April 21, 2020 • 44 mins
This episode features one of today’s top technology leaders Dick Costolo.
Dick is an investor, currently through his fund 01 Advisors, and advises countless CEOs, Governors, and world leaders, as one of the most sought after minds in tech.
He was the CEO of Twitter from 2011 to 2015, took them through IPO, and he also advised the show Silicon Valley on HBO.
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Episode Transcript
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Speaker 1 (00:01):
Art of the Hustle is a production of I Heart Radio.
You're listening to the Art of the Hustle, the show
that breaks down has some of the world's most fascinating
people have hustled, strategized, and learned their way into achieving
(00:22):
great things. I'm your host, Jeff Rosenthal, co founder of Summit,
and in today's episode, I'm excited to chat with a
mentor and advisor of mine and a straight living legend,
Dick Costello. Dick is an entrepreneur and investor, advisor to
governor's presidents, CEOs, and an HBO show or two. He's
the former CEO of Twitter and currently invests out of
(00:43):
his fund zero one Advisors. Welcome to the Art of
the Hustle, Dick, Thanks for being on the show. Happy
to be on the show. So, uh, we were just
talking briefly before we pressed record, and you were telling
me that you guys had a full vegetable garden. Um,
where are you in the world right now? We're in
We're in Napa. We have a little tiny property in
(01:06):
the middle of all the vines. We don't have we
don't have any grapevines, but we just have a place
in the Valley and Nappa So it's kind of you know,
it's just farmers out here. Now. There's nobody up here
because the wineries are all close, so it's it's just
farmers who are dealing with their grape vines. And then
we have a big vegetable garden, so that's coming and
really coming in handy. Yeah, it is. The real luxuries
(01:28):
in life are emerging. You know, I think that we
were taking a lot of these things for granted because
of like the unbebelievable amount of options we have for
all of like you know, life's the exotic things that
become the day to day and necessities. Yeah. No, we've
got a ton of you know, we've got a ton
of like kale and collared greens and art of chokes,
(01:50):
and I mean you usually think like, oh, we've got
way too much kale or way too many art chokes,
and you know, you give a bunch of away now
it's great, Um, just go out to the garden and
get it. It's really awesome to have something like that.
It's sort of it's really a luxury. This thing that
goes from like you just said, this thing that goes
from Oh it's cute two. Oh. It's a total luxury
(02:14):
to be able to have that right now. It's awesome.
It's such a stereotype of like Silicon Valley swashbuckling CEO
goes to you know, garden kale or chop wood or
baked bread. But it's real. What do you think that? Why?
Why do you think that? That's a common practice where
you'll see a lot of the thought leaders in your
(02:34):
space that have this total like left brain right brain
switch um into you know, remote vipas in the style hangs.
I'm not doing any silent meditation retreats or sweat lodges. Okay,
I don't know. I'm just always like I can't. I
have to be busy, you know. I just have always
(02:55):
been that way. I had a I had when I
was in sixth grade. I got my first job. Um
you know, since I was in sixth grade, one of
the only things I could do was go be a
golf caddy and a country club because you know, I
couldn't get a eleven years old twelve years old can't
get a regular job. And uh, you know I was
up at like five am on Saturday and Sunday morning,
so I could get there early. So I could get
(03:16):
out twice and make more money. I just so you
were eleven years old. This is Royal Oak, Michigan, that's correct. Amazing. Uh.
And I know you went to University of Michigan and
you've been you know, in the game in terms of
technology and Silicon Valley and you know a lot of
these generational companies Google and Twitter, etcetera for a long
(03:37):
long time. But it sounds like, you know, at eleven,
you already had the hustle. You already were you know,
motivated itself motivated. But why why did you want to
run two routes? Uh? And that fashion? What did you
want the money for? What was the what was the motivator?
I don't even remember. I just was like, I gotta
get there before anyone else gets there, so I can
get two rounds in so I can make you know,
(03:59):
you know, forty buck instead of just making twenty bucks.
Because if I only get out once, I'll make twenty bucks.
And i'll make get out twice, I'll make forty bucks. Um.
And I just saved it all, you know, I didn't
spend it on stuff. I just saved it all for college,
you know. And I was able to even though I
did that for like three years, I think it paid
for like, you know, a semester or something at University
of Michigan. Um So, the hustle to return back in
(04:23):
those days, for even back then, for higher education in
state higher education at a public school. No less, I
still wasn't still wasn't too terrific. But it's like had
this like, um, you know, I just always wanted to
be moving, you know, um just from way back in
the day. And then my dad got me one of
the very first personal computers, this Radio Shack TRS Model eighty,
(04:47):
and I just started learning a program on that. So
even when I went to school to even when I
went to Michigan, I already knew I wanted to study
computer science. I kind of knew what I was gonna do.
And was it already? I know, I know today it's
a pretty legendary engineering computer Your science school was it
then in the eighties? Um So. The funny thing was
in the eighties the computer science department was in the
(05:07):
Humanities school, the literature science there it's called l S
and a literature science and the arts liberal Arts school.
It wasn't it wasn't in UM in the engineering school
the way it is today. So the crazy thing that
happened was because I was in the literature liberal arts school,
I had to have a certain number of humanities credits
when I graduated, and uh and that meant senior year,
(05:32):
I took a bunch of like theater classes because I
was like, I need some stupid arts credits to graduate
and uh and I got the bug from doing that,
And so when I graduated, it's sort of a bunch
of told the story a few times. But when I graduated,
I turned down all myine like programming jobs at companies
like you know, I don't know, Burrows and Honeywell and
(05:54):
those kinds of places, um and and went to Second
City in Chicago to try to um just become month
improviser and get on Saturday night life. So ditched everything
and went to Chicago and did improv comedy for years.
And uh and you told you know we were hanging
a few months ago and that it was the first
time I had heard this. But if Steve Carrell was
(06:14):
in your Second City class, correct, He and I showed
up almost the exact same time there, and we're in
one of the first they launched this thing when we've
gotten there, called the Second City Training Center. It was
basically like, hey, if you want to, you know, perform
a Second City like everybody else who comes to Chicago,
and uh, you know, then you got to go through
this program first. And he and I were in the
(06:35):
second group, I think, in the program, and we sort
of showed up there the same day, um with a
bunch of other you know, a bunch of other people
were all there at the same time. Um, you know
over the years, uh, Tina Fey of course, Adam McKay, um,
Horatio sans Um, Gosh, Rachel Dratch and you know, Matt Walsh,
all the UCB people were there at the same time.
(06:56):
So it's really cool, fun time to be there. And
do you see, like what are the overlaps. I'm sure
you've thought about this, but in terms of like leadership
skills and improv comedy and how do these things in
your mind connect, oh man, like tons um. First of all,
in improv comedy, I mean first, the very first thing,
(07:17):
you know sort of you figure out if you if
you and if you don't, you don't last very long.
Is listening is the most important thing to be doing
on stage because there's not there are no objects on stage.
You're just making it all up as you go along,
and and watching what the other people and are doing
and listening to what they're saying as they make it up.
And if you don't listen, you know, the scene doesn't
(07:37):
really go anywhere. So kind of beat into you early
on listening. Listening. Listening is the most important thing you
can do to help propel a scene forward. And that's
the you know, I used to tell my managers at Twitter,
listening is like sevent of what managers should be doing.
You know, your job isn't to make all the decisions
(07:57):
or be omniscient. Your job is to other feedback and
get the best information and make sure the best decisions
are being made, not to be omniscient and make all
the decisions and tell people what to do. So I
mean there were tongues of overlap there and then and
then secondly, I mean even even sort of created this
sort of you know, I just one of the beautiful
(08:18):
things in improvisation is this notion of yes, and where
everything that someone initiates you just accept it as fact
and accepted is the truth. Whenever they initiate something on
stage and the idea of yes and was, I accept
that that's now the truth of what's happening in this scene,
and on and on top of that, here's something I'm
gonna add to that. And it's instead of saying you know, no,
(08:40):
that's not true, which stops the scene, or asking a
question which doesn't propel a scene forward, we're saying yes,
but which directs a scene in another direction. The idea
of yes and was, I'm just gonna accept what you
said is the truth, and and we're gonna go forward.
And so we sort of got to this point at
Twitter where I realized people were not taking risks or
(09:03):
not taking chances because they were, um, you know, they
don't want to get in trouble or they're afraid of
breaking something, so they'll instead of initiating something, they'll go
ask for permission. This happens at all, by the way,
not just Twitter. As an organization grows and gets over
some you know, some some number over the dunbar number
of number of people you can know in a company. Um,
(09:25):
folks will start to go around and ask for permission
to be able to do things, and people won't say no.
They'll generally say you should go ask these four people,
and you know, pretty soon it's three weeks later and
nothing's been done because the person is checking off, you know,
everybody on the checklist of permission they have to get.
So at Twitter just instituted this bias to yes and
bias to yes was assume the answer is yes. You're
(09:47):
not allowed to You're not allowed to tell people they
have to go ask other people for permission. You know,
if if M, if someone you're directly reporting to doesn't
tell you, you're not allowed to do something, you know,
no one else's no one else is allowed to tell
You've got to go people for permission. Assume the answer
is yes, communicate what you're gonna do and do it.
