Jeff Ostroff, Looking Forward to Make Your Own Luck (#258)

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Jeff Ostroff is an entrepreneur, podcast host, voice actor, professional interviewer, lecturer, trainer, meeting facilitator, show guest, and author of “Successful Marketing to the 50+ Consumer.” As an entrepreneur, Jeff has started three businesses. Aside from his latest one, the Looking Forward podcast, his other businesses were Scenic Cycling and Ostroff Associates. The first catered to both the growing singles market and the fitness movement, while the second specialized in assisting organizations in identifying and profiting from trends and opportunities created by the massive over-50 population, including the baby boomers.

Jeff has been interviewed, quoted, or cited on more than 50 magazines, newspapers, and radio/TV stations, including The Wall Street Journal, The New York Times, Newsweek, CBS, USA Today, Business Week, The Philadelphia Inquirer, Inc., Ad Age, Adweek, and Modern Healthcare. He’s also given professional speeches to over 60 corporate and professional groups in the United States and abroad.

The Looking Forward Podcast

Jeff Ostroff hosts and produces the Looking Forward podcast, which he started in 2020, where he talks all about the society and market trends, how they affect you, and what opportunities they may present. Jeff has long been fascinated by trend analysis, which he developed after watching Louis Rukeyser and “Wall Street Week” in the mid-1970s. In 1988, he wrote an entire chapter in his book, “Successful Marketing to the 50+ Consumer,” discussing future trends and prospects for seniors and baby boomers in the twenty-first century. Many of his forecasts were correct, even though he had just a rudimentary understanding of the Internet’s arrival!

Traditional media keeps presenting us with terrible news that generates nothing more than anxiety. I cherry-pick the areas I want to stay informed on, such as advances in technology that can contribute to increasing the quality of our lives. Jeff feels the same about traditional news, and that’s why he focuses on something upbeat, inspiring, and hopeful with his podcast. This is in addition to informing and educating people about where things have been and are going, how it may affect them, and what possibilities it may present. His goal is to bring rays of optimism into a tumultuous and hard world.

And now here’s Jeff Ostroff.

Full transcript below

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Podcast with Jeff Ostroff. Looking Forward to Make Your Own Luck.


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Jeff Ostroff, Mike Malatesta

Mike Malatesta  00:05

Hey everybody. Welcome back to the How’d It Happen Podcast. I’m so happy to have you here. And I’ve got an exciting success story for you today, as I do every week. I’ve got Jeff Ostroff on the podcast. Jeff, Welcome to the How’d It Happen Oodcast.

Jeff Ostroff  00:24

Thank you very much, Mike. It’s a pleasure to be here. And I really appreciate your inviting me.

Mike Malatesta  00:29

So let me tell you a little bit about Jeff to get you excited. Jeff Ostroff is an entrepreneu, and author. His book is called, ”Successful Marketing to the 50+ Consumer.” He’s a podcast host, his podcast is called “Looking Forward,” and it’s a very interesting title. I like that a lot, Jeff, so congratulations on the title of that. Thank you. He’s a voice-over artists, my first voiceover artist that I know, the podcast. Jeff is also a professional speaker. And he says, I think he calls himself like a trend expert, but I’m gonna call him a futurist just because more people I think are familiar with that word. And we’ll see what how he wants to define himself. So I’m taking a little creative liberty there with my description. Jeff is also the luck instructor. And we’ll find out what that means to be a luck instructor. I’m fascinated to know, I deliberately did not look up on his website what a luck instructor was because I didn’t want to spoil the surprise. So here’s how Jeff connected with me on LinkedIn. It was really funny. He started sending me some notes after reconnect, and he says, I’m quite entertaining. And I have a lot I can speak about. If I do say so myself. Hey, I just did. So that gives you a flavor for his for his humor. And with that, let’s, let’s put this in drive and dig into Jeff Ostroff. So, Jeff, how did happen for you?

Jeff Ostroff  01:56

Well, I’m going to give you an answer that I don’t know anybody else has given. But you’ve had a ton of shows. So I haven’t listened to all of them. And probably there is somebody who’s answered it in a similar way, Mike, but the answer to that question is, it’s still happening. For me. It’s, it’s not a past tense, my career, if I want to focus on that, and certainly I’d be happy to talk about my life and your life. But my career has been a series of changes and evolutions and reinventing of myself. So back in the day, it happened to us your physiology, by my deciding that I wanted to work in a job that helped individual people as best as possible. And so I started working for the Social Security Administration, in the Medicare department in the Medicare area. At that time, Social Security was the big umbrella tent under neath, which was Medicare. And I found that to be very enjoyable. I had an entrepreneurial business on the side called scenic cycling, which Mike, if I ever had a chance to do it again, I probably would. But I found one time when I thought about going back and doing it again, the cost for liability insurance, which I didn’t really have when I did it was prohibitive for the amount of money I was making. So I have that little entrepreneurial thing on the side. And if we get to this, I realized in thinking further and I think everybody needs to think about this sometime if they’re reexamining their life, what was it that they did naturally when they were very young. And I realized that even when I was a kid, I was entrepreneurial, but didn’t think about it. So the point of that being that after about 10 or 11 years of doing that, and quite frankly, of the careers that I had in my first series of careers, that was probably the most satisfying working for Medicare, because I genuinely felt I had knowledge and a skill set to help people, different kinds of people, not just seniors, different kinds of people. But I had this entrepreneurial bent, you know, and it called to me, and because I was fortunate enough to have a wife who worked for DuPont, we didn’t have any kids yet. She said, Jeff, it’s okay. If you want to go out and strike the strike out on your own, which I did. I started my own business. And I thought that what I was going to do was continue to help people with my Medicare knowledge but focus on corporations who are dealing with retiree benefits, and hospitals who might need to know more about How the Medicare program worked and other health care organizations, and AARP, and so forth. And to make that long story short, I found out that none of those organizations really wanted to pay for it. That’s a pretty long story short. And so what I ended up evolving into was a quote unquote, expert on marketing to people over 50. Because I found out that’s what businesses would pay me for. I can’t say it was the thing I had the most passion for, again, the thing I think I have the most passion for, and you clearly do with your, you know, with a show in your book, which is a wonderful title and has great messages in it, owner shift. I wanted to help people. But I did this shift because you got to make a living, right? You got to make a living. And soon we would have twin girls. And so I haven’t had no courses ever, Mike in marketing, I became a marketing expert on marketing to seniors. And I felt really with the on-the-job knowledge I got, I became a true marketing expert in focusing on the 50 Plus market. And I have to laugh. I’ve been laughing about this mic for about 10 years now. And that is that I wrote a book called successful marketing to the 50 plus consumer, which you alluded to. And I wrote that book, Mike, when I was 38 years old. And I’m thinking what could a guy this is now what could a guy who’s 38 years old know about how to market to people over 50? But why did I know? And this is one of the,

