they’re all these business books that
say like hey be humble be humble be
humble but humility is not a natural
state for a kick-ass human being I was
writing terms and conditions for
websites some of which turned out to be
adult websites but they paid cash and
Travis Clinic while being CEO of uber
was ranked number two in the world a
tweet Ennis who here wants to compete
with a guy like that some of you aren’t
founders and you should admit that to
yourselves
he’s a former lawyer venture capital
investor company advisor and
entrepreneur he’s the proprietor of
lowercase capital a venture capital fund
in the United States he invested in seed
and early-stage companies like Twitter
uber Instagram and Kickstarter he’s
Chris Sacca and here is my take on his
top ten rules of success rule number
five is my personal favorite I make sure
to stick around all through to the end
for some special bonus clips and as
always as Chris is talking if he says
something that really resonates with you
please leave in the comments below about
quotes around it to other people can be
inspired as well enjoy
[Music]
too many investors invest in the things
that they just like and are comfortable
with and are within their own little
bubble and yet I think the distinction
we like to make is invest in things that
we know we can personally impact the
outcome of so I everyone could be
talking about the hot biotech deal and
it might be on the verge of curing
cancer but I cannot do anything to
advance the mission of a biotech company
quite literally and so we pass as cool
as it may seem if I’m going to mooch I
may as well mooch in the public markets
right and just throw darts and ride the
greens in red so if I believe that I can
take something that’s already a good
company and just make it a little more
likely to be a success then that’s a
rigged game for me it almost feels
unfair right and I can just be that much
more confident that the investors who
give me their money I’m gonna give them
their money back and a lot more after
that
I’m a big believer in the liberal arts
education I think it’s overrated
or it’s underrated I mean in that the
computer science stuff is overrated it’s
great technical skills are amazing but
what has happened as I referred to
earlier as we’ve just all the
storytellers are kind of gone and the
actual understanding of our users is
gone we’ve lost all that sensitivity and
yet I feel like that sensitivity comes
first from really knowing yourself so I
encourage people to take classes not
just an art music but and death and
dying dying in philosophy and theology
these things that you’ll never make
money on directly but I think one of the
most important things you can do is be
interesting like I I only really want to
work with people who’ve not only had
those crappy jobs I talked about but are
also interesting they have stories
there’s some meat to them there’s some
flesh there’s something really
compelling that’s who you want to be
with if you’re gonna spend night and day
building something together that’s who
you want to travel with these people
with these perspectives and these
stories and so an interesting this is
not something that I think you’re born
with I think it’s achieved by
vulnerability by adventure by all these
things so I really emphasize
interestingness I think you can get it
from from studying from reading
from putting yourself in uncomfortable
positions maybe more Americans should
just hang out naked the saunas that
could make the mortgage thing but but
traveling abroad going to Ethiopia and
helping dig wells that kind of stuff I
think builds a much more impressive
character so Stewart Butterfield who
runs slack obviously one of the most
successful investments in our portfolio
an amazing company Stewart is a liberal
arts major that dude is fascinating like
hanging out with that guy and talking
about anything beyond slack is amazing
he’s Canadian and he’s got great
insights in the US politics but you just
follow his snaps on snapchat the guys he
eats well he’s checking out art he knows
music really well he’s a really
interesting guy so he becomes a magnet
for talent you want to be a round Stuart
he enriches your soul and if you look at
the team of people he’s recruited
superstars like April Underwood Prince
it’s like he’s really recruited an
incredibly deep bench of people because
they want to have authentic and
multi-dimensional relationships with him
and I think it comes through in the
product – it’s time for step three step
three is to go on offense now what do I
mean by going on offense well you guys
all know sports is the big ten you can’t
avoid sports here you know what means to
be on offense offense is calling plays
managing the clock keeping the other
team on defense reacting to you now take
that term and apply it to the rest of
your life let’s take for example email
is your email inbox offense is that
playing offense no no no inbox stuff is
just defense the whole way imagine if
you took your to-do list and you posted
it on the door of your dorm room with a
little pencil there and invited the
entire world to come and add anything
they wanted to your to-do list well
that’s what your inbox is it’s a
publicly posted to-do list where it’s up
to everybody else to impose their whim
on you and even worse what happens is we
get up and it’s the very first thing we
check and so we get in there and we
start doing stuff for all these other
people and yet along the way we’ve
forgotten what we wanted to accomplish
for ourselves we haven’t done the things
that we know are important for us and
for our goals and so that stops now
it’s time to close your email and write
out your to-do list I don’t just mean
your to-do list for work I mean the big
to-do list for your life what do you
want to get done it’s an awesome time in
history to be authoring our own futures
in real time I mean the Internet makes
it possible to be just one degree away
from anyone in the world anyone of you
right now can send me a reply on Twitter
if you had your phones out and I’m that
accessible any one of you right now
could use the internet to become an
expert in any subject at all in 2007
back when I was at Google I went from
not knowing anything whatsoever about
the wireless industry to leading a group
that led a four point seven billion
dollar project that turned Verizon 18t
on their heads sent the FCC spinning and
changed the landscape of Wireless
forever paving the way for the apps we
all have on our phones today never in
history have there been fewer barriers
in the way no matter where we come from
what our parents did for a living how
much money we have we all can be
unqualified successes so who do you want
to talk to where do you want to spend
your time what do you want to learn you
just spent four years maybe five or six
but we’ll just forget that four years
for the most part taking the classes you
are required to take so now it’s your
