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Feel Behind at 25? Stay in the Game - Episode 48
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Adam Sasouness of Hudson Oak Development and Dwight Capital spent years grinding with almost nothing to show for it — and almost quit before it clicked. In this episode, he shares: ✅ How to tell the difference between stuck and slow ✅ How to keep going when your peers seem further ahead ✅ Why quitting early is the only guaranteed way to lose ✅ Why daily consistency — not one big break — builds a career If it feels like nothing's moving, that's not proof you're wrong. It might just mean you're not done yet.
Categories:Torah
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Auto-generated transcript. Not time-synced to the video.
From a conversation in a random parking
lot that would change the trajectory of
an entire family to renting out
apartments in Manhattan at the age of 16
to turning those abilities and that
journey into a super successful real
estate funding career.
You need to talk with Adam Sassounes
this week on Jewish grit.
>> [music]
>> Welcome to Jewish grit from beautiful
sunny Surfside, Florida and we got on a
plane with all our equipment just for
this moment to meet Adam Sassounes.
Welcome to Jewish grit.
>> Thank you. Thank you for having me.
>> Adam is the co-ceo, co-founder of Dwight
Capital. Adam, tell us what is Dwight
Capital?
>> We are a real estate finance firm. We
basically finance multi-family and
there's some some other uh
>> Tell us a little bit about your journey.
You tell me you grew up in a Persian
Jewish family, first generation. Yep,
like me.
And then what town were you in? Where
were you in this world?
>> I grew up in a town called Alpine, New
Jersey.
>> I know that.
>> Which is
>> beautiful.
>> Yeah, very nice town.
Uh no real Jewish community there. A lot
of Jews, but
um no real
>> religious Jewish community.
>> No real no religious Jewish community,
correct?
>> You went to Yeshiva?
>> And luckily my parents put me in in a
Jewish school in a Jewish school
uh which almost happened by accident. My
parents
used to be in the uh schmatta business.
They had some men's uh clothing stores.
My mom was scouting out schools, private
schools for me.
>> Secular private schools, right?
>> Yeah, secular private schools, yeah. Uh
she went to a very prestigious uh
private school in Englewood, New Jersey
called Elizabeth Morrow and she met uh
uh someone in the school there that she
knew. She She was working as an admin in
the school. I don't know exactly what
her function was. And she basically told
my mom like, "Listen, when you're done,
let's go to the parking lot. Let's go
talk outside." Basically, what
transpired during that conversation was
that she should not be sending her kid
here.
And it's not like the kids that go
through that system, they don't end up
on the right day or they're not on the
right path, right? They're uh
They tend to get into drugs, this, that.
It's not just not the right place. She
said, "Hey, why don't you go check out?
There's a Jewish school 2 minutes away
from here called Moriah." And she went
unannounced to the school without a
tour, set up, and uh the principal at
the time
walked her through the whole school. She
saw what was going on there. All the
kids were in kippot, smiling. She's
like, "This is where I want to send my
kid."
>> Wow.
>> So, from that, uh the family became more
and more religious. I happened to
have met my wife in high school who came
from a religious family in Monsey. So,
that also helped accelerate it further.
To point now where the entire family is
has been shomer Shabbos for a long time
now. Over 15 years, something like that.
>> I I'm stopping you for 1 second.
I I don't even realize I don't even know
if you realize what you just said.
There was one woman in a totally secular
private school who decided to have one
conversation with another woman out in
the parking lot, and she changed the
direction and trajectory of an entire
family generationally.
>> at Alumah. She didn't even work at
Alumah.
>> And she didn't WORK AT [laughter]
ALUMAH.
BUT I THINK THAT'S SUPER POWERFUL. Every
single one of us has tremendous power.
You never know. You have a simple
conversation. You can literally I always
say this. You have two trains leaving at
the same time from the train station,
and one is angled 1 mm to the right. At
the end, they're in you know, they're in
two totally different destinations. A
nice word, a little bit of guidance
could take a person on a totally
different journey.
>> I can't think, but I know of countless
examples of uh myself when I've given
advice to people, and I've even
forgotten about the conversation, and
they remind me about it months later or
years later and saying, "Hey,
like, do you remember that conversation
we had? Well, I did XYZ because of that
and thank you for that." And I had zero
recollection of actual conversation
happening. It actually just happened
yesterday.
I I went to my buddy's engagement party
and at the party he brings me aside and
he says, "By the way,
that conversation we had in the elevator
right in the office,
where you said like, it's time to get
married, like, figure it out.
