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Technology isn't built by companies. It's built by people.
Random Access Memories (RAM) is where technology gets personal. Host Jake Bernardes sits down with founders, CISOs, engineers, operators, investors, and community builders to explore the stories behind the products, the pivots, the failures, and the moments that shaped their careers.
Whether we're talking cybersecurity, AI, startups, leadership, or life outside the office, every conversation asks the same question:
What shaped the person behind the technology?
New episodes every week.
Presented by Hubscale.
Hello. And welcome to another
episode of Random Access Memories.
I've been waiting to have this
conversation since probably December 2023,
when I left Whistic.
This is the CEO and founder of Whistic
and dear friend of mine, Juan Rodriguez.
I'm going to start with the
same questions I do to everyone.
And there is no script, as everyone knows.
Introduce yourself and then your hero
and your hobby or what you do when you're
not at work.
I was originally, you
know, born in Mexico,
but I came to the States
when I was six years old.
Grew up in California.
Culver City, to be specific.
I'm always mad that Culver City
now is like this startup hub.
But while I was, there it was a sleepy
town. I'm like, really you waited.
You waited till I left because.
Because part of what I left reason And
I left as just obviously opportunity.
But before that, I worked at
a few startups in California.
Came here to join Overstock,
which is beyond. com or whatever.
Maybe Bed Bath & Beyond. I
think they changed it yet again.
And then, you know, ran into
the problem of third-party risk.
Started doing it there
while I was architect,
building out the infrastructure.
And then, yeah, started
Whistic 10 years ago.
10 years ago. Okay. Who's your hero?
Can be personal Can be famous Who do you
look up to? Who do you idolize And why.
That's probably my mom,
to be honest with you.
Such a common one. I think
like 80% of my podcast.
Guests are always goes to mother.
Not even father, it's always mother.
Interesting.
I'll tell you why though.
My mother, you know, growing up,
like my first memory ever as a kid.
Is my mother going door to door
selling stuffed animals in Mexico.
And so it's an entrepreneur story.
The first memory I have of America
is my mom going door to door,
giving out business
cards for her business.
And so when it was time to
do Whistic like I didn't.
You know how most people are,
like, afraid of doing that?
Yeah, I just felt like
it was the thing to do.
I never had fear about starting a
business. My mother never worked for
anyone. She always worked for herself.
So did my father until recently.
You know, he now he works
at a hospital. But. Yeah.
So I think that's why over the
years, I started realizing, like,
like a lot of the
experience my mother had,
she talked to me about them and it
just eliminated a lot of the fear.
It's just like. Like she set it up.
And so that's why it's
it's nothing like, well,
obviously there is emotional aspect
to it, but I think a lot of my life,
as I look at it, I'm like, okay, I took
what my mom did and I scaled it up.
I've never thought about just kind of
like immigrant breaks into America is the
kind of archetypal founder story.
But the way you put it's
really interesting, actually.
Like, I've never thought
about it that way, that,
the kind of door-to-door sales is
really the beginnings of high tech.
Like, that's kind of how
it all begins, right?
You go effectively door-to-door with a
mobile with LinkedIn and hope the same
outcome.
Happens.
What's even funnier is I I joke
with my mom, for whatever reason,
my town in Mexico, everyone has like
their own little side hustle. Yeah.
So I remember we went and visited
and I like joke with my mom, like,
what do these people do?
They just trade with each other.
I'm like, everyone has a business.
So it's like, who's buying from
who? Like, they're all just selling.
I'm like, at some point, you're
really just trading money around.
Because I didn't pick that up about,
just for whatever reason, her town,
they all had like a side hustle.
They had their job, but then they're
all selling this, selling that,
selling the other. And I think my mom
kind of just had that same mentality.
That's interesting. What's your
hobby? What do you do for fun?
Oh, for fun, I mean, I could lie to you,
but really all my time
is spent with family.
So lots of soccer practices. The
little one now, he's doing jujitsu.
And so I spend time with that. But I try
to just spend as much time with family.
You know, I used to be a road biking.
You could tell by the belly
that that's no longer the case.
You know, but I used to do that.
I like to draw. I like to paint.
But the truth is, again, I can lie to
you, but I don't get to do that anymore.
It's interesting. I want to
talk to you about leadership.
Because I think you have a
fascinating style of leadership,
and probably one of the most
influential leaders I've had in my life.
Like I've said that to you before.
But I think it probably starts
with like how you're a dad.
Let's talk about that first.
Do you have the three principles
that you think make a good father?
A good father? Yeah.
Like What do you think you
do that helps your kids?
Yeah. I mean, this again really
goes back to my parents. I...