UM and that is that sort of stuff was all
based on improvisation and was enormously helpful. And you've told
(10:11):
me you've shared some advice with me in the past
that you've told me is also pretty widely applicable. That
you had mentioned in UH in that which was you
know that a lot of you know, talented people UM
that run organizations do get stuck in this self limiting
you know, I'm doing everything or involved in every decision
or directing, you know, vision on all these different departments,
(10:32):
whether you are like the idea of stopping making all
the decisions? How common is this? How often when you're
you know, working with your portfolio companies, where you are,
you are you sharing this advice and help help us
understand a little bit better. Always I mean to tell
people like, don't you know? First of all, when leaders
tell people what to do, you know, it removes all
(10:54):
the ownership from the person's sense of you know, say
you tell your you know, I don't know, you're so
your your manager and you and you tell someone what
to do instead of letting them find the solution or
helping them find the solution that that they've come up with,
they don't feel accountability to it. They don't feel ownership
of it because you you know, if it doesn't work,
they're like, well, you know, Dick's crazy and he had
(11:17):
this stupid idea. I guess I'll go see what he
wants to do next, instead of if it's their idea
and they come up with it and they feel real
ownership of the solution and it doesn't work, they're gonna
figure it out. But you know, I got to figure
out how what to do about this? Because this was
my idea. So trying to hold people accountable for something
when you're the one telling them what to do is
just creates misery. Um, and it's not particularly a high
(11:38):
leverage juice of of you know, anybody's time. I remember
Bill Campbell, you know, the famous sort of executive coach
um who was on the Apple board and was famously
Larry and Seragey and Eric's coach um. You know when
I was when I was first CEO at Twitter. He
sat in the back of the room in a management
team meeting and I thought it was a particularly good
(11:59):
meeting because it made all these decisions and uh we
left the room and I thought, I was like, you know,
what do you think? You know, I'm pretty psyched about myself.
He was like, that was a d you know what
are you talking about. It's like, he said, let me
tell you something. When I took over a CEO of Claris,
they spun out Clara Software out of Apple. It's like
making all these decisions because now I'm the CEO and
I should make all these decisions. And this woman who
(12:21):
was one of my senior vice presidents who would come
from Apple with me, named Donna Davinski came up to
me after the second week and said, Hey, Bill, if
you're gonna make all the decisions, I'm just gonna go
back to Apple and you can pay someone a lot
less money to do this job. And sort of like
hit him on the head that you know, he's got
all these smart people in the company. Let them own
their solutions, and and you know the CEO should really
only be making the decisions that only the CEO can make. Um.
(12:44):
I think that's true, and I tell people that all
the time, Like, while we've got all these really smart
people around the table, if you're making all the decisions, man,
it's such a I think give When you're a young entrepreneur,
you want to like hit the game winner, you know,
you want to like be the player, get the celebration
and retire the jersey. And then as you get older,
you're like, man, what a limiting factor if like I
(13:04):
have to be the one and then you you know,
I I remember, you know, and I'm not you know,
particularly great manager or business builder. I think, um, you know,
I'm very much empowered by a community of people around me,
Like I have a very flat wide, you know, incredibly
talented team that helps us have such like, you know,
sort of a wide breath at summit. Um. But when
when I you know, I recall sucking at work for frankly,
(13:27):
like six eight months. It was around the time of
having my first kid. I was like, man, I just
have to change the way I do things, Like if
I just hustle or my working harder or more involved
in all these things, like, it's not gonna you know,
it's just only going to forever incrementally change the outcome. Um.
So I just remember having to actually stop and pause
(13:48):
and and you know, work differently. Um. And I've asked,
you know, other people on the podcast about that. They're like, yeah, dude,
that's just called getting older and getting smarter. I wonder
how you think about that transition. Yeah, I think, well, so,
first of all, you know, there's a reason that younger
entrepreneurs do that. It's because when they started the company
and there are eight people around, you know, and and
(14:10):
now there's five people because they've been successful and they
scaled the the action was reinforced. Hey, uh, two years
ago when I dive bombed that product meeting and said no, no, no,
that's stupid, let's do it this way and wrote the
new thing on the white board. Look, it worked. So
you know the reason they got to a successful company
that's now growing is because when there were ten of them,
(14:33):
they did this a lot, and you know, it works,
so I should keep doing it. You know, you just
have to learn as you migrate from building a product
to building a company, building and scaling a company. UM
to let people feel real ownership over decisions, and ownership
is accountability with authority, Like I have the authority to
figure out what I want the solution to be, and
(14:55):
then I'll I'll feel a lot more accountable to it.
If you tell me what to do and then get
mad at me because it did work, I'm not gonna
feel very bad about it. And you know I'm not
probably you know, probably gonna sit there and well, let's
just wait to see what Dick tells me to do next.
It's not a very it's not a very scalable or
high leverage solution. UM. So I always looked for I
always try to help CEOs with you know, just always
(15:18):
be thinking about operating leverage and operating efficiency and how
can you get more what's the highest leverage thing you
can be doing right now? And what's a higher leverage
rate way to run that meeting? Those kinds of things,
will you expand upon that the highest leverage way to
run a meeting? Yeah, Like so for example, sit in.
One of the things I'll do is you know, when
I'm just getting involved in a company, and I'll just
(15:39):
ask to like, let me just sit in the back
of the room and a management team meeting and take notes.
You know. And again these are companies that are remember
they were like all businesses, they are small. They sit
around a table, they try to figure out what to do,
They check in with each other and grows and grows
and grows, and um, you know there's now there's a
hundred fifty people and you know, get to sit in
the management Monday. And I mean, I'll give you, uh
(16:02):
an example from a couple of years ago, sitting in
the back of the room. There's nine people in the meeting.
No one's taken notes. It's an hour and a half
two hour meeting. We're going around the room, people are
doing status updates. And I'm already right downline a notes
Like there's four people in this company. Now, like, why
are we spending the most expense? One of the most
expensive meetings in the company with the entire leadership team
just doing status updates. We could have done this in
(16:24):
a Sunday night email. Um, we should be talking about
you know, contentious decisions that we need to make where
everyone's not on the same page yet, or the strategic
landscape or the competitive landscape, or a deal we lost. Anyway,
and we leave the meeting and you know, much like
me and much like me walking off with Bill Campbell
after several years ago, I walk up the CEO and CEE,
(16:45):
I was like, what do you think? Pretty good? Hut?
And I said, how many action items came out of
the meeting? And the CEO sessing, like, uh five? You
know that guy took that one? Um, a VP marketing,
she took that one, and I took two like and
so I said, well, fortunately I took notes. No one
else took notes, but I took notes. There were nine
action items that came out of the meeting. We already
(17:06):
know that you forgot what five of them are. So
next Monday's meeting is gonna be you know, and just
you know, creates misery for people, right like next I said,
next Monday, And next Monday's meeting, you're gonna have a
conversation something along the lines of, hey, where's that metrics
dashboard we talked about last week? And someone will say,
weren't you gonna get me the requirements for it first? No,
(17:27):
you were gonna mock something up and then show it
to me. And the reason we're gonna have that discussion
is because nobody is taking notes, so nobody knows exactly
what the action items are. You made most of the decisions,
you already forgot what five of the follow ups were
that you that you took out of the meeting. So
next Monday you're gonna say, oh, yeah, yeah, sorry, I
forgot about that. I'll get back to you. And you've
(17:48):
got nine people in the room, like, let let the team.
You know, your job as a CEO is to help
the team work as a team and get the team
working together as a team, not to like sit there
and you know, be the quarterback and say you go
run deep, you go run that way, you go run
that way. You're not gonna get anything done, and you're
gonna the company is never gonna move faster. You're the
coaching staff, not the quarterback. Yeah, there's just dozens of
(18:11):
these things that are low leverage, use of time, not
getting the team working together as a team. Everything is
now blockade. CEO took seven of the nine action ISNs.
We're now going to wait for the CEO to make
these decisions. He already forgot what a bunch of them were.
So nothing's gonna get done till next Monday. Couldn't be
a lower leverage meeting. Um, So there's just lots of
stuff that it's not rocket sciences, lots of stuff that
(18:33):
you learn over time to you know, distribute the load.
And CEO should probably be taking almost no decisions out
of a management team meeting like that. Let the team
work together as a team, you know, and then the
one of the I'll say one more thing and then
shut up. Um. One of the things you'll hear is
as a as a come back to that is well,
you know, um, my vice president of engineering and my
(18:55):
general council disagree. So you know, I we had we
had to make a decision, and so I may I
made the decision, you know not. I'll always tell the CEOs. Look,
you're the CEO. You can always you can always override
everyone on the team if you want to and say
you all think we should do that, do X. But
we're gonna do why And here's here's why I think that.
Let's fine, you're the CEO. By the way, only do
(19:17):
that a couple of times a year where you know
you'll lose the team. But you can do that. That's
your prerogative. But most of the time, if you've got
a you know, a couple of few people that disagree
about a decision on your team, you know, have the
VP of engineering and general council like, okay, you two
go away and come back by end of day Wednesday
and propose a solution to the team. And by the way,
(19:37):
don't propose I think we should do this, and she
thinks we should do that. You know, come back with
one proposal. Now you've got your team working together as
a team, and you're not, you know, breaking all the
ties and and you know you're not that you're not
their psychiatrist, and you're not you know, solving the world's problems.
It's gonna be a much more high functioning team over
time as they learn not to work together. We'll be
(20:01):
back with more out of the hustle. After the break,
let's take it to a more macro more market based place.
You know, here we are, UM at a generation defining moment,
you know, with coronavirus, you know, at least for me.
