The Business Leadership Podcast

You are listening to the Business
Leadership Podcast with Edwin.

Paul: I am Paul Newton, creative producer
of the Future Narrator miniseries,

and I'm joined by Edwin Fzo, host
of the Business Leadership Podcast.

We are recording live at Web Summit
Vancouver 2025, where we're exploring

how today's leaders shape the future, not
just through strategy, but through story.

We believe that a strong point of
view is what inspires communities.

Builds movements and cuts through
the noise in uncertain times.

So let's dive into this conversation.

Today's guest didn't set out
to be an ENT entrepreneur.

He just couldn't stop
building things that worked.

Avery Penham is co-founder and CEO
of tail scale, a company reimagining.

Secure networking through a zero
trust developer friendly approach

known for turning impossible
ideas into elegant systems.

Avery has spent his career translating
bold visions into working code and

often into full fledged companies.

Whether he's building low level drivers,
architecting network protocols, or making

secure infrastructure radically simple.

Avery brings a rare mix of technical
brilliance and product strategy.

And while he'll tell you, he just
likes to code, the trail of innovation

he leaves behind says he's very much
a builder and very much a founder.

Edwin: Welcome to the
Business Leadership Podcast.

Xavier, how, how you doing?

Avery: I'm doing great.

And I just wanna say, I don't know who
wrote that intro, but that was amazing.

Edwin: Oh, no, thank you so much.

That that was, that was our friend Paul
here with, with the, with with our aid of

your information on the web and our chat.

GPT uh, assistance.

Ah.

Paul: Oh, wait, wait, wait, wait.

And we like.

Toastmasters, if you don't introduce
people properly, you don't set

the stage for, for who they are
or what they bring to the table,

Avery: so Right.

But now we've set unrealistically
high standards for the

rest of the conversation.

Edwin: No, I mean it's good.

It's good.

And we are gonna be fine.

Ry we we're so as mentioned, we're here.

I.

On at Web Summit Vancouver, on
the tail end of, uh, your speak,

how's, how's been your day and
how's your experience here so far?

Avery: I mean, it is been
a very exciting conference.

I did a, I, I got a talk on the main
stage yesterday and on the AI stage today.

Wow.

Uh, which I thought was kind of funny.

Tail scale, not being an AI company.

Uh, but everybody wants to hear about ai.

Mm-hmm.

So I'm like, all right,
you wanna hear about ai?

I can talk to you about AI if you like.

Uh, and we did.

Edwin: That, that's amazing.

Any, any key takeaways from
your time here already so far?

Um, a memorable one, um, a

Avery: conversation you may have had.

Uh, well this is the first time
Web Summit's been in Vancouver.

Uh, and it's also the first
time I've been at Web Summit.

So that's, it's, it's fun.

Uh, I think there's, there's
lots of cool people here.

One of the things that's a
little shocking, there's a.

Speaker lounge, uh, which
I know you guys have seen.

Mm-hmm.

Uh, many people don't get to see it.

It's big and it's full of
people because they have so many

speakers at this conference.

This is a gigantic conference.

It's like probably one of the
biggest I've ever been to.

Yeah.

There's so much stuff going on.

There's so many things on the show floor.

There's so many people here.

Everybody's like excited about things.

High energy.

Edwin: Yeah.

And we're just really facilitating
those human, human connections.

Right.

Um.

Curious.

Um, and if you could just share, Avery,
if you could, you know, about tail, tail

scale and really the problem that you're
solving when it comes to secure networking

and that zero trust infrastructure.

Avery: Sure.

So tail scale, fundamentally what
it does is just lets you connect

one device to another device
or any other number of devices.

Mm-hmm.

So it, it is very much like what
the internet is supposed to do.

Uh, for those of us who are old
enough, we can remember back in

the 1990s and the vision of the
internet was, what does it do?

It lets you connect a computer to
another computer anywhere in the world.

Right?

And it's weird how, now that
is such a hard problem, right?