When in doubt, I just say,
well, what would my parents do?
And, and so there are, really core
values that my parents had, that,
that I realized I was like,
okay, I'm going to copy that.
So number one is have a high standard.
I have a very high
standard for my children.
Yeah.
But I follow that up with a ton of love.
And in that way, both my parents are a
hero. My dad was just brutal. Fair man.
Fair man. But on the standards.
Brutal man. And then my mother.
We didn't we I grew up with money,
but I grew up spoiled with love.
So I I believe, like, that combo
absolutely works. Very high standard.
But your children, knowing that they
have that safety net of my father loves
me, or, you know, my mother,
whoever is listening.
But like my children, know that even
when dad is being tough like their father
loves them.
It's interesting. You've got one son who
I know is very good at soccer, right?
I always find it interesting
that you kind of have this weird,
like it's kind of a balance between
pushing and driving, but at the same time,
like go and have fun.
It's almost like they're antithesis of
each other at the same time, but like,
in one way of pushing.
Well, that's interesting. I agree
with differently what I tell my son.
And so this is another one, which
is again, kind of to standards.
But what I tell my son is
you can only control effort.
I tell my employees the
same thing, by the way.
You know, the joke at Whistic is
it always comes back to my family.
The way I want. Whistic
is the way I run my home.
And so I always tell Johnny,
you know, take 15 shots.
You're going to make
three, something like that.
Because in the end,
I've told him, you know,
if the floor is wet and you try to
kick it and you slip on your butt,
You can't control, the floor is wet.
If you make the perfect top corner and
the goalie is amazing and he flies and
he blocks, it, does
that mean you're trash?
All of a sudden you're trash
because he made a perfect save.
All you can control is effort.
It's interesting. I say the
same to my little one, Ollie.
I've managed this football team
now and I always tell them,
like fiercely take risks.
We have a 100% record this
year, which I'm proud of,
but it's because I tell
them like take risks.
If you lose the ball, hopefully
you're there for each other.
You can gamble, you can win it back.
But that moment you take that
player on and get past it,
who knows what you're unlocking Right.
And that's the way to
that's that's life, right?
It's, it's the gamble it's
the risk. It's the effort.
It's know that you left doing
whatever you could. That's right.
Regardless of what the outcome was like,
who cares what the outcome is
if you gave what you've got.
That's all you've got.
Yeah. The other day, my son, they they
played a team a year up, very good team.
And they got trounced. Right. And my
But my son did very well, quite frankly.
Like, just being honest, he did very well.
But, you know, as we left
the field, I told him,
you know what my favorite play was.
He thought, he was like,
oh, my assist. I'm like, no.
I'm like, there was one point where you
lost the ball and you hunted that man
down.
Like, and a year ago, he would
just put his hands up like, oh,
I messed up or whatever.
But just seeing that growth. I was
like, that was it. He's like, really?
Like, I'm serious. That
was my play to watch.
You just not give up and hunt
someone down get that ball back.
I'm like, that's growth.
It's interesting. I'll move
on from soccer in a minute.
But we, we played up a year last year,
so the whole team played up an entire
year. My little boy's not very
tall, he's quite small for his age.
And We played a team who were up a year
who had a winger who he was taller than
me. I had this kid age checked like I
rarely ever asked for an age check but I
said, you're gonna have to show me ID
because that kid looks like, he's 18.
Yeah, my little boy was marking him, and
honestly, he was coming up like, well,
I don't think it was even his shoulder.
But when he came off, this guy
kid scored like three goals.
He'd been picked up by Sheff United
he's in the academy, He said, oh,
I was awful. And I said, you know what?
Like, that's one of the best
performances I've ever seen you do.
And he's like, what do you mean?
Like, the guy ran past me and was like,
I've never seen your level
of aggression. That's right.
That you, I mean, you fouled that kid
and I wanted to applaud because you were
determined and desperate to get inside.
So I think That's the point, right?
It's when you take people to a level where
they're uncomfortable. But they grow.
And that leads me, right?
So this is interesting.
So I have a leadership style these days
that I'm known for that I am incredibly
hands-off, right? I will literally, I set
probably a half year, quarter at most,
sit down with the team and say,
what do you want to accomplish?
And they'll say, this is what we
want to do. I say, that's great.
How do you get there? And I'll say,
this is how we're going to get there.
And I might interject the odd points,
and I don't know if that makes sense.
Or that's not a priority. But other
than that, I'll say, okay, cool.
Like, tell me what you need. And that's
become my style. I learned that here.
Right. And I think that's, that's
a fascinating leadership style,
which is really uncommon in today's world,
is this idea that you
have a two-time approach.
