Video summary
The CEO of OpenDoor orchestrated an aggressive turnaround for a company facing imminent bankruptcy by violently restructuring corporate defaults and eliminating inefficiencies that had plagued the organization. He immediately fired external consultants who were perceived as "professional leeches" creating excessive fees, while simultaneously shifting hiring criteria to prioritize hard work over comfortable cultural vibes. To stop the business from atrophying, he mandated a return to in-person collaboration and demanded a culture of truth where employees felt safe disagreeing openly rather than maintaining polite lies or false consensus. Furthermore, he streamlined operations by reducing friction points, such as consolidating home-buying processes so that staff could resolve issues like restoring power without needing managerial approval for every small task.
Strategically, the leader pivoted the company away from unprofitable general contracting services to focus exclusively on being a "market maker" that buys and sells homes quickly while monetizing ancillary revenue drivers like mortgages and insurance. This operational shift was grounded in principles of distinguishing between theoretical models and reality, avoiding acronyms that signal organizational inversion, and prioritizing product utility over complex strategy. He also embraced the transformative power of artificial intelligence to collapse management chains rather than replacing human capability, arguing that technology amplifies efficiency when used correctly. By focusing on these core truths, he ensured the company could survive extreme pressure and adapt rapidly in a volatile market environment.
The speaker draws parallels between his own near-bankruptcy experience and Steve Jobs' transformation after NeXT's financial crisis to illustrate how experiencing extreme pain reveals one can endure far more than imagined. He advises founders that paralysis by fear is dangerous because inaction leads to failure, urging them instead to focus on the first easy fix rather than getting stuck on difficult problems later. This mindset was shaped early in life as an immigrant without social clubs and through playing rugby, where he learned deep joy from winning a team despite physical pain, allowing him to ignore public opinion even when facing criticism from major outlets like the Wall Street Journal. He agrees with Four Seasons founder E.J. Sharp that excellence is defined by the capacity to take pain, asserting that true winners are those who persist longer than others against modern distractions offering easy satisfaction.
Ultimately, this philosophy of enduring hardship centers on a profound sense of accountability and legacy rather than mere financial gain or personal comfort. The CEO defines success as optimizing his life and career to leave a significant dent in the world for future generations, specifically ensuring that his children can be proud despite him sacrificing parts of their own childhood. This commitment is shared with his wife, reflecting a partnership built on mutual responsibility and the willingness to endure necessary struggles for long-term impact. By embracing pain as a catalyst for growth rather than avoiding it at all costs, he demonstrates how resilience against distractions and difficulties creates leaders who can build enduring value while maintaining integrity in their actions and decisions.
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You need to figure out which defaults
are killing the company and change them
violently. There must not be change
management because you want the change
to feel jarring.
>> You took over a company that was months
away from bankruptcy.
Take me inside the company.
What did you do on day one?
>> I left home
um to fly to San Francisco where
OpenDoor had a one office.
Um
and on the way out the door, I told my
wife, "Hey, sweetheart, I'll be back on
Thursday." And she said, "Do not come
back until you have a plan to break the
company either." I'm like, "Haha, very
funny. This is hilarious." And my wife
said, "No, no, I'm not kidding. Do not
come back." She went on Amazon and
ordered a mattress to the office for me.
Like I knew I was going to sleep in the
office for multiple days in a row
because my plan was try to figure out
what had gone wrong. Because basically
what happens is
all companies fail in similar ways.
No companies succeed in a All successes
unique, but all failures rhyme. Good
people leave. People lose control of
innovation. G&A goes up. And over time,
you end up finding picking fights with
your customers and partners. So, that
had happened at OpenDoor. I asked for a
full list of all employees, every
contract, every payment the company had
made for the last 12 months.
And they're like all the accounts. Like
I'm like, "Okay, give me like the
state." And one of the things I realized
is
that it is actually surprising
how
lack of active management allows
companies to atrophy.
>> What do you mean by that?
>> If you're trying to avoid looking bad,
you do a certain number of certain
certain things, right? So, OpenDoor for
a very long time was doing everything it
could in order to not be noticed, in
order to not stand out. Which meant the
company was basically had become a
company run by professional consultants.
Let me give you two specific examples.
So, I got
um we agreed that I was going to join
the company and then uh chair of the
board
sent me a Google Doc that was going to
be my announcement that this guy is
going to become the CEO of the company.
And I like read the doc and it sounded
like it was written by someone trying
very hard
to avoid saying anything that might
offend anyone.
So, I took over and made edits and then
someone went in and undid my edits and
like changed the doc again such that it
would be
not offensive. So, I put in big bold
letters on top of the doc, whoever wrote
this doc doesn't work at Open Door
anymore.
And I didn't realize that both the
consulting firms that the company had
hired to do PR for it were in the doc.
What happened is that happy accident is
both the consulting firms very loudly
resigned their account.
Like we were back to have nothing to do
with the company, which did two good
things. One, I didn't have to pay 30
days of notice.
And two, I got to have one less expense
on my
uh
on my income statement. So, I got every
expense the company
had paid for last 12 months.
And usually for tech companies, like
your largest expense to an external
vendor ends up being like your cloud
provider. But for Open Door, number one
was
millions of dollars
written to very large consulting firm.
This company had come in
and had told Open Door to basically
offshore every job
to
massively overload the company with G&A
and basically cut engineering, which is
literally what you do if you have zero
desire to create alpha. And that
basically happened to Open Door. And And
the way, I think this actually happens
to a lot of companies.