>> [laughter]
>> Like, get it done."
Uh this was 5 months ago.
He said,
"After that, he got super motivated and
like the third girl that he ended up
going out with after that point, he
ended up getting engaged to and
hopefully God willing will be getting
married to and
>> Beautiful. Okay, so you you go to high
school. Did you go to Israel at all or
you stayed local?
>> I did not go to Israel. I I did want to
go to Israel. My dad was not a fan of
the idea at the time and also at the
time
was a lot of action going on there
unlike today, different type of action
than today. So, it didn't end up
happening. I went straight to NYU.
>> What did you go for? What type of
degree?
>> I had I was an econ major.
>> Nice. And what was your first job in
your life?
>> Was renting apartments in Manhattan.
>> How old were you?
>> uh this was in high school. So, I think
I must have been around 15, 16 years
old.
>> So, you were renting out apartments at
15 and 16?
>> Yeah, during the summers, yeah.
>> Now, did you have a job also while you
were in college? Was you holding
something down then?
>> I I kept renting apartments I think
through the freshman year in college.
Uh I did I attempted to do some retail
leasing and then I started doing
commercial sales. This was my senior
year in college,
uh which keep in mind was 2008.
>> Mhm.
>> So,
>> Who was buying anything? And who was
selling? Oh, selling maybe.
>> Right. So, didn't really make any money
but did learn a lot. Uh so, it was the
last 6 months of college and the first 6
months out of college. So, it was about
a year.
>> Can I take Could you take us back to
when you're 15 or 16? How does the idea,
the notion to rent out start doing
apartment rentals come into a
15-year-old's head?
>> You know, my family's in real estate and
it was just almost like a natural thing.
It's like, "Okay, you're going to be
renting apartments now for the summer
cuz this is a job that makes sense for
you to do and go out there, hustle, and
figure it out."
>> Okay, so you graduate college. Did you
get married when you were really young
cuz you said you met your
>> I got married at 20, yeah.
>> 20? And then what's your first like you
know, 9:00 to 5:00 or whatever hustle,
major hustle.
>> I was still doing this or attempting to
do the commercial sales thing 6 months
out of college and then
through my wife's family
I was able to get a job at Greystone.
It's another real estate finance firm if
you're not familiar.
>> I am.
>> And I was there
from 2009 through towards the end of
2013, so
>> And when did you like launch your you
know, your own
your own gig and your own company?
>> That was in January of 2014.
When I was
the month before
I turned 26.
>> Now what How do you go from a transition
of knowing you're going to get a
paycheck every single month to having to
figure it out?
>> So first of all, it was it was it was
both me and my brother. It wasn't just
me. It wasn't So we we did it together,
which is which helps, right? If you have
a if you have a strong partner, right?
Especially if it's a sibling, right?
Makes it that much easier. It And by the
way, it's not easy, but it makes it
easier. It we we were in a situation
where after doing what we're doing for
several years, we
we we knew what the secret sauce was,
what the winning formula was. It was
just a matter of execution.
>> Can you Can you share the secret sauce
or is it secret?
>> Uh the the key ingredient is is hard
work.
>> Okay.
>> Hard work and hustling and putting in
the hours. And and work ethic, right?
That's the key ingredient for anything,
for any success.
I've seen smart kids growing up through
elementary school, middle school, high
school,
and even college that use their brains
as almost a crutch and didn't develop
that work ethic, the grit. Other average
people like me, right, that actually had
to
supplement and yeah, and work super
super hard, develop the work ethic. And
for sure, there's no question, there's
no doubt in my mind that in any
business, in anything you want to do in
life, that is the number one ingredient
you need to have.
>> Can you take us into a moment a little
bit of a
valley? So, you hopefully have successes
cumulatively. Is there a moment you
could think of in your career either
personally or professionally where you
really hit a bad spot and you had to
really climb out? You had to use a lot
of Jewish grit, if you want to call it
that, to get out.
>> 2008 doesn't count.
>> times. You have to say Well, not only
not only 2008, but the first 18-24
months when I was at Greystone, I really
wasn't making that much money. So,
almost for
almost my initial 3-year work career,
I made almost no money, right? So,
um until I started to figure things out.
>> How did that feel?
>> It actually felt terrible. But,
everybody year two, year three, I
started to figure things out and then
after that, things started to
>> you were looking at yourself in the
morning each in the in the mirror each
morning,
like, how did you
get yourself to I got to go to another
day at the office when I'm not making
any money?
>> Day in, day out, day in, day out, work
ethic. Yeah. Yeah. I eventually climbed
myself out of that hole.
