What If It Did Work?
What If It Did Work?
You Can Reinvent Your Life At Any Age
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You can be successful and still feel wasted, and that’s where reinvention starts. We talk with Jay Sargent, entrepreneur, coach, speaker, and author of Shift: The Gift of Reinvention, about what it really takes to change your life when you’re burned out, stuck, or quietly wondering if your best years already passed. Jay isn’t selling a fantasy. He’s lived the pivots, seven times, and he’s honest about the fear, the grief, and the discomfort that comes with starting over.
Jay breaks down the patterns behind career change and midlife reinvention: why titles don’t define you, why “no small moments” can redirect your entire future, and how a simple 15-minute ask to the right people can open doors you didn’t know existed. We also dig into why credentials are overrated, how real selling is just rapport and clarity, and how NLP reshaped the way Jay thinks about communication, relationships, and helping people move from hesitation to action.
Then we go deeper with stories that hit you in the gut and raise your standards at the same time, including his grandmother finding love at 92 and a 90-plus-year-old who keeps a yearly growth and development budget. If you’re in your 40s, 50s, 60s, or 70s and you feel “too late,” this conversation offers practical steps: do a personal inventory, name what you’re good at, and build a simple path from skill to business to freedom. If this lights a fire, subscribe, share it with a friend who needs a fresh start, and leave a review so more people can find it.
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Welcome And The Reinvention Question
SPEAKER_00I never told no one that my whole life I've been holding back. Every time I look my gun up, so fucking two foot stones here a voice.
SPEAKER_03Alright, everybody, another day, another dollar, another one of my favorite podcast episodes. My favorite podcast, because it's my own. I'm biased. What if it did work? Now, welcome back to my favorite show. Now, this is where we challenge fear, excuses, the comfortable little lies we tell ourselves every single day. This is a show that always asks that dangerous question. What if it did work? Today's guest, Jay Sargent, entrepreneur, coach, speaker, author of the brand new book, Shift. The Gift of Reinvention. And this conversation hits home for anybody who's ever felt stuck, who hasn't, burnt out, who hasn't, overlooked, all of us, or wondering if life already passed them by. It hasn't, people. Jay talks about living seven different lives through multiple careers. This guy reinvents himself more than Cher, more than Madonna, from tennis coach to entrepreneur to leadership mentor. But this isn't one of those fake social media guru conversations where somebody magically becomes successful overnight while sipping alkaline moon water in front of their rented Lambeau. This is about reinvention through courage, discomfort. Oh, discomfort, Jay. Come on, man. Adaptability and realizing that no season of your life has to be permanent. If you can't, if you've ever asked yourself, can I start over? Am I too old? Did I miss my shot? Can my next chapter actually be better than my first? Then buckle up because this is the ultimate rock star. How's it going, Jay?
SPEAKER_02It's going great. You know, I am 78, and when I wait- You don't look it, you don't look it, brother, or sound it.
SPEAKER_03I just want you to know. I don't know it's because you live in off the west coast, and maybe that's the reason.
SPEAKER_02You know, every morning when you're 78, you wake up and you touch the ground and you take a breath. It's a blessing, and I'm grateful for it. And you know what? I've reinvented myself Omar seven times, but you and I are on the eighth reinvention right now on this broadcast, because I've chosen to build another business off of this unexpected book that ended up in our life, you and I shift the gift of reinvention. And I say it was an accident, Omar, because I have three daughters. I have a 54-year-old daughter, a 37, and a 34-year-old daughter. And God bless them, they all live in the greater Los Angeles area. And they come over to the house periodically, not often enough, by the way, but periodically, and they say, Dad, we got grandchildren who will have children of their own. You've been telling us these stories forever. You've basically blessed us with these stories, but there's going to be a great grandchild who doesn't know you. Can you write these things down or transcribe them in some way? And that's the beginning of the book, Omar.
Why Jay Wrote Shift
SPEAKER_02All I wanted to do is get the big, funny, wonderful moving. I know you read the book. There are moments in the book that are funny, and it's a quick read, thank God. But there are moments in the book, I imagine uh most people have a shed shed a little tear because I just describe how I lost my wife at a pivotal moment of 28 years. But in any case, I wrote the book for the kids, and then some then a big surprise happened. Because as I was writing the book, I realized, gee, I've reinvented myself seven different times, and there's some patterns there that I think I could teach anyone who wants the second half of their life to be the best half of their life. Anyone who's stuck in a moment, anyone who's at a job or in some position, and they're wondering, I wonder if this is the only thing left for me to do. Is this really the last chapter? And I say no, it isn't. I say no, it isn't. And so, anyway, it was a joy to uh bring the book to the world. It's only three weeks old. So uh I with God's blessing and your help, maybe we get some more people reading the book.
