthose cycles of those moments of
uncomfortable where things areuncomfortable or tough. But if
you get through that at the end,you're like, oh my god. I
wouldn't go I I would have it noother way.

(24:16):
There's no one else that I wouldgo to that I'd that I'd start a
company with because, wow, wegot through all of that
together. So And sometimes thoseuncomfortable moments is what
bring people closer togetherboth as founders, but even at
companies. And I again, I thinkif you either are starting a
company or you're working at acompany or one of those
uncomfortable moments, like, getthrough to the other side and
then decide because it's almostin those moments that you learn

(24:38):
the most about people. Eventhough you don't wanna be in the
situation, it's almost like it'simpossible to avoid them. So
it's like, what can you learn?
Do you get closer? I stuck itout, and now I have a different
perspective than I did when Iwas in the tunnel. And so I
think that's something that alsodoesn't get stuck spoken about a
lot from about founding teams.

Mahendra Ramsinghani (24:58):
You know, Michelle, as you talk about both
what Matthew's role has been andcontinues to be as well as
Lee's, what I find veryfascinating is the way all of
you have this mutual trust andrespect for each other. I mean,
here, Sid described how Matthewspeaks about your role being
sort of the glue. You speakabout Matthew. I think this is
also very rare of how thefounding team has this immense

(25:21):
amount of trust and loyalty andthese deep bonds built with each
other. Can you share a nugget ortwo on how can this muscle be
built?

Michelle Zatlyn (25:31):
Yes. Trying to think about what's a good how do
you make that because, again,our situation will never happen
again, but everyone has theirown situation. What's some just
good kinda lessons learned thatmight be practical? So I do
think that there's these thingsin the moment where the Silicon
Valley where we came to startCloudflare, and we're a very
global company today, islittered with stories of

(25:52):
founders no longer speaking toeach other, VCs and founders
going to battle with each other,and boards and founders getting
sideways with each other. Andfifteen years in, I understand
how every single one of thosehappen now because it's like in
a stressful situation, someonelooks the wrong direction in the
board meeting and all of asudden it spires off a thread
that, like, sets into a set of,I don't know, situations that

(26:16):
you were like, wait.
Well, how did that happen? Andso if you know, you know what
I'm describing. And for thosewho haven't been there yet, once
you're in it, you're like, okay.Now I understand what Michelle's
saying. So anyhow, so it's soit's you just there you find
yourself in situations you neverthought you were gonna be in.
And what you're gonna do in thatsituation, it's so easy to say
ahead of time, but it's reallyactually hard when you're in the

(26:36):
situation. There's, like,emotions involved and, like,
when do you say something? Whendon't you say something? When do
you when do you make it a bigdeal? When do you say, okay.
Fine. I disagree and commit.Like, there's just, like, I'll
like, there's tons around it.And so look. We were we're not
perfect.
So it's the bar is notperfection. I think one of the

(26:56):
things that really worked reallywell for Matthew Lena is we
really did have a shared visionof what we want Cloudflare to
be, and we really felt like wewere all in it together. That
doesn't mean we didn't disagree.That didn't mean we didn't
sometimes annoy each other, butwe were like, we were all in it
together. And there was no, god,if you do that again, I'm out of
here.
Like, there was never any ofthat. And, you know, I'm now

(27:18):
married. And so I think it'skinda like marriages too,
although I don't I don't know ifmarriage advice should get when
I we need a whole another,section about that. It's just
kinda like it's relationship.You treat people how you wanna
be treated and that sometimesyou're annoyed.
Sometimes you have to let thingsroll off your back. Sometimes
you gotta act like a like you'redeaf. Like, there's lots of
different things that you do tocope through it, but it for us,
the north star was what's bestfor Cloudflare. And I think that

(27:40):
that back to that's the bestthing. And there have been tons
of moments where in the moment,emotionally, might have been
like, oh, I wanna say this or Iget my words in.
But then after the fact, you'relike, actually, god, it just
doesn't even matter inretrospect. Thank god I didn't
say anything. So I think thatthat is I think maybe the ease
like, in terms of instead ofreliving our our moments, was

(28:01):
just kinda like the lessonslearned of what's in North Star?
Do you trust each other? I'vealways trusted Matthew and Lee.
And there's been many timeswe're back to, like, in that
moment in the boardroom wheresomeone looks at you a different
way, like, we just we time andtime again, we kinda made
decisions that accrued trustdidn't erode trust. And so when
you are facing that decision,which you will, you'll feel like

(28:22):
it's unfair. Sometimes you'reput in a situation that you're
like, this is so unfair that Ihave to even have an opinion on
this. Make the decision thataccrues trust towards your your
business partners and yourcofounders doesn't degrade trust
because those are things thatyou like, regaining it if you
you pick the degrade trust pathis is basically, I think, a

(28:43):
nonstarter. So I think that'smaybe some of the lessons
learned, Mahendra.
I hear some I I I know theaudience's audio, but I see some
heads nodding. I I think there'sprobably some heads nodding on
the other side of the audio.

