Multi-Billionaire Marc Lore on How to Find Your Big Opportunity | Impact Theory
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Marc Lore, a serial entrepreneur and former Walmart e-commerce CEO, shares his philosophy on seizing opportunities where others see zero probability of success. He argues that big breakthroughs often lie in areas with non-zero probabilities that are currently untapped by competitors. His journey includes founding disruptive companies like The Pit, diapers.com (acquired for $550 million), and jet.com (sold to Walmart for $3.3 billion). Lore emphasizes the necessity of an "all-in" mentality, describing his approach as a choice between billions or body bags rather than settling for safety nets. He explains that he positioned himself financially by investing every dollar in savings into his first venture despite having a young child, and emotionally by framing failure not as a catastrophe but as a necessary step toward growth. To cultivate this aggressive yet focused mindset, Lore advises entrepreneurs to hire individuals who are "missionary" rather than "mercenary," meaning their primary motivation is impact and mission alignment rather than just money. He utilizes the SPAT acronym—Smart, Passionate, Optimistic, Tenacious, Adaptable, Kind, and Empathetic—to screen candidates during interviews. His interview process avoids standard questions that can be prepared for in advance to prevent unconscious bias; instead, he asks unique behavioral questions, such as determining the minimum amount of money someone would take to walk backwards everywhere they go for a week or forcing them to choose between being very nice but not smart versus very smart and not nice. He seeks candidates who prioritize kindness over intelligence when forced to choose, viewing this trait as essential for building trust within an organization. Lore recounts his own early struggles with risk aversion stemming from good grades in school until a pivotal moment at Wharton where he applied late after being told it was impossible. Despite the odds being close to zero, he submitted the application and received rejection, yet he learned that as long as probability is not mathematically zero, one must pursue the opportunity. He attributes his resilience partly to his upbringing with hands-off parents who required spectacular achievements for attention, fostering an internal drive to do big things. This mindset extends to parenting, where he prioritizes instilling empathy and kindness in his children over other traits, believing that a core of goodness allows everything else to fall into place naturally. When addressing how to build drive and overcome the fear of failure, Lore stresses that execution is far more important than having a revolutionary idea; one can disrupt any industry by doing existing things better or faster. He advises against dwelling on potential failures or worrying about what could go wrong, suggesting instead that entrepreneurs focus entirely on the single biggest step they can take today toward their vision. Regarding leadership, he identifies empathy as the most critical trait for retaining great people and creating a safe environment where employees feel heard and understood. Finally, he outlines his core values of trust, transparency, and fairness at jet.com, arguing that true empowerment requires sharing sensitive information like financials with staff and avoiding restrictive non-compete agreements to foster loyalty and commitment among self-motivated teams.
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I'm not going to accept that it can't be
done unless somebody proves it's a zero
probability. And often the case, you
can't prove it's zero. There's always
some non-zero probability.
And it's typically the stuff that has
that's really close to non-zero, nobody
else is touching. That's where the big
opportunities are.
Hey everybody, welcome to Impact Theory.
Today's guest is a profoundly successful
serial entrepreneur who has gone
head-to-head with some of the largest
companies on the planet and won. Fortune
magazine named him one of the smartest
people in technology, and given his
unprecedented
string of successes, it is not hard to
understand why. He's founded and sold
for massively disruptive companies,
including The Pit, which challenged
online giant eBay and had a successful
exit just two years after beginning. He
also co-founded diapers.com, destroying
the myth that people would never buy
diapers online, and establishing it as
such a powerful player in the industry
that it was acquired by Amazon for a
staggering $550
million dollars. And most recently, he
founded jet.com, which proved that it is
possible to compete directly with the
juggernaut Amazon and build an enormous
business in the process. Under his
leadership, jet.com raced at breakneck
speed to a billion dollars in sales and
subsequently sold to Walmart for a
dizzying $3.3 billion. Again, after just
two years in business. Now the CEO of
Walmart e-commerce, this Wharton
Business School grad is once again
demonstrating that the right idea
executed well can thrive against any
competitor. So please, help me in
welcoming the man Ernst & Young named
regional entrepreneur of the year, the
former wannabe farmer, and now storied
entrepreneur, Marc Lore.
ALL RIGHT, HOW ARE YOU DOING? HEY, YEAH,
GOOD TO SEE WELCOME, MAN. YEAH, THANKS.
Good to have you on the show.
to be here. And dude, the fact that you
did it once, already amazing. To do it
two, three, four times is pretty crazy.
What is it that you understand that
makes you so successful that you think
other people are missing?
I don't know
it's necessarily other people are
missing it. I'm I'm willing to do
whatever it takes, like create a a
situation where it feels like life or
death. Billions or body bags?
Billions or body bags, yeah. No, but in
in all seriousness, that I think is the
distinguishing characteristic because
all four of the businesses that were all
turned out to be successes, but
if I didn't put it into that extra gear,
I think none of them would have made it.
Like I I I really think that you have to
you have to be willing to to go all the
way.
How do you pull that off though? Like
the first time I get it because it
really is, I know you left the banking,
uh you didn't exactly have a safety net,
and so the first one really is sort of
billions or body bags, but after that, I
mean, you've had some huge wins. How do
you recapture that? I always
figure out a way to put myself in a
position where it can't not work. And
so, you know, the first one, it was not
only quitting, but I also put every
dollar in my bank account into that
first company.
Did you have kids at that point? Yeah.
So what do you tell people?
had a kid.