SPEAKER_03For sure, because what I love about it too is it talks about reinvention. Who doesn't want that? Everybody has that pivotal moment. I know you're blessed with being an amazing woman, but so many people feel like especially okay, now it's the end of school year. You know how many people are like, Yes! My kid graduated, my last one, I can finally get out of this marriage. And it's like, are you for real? Or are are we in in like some country where you can't just make a choice or that you can't co-parent? And a lot of times they create this fictitious story that oh my gosh, if I do leave this job, if I leave this marriage, if if I actually start a business at 50, 60, whatever, it's not gonna work. And it's like, but why? And everybody always talks about, and this is what I love about your book it's not about luck, just it's a decision. Decide, commit, and move your ass. Right? You had to do it set eight times. Imagine if you're like, yeah, man, you know, it can't happen again. Because that's how the people live. When when when you hear you're like, oh my god, you stayed at that company for 30, 40 years, you must have loved being there. It must have been so empowering. And and then you find out he's like, no, I had a calendar, I hated every single day. And it's like you wasted your whole life doing that. Yeah, but but there was nothing else out there. Because you always hear that, right? Oh, there's who or who who who's gonna want me? It you know, I'm I'm single. Uh I was married for 20 years, almost 20 years. So imagine if I'm like, oh gosh, I'm thinking about just going to seminary school. Technically, I'm Catholic. I I never got married in the Catholic church. I could legally be, you know, there's always loopholes. Maybe I can just become a priest. Right. Or you know, uh people always play the violin and want to go with the theme song of Titanic when it comes to describing their current situation. You bet. You bet. It's just everything, whether Jay, you and I could have been have I I social media sock you, you're doing amazing. Pickleball. So you you you and I could be like the pickle ball stars, you know, and say this is it, man. This is as good as it gets. But people don't realize the great or even the bad, it's just temporary, man. You you you you can't you can't live holding on to like even a title. Look at all the things I I said that you were, man. Like literally, there's Jay, there's Cher, and there's Madonna. But you you also realize all those things are just a title. That's not who you are, Jay.
SPEAKER_01You bet. You bet.
SPEAKER_03If I if I asked your daughters, they they wouldn't be like, well, dad was an entrepreneur, he was involved with leadership, he he's an author now. No, no, the the I I've had plenty of Buddhists, and that's that's the one thing they talk about. Yeah, and I'll have to agree, man. I I don't oh, but you're you're a dad, you're an entrepreneur, you're this, you're those are all titles, man. That doesn't define, and people hold on to things like well, Jay, I can't reinvent myself. I've got I've got totally vested. If I stay here five more years, I'll get two extra vacation days.
SPEAKER_02You know, Omar, I can only work with people who have a certain hunger. And I've got to be really clear
Titles Change But You Don’t
SPEAKER_02to everyone who's listening in. I didn't just reinvent myself from a position of weakness. I'll give you a quick example. I became a tennis pro, then I owned a tennis camp, then I owned a tennis academy, and I became one of the leading tennis instructors, put kids on the national tour, put kids into the pros. And at the height, in 1977, at the height of my career, when I had 34 pros working for me, a summer camp, an academy, a stringing operation, a pro shop, and I was making six figures as a kid in short pants. One day I said to myself, I'm being wasted. I don't, I'm not enjoying this anymore. I have no threshold for psychological pain. Omar, I can take a punch. Do you understand? But when it comes to emotion, when it comes to emotional pain, I'm out. And on the day I didn't want to do it anymore, high as a kite, up as good as I could get in what I was doing, I needed to do something else. And so I'm going to give someone out there some practical advice. On that day, I did one thing that everyone can do. Everyone can do it. I called up five people over a 48-hour period of time. The most powerful, they happened to be wealthy because I was teaching very wealthy people. Robert Kraft, the owner of the Patriots, had taught his whole family. Little uh, you know, the kid who's the president was in my tiny tots, four to six-year-old group a thousand years ago. I called up five influential people and I said, Would you give me 15 minutes? I know how important you are, but can you meet with me? Can I come to wherever you want me to come? Can we we spend 15 minutes? And of course they all were very gracious. They said, Jay, whatever you want. When I got with them, Omar, I said, What am I? You've watched me for seven years with your family, with your children. What do I do next? If you're me and you're done with this, can you help me out? Tell me what I should be. And by asking that question, someone set up a meeting with a guy named Mark Roberts, family owned the largest steel company in New England. And one night he invited me to a cocktail party. And I sat next to who knows, I didn't know the guy next to me, but the guy next to me was Mitch K. Poor, the developer of Visiplot, VisaCalc, eventually Lotus 123. This is 1981. There were only three pieces of software in the world: Lotus 123, the beginning of Microsoft, and Ashton Tate's D Base 2. I'm sitting next to him and I'm saying, I have a small, and at the time, Omar honestly failing franchise development company. What do I do next? What would you recommend in the space that you uniquely understand? And at that moment in time, this is a concept I call there are no small moments. He says to me, Jay, there are 2,000 computer lands selling the beginning of microcomputers. Whoever puts a software retail store across the street from one of those computer lands will make a small fortune. They don't exist right now, but you should develop that, in my opinion. Now remember, back then no one knew about computers. There wasn't even IBM didn't even have a PC back then. I got that information and I didn't have a lot of money at the time. So I want everybody to understand this. I took every dollar I had and I bought plane tickets. I found out there was one in Boston, a little store in Boston, one in Washington, D.C., one in Chicago, and one in Los Angeles. And I got on an airplane and I cold called all four of them. Thank God I ended up in LA on Pico Boulevard, and I saw the best of the rest. And the one unique thing about this store, Omar, was it was full on a Saturday afternoon. Now all they had was Ataris, Commodore 64s, Trash 80s, and Apple and Apple IIEs. But all the copter heads, all the Caltech, you know, freaks were there playing Pong, right? And I walk in and I go over to the blonde kid at the counter and I said, I am a master franchise developer. I can make anyone king in a category. I need to talk to the owner of this facility because this is the best retail store. Let's franchise it. And the kid turned, it looked like a surfer. He says, Well, I'm a part owner, but not a decision maker. And he sent me to George Tate of Ashton Tate, one of the largest, well, one of the only three software developers. And on that day, on a yellow pad of paper, I signed a contract to be the exclusive franchise developer for one company store. In 18 months, we sold 154. But if I didn't go to that cocktail party and I didn't talk to that guy, and I didn't respond to that information, and I didn't take the few thousand dollars that at that moment I had and invest it in a trip which was highly speculative, and then go and
No Small Moments And Big Asks
SPEAKER_02have the Gouliones. You know what I'm talking about. I had to say to that kid at the counter, I'm a kingmaker. Whoever I choose in this category to make the number one software retail store in America, I'm gonna do it. Who do I talk to? All of those pieces are available to everybody, everybody. I didn't have a background in that.