You give people complete freedom
by coming hands off and saying,
do what you think is right,
but at the same time,
you like people being uncomfortable.
Yeah, Why? Tell me,
talk to you about that.
Your leadership style is not normal
for a CEO. I'll tell you that now.
Yeah. I mean, so firstly, I don't
like literally just, if you look back,
I didn't literally like say, like,
kind of do whatever you want.
That's Maybe a bit fun.
So we should clarify that.
It was, my style is more
about like the intersection.
I always talk about that when I,
someone first comes in, it's like,
what do you want to do?
And here's what the business
needs. And that's the sweet spot.
So I try to find that intersection.
It doesn't always work out,
obviously, but usually it does, right?
Because people come in for a title, so
they kind of already know, you know,
they're going to come in and do marketing.
They're not going to, I'm not going
to say, find the intersection.
They're going to say, well,
you know, I want a vibe code.
Like, not going to happen. At least not
at a medium-sized company or whatever.
And so I should clarify that. You
can't literally do whatever you want.
Having said that I think that's where
the genius lives, back to children.
It's why I think children should be bored
in a lot of ways in in that uncomfort
That's where you find, like, the
good stuff, if quite frankly, like,
sometimes I worry about
that, like with AI,
AI is giving you everything
that's already been done, right?
It doesn't have any creative thoughts
or any new thoughts. Not yet.
This is really interesting.
I want to get information So
I, I texted my wife yesterday.
I said, I'm, I feel like
life is a lot right now.
Like, I have multiple projects going
on, both Anecdotes other places.
I felt like super stressed.
And I was like, I feel
like life is too much,
And I went out yesterday and I ran down
the Jordan River trail at like 30k I
took my headphones out,
and then I realized,
because it's Utah and this
place is a bloody nightmare,
I got super dehydrated and there is and
all the water fountains are turned off
until April, apparently.
Oh, I. Didn't know that.
So? So I couldn't get anything to drink.
So I was like, I took my headphones out.
So I was trying to be in the moment.
Yeah I was super dehydrated.
I was starting to feel like awful, And
I had this moment or several moments of
like pure clarity, like when I saw, like
I was grateful for where I am in life.
Like the challenges are all within my
control, like everything's kind of there.
And it reminded me of the moments that,
like my kids who I force on car
journeys to not have any screens,
or who are like forcing them to
where they say they're bored,
I'm like that's good.
Like, tell me about that.
And And I think, it's an instant point
where you say that people in their work
lives, you need to not be bored, but,
you need to be put into a space where you
get clarity and creativity
because there isn't a clear,
here's your task list for today,
here's your class list for this week,
Here's the task list for this month.
Right? I mean, it depends
on the leader. Yeah.
Sometimes there is, often there
is. And so if you have that list...
That's what you focus on.
Obviously you need a list, but I think
it's better if that person comes up with
the list.
It's like, do you remember when we used
to do gold And I would tell you like,
hey, come with a list or at
least some idea, because if not,
I'm gonna give you a terrible one.
Yeah. And I didn't mean that
literally. It was more of a threat.
But what I did mean is
if I come up with it.
What makes you think it's better than you?
Coming up with it like that doesn't
make sense to me, quite frankly.
Just like on a a purist level. Like, why?
Why would I know more what you need to do?
Like, it's there's a humility
about it, quite frankly.
Is it hard, though, like in today's
world, it's a now culture, right?
I want TV, I go to Netflix. Most people
complain about the problem on Netflix.
Is It takes them 30 minutes to
find what they want to watch,
or like you want food now.
Everything is available immediately.
You don't even want to prep, your meals
go and buy pre-prepped meals like the
world has now become self-serving to the
point that immediately you can get it
with like an instantaneous click, Like
so is it hard now to get people into a
space where they have that
moment, of clarity or creativity,
where they have those instances where
they can see beyond the bubble, like,
is that is that hard to give people.
No, I would argue no. As you know,
like I'm a pretty humble guy.
But one thing I'm not humble about, I
hire. Well, I think you have to hire well.
And so you you have to find
the find the right people.
I think if you hire the wrong
person with that that style. Yeah.
I bet it's hard, like,
to be honest with you.
And so you have to find a person
that's willing to do that.
What do you look form Like
if you're interviewing,
how do you find the person who's willing
to go outside of the comfort zone and
be uncomfortable.
Quite frankly, I, I ask interesting
questions sometimes. Example.
Like really more it is about
digging about their life.
You know, they like to ski like,
hey, have you ever been lost?
Just I ask it just kind of curious
way, like not an interview way.
