282 David Stillman

Jeffrey Feldberg: [00:00:00] Welcome to the Deep Wealth Podcast where you learn how to extract your business and personal Deep Wealth. 

I'm your host Jeffrey Feldberg. 

This podcast is brought to you by Deep Wealth and the 90-day Deep Wealth Experience. 

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David Stillman is the co author of best selling books, When Generations Collide, and The M Factor: How the Millennials Are Rocking the Workplace. He has contributed to Time, The Washington Post, The New York Times, and USA Today, and has been featured as a generational expert on CNN, CNBC, and The Today Show.

Welcome to the Deep Wealth Podcast. You heard it in the official introduction. We have a best selling author, a business [00:02:00] owner, a thought leader, and an all round terrific individual. But I'm going to put a plug on it right there. David, welcome to Deep Wealth Podcast. You're in the house of Deep Wealth. I absolutely love it.

And there's always a story behind the story, David. So what's your story? What got you from where you were to where you are today?

David Stillman: Thank you so much for having me here today. You know, What's gotten me to where I am today is I think there's personal and there's professional. On the professional front, I have always been one of those people graduated college. There was no post, studies for me. I was one of those people put me in the workforce and let me prove it.

And, you know, was always the one to show up five minutes before the boss, leave 10 minutes after the boss. And I think this worked. It's always careful because, I think there's been an element of luck but sometimes people, think, well, then I didn't have to work hard.

But, you know, I did have some opportunities where I was at the right place at the right time. But I think I had the ability to seize those and do something with it and really just turn every opportunity into a new opportunity and learn would be [00:03:00] on the professional side. And on the personal side I'm one of those people who's always been really independent.

I did spend a lot of time sort of alone growing up and It's no surprise to me that I ended up working for myself starting literally at age 26. So I've just worked for myself from that point on. And so it's no surprise. And at some point, it's a blessing and a curse. You get to the point where it's just like, I don't know another way.

And so this better work. And so I think seizing opportunities and taking that, strong independence. And I'm a huge risk taker. I love risk and it turns me on a lot. think those are some of the tools.

Jeffrey Feldberg: Well, David, you're incredibly modest. You have accumulated a tremendous amount of success, really. Changing lives, giving insights, making a difference, and not just with the best selling books that you've had, I know offline you're sharing how you're very passionate about startups and making a difference there, but let me ask you, let's go back a little bit in terms of in the first place, the whole [00:04:00] mindset of how you view the world, what that looks like for you, because you have a fascinating mind, where would you attribute that to in terms of what you see and why you see how you see it?

David Stillman: I think a lot of it is sort of sounds crazy, but do unto others how you'd want done unto you, right? And so I consider myself the most non judgmental person. I maybe have opinions, but I truly non judgmental and because I don't want to be judged. So I sort of like, well, I'm not going to judge you.

You don't judge me. And everyone's got a story. On top of that, no one's right, wrong, better, or worse, but that doesn't mean we're all alike, and so really understand those differences, those two factors for me, just being really non judgmental look for each other's differences, have really gotten me ahead, and at the same time, sort of, life is short.

Seize the opportunity, don't wake up one day and say, I wish I would've which, you know, a lot of people say, I never want to have regrets, which I don't think should be the goal either, because the reality is, we will all have [00:05:00] regrets, and that's not achievable, so it's more like, I might have regrets, Let's learn from them so that I seize the next opportunity,

Jeffrey Feldberg: And so with that, it sounds like, has that been, I'll call it your operating system from early on and you just took that with you?

David Stillman: 100%, I think it goes back as far as at the age of I was 17, I lost my oldest brother who was 23 at the time to cancer. So I really first hand got to see life is too short and Of course, there's a lot of sadness, but at 17, I was able to turn that into a lot of constructive things, being like, well, life is short, just go for it, and make it happen.

You just never know what's going to happen. You know, One phone call can change your life forever. Obviously, in the Best of ways, but also, you know, tragically as well. And so I think it really, a lot of it goes back to my childhood. Then I mentioned before I'd spent a lot of time alone where I had parents that were trying to take care of, you know, a brother that was so ill.

And so I [00:06:00] really had to fend for myself at a young age. my parents were amazing. Now, somehow they still made it to all my school activities and this and that, but yet still a lot of our attention was going to my ailing brother at the time. And so I really learn that independence at a young age, and that life is too short, and I really have taken that with me throughout,

Jeffrey Feldberg: What a terrific way of really being able to appreciate the present moment. And we hear so much about that. It's so easy to, well, you know what, I'm stuck on the past, or I'm really thinking about the future and we're ignoring the only reality that we have right now, which is right now here and now you and I talking to each other or whatever activity we're going to be involved in whenever we're doing that.

David Stillman: a hundred percent, and I think a lot of times we faced, tragedies, you know, could be 9 11, it could be what's happening in the Middle East, and everything, And we owe it to those people experiencing the tragedy. Let me be clear as day. There's nothing positive, Jeffrey, in my opinion, about those events. oh, and I choose my words very carefully. We owe them to find the constructive elements. What do [00:07:00] we learn from this? What are we going to learn to be better? in my case, the tragedies I've experienced, what did I learn from that to be a better? Partner, to be a better son, to be a better businessman, you name it.

And now dad, in a lot of ways, I take from those tragedies, again, nothing positive about them, but try to use the word constructive. And for me I guess it provides a little bit of sort of reason or sanity behind the tragedy.

Jeffrey Feldberg: sure. And my goodness, losing a brother at really such a young age. Did that change how you view the world coming out of that? And if it did, how did it?

David Stillman: few things. One is, I marvel at my parents. You know, You can't really appreciate until you have kids of your own, and so, to really appreciate what they must have gone through and how they were still there for, you know, I have another brother and myself, just incredible. So, just from that standpoint, amazing.

But also, yes, like I said, life is short. Go for it. Don't get hung up on the small [00:08:00] stuff. And I have gone on to be a leader that way in the workplace. To father that way, just don't sweat the small stuff. It is really not worth it. And so, in a lot of ways, that does drive me.