Like the number of people that want to
be entrepreneurs that come up to me and
they say, "Look, I've got this litany of
things, you know, I'm married now, I
have kids, I can't really do this. How
did you position yourself financially
and emotionally to pull that one off? I
just convinced myself that I would do
this for a you know, a year or two, give
it a real go. Because you had that much
saved up or The the idea was to take
everything I saved, invest it in the
company, take a salary, and then but I
still needed to raise capital to kind of
continue on. And so
um I hoped that I'd be able to do that.
And if I if I was able to, then I'd be
able to sustain. Worst case, wasn't able
to raise money,
had no more money in savings, and had to
go back into the workforce. Did I think
that I can get back in? Like was I
you know, past the point where I've no
return? And I thought, "No, you know,
I'm 7 years into my career. Worst case,
I can
go back and get a get a you know,
normal job again."
But it was
that was too much of a safety net. You
know, you could always go back. It was
investing every penny of savings into
the business. That was the real catalyst
for making sure that
it worked. And then in the subsequent
business, it was less about the money
that was at risk and more friends and
family money.
So every relative, every friend,
everybody I knew pretty much had a stake
in the startup. And I just didn't want
to disappoint all the people that I love
and care about, you know, by So that
drove me more than anything. In that
moment, so I find that pressure like
that can be powerful for people or can
be really destructive. Do you think
about framing it in a certain way that
makes it powerful for you? Like are you
sitting there putting actual words
behind the idea or is it just this
overwhelming sense of like, "Yo, I can't
[ __ ] this up"?
Yeah, it's just it just brings out
abilities you didn't know you had,
basically. I mean, just knowing
that you need to like go all in here and
do everything you possibly can and work
as hard
as as possible, you know, to make it
happen. It wasn't an anxiety like oh I
can't fail I can't fail it wasn't like
that. It was more just it's like you
don't really think about it. You just
go. It's sort of you know, if something
would happen in the moment, you know,
that was life-threatening you'd react in
a certain way that you needed to react
without having to think about it. That's
sort of the way it is.
Do you consider yourself an aggressive
person?
No. It's interesting. I'm not aggressive
either not by nature but I have found in
business it is like so when I think
about that story of you really backing
yourself against the wall or having your
friends and families money in the
business and you're like I really don't
want to mess this up for me to tap into
the aggression which is some that's what
I had to learn. So for me to go from an
employee to an entrepreneur it was a
game of learning to be aggressive. It
was
um being bold, striking, um even if I
was the youngest person or the least
educated that I had to be able to step
up to the plate to learn to try
something to be willing to fail all
that. So for me I really had to
cultivate an an aggressiveness about
myself to be able to do that. So taking
things like family money or whatever
which is not my story but things like
that and saying all right look like
actually talking to myself look man
you're not going to [ __ ] this up. You're
not going to let these people down.
You're going to do it but it's not going
to weaken you like this is going to make
you stronger. You got this. Stay
focused. Do you have an internal
dialogue like that or um do you have a
different approach to it? I didn't
really think about it day-to-day. It was
more just
you know, I can imagine if it would be
equivalent you know, the analogy of like
being in some sort of
bike race or or marathon or something
and you basically just
bike as hard and as fast as you can for
as long as your body will allow you to
do it. It's like just push yourself so
that when you get across the finish
line, you're like I I just couldn't have
gone any faster on this day, right? It's
just everything I had went into it. And
so once you put yourself kind of into
that gear,
you're in that gear, you're not really
thinking about it. You just I'm just
running as hard as I possibly can to
leave nothing on the table, you know?
How do you instill that in your teams,
or do you?
I look to hire people that are
self-motivated
who are more missionary than mercenary,
so it's not about
mean by that?
I mean
the primary motivation is not money. The
primary motivation is to make an impact
on the world, and
the company has a mission, it's got a
vision,
it's typically bold, and you want to
find people that really believe in it
and want to, you know, make a
contribution be a part of something
bigger than themselves, and they're
willing to to work hard at it. And yes,
money will come, and they want money,
but it's like secondary. Some people,
you know, like having worked in banking
for 7 years, it's very different. It's
I'll do whatever you want, just pay me.
And so find people that are really
self-motivated,
get them in the right position, and then
empower them. Give them all the
information, be transparent, trust them,
and then just empower them to run and
not micromanage or or get in their way,
and I find you have incredible leverage
when you have great people and you kind
of let them do their thing.
If you had to give a few key
characteristics to what makes somebody
great, so one thing I'll say is very
difficult is hiring, especially in a
hypergrowth company. You're having to
hire so fast. What do you What are some
key elements that you look for? Is it
like personality traits? Do you look for
different personality traits for
different jobs? Like how Yeah, I I have
I've learned so many lessons along the
way, and and where I I come out is
and I see this happen a lot of startups,
you'll be looking for like a certain
position, like I need a supply chain
person to do X, and the initial um
Do start from this place of trying to
find someone that's done that before?
The chances of find somebody that's
actually done it before
that's in the top sort of 10% for that
job
and get that person to quit their job
and come work and take the risk of a
startup. I found that that's it's too
hard, too much of a unicorn and
certainly like you said, if you're
hiring lots of people, you're not going
to get lots of people like that. So
then, does that mean you just go after
mediocre people? Like how do you solve a
problem? What I've done is I say, "Okay,
find the the the the smartest person I
can that exhibits the traits that I look
to hire for." You know, and the traits
would be I use the SPAT acronym which is
uh smart uh passionate, optimistic,
tenacious, adaptable, kind, and and
empathetic. And those are sort of the
the traits that I look for and the
entire interview process is trying to
make sure that that people align to
those uh traits because I find that
those people are more missionary, they
are more self-motivated, they want to be
empowered, they want to do big things
and if you find great people like that,
after 6 months or 12 months or 24
months, they want to be coming some of
the top people in their field because
they learn it and they've got all these
other traits there. So that's what I
found. I'm desperate to know what your
interview process looks like. How the
hell in an interview do you figure out
SPAT acronym? SPAT acronym? Yeah. So how
do you How do you suss it out? What are
some key questions? Do you have them
walk in and it's a maze? Like how do you
figure out if people are adaptable?
the here's the secret to interviewing.