Mike Malatesta  06:50

you knew enough to write a book, I knew enough to

Jeff Ostroff  06:53

write a book. And I had my own follow up strategies. And I interviewed people for the book. And they gave me strategies. And that was the book. So anyway, so that was a another How’d it happen kind of thing, I shifted into that. And I did that for about 11 years. And after that, I got tired of traveling. Because as I don’t know if you’ve ever experienced this, but many others have, you are not as much an expert in your own town as you are 50 miles or more away. And you might take 50 and make it 500 or 5000, because I literally spoke in Holland. And I was asked to speak in Australia. And yet, in Philadelphia, it was very hard to get paid jobs that I’m from Philadelphia, as you are, of course, we share that in common. So So anyway, I I ended up deciding that that was too much traveling, and I, we had twin daughters, and I just didn’t want to give up my family life to do all that. And that’s when I decided to go back and work for Uncle Sam again. And I went to work for the VA healthcare system, because my background had been in Medicare and I did a lot of work on my own as a consultant and speaker and market research guy and writer with healthcare companies. So that became another evolution of sorts. I went to work for the VA and healthcare, and communications and marketing, I headed up the marketing and communications effort for a network of 10 VA hospitals. I eventually retired. And, again, having that itch, I couldn’t retire for very long. And after a few years, I I started to do something Mike and I’ll I’ll end this because we I’m sure you’re going to want to follow this up with your own thoughts. But I started to do something, Mike, which is something that not everybody is fortunate enough to do. But boy, if you can do it, it’s the greatest thing in the world. And that is I started to pursue the things that he would have done earlier in my life. Even if I made nothing doing them. In other words, the things that I truly loved. And I’ll point to two specific things. I always from the time I was a kid Mike, I loved to announce things. In fact, as a 12 year old, the class prophecy for me was I was going to be a sportscaster. That didn’t happen. But I always loved to announce things. It was just something I did very naturally and we could talk about that if we need to. And the other thing that I just naturally love to do I have a great curiosity about people as you do reshare that I love to converse with people either in an informal way, or a little bit more formally, in terms of a podcast type of a product. And so the announcing became the voiceover stuff. The interviewing became, I do some professional interviewing work for clients. But I also do the podcast, conversing as you also called or interviewing. So that’s the long story short, so how did it happen? It’s still happening. I have ideas. I guess that I’m kind of shocked. Mike, I, I could retire easily as I know, as I know, you could. And yet there are other things that keep calling to me. And exciting me.

Mike Malatesta  10:47

Yeah. Well, I’m glad that you, you know, it’s continuing to happen. I have had people answer the question. Similarly before, and I never expect anyone to sort of answer the question as well. This is how it happened. And here’s a period on the end of that. And that’s, that’s the end. You know, that’s it. But I wanted to ask a few questions to follow up on what you gave us there. Jeff. The first one is when you did retire, did you feel like you had to retire? Like that was just a normal thing? Or was there some type of, you know, event or something going on in your life where you were like, I just had it, you know, sort of thing, you know, because so many You don’t sound like this kind of person. But so many people sort of slog their way, through an existence of work existence that they don’t, they don’t like they don’t get a lot of energy from but, you know, they feel like they’re, you know, stuck there. And, and I could be a very legitimate feeling, but, but you don’t sound like that kind of person. So I thought, Well, I’m gonna I just want to explore that a little bit.

Jeff Ostroff  11:55

Don’t be fooled Mike. In terms of what I sound like. The fact of the matter is, the last position that I held with the VA Health Care System, was the only position in my career that I did not choose everything else that I did in my career, I chose it, I either created it, or I got hired for it, because I found out about it before just about anybody else did. And I was the right fit. The last job, we had a change in leadership at the top of the organization, and I was reassigned to work for a hospital, as opposed to the network of hospitals. It was not the job that I wanted. It was later in my career, I did a good job doing it. I didn’t care for it. I didn’t feel comfortable in it, I started to feel very stressed in it. And I decided that I would take a slight cut in my pension, I’m lucky enough to get a pension. After 23 years I had in federal service. And I left that job. And I never looked back. My only regret, or my only concern in making the decision was if I hang on a little bit longer, I’ll have a cleaner exit. And maybe I’ll make a few more dollars. You know what I mean? Okay, so no, I was very unhappy in my last job. And that was, in fact, the reason why I retired, then I would have otherwise hung on for about four more years. So thank you for asking the question. It’s a very valid question. And I know I share those feelings with a lot of other people, including some with whom you’ve spoken.

