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🎙️Episode 15: “The $500 Million Lesson You’ll Never Learn in Business School" - David Lichtenstein
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What happens when everything you’ve built — billions worth — comes crashing down? When failure stops being theory and starts being personal? David Lichtenstein faced it. And what he discovered after losing $500 million didn’t come from a boardroom — it came from something much deeper. It’s about knowing where you come from. Understanding what makes you one of a kind. And finding the strength to rebuild when logic says you can’t. 🎧 Hear the story behind one of the boldest comebacks in business — and the mindset that made it possible.
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two, one, go.
>> Imagine acquiring an $8 billion entity
and then shortly after you acquire it,
the entire market crashes and you're
left with a personal loss of over $100
million.
How do you deal with that? More
importantly, how do you dust yourself
off, pick yourself up, and somehow
create incredible success? Listen to the
fascinating story of David Likenstein
this week on Jewish Grit.
[music]
>> David, I'd like to jump right into
Jewish grit. I mean, the concept is that
you're Jewish and that sometimes you got
to grit your teeth and you got to work
through difficult situations. when when
I say the word Jewish grit and I talk a
little bit about challenges and somehow
getting through them, what what enters
your mind? [sighs]
>> Well, I started my business on my own
knowing nothing about business. So, I
would say that every possible mistake
that you can make, I've made
>> and how do you uh rebound back every
time that you make a mistake?
>> So, it's a sense of core beliefs and
I'll share some of them with you.
>> Sure. I remember I once did a a deal in
Kentucky [snorts] and my flight was like
at 6:00 in the evening and it was done
at two. So the guy who my host said he
said, "Would you like to see a horse
auction?" So, um, I said, "Sure, racing
horses." Yeah. So, we went to the
auction and a brown horse came out and
it was like $2,000. Then another brown
horse came out and it was $12,000. And
another brown horse came out and it was
a million dollars. [laughter]
To me, they all look like brown horses.
Maybe one had a speckle, one didn't. And
the guy says, "You don't understand. The
first horse is really a laboring horse.
The second horse, it's a decent horse,
but it has no ancestry."
He says, "The last horse is a grandchild
of secretariat from one side from
Rolling Thunder on the other side." And
he said, "When these horses come around
the track and they see the finish line,
something inside of them, we don't know
what it is, just ignites. And those are
the champions." And that's what people
are betting on when they buy a yearling
for a million dollars. And I think it's
the same thing we come from originally
from Abraham, right? [clears throat]
Abraham, Bible says, went through all 10
of the 10 tests God gave him. And if you
Google the most difficult things that
can happen to a person in life and you
Google what happened to Abraham, they
coincide.
sickness, war, death, uh loss of his
wife, um child, anything you could
imagine. And he's called Abraham our
father.
And the message is, you know, if your
father was a great football player,
every college looks to you and they say,
"Oh, it's it's in the jeans, right? If
you're a
your your father was a great basketball
player, like that fellow from LA, right?
Mhm.
>> They say, "Oh, the kid's going to be
something." We have to look at ourselves
as we are the children of somebody of a
nation that's gone through every
imaginable hardship. So when it hits us,
we've been there, we've seen it, we've
done it, we've survived it, and so can
you.
>> Can I drill down a little bit more?
Could you give us an example where you
felt you had to uh draw on your
ancestral strength?
>> Yeah. Well, but my biggest um blowup
failure was um uh I bought a company
called Extended Stay America, a hotel
company.
>> Sure.
>> And I bought it for $8 billion.
And it went bust in the great recession
of '08.
>> Sure.
>> At the same time that Fanny went bust
and Freddy went bust and banks went bust
and Leman went bust
>> and um it was, you know, I I I
personally lost $500 million on one
transaction [snorts] and I inherited
nothing. It was all money I earned and
it was very painful and a lot of
compatriots of mine who went through
difficult times at that time such as
Leman never got back up on their feet
again.
