Founder's Mentality: The CEO Sessions

When did showing up become optional? 
  
In 2009 Michelle Zatlyn co-founded Cloudflare, a tech startup that powers 45% of all Fortune 500 companies through solving problems that were keeping their leaders up at night. The surprising thing is, Michelle had no background in engineering. She developed an expertise through showing up, leveraged her own strengths to build a billion dollar business, and wrote a playbook all founders can learn from in the process. 
  
Join host Jimmy Allen of Bain & Company and Michelle as they discuss the importance of solving problems that people care about, how to build teams that thrive off cross-functional collaboration, and how to balance delivery and development agendas throughout moments of hyperscale. 
  
Michelle’s story highlights the importance of showing up. Not all leaders start off as experts, but they can become one through being in the room where it happens. How can founders push themselves to show up, even at times where they don't initially have the expertise? 
  
This is a conversation about balancing delivery with growth, building a team that will drive progress through collaboration, and becoming an expert through showing up in the process. 
 
>>> LISTENER SURVEY: Share your thoughts at https://www.podpolls.com/founder 
 
https://www.bain.com/founders-mentality/  
  
EPISODE CHAPTERS 
00:00 Introduction 
00:48 No founder has the perfect skillset 
02:31 Finding the right problem to solve 
04:19 Building a customer-led tech company  
06:42 How Michelle became an expert 
08:15 The importance of showing up 
12:37 Navigating moments of hyperscale 
15:18 Scale demands decentralization 
16:20 Empowering cross-functional collaboration 
17:13 Protect the steady state, disrupt the status quo 
18:30 Balancing delivery and development 
19:35 How Cloudflare delivers and develops 
21:43 Scale changes a founder's role 
22:40 Recruiting for spiky capabilities 
24:39 The Cloudflare way 
26:10 Michelle's playbook 
  
LINKS 
A Beginner's Mindset: The Art of Showing Up - Jimmy Allen - Blog [https://tinyurl.com/TheArtOfShowingUp] 
Bain & Company LinkedIn [https://www.linkedin.com/company/bain-and-company/] 
Bain & Company X [https://x.com/BainandCompany] 
Jimmy Allen LinkedIn [https://www.linkedin.com/in/james-allen-3442b/] 
Michelle Zatlyn LinkedIn [https://www.linkedin.com/in/michellezatlyn/]
 
About the Host: 
Jimmy Allen is an Advisory Partner at Bain & Company with over 35 years’ experience advising leading organizations. He’s the author of multiple best-selling books on growth and leadership and the host and founder of Bain’s Global CEO Community Forum. Jimmy is a regular speaker at global business events, including the World Economic Forum, and serves on the Botswana Economic Advisory Council. Outside of consulting, Jimmy started his own record label [Abubilla Music] in 2008 and supports Singing Wells, a project dedicated to preserving Kenyan village music.


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What is Founder's Mentality: The CEO Sessions?

Before a strategy becomes a success story, it's a judgement call.

Now in its second season, Founder's Mentality: The CEO Sessions gets inside the decisions that defined some of the world's greatest leaders - a bet the market couldn't yet see, a crisis that put the organisation's purpose to the test, and the courage to keep showing up even when you don't have the answer.

How do you stay close to the frontline as the organisation scales?
What does AI mean for the thing you have spent years building?
How do you transform the company without breaking what makes it great?

Hosted by Jimmy Allen, Advisory Partner at Bain & Company, bestselling author and leader of Bain's Global CEO Forum, each episode is a candid, in-depth conversation with leaders from Mars, The Economist Group, Khan Academy, and more.

Each episode is built around one real story, one defining moment, and the lessons that come from living through it. Dense with insight and designed for leaders who listen with a pen in hand, the series explores the outer game of markets, technology and growth, and the inner game of energy, humility and courage, and what it takes to master both.

The question this season isn't just what the CEO should do.
It's who does the CEO need to become?

