Hilary Jay on Downsizing Without Losing Your Legacy

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0:35Founders Forum is a radio show and podcast where entrepreneurs share their journeys, reveal the stories behind their successes, and the lessons they've learned. Join Mark and his guests for a mix of inspiration, valuable insights, and a bit of fun. Now, let's dive in. Yeah, inspiration, perspiration, we got it all going in here in the studio. Good morning, America. How are you? My guest today is Hillary. I'll formally introduce her in a minute. But good morning, Hillary. Thanks for being here. Good morning, Mark. I'm so happy to be here. That's great. Great to have you here. So guess what we're going to talk about?

1:11We're going to talk about AI. Why? Because nobody else is talking about it. That's all anybody's talking about these days. And we've talked a lot about it on the show in regard to business uses and what people are doing with the businesses and things like that. But I want to ask you, how is AI affecting you in your life? It could be your business personally or whatever, but where does it come into play with you? I think it's fascinating the many ways that I've been able to personally use it and then the responses that my clients have had toward it as well. As far as my personal use as an author, I've been able to use it to help me with research.

1:51I don't have it right original content for me, but it can very much fast track what I need to find out. And the research, of course, you have to confirm somehow. Oh, absolutely. That all has to be, you know, I actually do have to go to the library and figure out whether those primary papers do have that actual information. But it saved you time in getting there. It saves me a lot of time. It isolates things for me. But funny, just yesterday, I was doing a art installation plan for a client who lives in a wonderful, beautiful house down in Philadelphia. And that's a little outside the scope of your business, I think, right?

2:33No. Not really? Okay. It's totally in the scope of my business. So yeah, no, I do a lot of art installation and curation for people. Okay. Upon moves. Yeah. Yeah. Yeah. So here I am doing this art installation plan and she wants to physically see how I'm going to lay out 40 pieces of artwork on four floors this Friday. And so I thought, okay, well, I'm going to try to put everything into AI, all the room photographs, all the art photographs and have it lay it out. And I did that. And what came back was very professional looking. However, the curation was so not right. The juxtaposition of different pieces of artwork were totally off.

3:20just the choices that AI was making for me. The human element being missing, right? Absolutely missing, plus that whole judgment about really how one piece of artwork talks to another and what makes sense as far as history of work and all this kind of stuff. So curation is still very much a human high touch. Right, got it. So Hillary Jay is our guest today and she's a founder, owner, and creative director. She's also an award-winning journalist, designer, and arts advocate. So some of her business history, which is very interesting, she co-founded Maximal Art, an international costume jewelry and watch company, where she was chief designer alongside John Wind.

4:02Her accessories can be found in the permanent collections of London's Victoria and Albert Museum, Paris Musée, did I say des arts? Les arts de quartier. Des arts de quartier. something like that. Tongue twister. I need my daughter who speaks French. And the Philadelphia Museum of Art. Hillary's writing has appeared in every major shelter publication, including Metropolitan Home, ID Magazine, Gallery, and Arts and Antiques. In addition, and this is how I knew her name, she wrote a weekly column on interiors, architecture, design, and gardens for the Philadelphia Inquirer Sunday Magazine. She's also an author of a book, which is left out, it, but I think it's important to tell.

4:45Recently, she did a book called Woodmere. If you're from Philadelphia, you know about the Woodmere Museum, and it says, telling the story of Philadelphia's art and artists. She was chief curator of the Paley Design Center at Philadelphia University, which is now Jefferson University, which used to be called the Philadelphia College of Textiles and Sciences a long time ago, where she mounted exhibitions exploring the intersection of design, art and culture. She co-founded Design Philadelphia, the first American design festival, which became the business model for others across the United States.

5:17Yet another thing that was created in Philadelphia, right? By a Philadelphian. Hillary has taught professional practices and design business courses at the college level and led international design conferences and workshops. She launched Department of Better LLC, which is her current company, in 2020 to advise private clients, estates, and institutions on the care curation and transition of significant collections and offers design expertise regarding products and spaces. That's a lot, right? That's a lot. That's a lot. You live long enough. You're a lot in a good way. I've heard that. I'm sure.

5:58So am I, by the way. So I get it. So am I. That's why I can say that. Okay. So So let's start at the beginning. So obviously you're attracted to the arts, to writing, to the arts. It's all about design for me. It's all about design and art. And I mean, I grew up with that in my family. My parents were both designers. And were they entrepreneurs as well? Yes, they were both business owners. And so I wasn't going to get far from that tree at all. I mean, I even tried to take over my father's business at one point, but that was in Baltimore. And I thought I need to not be in Baltimore. Do you have siblings, by the way?

