Ep.196- Jay Sapovits: From Marquee Jets to $5M Inked Stores – Entrepreneurship Lessons in Resilie...

This is the You Winning Life podcast, your number one source for mastering a positive existence. Each episode, we'll be interviewing exceptional people, giving you empowering insights, and guiding you to extraordinary outcomes. Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship so you too can be winning life. Now here's your host, licensed marriage and family therapist, certified neuro-emotional technique practitioner, entrepreneur coach Jason Wasser.

Today on the You Winning Life podcast, we're sitting down with a man who's built million-dollar companies and also survived the kind of business heartbreak that would make most people walk away for good. Jay Sappovitz is the founder and president of Inked Stores, an innovative swag company that's grown to over $5 million a year in revenue and has built more than 1,000 online stores for for brands like Penn Entertainment, DoorDash, and Crocs. But Jay's story isn't just about merch. It's about resilience, reinvention, and doing the next right thing every single day. From helping scale Marquee Jets alongside Jesse Itzler and Ken Dichter, to pivoting out of a failing fitness brand into a thriving online business, Jay has lived the highs and lows of entrepreneurship, all while staying grounded, in relationships, humility, and service. In this conversation, we'll explore what it takes to rebuild after failure, how to pivot under pressure, and why sometimes not being tech savvy can actually be your secret advantage. All right, everybody, welcome back. And as you know, we're hanging out with Jay. And Jay, thanks so much for, for hanging out with us today.

Jason, enjoy it. Uh, looking forward to it.

Cool. Awesome. So number one, you've had this really cool, eclectic career. And one of the things that you're known for is for seeing opportunities.

Yeah.

Others don't, right? That's, that's what I would call it, right? Super talent or whatever you want to call it.

I call it desperation.

Okay. Well, let's talk about that for a second because I'm looking at it, right? I'm a therapist. I, you know, one of my key things is to be able to find patterns where people are getting stuck in beliefs, assumptions, and expectations. And then, you know, they're trying to work solutions from that place, which only gets them, right? It's quicksand theory. Um, or as Einstein Einstein said the problem can't get, you know, solved from the place in which was created it.

Yeah.

So walk us through— yeah, like you just said, out of desperation— but walk us through a little bit of this, just that insight, that perspective, the psychological experience that you've had from what you're calling desperation, and I'm looking at as a superpower.

Yeah, well, I mean, I didn't know any better with respect to starting a business. My dad was a school teacher. I watched him hate his job and life. Um, most of my upbringing. And, you know, it was a really difficult— I mean, you know, I was very close to him, and it was very difficult to watch. And I just swore that I would never be in that, in that same situation. I did get myself into a pattern of, you know, if you were talking on a psychological level, of escape, um, where I would look for opportunities even if I was if I was in one very early in my career. But yeah, more than that, I think that I was chasing something, that I was chasing happiness very early and when I was younger. Now, having said that, I was able to build some businesses throughout that process. So, I don't think it all turned out bad. But yeah, as I look back, I look at my career and I don't look at it with regret, but I definitely identify that I had a pattern of escapism going relative to creating, looking for opportunities when I maybe shouldn't have been looking for those opportunities and just ridden out the opportunities that I was on. Age gives you perspective. And fortunately for me, I was able to gain that, which is why I've been in my current role for 10+ years. And I often joke that I'll die in this business over a screen print press. So I love this business. I think an important part of not acting out, and I do call, you know, starting companies when you're in good situations acting out. I think an important part of that is doing things that appeal to your, your, your best attributes, right? So, you know, like, I love the fact that the promotional business is both relational and transactional. So when I was in the private jet world, your sales cycle was extremely long. So it was a relational sale.

Sure.

But it was very little transactions. When I say very little transactions, I mean, you know, I still sold a bunch. You know, I had $2 or $3 million months and I would sell 10 or 12 clients. I sell 10 or 12 deals in my current business. A morning, a day. So I can start with nothing in the morning in this business and have a great day from out of nowhere. So that appeals to things I like. It gives me, uh, hope, right? I'm a— I wake up every morning with hope. So I may come into the office and not have anything going, but I know that I can So it was important for me to find a business that allowed that to happen. Also, a business where I could use my creativity and imagination, which I think promotions does. So yeah, I jokingly say that desperation helped me find gaps. It's not all It's not all joking. I mean, the first business I ever started was with Jim Furyk, and that was an evolution out of sitting in a cart shack because I was in my recovery job at 25 years old. So I just noticed a pattern of the golf course that I was working at. I worked for tips, and I noticed a pattern of not getting tips from 10 till 2. So given that pattern, uh, I figured I, I was going to try to fill that gap. So I, you know, with clarity, looking for that problem, right?