Join the Conversation:
https://www.bain.com/founders-mentality/
https://www.bain.com/insights/topics/ceo-agenda

Links:
Bain & Company LinkedIn (https://www.linkedin.com/company/bain-and-company/)
Bain & Company X (https://x.com/BainandCompany)
Jimmy Allen LinkedIn (https://www.linkedin.com/in/james-allen-3442b/)

About the Host:
Jimmy Allen is an Advisory Partner at Bain & Company with over 35 years’ experience advising leading organizations. He’s the author of multiple best-selling books on growth and leadership and the host and founder of Bain’s Global CEO Community Forum. Jimmy is a regular speaker at global business events, including the World Economic Forum, and serves on the Botswana Economic Advisory Council. Outside of consulting, Jimmy started his own record label (Abubilla Music) in 2008 and supports Singing Wells, a project dedicated to preserving Kenyan village music.

Bain & Company:
Founder’s Mentality: The CEO Sessions is brought to you by Bain & Company, a global consultancy trusted by the world’s most influential business leaders. With decades of experience guiding organizations through growth, transformation, and leadership development, Bain’s executive insights offer what it takes to lead at scale.

- I remember people saying many times

in our San Francisco office,
"Wow, it's so refreshing

that you and Matthew
still show up for work."

- When did showing up become optional?

(upbeat music)

I'm Jimmy Allen,

and this is "Founder's
Mentality: The CEO Sessions."

Michelle Zatlyn co-founded
Cloudflare in 2009

with her business school classmates,

Matthew Prince and Lee Holloway.

Today, Cloudflare
operates in 125 countries

and protects 20% of the
world's internet traffic.

Of the three founders,

Michelle was the one without
an engineering background,

which is what I thought this conversation

was gonna be about.

(gentle music)

I would love to start with
just the very simple decision

to be a co-founder of Cloudflare

and what that was like
as a non-tech person

to be part of the starting
of a tech company.

- I had two great
co-founders, Matthew and Lee,

and we were really excited
about what we were working on.

And while I wasn't an expert

and it wasn't like a clear slam dunk,

sometimes people start companies

in something that they worked in before

or knew a ton about, and that's great.

Like, those are assets.

Actually, a lot of people who
start companies also do it

as an outsider, and that's
actually also a great asset

because as long as you have
a high rate of learning,

you get to question everything.

Almost kind of like from
a beginner's mindset

of saying, hey, I'm not already an expert.

I don't have a point of view on this.

Let me go and run this down.

Of course, I was like,

"Do I even have the skillset to do this?"

And all these different things.

But I think as I look back,
thank God I didn't listen

to any of those notes, because
the reality is like, no,

of course I didn't have
all the perfect skillset.

But you know what? No founder does.

And it's putting yourself
in the situation,

having to make decisions,

having to learn from those decisions,

and how fast you can learn

and then make another good decision

actually is what makes you
a great leader or founder.

It's not what you go to the table with.

- You started with an insight

that very few single founders start,

which is no founder has
all the skills necessary

to start and build a company.

It's always a founding team.

And most discover that

only after a couple crashes and burns.

It feels like that's the one
insight you guys did have,

that we have complementary skills

and will somehow figure it out.

- I think starting a company is hard

and actually like the stats
are most companies fail,

and it's hard to actually solve
a problem that's meaningful.

It sounds so easy and trite,

but actually it's hard to solve.

Go find a problem that
a customer needs solving

that actually you need
to do more than once

to build a business around it.

And so early on, before
Cloudflare was born,

Matthew and Lee had another initiative

called Project Honey Pot.

This was a community that cared
a lot about cybersecurity,

and so we were surveying them

to understand more about the problem set

when I got some survey results back,

market research back from this group.

And it was kind of like,
tell me your pain point

around cyber threats online.

And again, this was back in 2009.

It was a very different
world than it is today.

Some of the qualitative answers
were the best part, Jimmy.

It was things like cyber threats

are the scourge of the internet.

They're criminals and
they steal resources.

It was a very visceral response

from this potential customer,
kind of our ideal customer.

There was other ones like
cyber criminals make me believe

in the death penalty.

These were not casual answers.

They were written in a way
that when you read them,

they kind of jumped off the page.

And so it was clear there
was a real problem here.

And when we were starting,

like any eager founder
would, I was reading a ton.

I read just like anything,

you're gonna start something in an area,

you're not an expert,
you're trying to read a ton.

And I was reading books about founding,

and it was interesting.

I remember this one book
I was reading at night,

and I remember the sentence,
"95% of startups fail."