turn to go on offense what are you
curious about where do you want to
travel what adventures do you want to go
on which fears of yours do you want to
tackle no offense also means owning your
personal brand your voice should be the
first two or three responses when I
search for your name on Twitter I’m
sorry on Google but how do i how do you
get there you tweet you post you blog
you comment you engage in discussions
you own your own identity the tools are
there to have a public identity and to
go on the record probably so and stand
for who you really are
I mean think of it I hire a lot of
people for a lot of jobs imagine why
would I ever hire somebody just on the
basis of a resume when instead I can
search for them online and get years and
years worth of insight into who they
really are and how they think and how
their ideas evolve and how they react to
the changing world rent those tools
exist for you to create your own
authentic brand completely within your
control and do it I’m sitting back and
watching television that’s playing
defense but going outside and being with
your friends
that’s offense provoke inspire don’t
just get involved but inspire others to
be involved that’s playing offense in
the spring of 2000 I was way over
levered into these two stocks in a
matter of few days I found myself going
from 12 million dollars to the good to
four million dollars to the bed so I was
25 years old I would four million
dollars I didn’t have anything to show
for I didn’t have a house or a boat or a
plane or anything I could sell paid off
I just I owed it and I came from a
middle-class background neither my
parents ever made more than hundred
grand in a year and I was just stuck and
I had to make some choices then about
whether I was going to quit and you know
or try to declare bankruptcy or whether
I’d try and fight it out and it happened
just as I was graduating law school
actually and so I said well I’m going to
try and fight this out and I’ll take a
sell-out job as a as a corporate lawyer
out of Fenwick and West and I’ll try and
grind this out and so during the day I
would do corporate law stuff at a tech
firm and at night I would do pretty much
anything that somebody would pay me to
do short of giving blood or massages
he’s like Craig’s Craigslist for this I
did go on Craigslist I was writing
contracts and business plans and
renaming companies there’s a thing
called Elance out there there’s now like
oDesk and rentacoder and stuff but
Elance is the first of those markets and
i was the first lawyer on Elance and so
I was I was writing terms and conditions
for web sites some of which turned out
to be adult web sites but they paid cash
and and so I even did a voiceover for a
book once yeah who knew but I actually
screamed for a few hours to make my
voice super raspy that was what they
were looking for in the character so but
I just did anything I could to try and
pay off his debt and it took me from
then till till basically the Google IPO
to selling another company in the Google
IPO before I got back to zero mm-hmm net
worth and I’ll tell you no matter how
early you are in your career the richest
you will ever feel is when you owe zero
dollars to anybody that’s the very first
time in your life when you’ve got
choices you can you could go join the
Peace Corps you go travel the world you
could do anything I actually celebrated
by throwing a BYOB party at my house
like I’m not going in the red to treat
all you guys but that that was a real
pivotal moment in my life um I’ll tell
you I just I never really considered any
other option I never considered moving
back with my parents to Buffalo New York
I never considered declaring bankruptcy
I just can’t always knew I would fight
my way out of it and I think that’s
something that for those of you who are
founders I I’d encourage not everybody’s
a founder it’s easy to kind of sign the
paperwork but some of you just aren’t
founders and there’s a time when you
have to admit that to yourself
that it’s cool to have a startup but you
may not be a founder you may not be the
kind of unstable mentally askew person
with the slightly manic-depressive side
who is uh who knows in the face of
insurmountable odds that you’re going to
win and I don’t mean is convinced that
you can sell people and convince people
of that I mean you know in your bones
that you’re going to make it out I think
that’s something that was a little
different about me it was like in that
whole as advisors were saying look just
go BK and seven years from now you can
walk away from it I just knew I would
fight my way out of it and I didn’t have
to convince myself or anybody else I
think
you are unforgivingly who you are have
you always been like that
no what what happened like when I was in
college were you like like were you ever
insecure I’m still am insecure like that
I mean there’s probably people
snickering backstage right now that
questions like um I when I was in
college I didn’t want to come out as a
progressive because I would eliminate
like half of my future employers and in
Washington DC I was like look I gotta
look neutral here so I can get a job
someday um I I found progressively you
know and some of these license were
foisted upon me I mean I mentioned
earlier so not to repeat a story but
it’s a Google I am working on this team
and this Wireless stuff it was
incredible my responsibility Larry had
given me Larry Page giving me billions
of dollars to go take on the wireless
carriers and I was in over my head I I
didn’t have a background on this stuff
and I was learning fast and I was pretty
good at it but one day a decision came
up and I didn’t know what to do and my
work partner wrote in the notes Chris
doesn’t know what to do about this and
at Google the notes are published to the
whole company so I see the notes get
published I’m like what you do you just
ruin my career everyone’s gonna know
like I’m smoking mirrors and I thought
it was over for me and then the next
meeting some new engineers who didn’t
report to me and Larry Page himself
showed up with ideas on what to do is
solve this problem and I was like oh my
god I just became more powerful
I now have influence I have more bodies
working for me who don’t even report to
me and it was I mean I wish I could say
I was like it was an enlightened choice
I’d made it was totally void for me I
was angry about it but it worked and so
along the way I realized that the candor
the authenticity the vulnerability is
what actually attracts the other people
to you it’s it’s the insecurity roots
you in this place of showing your
impervious that you’ve got all the
answers but what that does is it renders
everyone around you helpless there’s
like I’m not valued here right and so
when you start to admit like I don’t
know what I’m doing I need some help
then people started tracking you and
working with you I mean I I have a
principle that I guide my life by and I