Ross Haleliuk (28:54):
Yeah. There most definitely will be. Let's go
back, to the Cloudflare's earlydays. So in the Cloudflare's
early days, there was a debateabout whether the product was
ready or not, and you basicallytold the team, just just ship
it. Then Cloudflare ended uplaunching at TechCrunch Disrupt
in in 2010, and and it won thecompetition.
You guys won, and sign ups tookoff immediately after that. Talk

(29:17):
to us about that time. Talk tous about your decision to
embrace the freemium model,which was very unusual for a
security product, and alsoabout, just how the this whole
ship it strategy and thefreemium approach, contributed
to your initial early growth.

Michelle Zatlyn (29:35):
Yes. Yeah. Well, so it's so interesting.
The, like, just ship itmentality, like, a 100 Matthew
Prince. Like, he's just, like, amasterclass at that.
And so so lucky to have him as abusiness partner, as our CEO.
And he really early on back inthe very early days was, let's
start getting customers using itand feedback. And I was more on

(29:55):
the side of I was, not more. Iwas on the side of events of,
oh, it's not ready yet, though.This is embarrassing.
And and, again, it's back to thethousand places of the duke it
out and debate it. It's like,No. Disagree and commit. Fine.
Let's ship it and see.
And when we shipped it and see,I disagreed and commit, but I
was, like, embarrassed. I was soembarrassed, so embarrassed by
what we were shipping. And itturns out Matthew was right. And

(30:17):
the story I like to give is, ortell is we one of the things
that the first version of theproduct didn't have was
analytics. So we were shippingthis thing, but it didn't really
tell anybody what it was doing.
So we were shipping a productthat helped stop threats coming
to our customers' websites andapps at the time, and we said we
were gonna speed it up. And wewere speeding it up, but we were

(30:38):
one of the things that wasn'tready for this, you know,
artificial deadline we'd put outthere was the analytics weren't
there. So I'm like, oh, so we'regonna give product our customers
a product but not tell them whatit's doing? I just thought that
was really at the time, I wasconvinced that was a terrible
idea. So this is again where,again, Matthew was right.
I was wrong. We put it outthere, and it turns out our
initial customers are reallytechnical. They had ways to

(30:58):
measure it. So they were writinginto us quickly overnight
saying, oh my god. Thank you somuch.
I love being part of the beta.This was the first night my
pager hasn't gone off in fiveyears. I had a full night sleep.
Or someone else sent us theirserver analytics from their
server side saying, oh my god. Ican see how much the caching is
helping.
Look at all this load you'vetaken off my server in just a

(31:19):
few hours. So it was almost likeour product didn't have
analytics, but our our customersdid, and I had totally missed
that. It seems obvious now. I'membarrassed that I'm telling
this story, but these are thingsthat weren't obvious in the
moment. And so it's one of thesethings where it was actually a
great lesson learned of actuallygetting it out there.
And sure, would have it workedfor financial institutions?

(31:40):
Absolutely not. But they weren'tthe ones that we are looking for
in the early days. And so it wasone of these things that we let
people self select in that wannabe part of the early product
feedback and help shape theproduct road map. And so this
idea of innovation, going fast,finding the right early adopters
to help shape the product andget feedback, and then you can
add in all the features afterand kind of work your way up to

(32:02):
folks who need it more fullyfeatured to complete is a really
great strategy.
And so I was again, there's lotsof parts of the story you
forget, but this early on memoryand so there's really two things
of, like, picking a launch dateor a date that you can't move
actually is super motivating fora team because you're just like,
you're gonna ship it. Otherwise,you just wait and wait and wait
and wait. And so today, how thatgets manifested in Cloudflare is

(32:24):
we have these innovation weekswhere we say, hey. This week,
we're gonna do innovation week.And so our product and
engineering team kinda say,okay.
We gotta we have what are weshipping for innovation week?
And, like, the innovation weekdates aren't moving. They're
set. So it's like, what? You'reeither in the innovation date
week or you're not.
Your thing is in or out. And itit really becomes, okay. What do
we need to do to get done? Whatdo we have to get done to be in

(32:45):
for the dates? And it becomesthis, like, nothing motivates a
team like a deadline you can'tmove.
And so I think, like, that'sjust because otherwise, the
human tendency I find is to bewait, wait, wait, wait, wait
until it's got enough. So we'vekind of flipped it, say, here's
the date you're either in orout. And and then we have
several of these dates. And soit's been it was a good lesson
learned early on, Ross, but ahard one, but a good lesson

(33:08):
learned that I'm happy. Sothat's that's on the innovation
side.
And to to this day, we careabout innovation, getting stuff
done, small incrementalimprovements, getting it onto
the hands. Because today, wehave over 5,000,000 customers
using Cloudflare. Like, we justhave a lot. And so even on day
one, if they don't all adoptsomething, if you get 1% of
that, that's still a lot ofpeople using it. And so it's