6:34I have a sister who lives in Florida and does very much the same business I do now. Oh, interesting. So she's the one who hooked me into this. So it was definitely in your blood all the way around. Yeah, you can't get far. Especially, I mean, I grew up going to art museums. My parents went regularly. Where is she in Florida? Oh, we talked about this, in Vero Beach. Vero Beach, that's right, right, right. On the East Coast. Talking about Vero Beach yesterday with someone. Yeah, yeah. Yes. Um, so, and so my mother was an interior designer and, um, and yeah. And then the thing about shelter magazines, which might be a funny word for people, it's really home and design magazines.

7:10Um, that was another thing that was very much part of my growing up. We were in them all the time. So, um. Your home because of your home. Yes. Because our home. Yeah. Which must've been magnificent. It was pretty. Yeah. Where was it? It was in Baltimore, outside of Baltimore. and the house was based on a California case study house. So it was one of these mid-century contemporary houses, wood and stone and just really pretty and glass, a lot of glass on a lot of land. And so it was very, listen, very privileged. I'm very clear about that. It just gave me a very specific kind of perspective on objects, on things, on artwork and the value of both the artist, the designer, and the stuff.

7:58And you went to school for design? I started in an art school, and I ended up majoring in sociology from University of Pennsylvania because I found that writing is really my best mode of communication. Gotcha. And I bring a little bit of an academic bent to the work I do. Right. You can tell from the book, which is beautiful, by the way. If you have an interest in art, check out this book, Woodmere. Get it at Woodmere Art Museum. Yep, that's the perfect place to get it, yeah. Probably buy it online, too. At Woodmere, yeah, online. At Woodmere, got it, got it. So how did you, so you were a student in sociology.

8:38What was your path to becoming an entrepreneur? So I graduated, I mean, it's a great question. What do you do with sociology degree? I graduated in sociology, and the next day, literally the next day, I thought to myself, off. Oh my God, now what? And so there were a few twists and turns there, but I had met a wonderful fellow in college, John Wind. And long story short, he and I became business partners and both designers of high-end costume jewelry. It was really art to wear. It was the 80s. It was a very different time. So that business was pretty early on. It was early on. So at 26 years old, I had 26 employees and it was a multimillion dollar business and we were doing it in Philadelphia.

9:28And so, um, yeah, it was trial by fire, but I found out early that I I'm good at, um, I'm good at production and I'm good at marketing. Um, I am not the operations person. And so Fortunately, I've found people along the way. Robin Cook, I give a shout out to her for being an amazing president of our company. By the way, you're lucky because I talk to a lot of entrepreneurs, and I talk about this on the show. I'm a graduate of the Strategic Coach Program, which talks about focusing on your unique abilities and delegating the rest. That's one of the things. But you were fortunate to learn that at a young age.

10:08It took me a long time to learn it. It's been trial. Of course. And I'm still getting comfortable with, what do you mean I can't do that? No, I just can't. Right, right, right. That was our other possible topic of the day, saying no. That's a good one too. You've learned to do that. So that business was going really well. That business was going great, but there were all sorts of funny things that happened. Like we had a radiation emergency where we were producing watches and working with antique watches. And the watches, turned out some of them had radium that had been painted on the dials. Wow.

10:44And so we had to do a big recall of product. So talk about challenges. It was out of Neiman Marcus. It was out of Saks. And we took a big financial hit. And eventually we had to basically reimagine how the business was set up. And I opted to move on. How many years were you in that business? I was only there for five years. Gotcha. So it wasn't that long. Five is sort of my sweet spot. Okay, gotcha. You've moved around a bit. So what happened? Where'd you go after that? So after that, I ended up becoming a writer. And the other funny thing about my life, and unlike you, it sounds like, I have had no training in anything I've ever done.

11:29So I just thought, okay, well, maybe I can write for magazines. And I got a great position with now defunct Metropolitan Home Magazine, which was out in New York, and they needed city editors. So I became a city editor in Philadelphia. And you meet everybody doing that, everybody who's got a beautiful home, who loves their things, who are makers. So I met a ton of people, and that led to my job at the Inquirer, writing a weekly column for a number of years in the magazine. And it also led to my writing for pretty much every other home and design magazine in the country. And I did that for a number of years until, you know, technology kind of put that out.

12:10You're making a living as a writer? Yeah, I was making an actual living. Well, I know your name was around a lot back then. I know that. You know, we all know that just because your name's out there doesn't mean you're making a living. Did you write for Philadelphia Magazine too? That was the first. I had a column called Home Word, the last word on home. I remember. Now that you say that, I remember that. Yeah. So interesting. By the way, you said, unlike me, Yeah. My training, music, composition, and theory, and law. There you go. No finance in there anywhere. So I'm kind of self-taught. Obviously, mentors and learned a lot along the way.