Where the founders are no longer there,
there is no large shareholder that cares
a lot about the company.
So, over time many of these companies
essentially become
hosts
for professional leeches, whose job it
is to suck the company dry while making
management look good.
>> So, I want to go back to day one, too.
Like we we started down this track of
you got all the expense reports. Like I
want you to walk me through and to give
me the blueprint of like coming in here
and
>> Yeah.
>> Because it
you find a culture that exists without
you.
>> Yeah.
>> How do you tell what to keep, what to
get rid of?
>> So, OpenDoor had gone fully remote.
So, at 9:00 a.m. that Monday, I told the
entire company, "Hey, OpenDoor's going
to be back in the office next Monday. If
you don't plan to be in my these
offices, we appreciate your help, but
you're no longer with us." Then the
second thing that happened was that
OpenDoor had become a place
where you succeeded by creating process
that had comes. So, a bunch of people
chose not to be part of company because
we became so outcome-oriented.
Uh because we demand ownership. But the
third thing that was impressive is I'm
just actually the best best could
surprise of OpenDoor. I would every once
in a while find someone
who I thought was exceptional.
And I would ask you ask them in that
first couple of weeks, "Why are you
still here?" And it was a series of
these people that had kept the company
alive on their shoulders.
And we've now rebuilt the company around
these ICs.
>> ICs are individual con-
>> Individual contributors, yeah. Who
actually do the actual work.
>> So, it was on life support.
>> Yeah, actually OpenDoor would have died
had it not been for maybe
a dozen people.
>> Well, so this is fascinating to me,
right? Because if you were to read a
book on how to turn around a company
or you were to go to business school and
take a course on like the best
turnaround, you're not doing any of
that. You're In fact, you're doing the
opposite.
>> There's a lot to be learned from books.
But, if OpenDoor could have been fixed
by following something that was written
in a book, it would have already been
fixed. Look, there's two things. One,
the people you hire is the company you
build.
So, the first week at OpenDoor, I
changed our career page.
Our career page used to say something
along the lines of "This is a happy
place to work where we all care about
each other, and by the way, here are all
of our ERGs." OpenDoor's career page now
says that "This will be hard."
Like, our job is to attract people who
want to work hard, and we don't like we
say this is not for you. Like, I my job
is to try to convince you to not work at
OpenDoor.
So, it shows that if you come, you're
highly committed. So, that's one thing.
So, the people end up being the company.
The second thing ends up being that over
a very long amount of time,
groups of people tend to have
tendencies
towards niceties.
>> Mhm.
>> So, everyone ends up telling each other
nice lies.
As soon as a white lie is detected, very
off course. And the job of a founder
type is to be, you know, a nuclear bomb
of truth over and over again.
First principle truth.
But, what is important is to discover
who you are,
discover that kernel of truth, and build
only on that. And then hire
exceptionally good people,
and guide them.
>> What was the view from the inside? Like,
was what for all of these nice lies sort
of aggregating into the company's doing
okay?
>> Yeah, I mean, I think I think a lot of
people
had convinced themself
themselves that bad things were
happening to OpenDoor.
That OpenDoor was like this victim of
the macroeconomic environment.
You know, the victim mentality that
people develop, right? Cuz you you know
people
who blame the world for everything that
goes wrong with them. OpenDoor felt like
that. The company was just mad at the
world, mad at its partners, mad at its
customers because it blamed the outside
world for everything that was happening
to it.
>> But like how do you change that? In in
the sense like you're one person, and
you're coming in, and you have to have
this equal and opposite force, I would
imagine, to counteract this and start
changing the culture. And And you pull
the curtain, and you're like, "Guys,
we need
>> Yeah.
>> I mean, I think I think that a
commitment to truth over feelings is
incredibly important.
I sent my team I have a blueprint
that I sent to the entire company
because my job was to create strong
repelling forces.
I.e., I wanted everyone who didn't like
how I was going to run the company to
quit.
>> You wanted people to opt out.
>> Yeah, to opt people out. And then that
would create room for people to opt in
from the outside. The most dangerous
people in any company, if you grab a two
by two chart,
are competent but mis- not
mission-aligned people. So, your job is
to identify who they are and help them
move on as fast as possible.
>> What makes them so dangerous though?
>> Well, because competent people have a
way of tilting the org in their
direction, right? Everyone has had at
their job someone who is very good at
internal politics, and you can see that
this person keeps getting promoted
because your boss doesn't realize what
they're doing. So, my job, I thought
early on, was to cause that rift to
widen. We've I've had to basically hire
an entirely new company,
and that has been very painful.
>> So, if you sat down and had a written
document on like the key principles
involved in turnaround a business, what
would they be?
>> I think changing defaults is incredibly
difficult. So, if you're going to change
a default, you have to do it violently.
Let me give you an example. OpenDoor was
remote. OpenDoor was never going to
become in person if we had a seven-step
plan over eight months.
I know this because OpenDoor had had
many seven-step plan over eight months
to become a person and never worked.
So, the only way to become a person for
OpenDoor was was through a significant
amount of aggression. Transparently, I
thought OpenDoor was a place where some
people were kind of mailing it in.
>> Yeah.
>> Not everyone, but some people. So,
um I stopped the office.