And yeah, this is what you're saying. It's so interesting. I wish you were on my, uh, last session call because this is so apropos. So go figure. And I love how this happens. Like, I, I don't know if this happens to you, maybe I'm Well, it probably does happen to you. Maybe let's put it that way, is where you have particular themes happening in particular conversations over the course of a day or a week that hasn't showed up elsewhere. But then all of a sudden you have a conversation in the morning. You're like, God, I wish that person was there, like, you know, later in the afternoon to be part of that call. But like, you're so spot on to this conversation. One, I mean, I love the language that you're using, right? Because I know there's a lot of recovery language in some of this, right? Which is, which is cool from my perspective. But, you know, the idea of chasing happiness is something that I had a conversation with about an hour and a half ago. And I basically told this person, I'm not here to help you find happiness. That's not my job. And you shouldn't be. And if you're thinking that you're paying me to make you happy, let's call it a day, right? Can I help you define your core values? Can I help you find people that partner, align with your core values? Can I help you craft your mission and then go out into the world and put that out there? Can I help you bring contentment and legacy and joy but I'm not looking to aim to help you find happiness because happiness is an experiential moment-by-moment thing. It's not a state of being.

That's interesting. I wonder— I mean, I know that happiness shifts in and out, right? So I'm definitely aware of that concept. But I think that you— I think it can be, while not constant, I think it can be a state of being. So I actually—

challenge me. Good, go for it.

Well, yeah, I don't necessarily agree in that I think where for me, where I look at my life now and I have an overall happiness, right? I love my wife, 28 years married. I have 3 beautiful kids, 2 of them are employed, uh, out of college, living in Manhattan, living the dream. They're happy. When they're happy, I'm happy. My third is going to be a rising sophomore in college.

Yeah.

And at 54 years old, I've come to the conclusion that I'm not going to be the next Steve Jobs and I have enough, right?

So, so is that contentment?

I don't think I'm content. I was in the office this morning at 6 o'clock. I don't think content people get to their business, get to their business having been in business 10 years and sit at their desk at 6 o'clock in the morning. I'm not content, but I'm, yeah, I'm, I'm I'm— I have enough. I'm happy with what I have. And, you know, that creates this overarching level of happiness for me that I carry on a— no one carries it all the time, right? But my overall being is I mean, that's how I feel. My overall being, I'm happy. And, you know, I just don't— we, you know, we did mention recovery. So it's my— I have a sponsor, of course, and, uh, you know, we're in touch all the time. And he has a phrase when a guy tells him that he's having a bad day. He said, you're not having a bad day, you're having a bad 5 minutes and you're milking the shit out of it.

There we go. Yeah.

So when you talk about, can you be happy as an eternal, as a, as a, as a, as a state of being? I think the answer is yes. That's my feeling.

I love it.

But I'm not— I understand your— I understand where you come from as well. And I'm okay with that. I don't, I don't need to be right.

No, no. What I, what I think what we're in agreement on, because I'm not looking to be right here exactly, is, is where's the starting point? And what are the definitions and parameters we're putting around what we call a successful achievement in any area, right? And for a lot of people, happiness is that. But in order to use this nebulous term happiness, we got to get really clear what that means to you. So why I would 100% agree with you is that you laid out the recipe for what equals happiness to you. It's not this vague thing that you're chasing that's out there like a carrot. It is the investments into your personal well-being, the investments into your marriage, investments into your children that you're seeing, I'm using business term, but return on investment, right? And therefore, yes, happiness in that regards can be in that, right? And that's what I do appreciate, that definition and that way of looking at it. The way I was looking at it was more along the lines of a lot of times people are like, I don't know, but I know I'm not happy. Or I've been happy with X, but now I don't have that. So it's still state-dependent, it's still experience-dependent.

Yeah, look, and I had that for a very long time, and I had that for a very long time where I had this lack of contentment. I didn't feel like I had enough. Nothing was ever good enough. I mean, you know, I had it— I lived the dichotomy in my life where I was, you know, entertaining and going to the best concerts and eating in the best steakhouses Monday through Thursday, and then on the weekends being handed kids, being told, "Take care of them. Now you're a dad in a suburb of Boston." And that was a really hard thing for me because you'd live one life during the week and live another during the week. And it eroded my spirit to the point where I I left a very high-paying situation to start my own business, which ended up being not successful. And when that wasn't successful, I mean, talk about picking up the pieces. I mean, I was 39 years old and almost broke, and that after having had 2 successful runs in business. So, yeah, would I change it if I could go back in time? Yes. I laugh at people like, you know, maybe who I am today, or I wouldn't change a thing. It's like, no, like I suffered deeply from failure and I don't look back at it with, with positives in my life at all, which is ironic in that as I've gotten older, the people around me look back at it as positive.

About your challenges or about their own challenges? Okay.

No, about, about like, you know, they'll say like, oh, you know, hey, I remember when you left to start that business. And I'm like, yeah, it wasn't the most successful. Oh no, I thought it was really cool. It was great. You know, so they'll have positive, they have positive memories of it. Just me who doesn't.

And, uh, you were sitting in it. They weren't, they were, they're with you for sure.

