🎙️ Episode 1: On career pivots, choosing your partner and Jewish responsibility | Jeff Weiskopf

Imagine that you're in the same career for over two decades and then you realize there's no future. What do you do? Who do you turn to? And can you actually pivot? Jeff Weissoff has the most incredible story of deep determination and amazing Jewish values. Listen to his story this week on Jewish Grit. [Music] Jeff, just so we can get to know who we're talking to. Share with us a little bit maybe in 60 seconds or so about your personal journey, like where you're from and kind of how you got to where you are today and then we'll uh jump into your professional journey as well. >> So, I was born and bred in Manhattan in an area called Washington Heights. My father was an immigrant. My father's an actually interesting story. My father came to this country when he was 10 years old. He had very little Jewish education. He went to public school. Somehow my grandparents at 18 years old he was drafted in the United States Army. He kept kosher. He kept shabas somehow and then he went to college. He graduated a degree in mechanical engineering. Married my mother. My father actually only upon his retirement started to learn Torah and during those years he finished shas twice. >> So he finished the entire Talmud >> twice. >> Wow. >> And inspired me. It inspired me to start learning daffy. >> That's like a daily one page a day. >> Inspired me. If my father can do it, I can do it. So now I'm on my second cycle. >> Amazing. >> And some of my children are doing this as well. And I went for one year I learned in Israel. Then I came back to Washington Heights and I learned for five years in Bish. At the same time I went to college at night. >> I actually found that to be a relatively easy experience both in terms of scholastically and and religiosity because I only went with an insular group. >> It was girls and boys but we went together to college at night. We did. >> Where did you go to school? >> Baroo. >> Oh Baroo. >> I finished college. I've been for four years in about two and a half years and really I wasn't so interested. I was doing it to please my parents. I did have ambitions to go into business at that time. You needed a college degree. People did were not as entrepreneurial as they are today. >> And I was taught that was the path to success. You get a degree and you do something. I think the entire United States has woken up that that's not the only path today. And matter of fact, going to college today probably sometimes could be detrimental. I had a number of jobs till I landed in the jewelry manufacturing business which had nothing to do with anything I've ever learned. I learned that business. I became the head of sales of a pretty pretty substantial firm and I sold all the major uh all the major retailers. I was was almost 20 years of that commuting to Midtown Manhattan both in terms of when I lived in the city also when we moved up here to Rocken County. That grew old. It grew old. The industry changed. There were things that happened in my life that I wanted to make a change. There were aspects that weren't good for me in terms of having to travel to Las Vegas a lot in terms of dinners. Fashion business is not an easy business for an Orthodox Jew to conduct themselves properly. And it got worse as time went on. It forced me to start thinking about what I really want to do with my business career. >> That's amazing. You had two decades in one particular, you know, >> almost two decades. Yeah. >> And then you Part of it is also part of it also the opportunities didn't come. >> Um I didn't I don't know if at that time in my life I was so thinking of I'm going to start my own thing. So it was a lot of things came together for me in my mind and like everything else and and I if I had to give people uh one of the messages that you uh that you that you want me to give out there is masle good luck. It's God leading you to certain things and things that look detrimental to you are really to your benefit. And I had to make a change. I met my now lifelong friend and partner Serio Roselle. He is today the president of the Chieva Spring Valley as well the president of other schools. He actually had a very established adult care facility business at that time. And we did the tuition for this school meeting parents deciding those that couldn't pay how much scholarship to give them etc. And we headed off. I wouldn't say we were best friends, but we certainly developed a relationship. And I was sitting him with him one night and we decided to go into the real estate business >> together. >> Together. And the biggest mistakes that I made in the real estate business were the original deals that we made. And and they burdened us for quite a few years, but it got us off the ground and it was the way I learned the business. Both of us never dreamed we'd have the success in this in the business that we did. And like I said, I owe it to nothing but good masle. and he also was the basis to show me how to take that responsibility to the cl seriously >> in terms of communal work >> in in terms of communal work. Today our office is probably the central location for many many different charity causes rabbis coming to visit yeshivas using our offices but I owe a lot of that to him to showing me that this is what we do with our time. I don't think he he ever sat down and said this is what we're going to do. It just evolved. I had been commuting from up here in Rockin County to the city on a bus and anybody that's done commuting knows this is the most aggravating experience you can have especially to New York City and on a good day door to door I had a round trip of 3 hours 20 years ago there wasn't as much opportunity for people to have business locally it it wasn't in vogue to work from home or to have a home office um it's really evolved in the last 20 years that concept that today is taken for granted and So I had this extra 3 four hours a day and to my wife's credit my wife suggested why don't you go learn >> study