🎙️ Episode 8: "From Struggles to Social Media Success: Abbey Wolin on Smart Business & Self-Care

Abby Woolen turns heartbreak into healing and early business struggles into a thriving career built on resilience, art, and strategy. On this episode of Jewish Grit, hear how she carved her own path and now empowers countless of entrepreneurs to do the same. This week on Jewish Grit. [Music] Hi and welcome to Jewish Grit, the Olam mentorship podcast. I have Abby Woolen here with us. Why don't you let us know a little bit about you, your background, and what you do? >> Sure. Okay. So I am the CEO and founder of AW Media Social, which is a social marketing agency that works with, you know, very big brands and businesses. For example, we are the social media agency that supplies and oversees the entire social media department at American Dream. So we are like overseeing all of their campaigns from a social marketing perspective, but we also work with nonprofits. We work with one of the organizations is Yahad which is under the OU and they uh support individuals with special needs. Um and then all the way to like camps or retail businesses and and all different types. I actually just launched something which is really exciting about small businesses and really helping them cuz there are so many times that there are small businesses that need that they're too big to do it themselves and they need a little bit of support like kind of like a little bit of gas in their in their car to get them to the next level. um but they're not big enough to have a monthly retainer to a marketing agency. That could be really expensive for a lot of people. We just launched the accelerator program which is really exciting. And then on on top of that >> on top of that >> on top of that um I'm I'm very passionate about art and Judeica art and my first business that I ever started was called Not too shabby which is hand painted glassware and serveware and I actually ended up pivoting into the marketing agency and helping and supporting Jewish women entrepreneurs. I felt that calling like that it was like deep inside of me that I had denied for like a good six, seven years and I decided this year to bring it back. So, Not too shabby is back as a craft company and we um and painting, you know, hand painted glassware and people have been so excited to see me do art again. That passion, you know, uh those hobbies are so important um so important in bringing like life into what you do. But I think self-care is something that we, you know, lack or we don't give ourselves enough of and um denying ourselves of these hobbies and things. >> You did a lot. What were some challenges along the way to make these transitions because that could be very powerful to people to hear. >> I was a pianist. I was actually supposed to go to a school um you know like you remember fame like back in the day. So in 10 going into 10th into 11th grade I um auditioned and I tried to get into a public school. it was a public school like fame out in Sioset in Long Island and I remember somebody telling me that if you go there you'll never like you won't be from so um it was like a very very um specific decision in my life and I really remember consciously saying no this is the Torah life that I want um but what happens is that when you're multi-passionate and you can do so many different things it could pull you in so many different ways and so how do you actually navigate that and so I had a really challenging childhood and adolescence and my father was diagnosed with cancer at the age when I 6. >> Um, he passed away when I was 11. I was living in the West Coast at the time in California and my mom 2 years later I was 13. My mother my mother remarried. Um, moved us from LA to New York. And now they have we had four five kids. They had four kids. So it's nine of us all together. We're all teenagers. In nth grade I got into bad kid like just a bad crowd of kids. And I remember going into 10th grade and saying those kids are not really the people that I am. that's not who I want to be. And I remember actually like looking around at my class and saying, who do I actually want to be friends with? Like, who do I want to be when I get out of this school? >> And um I made new friends in 10th grade. >> And by the time we got into senior year, they were all like going to like really big colleges. I mean, like one of my friends went to Cooper U. So, um I I was embarrassed to say that I was going to go to um like community college or like even though that's that's a fine place to go, believe me. But they were all going to like really big Ivy League schools. So, I thought to myself, where could I go that would get me on ability alone, >> right? Because I didn't have the grades. So, I thought to myself, "Oh, um, well, I like art and I'm going to be an artist and I'm going to go to art school." And um, so I remember going to the principal and saying to the principal, "Can I get into the art program? There was a 12th grade program. I have to make a portfolio to get into the to the college I want to get into." And he's like, "Well, no, you didn't take it in 11th grade. You don't get to take it as a senior." And I said to him, "No, no, no. I don't think you understand. If