Mike Malatesta  13:42

Right. And that, that thank you for that the want to get back to this starting the agency for marketing agency for 50 Plus, consumers when you were you wrote said you read the book when you’re 30 at 30 a business around that same time or a little bit before

Jeff Ostroff  13:59

I started the business in 1980. I left the Medicare program went out on my own in 1984, September of 1984. The book was written 88 into 89. Okay, came out in 89.

Mike Malatesta  14:13

I, there’s something powerful, I think out there for people in what you said. So you said I’m paraphrasing, but you said one, you know, he had had he hadn’t had to make a living. And what I was trying to do before I was you know maybe getting the thing I was passionate about I was getting interested but no, I couldn’t find a fit with a customer. paying customer that is so you so you decided to take on this new thing. I think what was really interesting about it, and I want to hear your perspective on it, because a lot of a lot of I actually mentioned this in the introduction. I think my book is that there’s so many people out there that are telling us, all of us that you know you really You have to figure out your why and, and follow your passion. And you flat out said I wasn’t passionate about what I was doing. So do you believe in when it comes to like entrepreneurism, at least let’s say you’re moving the needle, you know, financially or, or recognize, you know, recognizing success, I guess. Are you believer? Well, where do you come down on that, Jeff? versus, you know, kind of what the reality of your situation?

Jeff Ostroff  15:39

Well, I think that there are two extremes. And if you’re lucky, you can heart you can harmonize them. So the one extreme is a person who does something, we’re just talking career now for a living, because they have to make a living, they have no love for what they do. It doesn’t excite them, they don’t jump out of bed in the morning. On the other side of the equation, you have somebody who has a tremendous passion for something, let’s say an artist of any kind, were artists in a way, artist of any kind, and they can’t make a nickel doing it. Okay? You have two extremes there. It’s great that that the one is making money, but he or she is not happy, the other person is very happy. But they’ve got to make a living. The optimum situation, which very few people find, by the way, is where you’re actually doing something. And making a living that satisfies you doesn’t, you know, what satisfies me and what satisfies you and somebody else needs or they’re all different. But if you can make a living, doing something that also gives you joy and gratification, and you’re excited about doing, you’ve got it all. And we often hear about the rare few, at least, they’re rarely spoken about. And they’re often in the entertainment world, for example. So like George Burns, I used to talk about him when I gave presentations. He loved what he did. And of course, he lived almost 100 years of age. And and so you hear about people who will say, you know, I love what I’m doing, I’m never going to retire. A very good well, a man who became a good friend of mine, but I short I unfortunately only knew him six months was a guy named Jack Kilian, you may have heard about Jack. I don’t know if he was on your show. But he wrote a book called networking all the time. And Jack just passed away, sadly, in October at the age of 84, I think he was a very, very, very successful entrepreneur. His passion was in networking, he just got joy, he would get up every day excited about networking. And it helped him in his career, too. So I think that those people, and I do think they’re in the minority, who can marry those two things, making a living that satisfies them, and having it be something in which they have a passion about a joy for? You got it all, if you can do that. Yeah.

Mike Malatesta  18:31

I think yeah, I think you’re right. If you can do it, you definitely. But harmonizing that is a lot less sexy than talking about it, like actually harmonizing it, because it seems to me like even if you get started on something you’re passionate about in a business, for example, you know, the grind of the business and the reality of being in business was, you know, if you’re not very careful, and you’re not surrounded by the right people, and you’re not forward thinking enough, it starts to erode the passion because the thing you’re passionate about, you’re doing less of I hear you, I think that happens to to a lot of people.

Jeff Ostroff  19:16

I hear you and I’d like to jump on that by by saying something else, which I hope that your listeners will find somewhat enlightening, or at least interesting. Years ago, I went to a presentation given by a person I think, is so talented, very bright guy and I worked with him closely on many projects, and he wrote the foreword to my book, Ken dike, Wald, who heads up a wave, and I’ll never forget, Ken was giving this presentation in front of a large audience, and he’s one of the best presenters I ever heard. Somebody once gave me a compliment. came up to me, they said, you sound like Ken DayQuil? And I said, No, I don’t. Can I call this? You know, he’s in another league. But Ken asked everybody this great question. He said, How many of you think the best years of your life were between the ages of zero and 10? And he went on and on 10 to 20? You know, you might want an on over 60? Well, the overwhelming majority of the people in the audience were nowhere near 60. I was certainly nowhere near 60. And nobody raised their hand, you know, thinking ahead that over 60 would be the best years of their life? Nobody, I certainly didn’t, I was dreading it. But I’m going to tell your listeners that I have found so far the years over 60 to be the most exciting, rewarding, and wonderful years of my life. Now, it’s not going to be true for everybody. And many people don’t make it sadly, to that point. But why is it that way, because I can pursue things that I truly love, without having to worry about, you know, what I got rejected for the 5,000th time, it’s okay, I have enough money that I’m going to be alright. And besides which I’ve been rejected 30,000 times, it doesn’t bother me to be rejected one more time, as long as I’m being me, and doing what I want to do. And very few people will have that freedom to pursue what they truly want without having to worry about whether or not it’s financially successful, until they get to that point, if they’re able to even at that point. So I understand what you’re saying. When I was younger, it did wear me out greatly. That’s probably in part why went back to working for the federal government and VA is it was very hard, my livelihood, being on my own was kind of up and down and up and down, and up and down. Plus a lot of traveling. And if I really wanted to make the money, I’d have to do more traveling. And you have to think about is this really what you want to do, you’re only going to have your children once, I also wanted to be a good husband. And so I just wanted to share that with people. Because it may be that you have quite a few listeners who are over 60. At the same time, you may have many, many listeners who are under 60. And I would like them to not be afraid of getting older. Because if you take care of yourself, and that’s really important. If you take care of yourself physically and mentally. Life after 60 can be very exciting.