Jeffrey Feldberg: So let's talk about that because when you talk specifically about the various generations and the insights that go into who they are, how they operate, what their thinking is, many people, many businesses in particular listen, and you're really working with what I call the royalty of business. Some of these I don't know, smaller companies like Microsoft or the NFL or Virgin, 3M, Deloitte, to name a few.

So what's going on with that? You started on really, okay, here are the different generations, here are the differences with them. Here's some insights that you need to know. What got you on that journey in the first place?

David Stillman: Going way back, I was asked to do a story when I was doing producing work. I happened to be an intern at ABC years, years ago. And someone made the comment, we're doing a [00:09:00] story on Gen X, my generation. So, this is the in the 90s. And when my generation was really coming into the workplace and the comment was made, oh, you know, those slackers that hang out in coffee shops and have bad hair and listen to grunge music.

And I'm thinking to myself, really? I just put in an 80 hour week. I think I look pretty nice. You know, Maybe I need a little bit of a haircut, and I looked at my friends, really trying hard and I just thought, wow, are we stereotyped?

And I was like, I just was really fascinated by. How the world looked at Gen X, and then I sort of opened that up I'm a research nerd, so I can go down rabbit holes really easy on something.

I'm one of those people who know a little bit about a lot of things, and a lot of it for no reason at all. But just out of curiosity, but I just was fascinated by the baby boomers, sort of coming out of the go go 80s and being materialistic, yuppies, and some of those stereotypes, and it was, there's a lot of stereotypes about the generation.

And so I really got to know the different generations. Then [00:10:00] again, I kind of mentioned you earlier, I like to look for opportunities and seize them. I found that nobody was saying, well, what happens when we put these generations together? It's one thing to learn about a baby boomer, another to learn about Generation X.

What happens when you take these personalities and put them together? And what I really uncovered we had the making of was a new form of diversity. No different than how we look at race, gender, ethnicity, sexual orientation. We all look at these different forms of diversity to understand the person sitting across, the dinner table, the conference table just to understand them better.

And this was just another way to do that, was understanding generational differences. And it really launched, a great opportunity for me. And the reason I think. I maybe had it easier than other forms of diversity, and I still do today, is that this form of diversity is not laden with political correctness.

I just did it last week. I was literally in front of 1, 200 people in healthcare, stood up there, and I said, I put on the screen the [00:11:00] word millennial, and I said, when I say millennial, what comes to mind? People shouted out, entitled, babies, snowflakes yelled out things, and I was like, They're sitting right next to you know, if I had gotten up there and said any other form of diversity.

What comes to mind, not only that people's mouths have been shut, but I would have been cancelled. But for some reason, generational differences just, people put stereotypes out there, which opens the door to say, that's a stereotype. You need to work through that. And by helping them work through that, they can see that person sitting across the dinner table or conference table in a new light.

Makes them a better parent, better leader, better friend, you name it. And so, That's really what got me into this that just would allow me to take off. And more technically, I launched a study about the different generations and compared it and landed a great book contract with HarperCollins. And that really was the start of[00:12:00] the career.

Jeffrey Feldberg: And so the benefit of our listeners, and they've heard about the different generations and the names and the titles, but let's take it back to the boomers, which would be starting in 1946 up to 1964. Those are the boomers. And then Gen X from 1965 to 1979, then we pick it up with the millennials from 1980 to 1994.

And rounding things out for our listeners, the Gen Z from 1995 to 2012, one quick question for you, how's it decided when a year starts and stops for a particular generation? What's going on with that?

David Stillman: The first thing I say is like, we always put that, you know, we explain, because people just want to know what generation am I a part of, they immediately want to know, as it makes sense, and I'm really quick to say, age is a starting point. You might have someone be like, oh, I thought, millennials went until 1982, not 79, and I just don't get hung up on that.

Age is a starting point. Starting point. It really came from two amazing pioneers in the generational field Strauss and Howe, Bill Strauss and Neil Howe one of them's unfortunately passed [00:13:00] away, who sort of tracked the generations going back to, I joke, like the 1400s, like literally, and they sort of adopted every 18 years, there's been enough change in society that you see a different impact in the people.

But a better way to look at it, age is a starting point, but the true... Understanding and definition of this form of diversity is this, each generation experiences certain events and conditions that take place during their formative years. Let's break that down a little bit more. Those formative years tend to be between the ages of, say, 12 and 20.

You know, You're very impressionable. You when you're eight years old, you want to be a fireman. But by the age of, let's say, 12 or 13, you may be graduating to say, oh, I think I want to do this. And we really found that these events and conditions shape you during those formative years.

Because you experience these events and conditions during those formative years, you adopt a certain lens or what I call generational personality. That you look at the world. Now, people are always saying, well, does, you know, you're just putting people in a [00:14:00] box, you're stereotyping, and like, I am not. I am not here to put anyone in a box.

Does it describe every single baby boomer, every single Gen X er? No, it does not. But at the same time, there's enough data to show that as a generational personalities are very similar. And it really is no different than how we study other forms of diversity, gives more insight to Who's really inside that box when you're talking to them.

So I really want to be clear to all of our listeners. I'm not here to stereotype, but I've done enough primary research along with many others in my field to know that these events and conditions did result in a personality. Now, what we also know is that these personalities really have stayed with the generations throughout.

We maybe hit the same life stages, so we'll graduate, we'll get married, we'll get a job, we'll have children, we'll retire, whatever these different life stages are, however, each generation truly has reinvented or shaken it up and made it different because they're looking through that different generational lens, again, [00:15:00] going back, that was formed by those unique and different events and conditions.

Jeffrey Feldberg: And what I love with what you're saying, because David, I know some of our listeners, we may be losing them right now and they're saying, okay, you know what, David, you sound like a terrific guy and sure these different generations, it's interesting, but yeah, I'll kind of leave that more to the art side. It doesn't really affect me on the business.

And I would say actually it affects us in business. Every way, and I'm going to go to the Deep Wealth nine step roadmap and in our Deep Wealth Mastery Program, step number one, David, we call it the big picture. And in the big picture, we're looking at what we call inflection points. Some people call them blind spots and that's what's going on in the world, in society, that it's really small right now.

It's going to become a big trend later on that could either put us out of business. From our competition, from the marketplace. If we're not aware of it or if we're aware of it, we can leverage that. We can put ourselves outta business and go into a bigger business. So I'm gonna go back a little bit just to show you how far reaching this is.