I thought OpenDoor was a place where
people were unwilling to take, you know,
risks. So, we took risks publicly. They
weren't like
You need to figure out which defaults
are killing the company
and change them violently. There must
not be change management
because you want the change to feel
jarring.
Second, you must tell people what you
expect of them.
Most companies' mission statements end
up being bland, pale imitations of
statements.
We're here for the good of the world.
Yippee, I who isn't?
Right?
But, you have to say things
that a reasonable person would say, "I
don't want any of that."
If you figure out what those things are
because it matters.
And third, I I I if you're starting and
uh as a CEO of a new company, I strongly
urge you this.
Be committed to truth
over feelings.
Truth over feelings all the god damn
time.
Because you will invariably, over time,
find that you will get rounder edges if
you're not careful.
>> Double-click on the truth over feelings
thing there because
I mean, most people think that they
already do that.
>> I think what happens
is people are truthful within the
context of the situation and the people
they're in the room with.
The larger the room is, the less space
is it there is for truth.
Right?
But, that is the death
of companies. This is why big companies
are so usually
average. I mean a pizza thing team is
real, right? Like the having small teams
is real because you can be truthful in
smaller rooms. You can say things you
would never say in a big room. And you
need to get that in a company if you're
like a new CEO of a company. You need to
discover who are the speakers of truth
and get them in a room alone so that you
can discover things.
>> Mhm.
>> Otherwise,
uh you will die.
>> So, what's a a meeting with Cazz like?
>> We try very hard not to have meetings
unless they're needed cuz meetings are a
bug in the system.
>> Wait, go deeper on that.
>> So, meetings exist because people could
not get the information they needed to
make decisions before the meeting.
>> So, most meetings are like context
sharing effectively.
>> so
typically, we only have meetings where
we're broadcasting not narrowcasting.
And our meetings end up being relatively
uh full of disagreement.
>> Go deeper on that.
>> So, there's no point to have a meeting
where we all agree.
And we believe it is impolite
not to disagree. Our meetings tend to be
uh louder than the average company's
meeting,
more ornery than the average company's
meeting, and like I mean it happens with
some frequency where people just leave
in the middle of a meeting cuz they have
nothing to contribute. It's impolite not
to leave a meeting in which you have
nothing to contribute.
So, our meetings end up being much more
um
collaborative and much less let me
present something to you.
>> How do you disagree without being
disagreeable?
>> So, in my blueprint I sent to whole
company,
I said I value being told I'm wrong.
Like our commitment is a truth is to a
truth.
When we make a mistake, OpenDoor made a
mistake. All mistakes belong to
OpenDoor. All information belongs to
OpenDoor. So, when you and I disagree,
we're not doing it because I dislike
you. We're doing it because I respect
you and I believe you and I are on the
same team. I wrote a post that I
published uh called say the thing
a while ago and it became
part of Shopify's lore and people would
say say the thing to me, which I
appreciated.
So, most people sit in rooms
or watch a Slack message and have a
large
disagreement, but they don't want to be
the person that, you know, uh farted in
church. So, they don't say what's on
their brain. So, when I got to Shopify,
when I was Twitter, when I got to
OpenDoor,
I was sitting meetings
where everyone
would act like everything was going
well.
But, things were not going well.
You could tell things were not going
well by shape of the chart. So, I wrote
a note about it at Shopify that hey, say
the thing. Say it now.
Like, the second you know something, say
it.
Say it about the thing, not the person.
Always say this sucks, not you suck. And
say it until you've been heard.
People don't have to agree with you, but
they have to hear you.
So, if you feel like you're not being
heard, say it over and over again until
you feel like you've been heard.
Because you get paid to do this at
OpenDoor.
So, it's incredibly important. Say it
now, don't wait. Second, say it about
the thing, not the person. Say it over
and over again until you've been heard.
And those three things are a cultural
expectation.
Not doing it is considered rude.
And this has been a very real part of
our learning at OpenDoor
is allowing people to object to things
that are stupid.
>> Do you think it's a turnaround or like a
refounding?
>> I think it's a new company because AI
has made it a different company. Because
look, what what about OpenDoor's
business is difficult?
The operational complexity of the
physical asset. And what do you need to
make that operational complexity go
away.
You need very low cost, fast
decision-making at scale with data.
We have built the AI exoskeleton around
every human being at OpenDoor. Such that
they can be three, four x more efficient
than everyone else. To give you a sense,
the last time OpenDoor bought as many
homes as we bought last quarter,
OpenDoor's OpEx was more than twice as
high. In a world where prices have gone
up for human beings,
we've become twice as efficient.
>> Every few years a new platform earns its
place at the top of every smart
advertiser's media plan.
The people who find it early build
advantages that are very hard to close.
Apple 11 just had the most remarkable
run in ad tech history, and now they've
opened that engine to businesses like
yours.
Over a billion people play mobile games
every day.
Focused, not scrolling, with no feed
competing for their attention.
Apple 11 puts your brand in front of the
right customers and optimizes purely for
your growth.
Brands like Wayfair, Kitsch, Ridge, and
Nectar are already scaling on it while
most of their competitors don't even
know it exists.
Ready to find your next million
customers? Go to applovin.com/shane
and launch your first campaign today.
>> Let me tell you about the best new
product that I've used in the past 5
years. It's the Matic vacuum. This thing
vacuums, it mops, Matic does everything.