And I took the book and
I threw it off my bed

and I was like, "Why am I doing this?"

So I was like, "Okay, we
can't be one of those 95%.

I don't wanna throw
away this opportunity."

And so then we became so obsessed of,

are we actually solving a
problem that people care about,

that our customer cares about?

- What was that like as a non-tech person

starting a tech company?

The phrase keeps coming up to me,

which is kind of customer-led tech,

which is that it's just not
true you're a tech company,

you're a customer company that serves tech

and that you feel like you
have a good feel for customer.

Is that fair? Is that a focus?

- It was interesting that early on,

it wasn't data that actually
was important to us.

It was actually some of
the qualitative feedback

we got from our early customers

that we were doing Skype calls

with every time someone signed up,

and after the fact of saying,
"Because of Cloudflare,

this is the first time in five years

I've slept through the night."

And honestly, it was like
those were the things

is what we recruited
on, we raised money on

because they were so emotional.

And I think that if you
can solve a real problem,

a pain point for a company or a customer,

there's no bigger responsibility,

and it just feels incredibly empowering.

You're like, "We built something

that actually solves a problem

and delivers real value to somebody."

Then you're onto something.

And that seems so obvious,

but some people start companies

that actually don't solve real problems

or they solve something

that 10 other companies already solve.

And you're like, "Okay, but
do we need an 11th solution

in the market?"

And maybe we do, maybe it's
better, but are you sure?

And how do you know?

And you have to hold
yourself to a high test.

Even to this day, I love
spending time with our customers.

Our whole executive team

loves spending time with our customers

because when you talk to the customers,

all of a sudden it's very clear

what the priorities should be.

And in every single growth company,

there is more to do than
time and people to do it.

And so getting the order
of priorities right

is really important.

And one way to do that is
by talking to customers.

- And the issue of listening to customers,

I mean, is that been something

that you've been able to provide

is kind of get into the tech conversations

and say, look, I can at
least put the priorities down

as our customers see them.

- Well, it's interesting.

I'm just listening to your reflection.

I started a company in an area
that I was not an expert in.

I was technical in a
different sort of way,

but I wasn't technical in this space.

And so there was a lot of learning.

I was drinking from a fire hose
when we started Cloudflare.

And the reality is, today I am an expert.

And it's because I've
showed up every single day,

and I've learned a ton.

- Guys, I need to make a mea culpa here.

I walked into this conversation

with a pretty strong premise,
non-technical founder,

room full of engineers.

How the hell did she survive?

Well, Michelle shut that
down in about 30 seconds,

and she's right.

I mean, Cloudflare is 16 years old.

She's been doing this
every day for 16 years.

Of course she's an expert.

The more interesting question
is how she became one.

(gentle music fades)

- When we started Cloudflare,
there was eight of us.

We worked in an office in
Palo Alto on Emerson Avenue.

We used to go to lunch
every single day together

and we had basically all
engineers and me at this company.

And everybody was technical,

checking in code except for me.

And we were talking about technical things

all day over lunch.

We were building, again,
back to sorts of things.

And I'd go back home, back to the office

and I'd make a list of everything I heard

and I'd go and I'd look it all up.

And so kind of by the end of the week,

now I was talking a lot
about reverse proxies and DNS

and all these sorts of things.

And if you have the
courage to put yourself

in that situation where you feel like,

I don't know everything.

And that's hard, but that's how you learn.

Now we have an amazing
customer support team,

but the first two years of Cloudflare,

Matthew and I were pretty much tied

for the most number of
support tickets answered.

And you learn a lot because
those were technical questions.

And I loved that and I loved learning more

and I loved hearing people

even more ahead of me
in the technical ability

so that the next time
I could do it myself.

I'm competitive. I wanna win.

I wanna be able to do everything myself.

I don't wanna have to call
an expert on something.

I wanna be like explain it myself.

And thank goodness I did that.

- Most CEOs I talk to
today when they finally

kind of confess will say they feel

like they're being held
hostage by the tech,

made much worse by AI, that
they don't understand it.

There's big budgets for it.

People are coming in telling
them they have to do X and Y.

They don't have the
instincts to prioritize.

You said, well, one thing that a CEO has

is a beginner's mindset,

like break it down into
language that you understand.