Mike Malatesta  22:59

And that 60 that I as you were saying that I was thinking myself first I thought well, of course every you know, every next 10 years is going to be as good as you make it right. So of course, there’s there’s no there’s no age where you expire until you die. There’s no you expire. But, but I can also see what you’re saying, too, because if you it’s really about how you do you think do you do you think you have a future?

Jeff Ostroff  23:28

Absolutely. In fact, that’s part of why I have looking forward is because it’s forward thinking it’s upbeat, looking forward. And looking forward. I’m looking into the future, and I wouldn’t be looking into the future. If I didn’t think I had one of my own. Now how long my future is. That’s finite? I just don’t know. But I definitely know. And think that for now. There’s a future.

Mike Malatesta  23:53

Yeah. And the finite, the finite, finite pneus of it, Jeff, really doesn’t matter. Because nobody knows when when that is and so tomorrow’s the next day. And so looking forward always works until

Jeff Ostroff  24:08

well, you have to you have to do that. And I will add that this comment to that mic. And that is I know, some people some very close to me, who are spending too much time looking backwards. Yeah. And that is a prescription for disaster. Yeah, disaster.

Mike Malatesta  24:30

Yeah, I call that I call that winding down thinking so if if, if you’re around people who are winding down, you’re, you’re gonna wind down. If you’re around people who are winding up, you’re probably gonna wind up, right because who you surround yourself with and intentionally makes a difference.

Jeff Ostroff  24:52

It really does makes a difference. It really does. Jeff, is it

Mike Malatesta  24:57

is it inappropriate for me to ask you whether You know that the, the grind and the travel that you talked about with your business had had an impact on your family? Like,

Jeff Ostroff  25:11

I don’t think that had a big impact on my family. Okay. And the reason is, I know this is a cliche, but I, I really believe this, I think if you had a chance to talk to, I will admit, she’s my ex wife, but we’re very close, after 28 years of marriage, we remain very close. And if you talk to my twin girls, they’ll tell you this, I could never allow myself to get too invested in my career, I met some people along the way who had done that they suffered for it, I had many opportunities to relocate, I never wanted to do it, I wanted to not only be near my nuclear family, but my parents and my, my ex wife’s family, I’m also still close with them. And I had several, several entrepreneurial ventures, that if I had moved them a little further along, like that could have either been investing money in them, or traveling more to make them happen. Any one of these could have happened. And they range from a mutual fund, to a tournament, to a retail store concept to a concept at a gasoline station. The latter of which is actually being done now. But not by me. But each one of those I was stopped, there was something that stopped me. And what stopped me was a, I’m not a huge risk taker, and be I realized the price that I would pay for the success that I might achieve in doing that. In fact, one person, very successful said to me, you’re more afraid of success than you are a failure. And it’s and it was true. So no, I don’t I don’t think that was a problem. It was a problem in my businesses becoming successful. But it wasn’t a problem in terms of my family situation.

Mike Malatesta  27:18

And so that’s very interesting, more afraid of success is that because you equated success with real being requiring your family life to suffer?

Jeff Ostroff  27:35

Yes, that that that is a function, which I still have to keep in check, quite candidly, even though I don’t, I don’t really need to be, you know, a multimillionaire in a business. Because I feel as though there’s always this risk of getting too caught up in the work that you’re doing to make money. And that doesn’t necessarily even mean a job. It could even mean maybe your your I know somebody who was really involved in investing, and ended up not being very successful investing and then didn’t know what to do with the rest of their life and became severely depressed. And as far as I know, still his person moved away. Couldn’t that was the one thing in their life was. So it’s a question of I, I try to have balance don’t always succeed. But I’m always sort of subconsciously mindful of the fact that if I get too caught up in this work stuff, where this passion that I have for something outside of family, and friendships, that it’s going to draw me in. And that can be a very dangerous thing, because I might lose some other things, by the inequality of the time that I’m spending with one versus the other.

Mike Malatesta  28:56

Okay. You said something that struck me, Jeff. And I want to dig into it a little bit more before we we shift into you know, what you’re working on now. Sure intrigues me a lot. And that was this, you know, I’m way more known 50 miles from where I am than I am, where where I am. And I don’t know if it’s a direct parallel, but it got me thinking since you’ve said that like about really how many people you’re impacting with your work and I think about entrepreneurs, myself. Executives, you know, people who in their world are exceptionally they’re there. They’re held in high regard. They’re well known people listen to them. They have a certain expectation about their environment, and it seems like that would transfer no matter where they go, for example, and I think that it doesn’t, except for a very, very small percentage of people, it doesn’t transfer that well, like, for example, when you retire for, you may continue to be well known inside of the company, but you’re gone from there and outside. Nobody knows who you are. And nobody gives you the deference that you were used to getting. Or when you sell your business, all of a sudden, you’re just a, you know, you’re just a normal person, then you don’t have this sort of support network. And, and when you said what you said, I thought to myself, Okay, yeah, so Jeff’s, you know, going all over the country, maybe all over the world being known for this certain thing he’s doing, but, you know, around where he lives, he’s just Jeff. And so it’s sort of the reverse of what happens to a lot of people do well, and now you spent part of your, your, your year in, in Florida. Yes, that’s what a lot of people do. And I’m sure you’re around a lot of people who aren’t shifting who aren’t. But but were very, let’s call it successful. But now they’re, they’re there. It’s like, that’s all gone, because they haven’t continued to work on looking forward. For example, do you see? Yeah, you believe that?