try and teach us through our
entrepreneurs called bold humility
they’re all these business books that
say like hey be humble be humble be hung
but humility is not a natural state for
a kick-ass human being right like if
you’re here you probably kick a lot of
ass at something you were probably the
best at something
you’re you have ambition you’re a
risk-taker you have learned to hack you
are a good talker
you have through the gift of gab wound
your way into an amazing situation you
hustle hustle hustle and I feel like
it’s unnatural to apologize for that
but where we get into trouble is when we
feel like we have to extend that to the
we don’t know and we have to feel
like we’ve got it all covered and so I
think I have had such a great like I
don’t know if I would have learned this
authenticity if I didn’t have Twitter
and the replies being like that means a
lot to me go for you know and and that’s
why I kind of live a lot of my life in
public as I feel I draw a lot of
strength and reassurance from from the
public being like blick that moment of
failure meant a lot to me and I identify
with it you haven’t gotten every
investment right tell me about the worst
misses that you’ve had or sort of the
the biggest setbacks there every
investment you get into you’re getting
in there because you think you have an
airtight thesis for why this thing is
going to work out you’re convicted
you’re passionate you’re putting not
just your money in but but all your time
and effort you’re your own brand and
your reputation is on the line and more
often than not we’re wrong but even more
painful are some of these ones where I
didn’t invest at all and they’ve gone on
to be the mega unicorns I think about
Airbnb and they told me the pitch about
renting out a room in somebody else’s
house while the owner was still there I
literally look those guys in the eye and
I said guys this is so dangerous man
somebody’s gonna get laid they’re
murdered and the blood is gonna be on
your hands I think this isn’t just a
really bad idea I think they’re
currently raising at a twenty billion
dollar valuation now so it’s my fun
probably missed out on hundreds in the
as a result right well I only have two
speeds like asleep or going all out that
life is way too short to do anything
else but I seek out argument you know uh
Travis Planet is just one of the most
opinion opinionated people in the world
and the nature of our friendship is
beating the show of each other you know
that I’ve heard that there’s a we 10s we
racing anecdote you want Attucks
truffula uh yeah maybe some of you guys
know this story but it was New Year’s
Day like 2010 maybe Travis to stay in
about our house in the mountains and my
dad loves playing Nintendo Wii tennis
he’s pretty good at it actually and so
he says Travis Travis come on let’s play
tennis let’s play you know and Travis
bleary-eyed because we’ve been up all
night for New Year’s and he says okay
mr. Sokka and they start playing and my
dad is like up swinging and going for it
and Travis just sitting on the couch
like eyes barely open kind of doing this
and he’s beating my dad who’s getting
visibly frustrated sweating his swinging
hard he’s like what the hell and then
Travis does that like Princess Bride
thing where he’s like I’m sorry mr.
Sokka but I’m not left-handed
you know let’s start playing
right-handed and he’s making movements
this big just that and he’s acing my dad
my dad is like what the hell is
happening here and Travis said okay mr.
sack I’m sorry and he uses the remote to
page over to the global leaderboard and
Travis clinic while being CEO of uber
was ranked number two in the world at
Wii tennis who here wants to compete
with a guy like that he was also he was
also globally ranked he was like a top
10 angry birds player Wow the guy’s a
maniac right so anyway I seek out people
who are not normal I seek out weird
people like I won’t invest in anyone
who’s not really weird I think you need
to have some kind of imbalance to do
this well tech nice and that’s what’s
exciting I mean I get most exciting this
time I’m on this show back then I said
Shark Tank I know everyone has their
different version of it and people ask
why I agreed to do it because the deals
there probably aren’t going to make me
any money or anything but
the biggest draw is if you watch that
show back home you’re like Mark Cuban
you’re foolish right and so I get to now
go on the show and on behalf of all of
America who wants to bust his balls I
get to do it from a few chairs away and
he’s wrong most of the time and so
that’s like a sport for me will you make
a good point it’s old tech but there’s a
ton of old tech in real estate because
it’s so sleepy that I’ve already seen a
new tech out there what’s there I
usually last week no no that’s not true
and that’s de living no that’s
denigrating to him Chris because the key
isn’t the software the software is the
easiest no no look mark you’re not
making any sense it on it I make a total
set no no you’re not we’re no nowhere
how are you aware of that I know this is
going over your head do you think people
drive down the street and look for
houses they see their dream home they
see a for sale sign they’d love to get
in you don’t know what do they do
mark and what do they do the device
exists today it lets you in by Bluetooth
not a circumstance if you’re lame acts
circumstance within one new line of code
it can let in anyone so in your example
I Drive by and I want it now
right now yep right now who do I call so
you ping in the Whitnall apply for the
existing line not exactly shut up and
listen don’t be mad at me that I
understand this better than you do okay
look you’re saying he’s got some special
way of giving us a meeting no no they’re
already ahead of him they had exactly
that I have to go to the agent to get in
order to get guys in order disguise that
means you’re sharks caboose agree look
how any agent gets into a house of the
other technology they walk up boom
they’re in the house what you’re saying
what the agents do you can enable for
the consumers absolutely right I can’t
imagine a pipe except if you’re not
using the agent you don’t want to call
the agent and you want to make it
available so the user right there and
somebody who’s comfortable with keys can
use but he can’t do that there’s no
natural advantage okay why don’t we
agree
Marco why are a million locked boxes the
traditional lock boxes why are a million
of them sold a year and why is the other
company have millions of dollars with
the sales already you’re doing exactly
this all they have to do is flip one bit
and expand their audience and then you
connect those boxes how do you connect
like guys I wish you luck getting your
money back
have a seat Chris will agree we disagree
no you got it wrong Chris I sometimes
wonder how you made all that money more
what’s success anyway its success about
making the most money no not no money
