261. Jess Feldman Interview: From Wall Street to Dream Business

Jess Feldman 00:00
There's never a right time. I mean, you kind of have to go for it, you know, and you just, I like to say an entrepreneurs basically is his best friend and his own worst enemy within a 10 minute period. Because—

Susan Sly 00:18
Welcome to my world, yeah.

Jess Feldman 00:23
Because you know, you're full of optimism one minute, and then the next, you know, you're just like, oh my god, you know, you just suffer from like, constant fear of like, I could lose it all.

Susan Sly 00:34
Welcome to Raw and Real Entrepreneurship, the show that dares to bring no nonsense insight to those who have the courage to start, grow and scale a business. I'm your host, Susan Sly. Well, hey, what's up entrepreneurs, wherever you are in the world, I hope you're having an amazing day. And here's my question for you. Have you ever wondered, hey, how do I get the courage to actually take that leap and go from employee to entrepreneur, or maybe you've already made the leap, but your friends and family are looking at you like you have five heads? Well, my guest today is literally one of my favorite people on the planet. And we're going to talk about how he left Wall Street to pursue his dream business. And so before we get into that, a couple of quick announcements. Number one, if you have a show guest or you have an idea for a show, go to Susansly.com, I read all of those comments. So please, I'd love to hear from you. And then the second thing I want to say is, with this show, if these are helpful, please do, we would love a five star review on iTunes, Spotify, wherever it is, Amazon, all over whatever the, I heart radio, wherever, we're everywhere, we would love that great review. So please, if the show is helpful, we hope it is, and you know, we'd love for you to give us a great review. So with that I want to get into it. My guest today spent most of his life surrounded by art, and I kind of think life is art. So this is really cool. His parents began collecting in the 1970s just as a core group of today's established artists were emerging. He initially chose a career in finance, because well, why not? Even as his interest in art remained ever present. And how many of you, you know you have that passion, but maybe you're doing something that's not aligned with that passion? Well, after 17 years on Wall Street, becoming a trusted adviser, understanding markets and his clients objectives, he left to follow his passion. And in 2014, he joined his mom to form SJ Feldman Art Advisory combining her 30 years of experience in the art market with his investment prowess. So my guest today is the one and only Jess Feldman, who's coming, I've always wanted to say this, live from New York, even though we're not on SNL. So just thanks so much for being here.

Jess Feldman 03:04
Thanks so much for having me, Susan, on your show.

Susan Sly 03:06
Well, thank you. So we have a lot of young listeners and people writing in and they're like, I listen to the show with my kids in the car. So I always like to start with the very first question. So what was your first business ever?

Jess Feldman 03:20
I guess my first business was selling strawberries.

Susan Sly 03:23
What? I've not had that one. I've had hundreds of interviews, I've never had, okay, okay.

Jess Feldman 03:29
It's pretty random, I know. So, we had a house in Connecticut when I was a kid, and we'd go strawberry picking. And we would, you know, pack like, you know, probably 100 or 200 pints over a couple of hours picking strawberries. And then I would set up a stand on the side of the road. And we'd sell fresh strawberries. It was, it was a lot of fun. It was a lot of hard work. It would be like three or four weekends in May. And we do it every year. It was a lot of fun.

Susan Sly 04:02
So what kind of, what kind of bank did you make selling strawberries?

Jess Feldman 04:07
We made, you know, every week and we made a couple $100, you know. And for a kid that was a good amount of money. That's for sure.

Susan Sly 04:15
Yeah, well, when people are listening to this, depends on time of year, you know, just there's another—kids, there's another business idea for you, you know, keep on listening the show. We have many ideas that come. In Arizona selling strawberries might not be the business for you, but you know, in other parts of the world, 100%. So Jess, I want to go in the time machine here. So, all right. There are, there are a lot of people who listen to the show who are in a career. They're in a professional career. They're one of the 61% of Americans who are dreaming of starting their own business, but they remain in the 92% that never actually do because, you know for whatever reason it's, it seems so risky. Let's go back in time, how long were you actually thinking about leaving Wall Street before you actually did?