The second thing is you said that,

yeah, but customers set
the tech priorities.

- If you are a C-level executive

and you feel like, I don't
understand all this tech or AI,

but I don't know where to
start, the best thing you can do

is just put yourself in the situation

and then go and try and connect
the dots after the fact.

And then by the fifth time,

you're gonna know a lot
more than the first time.

No one will remember the first four times

that you didn't know
the right thing to say

or you weren't sure.

But gosh, by the fifth time
you start to feel better,

then you start to contribute more

and then you start to
get the feedback loop.

And all of a sudden you're
like, I do know more.

The worst thing you can
do is not put yourself

in that situation

'cause you don't want
to look unknowledgeable

because then what happens is
you really are unknowledgeable.

And all of a sudden you don't
know the questions to ask,

you don't have the right instincts,

you haven't had the four mishaps

to get to the good one,
the rate of learning.

(gentle music)

When we got to like a 350 people,

we started to attract talent

from what I would say
like Silicon Valley talent

who had worked at other
founder-led businesses.

So we were really excited.

And I remember a couple
people saying many times

in our San Francisco office,

"Wow, it's so refreshing
that you and Matthew

still show up for work."

And I didn't really
understand what they meant.

And finally I was like,
"What are you talking about?"

And they're like, "Well, my last founder

stopped showing up for work."

I think it's because founders at the scale

and you start to get real revenue

and you have to learn about
finances and governance.

You don't know what to do,

so you just stop showing
up to those conversations

because you don't wanna look like

the unknowledgeable person in the room,

but then you aren't
a good business leader

'cause you're not in the room.

You might know the tech,

but you're not a good business leader.

And so I think like one of the best things

that Matthew and I have done
over the course of Cloudflare

is we keep showing up for work.

And even when we're not
experts, we show up,

we surround ourselves, we ask
the questions and we learn

so that you have better instincts.

You gotta stay in the field,
you gotta stay in the game.

Otherwise, it's just so easy to drift.

And I think that's true
for both executives

with technology and AI, and
it's also true for founders

or employees of high growth companies

who wanna get to the next stage.

(upbeat music)

- You know, I spend my life talking about

how companies go from
insurgents to incumbents

to struggling bureaucracies.

And we ask ourselves, why
do leaders let this happen?

For older companies, the
answer is often this,

because the current
leaders were never around

when the company was an insurgent.

They joined a big complex firm,

and they've learned to lead an incumbent

mired in complexity.

But why do founders let it
happen to their companies?

They know what it's like
to lead a small startup.

Why did they let bad things happen?

Michelle hints at an answer.

Maybe they just stopped showing up,

stop leaning in, stop learning.

We know this.

As the company scales,
the conversations change,

finance, governance, new
functions, different meetings,

and many founders just
choose not to be in the room

where it happens 'cause
they don't like those rooms.

They don't feel they can add value

to all these new ways of working.

They opt out,

and suddenly they're not
running the company anymore.

They're just watching it.
This applies to all of us.

Increasingly, leaders are being asked

to lead through things they
don't fully understand.

AI is the latest example.

And when that happens,
the temptation is to defer

to the experts to not
show up in every room

where it happens, whatever it is.

But we wait outside,
we try to learn enough

to participate again in key
decisions and key meetings,

but Michelle's warning you,

you don't become an expert
by staying out, you show up.

And Michelle showed up

over and over again until
she was indeed an expert.

So stay in the game, stay in the field.

(upbeat music)

Michelle, let's switch to
the hyperscaling moments.

And what I mean is you've
used from 8 to 350,

from 350 to 3000.

How did you keep the culture?

How did you keep your focus
on what needed to happen

as you became bigger and bigger

and complexity creeps in,
energy vampires creep in?

How did you guys either
adjust to the new scale

or try to keep that founding
culture of eight people,

two of which are leading
in customer support calls?

- For a while, we had a
really, I would say, simple

but very helpful obsession
over what are we doing?

Who is doing it? Did it get done?

If I'd met you and we had 800 people,

I could have put up a spreadsheet saying,

here are our top 100 priorities

across the company this quarter.

Here who owns it and week by
week is a green, yellow, red,

or is it blue?

Blue was done.

And that really set the
foundation of Cloudflare

as a company of doers and builders.