As an example, back in the day, this would be back in the eighties. [00:16:00] When blue jean companies were all the rage and they were making gazillions of dollars of profit, all of a sudden they went from hero to zero because the teenagers that they were focusing on started to take their money to put them towards cell phones.

And cell phones, blue jeans, it's like comparing an apple to a Cadillac. It's like one thing to another. There's really, how do you even compare the two? Well, that's exactly what you need to do with an inflection point. And so you're right in the thick of that with what you're doing. And so for our listeners.

So, from a strategic side, from the business strategy of what we should know and what's going on with the work that you're doing, can you tie that together for us?

David Stillman: 100%. I mean, So what you just talked about was a customer segment. So we very easily could have a listener being like, well, I don't sell blue jeans and I don't sell cell phones, so it doesn't apply to me.

we all do have usually multi generations working for us. So I'll give you a great inflection point back going back to the 80s.

We had all the baby boomers, 80 million of them navigating the workforce. And we're figuring out policies and [00:17:00] procedures and internal politics of how they should be grown and retained in their careers. No one paid attention to the fact there was a new generation entering the workplace. You had 80 million baby boomers, you had close to half as many Generation Xers.

So Gen Xers, we didn't feel competitive. We walked into an interview and we're willing to start asking questions of the interviewer. What? Where Baby Boomer never would have asked a question, you know, they just answered them and whatever you said, go, because if I don't get this job, there's 80 million others.

So suddenly Gen Xers, no one was prepared for it. You also had Gen Xers that were not willing to pay the same price for success. And so, the workplace was not ready for that inflection point of Gen Xers. They tried to treat Gen X like the Baby Boomers, and whoa, did that backfire. It put me in business, candidly, so that was great for me,

Jeffrey Feldberg: Sure.

David Stillman: but you know, so there's a lot of inflection points.

So we might be looking right now, give an example of something I see often baby boomers are retiring. So what do we do? We're like, Oh my God, we've [00:18:00] got four people ready to leave the organization. We better go find four new people.

Get to the streets, we're starting to meet these new people like, oh my goodness, Jeffrey, they want to bring their dog to work.

They expect an iPad and we're like all freaked out how we get these new people in the door, right? Because that's what we're thinking is going to matter. No one's paying attention to what's about to walk out the door with those baby boomers. Loads and Loads and loads of knowledge that no one's gonna have time or money to pass on.

So this inflection point is, oh, I gotta go find ten new people. No John or Sally, they've had their great career here. But we don't look at the knowledge, so you might look at a box on an org chart and be like, I'm going to replace that box, but if we look at the knowledge, we might find oh my god, she's been in this job for so long, it's going to take us two if not three people to fill this role, or it's like, you know what, A lot of this stuff could be automated or disseminated.

We maybe don't need this box anymore. On top of that, you have a lot of baby boomers where knowledge has always been [00:19:00] power. And so what do They hang on to the knowledge so it makes them more valuable in the workplace.

And then you have baby boomers not willing to disseminate that knowledge.

So it's like we just don't think about some of these other inflection points that, are very generational. So I would say to everyone listening, you can give me any stage of a career at any time, and I will be able to point out all the different generational ones. For Gen X, for baby boomers, millennials, Gen Z, we all have them, but too often we're only looking through our own generational lens.

Jeffrey Feldberg: Yeah, I absolutely love that. And with what you're talking about at Deep Wealth, we say, hey, stop looking at it through our lens. Let's tune into the world's favorite radio station, WII. FM, the what's in it for me, for whoever you're sitting across the table from or having that phone call with. It could be a prospective client.

It could be a client. It could be an employee. Or a prospective employee. You're absolutely right. So let me ask you this coming out of the pandemic, based on the kind of generational [00:20:00] person somebody was, would that help you predict how they would react or maybe not react as the case may be from the pandemic?

Does it help you in that way? Or how do you leverage

David Stillman: A hundred percent. I could go, first of all, when the pandemic hit I made the bet that at the time we had the pandemic, people were not worried about the generations. We're worried about a lot of other things. So a lot of people who are speakers or experts, chased the virtual market. I did not.

I dove down into research. I'm like, I'm going to follow this. Now, I thought it was going to be a six month thing, not an 18 month bet. You know, So like, ouch. That being said, now, I watch to see what have, what's changed. And so it was a good bet, but I just thought it'd be a lot shorter than it was.

But so I could give you an example, take Post pandemic, we've got the remote workforce, right? And everyone's saying all these baby boomers, they're stuck in the mud, they're making us come into the office, but we don't look at it from a generational lens. for the baby boomers, 80 million of them, I sort of mentioned this, the time you got to the office was before the boss, the time you left, was [00:21:00] after the boss.

If you didn't like it, Too bad, there's 80 million others that will take it. So you couldn't just leave it for a t ball game, you just had to do it because that was a competition. So this is a generation that you always went to the office because if they saw me... That meant I was working.

We saw this in law firms. If you're not at your desk, you must not be working. So you'd have these young associates just hanging out the office just so they could be seen. So now remote working comes, and to a baby boomer, if they're on a Zoom, you know, and a cat runs in the background, or a spouse in their pajamas, it just feels really unprofessional.

Like no one's really working hard or working the same way. And if you were raised... That the office is where we're professional, where we get things done. It's just going to feel like the most logical sense to get work done. And so, perfect example. Then you take Gen Xers. You've heard in the past the phrase sandwich generation.

It was always used to describe the baby [00:22:00] boomers, because there's an era where the baby boomers had parents living longer. Depending on them, they're trying to, raise their millennial kids, get the job done, where, you always have to be at the office. So they were the sandwich generation burning out.

What people don't realize is that baton has been passed. Baby boomers are not the sandwich generation. The sandwich generation now is Gen X, because Gen X parents during the pandemic, that was the vulnerable population. So Gen Xers were now worried about their parents.

Trying to manage that. A lot of Gen X women had children later in life, so their kids could have been as young as elementary school.