Other robots bump into things, but the
Matic sees things. It actually avoids
the problems. And the Matic
automatically adjusts between my
carpeted surfaces and my hardwood
floors. It's also super easy to
schedule. I have it run every night
while I'm in bed, and every morning I
wake up to clean floors. Messes happen,
and when they do, Matic rolls into
action. Go to maticrobots.com today and
put Matic to work for you.
>> Do you think of AI as replacing people
and labor or do you think of it as
amplifying
the ability of
a particular person? I see.
>> I think what AI does is two things. One,
it lowers the the the lowers the need
for human management.
Right? If you look at any company, you
end up with these very long tails of
managers managing managers before anyone
does any actual work.
And AI, because it takes the
communication a barrier down so much, we
can share more more information more
broadly,
it just collapses
the company um chains in the company.
The second thing it does and what it has
done at OpenDoor
is AI fundamentally changes who wins and
who loses.
The people who use AI well will win and
there'll be more of them. OpenDoor has
more engineers today than it did when I
joined
because we use AI well.
>> What are the most powerful mental models
that you find yourself coming back to
over and over again?
>> Actually, you you know me a bit so you
know this is true.
Uh I I have these written down.
First, friction is underestimated.
Two, a map is not the train. Three,
truth over feelings. Those are like the
three.
So, let me give you the first one.
Everyone has seen
uh
the supply and demand graph in their
life. And what people underestimate
the
uh invisible hand of friction on where
those two things cross.
The total market size of Walmart
would have been massively
underestimated. Same with Amazon, same
with Google because before these things
existed, everyone thought the market was
smaller because there was so much
friction in the market. When you reduce
friction in a system, you just get a lot
more of whatever you reduce friction on.
>> Right.
>> And if you look at the OpenDoor
parallel, before I got to OpenDoor, from
the time you entered your
address into our homepage to time you
got an offer,
there'd be 11 people in the path, many,
many days, many, many processes, many,
many docs. All of it friction. And every
one of these we removed increased
demand. We're buying six to seven times
more homes this week than we did last
year this week.
And that's almost entirely because we
reduced friction. The second one is like
the map is not the train, which is like
I find the one that I wish I could teach
corporate America.
>> Mhm.
>> I think Hayek is just generally under
appreciated. He gave a speech called
Pretense of Knowledge, but the entire
speech is basically about this idea that
all of us
confuse the map for the train.
The train reflects the land.
If you were
in
Europe pre-discovery of the New World,
you would look at a map from an expert
and trust it.
Right?
>> Yeah.
>> Cuz everyone did.
It just so happens that unless you
recognize you're looking at a first
derivative of a fact, not the actual
fact,
you almost always will build models of
the world
that
end up drifting from reality.
And this is how companies go bankrupt
over time
because they continually drift more,
more derivative, more derivative. They
build models upon models, and no one
says "Excuse me,
like how far am I from the fact?"
>> But how do you do that? As a company,
how do you stay in contact with reality?
>> Dashboards are wonderful things, but
most corporate executives run the entire
company on dashboards, and that is a
derivative fact, it's not the fact.
You're playing like SimCity.
>> And you don't know when the environment
changes.
>> You end up losing a feeling for the
business. Ray Kroc,
the guy the the founder of McDonald's,
used to go into the kitchens.
>> Yeah. He'd be like, "There's too much
ketchup."
>> Like you watch Undercover Boss, and
they're always surprised by what's
happening in their company.
And again, I'm like, "Why are you
surprised?
Like how are you surprised? How did you
not know? Like what is the job if it's
not understanding how your product
touches the customer?"
>> But how do you do that as a company? How
do you stay in contact with reality, and
contact with the ever-shifting terrain?
>> I talk to our customers every single
week. Every single week. I go visit our
homes all the time.
All the time. I look at the raw database
all the time.
It's I build my own dashboards all the
time. And I find that at least that
gives me less ability to be um
fooled.
>> And it gives you a huge context window.
>> It does. You just have to just have to
do it. So the map is our trade. And the
last one which we talked about a bunch,
which is truth over feelings. There is a
level of suicidal empathy that people
have developed
that is just deadly. It is killing
our best companies because people are
are assuming that everyone is
thin-skinned.
>> Mhm.
>> And they're assuming that people are
offended by facts.
And I'm just sorry. Facts do not care
about your feelings. They just don't.
And it's incredibly important that
everyone be committed to truth.
>> I want to come back to the turnaround
for 1 second because
Shopify was a remote work culture, and
one of the first things you said you did
was everybody's in the office Monday or
you've opted out of working here.
>> Yeah.
>> Why?
>> First of all, I don't think remote works
generally. It only works for Shopify and
that's because
we built more software to make remote
work than anyone reasonably thought we
could. And I think the jury
has fully come back on this topic that
companies that are primarily remote end
up having slower cycles.
And if you look at startups, it just
tends to be true.
>> Why do you think that is? Like what
explains that?
>> You lose a lot of culture. It's very
hard to build culture remotely because
OpenDoor's core mission is difficult. We
need to make other things easier. And I
think the best thing everyone
intuitively understands, if you played
any sports growing up, you understand
that the thing that causes you to build
camaraderie is doing hard things
together in person and winning.
Like high school football teams have
amazing cultures.
>> Yeah.
>> Amazing.
>> Yeah.
>> And look, we do a very hard thing, but
we do it in person with our colleagues
shoulder-to-shoulder.
We celebrate our victories together and
the failures we see together so we can
actually get through them together.