It's just, it's a lesson in life though. It's like, it's how you're perceived by others is not necessarily how you perceive yourself. And, um, I've, you know, it's, it's funny, right? As much time as I have in recovery, I definitely rededicated myself, uh, 10 years ago to, you know, being involved and, um, you know, working in the homeless shelters monthly and speaking at the men's houses and doing the things that it takes to actually live in that life. Of, uh, um, of recovery, which has been, which has been terrific for me. And yeah, I mean, ever since that jumping off point, it's, you know, my kids were of a certain age when that happened, um, and yeah, since then, blue skies, everything got better, business took off, um, marriage got better, my relationship with my kids, my son, daughters, best friends. Like, it's awesome.

Is there stuff that you see— I mean, you've been doing this for a while, you've, you've walked the walk and you're talking the talk. Is there stuff that you see is commonly, like, just from that part, just going back to what you're saying, like there was a dead— a rededication?

Yeah.

And I have an accountability group and we meet, happen to meet Wednesday mornings, and every few months I bring up that same challenge. It's like, what aren't we talking about that we need to be talking about? And what are we focusing on You know, where are we getting lost in the weeds? And today this— I brought this up actually. So again, it's funny how this is coming up of like I told them that I missed the feeling of the fire under my butt when we would come back from our conferences with our business accountability group and with a gentleman named Rick Sappio who passed away in December from pancreatic cancer, one of our mentors. Thank you. My joke with, you know, and I told his wife this at the funeral. That, you know, that a perfectly imperfect person can still have massive impact on the world. Right? You can be wildly imperfect.

Yeah, sure.

Right. And still have impact. So this morning we were talking about this idea of like, we're doing this thing every week and it's useful and I love them. And but what is it that we need to rededicate ourselves to that we might really allow us to take that next bigger step than just the status quo? And the status quo is good, right?

I'm—

let's talk about like contentment from that angle, right? I'm content with what we're doing, but I also want more and I'm looking for more. Is there kind of things that you have seen with yourself, with others where they may not realize they're leaning into, you know, because on one side you can look at content is I'm happy with my lot. I'm motivated. I'm excited. I'm happy about it because I'm not really lacking anything and I'm feeling positive about that. And then there's the other definition of contentment, which is, you know, I can get malaise and I can get bored and I can get not pushed by this. I don't necessarily— I'm as excited to wake up in the morning to do that. Is there some signs that you've seen yourself, people you've worked with, people you maybe mentored and guided where they might be going into the dangerous side of contentment that people cannot realize that these are patterns that are showing up?

Look, I mean, for me, it's simple. It's like, you know, when I sit around and relax, my life gets worse. The more time I have alone with me, the more thinking time I have.

Yeah, right.

I get this thing going and, you know, all of a sudden I could probably lose a little more weight. You know, I— maybe this person shouldn't have said this to me. You know, I just— it gets into my— I get in my head. Um, yeah, I just need to stay active. And I think, I think action is really the key to any person's happiness. I've known a lot of people who either haven't had to work because they're just so wealthy, or if they've retired. I mean, the stories are endless, right? Joe So-and-so retired, and 2 years later he was dead. I mean, we all know that story. So yeah, for me, I've got to be active, I've got to be on the move, I've got to be doing something or else I can slip into a negative mental state of mind. And that's in business and in my personal life. So I have to just live in that state, you know, for my business. I need to be doing the right things and taking the right activities. And that means calling on my customers. Running the business without getting into too much detail. For my personal life, you know, in recovery, I've got, you know, I've got to make time for my wife and kids. Recovery, I got to make time for the guys that are trying to get clean and sober and frankly those who aren't, right? So the volunteering at the homeless shelters and the men's recovery houses and things that aren't necessarily at the top of my list 28 years in, right? So, you know, I take action against my own, you know, like if I don't want to do something, it's probably something that's good for me. If I want to do it, it probably is bad for me, right? So makes sense. I have to take action against my own will on a moment-to-moment basis. That's what leads me to my success.

So I'm hearing the, the undercurrent of that is, is how to— is being humble in relationships.

Yeah, I mean, humility is everything. Yeah, ego suppression has changed my outlook on life. Yes.

Yeah, tell us more about that.

Well, it's, you know, um, whether you believe in God or don't believe in God, um, I know Uh, well, I, I happen to believe, but what I believe more than that is that I'm not him, right? Right. So the world doesn't center around me, and to the degree that I can just live a life where I understand the world doesn't— everybody's not thinking about me, right? You're driving too slow in front of me, you're not there to screw me. You take my parking spot at the grocery store, you're probably oblivious to the fact that I wanted it. So I think for a long time, and I'm talking about after I was clean, I had a bunch of good years and then you sort of get away from it. There's a lot more people in the room with a year than with 20. So you sort of get away from that. And you start thinking that the world revolves around you and nothing good happens from it. It fuels your anger and discontent and resentment and preys on your fear. And yeah, you just end up just— the spring in your gut tightens and tightens and tightens. And yeah, just not— just completely letting that go has changed my world. Even with clients, uh, the ability to talk to a client and tell them, you know, something went wrong, or, hey, what you thought was going to happen isn't going to happen, or how do you, you know, do you sit on it for 2 days? Or do you make the phone call the minute you know? Right. So it's just a series of, again, you know, the negative, you know, we all have that sort of like inner dialogue, right?

That duality. Yeah.

