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🎙️ Episode 32: Find Your Next Gear with Jonathan Landau
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What do you do when logic says you’re done — but you’re not? When you hit your limits — in work, in life, or within yourself? Jonathan Landau shares a powerful mindset: you always have another gear. Finding that next gear is what builds resilience, fuels optimism, and helps you move forward when things don’t go to plan — in your career and far beyond it. This isn’t just about business. It’s a strategy for navigating challenge, pressure, and uncertainty in every part of life.
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What happens when you put a master
communicator and salesman
together with a dreamer in the world of
real estate? Layer on to that a man with
deep Jewish beliefs, you get one
interesting story. The story is next
level this week on Jewish grit.
Welcome to Jewish grit. I am super lucky
to have an amazing guest on Jewish grit
this week. Welcome Jonathan Landau, real
estate developer and just
a really great guy. So, Jonathan, take
us into your professional journey for a
moment. I know a lot about it. Um,
you're young and you're trying to figure
out your life. You try to hustle. Take
us into your first hustle. Uh, before I
was in the professional career, uh, when
I was, uh, a dropout from Yeshiva,
probably around 17 or 18 years old, um,
the first, uh,
I wouldn't even call it a business idea
that I had was, um,
the internet was just evolving. Uh, this
is, you know, call it early '90s.
And, um,
you were now able to get information
uh, either, uh, via
mailing, phone sources, or things like
that cuz it wasn't yet a worldwide web,
uh, where you can get information about
occurrences that took place in your
neighborhood or around your
neighborhood. And the concept was to
find out where there were fires that had
fatalities, uh, and sell, uh, to the
neighboring, uh, homeowners fire
extinguishers because at that point time
people really didn't have fire
extinguishers in their home or at least
in the
uh, world that we lived in people
didn't. So we would get these clipping
agencies that would give us news
indications of where fires occurred. We
would use some tracking
data to find out who the neighbors were.
We'd send them mailers and the the
statistics were if one out of every 50
people responded, you could make a lot
of money. Um unfortunately the data that
we were getting wasn't necessarily as
accurate as we thought it would be and
the hit rate was a lot less than what we
expected and after a while it became
clear that this needed more of a
definitive data source and program to
make it successful. Probably within a
year or two that was readily available
in the marketplace but at that point
point it wasn't. That was my first
endeavor into business. Um I'm cutting
you off for a second. What did you learn
from that?
Not every great idea is a success.
Has that served you well?
Um I'd like to say that I'm a glutton
for punishment. Uh but yes, I think
you've got to think through
your the the likelihood of success on
every endeavor.
Um I think you still need to be inspired
by your great ideas
as as I think we'll get to later on in
the conversation.
Part of inspiration is
taking the effort to the maximum extent
uh that you can and believing that you
have capabilities to succeed.
Uh but definitely I would say
uh
double checking yourself, triple
checking yourself is is good practice.
So that doesn't work. At some point you
decide that you're going to law school,
correct? Right. I I actually before I
got married my parents said you can't
get married until you have a livelihood.
I worked in a warehouse.
Uh in that for about a year before I
went to law school.
Um,
I was only 19 years old at that point in
time. Uh, I probably got paid, uh,
less money than, uh,
what a, uh,
uh, Minimum wage. the lowest minimum
wage, uh, was. They they paid me less
than that. But, it was a job. Uh, and
then I, uh, went to law school the
following, uh, August. Um, and I clerked
at a law firm while I was in law school.
I got paid even less working for the law
firm, but it was great experience, uh,
and that started my professional career.
Now, let's fast forward a bunch of years
later. You're not a practicing attorney
anymore. What happened?
Uh, I would say that at, uh, about after
practicing for five or six years, and I
worked really hard. Um, I had great
great success, um,
at in the practice of law, and I enjoyed
it. Um,
uh, it became apparent to me that
instead of actually representing other
people and helping them succeed in
business, it would make more sense to do
it with myself. And so, um,
you know, I think opportunities present
themselves in ways that you can usually
not script. And at that point in time, I
was, uh, working on a project, uh, that
generated a significant amount of
capital for one of my clients,
uh, and the opportunity came about for
me to be able to get involved in
starting a new business,
uh, with a development platform, which I
had absolutely no experience with, and a
real estate, uh, operating company
platform, which I also had very little
experience with. And I thought, "Hey,
if you don't, uh, step it up and take
advantage of opportunity, you're never
going to succeed beyond, uh, what, uh,
the average person, uh, can accomplish.
And so, it's worth taking a little risk
every now and then and getting out of
your comfort zone."