I if you don't let me in here, I'm going to apply anyway. So, either you could help me or not help me. And he said to me, "If you if you get permission from the art teacher, then I'll let you in." And I remember I went to the class, I knocked on the door, she looked like Miss Frile, like like mind you, like really frizzy hair, like like a like flowy skirt. And she said to me, she said, "Let me see your work." And I said, "I don't have any." Right. And I and she goes, "Well, did you ever pick up a pencil or a paper, like a paint, anything?" I said, "No." >> Oh gosh. and she said, "Without skipping a beat, I'll see you Monday." >> Wow. >> And I got into this class. And I remember like it was there that I like really really found myself. And um I used to always put so much I don't know not energy but like the thought that it was her like she changed my life. But the truth is is that I changed my life because of the decision that I had made. She was a Shalia. She was a messenger and she helped me get to where I needed to go. happened to be I ended up getting into the top art schools in Manhattan like School of Visual Arts and FIT. I think it's that kind of grit like you go through a lot in your childhood and it's it's the decisions that you make. It's kind of like being almost like awake >> to make those decisions, not allowing things to actually turn you or take you. It's saying no, this is what I want to do and this is what I'm going to do. >> Have you had like a a mentor throughout your life? And and if so, like what what do you think the best advice you've ever received was? >> I actually found an executive coach like recently >> who has been very helpful and just really really great. And I think the best mentors that are out there actually help you come to the decision on your own without giving you advice because you're going to fight that advice, right? You're going to you're usually like whenever my husband says, "Oh, blah blah blah blah." I'm like, "No." Cuz like I want to prove him wrong, right? that like I that's how I was built. I was built so many people telling me no that I was going to do it anyways that like that grit is like just embedded in my life. Like I want to prove people wrong. But what I love about what Tani has done for me, my executive coach, is she actually helps me come to the decision on my own. And I think that that's really what >> um makes a really good mentor. >> You've done businesses. What words of advice would you give somebody who wants to start their own business? is you really have to think about it from all angles. Um, you know, we live in the digital age of AI and I would say absolutely work with chat GPT. It's your best friend. I know a lot of people will say don't use AI, it's no, it's a copout. No, absolutely not. It's your best friend. >> Um, I have worked out so many different problems and strategies and ideas with JGBT. Just remember, don't rely on it. It's not it's not your it's not a copout. um you use it you use it with discretion but the truth is is that um you really have to understand your money. >> Okay. Cuz the biggest um downfall for all businesses and even for all personal lives is cash flow is like the money coming in the money coming out and making sure that people are paid. And I think the hardest thing that I've ever had to do in my business is fire people. Like I'm a I'm a I'm a I know it doesn't sound like it but I'm actually like a recovering people pleaser. like I really like no like I really like it means a lot to me that somebody likes me but the truth is is that sometimes we have to have really hard conversations >> and and keeping somebody on staff who's like maybe working because they're not happy but like they're afraid to have the conversation or um they're not doing the work that you need them to do. whatever it is, you're only helping them and you're helping you to find the place that you're helping them find the place that they need to go that they're going to be happy that they're going to be um they're going to thrive and flourish and you're going to help your company grow. >> What do you do for yourself for spiritual? >> So when my mother remarried my step married my stepfather, we were raised very very religious like in the Biakov um world. Okay. um it didn't wear pants, didn't you know, my mother covered her hair. Um but when she married my stepfather, they decided that they wanted to be a lot more modern and they sat us down and they said you could, you know, go to public school, do what do whatever you want. And I think she did that because she had a ton of teenagers who were like questioning life. They had just lost their parents. People were angry. Like I had siblings that I mean we were all angry. Um, and I think the way that she just like she felt like if she put more restrictions, it would um have like a like a a bad result. And so she let us have that freedom and I really like you know at the time I loved it like I I >> You weren't confused. >> No, I was I was No. So I was questioning. So like for me it was like I wanted to wear pants. I wanted to wear short sleeves. I wanted to wear tank tops. I wanted to wear bathing suits. Like I wanted to be in that modern world. What happened was is that um I ended