That's one thing. Second, look, a lot of
communication gets lost at remote
companies. And third,
uh
intra-company multiculturalism does not
work.
>> What does that mean?
>> Companies cannot have multiple cultures.
They just can't. They just die.
If you allow a company to have many
different cultures, what you end up
creating is you lose all short form
of communication.
>> Mhm.
>> And you end up spending a lot of time
aligning people such that you can move.
And it's much easier to have a
unicultural company.
Much easier if you're in person.
>> Talk to somebody
inside the turnaround who who reports to
you now and he said
you've killed more things in 9 months
than most CEOs do in a decade. What did
you kill?
>> In my first
4 weeks, I killed two entire business
lines.
OpenDoor used to have essentially I we
provided general contractor services
to other companies.
Which is not a profitable business for
us.
But it's not the mission of our company.
Our our job isn't the world's best
contractor so we killed that. We had a
business where we essentially called OD
Select which we essentially were like
quasi builders that we would take
essentially homes that were like
unlivable and just build them from
scratch up. Profitable business line for
us. Killed it off.
Because again, it's not our job. There
are builders in the world. We're not one
of them.
We're a market maker. It's a different
job. If you think of
my time at OpenDoor, I think it's
reasonable to say I've only started
three products.
And we've shut down a few dozen.
>> You started mortgage.
>> Mortgage, our buyer product and our new
product cash down more later which like
existed in a
odd shape but existed in a meaner and
much much
realer way.
>> What does it mean to be a market maker
in housing?
>> Yeah, so if you look at the history
of assets,
the way assets grow on the internet has
been basically similar. First, someone
solves the discovery problem. I need to
find X. Uh Craigslist
is the best example of this. Then
someone comes and says, "Okay, you know
what? I can build trust essentially now
you have found something, you know who
you're dealing with. I build a trust
layer."
PayPal.
>> Mhm.
>> Is a great example of this. Actually,
eBay discovery, PayPal trust. I will
allow you to trust your counterparty.
>> Yep.
>> And the third
player almost always tends to be someone
who says, "Great. I will help you both
find
something, trust the counterparty, and
underwrite the risk on both
transactions.
Amazon. And usually
in the marketplace of like the under
internet, the third player wins.
Because they reduce the friction, so you
can have a much more volume, right? If
you go back to 2002, everyone thought
eBay was going to win against Amazon.
>> Yeah.
>> But clearly has not happened.
Amazon won because it solved the full
problem. Now it's a much harder problem
to solve. So the job of the market maker
is to stand between two people
who want to transact
and allow them to transact with you such
that they don't have to actually look
for each other and find them. And that's
our job for housing, right? The largest
problem in housing is that people want
to move and they can't cuz they have not
found a buyer for their home. And our
job at OpenDoor is like, we're that
buyer. We will buy your home. Come to
opendoor.com, type in your address,
we'll buy your home at a fair price, and
then we'll sell it to someone when when
that person is available.
>> So how does OpenDoor make money then?
Like how do you become insanely
profitable doing that?
>> We make our money in two ways. First, we
make money on each transaction
relatively thin margins on each
transaction. But we make our real money
from the first derivative of the
business, which is
uh mortgage, insurance, title and
escrow, all the things that go with a
home. So our job is to buy and sell the
home
at fair prices as fast as we can and
make our money on the services you get.
This, by the way, is how we built
Shopify. If you look at Shopify,
you can buy Shopify the software for $1.
Like and it's $1 cuz it can't possibly
be less.
The credit cards won't let you charge
less than a dollar. And Shopify makes
most of its money by you succeeding on
Shopify, by a services it provides you.
And this has always been true. People
misunderstand how businesses work.
It has always been true that some of the
biggest companies in the world have been
built on the first derivative of the
core business.
Google does not make money from you
searching for things. Google makes money
from showing you ads while you're
searching for things.
>> How did you learn this concept?
>> I've just been always interested in the
history of companies.
It just seemed relatively obvious to me
that that's what had happened in the
world.
That these ancillary businesses to core
business had become the real thing
because
if you had how software grew,
the way software used to be sold is you
came to me
for software. I wrote some code and
handed it to you and then ran away cuz I
would make all my money from like the
implementation, right? And then SaaS
came along and SaaS companies said,
"Hold on.
I will make money from you over a very
long time from the relationship."
And Shopify came along and said, "Cool.
I will make very money from you for a
very long time over a relationship, but
from services, right?" And that pattern
has always held true in every business
cuz there is a word for people who make
all their money from you up front and
never talk to you again. We call them
carnies.
Like they come to town, they just get
take your money and run away.
>> Yeah.
>> Like that's not how businesses work. No
one trusts someone
where you know that the second this
relationship is over, you'll never see
them again.
But that's how the largest asset people
have transacts.
That's crazy. It is insane
that this is how we deal with the
largest asset class in the world.
You would never trust a stock broker
that made all their money from you from
one trade. You would just never trust
that person.
It is very real that like for the good
of a relationship, it is important that
you and I be committed to knowing each
other for a very long time.
>> I built an AI version of myself with
HeyGen. Today, I'll have it dig up an
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Shane,
you once predicted that long form would
beat short-form for anything that
actually mattered. Create that
prediction today.
>> Hey, I was directionally right, but I
underestimated just how much short-form
would become the front door to long-form
content.
>> I agree you were right, but for the
wrong reason.