for the most part turns people into
jerks if you if you do become rich the
university fundraising and Development
Office will certainly want to stay in
touch with you and if you give enough
money you’ll get your name on a plaque
above the dirty laundry bin here in the
men’s locker room but that still doesn’t
make you a great person it definitely
doesn’t mean anyone will like you I mean
don’t get me wrong as I mentioned before
you’re never gonna feel richer than when
you’ve paid off those credit cards and
student loans but after that money tends
to be pretty on fulfilling almost all
the people I know have made a lot of
money they turned into that guy all
right well you know the guy who pops his
collar and if he and if it were up to
him and you’re wearing two shirts he
could pop both collars that’s the guy so
how will we know when we’ve done it
right what’s the ultimate measure of
success then what’s the key to success
well in my experience quite simply
success is happiness it all comes down
to happiness and I definitely don’t mean
that happiness that you feel when the
Gophers take over on downs in their own
red zone as great as that feels I mean
that happiness that quite literally
fills your lungs the kind of happiness
that makes a noise it announces its
arrival with a deep inhale on a deep
exhale that happiness you know that
happiness right that happiness is
success because it turns out happy
people get jobs happy people create
happy people win happy people fall in
love and raise families they lead and
change the world
happy people get what they want because
often happy people are the ones who
realize they don’t actually need much
more than there
have and they appreciate what they’ve
got happy people are contagious some of
you aren’t founders and you should admit
that to yourselves so it’s become very
fashionable to start something it’s
amazing you know when they when Justin
Timberlake plays somebody in a movie
about you know about a start-up that’s
awesome
there are lots of people making a ton of
money and on magazine covers but this is
a very special different journey that is
not actually suited to everybody you
have to be a little up you have to be a
little weird a little crazy a little
obsessive you probably have some
personal issues that make you different
like you have some demons a little bit
you may have trouble relating to other
human beings from time to time like you
don’t accept failure very well maybe you
go off a little bit maybe you struggle a
little bit with manic depression etc
like if none of those things sound
familiar to you you should probably quit
right now
oh sorry if that’s a little bit of a
downer but I just some of you should be
employees some of you should be partners
some you should be employee number you
know number one at a startup and and I
think right now oh that’s amazing they
actually showed us a hurry up please
sign yeah yeah I know I died that’s but
that’s good but finish but finish with
that because I think that’s powerful and
people should hear that no I
there are founders and then there are
team members and in an era where it’s
been so easy to get capital I just think
the posers should step aside I I guess I
just think are our industry is blind to
the impact to the to how
I think we have written human beings are
our motion our purpose our community our
collective humanity our empathy have all
been written out of the algorithm and I
think that’s going to cost us in the
long run it will not only help the rise
of despotic leaders but I think it’s
what’s actually severing our connections
between each other you know I think
[Music]
technology has evolved a lot faster than
our our primal brains have I think we’ve
lost track of how important presence is
you know constant notifications and
buzzing and what the impact that’s
actually having on our our health and
our lives and so I think if we don’t
wake up very soon to the absolute dearth
of humanity within what we’re building
and have that baked right into our
mission our values our purpose our
hiring who we brought into these
companies then we’re gonna lose we’re
gonna lose not just on the Investor side
not just on the product side but the
monoculture will eat itself and our
entire planet will suffer as a result
thank you guys so much for watching I
made this video because red Jeep lopa
asked me to so if there’s a famous
entrepreneur that you are going to
profile next please leave it down the
comments below and I’ll see what I can
do I’d also love to know what did you
learn from Chris that had the biggest
impact on you what lesson are you going
to apply most to your business or your
life please leave in the comments below
and I’m going to join in the discussion
finally I want to give a quick shout out
to Edwin who’s one of the assistants at
Toronto dance salsa everyone thank you
so much you’re picking up a copy of my
book your one word it really really
really means a lot to me and taking that
picture and post it on Facebook I really
feel in the love man so thank you guys
again for watching I believe in you I
hope you continue to believe in yourself
and whatever your one word is much love
I’ll see you soon
what advice would you give for someone
in their early twenties living in this
era in this time of yeah well everyone
spend less money mm-hmm I think the
freest you’ll ever feel is when you
don’t owe anybody any money when you’re
you have all these choices in the world
you know you guys have the benefit of
like how do you I’ve never I’ve known
one been exactly so you lost tons and
tons of money well first in the United
States we have to pay a lot of money for
school so that’s one of your competitive
advantages you know I left I left
college and then into law school so I
was seven years of school and I owed
like two hundred thousand dollars you
know and that was 20 years ago so so
that’s that’s bad I think it’s already a
competitive advantage you guys have and
you like to go to hospitals and not yeah
it’s amazing
all this stuff we’re about to break oh
okay
did I just start talking about Donald
Trump again yes I’m but so so I just I
think one of the most important things a
young person can do is just buy less
have less stuff steep stuff just you’re
a prisoner to your things right and so
you can pick up and travel more easily
you can have a smaller house you can
quit your job and go work in an NGO
volunteer work you can pursue your art
career if you have less a know less
money to few people so I think that’s
like number one see now you’re not even
focused oh now you’re just trying too
hard
I’m beginning to think that maybe you
and Matt the CEO of automatic have been
playing on that table a little bit I got
suckered I told you earlier I like to
play rigged games
I don’t invest in companies where I
don’t think we have a competitive
advantage to make it more likely to win
and I wouldn’t a challenge you to play
badminton because I suck