For me at least, is never to ask a
question that somebody could have
already prepared in advance. Okay. So
that's kind of levels the playing field.
So nothing like what's your strength,
what's your weakness, tell me about some
great thing you've done. A lot of that
is just people that prepare and they
have good answers and and some people
have mentors or other people that have
been through it and say, "Hey, listen,
let's prepare, let's go through it. I do
it with my daughter. My daughter had an
interview. I'm like, okay, we're going
to like prepare for this. There you go.
Give me your strength, give me your you
know, I went through the whole thing.
She won an interview. She nailed it. It
was like the same questions. I I kind of
don't like that. I don't think you could
in an hour, which is typical length of
an interview,
suss out whether somebody has these
traits
if you're just asking sort of The other
thing that happens too, I find, is that
there's also like an unconscious bias,
you know, toward people that
do have more connections, you know, do
have parents that have kind of been
there, done that before. You know, I was
the first person in my family to go to
college, very different than my
daughter's now. And so, to avoid the
unconscious bias and also to to make
sure that you take level playing field,
I ask questions that basically
you couldn't prepare for. And really
trying to open people up to see who they
Yeah, I'll give you a great example. So,
one that I ask is
um
How what's the minimum amount of money
that you would take
to walk backwards everywhere you go for
a week? Can't tell anybody why you're
doing it. If they ask you to say, sorry,
I can't tell you. You have to go to
work, you have to go out on the weekend.
It has to be a normal week.
Backwards everywhere. The only thing
I'll do is I'll guarantee your safety.
And it's after-tax dollars. What's the
minimum amount of money that you would
actually take? Like if you if I wrote
you a check right now, you would go and
do it. But the minimum. People will come
up with with numbers, and I'll just
press them. I'll say Somebody will
say, you know, I I would I would do it
for five grand. I'm like, I don't
believe you'd do it for five grand. No,
this had this has to be actually, you
know, Yeah, I would. I would. And then I
then I go and leave the room and come
back with a check. Start writing it out.
They're like, whoa, whoa, whoa, whoa,
whoa. No, no, I didn't know you would
actually I said, I gave you I told you.
I told you. You know, so basically just
having the discussion like this is good.
Um I ask people questions like if you
could only be one of the two, what would
you be?
Um
you'd be known
to be very nice but not very smart or
very smart and not very nice. You can
only pick one.
And I find it's kind of interesting.
Some people like, "Oh, of course, you
know, I I can never not be nice to
people. So, even though I don't want to
be smart, I'll pick very nice and not
that smart."
And a lot of people like,
"There's no way I'm going to be not
smart." So, and it's kind of
interesting. It's probably like I'd say
it's probably 60/40
um asking that question.
Which is the 60? 60 is nice and I don't
know how many people are lying or just
think that's what I want to hear, but
probably 60 will say they're nice and
that's that's one of the things I'm
looking for. I definitely want people
given the choice to prioritize being
nice over being smart. It's more just to
get people opening up, get them talking
about real things, and seeing how they
problem-solve, how they approach
situations. How do you deal with
employees that have like a real
different tolerance for risk when you're
asking them to take a big swing or to
take a chance with you um on a new
business? I think it's really tough
to ask people
that are already in the organization
that haven't been vetted through a
process of, you know, are you
comfortable taking risk and ask them to
take risk now. It doesn't work. You You
don't want somebody to do something
that's contradictory to that their their
nature. You have to find the right
people up front. That's why in a startup
you have a clean slate. Um I found it's
something really interesting is that
people that have typically gone to
really good schools and done really well
grade-wise, they're used to getting A's
on everything, have a much harder time
taking risk because they just they look
at something that has a low probability
of success and say, "Well, why would I
do that? I don't I'm you know, I'm used
to getting A's and that's 95%."
So, why would I do something that has
20%? Well, because the outcome is 200X
or 500X. That's why you do it. But a lot
of people just can't get comfortable
with that. I think that's the difference
between an entrepreneur or not. Somebody
who's comfortable with a low probability
of success with a huge outcome. And then
you do go after it and you're okay
failing. I failed
so many times as a kid, whether it be
academically or otherwise,
that I was so comfortable with failing
that it was not even a constant you
know, it just meant That combined with
just being
chill it generally about things not
working out, the combination of that
allowed me to like freely just take
risks without any regard for
for like maybe failing. I love the story
that you have about applying to college
and the non-zero probability. I thought
that was really really a powerful story.
Walk us through that.
Okay. Yeah, so uh
you know, I didn't have good grades in
in high school. I really didn't
I
It was This is funny. I tell people this
and nobody believes the story, but it
was sophomore year in high school.
Remember walking down sort of the
corridor and somebody's like, "Hey,
where where are you going to go to
college? Or what are you thinking
about?" I said, "Oh, I'm probably just
going to go to Harvard."
And they said, "Harvard? Like
you you can't You're not going to get in
Harvard."