You thought attention spans would
recover.
They didn't.
People just got better at choosing when
to go deep.
Right call, lucky logic.
>> Well, I got the right answer with the
wrong math, but I'll take it. That's
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and get an AI avatar that delivers
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That's drinklmnt.com/tkp.
So, one of your principles was sort of
>> say the thing, but I was surprised
another one was
get [ __ ] done.
>> Yeah.
>> Why do you have to tell people to get
[ __ ] done?
>> So, let me tell you a story. Toby's Toby
Lutke is among the most thoughtful
people on the planet. There's a reason
why people call him the founder's
founder. This you walk the offices of
Shopify, first of all, they're
incredibly thoughtfully designed,
but they also on the walls, um, do
things tell people.
And
I always find that was odd. I actually
haven't had a conversation with Toby
Bottis, but like I realized that like
in most companies
the order is reversed.
>> Mhm.
>> Like in most companies is tell people
then do things. In most companies this
is what happens. You have an idea.
You spend a lot of time writing memos
about that idea
to get buy-in about that idea before you
can have a meeting so that they can
approve that idea.
And there's a whole process that takes
many months before you can do the thing.
The chain of command is designed to
minimize risk.
And
there's two ways to deal with that.
Chain of command.
The first is to do what Amazon said.
Amazon became a default yes company.
Most companies are default no. The chain
of command is designed to reduce risk
and say no to many things, right? That's
what it does.
Amazon has said
no, no, no.
We're a default yes company.
Which worked incredibly well well for
Amazon.
But I think a better way to deal
with this problem is to not have the
chain of command.
Like to minimize the number of people
who can say
no.
>> Yeah.
>> And only have people that you want and
trust to do things.
This by the way is not
People are designing this whole thing. I
want to give you this very specific
example. I got to open door and I
realized that first substantial number
of homes we had bought
the person who was supposed to manage it
would show up
and the power would not be on in the
home.
And when this happened
the person was managing the home would
get a notification hey, power isn't on.
And who that this person would have to
go to salesforce, fill out a form.
That form would get emailed to someone
else. They would look at it. Then they
would ask for permission from their
manager to turn the power on.
Then they would call the utility
company, turn the power on. They would
mail something It there would be a back
and forth that involved three or four
managers. And I thought this was a nutty
system ever. So, we literally gave
everyone corporate cards and said, "Hey,
if you see a home whose power is not on,
if you type in the address into Slack,
you will get back the phone number
you're supposed to call, the account
number you're supposed to say,
and the credit card number you can give
them to turn the power turn on power."
We're the largest buyers of homes in
North America.
And but I opened it up. Our world was
not run by
uh
unintelligent people. They were highly
credentialed people.
But the general incentive inside every
company is to reduce risk as much as
possible.
And the way you reduce risk is more
process, more people in the path. So, do
things becomes actually difficult.
>> I think of this is like
nobody would want to wake up in that
state, right? Like you would never
create the end state that they were
operating in as like the goal.
So, somewhere it just gets like 1° off
course, you know, and that 1° starts to
compound as time goes on and on and on.
>> This I think I'm going to I'll use our
pilot example. I want to be a pilot, my
wife won't let me.
>> Uh smart.
>> Uh I
>> Listen to your wife.
>> I have a bunch of plane analogies.
But there's a very real thing that
happens to new pilots.
New pilots go into the into clouds
and they turn slightly, slightly,
slightly, slightly.
>> Mhm.
>> And people say you'd be surprised by a
number of new pilots who come out of sky
clouds fully inverted. Cuz you basically
end up upside down
1° at a time. That's basically what
happens to every company.
This is a very good sign that your
company is upside down if you have
acronyms.
If you have a lots of acronyms, the odds
are you're upside down as a company.
Because acronyms are things that people
do when they want to create in cultures
and out cultures.
By definition. So, if you have acronyms,
the odds are what you have done is
create so many in groups and out groups
that no one can tell that anyone else is
inverted.
And the only one who can tell someone is
inverted is someone above the chain who
can look at both of these things.
Unfortunately, most corporate CEOs don't
go that deep.
Right? They They manage the dashboards.
>> This comes back to sort of like trying
to touch reality and being in the weeds
and having a bigger context when
>> turned on utilities.
I've fixed work orders. I've like cuz
you have to do it. Otherwise, I don't
know how you
Like I mean Elon famously sleeps at the
factory.
And people think it's like a meme.
People think he does it for show. I
don't think he does it for show.
I think it's literally the only way to
do things.
>> Well, that sort of begs how important
are the words that we use to communicate
ideas? Like how do we make ideas more
transferable
in a company?
>> Yeah, um
early on in my career, I used to ask
everyone who worked on my team to read
Orwell's essay
uh Politics and the English Language.
It's an incredibly good essay.
Because in it, he talks about how
English is among the most powerful tools
ever invented by humanity.
In the English language, and I say this
as someone who was not English is not my
first language. But Orwell says
English is in trouble because words have
lost their meanings. And the word he
uses is fascism.
In the essay, he says fascism doesn't
mean anything anymore cuz everyone's a
fascist.
Like everyone gets called a fascist.
Anyone I don't like is a fascist.
Therefore, fascism doesn't mean anything
anymore. I used to share this essay with
people I with because in order for
language to be useful, we must hold it
properly.
And English is an incredibly powerful
powerful tool if you speak simply.