And, um, I think that,
you know, there's a tension not just in
it for average people in life, but also
religious tension as to, you know, how
far should you push things? How much of
your own sort of, let's call it, grit,
okay, do you want to
put into play? And and how far outside
of reasonable expectations
you should pursue things to try to
succeed. And
I would say probably hadn't a thought
through some of the implications of my
beliefs at that point in time, but it
was it was definitely inbred in me to
the point where
I believe you you talk about, you know,
successful Jewish business people. And
there's all kinds of, you know,
you could say stereotypes out there
about why Jewish people are successful
and and Jewish people control
everything. But the truth is that if you
really believe in God the way I was
raised and the way you were raised,
then you believe
that
the natural limitations that we have as
human beings are somewhat enhanced
by your belief in God. And so, it's
very, I would say, apropos that we're
coming up on the Passover holiday now.
And one of the
recitations that we say on the Passover
holiday at the Seder is we say, "If God
would have taken us out of Egypt and he
wouldn't have given us the Torah, it
would have been enough."
And everybody asks the question,
"Would it have been enough?"
And we have all Like without Torah. We
have all kinds of answers that we accept
like, "Oh, it would have been enough for
us to say thank you." Okay. You know,
for that we have to recite this and we
have this sort of tradition. And I think
that the answer is very simple.
It's not that it would have been enough
in the context that we understand. It
would have been enough in the context
of the following.
Jews are standing in front of a raging
water body of water that they cannot
cross and behind them is a army that
wants to murder annihilate him.
And nature at that point in time
doesn't say that they have a chance of
survival. They're dead. They're dead
before they get in the water not in the
water.
And yet God does something special. He
splits the sea and he's and he actually
creates a miracle that nature wasn't
able to comprehend.
And you could say, "Okay, we were lucky.
God had our back." Or you could say
this is a lesson for us to learn how to
conduct ourselves.
We don't just have natural limitations.
When we have God, we have another gear.
When we have God, we have faith
that we can achieve more than we can
with our own natural capabilities. The
whole concept in our religion of don't
say that you are this great warrior and
you did it on your own. As they say,
"Kochi vi otsam yadi, my strength usali
achayala za makes me this great
warrior." Absolutely not. We are not
allowed to believe that. Why? Because if
we do, we're diminishing our
capabilities. We're saying we're limited
to our own natural capabilities. But, if
we have this another gear that we can go
into which is belief that God
saved us and because he saved us, we see
that he's there in a way that we can
rely on. Now we have a greater gear. We
have another place to go and that's why
I think whether it's consciously
subconsciously thought out or not, the
Jewish people and the Jewish religion
have succeeded because we rely on God.
Thanks for sharing. Pleasure. I'm going
to push back a little bit. Go ahead. So
you start this real estate career and
you do have a lot of success. I guess
you had that extra gear
Right.
built a lot of things very successfully.
Can you bring us into a moment in the
next 10 or 15 years of your career where
you really needed grit cuz maybe it
didn't follow the narrative or the
script that you thought it would.
I mean, I think if you're asking for a
moment, it probably wasn't in the next
15 years. It probably took 17 years.
But, there before we get to that, there
are plenty of times in any
professional's career where you you make
an investment, you bet on something, and
it doesn't work out. And, you know, the
human reaction to that is to feel
dejected. The human reaction to that is
to sort of succumb to failure.
And, I would say that, you know, you're
about to close a loan, a hundred
million-dollar loan, a billion-dollar
loan. You're about to
acquire a property, and then something
goes wrong. An investor falls out at the
last minute. Um
you know, the the lender says they want
terms that you didn't anticipate. A
tenant's supposed to sign a lease, they
don't sign a lease.
These are all kinds of things that are
not in your control that happen every
day in everybody's life. Or, sometimes,
not every day, but at meaningful times
in your life. So, what do you do?
>> And
I think having the awareness that it's
not just you.
If you just are limited to your own
capabilities, you're screwed.
Dead in the water. But, if you realize
that the only way you got here in the
first instance was with the help of God.
You have, again, that gear to go into,
and that is optimism. That is taking
your own initiative and trying to make a
success out of a failure. And, many
times when you look back in retrospect,
you can see that that failure is what
actually gave you an opportunity for
much greater success that you didn't
even envision before. That's super
meaningful. So, now I'm going to drill
down a little bit. Um can you take If
you're comfortable, can you take us into
a scenario, a moment, uh an episode in
your life where that happened. And, I'm
curious like, okay, so this happens, now
what do I do? I pivot, I I I
providentially Talk to us about that.
Well, I mean I think I can go back as
recent as um
say uh
5 months ago. Uh we were we were closing
a loan for a half a billion-dollar
ground-up development uh that uh my
company was uh the developer on.