>> But I said I have to get back on my feet
again and I have to draw on different
strengths that Judaism teaches us.
>> And that was one of them.
>> How do you find strength?
>> Well, one of them is knowing that we've
done it and we've survived more serious
things. I think there's another Jewish
teaching that is very powerful and that
is the belief that each of us is a
one-of-a-kind creation.
So the Talmud writes this 2,000 years
ago or 1500 years ago, but science tells
us the same thing. Each of us have our
own DNA, our own fingerprint.
>> More than that, if you go to a gym, you
know, today your
>> your retina is one of a kind. No two
people have the same retina. You look in
your eyeball and the door opens up.
Now the ear everybody's ear is shaped
differently. There's a company that's
raising money that they when bank calls
you they they want you to confirm a wire
and now they could with AR you can fake.
So one of the things is everybody's ear
canal is different and the way the
response bounces off your ear canal they
know who you are. Wow. So we are truly
each individuals and we also believe as
individuals
each of us has our own mission
and if something were to happen to you
nobody in the world could ever replace
you in that mission that you were
brought here to do. Everybody remembers
when the Challenger blew up and
everybody was killed six and the
Challenger, which was a multi-billion
dollar rocket, blew up because an 11
rubber gasket failed.
And that's a very Jewish concept. I
don't know if I'm the rubber gasket. I
don't know if I'm the engine, but I know
I'm irreplaceable. And I know I have a
mission. And being bankrupt isn't what
part of that mission. So, it must mean
that it's time to get back up on my feet
and it's time for you to get back up on
your feet and go accomplish your
mission.
>> How does one find their unique mission?
>> Um, I think at some point in life
there's something that speaks to you
really powerfully and that other people
may or may not hear and that's the voice
that comes to you. And it could be many
things like I know there have been many
different things I'm involved in such as
Kiraov right outreach which you know I'm
doing in my own way you know I have this
new Instagram podcast or it's a it's a
Instagram YouTube it's called we are off
the page and I think throughout life we
all have voices that we hear and that
others don't hear and uh I'm talking
about voices of good and voices of
reason and voices of positivity not you
know the crazy voices that people hear
and when we hear that voice it's really
our mission talking to us.
>> So how do you balance I know that I came
into your apartment and you were sitting
there and you had a safer you had a
Torah book open and that's what you were
doing. How do you balance that with your
professional career?
>> So I think it's a few things I think
it's about one is about like everything
else in life boundaries like when I do
this I do this when I do this I do that
and and set up you know the times that
you need for each of them and those
times in life change. So, for example,
when I went out to work, my wife was
expecting I was second kid. I had no
idea what I was going to do. And I went
into real estate because I figured you
really don't need to know much to get
into real [snorts] estate. It's in
effect.
>> No college degree.
>> No college degree, you know. And um I
work I was working um 100hour weeks
trying to get established and I couldn't
learn for the first few years much at
all. you know I was
you know but then as you get established
and you realize hey you know there's
such a thing called delegating you know
you you have you you're putting bread on
the table already and you say I have a I
have a certain amount of free time well
you can spend that free time scrolling
through Instagram you can do it you know
watching movies and Netflix and I always
get a kick when I see in the paper New
York Times again the 15 movies on
Netflix you must see this week before
they [laughter] phase down I speaking 50
I haven't watched a movie probably in 25
years right so it's a question of where
do you want to spend your really
valuable time and I'm not speaking
anything about you know if if if you
want to watch Netflix bless you if you
feel that it really chills you out and
takes away the stress in your life then
it's really important and holy but if
you feel there's something else that
speaks to you and I had learned in
yeshiva for many years beforehand and
learning is a really meaningful part of
my life and when I learn I'm able to
just the world sort of disappears.