(33:30):
like, how do you if our missionis to help build a better
Internet, even if you're makingit better for some small
percentage, it's still a lotbecause Internet's a big place.
There's a lot of people usingit. And so we're constantly
saying, get it out there, getsome people using it, and then
work our way up. And I thinkthat's been a great secret to
our success. I think the freecustomer is a whole other
business strategy, we can talkabout that next. But for us, I

(33:51):
think Clay Christensen was anamazing professor for us at
Harvard Business School, and hehas a really famous book called
the innovator's dilemma.
If you are thinking aboutstarting a company and you have
not read this book, you shouldread it. It's really, really
good. It's how how do you gocompete with somebody who's
already in the market? How doyou carve out your space in a
market? Even if you're atechnical founder, I think you
should read it even faster thansomeone who's not a technical

(34:12):
founder.
It's just like the business sidewe found very helpful. And so
the whole point of Cloudflarewas how do you open up the
market? And opening up themarket meant how do we go serve
a part of the market that had nogood alternatives at the moment?
And at the moment, nobody washelping small businesses. We
started there.
And, again, over time, the smallbusinesses didn't have big
budgets or technical folks. Wehad to have the right price

(34:32):
point. Free sounded like a goodone. We needed a bunch of
traffic to do things to buildout our network and a lot of
other things, and it became thisbusiness strategy reason of why
we do it. Fast forward, we wentpublic six years ago.
And if you read our s one, wehave a whole section of our s
one of why do we why do we serveeveryone, which is another way
of saying why do we have a freeservice? And there's actually
six amazing, like, strongbusiness strategy reasons as why

(34:56):
we have a free plan, and itreally helped us build the
company in a way that wascapital efficient and smart in
my opinion. And I would a 100%go back and do that again if I
could if I was startingCloudflare from scratch. And so
those are those are kinda theanswers to two of your
questions.

Mahendra Ramsinghani (35:11):
You know, that's a fantastic, you know,
journey that you've been on. Andnow as you head up, go to
market, Michelle, obviously, youstarted with the freemium
package, and now you've moved upthe stack in terms of
enterprise. Now many startupsstruggle with these transitions
or sometimes just fall apart.What were some lessons that you

(35:33):
learned? What are some tacticsthat you used as you sort of
moved up the enterprise?
I'm sure today Wall Street has,you know, relationship with
Cloudflare. And and how do youmake sure that those are being
sold well?

Michelle Zatlyn (35:45):
Yes. Well, okay. So I'd ask if you're
asking if you're a founder inthis situation, I like, what I
always like to I always find itreally helpful to talk to those
founders ahead of me. And Iremember a few years ago, I was
at, getting an an a nice I'm aCanadian, and I was getting a
nice Canadian entrepreneurshipaward, and Stuart Butterfield
was there. And and he, at thetime, Slack was further ahead

(36:05):
than Cloudflare.
And and I remember him tellingme I went to every time I meet
somebody ahead of of me in thejourney, I'm like, go and ask
them the thousand questions andlearn a ton from that. And I
remember Stuart the time saidsomething that really was
exactly what I need to hear atthe moment was like, we do it.
His point he said wasparaphrased. What I remember him

(36:26):
saying was something like, oh mygosh, like and Slack was like
the hot company at the time,like very hot at the time. It
was before the Salesforceacquisition.
Like, they're just it was a veryhot company. And they were
growing like a weed. The numberswere crazy. And he's just like,
we are terrible at so manythings. And I just was like, but
you're winning and you're likeyou're the hot company.
He's like, we are terrible at somany things. And so another way

(36:46):
to think about that is you onlyhave to get a few things right.
And so to your point about whatif you're a founder and
listening to Mahendra's questionaround, hey. I've tried to go up
market and it didn't work. We'lltry again.
Like, and again and again andagain and again. Like, that's
all part of it. And of course,try and do it smarter and better
the next time and what did youlearn? But, like, it's there's

(37:09):
lots of things. I was talking tosomeone early at Salesforce and
again, this person told me atthe time about, oh, his exact
what he shared to me at the timewas Salesforce tried three times
to go up into the enterprisebefore they got it right.
I was like, really? Like, today,would definitely think of them
as an enterprise company, butyou kind of forget. You forget
about these things in themoment. And so and and there's
lots of other folks you meetthrough the days that you hear

(37:32):
these stories. And so so numberone is, are you actually solving
a problem in the market for yourcustomers?
And that's why I love talking tocustomers because if they're
like, you are making my lifebetter and here's all the ways,
it gives you the confidence togo try again of like, okay. It's
worth all the hassle to go tryit again and the hard work. And,
oh god, why do we do it thatway? Okay. Next way, let's do it

(37:53):
this way.
Oh, it worked a little bitbetter and whatnot. And then
knowing other people didn't getit right all the first time
either, it's kinda okay. And soI think that there's listening
to customers being obsessedabout, like, are you actually
solving a problem for them? Ifyou actually are solving
problems, you can go you havemore swings at the bat to figure
out all these other things thatmaybe didn't work out the first
time and just know that you'renot the only company that didn't