Torah >> study Torah and I had been learning at night at all times this was sort of a strange constant to me you want to start in the day instead of going to work we're going to do this okay talk to my partner about let's let's see he says yeah let's do it someone directed me to the local colo ko is a is a group of people that devote their lives to learning full-time >> Torah Torah from the morning to night >> from morning to night. >> How do they sustain themselves? >> Their wives work and people support them. It's a privilege for people to support them. >> It's a combination. And not that I was going to do this full-time, but this particular group was in a place where also businessmen learned part of the day there. And so I walked in day one. To this day, I'm sitting in the same place. >> Wow. >> Now, we we we built a new building since then. So, it's not the physical same seat, but it's the same group, same everything. Changed my life. How many years ago was this? >> This is 20 now 21 years ago. And it changed my life. Why did it change my life? Because when you start off your day engrossed in Torah study, you're a different person. And you're a different person now when you go out in the world and you interact with the world. And I've learned that who you are, how you think of yourself reflects in how people look at you and how you give off. Not only that, I created a business in a business environment in a orthodox Jewish setting where people behave and speak properly. Yes, there are men and women in the office, but they treat each other with respect. There's no flirtatiousness, God forbid. There's no really intermingling. There's no off-color jokes. We people conduct themselves properly. And it's all because we set this tone when we started. And I have learned over time that you can conduct yourself in this manner and it's not a contradiction to being a successful business. So that learning in that colo in the morning changed my life in many many different ways. I I established a relationship with people. I associate myself with this. It's who I am. And I'm associating with people who's who are learning full-time who have very different lives than I do. and they look at me as as somebody who's helping them and so that made a very very big difference. C >> can I just um double click on something? So you you still are going to this colo every single morning? >> 21 years same people. >> How how how long do you spend there? Every single morning >> um between an hour and an hour and a half a morning I'm there half regularly hour and a quarter. >> What do you like what do you study? >> We study Talmet. >> Talmet. >> We study Talmet in depth. >> In depth we we do all the explanations to it. How it affects our present lives. What in the Jewish world we call how it affects the laws that we deal with in our daily lives. It's broad, but it's it's an indepth and you can do in depth when you're not tired in the morning. So, it lends itself to the first thing in the morning. I I'm sitting there with my coffee learning for an hour and a half. >> What time do you get to the office every day? >> About 10:30. >> Wow. And then what time do you leave? >> It varies, but uh 600 6:30. >> My office now is 5 minutes from my house. >> And and currently you do um real estate. What do you do? So now, so now we our my main business is multif family. We own and operate. Now we're at about 10,000 height. It was about 12,000 12,000 and change apartments. It's up and down the east coast. Since then, I've evolved. I have I have partnerships in other businesses and investments in private equity businesses. I have investments. We're also doing private equity. Um, we have a warehouse business. I've done other things. We have some big development going on. >> Can I take you back about 20 years ago? So the sun is setting on your I guess jewelry sales business, whatever it is, and it's kind of scary. I'm assuming at that point you have family and children and you got many things to take care of and you have to find something new. Did you ever dream at that point that you'd kind of be where you are today? Not for one second. >> My wife was working at that time. She had a very good job and that helped give us a little bit of a security blanket. Um, as I said, my partner was willing to take a chance. So that also provided a little bit of a security blanket, but never dreamed never dreamed any of this would happen to me. And like I said, it's masle. >> I I can't stress that. >> I can't stress that enough that there are so many times in your life that you need to open up and see that God runs your life, the life of all Jews and the world. It's a real trick to see that and to realize that you can work very hard. That doesn't mean you're always going to be successful. You see very smart people that don't have any degree of success on any aspect of their lives. You see people who never finished high school and they're billionaires. How could that be? You see people that have great children. You people that don't have as great children. You see people that have good health. People don't have. Now you can say health you can't control everything. No. Everything's the same. Everything's like that. You just have to open up your eyes to it and see it that not anything you do can be controlled. But realize that runs the world that it functions as if it's a natural occurrence and that's the reason you have to work hard. But know that working hard is not necessarily what's going to lead to your success. What's the proof for example and let's take my field real estate. I've had deals where I thought this is a grand slam slam dunk. >> How can you go wrong? And you work on it and you work on you work it doesn't go. And I've had things that okay it'll be okay and it's unbelievable. Like we have times, for example, we refinanced something recently and made a lot of money. My partner says to me, why did we take investors into this and dilute ourselves because you didn't know that this was going to work? The answer is on all this is to recognize