Preparing video...
0:00 / 0:00
🎙️ Build It, Sell It, Repeat - Shai Stern - Episode 46
6 views
Shai Stern is a serial entrepreneur. He has built and sold multiple companies — not because he had a grand master plan, but because he knew how to spot an opening and "go." In this episode, he shares: ✅ How to spot the next opportunity before you feel ready for it ✅ Why you should treat the Jewish community as a growth strategy, not just a support system ✅ How to pair hustle with faith so ambition doesn't burn you out ✅ Where to actually bring your challenges — instead of carrying them alone Don’t waiting for certainty. Spot the opening, take it, and let the rest follow.
Categories:Torah
Comments
Transcript
Auto-generated transcript. Not time-synced to the video.
You know, enthusiasm,
it's contagious.
When I sat down to talk with Shai Stern,
his enthusiasm, his love of life, his
love of success in business, of building
companies and then just flipping them
and starting new companies was only
paralleled by his incredible, deep,
amazing enthusiasm for Judaism and for
Jewish people. Find out Shai's
fascinating journey this week on Jewish
Grit.
Welcome to Jewish Grit. This week on
Jewish Grit, we have a really special
treat. We have a wonderful, amazing
human being all the way from Muny, New
York. Shy Stern, welcome to the podcast.
Thank you for having me. You know, this
is the first time we actually met and we
chatted before and I'm really I'm seeing
a lot of great things I like about you.
Share with me a little bit in like 90
seconds your journey like where did you
grow up? What did you where did you
learn? What did you do? How did you get
into the professional world and where
you're at today?
>> Okay. So, that's not going to be in 30
seconds, but
>> I'm trying to limit you here.
>> You know, I I've been blessed. Um just
uh a journey that makes no sense. Um so,
I dropped out of Yoshiva University. I
did go to college. I really didn't have
any interest. I couldn't sit still.
Preferred shoveling snow or working with
my father than jewelry business. And I
loved selling and cultivating
relationships. So I got an opportunity.
The the dean of my high school, the
Russa, his name was Haskman in Tar
Academy. And he introduced me to the
Carfuncle family who gave me my first
opportunity. And um I worked at American
Stock Transfer for a couple years. And
then I worked in the business that they
acquired called ASD Stock Plan and
learned a lot about the way plumbing and
services um worked for publicly traded
companies. So in 2002
uh myself and my partner really a
brother of life um Seth Farman and I we
co-founded a company called Vintage
Filings to compete in the SEC filing
edgarizing printing space and um had a
great time building it. We grew it in
five years to 5,000 clients. Um, and
then we sold that business to Pier
Nuzwire's parent company called United
Business Media. And then we said,
"What's next?" And then, uh, we met with
another good friend of ours called Isaac
Mueller, um, who had a small
incorporation company in three states.
It was called the Incorporator. And we
said, "Let's partner up together. We'll
get it to all 50 in, uh, in less than 60
days." And then we built that business.
It was all just amazing how things
unfolded. We built that. We sold that to
uh, to Walter's Clue. Then we went into
the background check business. And that
was a moment where we called up on the
same client said hey we now want to go
into this solution and they go okay and
we got a great young guy who I knew his
older brother um so Ari Rdman um was
living in LA and we said hey could you
come here and be our sales guy and then
he did a great job and he became the CEO
and the business was literally um on a
great trajectory and then co came the
business you know was like 90% down and
and we thought we were in a lot of
trouble um that was a great moment I
thought at the same time I was running
another company called Checkal um that I
ran for 15 years. I was in the payments
business. So when these words were
coming out about an essential business,
PPP money, I had two businesses that
were about to fail. And while I've been
seriously lying in bed sick as a dog, my
wife was giving me a camel back to drink
out of because I couldn't lift my head,
praying that my breathing would stay
well. We had to climb out of that. And
then Bashem, thank God, just amazing
bounces and friendships that just
evolved and people that showed up to
help. Then both businesses, you know,
continued to to go. And then I left
Czech Alton um this past August after 15
years with a burning desire um to open
another business. And uh I I looked at
it and I said you know this this process
of finding a solution being narrow and
saying I could do eggizing go get it and
then build it sell it and do it again in
these different things. Well today with
great technology and a great
technologist great developers you can
build an AI platform where entrepreneurs
and SMBs can come and they can buy seven
eight different solutions out of the
plumbing the orchestration of their
business and they can focus on selling.