Uh
for the first 17 years of my career, I
worked with partners uh and did a lot of
big deals.
Billion-dollar deals, but um but there
was there was somebody else next to me.
And here I am now undertaking to do a
very large half-a-billion-dollar
development on my own. We have uh
probably one of the number one banks
that lends in the development world
that's giving us a
300-plus million-dollar loan. There's
lots of um
I will call it
complicated factors uh that are
underlying the transaction including
getting air rights and and um
you know
uh
making deals with neighboring properties
and and having equity investors that had
special deals and all kinds of different
transactions that had to align for us to
be able to execute. And at the last
minute, our lender pulled out. Um Did it
have to do with the political climate of
New York or I think I think it was a
contributing factor. Uh the climate
meaning obviously the socialist mayor uh
coming in was was not something that uh
banks felt comfortable with. Um it also
had to do with the fact that the uh
the housing department had made certain
determinations in anticipation of the
mayor coming in that were detrimental to
our project and that added some
significant cost to the project.
There were various factors involved.
Ultimately, it wasn't meant to be and
the lender pulled out. And They pulled
out on a Friday. Pause for a second.
You get that phone call.
Right. I had $26 million hard money up
at that point in time
that is at risk. And uh that's
>> What do you feel? Like is your entire
gut turned inside out? Like
is it adrenaline? What happens at that
moment?
>> you At that moment I was I was obviously
dejected.
>> It's dropped.
Um but I was not willing It was shut It
was right before Shabbos actually and to
me Shabbos is one of those days where
business has to be 100%
outside of your mind and you have to
enjoy this special moment of your family
and your friends and the time to sort of
shut off from the rest of the world. And
I knew that there wasn't anything I was
going to do in the next 24 hours. So I
was like, "Okay, just going to enjoy
Shabbos and we're going to deal with
this on Saturday night or Sunday."
That's huge.
>> And you were able to compartmentalize
that successfully. Yeah. That's great.
The bottom line is that, you know,
within a day or two sometimes the help
comes from from other people outside of
you. We have another brother who's a
debt broker and he went to, you know, to
a few people that were backups in the
original
um
I guess you could say marketing of the
uh financing of the project and we had
somebody that was really eager and
within three or four days we ended up
with a replacement lender um
and uh you know, it was it was a
different deal
um than the deal that I had envisioned
closing because it required multiple uh
financing uh stages and it required me
getting some of the other partners
involved, but ultimately
it worked out and probably worked out
better than what what what the original
loan would have looked like. So, you
know,
you just got to keep on chugging. Wow,
that's beautiful. That's a really nice
ending. I mean, it's not over yet, but
God willing it should just go from
strength to strength. I think one of
your greatest qualities, besides your
amazing heart that you have and ask
anyone who's met you that is, you're a
great communicator.
And you're a good salesman. And that's
what you need to build any type of deal
that you're working through.
What's What's What's that skill? What's
that gift? You sit down at a meeting.
These are new investors. You're trying
to pitch a new project. What do you have
to do to bring them into your corner?
In today's world, I would say that's a
particularly important
question to be able to at least consider
and answer in some way or another.
So,
the first thing you need to do is live
your projects. You need to You need to
feel them. You need to have a conviction
in them. You have to understand passion,
energy. You have to understand why
they're great.
And if you do
and you don't overthink
the process, then you can convey that to
other people.
Um and I think, you know,
I've I've delivered speeches in front of
large audiences before. I'm I'm always
unscripted.
And the reason for that is
it's much better, in my opinion, to
share
your experience with with other people.
And not everybody vibes with you. You're
not going to appeal to everybody all the
time.
But
when you're sharing the way you
experience something with somebody,
then it it's easy for them for that
energy to be received. And I would say
it's uh to a certain extent a um
an infusion of vision. And if you can if
you can share that vision
by sharing your excitement, by sharing
your energy, by showing why it makes
sense to somebody, then you're not
really selling them.
You're just giving them a vision for
them to buy into. And I think
uh that is probably uh something that
uh comes reasonably natural to me. Uh
and that's because I'm all in on
everything I do. Couldn't agree more.
You know, you have such a generous heart
and you love giving. It really gives you
a high.
Um and that's a big part of of who you
are and your wife is and obviously
I'm going to ask you a question. Now
that you support many institutions, you
give a lot of charity, like how do you
decide? There's an There's an unending
stream of opportunities for
philanthropy. What are the things that
pull you in?
I'm assuming it's like an investment to
you.
How do you invest?
Well, um from a philanthropic
perspective,
I am uh
not necessarily mainstream. So, I think
you know, people who are in individuals
who are who are in dire straits versus
institutions who are in dire straits
appeal more to me.