SPEAKER_03So, anyway, so that's part of what I'm sharing with people, and I love that because you and I not only are we kindred spirits, but I agree, I agree, Jay. There are no small moments, just this belief that just minor opportunities or conversations, that's what people don't realize. They alter, they completely alter someone's future. You don't know who you're gonna be introduced to, so clearly go out there, don't be stuck in your friggin' living room thinking you're gonna meet the next Steve Jobs, a podcast appearance. You're you're gonna laugh. Is it random? No, it's not. Did you know somebody wanted me on their podcast just because they saw uh I I would do videos, which I still do, but they they loved them, and it was someone out on the west coast. They actually, movie producers, uh screenwriters, they had me on a podcast. Next thing you know, I wrote a couple of books just based out of that and have my own podcast. So you literally don't un people don't understand what seems small is only small because they're not open up to the possibilities.
SPEAKER_02Oh, I love that point. I love that point. I want to go to my second point, Omar. Go ahead.
SPEAKER_03Jay, you can go to as many points as you want, brother. Okay by all means, people get stuck by not moving.
SPEAKER_02My I want to reiterate that first piece of advice. There are no small moments for God, just you said it so well, Omar. You can't sit in the living room. Take a bad gig to find a good gig, but get into activity, move for God's sakes. But the other big stop and the pattern that I see is people will tell me, I don't have the background, I don't have the credential. Now, you're watching me here. I'm wearing my former tennis outfit and now my pickleball instructor outfit. I'm 78, one month away from being 79, and I'm teaching 14-year-old pickleball champions who are now on YouTube playing on the tour. I can no longer stay with them, Omar. Let's be honest. I mean, I have brother.
SPEAKER_03I'm I'm I'm gonna be 53 in two months, and I'm not gonna blow smoke up your ass, Jay, and say whoever said age is just a number was some young 20-year-old who was full of shit and just came up with that saying, No, age is I I I'm with I'm with you 100%, Jay. Uh so yes, I I I feel your pain.
SPEAKER_02So when I met with those folks, I'm gonna tell you how I got into franchise development, and this is very important because this is under
Credentials Are Overrated
SPEAKER_02the title of credentials are overrated. And again, I don't want to be caught up in this. It's not that I'm not for education. All three of my daughters went to wonderful schools. Two of them got great, great backgrounds in what they're doing. One of them, we could have saved the money because what she's doing right now has nothing to do with what she did at university, but she's very happy and very successful. But on the day I got a meeting with George Nanaf. Now, I want everyone to know George, God rest his soul, is in heaven right now. But George was the most important and powerful franchise developer, maybe in the history of the United States. I could give his whole background, but just take my word for it. A major player in franchise development. Someone set up a meeting for me to meet with George. I walk into his office, and it was the combination of he was the Pope, he was a Visigoth. I mean, it was a massive, intimidating presence and office. I go sit down in front of him, and he says, I hear very good things about you, Mr. Sgt. You've been highly recommended. You know I sell franchises. I'm developing my own franchise chain, and I'm looking for people who can go on the road in beautiful hotel rooms and sell quarter of a million dollar franchises. Can I see your resume, please? So I say, Omar, on that day, I didn't bring a resume because I don't have a resume. He said, Oh, that's curious. Well, why don't you walk me through your business background verbally? And I said, Well, I have no business background. In fact, I don't like business. In fact, I've never read a business book or a business magazine. The last thing in the world I would do at the airport, I'm reading Sport Magazine, but certainly not fortune. There's not of any interest whatsoever. So now he's sitting there, he's stunned.
SPEAKER_03He said, Well, I because you were honest, Jay. How many people would have the balls to to ask? Because human nature says, Oh my god, I'm gonna friggin' wing it and look like a complete fool. This guy's gonna see that I'm a liar and right and not trustworthy because you're lying. So, how how can you we trust you? You're like he was shocked because you're like, hey, so so man. I I I love reading Sports Illustrated when I'm flying. I'll read Fortune magazine Forbes with Forbes.
SPEAKER_02So then he says to me, Well, how can I hire you to go? I'm gonna spend a fortune to put you on the road, put you in Wall Street Journal ads, put you in the finest hotels, and I'm gonna have a big investment in every trip I would put you on. Why would I hire you? And I said, George, I am told that you sell franchises by someone standing up in a beautiful hotel setting and giving a speech. Is that true? He said, Yes. I said, Well, you are meeting right now the greatest speech giver of all time. And here's what I'm gonna do. I'm gonna prove it. Give me your brochure, it gives me a crappy little three-fold brochure about the franchise offering. I put it in my hand and I say, I'm gonna go into the lobby, and in 15 minutes, I'll come back and give a presentation of your franchise opportunity. Put all of your Goombas, put all of your sales force, the very best people in there, put your managers, your owner, put everybody in this huge office of yours, and I will give a presentation. 15 minutes later, after reading the brochure, I come in. Now, I gotta tell you, what God gave me more than hair late in life, because most of my relatives are bald, but I got hair, yay, and I got. The gift of Gab. And I have been giving speeches since I was in single digits. So I have, although I had no business background, I have supreme confidence in shaping a moment, telling a story, moving my hands, firing off spatial anchoring, all of this good stuff. I just know that. I give this speech. I don't say one thing that's accurate, by the way. No, I completely destroyed the content. I can feel the anger of his sales force wanting to assassinate me. Do you understand? I'm feeling that they want to kill me. At some moment, and I but I know I have an audience of one. At some moment when I'm done, he throws everybody out, says, Come here, kid, sit down. He said, You didn't say one thing right. Everything was backwards. There wasn't any accuracy, but boy, was that a good story. And you can rock. We can clean up the details. You're in. So all I want to say is on that day, I was the ultimate no credentials. I don't buy from anyone. I'm not worthy. I don't have the credentials. If you dig into who you are and do the proper inventory and understand how valuable you are, in some way, shape, and form, you're going to create a reinvention, a potential reinvention. So that's my second insight, uh, Omar. What do you think?