So, um, a great friend of mine, um, from
the fintech space, Jeremy Balkan, who
runs a company called Today Pay, um, we
were meeting up and he goes, "Man, I got
a great guy for you, Alicia Herman.
Great Jew lives in Parkland, Florida."
And we met up and, uh, Alicia was at
tech was working technology, marketing
tech at HSBC for a dozen years, and we
connected and we partnered up and we're
now building a company called Gotavi,
uh, G- A VI. And the way that that name
came up, and then I'll take my 30 second
pause. Um, the way that the name came up
is the funnest thing of all. You know,
my kids, we were sitting on the table
chatting about the name on the family
chat. And the kids said, "Well, pups,
you always say, "Let's go." You got to
have a go in there. And then others were
saying, "Well, the other companies were
called Vilings, VCore, Vtock, V Chat.
Put a V in there." I'm like, "Ah, VGO."
Like, "What am I going to?" It didn't
sound right. Then I woke up in the
morning and I go, "Wait one second. Go
means histados. It means effort. That
that's our job. We got to get up in the
morning. We got to go hustle. We got to
go to work." But tavi I said means bring
forth. So I said look at 51 years old um
I said I one thing is incredibly clear.
You could work and you could be
unsuccessful. You could barely work and
you can be successful. The results are
all up to the boss upstairs. So I said
look I'll do my that's the goal. I'll do
my efforts but tav I got to pray to
hashem upstairs and he's going to bring
forth the blessing onto the business. So
we went with that and that's the name of
the company
>> and here I think that goavi is like some
technology term or something like that.
>> That's it. And we we advertise that
publicly on our website that this a
Jewish combination of two words and
actually today's do discusses about how
words come together. So it's interesting
how we just came up with that popped in
and
>> are you not concerned to advertise like
your Jewishness on your company?
>> I love being a Jew. It's who I am. I
advertise it. I write on my LinkedIn
profile. Grandson of Holocaust survivors
and proud uncle of Jewish soldiers. So I
am as proud uh to be a Jew and I wear it
all out there. Um it was actually
interesting. I was um we were in Israel
October 7th and when we came back I uh
like all years I would go straight from
Sukus and I'd go now to this great
fintech event in Vegas called money 2020
and I've been going there for all these
years and I walk into the conference
where my yam and all my friends
colleagues in the industry they seem to
go shy we know we feel so bad you know
the right words that people are saying
about what's going on in Israel and I
looked at them and I go you know I
appreciate your concern but let me tell
you a little secret they go what's that?
I said, ' Let me tell you the end of the
movie. They go, 'What's that? I said, 'J
win.' And they go, 'What do you mean by
that?' I said, 'Well, Jews win. Like, I
mean, look at history. We're not going
to lose. So, there might be a lot of
pain. And there is and there has been
tremendous pain over these last couple
of years. And over our history, there's
been tremendous pain. I said, but we're
not going anywhere. We're going to win.
It sounds like in a good way, you're all
over the place. Um, one business, the
next business, and probably thinking in
the back of your mind, what's my next
move? That's probably how you live your
life. C. Has your definition of success
changed like from when you were just
starting out working for that initial
company and then doing stuff on your own
and then moving to the West Coast and
then coming back? Like is that part of
your your your journey of success of
what what you need to be successful or
is that just been a stagnant a static
type of success is success and I'll just
plug in the pieces?