(38:15):
work out the first time. And Ithink sometimes we forget that
part.
So I think those are some of thethings that I have taken away.
And so as I think aboutexpanding the types of customers
we expand globally, I mean, I'mso proud that we are. We are a
very global company, and we workwith lots of we work with the
largest organizations in theworld today, governments. I love
that as well as small businessesand developers. I think it's so

(38:37):
cool.
Like, I think it's reallyamazing. And anytime something
isn't working, what we've reallyhave developed at Clever, and
again, this is as a family, youreally have to develop it. This
just doesn't happen, is to be aplace where people said this
didn't work. Okay. Why didn't itwork?
What's not working? What are wegonna do about it? And actually,
if you can be a place where yourteam can surface this isn't

(38:58):
working, okay. Why isn't itworking? What's the plan to
address it?
If you can admit thatsomething's not working, you can
always build a new plan toaddress it. And and I think that
that was not something that wasobvious to us when we started
Cloudflare. But as we scaledCloudflare, that's actually
maybe one of the best lessonsI've learned. And having board
members who are okay with that,who are like, oh, yeah. Great to

(39:20):
know that didn't work.
Glad that you have a new plan totry again because if you we we
know it's not working and you'retrying it a different way,
chances are you're gonna be moresuccessful that time versus
hiding it. And I think, like,you asking yourself as a leader
of a company or working at thecompany, is your company a place
where you can bring things thataren't working? And then it's
like, okay. What are we gonna doabout it versus a place where it
gets hidden? Again, I wouldrather be at a place where those

(39:43):
things can get surfaced.
Sometimes it's like, okay. It'snot working, not important right
now. Let's just leave itbecause, again, there's always
more things to do than time todo it. But some of those things
like, gosh. Thank god you'resaying that.
We gotta fix that right now.What are we gonna do about it?
Get the right team together anddo it. So those are some of my
insights that I would share.

Mahendra Ramsinghani (39:59):
I think it's a classic definition on
grit.

Michelle Zatlyn (40:01):
I love that word. Back to grit. I think it's
a good word. I know it was ithad a moment. It's kinda
disappeared, but I think weshould bring it back.

Sid Trivedi (40:07):
We wanna talk a little bit you know, we we
talked a lot about Cloudflare'sorigin story. Let's talk about
Cloudflare today, you know, as aglobal company. Today,
Cloudflare is the third mostvaluable cybersecurity company,
just shy of 70,000,000,000 inmarket cap. So you're in a very
different stage today fifteenyears on. One of the biggest
conversations in technology isaround AI and how it's gonna

(40:29):
impact the future.
And on July 1, so beginning ofthis month, Cloudflare announced
a one click feature, whichallows its customers to block
known AI web crawlers bydefault. And it basically also
allows them this opportunity topay per crawl to these, you
know, AI web crawlers. I'mcurious, like, what prompted
that? How do you seeCloudflare's role in important

(40:52):
issues like this, the the issuebetween balancing innovation
with content creator rights?

Michelle Zatlyn (40:57):
Yes. Yeah. No. AI. Well, I'm impressed we've
gone this long without the wordAI coming up.
So AI is reshaping everything. Imean, it is as big as the
invention of the Internet.Although, I think sometimes we
our generation doesn't exactlyknow what that means. So they
what I like to is it's as big asthe invention of electricity.
You know, most of us weren'talive when that happened, but
it's like, oh, I could imagineit kinda started as this kinda

(41:19):
spark.
And now you think about, well,on a daily basis, what does
electricity do for us? And Ihonestly think it's a great
analogy for AI. It is it's asignificant huge change, and
we're early, early, early on. Soit's, you know, ten, twenty
years from now, it's gonna bevastly different, and and it's
definitely not going away. Soit's just like a big moment.

(41:39):
And so anytime there is a bigmoment, it just creates huge
opportunity as well as it'sgonna cause hardship too. And so
there's gonna be challenges tiedto these big shifts, but there's
huge opportunity. So I I am I'm,I know there's a lot of
excitement and hype around it,but I think it's warranted. It
won't all work out, but it is abig deal. It's here to stay.
So so that's just on the AIfront. On the on the on what we

(42:03):
did on July 1, it's tied tothat, but slightly different.
And so what's interesting is theweb has been changing. So the
Internet's been around forthirty years. The web's been
around, and we've really, like,as a society, really used it for
the last twenty, twenty five.
Like, it's become and it'sbecome more important to our day
to day lives. And if you thinkabout kinda how the business
model of the web has worked thelast twenty years, this was,

(42:23):
hey. Google, company calledGoogle, went and searched
invented crawl, and they wouldsay, we would go to Google to
find stuff, and then they wouldsend traffic to the content
providers. And so, basically,Google helped people find things
on the web, and this idea ofcontent creators could create
things and get traffic, andthere was kind of an exchange of