And then I start finding out, like, how
do they problem solve So it really is
like on an individual basis.
Because if you just ask,
like, tell me a challenge.
Like, they already planned for that.
You know, I did the same to you
at the start of the podcast.
As you're here in your hobby.
And you told me two things which
started the whole interview process.
There you go. But that's how I do it,
too. Because, again, it's about them.
If you ask them, like,
what's the most challenging?
They already planned for that.
Like, anyone can sound like
super, I don't know, organized,
whatever look they're going for.
But when you really, really have
a real conversation and, and,
and you can see it in
their eyes, if you, again,
I could kind of tell when people
are lying or not, you know, the,
there's like that delay in the
answer and things like that.
You can kind of see it play out.
And so I do, that's what I do.
I ask them challenging questions about
something they should know about.
Make them uncomfortable.
Yeah. Make them uncomfortable. One scene.
More importantly, I'll be
honest with you, on interviews,
it's not even necessarily
about what question I ask them.
I like when they push back on me.
That's what I loved about you.
Yeah, that you are. You and
I have crazy conversations.
I do it today. I still, if I...
You probably piss people off though. A
hundred percent. Not everyone is for it.
A hundred percent.
I've had candidates who have actually
withdrawn from the process and interview
process. I've intentionally, like,
not argued with them outright,
but like challenged them
hard and go, I don't agree.
They're not for you.
They're not for you. They're not for me.
Like if you're not willing to
challenge me, like what do I...
Another thing I used to tell
you, like what do I need you for?
If I cannot get any fresh ideas,
what is the point. Of that?
It's interesting because if my team
watch this which they often do.
Then you will they will
understand where this came from.
Because I I whenever we do like
our 360 nonsense stuff, right.
They're always like, oh, here's the good
thing that Jake does good I'm always I
don't really care what I do good,
Like I can tell you what I do good.
I need to know what you think.
I don't do good. Like I need
to know what I do wrong.
Like I want to be challenged. I want like.
And I always I'm really,
really articulate.
Though I say when I, whenever I come
with an idea, I need you to tell me why.
It's a stupid idea. 100. And, I
sometimes I'll go, you're wrong.
But I want to know what
you think is wrong with it.
I don't want to know that you think it's
a great idea and you'll follow me to
the grave. That's not what I need.
And one thing I've learned is
everyone says they want feedback.
Not until it comes, everyone
wants positive feedback. Yeah.
That's one thing I've learned.
Yeah. But, so this is actually. So.
I mean, we're going all over the place.
And I'll have to edit this later, but,
Yeah. Welcome to our Conversation.
Yeah. Me and my me and my wife were
a spa recently went away and we did.
Something Which she learned on Instagram
pod right about this relationship
order So you you say.
And it's the, it's weird you're going
to hear this is something that you
remember. So it's it's start
stop. Keep doing, right.
And we talked about peaks and valleys,
remember. Peaks and valleys. Yeah.
And so I found it fascinating
because, her thing for me,
which was keep doing it's apparently
I'm she said I'm very good at feedback.
She's like if you if I tell you
anything you'll like, change.
She's like, there's lots of things
that you do that piss me off.
I was that's fair. But you take
things and you change quickly.
And I I looked at what actually, That's
probably my one like reasonably good
skill in life.
Like I'm not sure I am, but I can
take criticism and I can spin on it.
Like I can just do what
people ask me to do,
because I will keep changing until
I get to where they need me to be.
And I think that's cool, right? Next
question, or maybe difficult question.
Most uncomfortable you've ever been in
your professional life? Hardest moment.
My professional life?
Yeah, I'm going to ask personally in a
minute so you can keep that in the back
of your mind.
If you want. Yeah, let's
see. Professional life.
Hardest moment.
Hardest moment. That's probably
layoffs, Doing layoffs.
Layoffs, still great. Why?
Because I've actually done a lot of
these, personality tests at this point.
You do them over the years. And one
thing that keeps popping up is fairness.
Apparently, that's my top thing.
And so I have a major problem with
letting go of people that did the job.
I have no problem. And I don't say
it with joy, but I just generally.
You don't care?
I'm more of an engineering type
person, right? I still love people.
I cry the night before I fire
anyone or obviously lay anyone off.
But the layoffs hurt because they
did, a lot of times, they did the job,
especially, you know, maybe
not even the first one.
You're like, you know, people, how
they talk, oh, we're trimming the fat.
Like, number one, I never say
that, but I hear people say that.
And number one, that's never true. Yeah.
But then once you get closer to
the bone, then it's really brutal.
So I would definitely
say that's the hardest.
Hold that though. We'll come back to
that. Hardest memory of personal life?