Jess Feldman 05:12
It was probably around five or six years. So in 2008, you know, I still loved art, you know, I'd still go out with my mom, and go to the auctions and go to the galleries. If every time I landed, you know, the first thing I do, and, you know, if I was on business would be to go to a museum. And so the interest remained, and we had started collecting, or in the early 2000s, my wife and I, and, you know, I'd see my mom do it for years. And then I just always wanted to, but it wasn't the right time. I just had a kid in 2006. And there were a lot of things going on in '08, '09 with the financial collapse, etc. And so I just kind of waited. And eventually, in 2013, I just started going out with my mom all the time. You know, I started to talk to her about it, I guess, in around 2012. And I was leaving work, you know, middle of the day, we'd go to the galleries, I'd come back, and they're like, where are you? You know, and I didn't really know what to say. But, you know, my numbers were fine at work, I was actually much more efficient. And I just knew that this was it. And then at the end of 2013, I turned to my wife and said, This is it.

Jess Feldman 06:39
I'm going in, excuse me. You know, January 3, and I'm just gonna say, moving on. And so I just left and took the plunge. And I had one client at the time.

Jess Feldman 07:01
And I was like, I'm gonna crush this, you know. I mean, you're very, very confident when you start. But let me just say this, I would have definitely pre announced the, you know, the first quarter coming out of the gates of an IPO. So, you know, you hit the road running, but you know, you hit your first speed bump.

Susan Sly 07:24
What was the tipping point for you? Because, you know, sometimes I think people watch a lot of movies, and it's like the, you know, take this job and shove it kind of moment, or Well, it depends on how old someone is. They might not even know the reference I'm making. But the, what was that tipping point for you that made you say, Yeah, this is it, I'm leaving.

Jess Feldman 07:48
Well, a couple things. First off, my mom at the time had cancer. And I knew I had a finite amount of time to be with her. And so and I thought, you know, I have a finite amount of time there. And if I let this opportunity go, then I don't know how I'd started. Because, you know, what I found, and I think this is important lesson too, is whenever I you know, I talked to a gallerist or anyone that had known her in the business, you know, they had such amazing respect for her, which I thought was, you know, just a major accomplishment. So that was one thing that really kind of pushed me to it. The second one was, you know, I was reaching 40 years old, and I thought, you know, in Wall Street, 40 years old, you're kind of a dinosaur, what's my next act after that? And that's better than I start now and just go for it. And those were kind of the two you know, things are really pushing me. I also had a very good friend that said, you know, if you can spend this kind of time with your mother you know, you'll have no regrets. And absolutely I had no regrets.

Susan Sly 09:19
That's it's huge.

Jess Feldman 09:21
You're bringing out the tears, Susan.

Susan Sly 09:25
I think it's because we're friends and it is Raw and Real Entrepreneurship, right? And if you're, if you're listening, no, Jess doesn't have a cold, this is emotional stuff. I want to ask you, not even related to entrepreneurship, but you know, there's a lot of talk about, potentially the next recession, we see student loan debt. You know, the last stat I looked, you know, it was higher than 1.7 trillion, which is more than subprime mortgages. Were going into '08, how did you, being on Wall Street, navigate the recession, part one of the question, Jess. And part two would be for the entrepreneurs and people who want to be entrepreneurs listening, what advice would you give them based on what you learned?