If you try to connect your phone to your
laptop without a wire, how do you do it?

Paul: Mm-hmm.

Avery: Right?

There's actually, there's no good answer.

I wanna send a photo from
my phone to my laptop.

Maybe I can use Airdrop if they're
both Apple products and airdrop

works like 50% of the time if
they're right next to each other.

Right.

But 0% of the time, if they're
not right next to each other.

Yeah.

Right.

And if they're not both Apple
products, you got nothing.

Right.

It's like I can't send a photo
from one computer to another.

Like why?

Well, because T-C-P-I-P, the
internet protocol has been frozen

in time for like 30 or 40 years now.

It hasn't changed.

And now like you can't find the address.

You can't get a name of the device.

Everything's behind a firewall.

If you go somewhere else, it's
behind two different firewalls.

There's just no way to
connect them to each other.

And it's devolved into this world
where if you want to send data from

one place to another, you go up to the
cloud and back and both directions.

You get charged rent by a
big cloud provider, right?

So what used to be like the FTP protocol
back in the nineties, you file transfer

from one thing to another and it's
basically free except for the bites.

Amazon gets to charge you to send stuff
from two, between two things that are

sitting side by side on your desk, right?

And tail scale makes that part go away.

We, we make a connection direct between
those two things, no matter where they're

in the world, um, without forwarding
through anybody else's infrastructure and

getting at maximum speed and encrypted.

And attach to your identity, right?

And that's useful for sending
photos to between your devices,

but it's also useful for companies
who have the same problems, right?

They have computers scattered at
different places in the world.

They have employees, especially
co post COVID, who are like often

working from home, don't come into the
office, need to access all this stuff.

And those things need to
be able to find each other.

And if you're forwarding it
through a central relay, it

makes it slow and it's expensive.

And tail scale just eliminates that
complexity and eliminates the slowness.

I mean,

Edwin: Avery, that's uh, two things.

First thing that came to mind as you.

Describe the problem.

We have this video camera here
that does all our podcasts.

I was there last night.

I was telling Paul I gotta transfer this.

What do you think?

How should I do this?

Because eventually we want to give
yourself the raw audio and your team the

raw video, and we have a notion board.

I'm like, okay, do I airdrop this or do
I connect this thing or do I do this?

And then I could, should I put it
to Google or do I put it back to

to this and then get it to notion?

I think I, I think I broke my brain
yesterday just thinking about how

many different ways I could go.

Yep.

And they weren't easy.

Avery: And think about how many
decades we have spent as, as an

industry not solving that problem.

Oh my gosh.

It's amazing.

That's the thing that everybody
wants to do, is move data

from one computer to another.

I'm like, oh yeah, that's hard.

And all really, it should just be as like.

Edwin: Right there.

Of course.

Just

Avery: split it right there.

Alright.

Right there.

Of course.

And it was like the very first or second,
I forget which order they came in.

Protocol on the, in original
internet standard in like

1970, there was Telnet and FTP.

Yeah.

Right.

You could FTP things in like 1970 between
any two computers on the internet.

Yeah.

And now you can't.

Like, how weird is that?

Edwin: Yeah.

And why, why, why did they get, why
did they get rid of that anyways?

Um, I mean it's, it's, it's such
a, it's such a, it's such a problem

that most people don't even realize.

I, I would say that they have, right?

I mean, they, they know the challenge.

They get it done and they forget about it.

Yeah.

I think exactly.

Avery: We, we get a lot of people who
try tail scale, uh, especially like nerdy

technical people who like, think they know
everything and have a lot of experience

and they try tail scale and they're like.

False.

So when you don't, I'm actually
angry now, and I'm not angry at you.

I'm angry right now.

I'm angry about the fact that I've spent
my entire life not realizing the pain I

was in, and it just suddenly disappeared.

Yeah.

Right.

And it's like, what?

Who did this to me?

Right.

And they just have, they're in this,
they have this shock moment where

it's like the internet just worked the
way it obviously should have worked.