>> Did Did you have a big break at any
point? Like, you did your first really
large deal and you're like, "Okay, I can
do this."
>> No, it's it's were smaller deals that we
started cranking the smaller deals out.
Eventually became bigger deals, more
frequent. And uh like I said, it's
gained momentum and carried that
through.
>> What What do you guys do when like
there's a down market?
>> When When rates spiked in
Q2 of 2022,
>> Right.
>> through you could say the first half of
2025,
almost a 3-year period, um
yeah, it was on the multi on the
multi-family side, it was very, very
tough. It was very, very challenging
uh for us.
>> But you also have diversification,
right? You're also funding other things.
>> Correct. So, one of the one of the first
things that uh we did when we started
our business was we we said, "All right,
we need to get this HUD lending platform
off the ground." which was a
specialized type of lending that we do.
And then as soon as that started
started to gain momentum, I said, "We
need to diversify." And why did I say
that? Because
at the time at towards the end of 2020
was the first taper tantrum. That's when
rates also spiked from the 10-year went
from 1.4 to about 3% in a period of 4
months.
Which killed about half our pipeline and
um this set us back a lot. We said,
"Okay, once we get this thing off the
ground, we need to diversify because we
can't be a one-trick pony cuz if rates
spike
we can't you know, we let's we we can't
uh afford to potentially be knocked out,
right?"
And thank God we're in a position that
rates didn't spike for almost
talking about 22 from 2014, 8 years
later.
Which gave us enough time to
really build out the business properly,
diversify, add a number of verticals.
Which actually helped offset the uh drop
in origination income that we that we
saw during that 3-year period.
>> How does your your belief in God, uh
your observance, your connection to
Judaism, how does that, you know, work
in tandem with with the with what you do
every day professionally?
>> Without the Emunah U'Bitachon, which is
>> Faith, the confidence in God.
>> Right. Um
like
I don't see how I would have been able
to get it done. I just I know that
Hashem is on my side, right? And it's
just a matter of, you know, figuring out
and navigating what we need to get done
in order to achieve it. And then
sometimes also
when we hit a certain challenge, it's
almost like maybe we should maybe maybe
he's doing us a favor and
that's not a direction we should be
going down a path that we should be
going down.
>> Do Do you incorporate Torah learning
into your day-to-day?
>> I'm I'm very big into Torah learning. Um
I'm a big proponent of it. I personally
have take I don't want to I don't want
to say that I learn a ton, but I've I've
increased my
my Torah study
uh
considerably over the past 2 3 years you
know relative to what I was doing prior
to that.
>> What Why? What happened?
>> I don't know I wouldn't necessarily say
it was a specific event or or trig-
something that uh specifically triggered
that. I just I I noticed that it it was
definitely helpful in my life. I
wouldn't necessarily
I'm saying it was very over- overall
very helpful in my life. I wouldn't
necessarily say it helped my business
life per se.
>> Sure.
>> Uh maybe it did
as a byproduct, but just overall just
way more level
Listen, in life
right?
You want to go down the right path.
And
from time to time people sometimes get
diverted from that path make
a little too far to the left, a little
too far too far to the right. I'm not
talking about politics right left. I'm
just talking about the the path.
>> Right.
>> The path.
And Torah study for sure helps you stay
in that lane
way better than anything else you could
do.
Any other mitzvah you could think of?
Stuck out what you know what we're big
on.
>> kindness, to go
>> those things are all important, but I'm
saying in the game of life when you want
to stay in the right path, there's
nothing that's going to help you stay in
that path uh easier than
uh to uh more effectively than Torah
learning.
>> What brings you happiness in life?
>> Okay, so happiness in life is I would
say it's just uh family, being with
family, being with my kids. Um
that's another lesson by the way that I
learned later in life. In my early work
life I was working like a dog and I was
one of those weekend dads that basically
just saw their kids on Shabbat and like
Sunday and half of that time I was
you know,
Um so I made a real effort to be more
present
in the house with the kids over the past
several years, 5 plus years now.
And uh that definitely made a big
difference. That's for sure number one
on the list.
If you're talking about from a business
perspective, it's what I call mind
expansion.
>> Right?
>> I don't know what that means.
>> Mind expansion is when when you
have an epiphany moment in your head
where you
can now believe that you can be in
reach a certain status.
>> So mind expansion?
>> Yeah.
>> Oh, when you expand your
>> I can I know I can make
I can make X amount of money. I know I
can start this other business. I know
uh I can do XYZ and now
you start formulating that plan in your
head of how you're going to get there.