And that is an incredibly important
thing to learn inside a company. As a
company they guard against it because
most business talk
is designed to confuse the listener.
Deliberately confuse the listener.
I challenge anyone
to find any sentence that includes the
word leverage that means anything.
>> Hm.
>> Like it just means almost nothing all
the time.
And there's a series of these words that
are very common
in the corporate world
that are designed to have a low density
of information to words.
>> And and they're sort of ambiguous,
right? So, it's like I can weasel out of
whatever happens because this word can
mean multiple things.
>> Yes, it's very And there's another one
by the way that that
it's
the passive tense is
another example of this very The passive
tense is very bad, but even the worse is
um
othering of facts. Let me give you an
example.
Legal decided that X would be true.
>> Hm.
>> I have a rule at OpenDoor that people
decide things, not teams.
>> Yeah.
>> So, whenever someone says legal decide
X, I'm like, "Who?" Legal doesn't get to
decide a thing.
>> Yeah.
>> Like, what's the name of the person?
Because if you name the person
what you are doing is you cannot
round the edges of what they said. This
is how you end up
uh
mutating everything into bad by taking
away specifics of the situation and
living with generalities.
Like you get a pale pink imitation of
everything.
>> Yeah. When I look at a company, I sort
of look at it through strategy,
operations, capital allocation, and
people. How do you look at a company?
>> Product smart. I think of products
first. I really do. I think most people
overemphasize strategy.
>> [sighs]
>> I'm not saying strategy isn't important,
but it's usually not that complicated.
There are very few businesses where
strategy has been the cause for the win.
Usually, it's exceptional execution by
the one company that shared the same
strategy as seven other companies. It's
just the best executed one. Google's
strategy was not meaningfully different
than the other 25 search engines.
Its execution was different. I think
strategy is important, but far less
important than people think it is.
I think what tends to be very important,
and far more important than people think
it is, is the product.
Like, is the product deeply useful to
the end user?
Uh can you find 1,000 people who love
the product?
And if you can, you're on the right
track. If you can't,
all the capital in the world won't save
you.
>> How do you think about risk? A lot of
people think, you know, for instance,
that delaying a decision reduces risk.
>> I think I think it almost always does
the opposite.
Like, there are very few decisions
that gathering more facts
will help.
I actually did this the other day.
I was in a meeting and some one of our
um colleagues said,
"Hey, we're going to run this AB test
and then decide what to do." And I said,
"Great. Guys, I'm from the future.
I'm from 6 weeks from now.
The AB test was 51% positive. Tell me
what you're going to do.
What most tech companies end up doing,
and I put the AB test are like the most
because people misunderstand
um statistics and misunderstand
like
what a mean average error means
and the compounding nature of mean
average error, people misunderstand
these things.
What
for most tech companies AB tests have
done have been the safety blanket
>> Mhm.
>> for management.
>> I don't have to make a decision.
>> Like this is like uh Google famously AB
tested some like 400 different shades of
blue.
>> Yeah.
>> Like dude, it didn't matter. I promise
you it didn't matter. It reverted to the
mean. It could have been any shade of
blue. It would have been fine. I'm not
saying that AB tests don't matter, to be
clear, I'm not saying that. But what I
am saying
I'm saying AB tests
>> matter a lot.
>> But
they cannot replace human judgment.
>> Of course, yeah.
>> And if you stand in a room and tell me
like a one slight deviation of shade of
blue matters, I just don't want to be in
a room with you.
>> There's a lot of people in life that I
feel there's a parallel here.
There's a lot of people in life who
feel lost, maybe a little bit
rudderless, the North Star is not there.
They know they're capable of so much
more.
And the parallel to me is this is like
OpenDoor when you come into it. You
know, things aren't working as good as
they could be. There's still a
heartbeat, and you're sort of going
through the motions, and you're on this
slow road to death. Like how could
somebody apply these principles to their
life outside of the corporate structure?
>> If you know anyone who has had a problem
with alcohol
>> Mhm.
>> and their life is draining away. What
usually happens
for them to turn around is an
intervention. It's a deeply
uncomfortable
moment of truth.
>> Yeah.
>> The first step is taking ownership over
the problem.
Right?
They take ownership saying, "I
understand there are things I can do."
Right?
There's a reason why
um
AA works so well.
Like cuz you do things. You track your
accountability.
Like day one, week one, month one, you
track over and over again thing your
accountability. And you don't write
thing over and over again.
And the score tends to take care of
itself.
>> Mhm.
>> Over a very long period of time. And I
think that pattern tends to be
one that is repeatable over and over
again. If you look at yourself
and say, "I am to blame for my
problems."
As hard and as someone who does it
more frequently than the average person,
it can feel lonely.
Uh luckily for me,
uh I have an incredibly supportive
family.
So those days where I say, "Hey,
I made a mistake. I am to be blamed."
I have uh my wife and my kids and that
makes
a world difference. I also pray more
than the average person.
So it helps me find
the ability to look at the mirror and
say, "You screwed up.
You should do better. You can do
better." And then just like
feel that I'm not holding my past self
guilty, but just do better. And I think
that pattern is as repeatable
um in companies as it is as it is in
people.
>> How do you not hang on to that? A lot of
people go through that. They make a
mistake. They'll even admit that they
made a mistake, and then they become
paralyzed by fear.