Personal life? I've had a lot, man. I
come from poverty, so I've had a lot.
Pick one.
I mean, when my, brother passed away
from COVID, that rocked my world.
Why? I mean, loss is normal in
life, right? Why that specific one?
Because my sister was hurt. Like my stuff.
I'm really good at handling
stress and whatnot.
Just again, life has
trained me for that, right?
It's not even like a
it's not a Juan thing.
It's just like life
getting beat up by life.
But seeing my sister hurt like that, see
not knowing what's going to happen and
me having to kind of step
in for like about a month,
walk away from Whistic for a bit.
I mean, I try to work,
but it's not the same.
Resonates back to your
layoff comment though right?
One of your, not difficulties,
But it's, You're very empathetic.
You struggle with other people.
Maybe I'll tell you what, What was
the hardest part about it, though.
Personally, it was the first time ever,
ever, ever, ever. I didn't want to work.
It scared me. I just didn't care.
That has never, you know,
people are like, oh, you,
you're eventually going to have burnout.
I've been told that. I
mean, I'm 45 years old.
And told that forever now at this point.
And I was like, I don't
know what that feels like.
I think that was finally what it was.
I had never felt that in my life.
I didn't care. Didn't want to
log in. I almost called it.
I talked to Nick, the CEO at the
time. Talked to him about it.
I was almost done.
What changed? What changed?
I can't get into it, but
I'll just say the details.
But I'll just say, it turns out my
brother-in-law, like the man that he was,
he took care of things in the end.
And so I had a lot less
worry for my sister.
And so that changed because
essentially I was like,
I think I'm going to have to just
move to LA, you know, take care of my,
my nephews and do all that.
And then kind of things stabilized.
Interesting.
And I got back in the game and I
did learn one important lesson.
That is one of the, the, the
moments where I finally said, like,
I'm not going to stress
over things I don't control.
So that was the walk away with that
Massive, massive, massive When was that?
That was, you know, COVID Yeah Yeah, and
so since then Anything stressed me out
I'm like, can I do anything about it?
Like, quite frankly Like the Iran war
I don't think about it much because we
can't control that.
A. Lot of people are stressed
out about that right now.
And I'm like, of course it's
terrible. I'm not saying it's not.
But I don't, I like try
not to watch the news.
I, you know, I kind of go
like, that's, that's another,
if I was in the military, maybe I, right.
Cause I could control that a little
more. I'd be in it, but I can't.
It's insane when you deal with Israel,
like I do, because the most common,
common comment I get is not like
there are missiles hitting buildings.
Again. It's like the Wi-Fi in the safe
room is bad. Like just to let you know.
I'm like the resilience and
attitude of that nation like,
never ceases to to stagger me.
Like they're just like it's like, give
me a sec I'll Get in the safe room and
I'll plug in and we'll be okay.
Again I'm like, wow. Like, that's,
that's a different way of living.
When you've got two kids who are used
to like seeing fireworks in the sky and
they're not fireworks.
But, let me go back to
the layoffs thing. Yeah.
You went through a point where Whistic
was flying right? Upward trajectory.
SafeBase, now part of Drata, came along
with others and started to make the
landscape a lot more competitive,
a lot more difficult.
And you went through the
period when I was here as well,
when we had to go
through multiple layoffs,
The business went through
multiple difficult times.
How hard is that when you are, it's
your business, right? It's your baby.
You've built it, you've got there and
you see that you think you've done things
right, but it then starts to
like, crumble. How hard is that.
It's hard because. Because
it's on you, right?
Even if you didn't make all the decisions,
obviously you you didn't
do all of it, but.
And and it should be on
you like it was on me.
Like it should land on you like too many
people want an out. It's like, no, no.
And so that's the hardest
part, is that, you know,
It's your fault that the children are
going to see their parents stress.
That's on you. It's an interesting
you should own that. Like straight up.
I think what's interesting, you talked
about leadership styles and previous CEO
Nick, and you are very, very different.
Like as much as you talk about, I want
people to be uncomfortable I want people
to have space.
I want people to be bored, He's
very much driven by KPIs, numbers.
He's a traditional kind of coo
kind of like metric driven leader.
Sure, How hard is it when the
two of you have to Completely.
Do I mean they say opposite attract,
right. Is that a good thing?
Is it really hard when different
styles you're trying to run business in
different directions like
you talk about hiring.
You will be hiring,
entirely different people.
The person that you want as an archetype.
And he'll want as an archetype
is completely different.
I mean, I believe in KPIs and all that.
I just think, again, I think, I think
the Zone of Genius doesn't live in those
KPIs, but you need them,
so let's clarify that too.