(42:45):
the business model. What'shappening with AI and the
crawlers is that now more ofthat information is happening
right in the moment.
It's they're not actuallysending the traffic back to the
content creators. Well, it'skind of a problem. And maybe you
don't feel like that's a problemtoday, but if you keep playing
it out back to a strategyperspective, it's like, well,
why would anyone wanna evercreate content if they're not
getting paid for or gettingtraffic for eyeballs if it just

(43:08):
stays within someone else? It'slike, doesn't make sense. And so
it's if you look at some of thedata, it's really crazy where,
like, at first, basically, like,ten years ago, for every time
Google used to crawl someone'swebsite, they would send a
visitor.
They would refer a visitor backto that site. So it's kinda two
crawls to get a visitor. That'sa pretty good trade. You're

(43:29):
like, that makes sense. Today,it's about 18 times they come
crawl your site and then theysend somebody back to your site.
If you look at the AI crawlers,like, and again, whether it's
Anthropic or OpenAI, and again,I love these services. I use
them all the time too. Somethinglike OpenAI is crawling your
site 1,500 times, and the thedata's coming back out in
ChatGPT, and maybe they refer avisitor back once for those

(43:52):
1,500. I get it. OpenAI serviceis amazing.
ChatGPT is amazing. It'sawesome. But it's hard to see
why the content creators wouldstill create content. And then
that puts the web at risk.Right?
Like, that just puts thefundamental. And so and if
Cloudflare's mission is to helpbuild a better Internet, I was
like, is there something here?And so fast forward, what we
said is, hey. Look. It should befine.

(44:12):
The crawlers go crawl as long asthe content creators want it. So
more of a permission basedapproach versus versus by
default. And so that's reallywhat changed overnight. That if
you're a Cloudflare customer,you can say, yes. I permit these
AI crawlers to come to my siteand take the content because I
want to be in the models or no,don't.
And if I if you do, I want toget paid for it. And so almost

(44:32):
like a business model tied toit. So it's early days. I
believe this is really importantfor the next thirty years of the
web to exist, and and I think italigns the interest of the
content creators with the AIcrawlers, with consumers. And
there's gotta be a new businessmodel saying, well, if you're
building really valuable contentand I'm using it for my models
and people are using it in myproduct to get it, yes, you

(44:54):
should get some share back forcreating that.
And so we were just in a placeto both to give the visibility
of both the threats that come toyour site, but it's also, hey.
Now here's the invisibility ofthe AI crawlers coming to your
site and then deciding, do youpermit them to come? And if you
don't permit them and if you dopermit them to come, do you
wanna get paid for that in someway and helping create this new
business model? So it's earlyinnings. It's amazing to be part

(45:17):
of the conversation and to beable to talk to both the AI
companies and the contentproviders.
But I do think it's reallyimportant that all these sides
come together because we'velearned a lot the first thirty
years of the Internet, and we'reit's not going away. It's only
becoming more important in theworld of AI. And so I do think
there needs to be a new businessmodel for the next thirty years
or at least ten years so that wecan keep a lot of the greatness

(45:40):
of the web that we believe inwhile having these new services
and products, flourish too. Andso that's a little bit more of
the strategy beyond that, andthat that needs to be its own
podcast with Matthew at somepoint. This is just, again, back
to the strategy, the vision.
He he's got so much to say onthis topic.

Ross Haleliuk (45:57):
Talking about the future and preparing for the
future. Since Cloudflare's IPOin in 2019, the company has
scaled massively. It it now hasdata centers in over 300 cities,
more than, 4,500 employees, andalmost 5,000,000 customers of
each, like, I believe over over200,000 paying customers. How

(46:17):
have you approached scaling theorganization and the leadership
team, and how are you thinkingabout it looking at the next ten
years for Cloud flare?

Michelle Zatlyn (46:24):
Yeah. Well, yes. This is one of the lessons
learned. People are everything.Everything.
I mean, it it's it is peoplematter so much when you're
building a company. Now there'ssomebody on this call list,
though. There's definitely lesslisten listener thinking, well,
I'm gonna build a companywithout employees, and and that
is definitely possible too. Thatis absolutely possible too. But
then you matter and then maybeyou have a couple of cofounders

(46:45):
and you're still people.
So it turns out like the peopleare everything even in an
agentic world. People there'ssomething behind the agents, and
so people still matter. Andthere's such a big difference
between great and good. And I I,you know, I I just it's the same
in anything. There's just somethings in life where, like, this
is just an an amazing hire and agood hire.
And and then and then there'sthe bad. But, you know, bad, you

(47:08):
just can't tolerate in a highgrowth company. But the as we've
scaled as having the rightpeople both at the company and
the leadership roles, when thatis when when that is in flow or
working or vibing, I guess theword right now would be when
when that is in vibe, you can doanything. You real like, you
feel like you can do anything.And and when it's not inflow or

(47:29):
not vibing, it just sucks up allyour energy.
And I think that it's it'ssomething that, you know, I read
a lot of the again, I I've I'vescaled my business, and I've
I've read so much. I've listenedto so many podcasts. Hate to
learn from those ahead of you,and this is like one piece of
advice that always comes back.You know, like, my god. I've
heard this so many times.
Well, it's still in voguebecause it's just so true. Like,