And I was like,
"What do you What do you mean? Don't you
just like kind of send your thing in and
pay and go?"
Like, "No, you have to actually apply
and they have to accept you." That was
sophomore year in high school is when I
learned that. Which is crazy these days
because I've been talking to my
daughters since they were like, you
know, this yay big about college. So,
but yeah, so I I didn't really know. So,
I didn't I wasn't applying myself in
school, didn't have good grades.
And my dad um had asked me
This is I did all the applying myself,
went to the colleges myself, parents
didn't know what was going on. And then
after the deadline, this is like in
January, February, the deadline was
like, you know, November, December for
applying to college. And my dad said,
"Hey, uh
um how's it going How's the college
stuff coming, you know? Where Where are
you going to apply?" I said, "Oh, I
already did. I applied. I'm done." He's
like, "Oh, you applied already? What Did
you Did you apply to Wharton?"
Cuz he knew that I knew that that was I
talked about that business school and I
wanted to do business and stuff. I'm
like, "Oh, no, I didn't I didn't apply
to Wharton.
Um there's no way I could have gotten
in."
He said, "Oh, really? There's no way you
could have gotten in? Zero? It's zero?"
And I said,
"Well,
I don't know if it's zero, it's pretty
close to zero, though." And I said,
"There's a lot of essays and all this
stuff." He's like, "Oh, so it's so it's
so it's work. You You didn't want to do
the work." I said, "No, I'm fine to do
the work. It's just It's basically my
guidance counselor told me I can't get
in.
Objectively, I don't think I can get in.
So, you know, I didn't apply." He's
like,
"All right." And he was looking at me
and I'm like, "All right, you're right,
Dad. I'm going to apply, you know?" And
uh and this was after the deadline. So,
this is like 2 months later. I went and
did all the essays, did the whole
application, did everything, sent it in.
And I'll never forget, it was like May
when you sort of got the letter. Went
out to the mailbox, I saw it. It said,
you know, "Wharton School." I ran in, I
opened it up.
Yeah, I got rejected.
Um
But But it really taught me a great
lesson because when I was opening that
envelope, it really felt non-zero to me.
Even though it was like I had no chance
of getting in, and it was after the
fact,
you know, and it probably was as close
to zero as anything could possibly get,
but I just felt like happy that I went
through the process. Nothing had
changed. It was still the same
probability, but I was really happy I
went through the process and took a
shot, and I was actually I had an at
bat. That letter, that chance, that it
could there's a possibility it could
have it could have said accepted.
Although, it's as close to zero as it
So, I've just taken that in life in
general. It's like,
just I'm not going to accept that it
can't be done unless somebody proves
it's a zero probability. And often the
case, you can't prove it's zero. There's
always some non-zero probability.
And it's typically the stuff that has
that's really close to non-zero, nobody
else is touching. That's where the big
opportunities are. When I when I heard
that story, man, I was really blown
away. Now, of course, I know the
punchline of your life is that it all
works out okay.
Uh so, hearing that story after seeing
what you go on to do with your life and
really thinking, "Wow, the the vast
majority of humanity, dude, when they
get that letter and they're rejected,
they're like, 'See, Dad, I told you. I
never should have wasted my time.'" And
the fact that you take that lesson to be
in that moment I held the envelope, it
went from when I didn't even apply, I
knew guaranteed I wasn't getting in to
now like there's actually a shot, and so
I'm going to pursue that in the future
that I'm actually going to try things.
Um I think that's really powerful. And I
I want to tie this back to something you
said earlier. So, part of what you look
for for people is adaptability. You also
talked about like you're sort of some
people have a personality this way, some
are that way, and don't don't put people
against their nature. So, how much of
that like
I want to believe, literally my life is
predicated on the belief that someone
watching this right now, hearing you
tell that story, they will now forever
think the way that you think about
non-zero probabilities, and they will go
on to do something that other people
wouldn't do. They weren't born that way.
They encountered that information, and
they chose to adopt it.
How adaptable do you think we are? Can
you teach that to somebody? Like, could
you teach that to your children? Or is
that like you either have it or you
don't?
Yeah, I think it's a little bit of both.
I think you can definitely be better at
it, but I do think there's something um
something that you're not necessarily
born with, but that you're raised with.
So, after what is it, 18 years
basically, you know, you know, at home
with with parents and the friends that
you surround yourself with, you're
definitely molded in in a certain way,
and I think it's it's tough to change it
dramatically after that. You can
certainly push it one way or the other.
Um but, you know, my starting point was
was way out there. You know, just just
given the way I was I was raised, you
know, which was pretty hands-off, you
know.
your parents teach you? Was it Was it
just the freedom to learn on your own
that was powerful, or did they give you
certain things that have really carried
through?
I think different things from different
parent. I think my my dad was was pretty
sort of non-present and
to get his attention, which was not that
frequent, you'd have to do something
pretty spectacular, which is probably
one of the driving forces to to this
this mentality, like, you know, you need
to go and do big things to to
be loved, basically, you know, like in
the world. And so, that's sort of has
been an internal drive and motivator
that I didn't really know and appreciate
until, you know, just recently you start
to think through stuff in your life and
why am I this way? Why does this make me
happy? Why am I driven to do this? And
then you kind of always, if you think
about it long enough, you tie back to
something in childhood. That's sort of
the catalyst. And so,
I don't know what it would have been
like without that, you know, and I
couple that, and I could have gone the
other way, I guess, and just been like,
you know, a bum and just forget it, you
know, like
and I went this other way, and I think
on my mom's side, I think there was such
incredible empathy and caring and
kindness on this side, and that the
coupling,
you know,
allowed me to to
to achieve what I had set out to do. How
do you think of that with raising your
own kids?
the key thing that I really always try
to instill is the sense of of caring,
kindness, and empathy.