SPEAKER_03But you want to know something? Sure. The sales force that wanted to crucify you, you know how to sell. It's all about connecting. Because if you can't connect, you cannot solve any issues, you cannot solve any problems, much less sell something. You see, those people are used to vomiting all this bullshit information on people. When somebody just wants three, give me just how is this gonna solve my problem? Give me three bullet points. Because a lot, oh, here, here, let me show you how smart I am, let me show you how informative I am. And that's why you you the if what you told them was like nails on a chalkboard, but they don't realize you sold them, you connected. He didn't give a shit because you you had you could connect, and that's that's the the number one thing that people don't understand when it comes to selling is all you have to do is connect with someone on on a just one-on-one level, and you can s you you can make the world go round because sales is about connecting. Connecting is what moves mountains, not well, I know this, or oh, I I I I read 10 Zig Ziggler books and Grant Cardinal books, so I'm and I have a certification. I am certified, yeah, I can sell you this car, but I don't want I don't I don't have a license, but I'll still sell it to you.
SPEAKER_02Oh my, you don't know how you just stripped the switch. Your comment just right there gives me a pathway to a really fascinating part of this conversation. So God bless you. Thank you, brother.
SPEAKER_03Go ahead, brother. This is this is this is a shared that we're in a safe place here, brother. Go ahead, man. Go go
The Poolside Pivot Into NLP
SPEAKER_03that that's why we're have that's why there's no prefabricated questions or anything, man. Because we're we're just we're we're two connected souls riffing, like we we've known each other for years.
SPEAKER_02Omar, again, at the height of success, after I had sold 154 franchises from scratch, somebody bought the company and didn't want a franchise division, and they shut us down. In the biggest quarter I ever had in franchise development, I sold 60 quarter of a million dollar franchises in a quarter, in a three-month period of time. On the heels of that, I get called into Century City here in Los Angeles, the big buildings where all the lawyers are, and I get called in and they say, Mr. Sergeant, thank you for your service, but we are shutting the uh retail software division down. We don't want to the own the new owners don't want to own a franchise. So thank you very much. In that moment in time, that was I gotta tell you, that was a painful moment. I had saved some money, I had a little bit of money in my pocket, but not enough. And I had a brand new bride. I I had just met a gal at a coffee shop, OG, which is the word in Italian for today. It was one of those original before Starbucks coffee shops that actually had real gelato and a real espresso. And I met this young woman and I fell in love and I married her. And she was only 21-22 when we had this reversal of fortune. And I called up George, who I had left, who I had betrayed in a way. He was so honorable. He said, Jay, form your own company. If you ever fall down, scrape your knee, the light will always be on because I knew from the day I met you I was renting you, leasing you, not owning you. So God bless you. If you ever have a problem, remember Uncle George. So now, years later, on the heels of these huge victories, but now this reversal of fortune, I give George a call, and he was as gracious in that call as he was when he said goodbye to me. And he said, Oh, kid, you don't know your timing here. I have just raised millions of dollars to create the ultimate new chicken franchise, Boston Chicken. And we're gonna we're gonna have it based in New York in Manhattan. And you're calling me, I want you to be the president, I want you to lead the franchise division, I want you to grow the chain. I will send you $10,000. When $10,000 a long time ago was a big wall, I'll wire your money, I'll get you furniture from the west coast to the east coast, I'll put you up in mid-Manhattan at the Roosevelt Hotel for as long as you need. I'll find you a place. This is the great, this is a great moment for us, kid. I go run to the new wife. Remember, she's a kid. I'm 37, she's 21, and I say, Sweetie, we got a stable position. We got money in the bank. The guy's gonna New York's the most exciting city in the United States. At the time, I was a big opera guy, so I'm thinking, oh, we're going back to where there's culture and all of this. This will be fun. I'm gonna bring my new bride. She's never seen New York, it's gonna be great. Two days later, I'm ambivalent. You know what ambivalence is. All of a sudden, I'm thinking, do I want to stay in franchising? And do I want to build a chicken empire? Is that my destiny to be the king of chicken? I don't know, you know, and it didn't it didn't fit. I just knew it didn't fit. I say goodnight to Lee, who's now in heaven, but I say goodnight to Lee that one that night, and I go down to an Olympic swimming pool. Massive, I'm in a transitional place called Oakwood Garden. You can get one month uh facilities because we're leaving town. I go to this massive Olympic swimming pool where there are 250 shage lounges around it, and I'm sitting there and I'm steering into the water and the sun, the moons above me, and I'm in between trapezes, floating in space, trying to figure existentially whither thou goest. And a bald-headed Jewish guy in Bermuda shorts with a baseball cap sits next to me of all the seats, 250 empty seats sits next to me. And he says, A penny for your thoughts. And I said, Well, wait a minute, you're in trouble. Because next to the word loquacious in the dictionary is my picture. There's no such thing as a short form of me. If you want to really know what I'm thinking about, it's gonna go for is that okay? And he goes, I got nothing but time. Tell me what's on your mind. I go for about 10, 15 minutes, and he stands up and he disappears. And I think, ha, I bore the living daylights out of him. But he comes right back and he comes back, and this is where your tie-in, Omar. You're gonna love this point. He comes back with a well-worn book that the spine's been busted because it's been opened so many times. There's notes on every single page, and it is the seminal original work of John Grinder and Richard Bandler, the developers of NLP, Neurolinguistic Programming. It's called Frogs into Princes. I've never heard of this technology before. He hands me the book and he says, read this book. And I said, Well, how lovely. Can I give you money for? He says, Do you want he says, No, no, no, you don't understand. It's a gift, and I want you to read it now while I'm with you. So I read the first, he says, This is what you should do with the rest of your life. I go, okay. I read the first 11 pages. I've never been more excited to read anything in my entire life. It reminded me, this will be a reference that