(47:49):
you have to have the rightleadership team and the right
folks on the team who can set upto get stuff done because at the
end of day, that's like whatcompanies are. And so I think
that matters a lot. And so justsome some, I don't know, maybe
lessons learned that some of myscar tissue that I can save from
others is I do think that with aleadership team, they go through
different you know, you you gothrough different versions of

(48:11):
your leadership team, naturalnormal course of business.
That's it's just they're allthat's a natural normal course
of business.
You don't think of that when youstart a company, but it is. The
people you start the journeywith aren't the people you're
gonna end it with. And so reallyit's about how are you gonna
manage it? So I think first one,being aware of it. Just being
like realizing natural normalcourse of business, okay to have
different levels of leadershipteams or versions of leadership

(48:33):
teams.
And when your current versionmaybe isn't working anymore, how
are you gonna deal with And Ithink being a place where I look
at somebody like a Shopify wherethey talk about these three
years tour of duties, where itgives them an opportunity to go
back and say, hey. Are wesigning up for another three
years? Are you signing up foranother three years? Actually,
it's a really smart way to have,like, make it a conversation and
make it a two way conversationand maybe a bit more human way

(48:55):
to handle different versions ofleadership teams and folks,
within a company. So I actuallythink what Shopify did is a
really interesting model thatmight work for some folks
knowing that it's a naturalnormal course of business.
And maybe it's these thingswhere you're like, how do you
thoughtfully make sure you havethe right leaders at, like, at
your company? And when it's timeto say goodbye, how you're gonna
do it? And and and again,there's lots of different

(49:17):
flavors of it. You're gonna haveto decide what you want for your
company. And I think when youfind a version that works, it's
not it's never really fun sayinggoodbye to folks that you've
worked with for a long time, butit does make everyone feel
better about it.
And then they leave and they endup being champions, and they're
like, I'm forever a champion.I'm so proud that I played a
role in that part of thecompany. And I think that that's
great. And there's so manycompanies that have that legacy.

(49:39):
And and I think at Cloudflare,we really strive to be in that
bucket of just saying, hey.
You you thank you for all yourcontributions. We wouldn't be
where we are without you. Can'twait to see what you go do next,
and you want them to go doamazing things. Right? You want
a diaspora.
That's amazing. And so I thinkthat's something that's
definitely come out. And thenthe second thing is just early
on when you're a start up, youhave to just get stuff done.
Like, otherwise, you just don'texist as a business. But what's

(50:02):
interesting is you scale and getbigger, you actually lose that
muscle.
And it's often because you bringin folks who have really great
resumes, and you're just like,these people are amazing, and
they're amazing at planning, andthey put these project plans
together and models that are,like, beautiful. You're like,
these are incredible. Butsometimes, not always, sometimes
those people actually can't getthings done. They just like
build the plan. I'm like, okay.
Did we do it? Oh, we haven'tdone it yet. Well, okay. I love

(50:24):
that you have a big beautifulplan, but it actually has not
made the business better todayor made it better for our
customers. Like, let's getgoing.
And so, you know, I wasn't inthat meeting and I don't know
the story, you know, there'sthat infamous story about Elon
Musk saying, like, get theshovel and start digging this
afternoon. I kinda get it.Sometimes I'm in a meeting. I'm
like, oh, I don't like, let'sjust get going. Let's just get
going, and we'll learn morealong the way.

(50:47):
Because when you build a plan,there's all these assumptions,
and it's just hard to predictthe future. It's just almost
very hard. You can have adirection, but you just don't
know how everything's gonna playout. But when you're in the
moment, you have moreinformation, you're learning,
and you can decide how to dealwith these things that come up
versus on paper. And so thesecond thing I would just say is
a company's ability to get stuffdone is in is is what sets great

(51:11):
companies apart from goodcompanies, and that doesn't just
happen.
Most things go to status quowhere it's like no action, not
getting stuff done. And so as aearly stage company, you have to
be able to get stuff done.Otherwise, you don't exist as a
business. But as you transitionto a business, keeping the sense
of urgency, momentum, gettingstuff done, shipping things,

(51:32):
those are the ones that the thescale companies do really well
versus the ones who I think endup languishing. And and that,
the the, my experience is thattakes a lot of energy to get a
company to do that.
But if you get that going, itjust feels so good because then
you attract people who wanna bedoers and get stuff done and,
like, find ways around theobstacles that come up versus

(51:53):
the folks who are just talkersand advisers. And so so I love
being a company of builders anddoers, and and those are the
people who do best atCloudflare.