And you can't pick too many things, as
as you know, like it's just kids are not
going to react, but if there's one thing
and you want to keep hammering it,
there's a good chance that that could
sink in, and I think that's kind of how
we approached it. It's sort of like,
let's go with with the the core, you
know,
be good to people,
um treat people as you want to be
treated. Be empathetic, be kind, and
just drill that into them.
Um
And not only drill it into them, but by
example as well. And see that. And I
think they have turned out to be very
kind, empathetic, and and that at the
core I feel good. There's
other things that you'd say as a parent,
"Oh, well, I wish they would be like
more like this and more like that." Or
but at the end of the day, if if you got
the the nucleus of of being kind and and
good, um then everything else everything
else is okay. And so you that's I would
just say you have to pick something.
When you're in banking, so you're
following a relatively um typical path
for somebody who's ultra ambitious. I
won't say it's just a typical path, but
for somebody who's really got some drive
and ambition, I get why you went into
that.
What was the epiphany that made you
decide that that wasn't for you?
When did you know that leaving was the
right thing? And how do you structure
your life now to make sure you never go
back to the way that you felt when you
were banking? Okay, sure. Well, I mean,
just starting out. So in grammar school,
high school,
I started every business that a kid
could start, you know, newspapers, car
waxing, lawn mowing, baseball cards,
recycling, lemonade stands, like
anything. And so I was quite
entrepreneurial as as a kid. But there
wasn't really any thought to like go to
work for a startup. That really wasn't
the case. I graduated high school in '89
and in college in '93. It just that
wasn't wasn't really a thing until the
late '90s really. Um and so I
for some reason got interested in stocks
in like 10 years old. And then started
reading books on derivatives and stock
options when I was like in seventh
grade, eighth grade. I was really into
it and went to Bucknell, studied
finance, knew I wanted to work with
stocks, went to work in banking, and 7
years into it I had gone pretty far
pretty fast cuz I was willing to work as
hard as it took to to kind of move up. I
was executive vice president, chief risk
officer, the youngest in the bank's
history kind of thing. You know, it's
like it was I things were going really
well, but I wasn't happy.
And and it really was interesting. I'm
like, "Wow, this is this is
as good as I possibly could have
imagined doing, you know, 6 7 years out
of out of college. I'm making a ton of
money. I'm doing really well, but I
wasn't fulfilled. I wasn't happy. And
when I was really thinking about it, it
I realized that what I really missed was
that sort of entrepreneurial
kind of feeling that I had as a kid, you
know, building something from nothing.
And so, yeah, I had this incredible pull
that that just toward entrepreneurship
and startup that got to the point where
I I just walked in to my boss's office
and said, "I'm going to quit and become
an entrepreneur."
And he's like, "That's really funny."
And I'm like, "No." He's like, "Oh,
well, what's your idea?" I said, "Well,
I don't have an idea yet, but" He's
like, "You're going to quit this job
making this amount of money. Didn't you
just have a kid?" Yeah.
"That's crazy." I said, "Yeah, well, I'm
going to do it." And he said, "Well,
you're serious." He said, "Well, if
you're if you're that serious,
I can I be your first investor? Can I
put 50" I think it was 50 grand, he
said, um
and I didn't know anybody with money,
and so
that was the seed. He introduced me to
two people. I met with those two people.
They introduced me to a couple people.
They and I wound up I met with like 200
angel people, you know, and got 60
investors.
I I have to stop you there because
people at home, if they're not having a
seizure right now and desperate for me
to ask the question that I'm about to
ask, then they're not paying attention.
So, all right, you're an insanely hard
worker, I'll give you that, but there
for a guy sight unseen to say you're
quitting, you have a kid, that's crazy.
That that's so risky. He's a banker, so
he's not exactly Captain Risk, and for
him to go, "I want" without knowing what
you're going to do, "I want to invest
$50,000 in you, which was I'm assuming a
very smart bet on his part. So,
what is it? So, I I think everybody has
something that they get early wins in.
So, I'll say for me it was verbal
ability. Now, I've put an inordinate
amount decades of practice into making
it useful,
but I definitely got disproportionate um
results out of every amount of energy
that I put in. Is there something that
he saw in you like, "Yo, this guy is so
good at finance. I know he'll never [ __ ]
up a business on that side." Or was it
something else? He knew you were a
natural-born leader. Like, what what was
it that he was banking on at that point?
I don't know exactly, but I would think
it's he probably saw a little bit of
what
I talked about before, which is I won't
let it fail.
Like, I'll do whatever it takes.
Billions of body bags, I'll do whatever
it takes.
You know, work as hard as is necessary
to make it work. And
I think also was I was just naturally
really good at math, which was something
that I was kind of known for, which
translates into finance, which
translates into other stuff, so. Can we
go into the billions of body bags saying
for a second? So, first of all, I'm I'm
not a fan of burn the ships at the
shore, but the do-or-die mentality to me
is so intoxicating. I have it very much
so. It's exactly the thing that I will
say is um because I don't think I'm
particularly bright. I don't have any uh
entrepreneurial skills whatsoever when I
started. Didn't have a lemonade stand.
Um
but dude, when I [ __ ] set my mind to
something, that is it. And literally,
I'm going to see it through no matter
what. All the success in the world I've
only sped up in terms of my drive, my
ambition, the speed at which which with
I move. And I am so desperate to be able
to package that up, to say magic [ __ ]
words to somebody, to give them that the
power of desire, so that they'll want
things the way that I want things.