So it's that it's almost that epiphany
moment that excites me. It's like, "Oh,
we're going to go we're going to go
we're going to start doing this now."
>> What's your favorite thing in the whole
world about being Jewish?
>> You're part of an exclusive club.
>> What What are the rights to that club?
What are the benefits of that club?
>> It's unclear. From a business
perspective, it's been extremely
helpful. It's been extremely helpful
because for the most part everyone helps
out each other out. Like I said, you're
talking in you're talking in shul,
you're talking about guys in the
neighborhood, kiddush, whatever, and
things definitely come out of it.
There's no question. If you're just
talking about overall, I mean like we
have emet, we have the truth. We're the
we're part of that winning club. We've
we we're where it's at and there's
there's no doubt in my mind that it's
the it's the best club to be in.
>> Looking back on the last two decades of
your career, it's probably more than two
decades if you're hustling at like 10.
But um what's your biggest regret?
>> When when my brother and I started the
business, right? We again, we were both
very young.
At after that initial 6-month period,
things really started to take off.
And you could say there were certain
characteristics that
um that I had that still needed to be uh
>> ironed out. And ironed out.
>> And eventually
you know, we figured that out. I don't
want to say I figured everything out,
but for the most part uh the major
issues.
Um and I wish I had learned I wish I had
the opportunity to almost like
have that experience
uh prior to starting the company.
Um but it is what it is. It is what it
is. We you know, we jumped into it and
um
>> It's part of your journey.
>> Yeah, exactly.
>> When you hire or when you look for
partners,
what's the most important quality to
you?
>> Competence.
>> But you don't know that right away, you
know? They're sitting in front of you or
You can tell?
>> I I don't want to say I can tell, but I
we've got we've gotten much better at at
interviews and vetting people.
Uh but for sure competence, like I said
earlier, work ethic.
>> Mhm.
>> Uh and uh just just from a personality
perspective, just driving well with the
the the people
and the culture within the company.
>> You know, most of the people who watch
and listen to this podcast are just
starting.
They may be involved in their first real
relationship. They have their first real
job. They're contemplating their first
investment.
As somebody who's been there and done
that, could you give them one or two
pieces of advice of how they can be a
little bit more successful, give
themselves an edge?
>> Jump in.
Jump in and don't try to overthink,
don't try to overcalculate, don't try to
get every single detail up front. If you
have enough of a game plan, jump in, do
it, and you'll figure out the details
along the way. You'll make some
mistakes, but
>> And what happens if you jump in and it
doesn't work?
>> Because you need to rethink your
situation. What What put you in that
What
led that to happen? What put you in that
position? Was it because you didn't have
the proper game plan in place?
Were you missing big pieces of the
puzzle. You know, you have to have
conviction, right? If you know you have,
like I said earlier, the secret sauce or
the winning formula,
go for it. And if it doesn't work out
for whatever reason, then maybe you
didn't have it and you just need to
rethink your situation internally and
you'll figure things out before you
potentially get it done do it again. And
I would I would tell you in most cases
it works out.
>> You're going to be okay. Don't be
scared.
>> Yeah, just go for it. Go for it. And go
for it at a young age, too. I'm not
saying do it when you're
20 26.
But don't wait till you're 40 50. You
can you can you can don't say you're
going to wait till I'm 40 or XYZ. If you
know you have it, go for it. Go do it.
>> And and what would you tell this
>> [snorts]
>> young fellow, this young lady, or this
young couple that's trying to figure out
where to land
observance-wise, religiously,
spiritually?
What's a piece of advice that you'd give
to them?
>> You're going to live a much better life
when you have a sham in your life when
you when you when you have the when you
have the Torah
uh when your kids are are growing up in
a Jewish school in a Jewish environment,
there's no question. I've seen it.
There's there's no debate. There's no
Oh, but in under this circumstance. No.
When you have a sham, the Torah, and
your kids in a Jewish school, you're
going to be way way way way better off
and it's not even close.
And my suggestion would be
to
not go for it necessarily in a big way
up front, but grow grow steadily. Now, I
won't say slowly, but grow steadily so
that you build a proper foundation
before you start going vertical um you
know, floor by floor.
>> Beautiful. This has been super
insightful. Really interesting to hear a
little bit about your journey, and I
wish you loads of success uh going
forward. And thank you so much for your
time and for your wisdom.
>> Appreciate it. Thank you so much. Thank
you for having me. Appreciate it.
>> 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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