And we all know when we're doing wrong and we all know wrong from right. Like, I'm convinced everybody knows wrong from right. It's just you're either going to do right or not do right. I, I mean, I haven't, I haven't behaved in a way that has been detrimental to my life where I was like, no, I'm doing the right thing, I'm doing good. Like, no, you know?

Yeah, but I don't know how many people out there can truly say that, right? If they're, if they're going day to day and, and there's always something. And again, I just had this conversation and The person's like, well, I don't know if I want to repartner with this person. And I'm like, but I remember in our first conversation when we met 2 years ago that you said something about the core values of this person or the way that this person treats people. And then there's a part of you that completely blocks that out in a business setting that they just go in and bulldoze everybody, right? That, that type of entrepreneur, you know, that gives it the bad name. And yet here you are saying, but I still want to be in partnership with them because it's okay. So are you okay with the transaction? But are you okay? Having your brand in alignment, your personal identity and brand in alignment with a, with a brand and personality that treats people that way.

Yeah. Well, I mean, I bulldozed my share of people over, you know, over periods of time and been bulldozed. But what I definitely identify with is that when that behavior surfaces, right, and it does, I feel like crap. Yeah. So if I were to be angry with you, I actually am the one who hurts, right? So you do that enough and you feel enough inner turmoil and pain with treating people in a way that you don't want to treat people, or that causes negative effects to come back on you.

Yeah.

Uh, you stop doing it. Right, or you limit the amount that you do it. Yeah, look, I mean, yes, there's a, there's a, there's a subset of people who are oblivious to their actions. I understand narcissism exists. I'm not that person, right? And I generally don't think most people are, but I'm also extremely self-aware Um, for better or worse.

Yeah, well, I think that's a key of why I created this podcast, right? Because I'm coming out of a therapy practice, but I work with a ton of entrepreneurs. And, you know, and a lot of people are avoiding moving into that space because there is that negative side of, you know, everybody's a sale. If you're, you know, if you're not— what's that old thing? If you're, uh, you know, if you're not closing Right. The whole, you know, ABCs and all the shtick from all those movies, Boiler Room.

And you really think that's why people aren't becoming entrepreneurs? I actually think it's just fear.

Fear also. Yeah, for sure. I think that's a part of it.

Fear is a big place. It has a big place in it. And then I'll tell you something else. I think that— I think people don't become entrepreneurs because they're— they don't know what to do.

Yeah, the gate— the— well, there's definitely gatekeeping and basic information that's more available now, which I think is why you know, people like you, like Jesse, you know, other people like that, how David Meltzer, stuff like, right, that are putting out really amazing information because they do want other people to win. And right, the rising tide raises all ships mentality is really what I appreciate. But I do see people are either afraid for sure, but they're, but they're coming from that, you know, the, the technician side of things. So they don't know how to think like an entrepreneur or a manager. They only know how to think like a technician, like the—

Yeah. Oh, for sure.

Right.

And I didn't know where— I didn't know what— I didn't know what to do either. I just had— I was just young and plowed forward without any knowledge of what to do. And, you know, I definitely made my mistakes, but yeah, I mean, I was, I was such a bull back, you know, when I was younger that, uh, you know, I was exactly who I'm talking about that I don't care for now. So, uh, yeah, how would someone leverage that, right?

So how would someone leverage the positive attributes of what you've arrived at now, right? The positive mind space, the healthiest version of you to date, with that tenacity, or maybe that, that bull, but really running, you know, making that person a bull through that version of who you are now? How can, how can people— because I see that as a difficulty, right?

I have clients, and you think it's hard to be nice and also, uh and also run hard?

I don't think so. I think there are people out there who don't think that it's possible that they would have to sacrifice certain aspects of themselves. Yeah, because of the structure and the model.

But I just don't agree with the concept of always be selling, right? I don't agree with the concept. It's like being an entrepreneur, you always quote unquote need to be on, like, right? I just don't think that's a reality. I, I, especially in today's world, I mean, the digital assets that are out there and the shortcuts that you can have to launch. I mean, to me it's just problem solution. Find a problem, create a solution, sell to one person. And if there's one person out there who'll buy a solution to the problem, then sell to another person, right? And by the time you've sold it to two people, you have a business. Now I don't know how big that business is going to be because I don't know what that problem is, But there's a business, and that's to me all it is. And I think everything else is an excuse, and I think people love excuses. And I've listened— I mean, you're coming from a guy who made them. I know what excuses are. I've made sure people make excuses. I do it. I've done it. Um, but yeah, if, if you just got to go out there and find a customer And you don't need a website and you don't need a blog and you don't need a social media handle and you probably don't even need a business name. You just need to solve somebody else's problem. And if you can solve somebody else's problem and they'll pay you money for it, then you have a business. Yep. And all the legalese and all that other stuff, you'll figure out how to handle that, right?