>> I love the question. I've been
incredibly blessed by having great
rabbis around me the last 20 plus years.
too. Early on, you know, when we when
Seth and I started vintage filings in
2002, I had an opportunity to hear about
Waxman, Mafry Waxman speak. He's a rabbi
ami where I live now. He's a Russia
Shiva. He's an incredibly well-known
speaker um and incredibly dynamic and he
he came out to the five towns to speak
um as a benefit for someone's health uh
who's going through a tough time. and I
went to go hear him and I had known of
him because when I went to camp years
ago, Sleepaway Camp Manov, he was like a
legendary figure that would come um as a
youngster. Um so I went to go hear him
speak and I was blown away. So a couple
weeks later, we were living in Cedar
Hurst in the five towns and my wife's um
great a passed away and her grandfather
living in Muny at the time was sitting
Shiva. So she goes, "We got to go out to
Muny." And I said, "Look, if you're
going to go to Muny, I just want to make
two stops. I want to go to the rabba,
the grand rabbi of the square. And two,
I want to meet this rabbi waxman. Um, I
heard him speak. I was so inspired. So,
my wife and I cold called the yeshiva.
I'm a very I'm a really good cold
caller. And um, today the world has
shifted. A lot of folks don't even know
what cold calling is, but called the
yeshiva and his right-hand guy, his name
is Mosha Nusen, um, spoke in Yiddish,
not a word of English. And today, I can
get along rather well in Yiddish, but at
that moment I was struggling. So, my
English was my Yiddish was probably
worse than his English, but we were able
to communicate that I wanted to meet the
rabbi. And my wife and I went down to
meet her by wax in his home. And I asked
her by waxing the following question.
And I think this is probably the most
pivotal question of my entire life. Um,
I asked her by wax and I said, "Look,
um, I know the right thing is to me to
go ahead and to learn Torah every single
day. And I know that I have to, and I
know that I want to. I just don't know
how to go do it." So he said to me, he
goes, "I don't know what you could
afford at this time, but when you go
back home to the five towns of Cedar
Hurst, make some phone calls and find
out who is the number one, who is the
number one Torah scholar in your
neighborhood and call him and say, I
want to learn with you every single day,
seven days a week. Tell me what time
works for you. You got to work it out
and how much can I pay you?" And you got
to pay him. You got to be invested in
him because you seem to be a guy who
cares about being successful
financially. And two, he needs your
money. And so therefore, he's gonna be
invested in you and you're going to
benefit because you're tapping into
someone who's sitting in yeshiva, who's
growing in Torah. Um, at that moment, I
took that advice. Now, there are many
pieces of advice over my life I didn't
take, but the blessing of that one was I
actually listened to it. So, it's so
interesting to see how you have this
incredible appetite and passion for
building businesses, but you also have a
huge appetite for studying Torah. Give
us give us what you learned just one
nugget of what you learned about raising
healthy children.
>> Um, so it's it's a work in progress. It
it's a real work in progress about how
do you work with your children? How do
you understand them? And how do you
don't expect them to do the things that
you do? Meaning, I'm a very rigid,
regimented
guy. Um, and I love being productive.
Now, that productivity doesn't typically
match the the mind or the behavior of a
teenager, especially today. Um, and it
doesn't necessarily match a young
married person because the man that I am
today at 51 was not the man that I was
at 20, 30, 40. Um, so being able to say,
well, they're kids and I was once a kid
as well and my father gave me a lot of
rope held me to a very strict standard,
but I had a lot of rope and how do you
try to be a little bit more patient? um
to and my kids are are they're you know
they're they're number one they're
they're more or less very similar but
they all have their unique beautiful
qualities and I have an oldest daughter
who's 29 is 17 um I can't say there's
much in common between the two of them
except they're both last name a stern I
mean they were raised literally 12 years
apart so the the differences in the
different challenges of a 17-year-old
today are different than one who was 29
and was raised in LA it's just a
different different life but I try I'm
trying to be slower more. I'm trying to
be more accepting. Um I'm trying to um
not be um demanding that what I do. And
then a lot of times what I've been
taught is that sometimes when you take a
step back, they actually fall into line
um by them seeing the model of what
you're trying to trying to structure for
them and what you're trying to teach
them.