So they're that big, and trying to manage kids and do homework at home, online, while managing their parents. It just became clear to Gen X, I am the sandwich generation now. And no one even identifies it. So what would I do? I'd be talking to my Gen Xers about burnout. I'd be talking to my Gen Xers about...

What benefits do you need? Is it, from bereavement to helping your parents to, sending kids to college? It's [00:23:00] just people don't realize that oftentimes Gen X is now the new sandwich generation to be looking at anything from culture to benefits.

Jeffrey Feldberg: And with what I love about what you're sharing with us, David, it sounds like when you can understand the lens of the person that you're speaking to, who is sitting across the table from you, it could be at the deal table. It could be at the employment table that you're hiring, or it could be a leadership moment that when you understand that you can be more relatable.

You can be more empathetic. They can really say, Hey, you know what? Jeffrey is being incredibly vulnerable here with me. He really gets me. I feel like I'm heard. And from there we create trust and we can create loyalty. We can get better results for everyone. It's a win, win. How am I doing with that? Am I on base, off base?

What would you say

David Stillman: 100%. And I'll go back to what you just said before, the WIIFM. What's in it for me is you will relate better to people. You will stop going to this place of thinking who's right, wrong, better, or worse, and just understand their differences. Now, you mentioned, you know, being a boss, being a parent.

What about being a salesperson? You [00:24:00] want to sell to someone from a different generation? Understand what they're coming from, and I've worked with tons of sales forces. Take off your generational lens. It might not be the feature or benefit that resonates with you, but understanding that generation, you're going to know what value proposition to put out there and land the sale.

So there's a lot in it for you in sales, but also, like we just mentioned, in leadership. You know, And this, like you mentioned, the pandemic, boomers. I meant to talk about X Factors, but millennials and Gen Z too, like huge. You know, If we look at the inflection points for them that the pandemic caused, I just want to talk briefly about the other two generations, because I think it's important.

If we look at the millennial generation, something to realize is like right before the pandemic, February, I would say, of 2020, millennials were really burnt out. This generation was, had really young kids at home, they're trying to climb in their careers, they were just really feeling stressed to get ahead and what the pandemic did is just gave them a chance to reboot.

It's like, you know, kind of turn off the computer and suddenly they're working at home and they caught their breath and they're like, maybe I won't have to pay [00:25:00] the same price for success that the previous generations paid. I can really do this from home and I can climb the ladder. I've got, I know what I'm doing.

And so when suddenly it came time to say like, we're going back, that was like PTSD. You know, Saying I don't want to go back to pre pandemic. I didn't like my work life then. It was crazy. you heard, everything from quiet quitting to all these things you see happen, they don't want to go back to that life at the same time, that doesn't mean they just want to go off and be alone.

The most collaborative generation ever. is a millennial generation. This is Facebook social media generation. They really more than ever are looking for ways to collaborate. So they want collaborative workplaces, but they definitely don't want to go back to the way it was. And oftentimes that's the trick for retaining millennials.

And then I'll quickly just touch on Gen Z. Cause this one I'm really passionate about in the pandemic is, they were the generation had no problem logging on. They weren't telling you to unmute yourself, like they got it. They were the ones that [00:26:00] just understood how do we do this?

How do we make it work? So, everyone just assumed, oh, they're fine. These remote workers, they're great. It's everyone else we got to worry about. Are they getting their job done and whatnot? And it's true, they operated technically just fine. But what no one is paying attention to is what got stripped from them is probably the biggest tool, how the rest of us got ahead in our careers, and that's our ability to build social capital.

The way people like you, me, and others got ahead, I mentioned it earlier on, it's I was at the right place at the right time. Whether it be, I stood around the water cooler and I had a conversation like, oh, I want to be a part of that, or I stayed a little longer at the meeting and I hear a conversation going at a table, you should join this task force, you should show up to this.

That doesn't happen on Zoom. If we're lucky, someone even turns on their video and at the end, it's like, no one can hit leave meeting quick enough. So if you're a Gen Z'er and you're new, where do you build social capital? Now a lot of people like come to the office. And I've done a lot of studying of this and a lot of interviewing and a lot of Gen Z'ers, what they're telling us now is like, okay, we're all back [00:27:00] to the office on Tuesday.

But when I go there, all the older generations are in their office, door shut, head down trying to get work because they're at the office for one of their days. So it's like if the door's not open anymore, again, where's the social capital? And that's one of my biggest concerns coming out of the pandemic for the youngest generation is their ability to build social capital.

And we don't realize how important that is.

Jeffrey Feldberg: So taking that forward, and what I'm hearing you say is when you can understand what's going on with the different generations, then in the workplace, as an example, the wonderful example that you just gave, okay, when everyone is back in the workplace, and maybe it's one day a week or two days a week, whatever that is, that from a cultural perspective, we can say, okay.

You know what? For a period of time, no one's in their offices, door closed. It's an open door policy or hang out at the water cooler, or let's just have some social times for people to network, get to know each other. Am I hearing that right?

David Stillman: A hundred percent, the problem is that, you go to the baby boomers, it's not as like, I can't believe we're sitting around playing pool, why isn't anyone working, I get it, so, I went to one office that turned their [00:28:00] lobby into pickleball courts, I don't know if we need to always go that far, but I think it's sort of this idea that maybe there's brown bag lunches, We bring in lunch and, we're gonna have two of our leaders talk about their journey and how they got ahead, how they see the future, to share, comes back to that knowledge transfer.

If you got some baby boomers who are eligible, retired, put them in a scenario where maybe they can share some of the knowledge that they have so it is being passed on. Or sometimes what we don't do is we don't ask the younger generations. We feel I'm the leader, I've got the most gray hair here, I'm supposed to be design programs and culture versus bring that newbie on, onto the task force and be like, what do you think it would take to get you and your peers to come into the office? How do you think you want to build social capital? What's it going to take? They'll tell you, but we often just don't even ask them

Jeffrey Feldberg: And so Dave, let me ask you this because I love what you're sharing with us, your insights, how you view the world. When through your work, I can understand the different generations, I'm going to make this up. Maybe I'm a salesperson or perhaps I'm a founder. Perhaps I'm even in customer [00:29:00] service. If I'm speaking with someone, perhaps it's in person or even over the phone, which might be a little bit more difficult.