It's a reverse engineer. Oh, I agree with you 100%. And that's exactly the conversation I had today. I think what, what I was proposing using was the myths that are holding people back. Right. But what you just shared with me is exactly verbatim what I had the conversation with my client an hour and a half ago. And it's— yeah, it is like, what is the problem that you are uniquely positioned that, you know, other people in your industry are commonly having to deal with and having difficulty dealing with, but no one is helping them solve that. And that's, that's a space you can move into in your very large, wide industry and get the crumbs on the table. And still make millions of dollars a year from the crumbs on the table.

And how about you don't make millions? How about you just make $10,000, $20,000, $30,000, $40,000, $50,000? You know, I mean, like, how about you just enjoy the fact that you've created something from nothing? And if it takes off, awesome. And if it doesn't take off, then you can decide after you've worked hard and given it your best shot that you're going to potentially do something else. And oh, by the way, you'll have more experience when you do it, right? You're— people get the concept of getting this, of like, this scale is so debilitating, right? You're not Jeff Bezos, you're not Mark Zuckerberg, you're not, uh, Steve Jobs. Like, I'm just, you know, like, I'm not Alex Hormozy, I'm not— I'm not Jesse Itzler, I'm not Kenny Dichter, I'm not any of these rock star sort of like flam, way out there visionaries. I'm just a guy who runs a shop that prints some t-shirts and embroiders some stuff and sells some promo items. And we have a pretty nice business and our clients like us. And we employ a few dozen people and have good accounts with a lot of people that respect and care for us. And you know what? That's enough. I just think that to me, the biggest detriment that you can do is like getting caught. The biggest hurdle— talk about fear— the big is like, and then there's like, what are my friends going to think? It's like, you mean your friends who haven't started a business? Them? I mean, it's nuts.

Yeah, yeah. These are the myths, right? These are the things that I think are holding people back, exactly what you're saying. And it is debilitating. I remember doing this as my own You know, when I left a group practice to start my own thing, um, and I remember the rent was $700, I was about to co-sign with a, with a colleague of mine, a small 2-office little place to do our private practice, and it was $700 a month. And the last day, uh, right before we signed the contract, my friend walked away from the deal. And this was, I don't know, fun times, fun time. And I was losing my crap over a $700 a month rent. Well, $350 Well, would have been $350, right? And now it went up to all me because she— they walked away from it. So now I'm like, oh my God, that's your exposure, $350.

It was committed to $350, correct? Now you had to figure out how to get another $350. You were losing your mind over $350.

Exactly.

You look back at it and it's like hilarious, right?

I know, I know, right? Because I just did my, my sublet because I now got moved out of my own office pre-pandemic, which I had a nice office and subsequently from that one. And now I'm subletting and I'm just paying by the hour. And I just did my monthly and I'm like, oh yeah, I think I may have paid them $350 last month to use the office whenever I want to use it, right? Back then it's kind of like, well, now it's a business write-off. Then it's like, oh my God, am I going to be able to put food on my table?

Yeah, I totally understand. I mean, I, I remember talking— this is back when I was in the jet days— and, you know, one of the gentlemen who was my client become a good friend and He came from a family, his wife's, where the grandfather was extremely successful in his industry. And we would talk about what he was like. And in his mind, whenever one of the grandkids would do something, he would immediately vault into, well, you want to be an electrician? That's great. Like, you, you know, you could run a company that handles all of the commercial electricity for, you know, the big construction projects. And, you know, what my friend said to me is like, well, yeah, but maybe he just wants to be an electrician.

Right?

Right.

As if there's something wrong with that. Right.

There isn't anything wrong with just wanting to do your job or do a job. Right. So not everybody has to be like this mega superstar entrepreneur and not, you know, some people, you know, drive down Main Street and look at the local— we have a juice store, um, we've got a yoga studio, um, we've got a portrait shop, we've got a guy who sells cabinets, a guy who sells carpets. When you drive down Main Street, you just say to yourself, like, geez, how much could the revenue in these places be? And the truth is, like, that's somebody's living, right? And it might only be $50,000, $40,000, $50,000, $60,000, might be less, could be, you know, could be less. And not everybody hits a grand slam. And not everybody has to hit a Grand Slam. So, you know, I think that, um, from a mindset standpoint, it's— truth is really important in this whole concept. If you can't be truthful to yourself, you know, there's an old saying, right? When my head hits the pillow, I know what's real. And If you can't be truthful to yourself, then you're probably not cut out to do anything but work for somebody else. Yeah, because you've got to be able to see reality from what's fancied. And it's just a, it's a critical skill for an entrepreneur. Now, what you want to project is what you project, right? If you want to pretend to the world you're something you're not, albeit, you know, I wouldn't do it, but if you— there's people who do.

Puny. Yeah.

But you can't lie to yourself.

Yeah.

That's, uh, that's a going out of business strategy.

Well, I think that was, you know, that, that this decade— let's just call it a decade, right? Even though it may or may not have been 10 years. But I think like, that's— these are the myths of what entrepreneurship is thankfully, I think, moving away from. That was the big big social media explosion of influencers and renting the Lambos and the jets and saying, this is what I'm doing. And meaning there was no, but I'm going to teach you how to do this, right? Type of thing, the sell the course, which many people are doing great at selling courses that are genuine, authentic, and it's practical and tangible versus it just being a multi-level marketing scam. I think finally we're moving. I'm seeing we're moving away from it. And I'm seeing a lot of the good people, the true genuine-hearted, good people winning when it comes to adding, you know, like you're saying, like, you know, you're doing what you're doing during the day, but you're also making sure you have time to go do your speaking and go spend time in the— right? I think those like you are finally, finally breaking through the noise. And it doesn't have to be sexy and fancy.