(20:22):
I know you've been through many boom and bus cycles,
I imagine not to this degree, but perhaps you see
that differently. I'm curious, like, how how are you framing
this moment that we're in. Yeah, so as in sort
of in the middle of it. Uh, Yeah, I have
have been through a couple of these, I guess, especially
in business in nine eleven, of course, and then in
(20:45):
the two eight two tho nine recession. I think that, UM,
I guess my experience would tell me a couple of things. One,
it's usually the case that when you're in the middle
love it where, which we certainly are now, it seems
like it's going to all be a lot worse for
(21:08):
a lot longer UM than is usually the case. UM.
The society turns out to usually be pretty resilient about UM,
socio economically, UM, coming back from these things, as horrible
as they are. UM. So my guess is that something
(21:28):
like that will probably happen here, UM, even as bad
as it looks from the inside. And and I think
these things I guess a general way of saying that is,
these things tend to get a lot worse, a lot
more quickly than you think they will, but then also
tend to get better, um, you know, in the macro sense,
(21:48):
more quickly than you think they will. I think that
will something like that will hopefully be the case here
as well. And i'd say the other thing is, when
you're in these things, you have a sense that they will,
you know, and you see certainly see this a lot now.
Things will never be the same, you know, we'll never
think about X the same way again. And it's generally
the case that lots of things go back to exactly
(22:10):
where the way they were, which you wouldn't have thought
would happen. And then some things are very very different.
I mean, obviously, coming out of nine eleven um, going
through airport security has never been the same and never
will be the same. But coming out of the two
thousand eight two thousand nine recession, boy, you wouldn't have
thought if in two thousand nine, if you told people,
you know, people are gonna be flipping houses again in
(22:31):
in three years, they'd look at you like they would
have looked at you like you're crazy. You know, no,
mortgages are gonna be cheap again, and people are gonna
be buying and selling houses. And you know that's what happened.
I think Sequoia's r I P. Good times deck on
investing in that recession. You know, within a within a
few months. Um, some of the best companies ever, you know,
(22:51):
I have been built in the space in the last
couple of decades. We're we're funded Airbnb, in inn Uber
and earlier rounds of you know, the B round sea
rounds of Twitter and Facebook and drop boxing, on and
on and on. And do you think that this is
going to change the type of companies that people are investing?
And I know you have zero to one your fund um,
(23:12):
you know, and and we we know different models of companies.
Some that are geared towards you know, producing as you know,
high of an EBAD are profit as possible. Others that
are spending hundreds of millions, if not billions to acquire markets.
You do you see a major shift occurring? Like what
do you personally you know prioritizing well, for sure, the
growth companies now that burn lots of money to that
(23:34):
need to spend lots and lots of money to grow
are in in just those are they're in you know,
they're in dire straits. UM. So the short answer your
first question is yes, I think the kinds of companies
that people will look to invest in will change, in
in the sense that UM, lots of the remote you know,
remote workforce kinds of software will we'll see increase demand.
(23:57):
Certainly the companies like out school and you know, those
homeschooling technical solutions to education UM and home education seems
like they'll grow significantly. Subscription services that people are starting
to rely on instead of going to the market. Probably
a lot of people will some people will turn out.
Of those, lots of people will just keep them because
they find it like, oh, this is actually a much
(24:19):
more convenient way of getting things. So I think I
do think people will change the kinds of businesses they
invest in, and I think the kinds of the businesses
that are successful coming out of this will be a
little bit different in those kinds of ways. Fascinating. And
I know you've also been involved, um, you know, as
a civic servant. You know, you you've been involved in
the state and in the countries, politics and and and
(24:39):
more more from a business perspective. Are you still active
right now in this moment. Yeah, I'm just trying to
spend most of my time there. But you know, one
of the great things, that's great things that's happening technology
right now. You know, the country likes to for whatever reason,
the country now likes to beat up on the on
the technology class and technology companies. Well, not for whatever reason.
There are lots of perfectly valid reasons. Seemingly these companies
(25:02):
seemingly steam rolling people. So so I get the concern
about these these big tech companies. But behind the scenes,
lots of these tech leaders now are really really rolling
up their sleeves and and and doing what you would
have hoped to have seen from the federal government, like
acquiring masks and and protective gear um gowns, et cetera,
(25:24):
from from all sorts of places overseas manufacturing them. Um.
You know you've been involved in this personally, and uh
and getting those two hospitals and healthcare workers in in
states like Florida and Louisiana and New York and California
and els in Michigan and Illinois that really need them
right now, that's just been great to see and and
(25:45):
a lots of that's happening behind the scenes is not
you know, they're not out there on the front waving
their arms around saying look what I'm doing. Um. I
just think that's great. And you know, it's another it's
it's good to see people you really do see in
these times of crisis, people really reveal themselves to be
you know, you see people for their true selves, and
it's it's cool to see so many people stepping up
(26:07):
and doing that. I'm spending a bunch of my own
time just on trying to help out, um, some local restaurants,
some couple in San Francisco, a couple in New York.
You know that the the entire teams and staffs at
these places have been mostly fload or laid off on
those people don't have other sources of income at all.
(26:28):
And so just been trying to spend spend my own
time and attention there totally. And I really appreciate that. Um.
You know, and I've been reading about both that the
restaurant components, specifically, David Chang had the great article in
New York Times just about how most of your favorite
restaurants are not going to be around, essentially just because
(26:48):
of the way that they're structured. And you know, I've
also been told that, you know, in class A market,
say like you know, the major cities, UM, the major
real estate projects for the most part, hospitality or these
heavily capitalized projects, You're not going to see this like
huge wave of bankruptcy because the banks don't want to
own a thousand hotels. You're gonna have like the more
corporate sized organizations be able to restructure, whereas it is
(27:12):
more more the individually owned, startup, mom and pop it's
going to really take Is this is this the right interpretation?
Do you do? You see things this way? Yeah? I
mean the hospitality industry is just in dire, dire straits.
You know, you never model occupancy rates of subten per
I mean I'm not. It's just like you wouldn't. You
(27:33):
would never what would cause you to model occupancy rates
of subtem percent. So even in your like UM recession planning,
you might think, well, we're going to go from seventy
to occupancy too, you know, sixty or sixty, so we
should really prepare for that rainy, rainy day. Well, they're
(27:53):
subten percent in the entire Las Vegas strip is shut down.
It's crazy. So I just don't know how many of
those companies are gonna be able to how I just
don't know how these things are gonna survive or what
form they're gonna take, um, coming out of this, and
how many of them will go away. Um, it will
(28:13):
surely be the case for the reasons you describe it.
Banks don't want to own all these things, so they'll
provide restructuring capabilities. But it's gonna require it's it's just
the entire landscape of the hospitality space is going to change.
And it makes me think just about like you know,
the it's it's it's really fascinating right now because like
you know that we've been on a course now since say,
(28:35):
you know, two thousand and eleven, two thousand and twelve
to your point, you know, after the the global economic crisis, um,
and and you know, things seem to be pretty set.
We certainly were entering like a hockey stick of the
curve in terms of like company valuations, in terms of
you know, the stock market, it was pretty exponential, just
(28:56):
like the value and return profile like the end of
a cycle anyway. Um, And I don't know, it's just
fascinating to me because, like you know, now, it seems
that all bets are off, Like all you know, outcomes
that seem to be already foretold in terms of who
would succeed or fail and how to measure those things
are are are seemingly out the window. How how are
(29:18):
you like when you're thinking about again, I want to
I sort of ask the question, but I'd love for
you to be a little bit more granular, you know,
like when you're thinking about what you're allocating your time
and your capital into you guys are making typically you know,
significant eight figure, nine figure investments, like when you know
tomorrow Monday arrives, Like, what are you going to be
spending your time on? Who are you going to be
(29:39):
spending your time with? I mean, I think that if
I had to generalize it while while being specific about
answering your question, I think a lesson learned for me
is is a focus on software. Like there are lots
of and and over the last decade there have been
a lot of you could call them chech companies where
the unit economics were really based on software. The Uber, Uber, Airbnb,
(30:03):
you know, you pick, it's there's their technology companies, but
the unit economics are based on rides, but I understand
their software. They're there that the enabling technology is software,
but they're not software companies per se. Right software company
is I write this code once and it is used
by and you know people, and the end plus one
(30:26):
user doesn't cost me anymore because I already have the
code written. You know, software companies, UM, whether they're a
cloud based or consumer based or or or or or
what or what UM. And I think a big, big,
just a big takeaway from me as a reminder to
stay focused and stay in the stand, stay in the
(30:47):
lane of of software unit economics that UM are resilient UM,
or at least can be resilient. The right leadership and
right execution is in place UM to exogenous forces that
inevitably happened like this, whatever they may be, and those
are you know, economics. I understand. And UM that's been
(31:09):
probably the number one takeaway from me, even though lots
of the really really big companies in the last decade
have have not necessarily been those as we just discussed. Sure,
I find it all really informative and appreciate you, you know,
breaking it down, UM. And I mean it seems though
you know, there's there's gonna be an acceleration in the
(31:30):
human cost to you know, this this new era of
software and AI and robotics and automation, and you know,
again we were already hitting a curve where, like you said,
all these things are more at risk. Now we're going
to perhaps you know, order these things from home or
you know, do our workouts on on zoom versus at
(31:51):
the gym. Um, you know what I mean, Like there's
all there's all these implications that happened after and often
the things that you're talking about empowering, Um, you know
do have a human cost. Now in history, there's always
been you know, the this sort of cognitive enabling you know,
power of technology where there are all the new jobs
that would come out of these things that were being created.