And obviously it should have
worked like this, and I forgot

that it should work like this.

It just, I, I assume that this mess is
the normal situation and it just always

has to be that way and it doesn't.

Yeah, no, a, I mean,

Edwin: that, that's great and
I, I'm really glad that you are

working on it, but I'm curious.

As you described it, and part of it
is being a tech person or a developer,

you, you, you sometimes you get really
down to the layer one, layer two layer.

Some of my listeners may not even,
you probably lost them at that point,

but when we described going, you know,
putting files, I, I'm curious, you

know, what is your personal unique point
of view and what do you bring to this

problem, um, that will help solve it?

Avery: So I've been doing
networking for a long time.

Yeah.

Um.

I, I started, let's see, when was it?

It was when I was in high school.

Uh, we had a dial up internet at home and
my sister wanted to use the computer, uh,

and use the dial up internet and talk to
our friends on internet relay chat, IRC.

Mm-hmm.

Uh, for those of us who remember it.

And I wanted to use the
internet at the same time.

And this was a problem 'cause there was
only one phone line and only one modem.

Um, so I downloaded
this thing called Linux.

I figured out how to connect
two computers to each other.

I figured out how to share the
connection on the modem between these

two computers so that she could do
her IRC while I did my other stuff.

Right?

And like I was, you know, maybe
14, 15 years old at the time.

Uh, and this knowledge sort of like.

Propelled itself into, I got a job
at the, uh, the city's first internet

provider, uh, like commercial one because
they were having trouble running their

systems and somebody like, Hey, this Avery
guy I think might be able to help you.

And I was like 15 at the time.

I got my driver's license.

Shortly after getting my job at
this company, my dad had to drop

me off at work to fix the internet.

Oh my God.

For my hometown of Thunder Bay.

Um, and it's, it's kind of like, you
know, it's been around and around

and around and around since then.

I worked at Google Fiber.

Uh, where we're bringing gigabit internet,
uh, to the people of Kansas City, uh,

Missouri, and then Kansas City, Kansas.

Mm-hmm.

Uh, in that order.

I actually didn't know before I got
to Google that there were two cities.

Edwin: I just learned that right now.

Avery: Exactly.

And I'm, you know, I'm embarrassed
to say this because it turns out

like most people know this, and the
big one is Kansas City, Missouri.

Incidentally.

Kansas City, Kansas is smaller.

Um, anyway, so we brought
it gigabit internet.

Our, our team built wifi routers and you
know, the joke we used to have on my team

is that the reason you're not getting your
gigabit internet is us, uh, because you

can get gigabit fiber into your house,
but nobody connects to the gigabit fiber.

Right.

They're all on wifi.

And wifi simply did not go at a gigabit.

Mm-hmm.

Uh, it kind of sort, if you're really.

Careful about your configuration.

You can maybe get that today,
but nobody realistically does.

But you could theoretically,
but at the time, absolutely not.

Right?

So everybody bought a gigabit and
then went straight to speed test.net

and found out they weren't getting a
gigabit and called their support line.

And that was, you know,
it was our job to, uh.

Be at fault for that.

But we built these wifi routers
and we tried to get as close

to a gig be as we could.

Uh, and it was really fun
building that project.

'cause we shipped like hundreds of
thousands of eventually millions of

devices out to individual customers and
we could monitor all the, the network

and optimize it and stuff like that.

So I've been doing
networking for a long time.

I'm quite old.

Uh, I'm one of the people
who's left who remembers.

The vision of the internet from the 1980s
and nineties, a lot of people starting

it now just inherited the thing that
works, the way it works, and there's like

flaws pretty down, low down in the stack.

And instead of fixing those flaws,
we've been piling pieces on top.

And now you've got this mountain
of workarounds that everybody

just assumes has to be there.

And like, you know, very few people are
brave enough to do the archeology and like

dig their way down in the stack, down to
like the actual source of the problem.

You.

Paul: Oh, I love that.

Avery: Like

Paul: I, that you, you're just like, oh
yeah, I'm old enough to remember that.