And actually just by
putting the list together,

that was super clarifying.

And it was one list for the whole company.

R&D was on there, marketing
was on, everyone was on there.

And so it was like, these are
the most important things,

that list as we grew, 'cause you can start

to do more things when you scale,

that list became 250 things.

And we did that for a long time.

And it was just like, who's the person?

What is it? Who's the person?

Who's the supporting
team, and did it get done?

And that was really very powerful,

the first 10 years of Cloudflare.

Because when someone new came in,

you could show them, here
are the things that matter,

here's where you're plugging in.

And so it just became this
cultural norm of Cloudflare,

our builders, doers, we ship
things and getting stuff done.

And your description of the
third phase of a business,

of what did you say,
what kind of democracy?

It was not a very...
- Struggling bureaucracy, yes.

- Struggling bureaucracy,
which my heart rate

and my blood pressure goes
up every time you say that

'cause it's like, that's
exactly what I don't wanna be

'cause I have so many things left to do.

It's like, how do you fight against that?

Well, the way one of the ways
that we fought against it,

and Matthew and I were
very aligned on this is,

we keep innovating, we
keep getting stuff done.

And it's not, by the way,

like Michelle doesn't own
everything on this list

of the priorities.

We want different people
across the organization

to feel empowered.

And we wanna push down
the decision making.

And we wanna go as fast
as humanly possible.

And so fast-forward
today, one of the things

that we're really known for
at Cloudflare is innovation.

So we innovate a lot.

We ship so many new products and features

every single month, week,
month, quarter, year.

When I talk to our customers,

which again, back to how do
you know your priorities?

Well, you go to customers

to help make sure that what
we're doing resonates with them,

and it's like they love our innovation.

That's why they choose
to do business with us.

- And how do you keep it alive?

I know how you could keep it
alive when there's one list,

you're running it, you're
standing up with 100.

Now let's say there's a 1000 or 2000,

you've gotta work through others.

What do you do to keep it alive?

- Yeah, it's not natural,
I'll tell you that,

because I think as leaders,

some of the things you
want to do is centralize,

go up the totem pole,

and actually you have to do the opposite.

You have to decentralize.

You have to push the decision making down.

You have to empower directors
to be making decisions.

You have to empower a
lot of the organization.

And so it's interesting as we have scaled,

we've been able to bring in folks

with really quite impressive pedigree,

which we're so excited about,

but sometimes they show up at Cloudflare,

and actually I'm like,
"Wow, you just are talkers.

You actually aren't doers."

And they're like, "I don't
wanna empower my team.

I wanna be in the middle of the decision."

It's like, "Why do you
need to be involved?

Why are you even at this meeting?

The person who owns it
should be at the meeting,

but why do you need to be here?"

One thing that I don't think

is talked about enough right now is,

in modern day work today,

work is done so cross-functionally.

We're still organized often functionally.

So you have a manager
within your function,

but who you often work with
the most is not your manager,

it's people of other teams.

And it's that small group of people,

sometimes you hear like
a pizza party or whatnot,

are responsible for kind

of the end-to-end shipping something.

And often the best time, it's
from a couple different teams.

You know, you might want a designer,

you got a product manager,
you got the engineer,

then you got someone on marketing,

you got a go to market thing,

and maybe someone from finance.

Well, they all report to different people.

They're not all reporting to one.

And that manager doesn't
really exactly know everything

because they're not in the flow.

And so you have to be okay
with empowering your team

and saying, honestly, here's your mission,

here's the priority that matters a lot.

- So then when you've got
all these cross-functional

teams running around,
what happens to that list?

- So at Cloudflare, we can deliver

more than 250 things a quarter,
so we don't have one list.

But what we do is,

there's kind of the steady
state of the business, okay?

There's like the momentum of the business.

We don't really talk
about those things, Jimmy,

because those things are gonna get done.

What is much harder to get done

when you're in a steady flow of a company

is all the things that disrupt status quo.

What net new thing do
we need to invest in?

What's some major change thing,

or something that like all
of a sudden is important

to the company that wasn't
important the last three years?

Those are the things that we
set priorities for the year

because they always take
more money and more energy

and they need to be
talked about, you know,

seven, eight, nine times

'cause there's something
new and different.