Because it's not in a destructive way.
Like, I'm not I'm not destroyed by it.
You could take the wealth away. It
wouldn't matter. That wouldn't phase me.
It's that sense of like, "Dude, we have
so little time here, so much ability,
like potential that we can transform
into real skills." Like, how do you
infect people with that? That like is
one of the things like I always tell
people, "If I could give somebody a
gift, it would be the gift to have that
that desire I agree. I agree. That's
That is everything.
How do you build drive? How do you build
it in in Give it to someone, basically?
Yeah, like I want to believe it can be
built, right? Cuz I know it can't just
be given. So, I want to believe that
there's a process. I think there is, but
I'm always super curious.
the only thing the thing I've seen
um is
first of all, people need to feel uh
an intense sense of uh ownership of
their idea.
So, making sure that, you know, so when
somebody has an idea, you can help them
mold it, but it's their idea, and and
they have to feel like they're they're
accountable to it to the idea. Um and
then
um
pushing them to go out there and tell
the world, friends, family, everyone
about their idea and what their vision
is and what they hope to achieve. And
it's amazing how infectious that can be.
When somebody gets out there and they
start telling people like, "Wow, that's
a really good idea." Or, "Ooh, can you
do that?" Or, "I don't think you can do
that." Or, and you start whether whether
someone says you can't do it or they
say, "Well, it sounds like an amazing
idea." In either case, it's pretty
motivating. I find the people that are
scared to tell people about it because
they feel like some sense of like, "Now
I'm kind of committed." Or, you know,
"I've told all my friends about this big
idea I'm going to go do."
Um so, just getting somebody to go out
there It's kind of like, you know, if
you want to work out, they say, you
know, you know, put your shorts, your
T-shirt, your shoes right next to the
bed, get out of bed and put them on. And
then once you get them on, it's it's
easy to go. Um it's similar kind of
thing. It's like, once you have your
idea, start telling everybody you know
about this idea and how that you can
you're going to do it, and usually that
kind of starts to snowball, and then
people feel a sense of accountability to
it and then take friends and family
money. Some people say, you know, I
don't want to take friends and family
money. It's like, why? Well, it's yeah,
cuz it's it's kind of scary, right?
Um that's always been a motivating
factor, you know, just
knowing like you've got It's not only
the money, but it's also
hold you accountable. This is like
everybody you know will know that this
thing failed and there'll be a monetary
proof that it didn't work.
You said that you're equally motivated
by people telling you that it will work
or that it won't work. You literally
when I look every idea you've had has
seemed like a terrible idea and yet
you've turned it into these juggernauts.
So, one, how do you look at that and go,
"No, no, no, I see a path there." and
then two, when people start telling you
especially in the early days when you
did not have the track record to back it
up, how did you deal with doubt other
people like putting doubt on you? Yeah.
Well, I mean diapers.com is a great
example because
it was sort of I said
you know, my idea is is pretty simple.
We're going to sell diapers on the
internet and deliver them to people's
homes so they could have convenient
access to something that's a pain in the
butt. Um and then I talked to people in
the industry and they'd say, "Well, let
me tell you why it hasn't been done. It
hasn't been done because diapers are
loss leaders for places like, you know,
Walmart and Target and and big box. So,
they don't make any money on it anyway
and then now you want to pay for
shipping and you want to pay for
fulfillment and they're heavy and by the
way wipes, that's basically shipping
water.
So,
there's no way to make money.
And so,
and every time somebody says something
can't be done, there's also a part of me
that gets a little bit excited because
I'm like, okay, well, then nobody else
is going to do it. The big companies
aren't going to do it and then you kind
of put that juxtapose that against
really big market opportunity cuz what I
would The follow-up question I would
always ask was, "Okay, fine. You're not
going to make money,
but will there be customer demand? Will
people
want diapers delivered to their door
overnight at amazing prices?" And
everyone would say, "Oh, yeah. Yeah.
Yeah. There's no arguing with that.
People will love that." So, I'm
thinking, "Okay, so the demand is there.
Really big market.
Can't make money." So, then
thinking about how to solve that, well,
what if the diapers, the fulfillment,
the shipping, all that was a loss leader
online to basically sell that long tail
with unlimited shelf space. So, similar
to brick-and-mortars, they use it as
loss leader, you could afford to lose
more money on on diapers if you've got
million SKUs to sell them with limited
shelf space that you make money on.
And once I got convicted on that, that
that that made sense and that penciled
out, um
nothing was stopping me at that point. I
didn't care what anyone what anyone
said. And the more people said couldn't
be done, the more fired up it got me.
So. What do you think stops would-be
entrepreneurs?
Like if you had to So, I'll say for me
it's boredom. Boredom kills more
entrepreneurs than anything. They don't
understand what's coming for them. But
in your story, I I hear something else
and I wonder if there's something that
you
What stops them after they've already
started or from starting?
From starting or once they get going?
Yeah, I think from starting, and I know
a lot of people that have ideas. Um
first thing is people think the idea is
not good enough and they think the idea
is way more important than it really is.
And people try and find ideas that have
never been done before, which usually
result in niche little businesses. I
challenge people all the time to say
it's not about the idea, it's about the
execution. Find and pick any industry
out there, there's a way to disrupt it.