(32:13):
I'm just curious how you think about that because I
know you, you know, you're a very for purpose guy.
You have a huge heart. Um, you you care a
lot about you know. The motivator for you is that
you know these things. It's not you know that software
builds businesses, that creates more exits. So it's like your's
you know, a couple of zeros in a bank account. Like,
that's not the motivator for you. So I'm curious, like,
(32:34):
you know, when you think about this and the implications,
where does your head go. I'm not a believer in
the as as as I mentioned a little bit earlier
or alluded to at least, I'm not a big believer
in everything has changed forever. Just because the history of
these history of of you know, black Swan events, whatever
you wanna call them. Um, this could never happen, and
(32:56):
then it happens, Um, is that a lot of things
do go back to the way they were because society
is resilient. So you know, for example, I'm sure Coachella
one will be packed. I just I just think it
will be. UM. And the notion that well, no one's
gonna go to you know, people are gonna think twice
(33:16):
before they go to you know, uh uh Los Angeles
Lakers game again, Like no, they won't, I mean not,
not not a year from now. They'll total totally gonna
go to a Lakers game, Okay, and you know, and yeah,
our people are gonna be more careful about that, coming
immediately out of this and and going back to work
and making sure they're um going back to work in
a safe way in in you know, in in in
(33:38):
in September or whatever month it is, um this year,
of course, but but by this time next year, people
will be going to sporting events again, and and and
you know, and playing flag football on the field and
the and the and and going to concerts. UM. I
just I just think that's the case. I do. I
do think that that the um historic belief that you know, UM,
(34:03):
there's kind of been this UM, I don't know, dogma
maybe that well, UM, you know, you can't really work
from home for too long, and you can't really build
a remote workforce because it doesn't really work. Everyone's got
to be in the officeite, on the same page and
in the same physical location. A lot of that I
think has has been sort of you know, we've now
run the experiment and are seeing actually you can do
(34:24):
a pretty good job with a bunch of your people. UM,
you know remote. UM. There's some business that or businesses
that are growing like a weed during this time, and
and that's with all remote employees. UM. So it's certainly
the case that some of the employees can be remote
and we can be just as just as effective going forward. UM.
And then I think another set of institutions that will
(34:48):
probably be disrupted and hopefully create even more jobs, are
you know, uh schools and universities there. You know a
lot of parents right now going wait a minute, I
was paying you know, extraordinary amount of money and having
to borrow money to to pay tuition, and my son
(35:08):
daughter is doing you know, two or three hours a
day remotely on zoom right now. They could go do
that with you know, one of these online universities UM
for one price. So I think, I think, I think
there will be some dramatic changes just based on we've
now run the experiment of could you do a bunch
of this stuff remotely and are seeing that it is possible.
(35:31):
You know, I'm sure there's some CFOs out there they're going,
wait a minute. We were spending two hundred fifty thousand
a month on travel and entertainment, and you know, we've
seen some impact to the next quarter, but not impact
to the next quarter. And now we're not spending any
money on travel entertainment. Is all that travel entertainment, you know,
has that all been really worth it? We now get
(35:51):
to find out, um, and I think some of that
will change. Interesting. Yeah, I think you're right on the
on the human component to the coach Hellas or the
Lakers games. In fact, we might need it more. Yeah, yeah,
that's that's right. Um. I'm a much bigger believer in
there will be more desire for a connection and the
realization that, wow, what have I been doing not you know,
(36:13):
going out and seeing my friends for dinner on Tuesday
night when I could have been doing that, And and
travel and seeing seeing people in places you don't think
about going to see that you'd like to see. I
think there will be, you know again, once it's safe,
there will be even more of that than there was previously.
Art of the hustle will be right back after this
(36:34):
short break. I want to ask you, you know, just
as we're sitting here and talking and I'm thinking about, man, like,
how lucky am I that I just get to pepper
you with questions now that we've created this format. But
you know, I want to talk to you about Twitter. Um.
(36:55):
You know, it's something that you uniquely have gotten to
think about more than just about anyone else on the planet.
And I, you know, I frankly still it's it's still
such an enigma to me. It's so big it's so impactful.
What and it's still and it's still ever evolving and changing.
It's I think a misunderstood you know platform. What did
it do for us? How did Twitter change the world? Well,
(37:17):
it did several things. It enabled the world to see
exactly what was happening in some location from the inside
out immediately. What do I mean by that? By inside out,
I mean you get to see through Twitter what's happening
in the world from the people that are in it,
(37:39):
not from outside observers of it like a reporter or
you know, or here's a video camera of what's happening
inside the stadium. You're getting to hear from the players
in the stadium. You're getting to hear from the people
participating in the event, whatever the event is. You're from
the you know, from the people on the plane that
(38:00):
crashed at you know, at at SFO on the flight
back from from Seoul, you know, who are tweeting just
crash landed at SFO. UM. That inside out view of
what's happening from the participants in an unfiltered way instead
of filtered through some third party commenting on it has
(38:20):
been I think overall awesome. It comes along with lots
of you know, UM challenges like people's using it, people
and state actors UM. And that is just in case
for anyone out there who still doesn't believe that for
whatever reason, it has been the case in the past
(38:41):
that state actors and currently use these platforms to try
to spread misinformation UM and discord UM. But I think
overall it's been great. You know, you get to see
the three sixty degree view of a person instead of
just the reporting of of narrative of of of of
(39:01):
a person or an event or a or a a group.
That's a great perspective on it. And and uh, you know,
Jack's particularly amazes me. You know, I see him as
like a once in a generation entrepreneur um. You know
the at the top of the interview I alluded to,
(39:22):
you know, baking bread and vipasana, which is you know,
his real life UM. And you know, the guy is
running both Square and Twitter. I'm gonna interrupt you to
tell you something about Jack that people don't realize just
because look, I'm not speaking out of school. Jack would
tell you he's an introvert by nature, you know, he
he is not UM. He's sort of like if you know,
(39:44):
if you told me, like, hey want you to get
up on stage, and you know, uh, improvised with this
group of people, I do it. And if you told
that to Jack, you know, he'd probably have a heart attack.
I mean, he's just an introvert by nature, but he's like,
he's really really funny. He's got this great into humor.
So you know, when I was running Twitter, Um, I
want to see you on Twitter, and he was chairman
(40:05):
of the board, we would have dinner every Tuesday night, um,
every week, uh and talk about the company and and
it just what was going on in our lives. And
he's he's extraordinarily funny. So um. So hopefully, as you know,
hopefully as he gets more comfortable speaking, speaking in in
front of a large crowd, so people will get to
see more and more and more of that. When I
imagine there's only so much you can say in the
(40:27):
present moment as a CEO of a publicly trade organization,
and for you, like, I mean, is it is that?
I guess I'm just trying to you know, if I
can pull out from your perspective, what makes exceptional leadership,
what builds exceptional companies? What is like the zero to
one for us all out here that are like, you know,
(40:48):
on the path because you you just you've lived it,
you've studied it, you've invested in every phase of businesses,
you've built, you know, different generations of technology, you've worked with,
you know the best of my generation. Um, you know,
like help help us arrive at some of the patterns
that you've recognized. Great leaders eat last, you know, they
(41:09):
they make sure the team has taken care of first.
They're high empathy. They're able to look at things through
other people's point of view, and they listen, and they
know that their job isn't to prevent mistakes from happening.
Their job is to correct mistakes quickly when they happen.
They admit their mistakes, and they make it easy for
(41:30):
people to tell them the truth. The faster you know
the truth, the sooner you can correct mistakes that have
been happened. How do you wrap that all into a bundle.
They're they're high empathy people. There are people who are
able to realize that everyone else in the world is
a me as well, um, And that's what makes a
great leader. Now are there exceptions to that? Of course,
there are some people that are once in a millennium
(41:53):
geniuses that are able to do things differently, but generally speaking,
I think those are the characteristics of a great leader. Well, Dick,
I appreciate it, man Um any other questions for me,
This has been awesome. I really appreciate you coming on
the podcast. I really appreciate your mentorship. I will say that,
like you know, UM, a lot of people celebrating the
(42:15):
end zones with you. A lot of people can be
really great friends. But when it comes to truly being
able to help strategize for things that other people haven't
seen before, you know that the hardest issues that you
know end up perplexing you as you scale in business.
You've been one of my you know, very you know,
most trusted advisors. Um, you know, somebody have always known
(42:36):
I could turn to when you know things are stickier
where they're above my pay grade or over my head.
And um, you've done it without the expectation of return.
It's clear, like you know, and and I just you know,
I think that that's the way that you lead by
example that I learned from. You know. I always remember
like Dean Smith, the former you know, the gold University
of North Carolina basketball coach, thing you know, like teaching
(42:57):
his basketball players, like the basics of do good things,
good things will happen. You know, you pass the ball
the right way and think about executing the right way
good things, the results will be generally speaking, with some outliers,
the results will be great. And I just kind of
feel like, you know, that's a good way to think
about living your life. Do good things for people, and
good things will happen. You don't have to like, everything
doesn't have to be a you know, what are you
(43:18):
gonna do for me? It's just a silly and I
just think that's a it's a scarcity mentality instead of
instead of an abundance mentality. So I'm more than happy
to do it and always will be. So the score
takes care of itself. Yeah, that's yes, that's right. Thank
you for continuing the sports metaphor with the with the
Bill Walsh comment My pleasure, My pleasure. Well, thanks again, Dick.
(43:39):
I really appreciate you being on and keep rocking out there.