But the steady state we don't talk about,

we kind of assume, we kind of
say those have to get done.

That's just like a given.

That's all of our jobs as executives,

but it's these net new things

that we got to start to make progress on.

Otherwise, we're gonna
have a problem next year

or the year after or the year after.

Coming up with that list is hard,

but when you do, is it clarifying?

'Cause all of a sudden, you know,

whoever's working on
that can point saying,

this is one of the company priorities.

This is why this is taking
priority. I need help.

And we can celebrate
that while also keeping

kind of the day-to-day
operations of the business going.

Both of those motions at
once is an art and a science,

and it's something that it's never perfect

the first time you do it, but
if you keep working at it,

it's a muscle you build,

and then it's a language internally,

and then people start to understand it,

and then they get rallied behind it.

So you're both proud if you get to work

on one of the net new things.

And by the way, those are always hard.

Those are like boulders up
a hill. They're never easy.

Anything net new that's
new is hard. It's hard.

It's, you don't know, you
don't have all the resource,

you definitely don't
have the right people,

you don't have enough
money, all the stuff.

Like it's always hard.

Or if you're working on something

on the steady state of the business,

and you're shipping stuff,
and you get to celebrate,

and you're going to make money from it,

like that's exciting to celebrate too.

If you can celebrate both,
you're in a sweet spot.

- We would refer to
exactly your steady state

versus the new hard thing
as the steady state for us

is your delivery agenda
where customers benefit

from flawless execution of known routines.

We know how to ship, we know
how to keep customer promises,

and your development agenda

is the new hard stuff that
we don't know how to do.

We're gonna have to test and learn.

And you're saying we learned

that you have to be great
at both and celebrate both.

My hypothesis is that part
of what you learned to do

as a leader was to hand
off the steady state

and let other people get on with it

because it was a known way to operate

and then you guys stayed focused
on the new and hard things.

- So I was nodding along
until that very last sentence,

which I would say is a little
bit too neat in the box

and probably gives Matthew
and I too much credit

and not enough credit to
the folks at Cloudflare.

The delivery agenda you're
framing, which I like,

like the executives,

we have great executives
who come in and they scale.

Like, we hire them to scale. It's working.

And if you're a founder, you
wanna get to $100 million.

Or if you work at a big company,

you're starting a new unit.

The first milestone

is how do I get to $1
million, $10 million?

And then how do you get to $100 million?

That's really important.

And then the second thing is,

okay, get from $100 million,
how do you go to a billion?

That's when you're scaling.

And there's a lot of delivery agenda.

And so bringing in
executives who are builders,

and there are some many amazing people

who can help you scale, that's magical.

Aileen Lee created that
word, the unicorn, right?

Like you had to get to
a billion in market cap

to be a unicorn because
it was about scaling.

That is like the
workhorse of the business.

And so you need great people to do that.

And by the way, as a founder,
I'm talking to customers,

I'm helping recruit, that's celebrating.

It is that.

And you have to start to
start the hard new things

that are gonna matter

once you get to that billion in revenue,

'cause if not, you run out of
runway on that first thing.

You need to stack successes
on top of each other, right?

And you need new capabilities.

And so maybe it's a geographic capability

or maybe it's a customer
segmentation capability

or maybe it's a net
new product capability.

So these are net new things.

And I think what's important is one

is not more important than the other.

Both are important.

And I think what's been interesting

about this delivery development agenda

that you framed within Cloudflare

is we've kind of had
teams dedicated to both.

And I feel we're not perfect,

but I don't feel like someone feels like,

oh, if you're on one, it's
better than the other.

I think both feel
they're equally important

in the organization.

We're better if we can be
winning on both versus just one.

(gentle music)

- Five years ago,
Michelle could have put up

a single spreadsheet, 100 priorities.

She would have known every one of them.

And that's not unusual.

In the early days,

founders are often the
connective tissue of the company.

They know the customers,
they know the product,

and they know where every
decision comes from,

but scale changes the job.

The challenge is no longer
making every decision.

It's creating the conditions

for thousands of good decisions
to happen without you.

It's not about being the smartest,

most connected person in the room.

It's about creating
smart, connected rooms.

And that, for Michelle,
is the unnatural act,

resisting the temptation to centralize,

pushing the decision making down,

empowering the people in
the room who aren't you.