There's already a big market. If you
just figure out a way to do it a little
bit better and execute well,
you could make a nice return on on
capital. You could take anything. Take,
you know, pizza delivery or something
and just say, "Great, we know people
order pizza, they get it delivered, it's
great. What's wrong with it?" Oh, it
comes, it's not hot, the quality is not
good, you know, all of the things. Okay,
I'm going to create this, it's going to
be better quality, faster, what whatever
it is. Yeah, if you if you go and raise
capital and execute, you'll make that
work. Doesn't doesn't have to be um
anything super innovative. So, I think
that's what what holds people back. I
think once people get going, I think
they spend too much time thinking about
all the things that could go wrong, and
they get overwhelmed, and it literally
just paralyzes them. And I always say
like, "Forget about all that stuff.
Today's today. What's the biggest step
you can take today toward your vision?
Well, how can you make the most progress
against the vision today?" So, I always
push people to be really clear about the
vision, and then and then they take that
step, and then it's the next day. And
they say, "Well, what No, no, don't
focus on that. What's the biggest step
you need?" And as you start lining up
five, six, seven, eight weeks, months in
a row, you're like, "Wow, look back.
Made some serious progress." And focus
on like how far you've come, and and
keep the vision in mind, but don't get
caught up between today and the vision,
cuz you'll just you'll spin out of
control. I've seen that all the time.
How do you deal with failure?
Like surely none of your plans are like,
"We're doing this." And then you just
execute
no. I've so many like I've had before in
my life, so many failures, you know,
growing up and things. And the way I
deal with it is not to dwell on it at
all.
Just you just have to basically soon as
you recognize First of all, being
objective about progress. So, constantly
reevaluating
all the new information. So, you could
basically say, you know, here's the
vision, and you start marching,
and information's coming at you every
day. Competition, things, the market,
the world, whatever. You need to to take
in that information and then kind of
reassess constantly so you could be
objective about making decisions. And if
you get to a point where you realize
what you thought was true a year ago or
two years ago is not true anymore given
all this information, now where where do
you need to be? And as soon as you
recognize that being able to tell people
I was wrong, forget that. I know I said
that that was when the information was
this, new information, new, we're going
to pivot and then get everybody aligned
around it, but willing to take that risk
of looking stupid and and basically just
changing your mind. And sometimes that
happens over a year or two years,
sometimes it could be months. You could
be months and say, you know what? Wrong.
Objectively, we've got some new
information. Let's go in this direction.
So, I think you can't dwell, you just
have to reassess
and and go. If you're thinking about the
failure or feel bad even for a minute,
that's just a minute of lost time going
forward. If someone wants to be a great
leader, what do you think are the key
traits that they should be developing?
Yeah, it's funny. I I get asked this
question a lot and I thought about it a
lot.
If I had to pick one, and this usually
surprises people, if I had to pick one
trait of a leader,
it would be empathy. For any business to
be successful,
most people would agree you need to have
great people working in the business.
You need those people to basically give
you everything that the best they've
got. Um you need to retain those people,
they need to be happy. Like if you
really want to create a
a big sustainable business.
And then it comes back to, well, what
does it take for for the ability to to
sort of recruit great people
and then keep great people and keep them
motivated. It's like, well, they want to
be happy, they want to feel a part of
something. Okay. Like what drives
someone's happiness? At the end of the
day when you kind of
when you really get into it, it's people
want to be understood, they want to be
heard. They want to feel like that
there's something bigger than just
dollars and cents in business. And I
think being empathetic is putting
yourself in somebody's situation and
being able to
um
relate to how they feel about business,
situation,
things outside of business, personal
stuff, and
I think that builds a lot of trust and
respect and
um
people willing to
to to be more loyal and committed and
willing to give
the best that they've got when they feel
It's also feeling of safety, too.
I think when when when people feel
listened to, heard, and understood, they
feel safer.
And a lot of times people don't give
their best or do their best because they
feel unsafe, which brings to a whole
another topic around, you know, just
creating a a inclusive work environment,
which I think is super important. And I
think empathy plays a big part of that.
So, going beyond empathy, cuz I know
some seriously empathetic people who are
not good leaders. So, I'll say that is
necessary but not sufficient. That's
true.
Um what else are things that people
should be working on if they want to
lead?
I think entrepreneurs
um should be thinking about what I call
VCP, vision, capital, people.
At least 80% of the time.
And I really focus probably even more
than that percentage on those three
things.
It's constantly, you know, thinking,
shaping, molding the vision, and
articulating it over and over and over
so that everybody's crystal clear on
where we're going. What's the North
Star?
Um you know, making sure that you
set your org structures under the people
bucket. Set your org structure in such a
way that you can put people
um in spots where they've got end-to-end
ownership. I don't like creating
organizational structures where, you
know, you don't really know who's
responsible for what. So, thinking about
the org structure, getting that nailed,
bringing in the very best people in each
area
is the sort of P part, and then and then
making sure that you're able to go out
and raise the capital, which involves
selling your vision.
A lot of entrepreneurship is about
selling, selling the vision to to
investors, selling the vision to
employees, and then packaging it all up.
And And I think a good leader is able to
do VCP really well. On the people part
of it, the single most important thing,
um,
you know, outside of empathy, I would
say is is about, uh, empowerment. I
would say, especially in a startup where
you're hiring fast and moving fast, you
have to be able to empower people, which
means set the vision,
let them know, you know, uh,
what part of the org they're going to
represent and what they're, um,
responsible for, and then just let them
run. Let them create. Not get in their
way, not micromanage. You know, I think
if you really want to get the best out
of people, especially people that are
self-motivated, um,
it's it's let them let them do their
thing, and
give them a chance to show what they
what they can do.