All right, Thanks buddy, We'll see you. For more podcasts
(44:03):
from my Heart Radio, visit the I Heart Radio app,
Apple podcast, or wherever you listen to your favorite shows.
Art of the Hustle is a production of I Heart Radio.
You're listening to the Art of the Hustle, the show
that breaks down has some of the world's most fascinating
people have hustled, strategized, and learned their way into achieving
(00:22):
great things. I'm your host, Jeff Rosenthal, co founder of Summit,
and in today's episode, I'm excited to chat with a
mentor and advisor of mine and a straight living legend,
Dick Costello. Dick is an entrepreneur and investor, advisor to
governor's presidents, CEOs, and an HBO show or two. He's
the former CEO of Twitter and currently invests out of
(00:43):
his fund zero one Advisors. Welcome to the Art of
the Hustle, Dick, Thanks for being on the show. Happy
to be on the show. So, uh, we were just
talking briefly before we pressed record, and you were telling
me that you guys had a full vegetable garden. Um,
where are you in the world right now? We're in
We're in Napa. We have a little tiny property in
(01:06):
the middle of all the vines. We don't have we
don't have any grapevines, but we just have a place
in the Valley and Nappa So it's kind of you know,
it's just farmers out here. Now. There's nobody up here
because the wineries are all close, so it's it's just
farmers who are dealing with their grape vines. And then
we have a big vegetable garden, so that's coming and
really coming in handy. Yeah, it is. The real luxuries
(01:28):
in life are emerging. You know, I think that we
were taking a lot of these things for granted because
of like the unbebelievable amount of options we have for
all of like you know, life's the exotic things that
become the day to day and necessities. Yeah. No, we've
got a ton of you know, we've got a ton
of like kale and collared greens and art of chokes,
(01:50):
and I mean you usually think like, oh, we've got
way too much kale or way too many art chokes,
and you know, you give a bunch of away now
it's great, Um, just go out to the garden and
get it. It's really awesome to have something like that.
It's sort of it's really a luxury. This thing that
goes from like you just said, this thing that goes
from Oh it's cute two. Oh. It's a total luxury
(02:14):
to be able to have that right now. It's awesome.
It's such a stereotype of like Silicon Valley swashbuckling CEO
goes to you know, garden kale or chop wood or
baked bread. But it's real. What do you think that? Why?
Why do you think that? That's a common practice where
you'll see a lot of the thought leaders in your
(02:34):
space that have this total like left brain right brain
switch um into you know, remote vipas in the style hangs.
I'm not doing any silent meditation retreats or sweat lodges. Okay,
I don't know. I'm just always like I can't. I
have to be busy, you know. I just have always
(02:55):
been that way. I had a I had when I
was in sixth grade. I got my first job. Um
you know, since I was in sixth grade, one of
the only things I could do was go be a
golf caddy and a country club because you know, I
couldn't get a eleven years old twelve years old can't
get a regular job. And uh, you know I was
up at like five am on Saturday and Sunday morning,
so I could get there early. So I could get
(03:16):
out twice and make more money. I just so you
were eleven years old. This is Royal Oak, Michigan, that's correct. Amazing. Uh.
And I know you went to University of Michigan and
you've been you know, in the game in terms of
technology and Silicon Valley and you know a lot of
these generational companies Google and Twitter, etcetera for a long
(03:37):
long time. But it sounds like, you know, at eleven,
you already had the hustle. You already were you know,
motivated itself motivated. But why why did you want to
run two routes? Uh? And that fashion? What did you
want the money for? What was the what was the motivator?
I don't even remember. I just was like, I gotta
get there before anyone else gets there, so I can
get two rounds in so I can make you know,
(03:59):
you know, forty buck instead of just making twenty bucks.
Because if I only get out once, I'll make twenty bucks.
And i'll make get out twice, I'll make forty bucks. Um.
And I just saved it all, you know, I didn't
spend it on stuff. I just saved it all for college,
you know. And I was able to even though I
did that for like three years, I think it paid
for like, you know, a semester or something at University
of Michigan. Um So, the hustle to return back in
(04:23):
those days, for even back then, for higher education in
state higher education at a public school. No less, I
still wasn't still wasn't too terrific. But it's like had
this like, um, you know, I just always wanted to
be moving, you know, um just from way back in
the day. And then my dad got me one of
the very first personal computers, this Radio Shack TRS Model eighty,
(04:47):
and I just started learning a program on that. So
even when I went to school to even when I
went to Michigan, I already knew I wanted to study
computer science. I kind of knew what I was gonna do.
And was it already? I know, I know today it's
a pretty legendary engineering computer Your science school was it
then in the eighties? Um So. The funny thing was
in the eighties the computer science department was in the
(05:07):
Humanities school, the literature science there it's called l S
and a literature science and the arts liberal Arts school.
It wasn't it wasn't in UM in the engineering school
the way it is today. So the crazy thing that
happened was because I was in the literature liberal arts school,
I had to have a certain number of humanities credits
when I graduated, and uh and that meant senior year,
(05:32):
I took a bunch of like theater classes because I
was like, I need some stupid arts credits to graduate
and uh and I got the bug from doing that,
And so when I graduated, it's sort of a bunch
of told the story a few times. But when I graduated,
I turned down all myine like programming jobs at companies
like you know, I don't know, Burrows and Honeywell and
(05:54):
those kinds of places, um and and went to Second
City in Chicago to try to um just become month
improviser and get on Saturday night life. So ditched everything
and went to Chicago and did improv comedy for years.
And uh and you told you know we were hanging
a few months ago and that it was the first
time I had heard this. But if Steve Carrell was
(06:14):
in your Second City class, correct, He and I showed
up almost the exact same time there, and we're in
one of the first they launched this thing when we've
gotten there, called the Second City Training Center. It was
basically like, hey, if you want to, you know, perform
a Second City like everybody else who comes to Chicago,
and uh, you know, then you got to go through
this program first. And he and I were in the
(06:35):
second group, I think, in the program, and we sort
of showed up there the same day, um with a
bunch of other you know, a bunch of other people
were all there at the same time. Um, you know
over the years, uh, Tina Fey of course, Adam McKay, um,
Horatio sans Um, Gosh, Rachel Dratch and you know, Matt Walsh,
all the UCB people were there at the same time.
(06:56):
So it's really cool, fun time to be there. And
do you see, like what are the overlaps. I'm sure
you've thought about this, but in terms of like leadership
skills and improv comedy and how do these things in
your mind connect, oh man, like tons um. First of all,
in improv comedy, I mean first, the very first thing,
(07:17):
you know sort of you figure out if you if
you and if you don't, you don't last very long.
Is listening is the most important thing to be doing
on stage because there's not there are no objects on stage.
You're just making it all up as you go along,
and and watching what the other people and are doing
and listening to what they're saying as they make it up.
And if you don't listen, you know, the scene doesn't
(07:37):
really go anywhere. So kind of beat into you early
on listening. Listening. Listening is the most important thing you
can do to help propel a scene forward. And that's
the you know, I used to tell my managers at Twitter,
listening is like sevent of what managers should be doing.
You know, your job isn't to make all the decisions
(07:57):
or be omniscient. Your job is to other feedback and
get the best information and make sure the best decisions
are being made, not to be omniscient and make all
the decisions and tell people what to do. So I
mean there were tongues of overlap there and then and
then secondly, I mean even even sort of created this
sort of you know, I just one of the beautiful
(08:18):
things in improvisation is this notion of yes, and where
everything that someone initiates you just accept it as fact
and accepted is the truth. Whenever they initiate something on
stage and the idea of yes and was, I accept
that that's now the truth of what's happening in this scene,
and on and on top of that, here's something I'm
gonna add to that. And it's instead of saying you know, no,
(08:40):
that's not true, which stops the scene, or asking a
question which doesn't propel a scene forward, we're saying yes,
but which directs a scene in another direction. The idea
of yes and was, I'm just gonna accept what you
said is the truth, and and we're gonna go forward.
And so we sort of got to this point at
Twitter where I realized people were not taking risks or
(09:03):
not taking chances because they were, um, you know, they
don't want to get in trouble or they're afraid of
breaking something, so they'll instead of initiating something, they'll go
ask for permission. This happens at all, by the way,
not just Twitter. As an organization grows and gets over
some you know, some some number over the dunbar number
of number of people you can know in a company. Um,
(09:25):
folks will start to go around and ask for permission
to be able to do things, and people won't say no.
They'll generally say you should go ask these four people,
and you know, pretty soon it's three weeks later and
nothing's been done because the person is checking off, you know,
everybody on the checklist of permission they have to get.
So at Twitter just instituted this bias to yes and
bias to yes was assume the answer is yes. You're
(09:47):
not allowed to You're not allowed to tell people they
have to go ask other people for permission. You know,
if if M, if someone you're directly reporting to doesn't
tell you, you're not allowed to do something, you know,
no one else's no one else is allowed to tell
You've got to go people for permission. Assume the answer
is yes, communicate what you're gonna do and do it.