When you understand the different generations, what their trials and tribulations are. So as an example, if you knew that I'm a Gen X, I'm kind of right plunk in the middle. If you look at that timeline, I'm more or less give or take a few years right in the middle of Gen X without. Trying to put everyone into a very simple category where all the same, I know there's always differences, one person to the next.

Generally speaking though, knowing that I'm a Gen X, does that help shape of, okay, Jeffrey's likely going to subscribe to this belief. He's probably going to behave this way. I mean, What's going through your mind?

David Stillman: 100%. It comes back to what I said, which we didn't unpack fully. It's, you know, they do keynotes and workshops on it, but each generation is shaped by events and conditions that result in A generational personality. So let's just use an example, a Gen X er. Odds are you grew up in a time where suddenly media had become 24 hours a day.

Compare that to a baby boomer who had news for a [00:30:00] half hour by Walter Cronkite, a news anchor. Walter Cronkite by Time Magazine was voted the most trusted man in America. There's no way you would ever vote a news anchor as the most trusted human being in America. There's no way, because what did you see?

You saw thousands of hours of television, 24 hours a day, there was no TiVo for you to fast forward anything, and we watched all these institutions and leaders called into question again and again and again. The other thing we know, and I have no idea if this is your scenario, I was blessed that it wasn't, but during the birth years of Gen X, the United States divorce rate tripled.

So a lot of Gen Xers saw the demise of, not only institutions on television, but the most sacred one right at home, the family unit. No one was monitoring us. Like we could leave our house, ride a bike, ooh, without a helmet, and whenever we got home, we got home. So I know for a fact, odds are a couple of things.

You're going to be extremely independent thinker. You're not going to do things just because everyone else, you know, and not always look for status [00:31:00] quo. But probably an overriding fact that you're going to have compared to a baby boomer is you're going to have a level of skepticism. that no one else has.

But I was talking to a baby boomer, it's going to be more idealism, optimism, we could put a man on the moon, civil rights, human rights, voters rights, women's rights, we can change the world. If I'm going to talk to you, it's going to be like, prove it. So anything I say to you, I'm probably going to want to back up with data, I'm going to be less idealistic and optimistic, I'm going to just be a little bit more tap in and prove that skepticism.

I mean, I know you're an independent thinker, so I'm going to say something to you like, What do you need to go try to sell this internally? Because I know you're probably, sort of that lone soldier trying to make it happen internally. Actually 9. 5 out of 10 times, I'm spot on. Just because I tap into that generational issue.

Jeffrey Feldberg: Matt, you took the words out of my mouth. You are spot on with everything that you said, and I can relate to exactly what you're saying, which, wow, I mean, talk about being relatable and then trustworthy and oh, you know what? David gets me, I can open up to him, I can share things with him that perhaps I wouldn't to someone [00:32:00] who doesn't get me or I feel doesn't get me or doesn't try or doesn't understand.

So I know you've channeled this into helping startups. And again, for our listeners who, you know, if they were skeptical coming into this and now you're starting to shine the light of why this is so important to understand how, hey, this generation thinks like this, while that generation thinks like that.

When you're working with some of the startups and you're really paying it forward out there, David, of taking what you've learned, making a difference out there, how are you taking all of this massive knowledge and these insights and helping these businesses, really they're up against the trend. They're the underdogs of getting above the noise, making a difference and actually succeeding.

David Stillman: Well, a couple of things. The one, I think in general, these lessons apply startup or huge institutions like the 3Ms of the world. They really do. You've got multi generations trying to work together, whether there's Thousands, or even a team of five, if you got multi generations in the room, or, what your customer base is, if you're selling a product that's targeted to millennials, I can give you [00:33:00] insights there.

So, I think, cross the board, it really relates. What I'll tell you is, What I find is the best solutions have all generations at the table, regardless of tenure. So sometimes we sort of think that the older ones with gray hair have the most to say because they have the most experience.

True, we should learn from their experiences and we shouldn't just have, you know, someone young, but at the same time, that person who's young and only been there three weeks, they bring a value perspective as well. So I find The work initiatives that have all generations at the table the best.

So if you're like a really young startup and you're just a bunch of 20 year olds, I would say make sure you get an advisory board that's got Xers and Boomers, in there as well. And for sure the other way around. So, All voices at the table, and of whether or not they're your actual employees, and from advisory role, I, that's one thing I really preach, to understand both the workplace, the internal team, but especially the marketplace that you're trying to sell to.

The other thing I would say is, I find a lot of times that if we look at all four [00:34:00] generations, Boomers, Xers, Millennials, and Gen Z, Boomers tended to, In the whole to parent millennials and Gen Xers tended to parent Gen Zers.

We look at who is going to be a little bit more wired for startup and risk taking.

It's going to be that Gen X and Gen Z versus a boomer and millennial. And here's why 80 million baby boomers, you would never leave a company. to go start your own. And if you did, wow, is that a big risk. It better work because you were stepping out. You weren't going to go up anymore. It was such a big deal.

Well, for Gen Xers, we never had that. We could leave a job, try to go start one. And if it didn't work because there was 80 million. Half as many of us, we could always get a job going back into the workforce. No matter what's happening with our economy, Jeffrey, it'll always be a Gen X job market. Just do the math.

There's this half as many of us to fill the spots of the baby boomers. So Gen Xers, we were wired. We're willing to challenge status quo, We're willing to tell our Gen Z kids, yeah, go for that, just [00:35:00] go for it. A baby boomer sent their millennial kid to college at any cost.

No matter what. You got millennials now sitting on mounds and mounds of college debt. Gen Xers, we're telling our Gen Z kids, well, college isn't the only answer. We now have 75 percent of Gen Z who believe that there's other ways of getting an education than a four year degree. Doesn't mean they're not going to college, but you know, we were always open to alternative paths, taking risks.

So you have a lot of Gen Zers and Gen Xers really align on that. They really align well on it. So, we find, for example, today, how does that play out today? I don't have the exact number, I think it's either between 69 and 71 percent, so don't quote me exactly. Oh yeah,

Jeffrey Feldberg: enough.

David Stillman: but we're just in there of Gen Zers entering the workforce.