say like hey be humble be humble be
humble but humility is not a natural
state for a kick-ass human being I was
writing terms and conditions for
websites some of which turned out to be
adult websites but they paid cash and
Travis Clinic while being CEO of uber
was ranked number two in the world a
tweet Ennis who here wants to compete
with a guy like that some of you aren’t
founders and you should admit that to
yourselves
he’s a former lawyer venture capital
investor company advisor and
entrepreneur he’s the proprietor of
lowercase capital a venture capital fund
in the United States he invested in seed
and early-stage companies like Twitter
uber Instagram and Kickstarter he’s
Chris Sacca and here is my take on his
top ten rules of success rule number
five is my personal favorite I make sure
to stick around all through to the end
for some special bonus clips and as
always as Chris is talking if he says
something that really resonates with you
please leave in the comments below about
quotes around it to other people can be
inspired as well enjoy
[Music]
too many investors invest in the things
that they just like and are comfortable
with and are within their own little
bubble and yet I think the distinction
we like to make is invest in things that
we know we can personally impact the
outcome of so I everyone could be
talking about the hot biotech deal and
it might be on the verge of curing
cancer but I cannot do anything to
advance the mission of a biotech company
quite literally and so we pass as cool
as it may seem if I’m going to mooch I
may as well mooch in the public markets
right and just throw darts and ride the
greens in red so if I believe that I can
take something that’s already a good
company and just make it a little more
likely to be a success then that’s a
rigged game for me it almost feels
unfair right and I can just be that much
more confident that the investors who
give me their money I’m gonna give them
their money back and a lot more after
that
I’m a big believer in the liberal arts
education I think it’s overrated
or it’s underrated I mean in that the
computer science stuff is overrated it’s
great technical skills are amazing but
what has happened as I referred to
earlier as we’ve just all the
storytellers are kind of gone and the
actual understanding of our users is
gone we’ve lost all that sensitivity and
yet I feel like that sensitivity comes
first from really knowing yourself so I
encourage people to take classes not
just an art music but and death and
dying dying in philosophy and theology
these things that you’ll never make
money on directly but I think one of the
most important things you can do is be
interesting like I I only really want to
work with people who’ve not only had
those crappy jobs I talked about but are
also interesting they have stories
there’s some meat to them there’s some
flesh there’s something really
compelling that’s who you want to be
with if you’re gonna spend night and day
building something together that’s who
you want to travel with these people
with these perspectives and these
stories and so an interesting this is
not something that I think you’re born
with I think it’s achieved by
vulnerability by adventure by all these
things so I really emphasize
interestingness I think you can get it
from from studying from reading
from putting yourself in uncomfortable
positions maybe more Americans should
just hang out naked the saunas that
could make the mortgage thing but but
traveling abroad going to Ethiopia and
helping dig wells that kind of stuff I
think builds a much more impressive
character so Stewart Butterfield who
runs slack obviously one of the most
successful investments in our portfolio
an amazing company Stewart is a liberal
arts major that dude is fascinating like
hanging out with that guy and talking
about anything beyond slack is amazing
he’s Canadian and he’s got great
insights in the US politics but you just
follow his snaps on snapchat the guys he
eats well he’s checking out art he knows
music really well he’s a really
interesting guy so he becomes a magnet
for talent you want to be a round Stuart
he enriches your soul and if you look at
the team of people he’s recruited
superstars like April Underwood Prince
it’s like he’s really recruited an
incredibly deep bench of people because
they want to have authentic and
multi-dimensional relationships with him
and I think it comes through in the
product – it’s time for step three step
three is to go on offense now what do I
mean by going on offense well you guys
all know sports is the big ten you can’t
avoid sports here you know what means to
be on offense offense is calling plays
managing the clock keeping the other
team on defense reacting to you now take
that term and apply it to the rest of
your life let’s take for example email
is your email inbox offense is that
playing offense no no no inbox stuff is
just defense the whole way imagine if
you took your to-do list and you posted
it on the door of your dorm room with a
little pencil there and invited the
entire world to come and add anything
they wanted to your to-do list well
that’s what your inbox is it’s a
publicly posted to-do list where it’s up
to everybody else to impose their whim
on you and even worse what happens is we
get up and it’s the very first thing we
check and so we get in there and we
start doing stuff for all these other
people and yet along the way we’ve
forgotten what we wanted to accomplish
for ourselves we haven’t done the things
that we know are important for us and
for our goals and so that stops now
it’s time to close your email and write
out your to-do list I don’t just mean
your to-do list for work I mean the big
to-do list for your life what do you
want to get done it’s an awesome time in
history to be authoring our own futures
in real time I mean the Internet makes
it possible to be just one degree away
from anyone in the world anyone of you
right now can send me a reply on Twitter
if you had your phones out and I’m that
accessible any one of you right now
could use the internet to become an
expert in any subject at all in 2007
back when I was at Google I went from
not knowing anything whatsoever about
the wireless industry to leading a group
that led a four point seven billion
dollar project that turned Verizon 18t
on their heads sent the FCC spinning and
changed the landscape of Wireless
forever paving the way for the apps we
all have on our phones today never in
history have there been fewer barriers
in the way no matter where we come from
what our parents did for a living how
much money we have we all can be
unqualified successes so who do you want
to talk to where do you want to spend
your time what do you want to learn you
just spent four years maybe five or six
but we’ll just forget that four years
for the most part taking the classes you
are required to take so now it’s your
turn to go on offense what are you