I actually stopped going to Boston networking, startup networking events because everybody had been successful. Everybody was a founding of partner of a company that exited for $100 million. And, you know, nobody had ever closed or failed a business. And I'm fortunate now, I'm part of an entrepreneurial group that's extremely real and people share their vulnerabilities openly. And I excel in that environment because, you know, I feel like in some ways I live as an open vulnerability. And yeah, I, you know, I just can't stand the— I just can't stand the fakeness of it all. But what can you do?

No, no, I know. And I think that's kind of where me sitting here as a therapist and always going back to that genuine, authentic core values perspective is it helps clear out a lot of that clutter. I think it does eliminate the chaos. Rick, you know, used to say, you know, if you tell me your core values, I can help you create the life you truly desire. But we have to start with that because we have to know what we're putting up as a barometer to say yes or no to. And there's things in your life that you are saying yes to that you shouldn't be, and there are things that you're saying no to that you— but unless you have this clear, it'll streamline that, that process. Um, but I'm, but I'm wondering, you know, so you're right, networking groups, all these different things, are there You know, when, when someone's going through this journey, right? So you can look back and share this wisdom. Are there things that you would say this could help someone who's earlier on skip a challenging step or two if you, you know, hear this idea or hear the story? Or do you find it's still beneficial for them to go through that without having that insight or information that like you can, so to speak, offer like, hey, when I was there, don't do this, or is it still beneficial for them to be like, still make that mistake?

Yeah, I think it's business dependent. I don't, I don't think it's an overarching, if you're an entrepreneur, do X, Y, or Z. I think it's, I think it's business dependent. I, the biggest mistake I ever made in any of my companies is I built a product without selling first. So I built a product that I didn't know if people were willing to pay for it or buy. So I— to me, that would be the one universal lesson I would say, is that if you can't sell somebody the— your, your service, then don't waste money, your time building it.

Um, I had a conversation with a friend about that a few weeks ago. They presented this idea with their whole building this app and whatever it is, and I'm like, that really sounds like such an such, and they're like, what is that? I'm like, you didn't do market research to see if there's anybody else doing this? And I showed it to them and they're like, oh crap, I just spent the last 8 months building something with a developer that I just have to shut down tomorrow.

I mean, that's insane, right? That's, that's, that's insane, right? I mean, spending 8 months on something and not doing your market research into your idea in today's world with the internet is, uh, it's a waste of time and money and energy and spirit. Um, that's, that's unfortunate, but it's, uh, it's self-inflicted. Having said that, the other, the other concept I guess I would share is, uh, not to get hung up on the idea. Um, I think, you know, a lot of— and that's, you know, part of my learnings of having built the business that people, uh, didn't financially respond to his customers. Um, you know, and listen, it was a hard time. It was '08, and that was not an easy sale. But, um, I, you know, I didn't— I built the product before I had sales, and that was painful because we had a bad time in the world financially, and we couldn't navigate our way out of it. You know, I've gone back in time God, definitely things I would have changed. But that said, um, we didn't need to reinvent the wheel, and we tried to. And a lot of times people will think that it's the idea, like you're talking about the app, right? Like, I sell t-shirts, sweatshirts, hats. Tumblers, right? Yeah, put logos on them, sell swag. Yeah, right. It's a $27 billion industry. Hello, right? Nobody was waiting for Jay Sapowitz to get in the swag business to make swag, right? I just came in and said, I'm here, you know. So I refer to our business as the pizza shop business, right? I mean, every time pizza shops How many pizza shops you think you have within a 3-mile radius of where you're at right now?

Too many.

Just give me a number.

What do you think? Uh, within 3-mile radius, I would say there's probably 5 to 6 mom-and-pops and 3 or 4 chains.

Okay, so it's 10, right?

Give or take. Yeah.

Okay, I bet you the number's 20.

Hmm, ones I don't even know about. You're right. They're not advertising.

Not about the Italian restaurant that serves pizza. If somebody likes their pizza better than— the reason I say that is because I know in my town there is one, but I go to the same three, right? But there's— but none of those 20 have ever gone out of business in the 22 years I've lived here. Why? Because that's how much pizza is eaten, right? Now, somebody ranks 20 and somebody ranks 1, but none of those pizza shops invented pizza, right? It ain't the idea. So it isn't the idea and sell something before you go big. Now, if you're opening up a pizza shop, obviously you can't sell pizza before, but you better figure out what your unique piece is. Versus somebody else on the block because they got a little bit of a head start on you. Yeah, but yeah, hit me back on that count. I want you to count. I want you to like a couple miles, 2, 3 miles. You'll know who to count. You'll know like places you would consider ordering from. I call it that, right? We're 20. 20.