UM and that is that sort of stuff was all
based on improvisation and was enormously helpful. And you've told
(10:11):
me you've shared some advice with me in the past
that you've told me is also pretty widely applicable. That
you had mentioned in UH in that which was you
know that a lot of you know, talented people UM
that run organizations do get stuck in this self limiting
you know, I'm doing everything or involved in every decision
or directing, you know, vision on all these different departments,
(10:32):
whether you are like the idea of stopping making all
the decisions? How common is this? How often when you're
you know, working with your portfolio companies, where you are,
you are you sharing this advice and help help us
understand a little bit better. Always I mean to tell
people like, don't you know? First of all, when leaders
tell people what to do, you know, it removes all
(10:54):
the ownership from the person's sense of you know, say
you tell your you know, I don't know, you're so
your your manager and you and you tell someone what
to do instead of letting them find the solution or
helping them find the solution that that they've come up with,
they don't feel accountability to it. They don't feel ownership
of it because you you know, if it doesn't work,
they're like, well, you know, Dick's crazy and he had
(11:17):
this stupid idea. I guess I'll go see what he
wants to do next, instead of if it's their idea
and they come up with it and they feel real
ownership of the solution and it doesn't work, they're gonna
figure it out. But you know, I got to figure
out how what to do about this? Because this was
my idea. So trying to hold people accountable for something
when you're the one telling them what to do is
just creates misery. Um, and it's not particularly a high
(11:38):
leverage juice of of you know, anybody's time. I remember
Bill Campbell, you know, the famous sort of executive coach
um who was on the Apple board and was famously
Larry and Seragey and Eric's coach um. You know when
I was when I was first CEO at Twitter. He
sat in the back of the room in a management
team meeting and I thought it was a particularly good
(11:59):
meeting because it made all these decisions and uh we
left the room and I thought, I was like, you know,
what do you think? You know, I'm pretty psyched about myself.
He was like, that was a d you know what
are you talking about. It's like, he said, let me
tell you something. When I took over a CEO of Claris,
they spun out Clara Software out of Apple. It's like
making all these decisions because now I'm the CEO and
I should make all these decisions. And this woman who
(12:21):
was one of my senior vice presidents who would come
from Apple with me, named Donna Davinski came up to
me after the second week and said, Hey, Bill, if
you're gonna make all the decisions, I'm just gonna go
back to Apple and you can pay someone a lot
less money to do this job. And sort of like
hit him on the head that you know, he's got
all these smart people in the company. Let them own
their solutions, and and you know the CEO should really
only be making the decisions that only the CEO can make. Um.
(12:44):
I think that's true, and I tell people that all
the time, Like, while we've got all these really smart
people around the table, if you're making all the decisions, man,
it's such a I think give When you're a young entrepreneur,
you want to like hit the game winner, you know,
you want to like be the player, get the celebration
and retire the jersey. And then as you get older,
you're like, man, what a limiting factor if like I
(13:04):
have to be the one and then you you know,
I I remember, you know, and I'm not you know,
particularly great manager or business builder. I think, um, you know,
I'm very much empowered by a community of people around me,
Like I have a very flat wide, you know, incredibly
talented team that helps us have such like, you know,
sort of a wide breath at summit. Um. But when
when I you know, I recall sucking at work for frankly,
(13:27):
like six eight months. It was around the time of
having my first kid. I was like, man, I just
have to change the way I do things, Like if
I just hustle or my working harder or more involved
in all these things, like, it's not gonna you know,
it's just only going to forever incrementally change the outcome. Um.
So I just remember having to actually stop and pause
(13:48):
and and you know, work differently. Um. And I've asked,
you know, other people on the podcast about that. They're like, yeah, dude,
that's just called getting older and getting smarter. I wonder
how you think about that transition. Yeah, I think, well, so,
first of all, you know, there's a reason that younger
entrepreneurs do that. It's because when they started the company
and there are eight people around, you know, and and
(14:10):
now there's five people because they've been successful and they
scaled the the action was reinforced. Hey, uh, two years
ago when I dive bombed that product meeting and said no, no, no,
that's stupid, let's do it this way and wrote the
new thing on the white board. Look, it worked. So
you know the reason they got to a successful company
that's now growing is because when there were ten of them,
(14:33):
they did this a lot, and you know, it works,
so I should keep doing it. You know, you just
have to learn as you migrate from building a product
to building a company, building and scaling a company. UM
to let people feel real ownership over decisions, and ownership
is accountability with authority, Like I have the authority to
figure out what I want the solution to be, and
(14:55):
then I'll I'll feel a lot more accountable to it.
If you tell me what to do and then get
mad at me because it did work, I'm not gonna
feel very bad about it. And you know I'm not
probably you know, probably gonna sit there and well, let's
just wait to see what Dick tells me to do next.
It's not a very it's not a very scalable or
high leverage solution. UM. So I always looked for I
always try to help CEOs with you know, just always
(15:18):
be thinking about operating leverage and operating efficiency and how
can you get more what's the highest leverage thing you
can be doing right now? And what's a higher leverage
rate way to run that meeting? Those kinds of things,
will you expand upon that the highest leverage way to
run a meeting? Yeah, Like so for example, sit in.
One of the things I'll do is you know, when
I'm just getting involved in a company, and I'll just
(15:39):
ask to like, let me just sit in the back
of the room and a management team meeting and take notes.
You know. And again these are companies that are remember
they were like all businesses, they are small. They sit
around a table, they try to figure out what to do,
They check in with each other and grows and grows
and grows, and um, you know there's now there's a
hundred fifty people and you know, get to sit in
the management Monday. And I mean, I'll give you, uh
(16:02):
an example from a couple of years ago, sitting in
the back of the room. There's nine people in the meeting.
No one's taken notes. It's an hour and a half
two hour meeting. We're going around the room, people are
doing status updates. And I'm already right downline a notes
Like there's four people in this company. Now, like, why
are we spending the most expense? One of the most
expensive meetings in the company with the entire leadership team
just doing status updates. We could have done this in
(16:24):
a Sunday night email. Um, we should be talking about
you know, contentious decisions that we need to make where
everyone's not on the same page yet, or the strategic
landscape or the competitive landscape, or a deal we lost. Anyway,
and we leave the meeting and you know, much like
me and much like me walking off with Bill Campbell
after several years ago, I walk up the CEO and CEE,
(16:45):
I was like, what do you think? Pretty good? Hut?
And I said, how many action items came out of
the meeting? And the CEO sessing, like, uh five? You
know that guy took that one? Um, a VP marketing,
she took that one, and I took two like and
so I said, well, fortunately I took notes. No one
else took notes, but I took notes. There were nine
action items that came out of the meeting. We already
(17:06):
know that you forgot what five of them are. So
next Monday's meeting is gonna be you know, and just
you know, creates misery for people, right like next I said,
next Monday, And next Monday's meeting, you're gonna have a
conversation something along the lines of, hey, where's that metrics
dashboard we talked about last week? And someone will say,
weren't you gonna get me the requirements for it first? No,
(17:27):
you were gonna mock something up and then show it
to me. And the reason we're gonna have that discussion
is because nobody is taking notes, so nobody knows exactly
what the action items are. You made most of the decisions,
you already forgot what five of the follow ups were
that you that you took out of the meeting. So
next Monday you're gonna say, oh, yeah, yeah, sorry, I
forgot about that. I'll get back to you. And you've
(17:48):
got nine people in the room, like, let let the team.
You know, your job as a CEO is to help
the team work as a team and get the team
working together as a team, not to like sit there
and you know, be the quarterback and say you go
run deep, you go run that way, you go run
that way. You're not gonna get anything done, and you're
gonna the company is never gonna move faster. You're the
coaching staff, not the quarterback. Yeah, there's just dozens of
(18:11):
these things that are low leverage, use of time, not
getting the team working together as a team. Everything is
now blockade. CEO took seven of the nine action ISNs.
We're now going to wait for the CEO to make
these decisions. He already forgot what a bunch of them were.
So nothing's gonna get done till next Monday. Couldn't be
a lower leverage meeting. Um, So there's just lots of
stuff that it's not rocket sciences, lots of stuff that
(18:33):
you learn over time to you know, distribute the load.
And CEO should probably be taking almost no decisions out
of a management team meeting like that. Let the team
work together as a team, you know, and then the
one of the I'll say one more thing and then
shut up. Um. One of the things you'll hear is
as a as a come back to that is well,
you know, um, my vice president of engineering and my
(18:55):
general council disagree. So you know, I we had we
had to make a decision, and so I may I
made the decision, you know not. I'll always tell the CEOs. Look,
you're the CEO. You can always you can always override
everyone on the team if you want to and say
you all think we should do that, do X. But
we're gonna do why And here's here's why I think that.
Let's fine, you're the CEO. By the way, only do
(19:17):
that a couple of times a year where you know
you'll lose the team. But you can do that. That's
your prerogative. But most of the time, if you've got
a you know, a couple of few people that disagree
about a decision on your team, you know, have the
VP of engineering and general council like, okay, you two
go away and come back by end of day Wednesday
and propose a solution to the team. And by the way,
(19:37):
don't propose I think we should do this, and she
thinks we should do that. You know, come back with
one proposal. Now you've got your team working together as
a team, and you're not, you know, breaking all the
ties and and you know you're not that you're not
their psychiatrist, and you're not you know, solving the world's problems.
It's gonna be a much more high functioning team over
time as they learn not to work together. We'll be
(20:01):
back with more out of the hustle. After the break,
let's take it to a more macro more market based place.
You know, here we are, UM at a generation defining moment,
you know, with coronavirus, you know, at least for me.
(20:22):
I know you've been through many boom and bus cycles,
I imagine not to this degree, but perhaps you see
that differently. I'm curious, like, how how are you framing
this moment that we're in. Yeah, so as in sort
of in the middle of it. Uh, Yeah, I have
have been through a couple of these, I guess, especially
in business in nine eleven, of course, and then in
(20:45):
the two eight two tho nine recession. I think that, UM,
I guess my experience would tell me a couple of things. One,
it's usually the case that when you're in the middle
love it where, which we certainly are now, it seems
like it's going to all be a lot worse for
(21:08):
a lot longer UM than is usually the case. UM.