Jeff Ostroff  31:33

Well, yeah, I’m going to give you an example of something that you reminded me of Mike, that I used to talk about in my presentations way back in the day about marketing to people over 50. But it can pertain to, to younger people, too. If you if you think about it. There was a guy back in the day when I was doing this stuff. So this is probably in the late 80s, early 90s. His name was Albert Myers. And I think he’s passed. But he wrote a book called success after 60. And he said that most people who aren’t adequately prepared for life after the retirement will die soon thereafter. And a great example. Either he gave that or I thought about that was Paul Bear Bryant, who was the coach of the Alabama Crimson Tide, that his whole life was wrapped around the Alabama Crimson Tide. And when he retired, he lived about six months. And I guess you could say Joe Paterno from Penn State, if you’re into sports, kind of the same thing, although he had a more ignominious kind of a, you know, an ending with his cancer, and what happened with the scandal there. But the point is that we have to be careful, I think about making too much of our identities wrapped around one particular thing. Because you’re right, the identity can go in a heartbeat. And, again, it’s one of the reasons why I think that trying to achieve some level of balance, diversity, focus, when you need to focus is so important in your life. And I say try, because it’s an ongoing challenge for a guy like me, I think I do have some add, although it was never diagnosed. So yeah, I think I think what you said is absolutely correct, that we could find that we could very easily find ourselves lost. If we get too caught up in one identity, one thing, and then for whatever reason,

Mike Malatesta  33:47

we lose it. Yeah. I mean, I know that that definitely happened for me, when I 2015, I sold my first business I and I’ll just use LinkedIn for as an example, which is every connected so at that time, I think I had 200 and some connections, because I would not accept any connections from people because I wouldn’t even look at LinkedIn, but I wouldn’t, I would rarely except connections because I thought, why do I need to connect with this person? I’m, you know, I got my thing. Why do I need to connect with this person? And, and after I sold the business, it started to and started doing the podcast, it started to occur to me that you know, nobody knows who I am. I certainly am not going to walk into someplace and people are going to have this expectation or I’m going to have this expectation that I deserve something from these people. So even though I had you know, 20 years of being you know, impacting a lot of people in a positive way, I hope from clients and customers to you know, team members, and and in a whole You know, everybody else that was around me, that was over. I mean, right? That was just a memory that was a, that was a looking back in the day sort of thing. And going forward, I thought to myself, well, if I don’t find more people to interact with, you know, time is going to erode this, whatever, whatever goodwill, I’ve, I’ve an success I’ve had, and I’m just going to be looking in the mirror all the time, instead of, you know, out the window looking forward. So I, so I started, you know, connecting with people. And for at first, I thought it was weird to connect with someone I didn’t know. But then it seemed like an opportunity to connect with someone that I didn’t know, because I don’t know what they know. They don’t know what I know. But if we connect, we start to have like a little community, and maybe we start learning from one another, and maybe we start referring one another, and maybe we start having ideas for one another and whatever, which. So that’s, that’s my own personal experience with with that, you know, I was definitely on the wrong side, I think on the wrong side of that. And, and I think a lot of people are they think they have everything they need where they are, and they never think about what it’s going to be like when that ends, I

Jeff Ostroff  36:15

can give you a couple of reactions to that. Yeah. The first one is in a similar vein, like, I wasn’t using LinkedIn at all, because I never really needed to use it. In my last career, my middle career, where I was on my own, it didn’t even exist. And then when I finished up at VA, I didn’t really need it at VA, I was going to hang in there and, you know, retire. So it wasn’t until not not even two years ago that I started taking LinkedIn seriously, conceptually, I always thought it was a wonderful idea. I love connecting with people. And I had next to no, I think I had 50 connections. So but I came at it from a different perspective, I was loving the idea of connecting with people. But like you, I realized at the same time, nobody knows what I did in my career. But here’s the other point, I want to make that that you brought out in me. And that is in the way that you kind of have that Mike Malatesta has a blank slate for people who don’t know who you are. And you’re very successful. I mean, I’ve it’s amazing to to waste management companies, and you sold them and you’re a trillionaire. Now, I mean, that’s amazing, richer than Jeff Bezos, it’s just an amazing thing. But still, if somebody says you’re not a celebrity, which is fine and dandy, that has problems associated with it, then you walk into a room and a lot of people would know you if you whether you’re in Milwaukee or not in Milwaukee. But that’s kind of the way it is in general. In other words, it’s kind of a haunting thought. But I remember when I used to do more professional presentations, and the person would introduce me, as you did with a kind introduction. And I would, I would realize that you know what this audience has never heard me before. Doesn’t matter how great, the emcee says that I am. I’m a zero. I’m a zero. I mean, I’m a zero with maybe, maybe I got one green light on for them. But nothing is going to matter until I deliver until they hear what I have to say. Then I become somebody. In the same way that when you’re just introduced to somebody or you meet somebody write your zero if they don’t know you. And I know they talk about first impressions. It’s kind of like saying, first impressions. There are just what 7 billion people in the world and let’s face it, in almost every case. Most people don’t know who you are. I mean, there’s there is exceptions. There are exceptions, of course, but just about everybody is somebody that most people in the world don’t know. So most of the time, you’re engaging people with a blank canvas. And you have to perform. And I don’t mean that in a phony way you you got to you’re on and you have to be your best self in a genuine way. You know, don’t be a phony, but you got to be your best self. So yeah, I echo what you said about LinkedIn. And and I just wanted to throw that additional solid in valgus first impressions What?

Mike Malatesta  40:01

What is a lock? Instructor Jeff?