I mean, you saw it. We had two
different businesses in one business.
The product side Ran, behaved very
differently Than the business side,
Because that's kind of how we split it up.
I mean, knowing what I know now, I would
have just been CEO from the beginning.
I wasn't ready for it.
For the record, I'm not claiming I was,
But I'm saying like knowing
Literally knowing what I know now,
If I could take this person and go
back I would just be CEO So, but again,
I needed the learnings.
I needed to get back to life, beating
me up so I can progress. I needed that.
Two businesses out of one business
was the reason it went wrong,
Do you think or not?
Do you think it would
have happened anyway?
If you'd been CEO from the start, do
You think you'd have faced the same
problems or not?
That's a great question.
I mean, you'll face the same
challenges of the market, obviously.
So it's not like me being CEO
is going to change, you know,
competitors and whatnot, timing.
But no, obviously it would be different.
Difficult conversation.
So I know from being very
tight in the VC community,
obviously Nick was released by
the board here and moved on.
Right?
How hard is it to be part of that when
you've built a business with someone,
for so long and the board
effectively says, look,
we don't think they should
be part of this anymore,
and you sort of have a choice.
You sort of don't. But
like, that's got to be hard.
No, absolutely, it's hard You know, I
had a loyalty to Nick Because kind of to
that point, Were there times earlier
where I was like, I should just do this?
There were. But I am grateful for Nick
For the things I learned from him.
You know, the trajectory he put us on.
And so, yeah, very difficult Even if he
and I The interesting thing about Nick
and myself is, And I've said it to people,
Nick has said it to
people like Nick and I.
We were never like like super buddy buddy.
It's not like we went
to dinner after work.
Like we were strictly business, but
we we worked well in that regard.
Like I understood Nick.
Nick Understood me.
It's got I learned a lot from
Nick too in a very different way.
And I think it's interesting because
I think it must be one of the hardest
things. It's almost like for a
founder or for a CEO, if you've,
it's like you've grown your kids up and
then you're you told you can't parent
your kids anymore.
Like, it must be like that moment
for him, which must be so hard,
How you move on from that?
As I kind of suppose as a couple
or as a business is is difficult.
I've thought about that. Like, for him.
Like, I mean, like for me, like,
the board could have said, you know,
Juan needs to go.
So I, I've definitely. Thought.
Because you say like
you owned the failure,
right. Good statement up on camera.
But I mean, for the record,
From, from a job description, Nick owned
the failure in as much as he was the
one. That. Was,
I mean I offered. I've offered.
My resignation before because
when we had the layoffs.
Like, I think you have to own it. Yeah.
So I owned it. Owned it, you know.
Nick at the time didn't accept it. But,
you know, I, I, I think you need to.
What lesson did you learn from him?
You said you learned what was the
most important lesson you learned.
Quite frankly, be more aggressive.
Early on, I think, I think in the
end, Nick started playing it safe,
But early on, the confidence that he
showed in just like, go hard, go, go,
go fast. I think, I think in, in
like the, the, when we were smaller,
that was his comfort zone because
he had been past that point.
And so he was able to aggressively
move in that direction.
So that's like number
one being around him.
I was like, man, I
played it safe too much.
Yeah. He had crazy self-belief.
No question. Like unbelievable
self-assurance.
And as you know, me, I'm, I'm
self-deprecating. Like I'm a realist,
pragmatic.
And quite frankly, I learned, like
You. Don't always have to be like that.
And it doesn't violate your
core values To call your shot.
Like that does not, I
used to think it did.
I used to be like, oh, that is out of
character for me to behave that way.
But now I've learned like, no, sometimes
you can just see it, Whatever it is,
and you just go attack it.
I agree.
I think also sometimes you can see stuff
and you don't always have to get it.
Right. Like I've had moments in my
career recently where I've gone,
I think we can do it.
We didn't end up getting there. Right.
I'm going to roll a dice and see what
happens. I'll give it a damn good shot.
I'll give everything I've got on
the field. We'll see where we get.
If we get it, we're amazing. We went
past where we thought we could go.
If we didn't get it, look, we tried
and failed, right? It's better in life.
To have tried and failed or loved and
lost than never to have loved at all.
Yeah. I mean, it's, it's, it's
kind of like, you know, people,
a lot of times they'll say like, oh,
entrepreneurs are different because they,
they like to take risks.
No, I think the truth is entrepreneurs
calculate risk differently.
And so I think that's kind
of what you're bumping into.
Explain that more to
me. That's interesting.
Yeah.
And so so some most people when they
calculate risk they only literally see the
risk okay.
They they focus too much on the risk.