nobody, my unless you're my age, will understand. But when I was a boy, there was a novel by Harold Robbins called The Carpet Baggers that had a few little sexual parts in it. And as a little boy, it was one of the most thrilling reads. I was remembering in those first 11 pages of Frogs and the Princes, oh my God, this is so exciting! I turned to say thank you to him, and he's gone, and I never saw him again. Never saw him again. I got the book, I run upstairs to the bride, Lee, my little Lee, and I say, Sweetie, we're not going to New York. She goes, Really? We're sending the money back. I'll call George tomorrow. I know he's going to be upset with me, but at the end of the day, we're staying in LA and we're going to take the information that I've just read in this book, and I'm going to build an empire from sharing this information. Because this information will set people free. And the information is really clear, Omar. All NLP and sales technology means is it's not about closing skills, it's about building rapport, building a relationship, understanding the other person's real deep, profound wants and needs, and figuring out if what you have to offer matches them. And I went from and remember, I want I want our listeners to understand why I'm saying this. Because I had the cushy job, I had the security of the money in the bank, and I had the backing of one of the great men in the category that I knew really well. And I completely left it because I got passionate about sharing that information. And I won't bore anyone with it. I closed a $5,000 deal with a buddy of mine who owned a Miracle Auto Paint in San Francisco, a car painting company. I got my first $5,000 gig and eventually created $11.2 million worth of sales training and consulting out of that night at the swimming pool. But remember, it was an some people would call it a risk. For me, it was it was the only option.
SPEAKER_03Yeah, but you know what? I realized reading your book though, you had the foundation, just like your daughters. Your daughters have a foundation just based on seeing you, your drive, seeing your hustle. That entrepreneurial mindset, it was always there. You even credit your parents just watching them. They're not only their entrepreneurial spirit, but just their work ethic. And now work ethic, we can all go to gurus and read all the personal and business development. Unless it's instilled in you at an early age. That's not like that, that's like something that if they could bottle it up
Borrowing Grit From His Parents
SPEAKER_03pharmaceutical company, it would be a trillion dollar industry if we could give people drive. And you you have it.
SPEAKER_02And my folks, for the first five years of my life, couldn't afford their own apartment. So we lived in a very small apartment with my maternal grandparents and a maternal aunt, all of us in this little apartment. And my folks would get on a streetcar because they couldn't afford a car, and they would drive to uh take a streetcar to downtown Boston and go to department stores, and I'd stay with my maternal grandmother. And two things that I want people to note. I model NLP, neurolinguistic programming, teaches us to model expertise. And I have two forms of expertise that I want to share because Omar, I think people can borrow my parents. I'm gonna lend everyone my parents right now. My parents never made it as entrepreneurs, they never became millionaires as entrepreneurs. But here's what they taught me, and here's who they were. And it and it was a very curious thing because when I eventually went to Boston College, wonderful Jesuit school in the Boston area, and I started to meet other people who were wealthier than me. I got invited to the Bedford family, the Belford family Christmas event in my freshman year. I went to Long Island, and two things happened. You'll get a kick out of this. I went to the first big meal where it was quiet. So I'm sitting around the Belford Christmas table, and it was a quiet event. And people started to discuss stock portfolios and investment strategies. To this day, Omar, I remember that little 18-year-old Jay at that table going, I'm completely screwed. I'm never going to be powerful and rich because look what they're learning from their parents. My parents have never had a dime in the bank, don't own any stock, don't know any investment strategies. That was my original thought, but Omar knows differently. Because what my folks gave me was a bigger gift. My folks were dreamers. They were desperate to move up in the world and have more. And they were willing to take one risk after another. So in my little apartment, my folks sold shoes, gave cha-cha and mambo dancing lessons. My Jewish mother taught Chinese cooking classes, and they sold glass, they sold ties. They did anything they could. And in one fateful event, I want people to have a frame of reference here. My father had two jobs. He delivered newspapers as a teamster at night, throwing the bundles of newspapers in front of drugstores when people read newspapers. And in the daytime, he walked for the worked for the Boston redevelopment. Two jobs equaled $7,000 a year, is what he earned. They got their hands on a set of clowns, tragedy and comedy clowns. They bought more than you can imagine of these clowns, rolled them into canisters, and my dad and mom put a $500 ad in the New Yorker magazine. And we all, on the day it came out, ran back to the house to look at the mail slot. We thought we were going to need buckets to pick up the mail from the orders for the tragedy and comedy clowns. Three. We sold three. That was the best day we ever had. They basically burned all of that money. They never moved that product and they lost obviously the $500. But I can guarantee you, the day after that was over, they were on to the next. So I learned from them not financial strategies, not stock portfolio management, but I learned the kind of courage and optimism and the ability to get up again and get up again and get up again. And I'm going to give a shout out to my mom. My mom walked, and this is for everyone who says they don't know what business they're going to build, what credential. My mom fell in love with a kind of art glass on Cape Cod called Sidenstricker glass. Bulls and cups and beautiful things. And she went to the owner, a guy named Bill Sidenstricker, and she said, I love your product. I love your glass. We don't have any money, but we love what you have. And we want to, if you'll do this, put the glass on consignment. My husband Bernie and I will put it in our car. We'll drive to Boston and we'll develop a market through little trade shows, through the Hadassah ladies, through volunteer groups. We will schlep your glass every place on God's good earth. And that glass business, everyone listen, put my brother through four years of Harvard University with a dollar of without a dollar of debt. They paid down the entire Harvard education. Now it wasn't the hundred thousand dollars it is now.