Jess Feldman 10:16
Well, a couple things in 2007, 2008, I can kind of see it coming. And you know, I bought my apartment, and back then I was like, Oh, my God, who's gonna buy this from me someday, you know, because I knew that it was coming. And then when we were going through it, and the markets were moving, you know, 1500 points in a day, I kept saying to my wife, I'm like, Oh, my God, people are still above ground. You know, like, as bad as this is, you know, people aren't filling up their pools with like, fresh water. And, you know, it was just this environment where it was like, sort of, you know, survival. And I think that's, that's also what a lot of Wall Street is, I mean, I've been in really challenging situations. When I first started on Wall Street, I was up every single day at, you know, my first real job at like, 4:30 in the morning at work, because I was calling European accounts. And so that was the time to do it. So I had to be in the office then and we'd work until the close at four o'clock. And then you know, go work out, go home, start all over again. In the job after that, right after 911, you know, there was 80% turnover at this firm. And so a lot of it comes down to persistence, it also comes down to listening to what your clients want, you know, pounding the phones, I like to say, and, you know, just working on their behalf. I'd also say in 2009, when I was looking at a like a lot of these earnings, and I'm looking at IBM earnings or Intel, and I'm like, these guys are still doing tens of billions of dollars a quarter in revenue. And so, you know, even with all the problems that are out there, during that time, you know, these companies were still putting up incredible numbers. So there's demand somewhere else. And I think what happens is you get massive rotations in the market. So obviously, financials had not had their, you know, the financials had finally taken a hit at that point in time. But they were also a darling in the market for, you know, a very, very long time and had a very, very long Bull Run. And so then you just see, you know, different flows coming out and just talking to clients. And then, and then even talking to clients, I knew that it was over in March of '09, because some of the, the mutual funds that I was talking to, had told me Look, we have nothing left to sell, which is akin to going to a hardware store. And the guy says, I don't have many hammers left to me, and you're like, but you have three right here. And he's like, exactly my inventory is low. And so you know, it almost started the cycle of re inventorying stocks on Wall Street at that point in time. And so, you know, you just knew kind of when the lows were in place, because everyone, you know, you want to buy fear and sell greed. And at that point in time, there was so much fear on the street in March of 2009, that, you know, stocks had just been beaten down. And, you know, again, like I was saying, and companies were still doing a ton of business outside of the financials. So, you know, there was, there was a lot of opportunity at that point in time, too. And so, you know, I remember that all the time, you know, by fear, sell greed. When you're scared to do something, almost, that's probably the best time to do it. When your senses are completely aware of the situation.

Susan Sly 13:44
And do you, I mean, there's so much there. And thank you for the insight on that. I mean, we had this conversation, you know, Glenn Stearns is a good friend of mine. And you know, it's talking about a rough time during the recession, right? And so, when you think about how the optics are, there's, you know, there's like this doom and gloom, and that's what media sells. But, you know, me being the sunny optimist, I always felt like there's opportunity everywhere, and people were still buying art during the recession, because the people who are fiscally conservative, they are able to buy when no one else can buy and there were people buying real estate for all cash deals. There's you know, all these things that happen. And the, the person who says, well, Jess, you know, I've been thinking of starting a business but it seems so risky to me, given this financial landscape. So this is one of the big questions I want to ask you because oh my gosh, should I start a business, we might be coming into a recession. I feel like we're always coming into a recession because that's what sells you know, Market Watch every morning, I'm on there at like 4:45 in the morning. Like oh recession coming. They've been saying that for the last five years. So what do you say to that person is like, oh, it's really risky?

Jess Feldman 15:05
Well, look, there's, there's, there's never a right time. I mean, you kind of have to go for it, you know. And you just, I like to say, an entrepreneur's basically is his best friend and his own worst enemy within a 10 minute period.

Susan Sly 15:25
Welcome to my world, yeah.