Well, it's funny, I live in a very, right, culturally Jewish ethnic community, so we got the, the Israeli flawful shawarma places. So I got mine that I go to as my primary, and I know there's probably— I know there's 3 others on the block within it, with not even within like— we're talking like a mile and a half straight shot. Street.

Been there a long time.

Been there. Uh, some of them are newer and some, some have— there's been one or two that— one that moved to another city that was there forever, but rent related, and moved to another location here in South Florida. But I have mine that I— that's my default go-to, and I don't really consider going to the other ones. That's even one in the NexPlaza.

But they're not closing down left and right. No, they open and they stay open, right? Because that's how much demand there is. So you don't have to invent something, you can just sell something. Not my invitation for anybody to get into the swag business.

No, but if you're the company, you need the swag, you never know who to go to. How about this?

You don't need my invitation to get into the swag business. You just open your doors and you're in it, right? Like, that's the beauty of, you know, now are you going to be in it as deeply as I am day one? No. But, you know, 4inPrint kicks my butt. So, I mean, you know, we all have people who we, uh, we're, uh, smaller than, right?

Yeah, yeah, yeah. I see it with therapists, right? I have 3 graduate schools. One that I went to, that's, that's a 12-minute drive, and then there's 2 other. University of Miami is 45 minutes south. FAU in Boca has a social work program. But at least most of the schools have at least 2 or 3 different counseling departments— mental health, social work, family therapy, psychology, right? There's at least more than one program. So there's got to be easily 1,000 therapists within a, you know, in this, in this, in a 15-mile radius. It's always been like, what is it that makes my practice different? And it can't be like, oh, it's a population. It's not a psych— it's not a, it's not a, uh, you know, uh, psycho— it's a psychographic. What are the problems that I'm here to solve? And what are the problems I'm not here to solve versus I just see couples, adults, and families? Like, no, no. Here's what I touch, here's what I don't touch. Here's the angle and the perspective as a mind-body expert, as someone who works with entrepreneurs, right? To have those 2 or 3 things. Other stuff I don't touch. I don't touch mental health. I don't touch schizophrenia. I don't touch bipolar. I don't touch domestic violence. There are therapists that just want that stuff.

Yeah. Well, focus is important. You learn that over time as well. I mean, when you first start in business, you take everybody, like I'm sure I did.

I did, probably, with all the insurances and now Medicare.

Yes. And then as you Right. And that's the other— yeah, I guess if you're dragging it out of me, the third piece is like, you just don't have to be perfect when you start. And you're going to screw up a lot, make a lot of mistakes, learn a lot, lose money at times. I mean, trust me, I've lost my share of money on orders that I thought were going to be good that turned out to be bad. But yeah, I'd add that to the list as well as as things. So it's not the idea, uh, and you don't have to be, uh, you don't have to be perfect and sell something first before you invest too much time or money.

Yeah. Is there, is there any resources or books or insights? Yeah, but mainly a lot of times books are usually the go-to that, that really just kind of like you keep going back to, that keeps kind of like, would say it's like the foundation all like, you know, like in my practice, like I'll tell everybody, you know, The Four Agreements. Everybody should own that. Great book, right? It's $9 most of the time on sale on Amazon. You know, there are certain like books that like, you know, if you start here, just like inform your philosophy, just start thinking.

Four Agreements as in The Four Agreements that were written in Cleveland in 1930-something?

No, the Don Miguel Ruiz book. Don Miguel Ruiz. Yeah. Okay. It's fantastic. It's four simple things. Right? It's be impeccable with your word, don't take, uh, don't take things personally, don't make assumptions. And what you just said, you're going to screw up, start over with number 1 again. Yeah, that's the whole book, right? I mean, it's more pages than that, but that's the gist of it. Yeah, right. But how, how simple, right? It's not a simple thing to do, but it's a simple thing to grasp. Doing it is the difficult part, right?

Always is, always is.

But, you know, so that's like a go-to.

And, you know, my go-to is been, um, a guy named Jeffrey Fox, How to Be a Rainmaker, um, which is really the simple principles relative to sales, uh, and it's this thick and you could read it in 2 seconds, um, but you know, he kind of just gives you a slap across the teeth with simplicity and like, you know, hey, pick up the phone and talk to your clients, like What do you mean? Yeah, you know, um, I love that. And then the other book that, you know, sort of helped define me is Dig Your Well Before You're Thirsty, which, if you're talking about The Four Agreements and say that's the whole book, uh, the title of Dig Your Well Before You're Thirsty is, is the, is the, uh, entirety of the book as well. And that's it. I mean, you could guess what it's about, but it's about building your network, for where you want to be versus where you're at today. Yeah. Um, and you know, I've done a great job of— I can't reach my back. I've worked hard here to, um, do that. So prior to being in specific decoration methods or having the business to give to bigger, um, companies. I've created relationships with people there, uh, without making false promises or expect— building expectations to make sure that when our time did come to need their services, they would pay attention to those orders. Um, having, you know, hey, uh, by this time next year, you and I are going to do this much business, and then you actually, you know, be true to your word. And, you know, that's, that's proven well for me. That's awesome.