SPEAKER_03Of course, of course. But it was at every school these days, Jay. It's not just Ivy League. It didn't go with inflation, it went way past inflation.
SPEAKER_02I got a grandson going to Fordham next fall, hundred thousand dollars a year to go to Fordham in New York.
SPEAKER_03Oh, my my youngest starts bandy in August. And yes, that's that's the going rate. My my oldest is at LSU because uh a legacy like me, and she got like if out of pocket for a state school in Louisiana, forty-five thousand dollars a year. And it's like if if that's not a business, your your your parents would smirk and say, if we could do it all over again, we we would start a school because those loans are unforgivable, and you just even and it doesn't matter because academia brainwashes people into believing that if you don't you don't have one of these babies, you're you're gonna be destitute, you're gonna be out, you're gonna be doing tricks somewhere, you're you're gonna be selling drugs, you're gonna be doing like this digging ditches, and it's the furthest thing from the truth, but it brainwashes people because I I believed it that uh oh my gosh, if I if I didn't go to college, and then you're gonna laugh at this, Jay. Uh I I was depressed because I was heartbroken. My my first relationship, she broke my heart, and my mom's like, you know what will heal that? Go get a master's degree. Now my mom's got a a BA, so it's not like she has any frame of reference, but she's like, okay, that sounds like a great idea. And it was this the most horrible idea because I've got two degrees and things that that and two dollars and fifty cents will get me a copy of the USA Today.
SPEAKER_04That's it.
SPEAKER_03And it didn't, it did not it never cures heart, heartache, or heartbreak, or anything like that academia. If anything, I learned how to get treated like shit by people with doctor degrees in something completely useless, and it's like, yeah, so yes, that that's another topic for another day, Jay. But yes, so you you and I would agree you you the the drive, the work ethic that your parents had, that produces success because you and I both know there's plenty of baristas out there with degrees from some pretty noteworthy institutions.
SPEAKER_02Yeah, I'm not gonna, I think it's a little swarmy for me to say it, but I will say it. My my oldest daughter went to Colombia and her two best friends, both from the working class, so their folks kill themselves to be able to afford Columbia. They're both here locally, very happy, by the way, but they're both yoga instructors. Did they did they need the Columbia degree?
SPEAKER_03Yes, they did. They did, they needed to go to New York City for that.
SPEAKER_02Oh my god. So, last but not least, the last thing I want to share with you because I believe it is never too late.
SPEAKER_03And then Jay, you're gonna laugh. That was my next thing. I I was gonna tell you what I got out of it is you and I, it you're not expired. I I'm not expired going 53, and you're not because I I I looking at you, brother, you you must have like a painting somewhere that ages. Because I I thought you were gonna be a lot older looking, and I can tell. The Grim Reaper, when it's your time to go to heaven, you're gonna be like, no, I still have to reinvent myself at least two more times.
Proof It Is Never Too Late
SPEAKER_03Come back 10 years from now, possibly. But go ahead, brother. I know it's never too late. Here's your fourth.
SPEAKER_02I'm gonna finish with my favorite story about certainly about not too late. I was raised for those five years when my folks went off to the department stores by my maternal grandmother, Nana Lil. And Nana Lil was an old school grandmother from the old country. So, you know, you got whacked, you got stuffed in a closet, you got your mouth washed out with soap for nothing. But I loved her dearly, and she was an incredible soul. And when she lost my Papa Jack when he was 75, and she was approximately almost 70, she went through his effects and she found a little book. He was a very sweet, too sweet, too gentle man who owned a dinky little hardware store in Lexington, Massachusetts. I mean, maybe the size of my room here. Honest to God, it was that small, very small. And when she went through his effects after he passed, she found a little book of debt. Construction workers, contractors had used his good heart to borrow equipment, nails, everything from him. He'd write it down in a book, you owe me $18, you owe me $32. This is a long time ago. These were big numbers back then. She opens up the book and she realizes they took advantage of his good nature. It irritated her to no end. And at nearly 70 years of age, now we're talking about in 1958, 1960. So another world, she goes and gets her first automobile license. And the reason she gets the license is only for one reason is to drive all over the city of Boston with that black book, knock on a door and say, You took advantage of my Jack. She'd open up the door, and a wife would come out and she'd say, I'm Lillian Jacobson, I'm Jack's wife, go get your husband. This is a shame. This is an awful thing that happened. The husband would come, she'd say, You owe him $14.23, go write a check. She collected every single dime that was owed to my grandfather Jack. That's number one. Now we fast forward. We could not, for the life of us, get that lady to get out of her little apartment in Brighton, Massachusetts, and get into a rehab center. And she was falling and she was injured and it was heartbreaking. And we eventually, my mom and I, convinced her to go to a rehab center. I didn't get a chance to see her for the first 30 days she was there because I was already a grown up and I was already on the road doing something, selling businesses, undoubtedly. When I went to go visit her at the rehab center, thinking she's going to be irritated with me, I go in and she goes, Jay, why didn't you fight for this earlier? This is the best thing that ever happened to me. She was then about 92 at the time. We play bingo, we've got movie night, there's three square meals a day in the middle of the day. We got a muffin, we got a cupcake, there's a lovely group of people. I'm playing cards, I'm playing bingo. I'm I am shocked. And then she leans forward and she says to me, Sweetheart, there was a little boy