They don't see enough of the reward.
It's as simple as that.
And so for an entrepreneur
who's been through stuff again,
me in particular see my mother and
seeing the shots she took me having taken
shots in life, quite
frankly, betting on myself,
that calculation starts weighing in in
more of the like the gain side of things
versus the risk side of things.
It's interesting. It's making me think.
So I obviously left Whistic to go to
a company called Gutsy where I was for
like seven weeks. Didn't
work out at all, Right.
I think that's interesting that the
lessons I learned from that two months is
a lot more than I probably
learned in the last five years.
Oh, yeah. Because it's that that it taught
me. It's the risk reward calculation.
Like, I've been asked multiple times
would I go back and do it again?
I'm like, yeah, probably. I'm like,
because the reward seemed logical to me.
The risk seemed tolerable.
It went wrong, but like I learned a
hell of a lot from it going wrong.
And I think that's, the attitude you're
talking about is the fact that-. And.
Only when it goes wrong,
you go, oh, that was wrong.
But what if it went really right?
Yeah. And I think that's the mentality
of like real leadership, right? Yeah.
That's interesting. Let's
come back to leadership. Yeah.
Leading from the middle.
There's two lessons I think I
learned from you, which I still have.
One is leading from the middle,
that you don't lead from the front,
you lead from inside the group.
And the second, which I think I am a
tremendous advocate of, is if we succeed,
it was someone else.
If we fail, it was me. And you've
said it multiple times today.
We failed, it was my
fault, right? Yeah, 100%.
You think that's
important to every leader?
Because not only a lot of people don't.
Like I know a lot of CEOs who own
their success, and when they fail,
they suck execs.
No, I think I think it's a style
thing, to be honest with you.
Some people, I mean, like look at look
at everyone's darling Steve Jobs. Yeah.
That guy owns success.
Right? People when it was wrong.
That guy has never, never
written a line of code never,
did a lot of the marketing
stuff, but he owned it.
Having said that, obviously he was a big
part of the vision, so he deserved it.
He deserved it as well.
Don't get me wrong.
But what I mean is that's
what people liked about him.
They wanted to be around that, that aura.
So no, it doesn't have to be my way.
My way again is is this life I've lived
where life is constantly trying to drag
me back down. And I'm like, nah, dude,
I'm going to break through, right?
And so, no, I don't think
everyone needs to have that style.
It's the fighter mentality.
It's interesting.
It's just a difference.
Yeah, it's just the style.
It's common in immigrants or second
generation immigrants who have this kind
of mentality around them.
You just said something about vibe code.
There was a conversation we had
before we started recording,
which I think is interesting,
around hiring engineers today.
And you said something interesting.
You said that I don't
want vibe coders, right?
You can you can build toys, but
you can't build products. Correct.
Which I've said, a few times recently,
that I think you have to hire
orchestrators who can leverage tools
to build better code and products.
But you can't just hire people who
just know how to play with Cursor,
or play with Claude Code.
Correct Do you think that's
an industry plague right now,
that everyone's just rehashing existing
like repos and building off of, like,
components and just building
the same thing over again.
Well that's Interesting question.
Yeah, I think, yeah, I
hadn't thought about that.
But if you think about it, it's kind
of like that comment I said earlier,
where AI is only going to generate what
it already knows or what it has access
to. So, so there's
probably something to it.
Have you said that if you hire the, if
you have the right engineers and they're
creative, they'll, they'll know how
to massage it to do something new and
creative.
So no, I can't say like, as a matter
of fact, like that is what's happening.
But it could start happening.
Or creativity starts to
go away and we start. To.
Lose. That's what I. Mean, it could
genius. It could totally go there.
I don't think it will, though.
Again, I think that's the human experience
is we always push the envelope for
good and for bad, quite frankly.
Do you think last couple of questions.
But one thing I have a concern
about is I look in my chair and go,
if if SOC is now AI'd and GRC is
now AI'd and pentesting is now AI'd,
how does anyone like, with my background,
end up becoming a leader who has the core
foundation to understand what they do
for a job?
Because we're taking all of tier one,
including software engineering and
automating it.
So how do you get like senior engineers
and architects who understand the whole
process if they never did layers one
and two because they don't need to.
I've been asked kind
of a similar question,
the way I've answered in the past,
which I think applies to this,
usually I answer the question about
like, people jobs being eliminated.
But I think it applies to this too, is
that if you think about it like 30 years
ago, like most of the jobs that exist
today did not exist back then Right?
A lot of the marketing like
I'm talking pure titles.
Yeah obviously marketing has
always kind of been a thing. Yeah.
But like those very specific
titles did not exist.