curious about where do you want to
travel what adventures do you want to go
on which fears of yours do you want to
tackle no offense also means owning your
personal brand your voice should be the
first two or three responses when I
search for your name on Twitter I’m
sorry on Google but how do i how do you
get there you tweet you post you blog
you comment you engage in discussions
you own your own identity the tools are
there to have a public identity and to
go on the record probably so and stand
for who you really are
I mean think of it I hire a lot of
people for a lot of jobs imagine why
would I ever hire somebody just on the
basis of a resume when instead I can
search for them online and get years and
years worth of insight into who they
really are and how they think and how
their ideas evolve and how they react to
the changing world rent those tools
exist for you to create your own
authentic brand completely within your
control and do it I’m sitting back and
watching television that’s playing
defense but going outside and being with
your friends
that’s offense provoke inspire don’t
just get involved but inspire others to
be involved that’s playing offense in
the spring of 2000 I was way over
levered into these two stocks in a
matter of few days I found myself going
from 12 million dollars to the good to
four million dollars to the bed so I was
25 years old I would four million
dollars I didn’t have anything to show
for I didn’t have a house or a boat or a
plane or anything I could sell paid off
I just I owed it and I came from a
middle-class background neither my
parents ever made more than hundred
grand in a year and I was just stuck and
I had to make some choices then about
whether I was going to quit and you know
or try to declare bankruptcy or whether
I’d try and fight it out and it happened
just as I was graduating law school
actually and so I said well I’m going to
try and fight this out and I’ll take a
sell-out job as a as a corporate lawyer
out of Fenwick and West and I’ll try and
grind this out and so during the day I
would do corporate law stuff at a tech
firm and at night I would do pretty much
anything that somebody would pay me to
do short of giving blood or massages
he’s like Craig’s Craigslist for this I
did go on Craigslist I was writing
contracts and business plans and
renaming companies there’s a thing
called Elance out there there’s now like
oDesk and rentacoder and stuff but
Elance is the first of those markets and
i was the first lawyer on Elance and so
I was I was writing terms and conditions
for web sites some of which turned out
to be adult web sites but they paid cash
and and so I even did a voiceover for a
book once yeah who knew but I actually
screamed for a few hours to make my
voice super raspy that was what they
were looking for in the character so but
I just did anything I could to try and
pay off his debt and it took me from
then till till basically the Google IPO
to selling another company in the Google
IPO before I got back to zero mm-hmm net
worth and I’ll tell you no matter how
early you are in your career the richest
you will ever feel is when you owe zero
dollars to anybody that’s the very first
time in your life when you’ve got
choices you can you could go join the
Peace Corps you go travel the world you
could do anything I actually celebrated
by throwing a BYOB party at my house
like I’m not going in the red to treat
all you guys but that that was a real
pivotal moment in my life um I’ll tell
you I just I never really considered any
other option I never considered moving
back with my parents to Buffalo New York
I never considered declaring bankruptcy
I just can’t always knew I would fight
my way out of it and I think that’s
something that for those of you who are
founders I I’d encourage not everybody’s
a founder it’s easy to kind of sign the
paperwork but some of you just aren’t
founders and there’s a time when you
have to admit that to yourself
that it’s cool to have a startup but you
may not be a founder you may not be the
kind of unstable mentally askew person
with the slightly manic-depressive side
who is uh who knows in the face of
insurmountable odds that you’re going to
win and I don’t mean is convinced that
you can sell people and convince people
of that I mean you know in your bones
that you’re going to make it out I think
that’s something that was a little
different about me it was like in that
whole as advisors were saying look just
go BK and seven years from now you can
walk away from it I just knew I would
fight my way out of it and I didn’t have
to convince myself or anybody else I
think
you are unforgivingly who you are have
you always been like that
no what what happened like when I was in
college were you like like were you ever
insecure I’m still am insecure like that
I mean there’s probably people
snickering backstage right now that
questions like um I when I was in
college I didn’t want to come out as a
progressive because I would eliminate
like half of my future employers and in
Washington DC I was like look I gotta
look neutral here so I can get a job
someday um I I found progressively you
know and some of these license were
foisted upon me I mean I mentioned
earlier so not to repeat a story but
it’s a Google I am working on this team
and this Wireless stuff it was
incredible my responsibility Larry had
given me Larry Page giving me billions
of dollars to go take on the wireless
carriers and I was in over my head I I
didn’t have a background on this stuff
and I was learning fast and I was pretty
good at it but one day a decision came
up and I didn’t know what to do and my
work partner wrote in the notes Chris
doesn’t know what to do about this and
at Google the notes are published to the
whole company so I see the notes get
published I’m like what you do you just
ruin my career everyone’s gonna know
like I’m smoking mirrors and I thought
it was over for me and then the next
meeting some new engineers who didn’t
report to me and Larry Page himself
showed up with ideas on what to do is
solve this problem and I was like oh my
god I just became more powerful
I now have influence I have more bodies
working for me who don’t even report to
me and it was I mean I wish I could say
I was like it was an enlightened choice
I’d made it was totally void for me I
was angry about it but it worked and so
along the way I realized that the candor
the authenticity the vulnerability is
what actually attracts the other people
to you it’s it’s the insecurity roots
you in this place of showing your
impervious that you’ve got all the
answers but what that does is it renders
everyone around you helpless there’s
like I’m not valued here right and so
when you start to admit like I don’t
know what I’m doing I need some help
then people started tracking you and
working with you I mean I I have a
principle that I guide my life by and I
try and teach us through our
entrepreneurs called bold humility