Have a side hustle. That means that when they come work for you, whether it be, like I said, 3M, General Milk, big companies, small companies, they've got a little business going on the side. [00:36:00] Now, people like you and me are baby boomers. We might have had that on the side, but we called it moonlighting. And it was definitely a hush.

We made some dollars. We're almost a little embarrassed about it. We for sure just, we're quiet about it. Gen Zers have their website up, their Etsy site's up. They're selling stuff all day long. They've got a side hustle. And you never would have seen a baby boomer tell their millennial kid to go do that, but you'll see a Gen X er tell their Gen Z kid to do that.

So if I look at startups, I find just generationally X ers and Gen Z, the most sort of wired for startup.

Doesn't mean that millennials and baby boomers can't and won't, they're just wired differently around the notion of a startup.

Jeffrey Feldberg: That's interesting. Yeah, no, it does because when you have that kind of insight, regardless of where you are in the spectrum of being a founder who is hiring, or you're looking to go perhaps work at some place, on either side of the table, when you know who you're dealing with, what that likely is the case, you can make better decisions, more informed decisions.

So let me ask you this, because what I love what you're [00:37:00] doing is saying, hey. It's not that one generation is better than another, actually quite the opposite. Really the best solution has all the different generations at the table. They're part of the process. So let me ask you this, because if there's one area that's given people a lot of challenges, it's been very divisive and it's come on very strong.

Lately, a lot of companies just don't know how to deal with this. It's the diversity question. And I know diversity is very important to you and you've been on both sides and you straddle that and. Knowing what you know, where you've been, your own personal journey, and also with the different generations, how do we deal with diversity?

Because with social media now, what we say is, and will be used against us forever. And even not saying something can be really working against us. So what's your thoughts on that?

David Stillman: , I see generations as... No different than any other form of diversity. And so oftentimes, I have found, I get brought into a DE& I initiative or a company because generations is the easiest to talk about. Well, if we can [00:38:00] tackle, you know, generational differences, we can dive into gender or race easier.

So sometimes, just starting with generations is a good place to prove it. But beyond that, when it comes to the topic of diversity and inclusion, We can look at historically the generations. And my sort of frontline advice in a short amount is let the younger generations lead the way and the conversation.

They know how to do it better, they're better at it, and they're very aware and more comfortable. Part of the reason is, for a baby boomer they never had a diversity HR. There's diversity within it. By my generation, it was starting. By millennials, diversity departments were really starting to thrive.

So if you take a lot of the people leading companies, boomers and Xers, without realizing, it's almost like PTSD, if you were being sent to the diversity department, it was usually meant you were getting your hand slapped. You used the wrong terminology, you offended someone from the opposite sex, you had the wrong label, you didn't even realize it.

And so you're sort of [00:39:00] getting course corrected. We're starting with Millennials, diversity and inclusion was all about how can we be better, assumed you don't do those things, and so Millennials and Gen Zers really are just better at having the conversations, asking, saying why would you do this, being more aware of it where I think a lot of the older generations are always worried about that hand slap versus just asking and embracing it.

Now the other thing to also realize is You say diversity to a lot of boomers and Xers, they're still sort of thinking about, those boxes we used to check. White. Black, Asian, Hispanic, or Other, to sort of capsulize everything. Other was the other one, you go to Millennials and Gen Z, and it's Others not only embrace, but now we have everything, and I'm not kidding you, from signs of the Zodiac, to, what your pronouns are, to, they've just been able to take diversity so far.

That I think, unfortunately, for a lot of the older generations, just feels overwhelming. They just feel like, I'm gonna be not, I'm just gonna be damned if I [00:40:00] do or don't, I'm just gonna be damned if I just try to even go there, and I think a lot of times people be like, oh, so then I better go hire someone of color to run diversity, let myself off the hook.

I definitely think, for sure, someone who experiences diverse struggles, Should run the department. That's fine. But I think too often, I think it's an excuse for some to be like, okay, the right person's handling it. No, as a leader, you need to be as aware as they are. And I say that and people in an audience always look down.

They don't look at each other. I'm making them very uncomfortable. But I said. I think

the younger generations You know, are the ones. How many parents have said, my kids are schooling me all the time on, how to refer to somebody, or how to call them, or what to say, and it's because they just get it. And so I think too often the wrong people lead the discussions of the older generations, when I always lean into the young.

Jeffrey Feldberg: Yes, and agreed. I'm guilty as charged often at the dinner table. I have two daughters and both Gen Z, and I am constantly being cracked at daddy. No, that's not [00:41:00] how you say it. You can't say it like that anymore. You're way out there. This is how it's got to be. And it's an education for me and really a different way of looking at things.

But truth be told, and don't tell them this, they've opened me up and I now take out much wider and more open stance.

David Stillman: No, I get it. And the thing is to remember your intention was never to insult, and those whose intent are to insult and really offend, odds are we sniff them out and they're getting fired for something, you know, or they really messed up and they should leave, but not, you know, most of the times when somebody sort of uses the wrong term or says the wrong thing, that is not their intent.

Doesn't mean they might be extremely ignorant and they don't need to be woken up a little bit, but If we hand slap them and sort of, we're going to make them too scared to explore. So again, the ones that are just the best at it are the younger generations.

Jeffrey Feldberg: And speaking of children, I know your son Jonah is now playing a role in what you do and making a difference out there. And for our listeners, you can't see David, obviously I can. He [00:42:00] is grinning ear to ear. I just mentioned Jonah and wow, he just lit up. So what's that David, as seeing your son as really a father and becoming his own thought leader, his own man, going out there into the world and taking on this message.

What's that like for you?

David Stillman: Well, it's great. I could not be more proud of Jonah but, Jonah had the luxury of, intense bootcamp by me, and let's just keep it real. The things I could say to my son in coaching him, I could never say to an employee. I really got to beat it into him, and a few things that he really learned. I always taught them, beware the focus group of one. If you're going to get on a stage or in front of a group, you speak to the data. If someone says, do you like the color purple? And you don't, but the research says that Gen Z does, you say, my generation likes purple.

Really, when he gets up there, he's speaking to the data and he truly, I said, that's being an expert.