You know what's amazing about when you
open up a gamura,
right? So, you're opening up something
that part of it, the Mishna was written
around 2,000 years ago in either
Jerusalem or Babylon. And the Talmud was
written in Babylon around 1500 years
ago. Rashi on the right is coming from
France, medieval France around a
thousand years ago. Toshus on the left
is around 900 years ago. Then I have in
the back I have the rush who's from
Spain and also you know and the rabb you
know and suddenly from the whole world
I'm surrounded by two and a half
thousand years of knowledge or 3,000
from five continents
and they're all for the most part often
disagreeing with each other and debating
and suddenly you get sucked into this
debates and you say who's right and
who's wrong and let's look at how has
time affected it how has time proven
who's right and who's wrong and the
world starts to disappear then setting
boundaries around it. And when I'm in
this room, my phone is gone
and um that's how you do it.
>> Has your definition of success changed
from when you were first selling
encyclopedias? I did my research. Um to
where you are today?
>> I don't think so. I think success to me
um is about fulfilling your potential
and your potential changes over time
too, right? But I think that in each one
of us
there is a book
and the book is waiting to be written.
Everybody writes their own story and
it's up to one person. You [snorts]
>> you imagine if American youth would all
know this and every year they the
beginning of whatever the year the
beginning of the year is for them they
take time to write a 365day
uh personal mission statement or
business plan. I think this country
would look a lot different. People are
react reactive. They're not proactive.
>> Yeah.
>> What do you think is just from somebody
who's had his has his finger on the
pulse of so many different things. What
do you think is the single biggest
mistake that young people starting out
at their career have when they make the
mistake? What is the mistake that they
make or
>> um I think young people don't realize
they don't teach this in school and
shame on them. [snorts] They don't
realize how often they will fail
and they don't realize that failure is a
part of the process. And we look at
digitized heroes like guys like
Zuckerberg or and there are people who
magically you know seem to have made it
through. And there's a reason for that
too. But the vast majority the 99.99999%
including most of the Forbes 400 have
failed many many times in Judaism.
Failure is part of life. [snorts] We we
fall and we get up and we fall and get
up. And every day in our prayers, we
say, "Lord, yesterday I think I really
screwed up, but today let's hope for a
better day." And when we recognize that
failure is part of the process of
success and you're never going to shoot
that three-pointer unless you've
>> taken the shot
>> many times and failed, right? One out of
two, one out of three, right? And it's
like that in life. So if we could say I
embrace failure as part of the process
and that the year that Babe Ruth hit his
60 home runs, he also led the league in
strikeouts, right? And that takes away
some of that stigma and fear and
embarrassment.
And I'm always talking about failures,
right? I've I've had many, right? I have
a a big book at home. all the failure
all my failures I keep it all the fool
stupid things I have done [snorts] right
and when we recognize that it's um it's
very empowering
right and I think many kids when they
start out have big dreams
right and we want to dream big there's
something you know I heard a story once
um there was a little girl in class in
art class she was like five years old in
first grade and she was drawing and
drawing And then the bell rang and the
teacher said, "Time's up." The kid keeps
on drawing. Teacher waits another
minute. She goes back and she says, "Um,
you know, it's it's time's up." She
says, "Wait, I need another few
minutes." She says, "What are you
drawing?" I'm drawing a picture of God.
So the teacher looks at she says, "But
but nobody knows what God looks like."
So the little girl looks at her. They
will in two minutes.
Beautiful.
I think we all have dreams and we have
big dreams
and [snorts] that's that's who we are as
children. And you know that if you go
into a a first grade class
and the picture the teacher p picks up a
red piece of oak tag and she says, "What
color is it?" If there's 25 kids in the
class, how many will raise their hand?
24 or 23.
Now, fast forward to college
and a teacher asks a question. He she
who has the answer to this on the black
on the board? How many kids will raise
their hand? Maybe one.
What happened between first grade and
college?
And the answer is
we happened. We shamed, we ridiculed, we
mocked, we laughed, and we taught us not
to raise our hands anymore. And that
those dreams that we had when we were
three and four and five to let them die,
right? And when we go back out into the
world or become older, we have an
election to make. Do we want to be the
five-year-old
or do we want to be the 20 year old?