And I love that it
started with your sister.

Right.

And you know, those fights that
well, I mean over that one phone

line, first of all, like you're on
the phone and it's busy or whatever.

And that's what we had to deal with.

And then a call waiting came and it's
like, answer it or what have you.

But like the fact that you're
like, okay, I'm gonna connect

two computers to this and it's.

And it's just going back to
these really simple things

that we forgot could be simple.

So yeah, I guess that that introduction
wasn't so bad, like making something

elegantly simple because I mean,
how did it get so complicated?

Avery: Yeah, how?

How, I mean, I think a lot of
people are afraid to touch the

part they don't understand, right?

And like, especially in computing,
we're like, okay, we just

assume this mound of complexity.

Is there and it's really hard to,
like, there's all kinds of social

reasons and like technological reasons.

It's hard to change somebody
else's mound of complexity.

It's pretty easy to add.

Another thing on top of the mound
of complexity, one of my friends

has this saying, uh, that's taken
from some computer scientist is

like, you can solve any problem by
adding another layer of indirection.

Accept the problem with too many
layers of indirection, right?

And it's absolutely true.

Like as long as you don't care how
many layers the system has, you can

usually work around your problem
by adding one more layer, and then

somebody else will show up and add one
more layer and one more layer, and one

more layer and one more layer, right?

Like if you develop a web app
nowadays, you could write HTML.

Nobody wants to just write HTML.

They need like 17 frameworks.

They need no JS downloading 700 packages
that all have dependencies and other

dependencies, and it like builds like
megabytes or tens of megabytes of garbage

that then it uploads to your browser.

To display an H TM L page, right?

Why is that there?

Because each of those layers was designed
by somebody and nobody knows how it

works anymore and they don't wanna know.

So like, can I just like grunge this
pile of complexity over into this corner?

And like, I guess I'm like, maybe I
enjoy pain, but I'm like, you know what?

I don't.

I like, I prefer to write my webpage with
HTML and I prefer to do my networking

at this like low level with packets and
stuff and like I want the packets to work.

Right.

And there's people out there that
like when, when I make it work

or when me and our team wings
at work, they appreciate that.

They're like, oh, thank goodness.

Now there's a new ball that
I don't have to look inside.

But it's so much smaller than the old
ball that I didn't want to look inside.

Paul: So you just don't
deal with workarounds, you.

You just start fresh.

And I

Avery: mean, we all spend most of
our life dealing with workarounds.

Right?

Um, but you know, my biggest
successes have been just like slicing

through and tail scale is a company
where we're like, you know what?

We could actually just do this.

Let's make a company that slices
through all these workarounds

and we'll sell the new ball.

Right.

And you know, a part of it is like.

For individual users, we
give it away for free.

And the way it's designed, it doesn't
really cost us anything because

we don't route your traffic, which
means we don't pay for any bites.

Right?

You're the one like generating the
traffic on your own existing internet

connection that you're already paying
for, which means we can give away lots

and lots and lots of tail scale and
it doesn't really cost us anything.

And then the people who wanna
pay us are companies who want.

Centralized control and, you know, all
the like auditing and administration

and logs and stuff like that, that
we can give them as sort of on top.

Oh, wow.

Paul: And so, uh, web
Summit came to Vancouver.

You've never been to Web Summit
and see, you're like, well, it's,

it's time to, to speak here.

And, uh, you got right up on
center stage what, uh, um.

What's your objective?

Uh,

Avery: I mean, do I have an objective?

I guess our PR team would
say, my, our objective is to

get more famous more quickly.

Excuse me.

Uh, because we want more people to know
about tail scale, and most people who

find out about tail scale can go to an app
store and download it and use it for free.

Right.

Uh, there's the, the free plan is
up to three users, up to a hundred

devices, which is more than almost
anybody needs for almost anything.

For their personal use.

And that's not going away.

There's no time limit.

Uh, there's no throughput limits.