The other thing too, is pride ourselves in calling an expert. There's a lot of people out there. And if any of you are listening, know. Criticism, who are great speakers, who love the topic, [00:43:00] go ahead and read our books and others, and then go speak on it. I will call myself an expert because we field our own research, and so it's sort of been that, research nerd in me.

And same with Joe, and I tell him, you know, like, we run our own research, we make sure it's valid research. And then beyond that, what I'm really proud of him is he's got guts. I mean, He'll get up in front of 1, 500 people and give a keynote and just nail it. And he's taught me a lot. Granted, I come from the field, but I take off my own generation lens, and a lot of the business has evolved because of Jonah, the things I never would have done, that we for sure do, and I'm really proud of him, so proud of him.

Jeffrey Feldberg: That's incredible. That's very fulfilling. And you know what? It's a great example. Hey, when you're open, the teacher often learns more than the student. And it sounds like what Jonah's doing, what you're teaching him, he's giving right back to you, maybe even tenfold. And off you go with that, which is incredible.

And speaking on the personal side, I know I'm all over the place here. There's a method, of the madness though. I know offline, you're sharing something really interesting with [00:44:00] me. What I really admire about you, David, is you. Follow your passion, whether it's in vogue, not in vogue, there's some kind of rainbow at the end or not, you're still doing it and congratulations.

You wrote a, well, I'll let you tell the story of that you wrote something. It was purely of personal interest, purely from passion. And you won, you, you got this incredible award, the Best of Fringe. So what's going on with that? 

David Stillman: Thank you. So I've been blessed to write three best selling non fiction books. And, the thing with non fiction is it's data, it's true or false, you have an outline. Candidly, I always thought it was easier to write. I always had a fantasy to write fiction. For years and years, but I always thought, ah, it doesn't make money.

I can't do anything with it. It's a side. I don't have time to do a side project. And I put it off and lesson learned. If I were to tell someone starting off in their career, you find time for side projects and side things from day one. it's just a must. It just nurtures your soul creatively.

All the above. I waited too long, was what I learned, but I finally took the time and I wanted to really [00:45:00] challenge myself and write fiction, and because I had written books before, I wanted to try a new format, and so I wrote something for the stage, and I wrote a one person show, not performed by me it's a musical, so I got to experience writing lyrics and work with a composer, and wrote this one person show, and it was so fulfilling, and I did it during COVID when a lot of things were who It's tough and I had more time on my hands.

And I wrote it. And the funny thing is I just wrote it and put it back on sort of the shelf of my computer and didn't do anything with it. And then a few years later, I was like, what are you waiting for? You've got nothing, and part of it for me was just writing it. I pulled it out of the folder, I always joke, no one finds me funnier than me.

So I, I read it and I'm like, yo, this is still funny, I think. And I entered it into the fringe, you know, was lucky enough to get a spot and It was performed this summer by a wonderful actor, I had a great director, and a musical director, and it was such a fun project, and yeah, it won Best of Fringe, and now the interesting [00:46:00] thing is there's producers looking at taking this show around the country to other markets, and When I got into this, it comes back to, I said, this passion project, it was truly just the passion to do it.

It really was sort of, I just wanted to do it. Checklist, bucket list item. And the lesson learned is probably going to be one of my more successful things that happened to me because there wasn't some commercial value. There wasn't some bigger intent other than nurturing my creative soul. And sometimes those projects end up to be the, I don't know if it's a sleeper or whatever you want to call it.

But the ones that actually have some commercial success and viability because you were just driven by true, just sort of creative and art. It's been an incredible journey and what I thought would be done when the fringe was over, but lo and behold, I'm finding myself now on learning the business side of things and how to maybe take this to the next level.

I'm back in startup again, you know,

Jeffrey Feldberg: And what's interesting, David, look, you have three best selling books. You've been on USA Today. You've been on CNN, CNBC, [00:47:00] the Today Show. I mean, You've been out there. And you've experienced success, but you're so humble. So when you wrote this, it was, Oh, geez, I don't know. Is this going to be something that people are going to like?

Maybe I put it out there. Maybe I don't. And the takeaway really for our listeners, Hey, keep it real, be humble. But also you took the chance. Okay. Well, you know what? I did it anyways. I still like it. So let me put it out there and see where that goes. So you took that risk. It would have been very easy just to sit there, collect dust and nothing to happen for it.

But Hey, you didn't do that. And look at that. You won the best of fringe. So congratulations with that. 

David Stillman: I will say to you too, I think in that journey is sort of a lesson for startups. Putting it out there, it's a startup, no one's seen it before, people are going to need some money for it, and you want them to like it. And you touched on a couple of key points for your startup listeners. One is, you gotta take a risk.

I always say, if you wait till it's perfect, you waited too long.

Get it out there, you gotta get some feedback and if you're just ready aim, and you never fire you're never gonna know. So it's take the risk, and number two, and it's, everyone says this, but go with your gut.

About that [00:48:00] process, it's do we do this or that? I just would have a gut feeling, and I'd get a lot of different opinions, and again, no one was right or wrong or different, no one's gonna get, hurt along the way. I went with my gut. And on this one, because I didn't feel, it just felt right to truly listen to my gut at all times, I will say that taking the risk and going with my gut really paid off, and I think those are lessons for anyone going into startup.

Jeffrey Feldberg: Absolutely. Some terrific insights. And you know what? It never gets old, these best practices. That's why they've been around and hey, follow your intuition, follow your gut. Maybe it's a universe speaking, maybe it's higher up, who knows, but listen to your gut. Follow that hunch because there's usually something that's there with that.

Well, David, let me ask you this before we go into wrap up mode, and sadly we need to go into wrap up mode. We're bumping up to some time. We're For every episode, wherever possible, we love to be one takeaway, one action item. So before a listener goes into that next meeting or that phone call or activity, if they could do one thing, and David, you could draw upon something from any [00:49:00] area, what would this one action be that could really help a listener move that dial for him or her and really make that difference?