That's awesome. So if people are, uh, one, looking to get some swag, but also learn more about you, where, where is everybody going?

Yeah, I mean, my email is jay@inkedstores.com. Anybody can contact me at any time. I keep it on my LinkedIn. LinkedIn, I post every day. And I write my posts. I write them. I actually don't— sometimes I'll leverage AI for some information or data, but generally the voice that's coming out has been handwritten by me. And yeah, I just like it that way. It doesn't give you— I don't have all the in-depth posts that a lot of folks do, but you get the real unedited spirit of what I'm trying to articulate. And, uh, um, yeah, that's just how I manage it. Um, you know, working on a lot of videos now like this. Um, yeah, I just try to be real, true. I'm always willing to help other entrepreneurs. I'm not looking for anything from it. I'm not— you know, it's funny, as much as I sell and as much as I love sales, I'm not salesy. You know, you contact me because you need help in your business. I don't need your business, you know, and that's a good position to be in. I want it. I want your business. But like, for example, like, I don't know if you produce swag. I haven't asked if you produce swag, and I'm not going to ask you if you produce swag. You know who I am. You want to do business, we'll do business.

Right.

Exactly. Right. So I, you know, I just try to be that. I, you know, we've all been around that guy.. And I try not to be that guy. And, uh, yeah, it's proven well in my life, and, um, I'm happy as a state of being.

It's pretty damn awesome. And you have this big awesome neon sign behind you for people who aren't watching the video version.

But, uh, the story of this neon sign is I was on a business trip and my staff bought it for me because they knew that I was too frugal to buy it for myself. I walked in, I said, please don't tell me you used my money for this. And they just like were like, we thought you'd like— I was like, I love it, it's great. So yeah, what are you gonna do?

It's—

was a nice gesture, and I'm appreciative of the people who work for and with me. And, um, they've been here a long time, all of them. Uh, I really don't have any newbies, nobody. I don't think I have anybody on the team that's been here under 2 years.

Oh wow.

And my longest tenure is 10, next is 7 going on 8, next is 5 going on 6. So yeah, people stay here a long time.

That's a great sign.

Yeah.

Well, that's a whole nother conversation at a different time in a different day about retaining like lifelong staff, lifelong team members. I'm a big fan of that and I see the turnover in all these different industries. It's tough. It's tough. And it's— it doesn't have to be.

My number one, I mean, I told the person who's been here 10 years, I told Kyle, I said, you'll either leave me or you'll either leave or I will close the doors, but I'm not going to ever ask you to leave. I mean, it's just not going to happen. She's been with me from the beginning, some definitely hard times and grind it. And I remember printing t-shirts with her. In fact, we had an order. Then we went to the last story. I know you're wrapping up. We had an order from the New England Patriots. Right. Who, by the way, have maintained— this is a challenge going— we made for them who have been a client for 10 years. And their special teams coach, Joe Judge, came into my shop on December 18th to order 50 hoodies, all custom made with names of the players, to deliver 3 days later.

Wow.

This is our first year in business, and Colleen and I stayed till 1 AM the night before they were due, barely know what we're doing, to finish the job. I mean, it's what it takes. Yeah, yeah. And it was the Patriots. I mean, we haven't— and we haven't, you know, we've been kind to them. Like, we haven't like put them all over our social media. We just did a big project for them this year, and I got their My contact said to me, he's like, Jay, I'm gonna send you pictures, put all over your social. I was like, that's great, that's great. That came from not doing that for 5, 6, 7, 8 years.

Yeah, it's the relationship first.

It's 100% more. So yeah, I mean, they're my client. They didn't— they pay me. They didn't ask for me to— I didn't do it for free. It's like, I don't ask them for tickets, you know. They didn't— they didn't ask to be promoted, so I just try to be respectful like that.

So that's integrity. And that's the beautiful thing about what I want people to hear at the end of the day. You can be happy. You can have a successful business. You don't have to be in a business. You can be working for a business, but you can have that and you can still be fully of integrity. And I think that's a beautiful, beautiful message to close with.

Nice guys finish first, Jason Wasser.

I'm hoping more and more and more that people get to see that and realize that.

Well, I think it's true. I think it's true.

So yeah, I'm glad you're one of those people that are out there sharing that message, and thanks. I hope it continues, and I hope you get more opportunities to hang out with people like me and do more of this. And I'm super stoked that we, we got to connect, and I really thank you.

I'll never say no to a free therapy session.

Well, totally, we can, we can make that happen.

No, I just said this was it. We don't have to make it happen. We just made it happen. The only thing missing was the couch. That's true.

I'm sitting on a chair. You're sitting on a comfortable chair. I guess it's close enough, but, uh, yeah, we'll make it.

Thanks so much.

Thank you.

Really appreciate it.

All right.

Thanks for listening to the You Winning Life Podcast. If you are ready to minimize your personal and professional struggles and maximize your potential, we would love it if you subscribed so you don't miss an episode. You can follow us on Instagram and Facebook at Jason Wasser LMFT 🎗️.