they’re all these business books that
say like hey be humble be humble be hung
but humility is not a natural state for
a kick-ass human being right like if
you’re here you probably kick a lot of
ass at something you were probably the
best at something
you’re you have ambition you’re a
risk-taker you have learned to hack you
are a good talker
you have through the gift of gab wound
your way into an amazing situation you
hustle hustle hustle and I feel like
it’s unnatural to apologize for that
but where we get into trouble is when we
feel like we have to extend that to the
we don’t know and we have to feel
like we’ve got it all covered and so I
think I have had such a great like I
don’t know if I would have learned this
authenticity if I didn’t have Twitter
and the replies being like that means a
lot to me go for you know and and that’s
why I kind of live a lot of my life in
public as I feel I draw a lot of
strength and reassurance from from the
public being like blick that moment of
failure meant a lot to me and I identify
with it you haven’t gotten every
investment right tell me about the worst
misses that you’ve had or sort of the
the biggest setbacks there every
investment you get into you’re getting
in there because you think you have an
airtight thesis for why this thing is
going to work out you’re convicted
you’re passionate you’re putting not
just your money in but but all your time
and effort you’re your own brand and
your reputation is on the line and more
often than not we’re wrong but even more
painful are some of these ones where I
didn’t invest at all and they’ve gone on
to be the mega unicorns I think about
Airbnb and they told me the pitch about
renting out a room in somebody else’s
house while the owner was still there I
literally look those guys in the eye and
I said guys this is so dangerous man
somebody’s gonna get laid they’re
murdered and the blood is gonna be on
your hands I think this isn’t just a
really bad idea I think they’re
currently raising at a twenty billion
dollar valuation now so it’s my fun
probably missed out on hundreds in the
as a result right well I only have two
speeds like asleep or going all out that
life is way too short to do anything
else but I seek out argument you know uh
Travis Planet is just one of the most
opinion opinionated people in the world
and the nature of our friendship is
beating the show of each other you know
that I’ve heard that there’s a we 10s we
racing anecdote you want Attucks
truffula uh yeah maybe some of you guys
know this story but it was New Year’s
Day like 2010 maybe Travis to stay in
about our house in the mountains and my
dad loves playing Nintendo Wii tennis
he’s pretty good at it actually and so
he says Travis Travis come on let’s play
tennis let’s play you know and Travis
bleary-eyed because we’ve been up all
night for New Year’s and he says okay
mr. Sokka and they start playing and my
dad is like up swinging and going for it
and Travis just sitting on the couch
like eyes barely open kind of doing this
and he’s beating my dad who’s getting
visibly frustrated sweating his swinging
hard he’s like what the hell and then
Travis does that like Princess Bride
thing where he’s like I’m sorry mr.
Sokka but I’m not left-handed
you know let’s start playing
right-handed and he’s making movements
this big just that and he’s acing my dad
my dad is like what the hell is
happening here and Travis said okay mr.
sack I’m sorry and he uses the remote to
page over to the global leaderboard and
Travis clinic while being CEO of uber
was ranked number two in the world at
Wii tennis who here wants to compete
with a guy like that he was also he was
also globally ranked he was like a top
10 angry birds player Wow the guy’s a
maniac right so anyway I seek out people
who are not normal I seek out weird
people like I won’t invest in anyone
who’s not really weird I think you need
to have some kind of imbalance to do
this well tech nice and that’s what’s
exciting I mean I get most exciting this
time I’m on this show back then I said
Shark Tank I know everyone has their
different version of it and people ask
why I agreed to do it because the deals
there probably aren’t going to make me
any money or anything but
the biggest draw is if you watch that
show back home you’re like Mark Cuban
you’re foolish right and so I get to now
go on the show and on behalf of all of
America who wants to bust his balls I
get to do it from a few chairs away and
he’s wrong most of the time and so
that’s like a sport for me will you make
a good point it’s old tech but there’s a
ton of old tech in real estate because
it’s so sleepy that I’ve already seen a
new tech out there what’s there I
usually last week no no that’s not true
and that’s de living no that’s
denigrating to him Chris because the key
isn’t the software the software is the
easiest no no look mark you’re not
making any sense it on it I make a total
set no no you’re not we’re no nowhere
how are you aware of that I know this is
going over your head do you think people
drive down the street and look for
houses they see their dream home they
see a for sale sign they’d love to get
in you don’t know what do they do
mark and what do they do the device
exists today it lets you in by Bluetooth
not a circumstance if you’re lame acts
circumstance within one new line of code
it can let in anyone so in your example
I Drive by and I want it now
right now yep right now who do I call so
you ping in the Whitnall apply for the
existing line not exactly shut up and
listen don’t be mad at me that I
understand this better than you do okay
look you’re saying he’s got some special
way of giving us a meeting no no they’re
already ahead of him they had exactly
that I have to go to the agent to get in
order to get guys in order disguise that
means you’re sharks caboose agree look
how any agent gets into a house of the
other technology they walk up boom
they’re in the house what you’re saying
what the agents do you can enable for
the consumers absolutely right I can’t
imagine a pipe except if you’re not
using the agent you don’t want to call
the agent and you want to make it
available so the user right there and
somebody who’s comfortable with keys can
use but he can’t do that there’s no
natural advantage okay why don’t we
agree
Marco why are a million locked boxes the
traditional lock boxes why are a million
of them sold a year and why is the other
company have millions of dollars with
the sales already you’re doing exactly
this all they have to do is flip one bit
and expand their audience and then you
connect those boxes how do you connect
like guys I wish you luck getting your
money back
have a seat Chris will agree we disagree
no you got it wrong Chris I sometimes
wonder how you made all that money more
what’s success anyway its success about
making the most money no not no money
for the most part turns people into