And one of the ways to have that
courage, it's one of a few, is to
recognize failure doesn't mean anything.
It's just a step.
>> Doesn't define you at all.
>> It's a stepping stone. You learn from
it. I think um somebody once said, you
learn much more from your failures than
from your successes.
And that allows us to step back into our
own five-year-old shoes.
>> Do you have a mentor?
>> Many mentors. I'm a big believer. You
know, when we go someplace, and I travel
fairly often, my wife gets all upset. I
always, "Excuse me, where is that
street? I just want to be sure." He's
like, "You asked four times already."
You know, like just, you know, you
shouldn't ask so many directions. I'm
the guy I'm the least embarrassed guy to
ask. And people for the most part are
willing to think, you know, where I'm
going and I and I very rarely end up in
the wrong place when you ask 20 people
along the way, where you're going,
right? And that's sort of a metaphor for
life. There's so many expertes. I'm the
guy who's always saying in meetings,
wait, I don't understand that. Could you
explain that? I don't get it. Explain it
to me again. Why? Because there's
nothing embarrassing about knowing my
rebi and yeshiva was from
may rest in peace. And
what his most common line when you would
ask him questions was that's a good
question that I don't know the answer to
[snorts] that I don't know that I don't
know and I learned from him that the
wiser you are you recognize that you
don't know and the people who don't ask
and say think they do know it's either
out of embarrassment or stupidity
so you ask me if I have mentors I have
as many mentors
>> spiritual professional
>> what do you think I ask after after that
>> I think you surround by people
>> yeah because in all these areas there
are people who know more than me you
know there are so many different areas
of expertise in any business right why
not ask when you don't know
>> when you're looking to hire someone in
your company what are the key criteria
for somebody that you think could be
successful
>> I think that
absolutely the best criteria depending
on what age the person is is what has
the person done date
because even though they say in the
bottom of the commercials past credit is
no
>> indication of future.
>> It's not true.
>> Somebody who's paid their credit cards
for years will continue to pay their
credit cards and somebody who hasn't
won't pay you either. Right? So it's
really looking about what have you done
to date and if the answer is I've really
failed at that and I failed at that and
I failed you're probably going to fail
at your next job too. Right? So to me
it's not important what school you went
to but did you well were you interested
in doing well at at school? Did you do
well in your class? Did you do well? You
went to a C-class school because your
parents couldn't afford to send you to
someplace else or because you had to
help your mother because your father was
sick or there's a million reasons. But
while you were there did you put in the
effort and did you try? Because people
who try will always try and people who
have figured out a way to succeed will
always figure out a way how to succeed.
And to me that is the single best and
most relevant thing when you're hiring.
If you were sitting with our 70,000
80,000 students and young professionals
across the globe literally 300 locations
in five continents
and you had an opportunity to share one
message with them, what would you tell
them?
I would say don't let fear
impact your life. We know you have
dreams. You know you have dreams. You
know you have capabilities. You know how
to think big. The the the joker in the
deck is fear.
And if you could make that commitment, I
will not let fear get to me. I will fall
down on my head. I will be bloodied. I
will lose a tooth, but I will get back
up and I could fall again and I will get
back up again. Nobody's expecting you to
get it right. Not on the first time, not
in the second time, not on the third
time. But if you have that commitment
and you say, "I will not fear shame. I
will not let that negativity get in my
way." You will be successful in a way
that surprises you.
>> Thank you so much, David. It has been a
true privilege. So many great things to
think about. I think on my drive home
from Manhattan, I'm just going to try to
keep rehearsing what I heard and you
should continue to do great things for
the Jewish people.
>> Thank you. Honored to be here.
>> Thank you for listening to Jewish Grit
and Oly mentorship podcast. At OM
mentorship, we believe that everyone
needs a mentor. What better way is there
to tap into your personal and
professional potential than with a
Jewish mentor at your side? Learn more
at olami.org/metorship.
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