in Dorchester, Massachusetts named Louis. And when I was in the second grade and he was in the second grade, I had such a crush on him. And then we moved from Dorchester to Brighton, and I never saw him again. Louis is here in this facility. And Jay, we are falling in love. I said, Nana, you're falling in love. She's 92. She says, This is it, Jay. She found her Romeo and Juliet experience in a rehab center at age 92. She said, Louis comes up before dinner or after dinner with a little napkin, and he has captured a muffin and is bringing it to me wrapped in a napkin, like it's the Hope Diamond. It's a precious gift that he's giving to his beloved. And I and I'm watching this and I am stunned with the intensity of the romance and the passion at this stage in her life. Now I'm going to fast forward to a poignant moment. The last time I saw my grandmother, she was she lived to like 97, 98. I was already, unfortunately, in Los Angeles. I had already moved here, and I went back to go see her. And I go into a courtyard and she's sitting side by side at four in the afternoon on an October getting chilly afternoon with Louie by her side. Now they got the walkers in front of them, and they're holding hands side by side. And I have this lovely visit with them for an hour and a half or two hours. I give them a kick, I give her a kiss, I give them a hug, and I leave. And when I left, I could see them. They couldn't see me. I was on a walkway and I looked through a window. And the two of them, because it was getting chilly, stand up with their walkers, they waddle with their walkers, and every three steps they couldn't contain themselves, Omar. They'd stop and give one another a little kiss. Then they'd waddle again and give one another a kiss. And it was the purest expression of there is always time to just like you said, to decide to change, to embrace a new chapter in your life, to reinvent any aspect of your life. And so I hold that in my heart. I hold that experience in my heart.
SPEAKER_03It's an amazing story, Jay. Now, for grizzled people like us, what advice would you give somebody in their 40s, 50s, 60s, even
Inventory Your Strengths Then Scale
SPEAKER_03their 70s, who feel like they've missed out on life? They missed out on that golden ticket, they missed out on their opportunity.
SPEAKER_02Number one, the first thing that I say is do a personal inventory. What are you good at? Now, you know, I'm no good with numbers. If you open any of the drawers in this office, it's the wreck of the Hesperus. Do you understand? I have no attention to detail whatsoever. But I have words and I have the ability to tell a story. And I know that. So throughout all of the various reinventions, that's been the throughput. I always say to people, what do you know and love about yourself? What are you good at? And where might you find an opportunity? Today, my wife challenged me. I God bless my wife in Heavenly sent me Jessica. She told the kids when she was passing, I'm gonna, your father's a married man. He loves to go to the supermarket with a wife. He's gonna need a wife, he's gonna get remarried. I'm gonna send an angel when I send her love her on her deathbed. That you know, near her deathbed.
SPEAKER_03That's pretty that's that's that's a beautiful story, believe it or not.
SPEAKER_02So at some moment in time, my wife now said to me, Jay, how do you apply what you teach to just an average person, not a big storyteller like you? And I'm gonna give you a perfect example. If somebody is in Akron, Ohio right now and they're very good at installing floors or windows, whatever they're doing, they're either gonna install floors or windows for the rest of their life, or they're eventually gonna own a business that installs windows and doors. They're either gonna do the work or they're gonna promote the work and then develop, get one truck, then two trucks, look 10 years down the road. Could you have 10 trucks by not becoming what you can't become? A pig isn't a bumblebee, it isn't gonna fly. Whatever you're valuable at, whatever you're doing, imagine a life where you do it very well and then duplicate yourself. So instead of just doing the work, promoting the work, learning how to promote the work, and then create some kind of a business out of that. It can be as simple as that, but you know what? It needs hunger, it needs ambition, and it and as you have identified, Omar, it needs guts. Sometimes you gotta spend a few bucks you don't have, sometimes you gotta do things that scare you a teeny little bit, but people can make those breakthroughs. I've seen it over and over.
SPEAKER_03Jay, your story, this whole book should could have been called balls. People would think it was a story about baseball or tennis, but literally, I don't know why people feel like like they're a neuter dog, man. I I mean, Jay, you had balls to do it. Your parents had balls. Oh, but you know what? If it didn't work, you had the balls to do it over, do something completely different. People wake up one day, realize, oh shit, this regret, you know. Why can't people just fucking do the ball do the work, man? You said it best, you know. Oh, oh, well, well, well, I've I've I've got this two vacy two weeks of vacuum. Who cares? You know, when you go to heaven, when they visit your wife before that, yeah, but you don't understand, man. I I had I could have lived my life to the fullest, but I accumulated PTO. And that's that's what literally anybody, I don't care if you're 20, 30, 40, this book should resonate. This book will hit someone in their soul because at the end of the day, man, it says it best because you know what? People will look at the cover, or people will read the show notes and oh that this map for talking about this and that, but he was born wealthy, or or you know, such bullshit, or he was born with a horseshoe and is up stuck up his ass, and it's no MFR. That's the stupid bullshit story you tell yourself. So you can sit on your couch. Right now, there's people out there, they have time to watch four hours of Netflix today, tomorrow, the next day, next weekend, but yet they don't have time, they don't even have an hour to to to to do the work on themselves and go, hey man, this isn't the life. I I know God didn't make people to have crumbs of success, correct, Jay?
SPEAKER_02A hundred percent.