And so I think that's what's happening
again. You You might be right.
Maybe it's not. Engineer is is junior.
Senior like it might not be a
thing, but I can't even predict.
But the titles will just be different.
Interesting. Two questions to
finish. One logical, one random.
I always ask this in some kind of form,
but I'm going to go specific on yours.
You found Whistic 10 years ago right.
You You can go back to 10 year ago one.
What's the one thing you've learned
since that you would give yourself as
advice then?
At the time, around the time we
started it, I still talk to him today.
We have an investor,
his name is Al Landon.
And when I, looked to
hire a CEO, he warned me.
He said, hey, I need you to know that
it doesn't matter if you're a founder.
The company will take on
the personality of the CEO.
So if you want the company to
run the way you want it to run,
you need to take that job.
And I, again, nothing about against anyone
else is just knowing what I know now.
Like I already said it, I would run it.
You'd go back and start and do it
Again. I would. Just do it. Interesting.
Last question.
My daughter Izzy is eight now, and every
podcast I end with a question that she
asked. They can be incredibly random.
This is the one that is
in the linear order now,
If you could go on holiday or
vacation anywhere in the world,
where would you go and why?
Oh. You know, you chose the wrong person.
For that.
I know, that's why it's a good one that's
come to you because you don't really
do vacation.
So if you could, if you were
forced, where would you go and why?
Before that, let me tell
you something funny.
So the leadership team, they've been
pushing me like you need to be more pro
vacation There's going to be
burnout, you know, on and on.
Two weeks ago, I took my wife
for breakfast during work hours.
You claimed it was a vacation?
I've been claimed. I'm like, hey, I
took a one hour vacation the other day.
And now this is like week three. And
they're like, I think it's run its course.
Do you remember when I put Honda on a
plan that gave his bonus attached to
taking vacation?
Yeah. All right. Back to where are
you going? You got to go somewhere.
I'm going to Japan, man.
Why Japan?
Because I love their culture.
I love how they're just they're they're
They do a lot of things differently,
right?
Architecture down, down to the artwork.
Like, it's just different in a good way.
When Would you go? Spring, summer,
autumn? Winter what's the time of. Year.
Doesn't matter. I actually like the cold.
So regardless, I'd like going
to the mountains or something.
I wouldn't go, I'd go to like, Kyoto.
You know, I'm not like
a Tokyo kind of guy.
You're gonna do it this year. No. Why.
Because that's not who I am.
You got You've just committed
to the place you want to go.
Yeah. No, I committed to that, like,
20 years ago. Well, you should go. No.
One day. Okay? Otherwise, you don't have
something to live toward. Right? Okay.
Anything left? You want to tell
anyone that listens Any tips?
Founding technology? Anything.
I want people to know generally
like I I want people to, like,
really think about how
they treat other people.
Because one thing I I've learned.
So I'll tell you this. When. When?
Before I became CEO, one of our, someone
from our district, her name is Loti,
asked me to read Radical Candor.
She had asked me actually to
read it a few times before. Yeah.
And I always thought that book was
about people being jerks and having an
excuse to be a jerk.
Okay. That's what I thought
about Radical Candor. Okay.
So she finally commenced me to
read it. Yeah. I'm at a tournament.
I'm sitting there. I literally remember
the moment because it was jarring to me.
I'm sitting on the bench, my kids are
playing, and I start reading the book,
and I get into chapter two, and I'm like,
oh, that's why they want me to be CEO.
And what hit me is really about how you
can't really hold people accountable if
you do not care about them, if they
don't feel like you care about them.
Otherwise, it's just criticism. And
people don't want to just be criticized.
They want to improve. But they don't,
no one just wants to be criticized.
You and I are weird in that way.
Like, we literally are like,
no, be critical so I can grow.
Most people are not like that. Most
people need to be cared for and loved.
And then you can kind of give
them some criticism to improve.
And quite frankly, I
just do that naturally.
So when I read that book,
I was like, oh, I get it.
I get why they want me to lead this thing.
It's interesting. I want to finish
this. There's a quote on my son's wall.
It comes from a book That
I think I'd have to check,
I think it's called The Boy,
The Fox, The Mole, and The Horse
Oh. I have that book For my Kids.
Yeah. And there's a phrase. There
This is my wife's favorite phrase.
We have it in several places
in the house, It says,
In a world where you can
be anything, Be kind.
Yeah, I agree with that.
And I think that Is that.
If you lean with kindness, Like
it'll go a long way Yeah Because you,
can You can just go Go
further with someone that way.
100%. Thank you for your time.
All right, I appreciate it.
It's been an absolute pleasure.