Jess Feldman 15:30
Because you know, you're full of optimism one minute, and then the next, you know, you're just like, Oh, my God, you know, you just suffer from like, constant fear of like, I could lose it all. And you know, and I think you just need to embrace it. And if you're persistent, and you believe in yourself, and you believe in your idea, then you really, you know, there's, there's going to be no right time. It's either you're gonna do it, or you're not going to do it. And if you're not going to do it, then you're going to always wish that you had done it. So I think you really, you really just have to go for it. I mean, I guess, you know, I have to, when I first started, I didn't realize I had to read deinstitutionalize myself, basically, from the corporate world. You know, being at work every morning at six, or you know, four, and then going out to a world that has no schedule. To a world where, you know, you think things happen really quickly when you're in the corporate world, because, you know, you're doing something every day. And you know, when you start a project in the corporate world, you know, you're like, six months is nothing, because you just finished four other projects within that six month period. So by the time you hit that six months, you're like, oh, my god, that was, that was quick. But when you're on your own, you know, the six month project is like, feels like a 12 month project, or 18, as you know. And, you know, it takes time to build trust, it takes time to get your bearings, you make tons of mistakes, you know. And you just have to kind of figure it out. And sometimes, you know, what I found is that you really have to find people with like minded thought process. People that are positive, people that, you know, I used to have people over to my apartment, I would call it like the, you know, the board. And I would just want to talk about, you know, what's going on in your business, maybe we can come up with ideas to help you or a different approach. The other thing I think you have to do is be willing to innovate your business and change it. For example, you know, my mom and I were, you know, we're just buying things for people. And then we thought, you know, what, God, she's been buying things for 30 years, 40 years for people. Like we have a massive install base already of people that have great art. Like, why aren't we selling this? You know, and it was like, oh, yeah, it was like an epiphany or something, you know, you're just like, yeah, so let's do that, too. So we can represent them on both sides, which also adds another element, you know, to the business. When I first started, I had built like, a deck about, you know, art and the market and everything else. And, you know, I would show it to people, and they're like, Yeah, but I'm not interested in the financial part of it. And, you know, I just want to buy what I love. And of course, you know, that's what we want. And so I took a little while to just, I heard what they were saying, but I wasn't listening to what they were saying. And then after a while, it's just like, you know, a friend of mine turned me on to Simon Sinek you don't start with why? And why do you do it? I mean, it's passion. And people will see that if you're really passionate about what you want to do. Whether you're a chef, whether you want to run or run a bookstore and you want to give them the best books that are you know, currently out there or books that have been undiscovered. You know, people will gravitate to and find people that have those common interests

Susan Sly 19:01
I love that you said that about that, that why because that, there are going to be wall kicking moments. Like you said, your worst enemy, doubt, you know, all of it. And if you don't know your why, and have that grounding in the why, the propensity to make mistakes or quit is going to be so much higher, right as you said. And you see businesses sometimes too where you can tell they've gotten so off course from their why that they're making these, all of these mistakes, right? That's, which is crazy. Let me ask you this. So family business. Yeah, that could be interesting. There are movies made about them, you know, or do you remember growing up in the 80s? The show Dallas? Oh, yeah. Falcon Crest was another one. Dynasty, they all have these family businesses but you know,

Jess Feldman 20:02
yeah, who shot Jr?

Susan Sly 20:03
Yeah. Do we know?

Jess Feldman 20:06
I don't know if we ever found out?

Susan Sly 20:08
I don't know. I can't Yeah, that's a question. Well, if you're listening, and you know who shot Jr, will you please let Jess and I know because clearly we don't know who shot Jr. Let's talk about that dynamic because it is a really, it is, it is so different and it's sometimes does go sideways. Sometimes it can go well. What, what advice would you give to someone who's you know, worked with your mom, it might be someone with their spouse, like what advice?

Jess Feldman 20:41
Well, you know, it was funny when I first went to my mom and I said, Okay, I'm gonna do this, she's like, Okay, this is our deal. She gave me the deal. And I was like, Oh, those are pretty stringent terms. But okay. And, and, you know, I just knew at that point in time that, you know, I had to go with it. I was going to be learn— I had a, I was just able to work with somebody who was going to teach me make tons of introductions for me, had very good relationships, you know, people trusted her to bring me into the fold. And I was like, you know, I've worked with hedge fund managers, they're tough as nails, but I'll tell you what, working with your mom sometimes, and she like, just like, crushes your spirit. And you're like, I was like, damn, Mom, you know, like,

Susan Sly 21:34
clean your room, clean your desk, no.