>> Talk to us about like you know who Shai
Stern is in relation to Ami, the Jewish
people.
>> I love every Jew and that's something
that I am very proud of. I I to me I
love Jews that are secular. I love Jews
that are in Israel which is a very
unfortunately is a very polarizing
environment. Um I tell my friends in Tel
Aviv who are secular. I said I love you
and I tell my friends who are inim I
love you and if you come to our weddings
and our simas you got those who are
non-religious you have those who are
modern orthodox and you have those who
are and we all hold hands and we all
dance together. Um so I love the Jewish
people. I always have. Um and and I've
been blessed to be able to help out in
in a variety of ways and I love doing it
and I always dive into Hashem that I
could do more. Um at times I you know
you have to balance as to the right
order of who you're helping out with.
And that's a really that's an art um and
a science that evolves with time as you
ask questions. Especially as you know
someone like me that I I fight impulses.
So um I don't think too much about
whether I should give this amount or
that amount. I usually give more than I
should. Um I don't regret it. It's just
who I am. The Jewish people I tell I
tell my friends I said you can't tell me
a negative word about our people. Any
one of them. Our Jewish people are the
most be we're the most beautiful nation,
the most beautiful community. Um it's
it's fascinating. You know I was
recently um for entertainment purposes.
My wife and I, we went to Rockland
Kosher on a Saturday night before Purim.
>> It's like a big kosher grocery store.
>> It's a big kosher grocery store in in
Munzy where 100% of their clientele are
acidic 100%. And I love the energy. It's
before pur and this it was a Saturday
night. I said I literally just want to
go there to see just like how the Jewish
people get ready for this yiff. It's
amazing. So when I go there and I said
to my wife, I say, you know what's
amazing? This place is completely hidic.
That means that say 60 70% of them are
not producing an income. They're not
working and they're being studying
Torah, studying Torah, teaching, they're
being they're not professional business
people in the way that we would define
it, but yet a 100% of them are online
and 100% are walking out with groceries.
And then you wonder how is that? And
then you go to Israel and you go, how is
it that our people have hospitals,
medicine, technology, Torah, the amount
of giving, you know, that our people
naturally give? My my good rabbi may or
you did just got out with a new book
called The Power of the Giver.
>> Yes.
>> The book is so inspiring and his classes
every single morning are so inspiring to
go at it to say that life's not about
us. You know, my father was the most
giving human being I ever met. Um wasn't
a wealthy man. What he had he gave. What
he didn't have, he gave. And he gave of
his time. He gave endless time. He had a
247 job to listen to people, to give
love to people. I'll tell you you know
when my grandfather passed away who was
the hero of my life my grandfather my
zidi was a hero of my life and this
story resonated with me I'll never
forget it and uh my grandmother is
sitting shiva it was the first time in
my life that I experienced loss I was 17
years old and it was so shocking um and
a woman comes in to pay a shiva visit to
my grandmother
and my grandmother goes I'm sorry I
don't recognize you and uh she goes no
you you might but you might not but she
says I don't know if you remember you
and your husband come down to Miami
Beach to go to Crown Hotel. It was one
of the hotels back in the day. Um and um
and one day when you stepped away from
the table,
>> your husband said to me and said, "I was
your waitress. I was your server." And
my your husband, so my idea said to this
to this girl and said, "Um, are you
Jewish?" And she goes, "Of course." And
he says, "Well, what school do you go
to?" And the girl says, "I go to public
school." Um and he goes, "Well, why
don't you go to a a Jewish day school?"
And she said to my I I can't afford it.