SPEAKER_03That's why your kids it's a direct line from your family, brother. You have we have okay, so what you don't have the foundation, but there's stories like yours, there's stories in general that say, hey man, like life is meant to be lived, life is meant to go out, life is meant to write a book. Because you know, some I'm sure some idiot out there, oh Jay, uh, you've had so much success. What's what's the point? Or maybe just just make this a memoir and you can give it to your great grandkids and they can read it, and they'll be like, screw that, man. Jay, at the end of the day, this book that you wrote is for that person that at 40, 50, 60, 70. Yes, we might be playing the back nine of our lives, but who gives a fuck?
SPEAKER_02You still have plenty of time to do something, and you got all those resources you created in the first half.
SPEAKER_03Of course, of course, and if somebody's like, well, you know what? Starting over is a gift. Because imagine, Jay, no, you're not lucky, but you you had that hunger because you know what it was like living like that. A person, you know, the Vanderbilt family, they lost everything after like one, not even two generations because they didn't, they weren't like Cornelius. That and I guess Cornelius didn't instill that drive in his family. Your your family wanted to make sure that you saw it and you're gonna put your your great-great-grandkids that you you you have that foundation and you're gonna keep on doing it. And yes, I want people to buy this book. I want in fact, after reading this, uh I'm gonna buy a copy, two copies. I've got two kids, and I'm gonna buy myself a copy of this book because man, you're in service, brother. You already you could have been like, you know what most people are that find success? I'm not gonna help out anybody. Nobody would. You could have Jake could be like, I don't know, screw it. They they want to find success, they want to reinvent themselves, go do it on their own. But you're you're passing wisdom, man. So people should look even at your social media. That's why I thought I thought there was a misprint. I thought you were like at least 10 years younger, because you're living your life. And yes, we all have to go to heaven one day, but when when the Grim Reaper does tap you on your shoulder, you'll he'll be like, come on, Jay, it's time. And you're like, no, man. I but go go get that guy that's watching Netflix that's streaming. He's streaming instead of working on his dreams. So hey Omar, I love you, brother.
SPEAKER_02Can I tell one more quick one?
SPEAKER_03You can tell anything, man. It's it's not like you're you're you're selling us a pipe dream. You're you're
A Growth Budget And Where To Find Jay
SPEAKER_03selling us reality, you're selling someone to work on their dream because it's never too late.
SPEAKER_02I'm giving the keynote speech for the California Association of Realtors in San Diego. I'm in a hall with 10,000 people, massive hall. Of course, I'm there to educate and inspire, but I'm also there, honestly, to sell books in the back of the room and to get people in training.
SPEAKER_03Capitalism.
SPEAKER_02So I'm I'm up there and I'm moving my hands and telling funny stories, and I'm having the time of my life. And I notice a guy in the front row that's at least 90 years of age, and another walker in front of him. And you know, when you're a public speaker, you pick out certain folks, people who are digging what you're saying to get energy from them, people that are kind of resisting arms crossed, saying this guy's so full of shit.
SPEAKER_03I can't believe I'm here. When's this guy gonna wrap up?
SPEAKER_02And you want to break and you want to break that guy down and get him into it. And I'm also watching the old timer, and I'm thinking, I wonder how he's responding. He must have listened to a hundred of these speeches. I'm wrapping up and I'm about to tell everyone the books and the programs are in the back of the room. I'm gonna run down this big aisle in the middle of the facility. I'm gonna be there to sign your program. I'm wrapping up and I'm closing the room. And as I'm doing that, the old timer stands up and he starts going down that middle aisle. And I'm thinking, wow, that's a funny time to leave. I wonder if I turned them on or turned them off. I don't know what's going on. I run to the back of the room to go sign the copies and talk to people. He's the first in line before we sell one unit. I am amazed. I go, Oh my god, my brother. I shake his hand, I give him a hug. I said, I'm so excited that you're buying this program. At this point in your life, how many years have you been in real estate? 45 years. I said, Well, you must know everything or a lot. He says, Kid, I loved what you said. Nothing was that different from anything I knew. I may have learned two or three really kind of neat new things. So thank you very much. But I'm back here buying your book, not for information, but I make a yearly $1,000 commitment for growth and development, and I haven't reached my budget yet, and that's why I'm buying your program. A budget for growth and development at 90 plus years of age.
SPEAKER_03Well, Jay, we're either growing or we're dying. We're there's no static, we're move moving, and he chooses to grow. So bless his heart, brother Jay. Thank you for the time, thank you for the opportunity. Two questions. How do we buy shift, the gift of reinvention? And the second question is how do we find you so we can follow up and we can ask, and we can just see you living your best life?
SPEAKER_02So, two things. Number one is in the document that I sent you called the Media Guide, undoubtedly you've got the Amazon link. So the book can be bought on Kindle for five bucks. Paperback is which I suggest, so you could take notes, $15 investment, and then that nobody in the world is going to buy a hard book except for me. And uh here's what I'm contemplating, and I'm hoping that I'm able to do it. It's only less than 30 days into the campaign. I have noticed that I don't know, Omar, did you notice that a lot of people only want to listen to books these days? Of course, of course, I recorded all 26 chapters, nine hours of audio tape, Coach J reading the book for everybody. So that if you buy any version of the book, you get the audios. And then you have in your media guide my brand new website, the Shift Academy, uh Shift Shift Program.academy. I'm sure you'll be able to put it in the notes.
SPEAKER_03Uh, for you, I'll do everything and anything, brother, because I love you. Okay, God bless you. This was wonderful. Invite me back. I got more. You have an open invite, brother. You you're we're kindred spirits. Whenever you want to come back on, my my show is your show, brother. Thank you for the opportunity. God bless. God bless you.