jerks if you if you do become rich the
university fundraising and Development
Office will certainly want to stay in
touch with you and if you give enough
money you’ll get your name on a plaque
above the dirty laundry bin here in the
men’s locker room but that still doesn’t
make you a great person it definitely
doesn’t mean anyone will like you I mean
don’t get me wrong as I mentioned before
you’re never gonna feel richer than when
you’ve paid off those credit cards and
student loans but after that money tends
to be pretty on fulfilling almost all
the people I know have made a lot of
money they turned into that guy all
right well you know the guy who pops his
collar and if he and if it were up to
him and you’re wearing two shirts he
could pop both collars that’s the guy so
how will we know when we’ve done it
right what’s the ultimate measure of
success then what’s the key to success
well in my experience quite simply
success is happiness it all comes down
to happiness and I definitely don’t mean
that happiness that you feel when the
Gophers take over on downs in their own
red zone as great as that feels I mean
that happiness that quite literally
fills your lungs the kind of happiness
that makes a noise it announces its
arrival with a deep inhale on a deep
exhale that happiness you know that
happiness right that happiness is
success because it turns out happy
people get jobs happy people create
happy people win happy people fall in
love and raise families they lead and
change the world
happy people get what they want because
often happy people are the ones who
realize they don’t actually need much
more than there
have and they appreciate what they’ve
got happy people are contagious some of
you aren’t founders and you should admit
that to yourselves so it’s become very
fashionable to start something it’s
amazing you know when they when Justin
Timberlake plays somebody in a movie
about you know about a start-up that’s
awesome
there are lots of people making a ton of
money and on magazine covers but this is
a very special different journey that is
not actually suited to everybody you
have to be a little up you have to be a
little weird a little crazy a little
obsessive you probably have some
personal issues that make you different
like you have some demons a little bit
you may have trouble relating to other
human beings from time to time like you
don’t accept failure very well maybe you
go off a little bit maybe you struggle a
little bit with manic depression etc
like if none of those things sound
familiar to you you should probably quit
right now
oh sorry if that’s a little bit of a
downer but I just some of you should be
employees some of you should be partners
some you should be employee number you
know number one at a startup and and I
think right now oh that’s amazing they
actually showed us a hurry up please
sign yeah yeah I know I died that’s but
that’s good but finish but finish with
that because I think that’s powerful and
people should hear that no I
there are founders and then there are
team members and in an era where it’s
been so easy to get capital I just think
the posers should step aside I I guess I
just think are our industry is blind to
the impact to the to how
I think we have written human beings are
our motion our purpose our community our
collective humanity our empathy have all
been written out of the algorithm and I
think that’s going to cost us in the
long run it will not only help the rise
of despotic leaders but I think it’s
what’s actually severing our connections
between each other you know I think
[Music]
technology has evolved a lot faster than
our our primal brains have I think we’ve
lost track of how important presence is
you know constant notifications and
buzzing and what the impact that’s
actually having on our our health and
our lives and so I think if we don’t
wake up very soon to the absolute dearth
of humanity within what we’re building
and have that baked right into our
mission our values our purpose our
hiring who we brought into these
companies then we’re gonna lose we’re
gonna lose not just on the Investor side
not just on the product side but the
monoculture will eat itself and our
entire planet will suffer as a result
thank you guys so much for watching I
made this video because red Jeep lopa
asked me to so if there’s a famous
entrepreneur that you are going to
profile next please leave it down the
comments below and I’ll see what I can
do I’d also love to know what did you
learn from Chris that had the biggest
impact on you what lesson are you going
to apply most to your business or your
life please leave in the comments below
and I’m going to join in the discussion
finally I want to give a quick shout out
to Edwin who’s one of the assistants at
Toronto dance salsa everyone thank you
so much you’re picking up a copy of my
book your one word it really really
really means a lot to me and taking that
picture and post it on Facebook I really
feel in the love man so thank you guys
again for watching I believe in you I
hope you continue to believe in yourself
and whatever your one word is much love
I’ll see you soon
what advice would you give for someone
in their early twenties living in this
era in this time of yeah well everyone
spend less money mm-hmm I think the
freest you’ll ever feel is when you
don’t owe anybody any money when you’re
you have all these choices in the world
you know you guys have the benefit of
like how do you I’ve never I’ve known
one been exactly so you lost tons and
tons of money well first in the United
States we have to pay a lot of money for
school so that’s one of your competitive
advantages you know I left I left
college and then into law school so I
was seven years of school and I owed
like two hundred thousand dollars you
know and that was 20 years ago so so
that’s that’s bad I think it’s already a
competitive advantage you guys have and
you like to go to hospitals and not yeah
it’s amazing
all this stuff we’re about to break oh
okay
did I just start talking about Donald
Trump again yes I’m but so so I just I
think one of the most important things a
young person can do is just buy less
have less stuff steep stuff just you’re
a prisoner to your things right and so
you can pick up and travel more easily
you can have a smaller house you can
quit your job and go work in an NGO
volunteer work you can pursue your art
career if you have less a know less
money to few people so I think that’s
like number one see now you’re not even
focused oh now you’re just trying too
hard
I’m beginning to think that maybe you
and Matt the CEO of automatic have been
playing on that table a little bit I got
suckered I told you earlier I like to
play rigged games
I don’t invest in companies where I
don’t think we have a competitive
advantage to make it more likely to win
and I wouldn’t a challenge you to play
badminton because I suck
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