Sid Trivedi (52:01):
We're getting towards the end of our
conversation. In the lastquarter, we wanna really talk
about reflections and advice forfounders. And, obviously, this
is the fifteenth year ofCloudflare since its founding.
And we've talked mostly aboutall the success, all the things
that worked out and everything,you know, went well. And what
many founders, particularlyfounders who are starting off,

(52:22):
realize is there's all these upsand downs in building companies,
and I'm sure that Cloudflare hadlots of difficult moments.
Could you give us a story, justone story, you know, where where
something critical wasn'tworking out, and you really sat
down and you said, this might beit. We might not make it. And
how did the three of you goabout overcoming that problem?

Michelle Zatlyn (52:42):
It was so there's so many times that were
hard and in the not fun categoryor might not like, the stressful
the the stress of trying tobuild something. And I'll just
tell a story where, you know,I'm very shiny and positive and
happy right now. And, of course,that's part of my job is to tell
these stories that are energeticand make someone feel like, if

(53:04):
she could do it, so can I? AndI'd rather be that person that
just sits here and tells you allthe hard things about it. But
maybe maybe I should try thatsometime.
But I remember it was early on.It was four years into
Cloudflare and somebody aprofessor from Harvard Business
School was in San Francisco.We'd organized dinner. And
again, we were we were so early.Like, I think we had a 150

(53:27):
people at Cloudflare at the timeand we had raised money.
And so things were going well,but I went to this dinner. I sat
down at the dinner. I was notthe happy shiny Michelle that I
am right now, and I was like, Idon't understand why anyone
starts a company. This is justso hard. Like, I should
definitely be working somewhereelse.
I'd be, like, less stressed andmaking way more money because
four years into Cloud Vartoya, Iwas not making very much money.

(53:49):
And I just was kinda beaten up.I was just tired. I was tired
and lonely. And and I and now Iunderstand why early stage
founders are often depressedbecause it's just hard.
And, again, it was four yearsin, three, four years in. And so
I was at this dinner, and Ithought I was being vulnerable
in the moment. And, you know,you can't be vulnerable to to
your team. And and maybeMatthew, Lee, and I had that
relationship. But, you know, ona daily basis, you wanna bring
that to work.

(54:09):
You're there trying to solveproblems. But I was at this
dinner, and it was off therecord dinner. And and I
remember someone at that dinnerwho worked at a successful
company was like said to me,Michelle, you can't say that.
Like, you are literally asuccessful startup. You can't go
around saying that.
And I was like, well, that's howI feel. And so I and and so I'm
telling that story a little bitright now because I think

(54:30):
entrepreneurship has thisamazing halo around it where
it's so amazing to be it'salmost, like, shiny to like,
sexy to be a founder, and it'slike you get treated so well and
you hear all these amazingstories, and and it is amazing.
It is the greatestresponsibility and privilege
I've ever had of doing and Ilove my job today. But, like, in
the moment, three and a halfyears in, I did not think that.

(54:52):
Like, I just didn't feel likethat all the time at all.
And and, you know, it's not okayto say that mostly because who
do you say it to? If you're ifyou have a spouse or a
girlfriend, boyfriend, theydon't wanna hear about that.
They just wanna hang out withyou. You're already working a
gazillion hours. They don'twanna hear you complaining about
work when you come home.
You can't say to your team. Youcan't say to your board. I mean,
that's I mean, their job is tomake sure that there's a that

(55:12):
there's not a going concern. Sobeing like, oh god. What am I
doing?
Like, that's that's like redbells to your board. And so who
are you talking to now about it?Right? It's just hard. You can't
say it to investors becausewho's gonna invest in you if
you're like, oh god.
This is just awful. And so soyou kinda end up bottling it up.
And while this is not apsychology thing, it's like, I
don't think that's good either.So you gotta come up with some
coping mechanisms and kinda keepgoing and find the good. Anyhow.

(55:36):
So anyhow, so I sit here todayloving what I do, but there were
so many moments that were hardand not even a moment where I'm
like, I'm like, I'm gonna go tobusiness. There's just moments
where I'm like, it just was hardthree and a half years, four
years long. Like, it was justlike a lot of sacrifice, a lot
of commitment. And while you andyou're in it, it's hard to get
out of it. Like, you just like,at that point, you're not
walking away.

(55:56):
You're in it. You So gotta justkeep going. Now on the other
side of that, thank god that Ididn't walk away. Like, I'm
having the time of my life, andI love it. And I feel like it's
been the greatest thing thatI've ever been able to do.
And I think today, someone wastelling me I went out for with
some girlfriends the othernight, and she was like, oh,
yeah. Type two fun. I was like,what's that? So, well, type one

(56:17):
fun is when you're having fun inthe moment, and type two fun is,
like, in the moment, it's hard,but after the fact, you're glad
you do it. I'm like, startrunning a company successful or
not is a little bit more liketype two fun.
And even the ones that don'twork out, I think and again,
most companies don't work out.Even ones that don't, I think
most people are glad that theydid it because they learned a
lot and met people, and youalmost stretch and expand in
ways that you never thought werepossible. You never quite go