Jeff Ostroff  40:04

Okay. Well, a look instructor is something that I basically created. I don’t know, I don’t know if there are any others besides me. And I’ll give you I tried to be me, I think I am very genuine, I don’t I don’t put on airs. And I just hate to do that. So I think humility is very important. So let me tell you about that. I have given a six hour program to three different audiences on how to be luckier in your life. It’s called being lucky, it’s no accident. I did that at the University of Delaware for students there. It was very successful. People really liked it. I enjoyed it. And I thought that maybe I would decide this is a few years ago, in the last six years or so I don’t think I’ve done it in four years, five years. But I did it in person. And personnel, we do some of the things virtual but I did in person it was I thought it was great. And it was based on research I did into who, who gets luckier? Or who are the lucky people who are the unlucky people. And there’s certain principles around that. The problem that I have with that, Mike, is I’ll go back to something earlier, which you may want to comment on. I have many, many ideas. I think I have a number of skill sets. I know where I’m not skillful. Try to stay away from that. But I think I know where my skill sets lie. And I thought that maybe I would pursue aggressively this luck instructor program, this luck program with me as the instructor because I feel I’m very qualified to do it. It was very interactive, and so forth. Focus is so important. And I just had to reel it in, it’s there. If somebody would contact me and say, hey, we’d love for you to do a presentation for our group on how to be luckier, I can pick it up and do it. But I don’t have time. Time Being that you’re replaceable commodity. I don’t have time now to say I’m going to promote luck instructor because again, people don’t know about it, right? I can’t, oh, we’re gonna call Jeff about doing they don’t know, you know, who knows right? Few people. But uh, so I got to focus on what I’m into now and what I really enjoy the most, which is voiceovers, podcast, hosting, and interviewing people outside of podcasting, just doing business to business or I haven’t done any business to consumer, I’m sure I could do that interviews, I would love to do the the program again. And just to say one more thing about the program. It was actually Mike four successive weeks, one and a half hours per week. So we met four times for an hour and a half equaling six hours, it wasn’t just standing up there for six hours doing the program. But it is very important, whether somebody take a class like that or not. And again, I don’t know if anybody’s doing it. I would love to do it. But it is very important regardless, for people to learn more about, thus, the certain behaviors and attitudes and skills that are necessary to improve the quote unquote, luck in your life. And as I pointed out in the program, it’s not about serendipitous luck. It’s not about the guy who in one book was written as having twice missed terrorist attacks because it just happened. He wasn’t there and he was supposed to be. The guy was supposed to be on the plane that flew over Lockerbie, Scotland. He was also supposed to be when 911 happened. And he just happened for circumstantial reasons. He just wasn’t there on that plane. He wasn’t in the building at that time, but he was supposed to be. That’s not the kind of luck I’m talking about. This is the kind of luck that you can play a much more proactive role in and we could certainly talk about that more. If you you’d like to so the honest answer is I don’t I, I don’t know of anybody else who’s doing it. I actually did reach out to two people to see if they might want to partner with me in doing it. And one never responded, and the other person doesn’t seem to have the time. And I decided, unless there’s an interest shown, maybe, maybe it’s for 2024. But right now, I gotta focus. And it’s very hard to focus, but it’s very important to focus. So one,

Mike Malatesta  45:33

one follow up question. I don’t know if it’s, if I’m attributing this quote, directly, correctly, to Edison or not, but someone is, I think it might have been him said that, you know, luck is, you know, luck is, you know, wears a uniform and, you know, works hard or something like that. And I, you know, you’re basically saying, hey, the reason people get what other people call Lucky is because they actually do things, they actually, they’re not hoping that something happens, they’re taking a step towards making it happen. Yes. So So I want to ask you, just briefly here, do you believe in luck, first of all, and as the luck instructor, you know, as you take people through that course, when you were what, you know, what are the top say, two, three things that you’re telling people work, you know, to enhance their luck,

Jeff Ostroff  46:25

okay. There are situations, and I spoke about serendipitous ones, where luck can play a role in your life. And it’s purely accidental. There are other situations, which I think represent the predominant scenario, where you have as Seneca said, you’ve you’ve been at the point where preparation meets opportunity. That’s what luck is. So luck, is about preparation for the opportunity that may come about. And I think it was Thomas Jefferson, but don’t quote me on this. It’s been a while. But I think he said that, the harder I work, the luckier I get. Luck, kind of, in some ways gets a bad rap. Because it sounds like it’s just this thing that happened out of thin air. That’s not the kind of luck I’m talking about. So let me give you a few examples. i There are actually 12 principles, four major principles and three sub principles that I that I speak about. And I may even add more now that I’m getting more experience in life. But one of the things is, it’s a way it’s being aware of what’s going on, around you. Now, that could be literally what’s going on around you and you know, 10 510 feet away from you, Mike, or it could be what’s happening in the world around you. But I’m gonna I’ll give you a specific example, from a book called The luck factor, which is an excellent book. And there are actually two books written in different timeframes with that same title. So if you look up the luck factor, there’s two books through different people, both good books, one predated the other one. But the example I’m giving you came from the second book. And the example is the I can’t remember now his first name. I’m just going to call him Mr. Hell’s burger. Mr. Helzberg. I don’t know if you may remember him from your Philadelphia days. I’m not sure if he was in Milwaukee. He owned a chain of jewelry stores. And in fact, I think they still may exist. I’m not positive. I haven’t been in the jewelry store in a while. But Mr. Helzberg was it might be Bernard, but don’t don’t go by Mr. Helzberg was about 60 years old. And he wanted to sell his business. And he was as the story goes, and I it’s not a made up story. He was walking, I believe in New New York might have been to know Hatton amant, Manhattan, New York, and just in front of him, happened to be Warren Buffett. And Warren Buffett was talking to somebody and the other person addressed him as either Mr. Buffett or Warren Buffett. He always he always said Mr. Buffett, I’m guessing how Ellsberg heard that. And any had and this may be another attribute. In fact, I would say of luck is first of all, he heard it. He heard those words being said or that word Buffett. Mr. Buffett, okay. And he had the gumption In the courage to go up to Mr. Buffett and say, Excuse me, Mr. Buffett, I overheard your name or something to this effect. I actually have a business that I’m looking to sell that I think you might be interested in. Long story short, Buffett ended up buying hells Berg’s business. And I’m sure he paid a good amount of money for the business. And I don’t know all the details after that. A lot of people, a lot of people, Mike, and we could generalize this, so many ways, are so caught up in themselves in what’s going on inside of them in their own thinking, they miss things that are happening right around them. And again, this could be micro like within 10 feet of you, or it could be macro things, trends, things that are happening in the world. So that’s one a second example or accepts the second strategy. Excuse me. Can you cut that out?