My mother can't afford it. My mom was a
single mom, whatever it was, and can't
afford it. And my grandfather said to
her this, I was there witnessing the
story. And she says, "Your your husband,
your sad, your grandfather said, if I
pay for you to go to Jewish high school,
you know, would you go?" And she goes,
"I'll go tomorrow morning." And he
looked at her and he said to me, "I'm
taking care of your tuition." Now, my
grandmother never knew that. Never, we
none, my father, nobody knew that story.
And this woman flew in from Miami Beach
to pay a shiva visit to tell us that now
no I'm married married a orthodox
orthodox kids because your husband your
grandfather changed my life. Those
stories they go into your soul and when
you see just go to Israel or any Jewish
community and you see what's going on
before any holiday. The pride that we
need to have about our people is just
it's magical.
>> I love the energy and I love the love.
It's really special to see that and I
think we don't appreciate it enough. We
need to take time just to reflect about
it and think about like how special we
are. We have challenges and we have but
one at the end of the day we're amazing.
We are the most incredible people. Two
after October 7th we went back to Israel
for Purim. So when you were going to
have the day of Shushan portal and the
day before my girls we were in Israel
and uh my three girls said to me at the
time um my three single girls and they
go um let's go to Benrock you know on
the port let's celebrate poor Benro. I
said, "That's fine. We can go there.
Before we go to Benrock, we're gonna go
to Telos Shamir Hospital." And they
said, "What's that?" I said, "Well, it's
a hospital for the wounded Israeli
Kayim. We have to go there. We're going
to go." They go, "Do you know anybody
there?" I said, "I don't know anybody
there." They go, "So, why are we going?"
I said, "Because they're our brothers
and our sisters." So, we went to the
bakery. We bought trays of ragal of
pastries. Um, we went down to Telles
Hospital and we walked in and they go,
"Why are you here?" And I said, "Because
you're our brothers and sisters. We want
to bring you Michanotus Pur and uh we
spent a couple hours there. It was
unbelievable. You have a microphone in
front of you and potentially a message
that could reach 70 or 80,000 of our
students and young professionals across
the globe. People who are trying to
figure out how to live their lives and
what are the best things they could do?
If you have 90 seconds to tell them
something, what would what would you
want to tell them?
>> Three messages. Number one, love being a
Jew. Just love being a Jew and what it
all stands for and know how much Hashem
loves you. That is number one and work
to what that actually means. What it
means to love being a Jew and how much
our boss upstairs, how much Hashem
actually loves each and every one of us
in infinite ways. Two, when it comes to
business, hustle.
>> Go out there and work. We didn't talk
about business.
>> I know.
>> And I and I love working and I I dislike
wasting time and know that if you feel
you are talented, know that your talent
is that much greater. And if you feel
you're struggling to find out what your
talent is, just go. Don't let anything
or anybody or any inner hold you back.
Because as you go and as you put forth
efforts, the boss upstairs has endless
capability to bless you in avenues that
you never could have dreamt of. Three,
um when things go hard for you, just
know that Hashem is pushing you to work
on yourself to be better. Hashem is our
forever loving father. He doesn't do
bad. He doesn't want bad. He doesn't
give bad. He only wants to give good. So
when there is a challenge in life, and
we're all going to have them. Nobody
will escape a challenge. I have them. I
had them. I will have them. That's just
life. But when you have them, know that
the greatest um
the greatest ability that you will have
is to go to the source. There's one
address, there's one Hashem, there's
great books and there's great rabbis and
there's great lessons. And to go tap
into it because then you'll see one day
and you say,
>> "I got out of that one and where I ended
up was so much better than I could have
ever have dreamt." Wow. Sh. Thank you so
much for your time. Thanks for your
energy. Thanks for the messages.
>> I think anyone who watches this is going
to be blown away. So, thanks for taking
time out of your very busy schedule cuz
you're a doer for coming here and
contributing.
>> It's an honor. Thank you for listening
to Jewish Grit, an Ol mentorship
podcast. At Olam 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 olam.org/metorship.
Don't forget to keep listening on Apple
Podcast, Spotify, or wherever you get
your podcasts.