that Kajbu runs the world. We're not in control. Do the best you can. Doesn't mean you can't you can't lie down the street and say, you know, nothing's going to happen because he doesn't run the world that way. But know that your success or your lack thereof has nothing to do with your hard work. Which is a point I wanted to make something we said before. Coming in at 10:30 in the morning has no bearing if I'm going to be successful or not. Cuz you work hard. But I work a little more or a little less. At the end of the day, when there's a summation of everything you've done, doesn't make a difference. It doesn't just it's not consistent whether you worked hard or didn't hard, whether the deal works out. And so when you come to grips with that, you realize it doesn't make a difference if you come in at 10:30 in the morning. Are there times that there's an emergency and I have to go in if I have to try? Of course, you have to live your life within normal means, but by and large it's in congruous. It doesn't go together. Fantastic. Can I ask you a question? Do you have like a mentor, someone that you go to in life when you need to make personal decisions? We're not always objective. We just need another opinion. Or someone that you go to professionally when you really need somebody to chime in from the outside. You're not talking about business, you're talking about life decisions. >> Either or. I'm, you know, >> so in business, I'm a little bit past that. Everyone can learn. And yes, I've had business questions from time to time because everyone does. Certainly when I was younger, but now there are some older people in the business world that I've asked the question once in a while. But when you have a life decision of do I take this path, do I do that? Do I put more emphasis on that? Or even as much as when you're in business, people people come at you sometimes. Not that I'm involved in any fights and I walk away from fights and I've compromised fights. But it's inevitable in business and when you need to make decisions, you have to find great people in the Jewish world. I have found personally more elderly people bring a degree of Torah knowledge and life experience together more than younger rabbis. You might say a younger rabbi is more with it. He knows what's going on in the world. >> It's not so. >> It's not so. Real rabbis understand contemporary life. They maybe they don't understand exactly what a podcast is, but they don't have to understand what a podcast is. But I have searched out people who are older, who have seen previous generations, have seen previous life experience, and I find that the most valuable thing to have. It's always interesting to note how our whole life, the Jewish world, is based on what our grandparents, our great-grandparents, our our previous rabbis said and did. Everything in our life is based on that. The best people to have that is those that have the connection to the previous generation. Yes, today there are some some dynamic young rabbis, but they don't always have the mileage that the older people did. I'm not talking people who are frail and can't speak and and and losing their mind. That that's an another that's an extreme, >> but I try to search out people that are a little bit older rather than younger to have that combination of Torah knowledge and life experience. >> Very smart. Do do you think that, you know, as your career has evolved, as your family has grown that your definition of success has changed like from when you were starting out 20 years in and then where you are today? >> Absolutely. When you're younger, you you think about money. Everybody worries. Everybody on their level, they worry. Everybody wants to always make more money. There's a gar a Talmud saying that everybody that has a hundred wants 200. Everybody on their level is is that everyone and every insurance salesman will tell you that you never have enough money just like you never have enough life insurance, right? Everyone always worries that whatever money they've accumulated, it's not going to be enough and when the end it's going to run out. So there's no question about it that you think of these things when you're younger. I I don't care who you are. With small exceptions has to be that people think that way. Everyone on their level, >> right? >> Right. But as you get older, especially as you have some success in business, you realize that it's not the driving force anymore. And don't get me wrong, I want to be successful. I want to make money. Again, like I said, everyone does. But you realize that your legacy is left by who your children are, who your grandchildren are, how they conduct themselves, how people look at that, your relationship with Rabon Shalom, your relationship with your wife. And by the way, I can't say that enough. My wife is a big part of everything here. I mean, we can talk about that separately. And if your wife is not on board with what you're doing and your your outlook on life, it's not going to work either. As you get older, you realize that your legacy is is only what you leave over. The rest is not going with you. >> You can't take the money to the grave. >> No, not even close. My partner's mother just passed away last week. She was 94, 95, whatever. At the funeral, some of the rabbis were talking about, "Look at the family she left behind." Okay, one of them is my partner. >> And these are upstanding Orthodox Jews. and she has 150 descendants. >> Wow. >> Why am I bringing this up? I'm walking out of the funeral with a man who is one of my mentors in communal work. Man who lives in Muny. What does he say to me? He says to me, "Look what this lady left behind." And we talked for a minute as we're walking out. When you go, that's all that counts. What they say about you. Look what he left. whether he wrote things about Jewish life, whether he accomplished things for the Jewish people, if his children behave themselves properly, if they conduct themselves properly. No one says, "Look, that that he's a rich man, he died a rich