The society turns out to usually be pretty resilient about UM,
socio economically, UM, coming back from these things, as horrible
as they are. UM. So my guess is that something
(21:28):
like that will probably happen here, UM, even as bad
as it looks from the inside. And and I think
these things I guess a general way of saying that is,
these things tend to get a lot worse, a lot
more quickly than you think they will, but then also
tend to get better, um, you know, in the macro sense,
(21:48):
more quickly than you think they will. I think that
will something like that will hopefully be the case here
as well. And i'd say the other thing is, when
you're in these things, you have a sense that they will,
you know, and you see certainly see this a lot now.
Things will never be the same, you know, we'll never
think about X the same way again. And it's generally
the case that lots of things go back to exactly
(22:10):
where the way they were, which you wouldn't have thought
would happen. And then some things are very very different.
I mean, obviously, coming out of nine eleven um, going
through airport security has never been the same and never
will be the same. But coming out of the two
thousand eight two thousand nine recession, boy, you wouldn't have
thought if in two thousand nine, if you told people,
you know, people are gonna be flipping houses again in
(22:31):
in three years, they'd look at you like they would
have looked at you like you're crazy. You know, no,
mortgages are gonna be cheap again, and people are gonna
be buying and selling houses. And you know that's what happened.
I think Sequoia's r I P. Good times deck on
investing in that recession. You know, within a within a
few months. Um, some of the best companies ever, you know,
(22:51):
I have been built in the space in the last
couple of decades. We're we're funded Airbnb, in inn Uber
and earlier rounds of you know, the B round sea
rounds of Twitter and Facebook and drop boxing, on and
on and on. And do you think that this is
going to change the type of companies that people are investing?
And I know you have zero to one your fund um,
(23:12):
you know, and and we we know different models of companies.
Some that are geared towards you know, producing as you know,
high of an EBAD are profit as possible. Others that
are spending hundreds of millions, if not billions to acquire markets.
You do you see a major shift occurring? Like what
do you personally you know prioritizing well, for sure, the
growth companies now that burn lots of money to that
(23:34):
need to spend lots and lots of money to grow
are in in just those are they're in you know,
they're in dire straits. UM. So the short answer your
first question is yes, I think the kinds of companies
that people will look to invest in will change, in
in the sense that UM, lots of the remote you know,
remote workforce kinds of software will we'll see increase demand.
(23:57):
Certainly the companies like out school and you know, those
homeschooling technical solutions to education UM and home education seems
like they'll grow significantly. Subscription services that people are starting
to rely on instead of going to the market. Probably
a lot of people will some people will turn out.
Of those, lots of people will just keep them because
they find it like, oh, this is actually a much
(24:19):
more convenient way of getting things. So I think I
do think people will change the kinds of businesses they
invest in, and I think the kinds of the businesses
that are successful coming out of this will be a
little bit different in those kinds of ways. Fascinating. And
I know you've also been involved, um, you know, as
a civic servant. You know, you you've been involved in
the state and in the countries, politics and and and
(24:39):
more more from a business perspective. Are you still active
right now in this moment. Yeah, I'm just trying to
spend most of my time there. But you know, one
of the great things, that's great things that's happening technology
right now. You know, the country likes to for whatever reason,
the country now likes to beat up on the on
the technology class and technology companies. Well, not for whatever reason.
There are lots of perfectly valid reasons. Seemingly these companies
(25:02):
seemingly steam rolling people. So so I get the concern
about these these big tech companies. But behind the scenes,
lots of these tech leaders now are really really rolling
up their sleeves and and and doing what you would
have hoped to have seen from the federal government, like
acquiring masks and and protective gear um gowns, et cetera,
(25:24):
from from all sorts of places overseas manufacturing them. Um.
You know you've been involved in this personally, and uh
and getting those two hospitals and healthcare workers in in
states like Florida and Louisiana and New York and California
and els in Michigan and Illinois that really need them
right now, that's just been great to see and and
(25:45):
a lots of that's happening behind the scenes is not
you know, they're not out there on the front waving
their arms around saying look what I'm doing. Um. I
just think that's great. And you know, it's another it's
it's good to see people you really do see in
these times of crisis, people really reveal themselves to be
you know, you see people for their true selves, and
it's it's cool to see so many people stepping up
(26:07):
and doing that. I'm spending a bunch of my own
time just on trying to help out, um, some local restaurants,
some couple in San Francisco, a couple in New York.
You know that the the entire teams and staffs at
these places have been mostly fload or laid off on
those people don't have other sources of income at all.
(26:28):
And so just been trying to spend spend my own
time and attention there totally. And I really appreciate that. Um.
You know, and I've been reading about both that the
restaurant components, specifically, David Chang had the great article in
New York Times just about how most of your favorite
restaurants are not going to be around, essentially just because
(26:48):
of the way that they're structured. And you know, I've
also been told that, you know, in class A market,
say like you know, the major cities, UM, the major
real estate projects for the most part, hospitality or these
heavily capitalized projects, You're not going to see this like
huge wave of bankruptcy because the banks don't want to
own a thousand hotels. You're gonna have like the more
corporate sized organizations be able to restructure, whereas it is
(27:12):
more more the individually owned, startup, mom and pop it's
going to really take Is this is this the right interpretation?
Do you do? You see things this way? Yeah? I
mean the hospitality industry is just in dire, dire straits.
You know, you never model occupancy rates of subten per
I mean I'm not. It's just like you wouldn't. You
(27:33):
would never what would cause you to model occupancy rates
of subtem percent. So even in your like UM recession planning,
you might think, well, we're going to go from seventy
to occupancy too, you know, sixty or sixty, so we
should really prepare for that rainy, rainy day. Well, they're
(27:53):
subten percent in the entire Las Vegas strip is shut down.
It's crazy. So I just don't know how many of
those companies are gonna be able to how I just
don't know how these things are gonna survive or what
form they're gonna take, um, coming out of this, and
how many of them will go away. Um, it will
(28:13):
surely be the case for the reasons you describe it.
Banks don't want to own all these things, so they'll
provide restructuring capabilities. But it's gonna require it's it's just
the entire landscape of the hospitality space is going to change.
And it makes me think just about like you know,
the it's it's it's really fascinating right now because like
you know that we've been on a course now since say,
(28:35):
you know, two thousand and eleven, two thousand and twelve
to your point, you know, after the the global economic crisis, um,
and and you know, things seem to be pretty set.
We certainly were entering like a hockey stick of the
curve in terms of like company valuations, in terms of
you know, the stock market, it was pretty exponential, just
(28:56):
like the value and return profile like the end of
a cycle anyway. Um, And I don't know, it's just
fascinating to me because, like you know, now, it seems
that all bets are off, Like all you know, outcomes
that seem to be already foretold in terms of who
would succeed or fail and how to measure those things
are are are seemingly out the window. How how are
(29:18):
you like when you're thinking about again, I want to
I sort of ask the question, but I'd love for
you to be a little bit more granular, you know,
like when you're thinking about what you're allocating your time
and your capital into you guys are making typically you know,
significant eight figure, nine figure investments, like when you know
tomorrow Monday arrives, Like, what are you going to be
spending your time on? Who are you going to be
(29:39):
spending your time with? I mean, I think that if
I had to generalize it while while being specific about
answering your question, I think a lesson learned for me
is is a focus on software. Like there are lots
of and and over the last decade there have been
a lot of you could call them chech companies where
the unit economics were really based on software. The Uber, Uber, Airbnb,
(30:03):
you know, you pick, it's there's their technology companies, but
the unit economics are based on rides, but I understand
their software. They're there that the enabling technology is software,
but they're not software companies per se. Right software company
is I write this code once and it is used
by and you know people, and the end plus one
(30:26):
user doesn't cost me anymore because I already have the
code written. You know, software companies, UM, whether they're a
cloud based or consumer based or or or or or
what or what UM. And I think a big, big,
just a big takeaway from me as a reminder to
stay focused and stay in the stand, stay in the
(30:47):
lane of of software unit economics that UM are resilient UM,
or at least can be resilient. The right leadership and
right execution is in place UM to exogenous forces that
inevitably happened like this, whatever they may be, and those
are you know, economics. I understand. And UM that's been
(31:09):
probably the number one takeaway from me, even though lots
of the really really big companies in the last decade
have have not necessarily been those as we just discussed. Sure,
I find it all really informative and appreciate you, you know,
breaking it down, UM. And I mean it seems though
you know, there's there's gonna be an acceleration in the
(31:30):
human cost to you know, this this new era of
software and AI and robotics and automation, and you know,
again we were already hitting a curve where, like you said,
all these things are more at risk. Now we're going
to perhaps you know, order these things from home or
you know, do our workouts on on zoom versus at
(31:51):
the gym. Um, you know what I mean, Like there's
all there's all these implications that happened after and often
the things that you're talking about empowering, Um, you know
do have a human cost. Now in history, there's always
been you know, the this sort of cognitive enabling you know,
power of technology where there are all the new jobs
that would come out of these things that were being created.
(32:13):
I'm just curious how you think about that because I
know you, you know, you're a very for purpose guy.