You've talked about the power of culture
and core values. When you started
jet.com, what were the core values Core
values that let you guys run Yeah, was
trust, transparency, and fairness.
Interesting. And the reason why I picked
those three. And one of another thing
that I would say about core values to
anyone that's thinking about core
values, is and I've learned this lesson,
is you can't start with a list of 10. If
you get like a bunch of people in your
management team together and you start
doing a list, they'll all sort of
converge to a similar list of 10 things,
you know, you know, and integrity and
and excellence and all this all this
stuff. I think, um, for the core values
to really be core,
it has to be three or less. And you have
to be prepared to live those values as a
company in a way that no other company
in the world does.
Um and it's not just values like don't
confuse them with traits you're looking
for like the spot-on. Don't don't
confuse it with that. These are values
that the company things that company can
do to create a culture. And so when we
picked trust, transparency, and
fairness, reason why we picked those
three is because we felt those were the
three most important values um to lead
to empowerment. So if you want to
somebody feel empowered, you got to be
transparent as a company meaning be
willing to share information, share
financials, share sensitive information,
be really open, and know that there's a
risk that that it could get out and that
but that's you know, but be transparent.
Trust people. So you trust them
obviously with the information, but also
to to do their job, not to get in their
way. We didn't have a non-solicit
agreement, non-compete agreement. We
trusted people and it was more of a of a
of a handshake. Come work here and we're
going to give you information that you
won't get at other companies. We'll
trust you in a way that you've never
been trusted before. And we're going to
create a fair, safe work environment.
When you were starting out, what was the
secret to raising capital? I get now you
have a track record, there's going to be
a lot of people that would bet on your
side unseen at this point.
Uh but what was the key in the
beginning? How did you convince people
to give you money?
Okay. So the first was the pit um that I
really raised money for, which is an
online sports stock market. Um that's
where I raised I did 200 investor
pitches. So first thing I'd say is
prepared to do a lot of pitches. People
when they tell me like they're like,
"Oh, I'm having trouble raising money."
I'm like, "Oh, tell me. How many people
have you talked to?" "Oh, I sat with
probably like five or six people and it
wasn't really a lot of interest." I'm
like, "Five or six? That's about 500,
you know?" It's like
So the first
company I I you know, met with 200
people, 60 of them made an investment,
which is a pretty good hit rate, you
know, almost one in three. I still still
tell people there's 140 people that I
gave the full pitch to that said, "No, I
don't want to invest." So, even though
that's a great hit rate, um still way
more people are going to say no. But,
the thing that put a lot of those 60
people over was the fact that they saw
the passion that I had for the for the
idea and the commitment I was making,
not only for quitting my job, but I
invested $390,000
into the business. And they looked at
the sheet, I remember this one investor
very specifically, Garnett, he looked at
the sheet and he goes, "I see here you
invested $390,000. Can I just ask
I never seen that before. Why didn't you
round to 400?" I said, "Well, I only
have 390,000."
And he's like, "All right, I'm in. Put
me in." It was like immediate, you know?
And And that's what it triggered for me.
I didn't realize at the time that that
was actually, you know, uh going to be
going to be as valuable as it was, but I
started to use that with investors
after. I'd say, "You know, I I've
invested, you know, my entire life
savings in this business. That's how
much I believe in it, you know?" And
they're like, "Are you committed? Are
you really going to Like, yeah, my
entire life savings is in it. I have I
was making this salary. I'm making zero
salary now. Yes, I'm committed." That's
what got a lot of people over the hump.
So, I would say if you're raising money
from angel investors, it doesn't need
You don't need to have a network cuz I
knew nobody. It was just my boss and he
introduced me to two people. It's find
one person, ask them to introduce you to
a couple people, and then each person
you um pitch
ask to introduce you to a couple people.
And you just And And so, the network
just grows. And that's the way I did it.
It was no connections. A lot of people
think you need connections. You need to
know people. You need
There was no venture capital. There was
no institutional investor the first
time. It was 5 million bucks of just,
you know, 80,000 a pop on average,
basically, amongst 60 people. That's how
I started.
That's crazy, man. Dude, look, your your
string of successes is so gnarly.
Congratulations. How can people stay in
touch with you? How can they learn more?
I've been the last year I've been sort
of active on LinkedIn. I don't don't
really have time for other social media
stuff, but LinkedIn I try and you know,
once a week put a post I get an idea
about something I could be think could
be helpful to folks and I'll sort of
post it on there. So that would be the
the best way I guess. Perfect. Yeah.
All right, last question. What what is
the impact that you want to have on the
world?
What is the impact?
That's a big question. I just I mean the
way I live my life every day is I try
and
um
do what I was telling you I do with my
kids and just trying to be empathetic
and and give back and
um
you know, be you know, give more than I
take and I think that's kind of the
impact I want to make give as much as I
possibly can
um
without asking or taking much back in
return.
Amazing, man. Yeah.
Well, guys, he is starting to put out a
little bit more content. I would say
drink it all in. What he has done is
beyond extraordinary. To be that all in
in your life, to gamble on yourself, to
learn from your mistakes, to grow and
just continue to execute at a higher and
higher level. And that may be the most
important thing that he said, execution
is far more important than the idea. So
speaking of executing, if you haven't
already, be sure to subscribe. And until
next time, my friends, be legendary.
Take care.
Thank you, man. That was [ __ ]
amazing. While he was here on this
planet in his human form he did
something to make the planet better off
because he was here. He paid really good
rent and was happy because of it.