Jess Feldman 21:37
And so you know, those kinds of things where I was like, wow, I just, you know, I have to recover from this. But, you know, she really just meant well, and, and we had a really good relationship. And, you know, I just, it was fun, you know, I just had a great time with her. And also, you know, I kind of asked for this, you know, I didn't, I didn't realize like, as a kid, you know, how fortunate I was going to the galleries on the weekend, because, like, the artists would be there, all these, you know, these artists that are well known today. And that was like, my Saturday morning, no cartoon, it's just like, Okay, go out, you're going to the galleries, that's it, you know, we go for, you know, three, four hours. And that was like, you know, the genesis of it. And then, and then I remembered too, you know, it, all the arts kind of go hand in hand with, you know, theater and a ballet or whatever. And so she would take me to all those kinds of things. And I remember going to my first opera with her. And, you know, they're singing Figaro. And I'm thinking to myself, I think I said this to her, I was like, ma, this is where it comes from, you know, because my education until that time had basically been, you know, the cartoons. And so, you know, she had showed me, like, so many amazing things, so that by the time that I got to work with her, you know, things were just settled. I mean, yeah, sure, they were hard, because, you know, I would go out, and I would discover things, and, you know, you know, and she would take the commission, or wherever, but you know, saying at the end of the day, I just thought, okay, that's the way it is, but she's training my eye. And she's teaching me. And a guy early on Wall Street said, he said, you know, you're either learning or you're making money. And I was, you know, a trader, so you're either learning, or you're making money. And it's the same thing when you're learning on Wall Street, you know, you're not making a lot of money at the time, and then as you build your skill set, and your relationships, you know, you're, you definitely start to earn more. And so, you know, I just thought of it in that way. Like, this is a project that's going to take a couple of years, and I need to develop relationships with my collectors, I need them to trust me. I need to develop all my relationships on the gallery side and with artists, and, and so I had a very, very open mind. I know, you know, there's a lot of people that have a much more challenging experiences, but I would say my relationship with her was, was just unbelievable. I was really fortunate.

Susan Sly 24:20
And I love how you approached it, because I think where any relationship goes wrong is a power struggle. Yes. And, and so I didn't even tell you this. So recently, my 82 year old father incorporated this multiplex that he has, and so I'm a director in this company, right, and he lives in one of the units. And so setting up this company has been hilarious, because he's like, I think I'm gonna bank here and I said, Well, that is it. He lives in in Canada, right? So I'm like, Whoa, that's a little more complicated for me to access the banking. Why don't you bank here? And he's like, this one charges $4 less a month in fees. And in my mind, Jess like, as you know, I'm a doer, I pay attention to the cash flow, statements, like I'm so that I'm like, here's the difference. If you do business with this bank, I'm gonna have to fly there every time I sign something, if you do business with this bank, we're gonna pay $4 more a month. I said, Daddy, I'll just pay the four damn dollars. And we'll be, we'll call it good. And then there's certain things the way he wants to do it. But the way I approached it is not that here, I am almost 50. You know, you're helping to grow this amazing technology company. But I'm still his daughter, I'm deferring to his wisdom. And so to your point, in that role, I'm learning. Yes. But in my other role, I'm leading. And, and I think it's that, that trade off, when you come into a business or I was just doing, I was a guest on Henry Kaminski show and we were talking about pivoting your brand and pivoting your life, that there are times to be a student, there are times to be a teacher, —how you approach that, Yeah.

Jess Feldman 26:10
I was gonna add to that, because one of the things that I really realized is that I have to listen, you know, when my mom is talking, and when she's with other people, like, I just have to listen, it's not, it's not my show, you know, and listening and learning. You know, we don't do enough of that, in many cases, is just listening to what people are saying. There's a lot of information in that. And, you know, I was just, it was also the ability, you know, to, to ask questions, you know, and ask, why didn't you do this? Or where did you go wrong? Or how did you know, why didn't you think of this, you know, and also a way that I think was very familiar too that wasn't, you know, threatening, because it wasn't like, why didn't you do this? You know, but it was just like learning, you know, from, you know, where you made mistakes. And so that I wouldn't, you know, repeat them or I could learn from them.

Susan Sly 27:09
So, another question I have for you is relationship collateral. So because your mother is, you know, so established, right? So and one thing is that you and I had dinner in New York at the beginning of the year, and we're talking about you had to go and build your own book of business as well. Oh, yeah. And oh, yeah. So how did that how did that go? Certainly it went well, but how did you get started doing that, right? Like..

Jess Feldman 27:39
Well, I had basically, I had one collector, and I was like, this is proof of concept. Trust me, this wouldn't work in the world of biotech or anything.