And that means finding the right people,

not talkers, but doers.

(gentle music)

In many ways, you guys
are a wonderful example

of what we would call spiky capabilities,

meaning you weren't a well-rounded team.

Each of you brought something
of incredible strength

to the team and by
definition had weaknesses.

And what often happens to companies,

and I always call it like
rock grinding equipment

with diamonds, is even
though you're founded

by people with appalling strengths
and appalling weaknesses,

as you scale, you start looking
only for the all-rounders,

the people that are sort of a
little bit good at everything.

Have you maintained this
focus on finding people

with spiky capabilities

and recognizing that as a
team they're gonna be great,

but avoiding the trap of
recruiting kind of all rounders?

- Yes.

And I think quantum cryptography online,

not like cryptocurrencies,
but like TLS and SSL,

that's just an expertise we have in-house.

And so those are very spiky people.

Data, very spiky people who we
just deal with so much data.

Network engineers, very spiky.

Like, key skills, unique
to what we do at Cloudflare

are very, very helpful.

Cybersecurity experts.

We just have lots of examples

of folks who are really,
really good in certain things.

And we have lots of folks
who are good at other things,

and I think the real power
is partnering them together

to build these teams
that to go ship things.

And the data shows the
more diverse the team,

the better business results there are.

And if you can take
sometimes really spiky people

and partner them with other things,

that's when magic happens

and those teams can move mountains.

And I think that's what I love.

If you get a group of people together

where they seem so different,
but they create these things

that are really outsized impacts,

I think that's where the real magic is

and the real value
creation for the business.

- And my hypothesis is
that means you've kept out

a lot of the professional
management systems

that declare war on
all those spiky people.

It feels like throughout the development,

what you've resisted

is kind of classic
professional management.

You've done it your way.

- Well, okay.

So it's interesting

'cause Matthew and I
met at business school.

And so we believe in
management and leadership,

I think it's super important.

We have some really seasoned
executives on our team

that fit that description absolutely.

And we do it the Cloudflare way.

We are a very transparent company
internally and externally,

and so we share a lot around
the why we're making decisions.

I think we're setting a new standard

in the industry actually

around being more transparent
internally and externally.

I think it sets a new bar for other folks

who are kind of working with
customers and it accrues trust.

And so I think that it's kind of helping

develop a new set of leadership.

But again, we have a lot of
professionally trained leaders

on our team who are amazing operators

and we wouldn't be here
where we are without them.

- Bring the leaders in, keep
their systems out, Michelle.

Keep their systems out.
- Yes. Yeah.

At Cloudflare, we ship,
we don't just talk.

And yes, that means you ship too.

And look, if that doesn't work for you,

then this just isn't the
right place and that's okay.

Like let's end on good terms,

but otherwise let's go create
something special together.

One of the things I'm proud of

is like the different
chapters of Cloudflare.

We had leaders stay for a long time

because we worked really well together

and they were really bought into this.

We wouldn't be where
we are without everyone

who has been part of the
Cloudflare's journey along the way.

- There are three things

that stayed with me
from this conversation.

First, the courage to walk into rooms

where you're not yet the expert.

Second, the discipline to keep showing up

until you are the expert.

And third, when the
company gets big enough,

the wisdom to build an organization

that can do all that without you.

That's what 16 years of
these instincts produces.

A company of doers doesn't talk, it ships.

What strikes me talking to Michelle

is something we've been hearing
across this whole season.

From Jacqueline, from Sal, from Danielle.

In a world where AI is
changing everything,

the leaders who step back

and let it happen to their companies,

they're gonna be left behind.

Your people need you in the room,

showing up, be the
voice of your customers,

be the voice of your people,

represent them while others
propose the algorithms.

This isn't about how you
lead as a non-expert in AI.

This is about how you become
the AI expert the world needs.

We need to take a leaf out
of Michelle's book here.

The ones who keep showing up

are the ones who get to
write our next chapters.

We'll be back in two weeks. Stay curious.

Next time on "Founder's
Mentality: The CEO Sessions."

(upbeat music)

- The core lesson

is that adversity is an
extraordinary opportunity

to learn and to perfect yourself.

Then you need to have this perspective

that it's not about
winning, but about playing.