David Stillman: I've mentioned it before, but I think it's the most powerful one that's going to apply to a lot of different things around the generations, is When I see someone bump up against someone from a different generation,

Whether it be that person who walks in and their shirt's untucked, or, you know, it's going to be the person who won't come into the office, or that customer who's just grilling me and grilling me and that skeptical side of things, you know, it's sort of like, We always go to this place of judging who's right, who's wrong, who's better, who's worse, and we don't realize it's just so generational, you know, it's like, Every day I walk ten miles uphill against the wind, it's sort of like that whole era of right, wrong, better, or worse gets you nowhere because no one is.

If you can rather, it doesn't mean you have to like it, but be like, okay. This person and generation is just different.

I gotta accept that. If you realize, you stop going right, wrong, better, or worse, you realize, wow, I now have an [00:50:00] opportunity to understand why they're different.

So why is Jeffrey always so skeptical?

Well, he came of era during the time where everything was called into question. no wonder he's so skeptical and always asking for proof. so it's just these little generational nuggets. And so, if you're inclined, go learn about these differences. But at 101, if you walk into that office and you find people doing and acting You know, differently than you are looking through a different lens, your goal should never be right, wrong, who's better, who's worse, it's just different.

And then I'd say go one step farther, leverage those differences, make sure you've got all voices at the table, because that's where you're going to get the best teamwork and the best solutions as well, for sure.

Jeffrey Feldberg: And so not to oversimplify, and please, you'll correct me if I'm off base with this, what I'm really hearing you say is when you see a difference that maybe would otherwise be aggravating or what a pain in the you know what. Become curious and go below the surface. Why is this happening? And what do I need to know about this?

And how can I leverage this for a win, win all around?

David Stillman: Yeah, how often do [00:51:00] you go out to lunch with someone from a different generation and be like, tell me about a formative event that shaped who you are today? No, we just don't do that. We just think they're looking through the same lens. We think about how someone grew up today, you know, a millennial's economic landscape when they were sitting around the dinner table were the go 90s.

You could be anything. A Gen Z er hovered around the 2008 recession, where it's just like, You're in survival mode. So no wonder that, an economic viewpoint from a millennial versus a Gen Z er is radically different. But we don't take the time to understand these differences. We just sort of, like I say, look through our own generational lens, and that's why I love what I do.

Jeffrey Feldberg: Excellent advice and some insights. So with that, speaking of insights, let's go into wrap up mode. It's a really fun question and it's a tradition here in the Deep Wealth Podcast. Every guest I ask this question, it's really an honor and a privilege. Let me set this up for you. So when you think of the movie Back to the Future, you have that magical DeLorean car that can take you to any point in time.

So the fun part, David, is tomorrow morning, you look outside your window, not only is the [00:52:00] DeLorean car curbside, the door is open and you're gonna hop on in to go back to any point in your life. Perhaps it's David as a young child, a teenager, whatever point in time it would be. What would you tell your younger self in terms of life wisdom or life lessons?

Or, hey, David, do this, but don't do that. What would that sound like?

David Stillman: Wow. I mean, I think there's so many different points in my life, can I make a few stops along the way? I

don't know. I would. It's just different. I think there's the business side and there's the personal side. I think on the business side, I would go back and tell myself that the alternative path, isn't always a bad path.

Alternative doesn't mean bad. And so like when other people were going on to graduate school or getting jobs, I took a backpack and went around the world for a year, there's this different. Pines, where I took the alternative path, and it served me right. So I would say I'd go back to those points and tell myself alternative doesn't mean bad or offensive or wrong, it's okay and to go with my gut at those times, and I did, it [00:53:00] really paid off, and on the personal side, I think there's this time in my life where I would go back and tell myself, Everything is going to be okay.

Yeah, you're going to be okay after my brother died, like you'll still get to live a full life. I'm a person that's experienced, some of their own personal diversity as well. And in that journey, just go back and tell myself you're going to be okay. Really, it's going to be okay.

Jeffrey Feldberg: Some great advice. And you know what, there's a few different themes that come out from that question. And really word for word, what you said, everything's going to be okay, is one of those themes that come out. So you're in great company and it's some terrific insights. David, let me ask you this for a listener who perhaps wants to have you for a keynote.

And I know you're an illuminating. Keynote speaker, or wants to bring you into the company to help them with some research or an initiative or startups out there. And they're saying, Hey, we need David to be in this company and give us some strategies and some insights. Where would be the best place for somebody to reach you online?

Oh,

David Stillman: Two things. One, I'll say what's also really cool in the keynoting [00:54:00] front is I also often do it with Jonah. So Jonah and I come together, so you get the Baltic generation, father son dynamic, and that tends to be something really popular, you know, because you get a gens here too. So that's That's a great offering, I would say.

Two places. One is LinkedIn. I'm active on LinkedIn. I'm always putting new data or insights out there. It tends to be generational or business. It's not I ate toast today,

definitely going to be business. So LinkedIn, like for sure, connect with me. Otherwise, website, GenGuru, G E N G U R U dot com is another way to get in touch and I do respond to all those requests and everything.

They come to us directly. I'll never be one of those people, who doesn't get right back to

Jeffrey Feldberg: Terrific. And you know what, for our listeners, it's all in the show notes. It's a point and click. We'll have the website. We'll have all your books listed out there. We'll have the LinkedIn. We'll have all of that there. So go to the show notes and it couldn't get any easier. Well, David, it's official.

Congratulations. This is a wrap. [00:55:00] I've really enjoyed my time together with you today. And as we absolutely love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. Thank you so much.

David Stillman: them. Thank you.. And you know, with shows like this, people like me and others are inspired to do so. So thank you for truly having me on today. It's been an honor, Jeffrey. 

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Kam H.: I would highly recommend it to any super busy business owner out there.

Deep Wealth is an accurate name for it. This program leads to deeper wealth and happier wealth, not just deeper wealth. I don't think there's a dollar value that could be associated with such an experience and knowledge that could be applied today and forever. 

Jeffrey Feldberg: Are you leaving millions on the table? 

Please visit www.deepwealth.com/success to learn more.

 If you're not on my email list, you'll want to be. Sign up at [00:58:00] www.deepwealth.com/podcast. And if you enjoyed this episode, if it added value, if you walked away with some new insights and strategies, please leave a review on your favorite podcast channel. Reviews help us reach new listeners, grow the show. And continue to create content that you'll enjoy and as we wrap up this episode as always please stay healthy and safe.