Mike Malatesta  51:13

Cut that out? Yeah,

Jeff Ostroff  51:14

I thought I had that. Oh, good.

Mike Malatesta  51:16

Let’s just stop. Let’s just stop for a second count. 321, you start again? Okay. Sure.

Jeff Ostroff  51:22

321. Another strategy is what we talked about with linked in, you have to build according to the experts, which includes the authors of both of those books, the luck factor, and some others that have written about this, you have to build a network of connections. This is what LinkedIn is helping to do a network of connections. So that if in fact, you are looking for something, you can reach out to people who are within your network, and let them know what you’re looking for. That’s one thing. The second thing is, again, if you the wider your network is, the more aware you become of what’s out there, and what opportunities are out there. How many times have you heard about somebody who said, you know, I just found out that Mike Malatesta left his job at, you know, XYZ company, he was he was like the head of marketing. And here you are, you’re looking for a VP job in marketing at the kind of company where Mike worked, you have so you need this, this network of connections is another very important tip. And again, there are many others. One more, though, that I will share for now is this one, and this is critically important. And I can give you an example about this in my own life. And this also relates to something Mike that I’ve been studying for the last couple of years, which is the philosophy of stoicism, which is a very practical philosophy. But I I really implemented this just because I kind of had to was way before stoicism when I turned 41 Not much to my surprise, quite honestly, I was told I had type two diabetes, type two diabetes. And I was a gigantic consumer of pasta, of bread, pizza of all things carbohydrate, except for maybe I didn’t. I didn’t binge out on apple pie, and candy. But all that other stuff. I married an Italian woman. Her mother and grandmother were great Italian cooks. I love the Italian food. So I ate in 41 years, I probably ate 200 years worth of carbohydrates. Okay,

Mike Malatesta  54:23

so I hear you I was there, man. I was there.

Jeff Ostroff  54:27

And I’m saying people can’t see me but I’m, yeah, I’ve always been relatively thin, except when I was in my early 20s. I was much more muscular. I was working out much more and could eat more. But anyway, it took me a little bit of time. I will say I was never depressed when I found out because I wasn’t shocked. There were some earlier indications. Plus my mother had diabetes, and so did her mother, but they came later for them. It came later for that. So anyway, The point I want to make is, I decided to make it a challenge for me. The challenge being that as long as I can do it, I do not want to go on insulin. Now, I’m not saying that to be on insulin is a death sentence that it’s a terrible thing. Many people will live many years on insulin, and God bless them. I just know it introduces an additional complication into your life that I was hoping I wouldn’t have to deal with. And I was told by more than one person, including my endocrinologist at one point, that after about 10 years, almost everybody ends up going on insulin. That’s the path when you have type two diabetes. But I decided, and I don’t want to make myself have to be unique here or a superstar, but I am in the minority, I decided, You know what, I’m going to do whatever I can to not go on insulin. And it’s getting close to 30 years later. And I just take the one drug, that first drug that everybody takes, which is meant for him. So the point of that is, you need to try, it’s not always easy. But we all are in a position where we’re going to have to do this once or twice or 100 times in our life. And you have because I’ve read about your life you have you have to take adversity, you have to take something that happens to you that you didn’t want to happen, some letdown, some misfortune, some rejection. And you have to find a way to turn it into a positive into something good into a lesson learned. So you have to take negativity, or negative experience and turn it into a positivity, a positive experience. And that is what the luckier people tend to do. And that’s what the on lucky people, conversely, tend not to do. They say, Oh, I failed again. Nobody likes it. Nobody wants me. They’re all or some people might say, Mike’s a rotten guy for not accepting me to be a guest on this podcast, he’s a loser. So they’ll turn it out when somebody else. One of the things that you do, that I really appreciated is you realized, as you evolved, that personal responsibility is critical. We we we have to take responsibility only for ourselves, we can’t be responsible for anybody else. That’s part of what stoicism teaches you the dichotomy of control, we can control our thoughts or feelings or behaviors or attitudes, but things outside of us are beyond our control. And that, as it happens, I learned before I learned the the luck principle that relates to that before sell us ism, but they of course, milled. And there are a lot of truisms out there that are like that. And they’re, they sound hackneyed and trite, but that’s because they’re, they’re real.