Uh, you can use it for whatever you want.

There's not no non-commercial
use limits, none of that stuff.

Um, but I.

Turns out a lot of people
who do that are techies.

Techies often have jobs, uh, and
they will bring tail scale to work

to solve, you know, after they've
solved some problems at home,

they're like, Hey, pattern matching.

I have a problem like that at work.

Yeah.

And it's really stupid how
we're solving it at work.

Why don't we use tail scale instead?

And next thing you know, it's at
work, it's spreading around and then

they're buying it for the company.

And so the more people who know about
tail scale, the better off we are.

All of our customers come through.

That path.

We don't do outbound sales
or anything like that.

We do just like awareness and people
tell their friends in some case, like

bludgeon their friends repeatedly
saying like, no, stop complaining.

Just download tails scale.

It'll literally take you five minutes.

Just do it.

I'm so tired of hearing you complain.

Right?

And they finally do it and
they're like, oh, now I see why

you told me that so many times.

I should have just spent the five minutes.

Paul: So then you're the guy that
sees how to make something really

complicated that has evolved over time.

Simple.

By

Avery: that.

That was, that was my big innovation.

That's what that was.

Start what started tail scale.

Now I'm the guy who does a
bunch of bureaucratic stuff to

run a company of 160 people.

Okay.

Just a leader.

Yeah.

And then people like tell
me to go to Web Summit.

And they're like, Avery, I
wrote you like a talk proposal.

Does this sound good?

And I'm like, yes.

And then they put me on the main
stage and I'm like, oh, I guess,

I guess I better live up to this.

Hmm.

And here we are.

Yeah.

And here we are.

Oh, well.

Paul: Well thank you for your,
for sharing the backstory.

It's been great.

Edwin: Yeah, a ry There's a
lot of everywhere I wanna go.

Uh, you paint a lot of pictures.

I may look younger than most people
know, but I remembered the dial up.

My, one of my business
partners, he set up his own BBS.

Oh yeah.

He had motherboards on the
basement floor on eight lines,

you know, to a, to a house.

Um, so, so it's really interesting
that this, this, this problem.

You're solving and I think what
might be very interesting in terms

of, you know, you, you really got
into this very specific use case I.

But the layering challenge, I
think is getting worse now with ai.

Um, like no one knows.

So I'm a computer engineer.

I went, I, I remember when OO was new.

I did machine learning.

Like I did the machine, I did a
assembler, I did zeros and ones.

I know how that works, but
no one knows how that works.

And the layer is so big now and
it's just getting even worse.

So I think the mission and
what's refreshing is that.

You're cutting through that.

And I think there's an awareness
to that too for people.

Future generations is like,
how did we come to this?

Avery: Yeah.

I mean, the thing that gives
me the biggest aneurysms with

AI is AI code generation.

It's like, let's just think about this.

We made the ball of complexity so
big, they're like nobody can to

understand how to use it anymore.

So you know what we should do?

We should use an even bigger ball
of complexity over here to write.

To learn how the first ball of
complexity works, and then write

even more crap to pile on top.

That more or less does what you want.

Edwin: Yeah.

Avery: And then people are like,
oh, now I need to debug it.

Edwin: That's right.

Avery: Well, I don't understand the code.

I didn't write it.

Now it's like a ball of complexity
with a ball of complexity on top.

You know, the easiest thing to do with
a ball of complexity, with the ball of

complexity on top to fix your problem is
add another ball of complexity on top.

But I don't know how to do that.

I'm gonna ask this first ball of
complexity to write another ball

of complexity and stack it on top.

Yeah.

She's like, guys, this.

It's horrible.

Yeah.

It, it, it offends my sensibility.

Yeah.

No, uh, it's also probably going to work.

Yeah, right.

Because what, what is evolution?

What are humans?

It's just like.

A pile of hacks piled
on top of more hacks.

Yeah, right.

And evolution produced it, you
know, over billions of years

using genetic algorithms.

But like if you actually look at how
the human body works, there's all kinds

of terrible stuff going on in there.