>> I have high degree of sympathy to people
who do that. I really do. One of the
best
parts about being a founder, which is
why I think founders are such unique
characters,
basically every founder I know has had
to look
at like a bank account statement and
count how many payrolls they I I away
from like not being able to make
payroll.
>> Yeah.
>> And that usually shakes you pretty good.
>> Yeah.
>> Cuz if you do nothing, you're dead.
Like you're dead Like Paul Graham has
this essay where he calls it default of
dead.
And you have to do something.
Like action creates information. You
have to do something.
Uh and like so I think that
allows founders just to act differently
than other people would.
But I don't I don't want to pretend like
I know
I know all the answers, but I can tell
you this.
You will find that the first thing to
fix will
is easy, intuitive,
and makes you feel good. And people who
win tend to win over and over again.
So the analogy I use internally at
OpenDoor is this.
Chemical spills
are notoriously difficult to solve
and clean up.
But what if you arrive at a site of a
chemical spill,
the first bit is really easy to solve.
Just grab a shovel.
The last bit requires a bunch of
microscopes and [ __ ] But the first bit
is shovel territory, man.
>> It's like your grandfather's wisdom,
right? When you find yourself in a hole,
stop digging.
>> Yeah, yeah. Yeah, no, it's real.
>> It's interesting you sort of mentioned
not making payroll, and you know what
that made me think of is the moment
Steve Jobs, if there was one moment
where Steve Jobs became the Steve Jobs
that we all remember, it was the '93, I
think it was bankruptcy of the hardware
division at NeXT.
>> Like that was the moment where he
started to change his behavior.
>> In the movie, there's this very famous
scene
where uh Steve Jobs had fired uh the
Apple II team.
And was as like, you have to recognize
these people.
Like they worked hard, you have to
recognize that they worked hard. He gets
angry. He's like, "You almost bankrupted
the company."
Like there is a very real thing that if
you have come close to death,
>> Yeah.
>> if you look at the balance sheet, you're
like, "Holy
God, I only have X number payrolls
left."
You do not care at all what it looks
like. You just care about what it is.
You realize that you can put up with
more pain than you think you can.
Like everyone has a higher pain
tolerance than they think they have.
>> Is part of that sort of not caring what
other people think?
Like the courage to be
>> disliked and thinking Yeah.
>> So many people optimize their life in
order not to be disliked versus on
mission or towards a goal or
>> First of all, Courage to Be Disliked is
an excellent book. Everyone should read
it, but it's a very real thing where
most people's limitations are
self-imposed.
>> We're capable of so much more.
>> Yeah, with like everyone is.
And everyone's pain
uh is more imagined than you think it
is.
And this you intuitively understand it
when it comes to everyone else, but in
yourself, you have a hard time
dealing with that. Running a public
company is incredibly difficult
if you care what the Wall Street Journal
says about you.
>> Mhm.
>> I just don't.
I've never cared.
>> Is that learned? Or something you
>> I just think what happened was I
immigrated from Iran, my family fled
Iran.
And when we moved, I was a teenager.
And I didn't get into any clubs. And by
the time I was a grown-up and I could
get into clubs, I cared way less about
them.
So, I just grew up
making uh
>> [laughter]
>> making a feature out of necessity.
And that, I think, has played a very
large role in
uh
in my life.
And there's a second thing which is very
real.
I played rugby
uh in
uh in high school.
And I uh am not
a big dude.
But I'm fast and have a high pain
tolerance.
And I really, really enjoy winning as a
team. But rugby's actually a special
sport for this. It's crazy.
Uh
it tends to be a sport that if you play
in North America, it basically never has
an audience.
Like no one goes to watch rugby games in
North America, uh really. So, you do it
for your friends, you do it for your
teammates, not for the audience. But you
get something better out of it, which is
like this idea of like being in pain
while winning as a team.
There's like something very deeply
joyful about bleeding out like out of
your knee while winning as a team.
>> Is it or Sharp who founded Four Seasons
said, "Excellence is the capacity to
take pain."
>> Mhm.
>> Do you agree with that?
>> Yeah. Yeah, over a very long period of
time, by the way.
The person who can hold their hand over
the fire the longest tends to be the
winner. The difference between doing
something incredibly well and doing it
poorly
is not that high. But people just give
up too soon.
Unfortunately,
I think
the sugar rush of easy
like satisfaction
in the modern world has under-prepared
people for pain.
>> We always end these interviews with the
same question, which is what is success
for you?
>> I have four kids.
Um, they're seven, five, three, and two.
And I care a great deal
about what they say to their kids that
their dad did. When my wife and I got
married, we agreed that we would
optimize our marriage for putting a dent
in the world.
That that's what we'd spend our time on.
Um, and that that would be our
definition of success in our marriage.
So, I try
to wake up every day
and think what is the most
the thing I can do that leaves the
biggest dent in the world. Like, I think
most people in my position
would have looked at the OpenDoor
opportunity
and
uh, not ride full speed.
But, I ride full speed because this
feels like a problem of a shape
that I should be able to solve for the
world.
And my team and I should be able to
solve for the world. So, that's what I
want to do. I want my kids to grow up
and be able to be proud of their dad's
career because, and this is important,
because they are sacrificing a part of
their childhood
and
for my career.
Like, I'm not around as much as I should
be.
I don't put them to bed every night. And
it matters that that time away from them
is used for the good of the world.
So,
I hold myself accountable.
And thankfully,
my wife also holds me accountable
to that end.