Mike Malatesta  58:19

So besides, I’m just curious on the diabetes things here. Besides in that form, you just adjusted your diet primarily. And that’s what

Jeff Ostroff  58:27

exercise exercise, diet and meditation are, are there and sleep. Now sleep is a challenge. But I try to get at least seven hours. When I failed that, and I don’t have any problem talking about failures, I’ve had millions of those to what I failed at is I’m still having a hard time getting to bed around the same time. Or maybe more importantly, they say getting up. At the same time. I will say that’s still a work in progress. But life is a work in progress. Mike, one thing I used to say, and then I’ll turn it back to you. It reminded me of something in my talk I used to give about people over 50 I used to say people over 50 don’t want so much to grow older, they want to grow older, with the emphasis being on growing not on the word older. So we all grow older, right? We’re all going to grow older, if we’re lucky, we’re gonna grow older, but the emphasis should be on the word growing not on the the older. That’s my belief

Mike Malatesta  59:34

right now. I think that’s a healthy way to do it. I mean, it’s just like looking forward. It’s the same thing, right? It is. So Jeff, as we finished up here, I want to put a little challenge out to you if you don’t mind. So I want to I would like to meld your voiceover particularly your British or southern accent voiceover with your with a description of your podcast for people and how they can find it and listen to it.

Jeff Ostroff  59:59

Sure Well, I have a website, www dot Jeff dash You will also find me on LinkedIn. And here’s an important thing, Mike and I don’t know if your name if you’ve run into this, you wouldn’t think my name would be that common. You know my last name, you wouldn’t think it’s that common. My first name by itself is not uncommon. I, on at least a half a dozen occasions, have gotten emails to my website from people who are talking about another Jeff Ostrom. He’s in Florida and he has YouTube so people if you’re going to contact me, I’m the Jeff Ostroff that does podcasting does voiceovers wrote the book successful getting to the 50 plus consumer has a page about the luck instructor. I’m not the other Jeff Ostroff. So I have a presence, a prominent presence on LinkedIn. And I’m always interested, also Mike and I posted this today on LinkedIn today happens to be a Tuesday. I’m always looking to help somebody who might need a new job, a new career or a connection. If I can I make no promises. I don’t, you know, I don’t know 50 million people. I’m not Bill Gates. And I’m not Warren Buffett. But if I can, I try to help people because as I recently read, and this won’t surprise you, Mike, a study I just read this in the last few days. A few studies now are showing that when you help somebody else, when you do something to make somebody else happy. You get more happiness personally out of that than if you do something for yourself to make you happy. Going back to your concept of being selfish, yes, in a way, my helping other people is in a way selfish? Because it will do me good. I like it. And just if I could say one last thing, again, briefly, the podcast, looking forward is about trends, opportunities, and the future, and how you might capitalize on those. And we’re speaking in a more global sense. My guests are not just in the US. They’ve been from Canada from Europe. And I’m always looking for new guests. And I’m even interested if anybody is interested in this, not only in taking on some more voiceover projects. But I’d like to co host or host another podcast, I do get a lot of joy and pleasure out of that. Because again, it all goes back to thinking about what you like to do. And did naturally when you were younger that you took for granted. And other people didn’t other kids didn’t because for them, it wasn’t so natural. Jeff, you’re always announcing things. Jeff, you’re Why do you keep putting this microphone in front of me, right? Because that’s what I like to do. And they did it for them. It wasn’t so natural. And I didn’t think it was such a big deal. So don’t discount people, the things that you like to do when you were younger, and you did them naturally. And you may have been very good at them. Because that’s a huge clue into something that you may want to pursue vocationally, or maybe even vocational.

Mike Malatesta  1:03:44

That’s a great thing to leave everyone with Jeff, thank you so much for being on the show today. I really have appreciated getting to know you. And thank you for sharing your wisdom and your UPS, your downs, your movements, your shifts, and most of all, this whole way of re that you’ve like caught reinventing yourself after you quote unquote retired. Boy, there’s a lot of power in what you shared and what you’re doing there for for all of us. And I love the work you’re doing. I’m looking forward. And yeah, keep it up.

Jeff Ostroff  1:04:18

Thank you very, very much Mike. And, and at the same time, I also want to commend you for what you’re doing to help people to inspire people to motivate people, not only with a spoken word, but now with the written word with your with your book, and I do love that title. I do love that title. I like I love the plan words, owner shift as opposed to owner shift ownership. So you got me saying ownership all the time. I’m never gonna say ownership again, Mike, but but I’d love it. I think it’s great. It’s a mind shift. And that’s very Very important.

Mike Malatesta  1:05:00

I’m starting to shift movement. I’m the shift instructor,

Jeff Ostroff  1:05:06

your shift instructor and congratulations really on all your success and about the word that we didn’t use that’s become so popular nowadays. We talk about evolution, you pivoted pivoting, right? We have to be able to pivot, and you pivot it. You had some tough things going on. You had this great career and you had to make a pivot. And you did it. And you’ve done it very successfully. So kudos to you.

Mike Malatesta  1:05:34

Well, hopefully I’m doing what I was naturally born to do, Jeff,

Jeff Ostroff  1:05:39

I think you are. Alright.

Mike Malatesta  1:05:41

Thank you so much. All right. Thank

Jeff Ostroff  1:05:42

you. Take care now.

Mike Malatesta  1:05:47

321 Hey, everybody, just a heads up on this episode. I’ve got Jeff Ostroff on the podcast. And Jeff is not the normal sort of person that I have on the podcast. He’s in his early 70s. And he’s had a really interesting mix of careers between you know, working for companies working for the government, and being an entrepreneur. But what’s most interesting about his story is what he’s done after he quote unquote, retired the way he shifted his his efforts the way he really focused on looking forward and most of all the way that he got back to doing things that he was the way he says it is what I was naturally good at when I was a young kid. So I think there’s a lot of value in this in this episode, and we talked about luck and we talked about you know, staying connected, staying networked and, and a bunch of other stuff. I think you’ll like it and enjoy

Mike Malatesta

Mike Malatesta

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