12:49Took a lot of courses. I think there's a lot in that. There's a lot in that. But it started out without any training. I mean, I think following your passion, there's books written on that, is important. And finding people who can mentor you along the way is also amazing. Well, we won't get into my story. But it wasn't a passion at first. It was a way to accommodate what I thought I'd be good at and a way to give back, I thought, which I felt more so than in the law to really actually help people. That's so interesting. But over time, when I saw how the business was done and what I wanted to change about that, that's when it became a passion.

13:24Well, I love that you just said that because there's something really interesting about what I'm doing now, which really – Leads us to that. It's much more of an individual endeavor than any of my past endeavors, which were much bigger in some ways. And this is a passion of yours. This is not necessarily a passion, but this is a recognition of a give back that older, generally older people need this sort of advising and stewardship of both themselves and their very dear belongings. So describe what you do. We have a minute before the break. So let's just describe what you do and then we'll come back and talk a lot about that.

14:03Okay, great. So I work in the downsizing arena, but I'm not sort of a broad downsizer or organizer. My clients tend to be those who have interesting collections, things that artwork, belongings, antiquities, antiques. and they are sometimes forced to move or sometimes they just need to let go of some of things. And so I help them steward those things forward. I find the best next home. And that might be through auction houses where I negotiate contracts or it might be with galleries. I have a really broad network. I've worked with a lot of different places like that. But the first and foremost thing that I notice about all my clients is that they care about sustainability.

14:56So getting that into the work is really what's the most important, making sure that their things are taken care of properly. Perfect and perfect timing. We'll be right back after this break. More than 30 years ago, Two Dudes Painting was founded in Lancaster, PA by two college students with a simple mission, to deliver an amazing experience with every paint job. From those early beginnings, we've grown into a trusted team of professionals. However, our original promise remains the core of our business. Quality work on time with zero hassle. Today, Two Dudes Painting is known not just for painting excellence and providing quality service for over three decades, but also for our strong commitment to our team and community.

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16:25We're back on Founders Forum with our guest today, Hillary J. So we share a second name together because that's my middle name, J. There you go. J-A-Y. Anyway, so we're talking about what you do, what you're doing with Department of Better, which is such a great name. Thank you. The thing I wanted to mention was the other day I was invited to be part of a realtor's talk at a retirement community for people who are interested in selling their homes. Makes sense. Yeah, it does make sense. And it turns out 11 million people, plus or minus, are going to be selling their homes or exiting their homes in the next 10 years.

17:05I shared with you, we just went through it. I know. We just did it, yeah. And everyone I know is doing it now. It translates to like a trillion dollars, literally, in valuables. Each person, the realtor went around the room to start, and she said, can you tell me the question you've brought in? Because I'm sure you've brought in a question. To the person, the first question out of their mouth, what do I do with my stuff? I'm overwhelmed with my stuff. So this whole idea of we all have too much, I definitely am guilty. I live a maximalist life. I can reinforce that concept as well. We went through it.

17:42Everyone we talked to is going through it. Everybody says I have too much stuff. Right. And you don't want to just junk it. Right. And you invested in it. Yep. So how do you get the value out? But it's more than that. It's this anxiety. It's this emotional connection that we feel, whether it's a glass that has really no value at all, but you drank out of it when your husband brought it to you or your partner. I don't know, whatever the story is, there's always a story. And I just, I feel compelled to help people through that journey. By the way, you alluded to it earlier, but it's not just what do you do with your stuff?

18:26It's the stuff that you really want, you want to keep. And now you're going into a new space as a designer, you know. So we brought a lot of artwork with us. Right. And most of it is still in storage trying to figure out what to do with it. Call me. But I don't think it's your level of work. Well, I can hang it for you. Well, we have a well-known photographer who does kind of photography with some painting, with some alteration, interesting stuff. We found two places for those were two favorite things we had in our other house. that we did but we have lots other stuff we haven't figured out so maybe i should have you well you know what i mean you're saying it's not my level i work with people's things that they love their things and um installing them properly so that they can continue to enjoy them and designing the spaces so they can continue to enjoy it is my primary uh you know idea um but to your point about finding a place if you don't have where it can go i'm working with one particular piece of artwork right now where the man had a one person show at the Philadelphia Museum of Art years ago.