Oh yeah.

Right.

Like, you know, one thing that was
like came from when we were fish or

whatever, and it's like still there.

Why is it still there?

It never evolved out again.

Right.

So like it's interesting, like we're
just regenerating the same kinds of stuff

over again, and we know that can work,
but it's also kind of the antithesis of.

Engineering, which is the
course I took in school.

And engineering has this sort of
element of like elegance, the concept

of like, you know, you could do this.

Better.

Right.

You could design this to like
specifications you can learn less with,

you can learn to make things good.

Yeah.

Right.

And you can learn to control
like what probability mm-hmm.

Of failure there'll be.

Right.

And it's never zero because
you can't build anything that's

like perfect and infallible.

But you can, you can understand the
level of the probability of failure.

You can make something that's
predictable and reliable.

Mm-hmm.

If you follow the in
like steps to do that.

Right.

And we kind of.

Going public is means to, it's so tempting
to just give up on that and like pile

crud on top of crud and or like make a
machine to pile crud on top of crud and

then we have no idea what's going on.

But at least it's not your fault.

Edwin: Yeah.

Avery: Right.

It's like, look, yes, you can do that.

And I know everyone's gonna do that.

Yeah.

Right.

But it doesn't mean we have
to stop doing the other thing.

Edwin: That's right.

Avery: Right.

We can keep making good things and
you know, the good thing we made

also gonna be something the, the ball
of complexity can write code for.

Right.

So if we can eliminate some
of this pile of garbage.

Yeah, people are still gonna use
the AI code generators, but at

least the AI code generators can,
will have an easier time of it.

Yeah.

Um, I got, I got a question

Edwin: before we end.

I'm curious if you could share, and I'm
gonna put some context for you, given,

given to your journey and what you
shared, I'd love to get final thoughts

or advice or actionable recommendations
specifically to the business leader or

the entrepreneur who has to get away from.

Doing the work, doing the code,
and really become the leader.

Like what kind of advice could
you share with those people?

Those founders who are here at Web
Summit, they might be here already and

they don't know how to do that yet.

Yeah, well,

Avery: yeah.

There's a lot of people who've
had to go through that process.

I've had to go through that process.

Yes.

I don't get to write away code nowadays.

Yeah.

Kind of makes me sad.

Um, so it's, it's hard to let go of that.

Mm.

Um, often, I mean, the first time
you do it, you will probably screw

it up 'cause you'll delegate.

To people that were not ready to be
delegated to, or were not the people

that you wanted to delegate to, or they
do it differently from you in like a

bad way, as opposed to like, everyone's
gonna do it differently from you.

But if you get great people and
you put them in the right team and

you give 'em the right information,
they'll do it differently from you.

Like maybe in a good way, maybe even
better than you would've done it.

That's right.

Right.

And so at tail scale, they took, you
know, I have had a pretty long career.

This is not my first startup.

Um, people are doing tail scale
better than I would've done it, better

than, than me and my co-founders
did it back in 2019 when we started.

Right.

And that's kind of exciting, right?

But you have to like, it takes a lot
of work and a lot of, you know, gaining

experience, but you can actually build
a team of individuals who, each of which

can do something better than you can.

And together the whole
team does everything.

Better than you can, and that's when you
get something that's working really well.

Edwin: Well, that's, that's, that's
amazing advice that, that's a mic drop.

Avery, thank, thank you for sharing that.

Before we let you go, we wanna present
you a book called Future Narrative.

Paul and I co-authored this together.

Mm-hmm.

It's for the business leaders who
are, who are out there now telling

the stories, getting on stage in
Web Summit and, and learning how to

inspire because those who are telling
the good stories can not only get more

investment people that work for them.

Ultimately build a community
and get more clients.

Uh, so we want to present that to you.

And thank you for joining us on
the Business Leadership Podcast.

All right.

Well, thank you very much
and thanks for having me.

You are listening to the Business
Leadership Podcast with Edwin.