Susan Sly 27:52
Oh, that's not true. In Silicon Valley, here, I've got a napkin. It's my proof of concept, yeah.

Jess Feldman 27:59
I was like this can work. And, and in reality, you know, I just, I just had to persist. And, you know, go and meet people, you know, make the trip to Europe, go to meet the gallerist. They really appreciate you're making that effort. And it's the effort to go see every show in New York or to spend time with them. And it's real, you know, like, I've never almost been in a business where, or you just want to help each other, you know, New York's Wall Street's a very, very different animal than that. And I work with a lot of really interesting people that, you know, I just want to hang out with too now. And so, on the client side, you know, my client, my business is really only referral based. I don't, I've learned like, I don't want to sell art to people. If people have an interest, they find me. Because once the interest is there, and it doesn't matter if you're starting from scratch. Like somebody said to me today, oh, I don't know anything about art. And I'm like, That's okay. As long as you have an interest in learning about it, because a big part of my job is educating people, just about art, you know, from wherever it is the Impressionists, all the way through to today, we just go see different shows. And so, and there's, there's no pressure. And so I think, I never told my collectors, oh, you have to buy this. It's really what you know, I bring them to see things and whatever kind of sticks in their mind. And so I have a very, you know, I don't put any pressure on anyone. And I think a lot of my collectors just like that, you know, and I take him to just great things. And I tell them, you know, the straight story. And so again, it's all referral based. It's also persistence, and being in front of people, and just, you know, continually showing them great things. And as those artists evolve over time, I think they also see that You know, you know what you're doing. And then it becomes really exciting for them. And then when you get your first piece in their home, it just transforms the place. And that's super exciting for them. And, you know, I've started having, I've also had to change my game in terms of just having people to my apartment, you know, and it's not about selling the art, but the arts around them. And so they say to me, oh, you know, something, I'd love a piece by that artists, for example, you know, I love that piece, or I've had, you know, an event for an artist in my apartment, who I really believe in. And I collect too, so I put my money where my mouth is, and I'm buying things that I believe in, and also showing those things to my collector, although I don't sell from my collection to those collectors. I will go out and find them new work, because there's a conflict of interest there. But I am buying alongside them. And then really, it's all about creating a larger environment for them. So we start with art. But then I love doing like jazz nights in New York, where we, you know, I have 10 people that go to a jazz concert. And we just come back to my apartment. And, you know, we have, you know, some wine and some cheese. And it's a very, very simple evening, and it's a lot of fun. And everyone has, walks out of there and they had a great time. And again, it's just like another iteration of my business. But I'd really do it because I love it. It's not, it's it, you know, I have no other motive other than just going out with people and bringing them to great things. And then building a really, you know, continue to build a great relationship and a great rapport with them. And so it's all referral based.

Susan Sly 31:43
I'm inviting myself to the next jazz night. Just so you know. It's like the, you know, I'm really the, the whole piece, what I'm hearing too, it's the relationships, it's the experience. It's not about doing business with you. It's the experience of doing business with you. And you're the, so I grew up, you know, going theatre, galleries, Jazz, so I'm like, Oh, the next, the next funding round we do for Radius, I think I'm doing a jazz night, I bet I'm gonna serve some wine. And yes. Forget this traditional VC pitching stuff. We're just gonna have fun. If you're in, you're in. If not, we're still friends. And that's I think that's what I'm gonna do. Yeah. And you could co host it. So and then you know, some people might buy art and invest so we could be, this could be a new business. People are giving away NFT's when you're investing in WeFunder rounds. So we could you know, we could do something like that but not with NFTs. You'll never know.

Jess Feldman 32:55
Never know.

Susan Sly 32:57
Well, Jess, I cannot thank you enough for being here. And if you want to find out more about Jess and his business, go to www.sjfeldmanartadvisory.com. And who knows, maybe you might be invited to jazz night. Or be like me, just by yourself, why not? Anyway, my friends, this has been another episode of Raw and Real Entrepreneurship. I hope you are doing amazing. Go out there and rock your day. Keep charging and I will see you in the next episode.

Jess Feldman 33:35
Great. Thank you.

Susan Sly 33:36
Thanks, Jeff.