19:36He's now passed away. This collector has this piece. It is monumental. It is over six feet by six feet. And, um, and the auction market for it has pretty much flattened. So I was concerned about the artist's legacy as well as my client getting the right amount of, of juice out for lack of a better word. So I've been reaching out to museums to see if they're interested in taking the piece into the collection, one of their collections. That's a whole nother journey for artworks. But there are so many places, there are synagogues and churches who will want things. There are individuals. There's a lot of options for what to do with stuff.

20:18That's a great idea. So what's the experience like of working with people that have a lot of emotions tied up in their things? and what's that like for you? Heartbreaking. Is it? It really is. Well, I would imagine there's some joy in it as well. There is. I mean, there's joy when we get through to the other side because it really is hard work. It is. And, you know, some people feel that they can do it themselves and that's wonderful, or they have family members who can help them do it. It is such an emotional journey that, I mean, I have clients say to me, you saved my life. Now, you know that I didn't save their life, but I did get them.

21:00It felt that way to them. It did. It did. And, um, and, and we, and we, we do it together. I really actually care. Um, I care that the outcome is good for, for everyone emotionally, as well as financially. And it's not an inexpensive process. You said this is not a passion. So maybe you wouldn't call it a passion, but it is a, it is a, it's a calling. It's a calling. I think it's a calling. I'm not a particularly religious person, but spiritually I think that's that. Got it. If it were a passion, I think I'd be just writing more books. So what kind of challenges have you experienced in this business?

21:39Oh, there are a lot of them. Sometimes the things we love just can't find new homes, and so we end up donating those, but at least they get donated. Um, yeah, um, I don't know what else it's, it's sometimes harder when, when people are much older and we have to move them into retirement facilities and they don't really want to go there. They've been very active. They've been world citizens. And to come to the end of your life and to look back and reflect on your legacy and to begin to understand what the meaning of your life has been and what you have perhaps come to, it's a big reflecting point.

22:26Listen, I can connect. I mean, we're not at that stage, but we just moved, downsized the home to a first floor primary bedroom kind of situation that my wife needed and left our home of 26 years where we raised our kids. And it's around the corner, so we see it all the time, which in some ways makes it easier, some ways it makes it harder. But it is an emotional journey. I was with a client. I can't imagine the next one. Oh, well, right. I mean, when you get to 700 square feet or less, yeah, from a 2 ,700 square foot house or a 4 ,000 square foot house. But I was with a client the other day who we've successfully moved with her.

23:09And I just went to visit and see how she was doing. And she was talking to me about her books. And I joke that if I don't walk in and see 1 ,000 books, it's not my client. but okay so we're talking about the books and she was saying i i just didn't understand when i reached out to my children and they didn't want any of my books my books that my husband and i had looked at together and read together and made notes together and talked about together and i just said to her carol it's that was your life this they need to make a new life we went through that listen i have i have music collections i have records i have cd you know kids took maybe a few records and all that, but the rest of it is all, you know, and books and artwork and all that stuff.

23:54I know all of it's going at some point or a lot of it's going at some point. And every client says my kids don't want it. It's brown furniture. Nobody wants China. I've taken pictures of the things I value. I have photos. That's really a great idea. You know what I mean? That's how I've handled it. That's a great idea. So if it's artwork, I can still look at the artwork whenever I want. It's not like Of course, it's not like having the painting, but it's like having the painting. Yeah, and you could always, if you're creative, make a new art piece from the collage of all those things or whatever.

24:30You can use that with it. I like that. We only have two minutes. Hillary, if I were asking you, this is now October of 2026. I don't know when people will be listening to this. But if this was October of 2029 and you're looking back at the last three years, what would have to happen for you to feel like that was a successful progression in your life, that three-year period? Oh, sure. Throw me the worst one in the last two minutes. Okay, fine. You're not alone. I do that to everyone. I wish I was that great of a forecaster. But, you know, as a business person, you do try to have some kind of roadmap.

25:07And I've recently, because I understand what my limitations as an entrepreneur are, I've just started to work with the past CFO, it turns out, of Woodmere Art Museum. and working on trying to understand how to really put systems into place so that I can grow the business into something that would help more people and ultimately would be sellable. I mean, I have found by accident that I have managed to sell two, actually three businesses over the years. Not that I've gotten rich on any of it, but I've been able to at least sell it in order to propel the next idea. and that's valuable. You would have to figure out how to clone yourself to some extent because there's a lot of unique things that you have.

26:01I feel like a therapist a lot. I do, and I don't know how you clone therapy. Right. But I do know a couple of really wonderful people who work with me, and they do an exceptional job of hand-holding as well. You continue to work alongside of them and mentor them. It's kind of what I've been doing in my business. Yeah, yeah. We can talk about that. Okay, that would be good. I would like that. Great.

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