(56:38):
back to the same shape again.And so I think it's a lot of
type two fun in startups. We hada lot of hard moments of losing
your largest customer.
You you're making a key hire,and early on, it's all about
getting key hires, and theyaccept it. And then they don't
show up to work when theyrenege, like, the eleventh hour.
Like, the day before theirstart, you've already told your
board and your employees, andyou're just like, what? And you

(57:00):
thought, like, they were gonnabe this thing you really needed
at the moment, like, the yourlifeline you really needed and
then, like, all a like, my god.Where are we?
Gotta restart. Or we we gotserved a national security
letter when we had 30 people bythe US government and part of it
was to hand over customer datathat we really pushed back
against. And part of thenational security letter is you

(57:21):
can tell people about it. So wewere 30 people. Like, we were
not equipped to deal with that.
Today, sure, we had thenetworks, but, like, most people
thought we weren't gonna existas a company at 30 people. We
were nobody's. Like, it was justlike, what? And we had to go
navigate this really scarything. And, thankfully, the EFF
partnered with us, and thatended up being a positive ruling
on our side.
But, gosh, that took that in themoment, it felt like we were

(57:44):
going out of business. And and,again, and it's these are things
that you have to wear on yourshoulders as a founder. And I
think I am so lucky that I hadcofounders that we were able to
go through those together.Matthew and I have often said I
could not imagine doing this bymyself. I although I know lots
of founders do too.
So hats off to the solo foundersbecause, really, it's amazing.

(58:04):
At the same time, havingcofounders that you don't trust
or don't wanna be with in thosesituations, I think, really do
break up the relationshipbecause they are very stressful.
They really push you to the max.And I think I think maybe the
lesson learned is even though weare a huge success story, we had
those moments. And I don't wannasay find the joy in the heart in
those moments because that'smaybe a little bit too cheesy,

(58:25):
but it's like you do learn alot.
And if not you, someone else hasto make that decision. And some
professional operator you hireisn't gonna make a better
decision than you in thatsituation because you care. And
so just like lean in, do thebest you can, go forward, and
keep going. And if you add up doenough of the right things, it
forgives the things that you getwrong. And so it's a little bit

(58:46):
back to Stuart Butterfield.
You just gotta get a few thingsright to build a successful
company.

Ross Haleliuk (58:50):
Michelle, Cloudflare sees the whole of the
Internet. Given that kind ofvisibility that almost probably
no other company has, from yourvantage point, what are some of
the emerging opportunities orproblems in cybersecurity,
Internet infrastructure, or evenbeyond tech? Like, what is
changing, and how is the futureshaping up that you are excited

(59:14):
about and you would encourageaspiring entrepreneurs to
tackle?

Michelle Zatlyn (59:18):
Well, I I know people and developers are not
done inventing the future. Socustomers' problems don't if you
go talk to a company, they haveso many problems left to be
solved. And if you go talk tothe entrepreneurs, there are so
many things they wanna build.And now with AI, all the new
tools and how to do it, it'slike, again, it's a it's a
little bit of a noisy timebecause it's hard to know what's
here and what's not gonna stayhere, but it's an exciting time.

(59:39):
And so I do think that there's alot of problems left to be
solved.
On the cybersecurity front,unfortunately, there's still
tons of threats. I mean, an AIis only gonna help accelerate
that, and so you need reallygreat modern day defenses that
that almost like fight AI withAI defenses, and Cloudflare is
doing part of that. But it'scybersecurity is a massive
field. There's so many otherparts of that of that of that

(59:59):
ecosystem that an entrepreneurwas looking for a problem to
solve today would be able tocome up with and be like, oh,
I'm gonna go do that. And so soI think that there's, the the
the future is not quite hereyet.
So that creates opportunitiesfor the builders and the
dreamers as I do spend a lot oftime talking to our customers
and you go talk to them andthey're all looking for better
ways to do things with less thatwill that they can scale with

(01:00:23):
and be flexible for the nextdecade. And so I can't wait to
see what we all create as thefuture and and, you know, I
think that that's one of thereasons why I love this industry
is you gotta stay curious. Yougotta you gotta keep learning
because it keeps changing everysingle couple years.

Mahendra Ramsinghani (01:00:36):
Thank you, Michelle, from the bottom of our
hearts. You could have savedlives as a doctor, but instead,
you're now protecting 5,000,000customers globally from the bad
guys. And even as AI starts toreshape the landscape, you are
helping protect the contentcreators from the modern day
crawlers. Your fifteen yearjourney is nothing short of

(01:00:58):
phenomenal, and it's inspiringfounders everywhere. We do hope
that some founder somewhere inthis world is listening to your
story and getting ready to starther own company.
Thank you, Michelle.

Ross Haleliuk (01:01:14):
Thank you for joining us Inside the Network.
If you like this episode, pleaseleave us a review and share it
with others. If you really,really liked

Mahendra Ramsinghani (01:01:24):
it and you have some feedback for us, wrap
it on a bottle of Yamazaki andsend it to me first.

Sid Trivedi (01:01:32):
No. Don't do that. Mahendra gets too many gifts
already. Please reach out byemail or LinkedIn.