You have a huge heart. Um, you you care a
lot about you know. The motivator for you is that
you know these things. It's not you know that software
builds businesses, that creates more exits. So it's like your's
you know, a couple of zeros in a bank account. Like,
that's not the motivator for you. So I'm curious, like,
(32:34):
you know, when you think about this and the implications,
where does your head go. I'm not a believer in
the as as as I mentioned a little bit earlier
or alluded to at least, I'm not a big believer
in everything has changed forever. Just because the history of
these history of of you know, black Swan events, whatever
you wanna call them. Um, this could never happen, and
(32:56):
then it happens, Um, is that a lot of things
do go back to the way they were because society
is resilient. So you know, for example, I'm sure Coachella
one will be packed. I just I just think it
will be. UM. And the notion that well, no one's
gonna go to you know, people are gonna think twice
(33:16):
before they go to you know, uh uh Los Angeles
Lakers game again, Like no, they won't, I mean not,
not not a year from now. They'll total totally gonna
go to a Lakers game, Okay, and you know, and yeah,
our people are gonna be more careful about that, coming
immediately out of this and and going back to work
and making sure they're um going back to work in
a safe way in in you know, in in in
(33:38):
in September or whatever month it is, um this year,
of course, but but by this time next year, people
will be going to sporting events again, and and and
you know, and playing flag football on the field and
the and the and and going to concerts. UM. I
just I just think that's the case. I do. I
do think that that the um historic belief that you know, UM,
(34:03):
there's kind of been this UM, I don't know, dogma
maybe that well, UM, you know, you can't really work
from home for too long, and you can't really build
a remote workforce because it doesn't really work. Everyone's got
to be in the officeite, on the same page and
in the same physical location. A lot of that I
think has has been sort of you know, we've now
run the experiment and are seeing actually you can do
(34:24):
a pretty good job with a bunch of your people. UM,
you know remote. UM. There's some business that or businesses
that are growing like a weed during this time, and
and that's with all remote employees. UM. So it's certainly
the case that some of the employees can be remote
and we can be just as just as effective going forward. UM.
And then I think another set of institutions that will
(34:48):
probably be disrupted and hopefully create even more jobs, are
you know, uh schools and universities there. You know a
lot of parents right now going wait a minute, I
was paying you know, extraordinary amount of money and having
to borrow money to to pay tuition, and my son
(35:08):
daughter is doing you know, two or three hours a
day remotely on zoom right now. They could go do
that with you know, one of these online universities UM
for one price. So I think, I think, I think
there will be some dramatic changes just based on we've
now run the experiment of could you do a bunch
of this stuff remotely and are seeing that it is possible.
(35:31):
You know, I'm sure there's some CFOs out there they're going,
wait a minute. We were spending two hundred fifty thousand
a month on travel and entertainment, and you know, we've
seen some impact to the next quarter, but not impact
to the next quarter. And now we're not spending any
money on travel entertainment. Is all that travel entertainment, you know,
has that all been really worth it? We now get
(35:51):
to find out, um, and I think some of that
will change. Interesting. Yeah, I think you're right on the
on the human component to the coach Hellas or the
Lakers games. In fact, we might need it more. Yeah, yeah,
that's that's right. Um. I'm a much bigger believer in
there will be more desire for a connection and the
realization that, wow, what have I been doing not you know,
(36:13):
going out and seeing my friends for dinner on Tuesday
night when I could have been doing that, And and
travel and seeing seeing people in places you don't think
about going to see that you'd like to see. I
think there will be, you know again, once it's safe,
there will be even more of that than there was previously.
Art of the hustle will be right back after this
(36:34):
short break. I want to ask you, you know, just
as we're sitting here and talking and I'm thinking about, man, like,
how lucky am I that I just get to pepper
you with questions now that we've created this format. But
you know, I want to talk to you about Twitter. Um.
(36:55):
You know, it's something that you uniquely have gotten to
think about more than just about anyone else on the planet.
And I, you know, I frankly still it's it's still
such an enigma to me. It's so big it's so impactful.
What and it's still and it's still ever evolving and changing.
It's I think a misunderstood you know platform. What did
it do for us? How did Twitter change the world? Well,
(37:17):
it did several things. It enabled the world to see
exactly what was happening in some location from the inside
out immediately. What do I mean by that? By inside out,
I mean you get to see through Twitter what's happening
in the world from the people that are in it,
(37:39):
not from outside observers of it like a reporter or
you know, or here's a video camera of what's happening
inside the stadium. You're getting to hear from the players
in the stadium. You're getting to hear from the people
participating in the event, whatever the event is. You're from
the you know, from the people on the plane that
(38:00):
crashed at you know, at at SFO on the flight
back from from Seoul, you know, who are tweeting just
crash landed at SFO. UM. That inside out view of
what's happening from the participants in an unfiltered way instead
of filtered through some third party commenting on it has
(38:20):
been I think overall awesome. It comes along with lots
of you know, UM challenges like people's using it, people
and state actors UM. And that is just in case
for anyone out there who still doesn't believe that for
whatever reason, it has been the case in the past
(38:41):
that state actors and currently use these platforms to try
to spread misinformation UM and discord UM. But I think
overall it's been great. You know, you get to see
the three sixty degree view of a person instead of
just the reporting of of narrative of of of of
(39:01):
a person or an event or a or a a group.
That's a great perspective on it. And and uh, you know,
Jack's particularly amazes me. You know, I see him as
like a once in a generation entrepreneur um. You know
the at the top of the interview I alluded to,
(39:22):
you know, baking bread and vipasana, which is you know,
his real life UM. And you know, the guy is
running both Square and Twitter. I'm gonna interrupt you to
tell you something about Jack that people don't realize just
because look, I'm not speaking out of school. Jack would
tell you he's an introvert by nature, you know, he
he is not UM. He's sort of like if you know,
(39:44):
if you told me, like, hey want you to get
up on stage, and you know, uh, improvised with this
group of people, I do it. And if you told
that to Jack, you know, he'd probably have a heart attack.
I mean, he's just an introvert by nature, but he's like,
he's really really funny. He's got this great into humor.
So you know, when I was running Twitter, Um, I
want to see you on Twitter, and he was chairman
(40:05):
of the board, we would have dinner every Tuesday night, um,
every week, uh and talk about the company and and
it just what was going on in our lives. And
he's he's extraordinarily funny. So um. So hopefully, as you know,
hopefully as he gets more comfortable speaking, speaking in in
front of a large crowd, so people will get to
see more and more and more of that. When I
imagine there's only so much you can say in the
(40:27):
present moment as a CEO of a publicly trade organization,
and for you, like, I mean, is it is that?
I guess I'm just trying to you know, if I
can pull out from your perspective, what makes exceptional leadership,
what builds exceptional companies? What is like the zero to
one for us all out here that are like, you know,
(40:48):
on the path because you you just you've lived it,
you've studied it, you've invested in every phase of businesses,
you've built, you know, different generations of technology, you've worked with,
you know the best of my generation. Um, you know,
like help help us arrive at some of the patterns
that you've recognized. Great leaders eat last, you know, they
(41:09):
they make sure the team has taken care of first.
They're high empathy. They're able to look at things through
other people's point of view, and they listen, and they
know that their job isn't to prevent mistakes from happening.
Their job is to correct mistakes quickly when they happen.
They admit their mistakes, and they make it easy for
(41:30):
people to tell them the truth. The faster you know
the truth, the sooner you can correct mistakes that have
been happened. How do you wrap that all into a bundle.
They're they're high empathy people. There are people who are
able to realize that everyone else in the world is
a me as well, um, And that's what makes a
great leader. Now are there exceptions to that? Of course,
there are some people that are once in a millennium
(41:53):
geniuses that are able to do things differently, but generally speaking,
I think those are the characteristics of a great leader. Well, Dick,
I appreciate it, man Um any other questions for me,
This has been awesome. I really appreciate you coming on
the podcast. I really appreciate your mentorship. I will say that,
like you know, UM, a lot of people celebrating the
(42:15):
end zones with you. A lot of people can be
really great friends. But when it comes to truly being
able to help strategize for things that other people haven't
seen before, you know that the hardest issues that you
know end up perplexing you as you scale in business.
You've been one of my you know, very you know,
most trusted advisors. Um, you know, somebody have always known
(42:36):
I could turn to when you know things are stickier
where they're above my pay grade or over my head.
And um, you've done it without the expectation of return.
It's clear, like you know, and and I just you know,
I think that that's the way that you lead by
example that I learned from. You know. I always remember
like Dean Smith, the former you know, the gold University
of North Carolina basketball coach, thing you know, like teaching
(42:57):
his basketball players, like the basics of do good things,
good things will happen. You know, you pass the ball
the right way and think about executing the right way
good things, the results will be generally speaking, with some outliers,
the results will be great. And I just kind of
feel like, you know, that's a good way to think
about living your life. Do good things for people, and
good things will happen. You don't have to like, everything
doesn't have to be a you know, what are you
(43:18):
gonna do for me? It's just a silly and I
just think that's a it's a scarcity mentality instead of
instead of an abundance mentality. So I'm more than happy
to do it and always will be. So the score
takes care of itself. Yeah, that's yes, that's right. Thank
you for continuing the sports metaphor with the with the
Bill Walsh comment My pleasure, My pleasure. Well, thanks again, Dick.
(43:39):
I really appreciate you being on and keep rocking out there.
All right, Thanks buddy, We'll see you. For more podcasts
(44:03):
from my Heart Radio, visit the I Heart Radio app,
Apple podcast, or wherever you listen to your favorite shows.
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