Um The human part of it. I think it's
also because they have less access uh to
assistance. I think it's because it's
it's then it's more of a personal
connection. So, that's that's something
that that appeals to me. Um
I think if you if you think about the
charities, the Jewish charities,
logically speaking, it it's an inhibitor
because there's a lot of charities that
are probably not great investments.
And if you do that and you think about
it in that way,
you will probably not give to some
people who are great investments. And
so, you have to try to shut off logic a
little bit and just really rely more on
emotion.
And that would be my approach to
charity. You know, most of the people
who watch this or listen to this are
young professionals or college students
living in a little bit of a crazy world.
They're probably experiencing
anti-Semitism in the workplace, on the
college campus.
And listen, I don't think either of us
ever dreamed growing up as a child that
we'd be living in a chapter of history
in the modern world that we're in right
now.
As somebody who is super exposed to so
many people, for so many different walks
of life,
like how does that make you feel? I
mean, is there a dormant anti-Semitism
that maybe some of the people you work
with have that you didn't know was
there?
Yes.
Um
let's just say
Jewish people can't expect the world to
love us if we don't love each other.
And unfortunately, we don't love each
other enough.
So,
it's a difficult thing to live with,
especially we have a grandmother that
went through the Holocaust who talked to
us about it all the time growing up.
Um and we I remember I remember thinking
as a as a young child like,
I think I may have even asked my
grandmother at one point, like "Why
don't you guys just shoot them?" You
know?
Obviously not understanding the
implications of what that would take as
a three-year-old asking that to my
grandmother, but
the this the problem is that just like
we're seeing today,
we thought
anti-Semitism was somewhat shelved uh
after the Holocaust. And it wasn't, it
was just suppressed. It's been there. It
is there. And it's a very difficult
thing to deal with.
But,
the best way we can deal with it is by
trying to live our life properly and and
loving each other to helping each other.
And also doing what's right in the world
and not not make not not desecrating uh
God by the way that we act.
And um you know, people who hate are
going to hate us.
Doesn't matter what we do.
But, we have to put blinders on, do the
right thing, and try to uh you know,
not make bad decisions. And
unfortunately, I would say liberal
Judaism
makes bad decisions.
And you know, you you go back in time
and you grew up as a kid hearing that,
you know, Jews voted for Hitler the
first time around.
And you say, "How could that possibly
be?" But, now we live in a time where we
see people voting for anti-Semites here
in our country. We see college campuses
just rampant with anti-Semitism.
And you have to say to yourself, "Okay,
we need to bind together and we need to
take a position and we need to try to
make much better decisions." You have a
microphone in front of you and it's an
opportunity to share a message with our
student and young professional
population around the entire globe
literally. These are people who are
starting their lives considering the
type of families they want to build, the
lives they want to lead. As somebody who
has significant life experience both
professionally and personally,
what would you want to share with them?
I would say
being able to live an Orthodox Jewish
life and celebrating Shabbos
with your family, with your kids, with
your loved ones, with your friends
is
the most special experience
you could ever have in this world. Being
able to shut off your phone for 24 hours
and reinvigorate your life with your
loved ones is a gift from God.
And
having holidays together with your
family and friends and enjoying your
life, and I'm not saying enjoy your life
in a synagogue. I'm saying enjoy your
life with all of the accoutrements that
are available to you, with all the
luxuries that are available to you, but
with your friends and family,
that is a special way to live and it's a
way that is integrated
in our religion.
And it's something that I think
everybody who is starting, everybody
who's already uh on the way
to uh mapping out their life should
should consider. And I also would say
something that's probably
unconventional, which is
you know, you can't be
an an exceptional father, you can't be
an exceptional husband, you can't be an
exceptional businessman life
life
if you're not happy.
And your happiness
your happiness in your business life,
your happiness in your personal life
is paramount.
Don't forget yourself. Don't forget your
spouse. Don't forget the relationship
that you need to have with each other in
order to be great parents, in order to
be successful in your business. Don't
forget the experiences that you need to
have
to be somebody that other people can
benefit from.
And that's something that unfortunately
we get so focused on whether it's our
business or our families or our
or our religion, we sometimes forget
about the fact that we need to be
healthy and happy. And And if you focus
a little bit on that, give yourself the
luxury
of treating yourself both mentally and
physically
and relationship-wise,
you will have a much better life.
This was a true pleasure. I think the
whole podcast is worth it just for me to
have this conversation with you.
Absolutely.
>> Keep Keep taking care of yourself, your
family, keep being happy, keep keeping
Shabbos,
and I keep making a difference in the
world around you. Thank you for
listening to Jewish Grit, an Olami
Mentorship podcast. At Olami 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/mentorship.
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