up in Hank Hebrew Academy of NASA county and in that school it was an NCSY school. So um for those who do not know NCSY is a program under the OU that is out there for outreach um for public school students and modern Orthodox students and they have um weekend shaponim and they are there to really be there to be the answer to a lot of the questions that you have. So like why do I have to cover up? Why do I have to be modest? Why do we keep Shabas? How do I know that the Torah is true? How do I know that what my teachers are telling me are true? How do I know that this isn't just a madeup funny story that we just kept? You know, like so all of these questions were answered for me within my high school years. And that level like stayed with me. I remember when I moved to Paic and um like 18 years ago and I remember being in that community and feeling so like almost like a culture shock like I was like I had told my husband I said I never want to go back to that baso world and I really want to stay more modern orthodox and we ended up in PAS for housing and for whatever whatever it was. It was really hard for me in the beginning. Like my husband didn't grow up that way. So for him it was like it was something that he really wanted and for me it was something that I >> there was trauma behind it because of how I was raised and for everything that I had gone through as a child. So um and I and I remember thinking to myself, I will not have my children have the same experience that I had. And I really worked hard on the education piece to give them those answers. It happened to be that their schools I didn't even have to do so much because the schools in Payic were so good. My daughter came back from with a Biakov high school graduate with so many answers on her own and she found her own path her her own way. But um for me it's like I have this like such a strong connection with God. Like I just I do like I feel like I'm so tapped in because of you know what I went through but also knowing that every single hardship has brought me closer to him. I I know a lot of people like would feel like angry and and betrayed, but for me it's like no, like this I'm in this world. I got one life to live, one. And how am I going to do it? And um I believe so strongly that it happened. Like I I And when I mean it happened, I mean our Jewish history, >> like it happened. And if it happened, then it's got to be true. And if it's got to be true, then I've got to do it all. So I really try very hard not to live in the in between but like really taking it in. So like my favorite thing to do like every week is baking hala. Bacon kala to me is like the time that I can really tap in. >> I I try not to work on Fridays. We have a rule actually in the company. >> Um that like if you have to do work you can do work like get your work done but like I don't want us taking meetings on a Friday. Like if we have to like I think we've had to maybe on like in the six years that we've been in the company maybe five times >> on a Friday but like I want them to bring in Javis. I don't want them to worry about deadlines on a on a Friday. >> Beautiful. That's so >> and that's really important to me >> and I think it makes so much sense that you're saying that the kala because it's it could be it's the creative aspect. It's using your hands. It's it just talks to you. >> Yes. And you can talk as you're making the kala. I just like talk to Hashem and I really just I take that time for myself. I do try. It's very hard, but I do try to bring in Chabas like at least 10 minutes early. Like I really do. Sometimes it's like right out of that cuff. Um, but I really really try and you know I think I think it's like just you know you as I said before you kind of like have to be just awake like you have to be intentional like what do you want your life to be? >> What makes you proud to be a Jew? Like when you think about Jewish people, Jewish life, what what brings you joy and pride? >> I love our grit. Like I know I know I well I know that we had I had talked about our history but it's true like because if you look at all the different stories within the Bible women save everybody all the time. They're always like hidden. And I love that also about women is that we don't have to be loud. We don't have to be like in your face but we need to own our truth and and really um >> when we own our truth we own ourselves and we own our mission in this world >> right? We all have a mission in life. >> Yes. >> Okay. We're here for a reason. >> Um not always do we know what our reason is. Like I wouldn't have known. I mean like literally I figured out like what I'm supposed to do like within the last couple years, >> you know, and then you and then you have the hard task of actually doing it. >> That that is definitely uh a beautiful way to see Jewish grit. And uh I really appreciate you coming down and my pleasure >> being interviewed. and this has been an awesome conversation. Thank you so so much. >> Thank you for having me. >> My pleasure. >> Thank you for listening to Jewish Grits and Olam 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/mentorship. And don't forget to keep listening on Apple Podcast, Spotify, or wherever you get your podcasts.