man." Like, what's the difference? We all fall into the trap of money, especially in the United States as it is today where there's so many different things pulling at you to live the good life, so to speak. Go to a funeral and I assure you that that's the most sobering thing you can do. It's a real wakeup call, right? as long as you're a thinking person. >> What's the single best piece of advice that you think you would give our viewership? Somebody who's maybe in their early 20s trying to figure out professionally where to go build a family. What's the single piece of advice that you would tell them that you think could really help them? First of all, you have to have a wife that's on the same page as you or a husband >> or husband, right? Or husband as far as your outlook on religiosity and your beliefs. If you're not on the same page, it's going to cause problems. Number two, you have to structure your life that you can balance things. People have difficulty balancing. Now, granted, masle doesn't give everybody the same opportunity to balance everything, but balance out your life, your children, your religiosity, your learning, your work. One without the other is going to leave you yearning for something. you're gonna be feel yourself missing something. The most successful people and depends how your your definition of success is are those that have found that balance. >> Can I push you a little further? Just >> Yeah. >> How do you find balance? >> It's a process. >> It's a process. There's you're not going to read a book. >> No. No psychologist is going to write a book and tell you how to find balance. But I think like any problem, think about it first. The first thing to do is if you're already thinking about it, you've already done some of it. It's true. Now, some of it evolves because I don't think there's anybody who's in their 50s or 60s or 70s who says, you know, when I was 20 years old, I had my whole life planned for me and it worked out exactly that way. Your friend has a book says, "Listen to your messages." Everyone has a few messages in life that they have to hear where where God is literally talking to them and listen to them and as things happen say, "Oh yeah, this is my moment." And sometimes you look back and say, "How did this happen?" I've had the privilege of getting to know some of the greatest rabbitic scholars of our generation today. Why? You know, Hashem gave me a little extra money and I somehow the word got out there and I started giving some of that money away. So they started coming and without realizing it, I started to develop relationships with these people. Now granted, I had to have that opportunity for the door to open, but myself and my children know some of these people today. That has to leave an impression on your life. And what these what great people can do is they impress upon you just by the living to a on a higher plane how to live your life. It affects you. If you're associated with very good people, it's going to affect your life. And it can enumerate many people like this that we have the privilege of knowing being in their homes, them being in our homes that makes a huge difference in your life. And the second thing is to realize that life is a responsibility. It's a responsibility to your wife or your husband, to your children, and it's a responsibility to the Jewish people. And especially when you have a degree of financial success, it's all about the responsibility for the Jewish people. It's not about buying another building or making another million dollars. And don't get me wrong, I want another million dollars, but it's not that's not what it's about. It's about giving back. A lot of people don't realize that they too can do it. Very, very few people put themselves out there and go raise funds, organize, step out of their comfort zone and give back. And that's a big responsibility that comes with a certain degree of success, especially now during the war. As you see how Jews come together and how we really are so different than others, how we sing and pray in times of adversity, how we bond together and it doesn't make a difference. More religious, not religious. You know, I at the beginning of the of the war after October 7th, I had the privilege of going to Gaza. We were right outside Gaza. There was a like a re rehabilitation center where they brought in a lot of soldiers just to get a good meal and to dance and sing and to get a breather and take a shower before they went back into Gaza. And this is toward the beginning of the war and we were down there and my son calls me over to meet a group of soldiers. None of them were religious. They were Israeli soldiers. None of them were religious. And my son was who enchanting young man. He was enthralling them, talking to them and he brought him over as my father and one of them asks me why are you here which is a very normal question like what are you doing here right and I told him I'll say it in English I said there's not a synagogue or a Jewish girl school or Kell or yeshiva or any place in America where we are not praying for you every single day and I came to tell you that that you're not alone and every single synagogue in America is praying for you, the soldiers, every day for your safety. And this non-religious guy says to me, "Keep praying. We're seeing miracles every single day." When the chips are down and he's in that tank that he's counting on your prayers and that it it bonds us. And you see you see all types of Jews bond together when times are tough. >> Yeah. When when everything's going great, we're killing each other. >> But uh but it's an amazing thing. I'd love to have a second conversation to to uh I guess revisit your definition of success maybe in a few years from now or maybe before that. Thanks so much. Really appreciate it. >> My pleasure. My pleasure. >> Thank you for listening to Jewish Grit, an 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 oli.org/mentorship. Don't forget to keep listening on Apple Podcasts, Spotify, or wherever you get your podcasts.