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Jake
I didn't want to go. I didn't want to go. Honestly, all I really wanted to do, as lame as it sounds, was go home and like, cry. In what world can you say that to your boys? Like, hey guys, I'm going to go home and have a good cry. And you just, you just don't.
Michael Chernow
Is masculinity the wrong term for what we're trying to describe here?
Jake
A man nowadays knows how to be in his masculine and in his feminine and doesn't have a problem with that, can be man enough to do feminine, say the feminine thing or have a feminine feeling and express it. That to them is the sexiest, most attractive, most manly thing you can do. And I agree with it. To look a woman in the eye or another man in the eye as a man and say, I'm sad.
Michael Chernow
Masculinity was never a bad thing when I was a kid.
Sponsor/Ad Voice
Like, it was like, you heard the
Michael Chernow
word masculinity and you were never like, oh, that's toxic. Never an entrepreneur straight out of New York City.
Jake
Michael Chernow, what's cracking?
Michael Chernow
Putting all potential pushback aside, putting your podcast aside, there was obviously a reason why you wanted to talk about masculinity prior to the podcast. What we, what did you go into? What was your thought process going into this podcast with that being somewhat of the impetus or, or theme?
Jake
Yeah, there were. There were two, like bookend moments over the course of almost a decade. One was like right when I graduated from college and then the other was right before I started this podcast. It was a 10 year journey in my 20s. So right after college I had a really, the first like rough patch I've ever had all in one basically day. Well, weak girlfriend. Who, you know, first girlfriend, we had a bad breakup. She broke up with me. I didn't want it to end. She had to go find herself in Europe. No 21 year old's ever heard that before, I'm sure. Best friend attempted suicide and then had a family health scare on basically the same week. So I was like, oh shit, this is, this is what pain is. It's pretty foreign to me. I mean, I of course had like some adversity growing up like any other kid from a divorced household and whatever. But the mix of not being able to sleep, not being able to eat, just feeling a lot of what I would call just a bout of depression and anxiety. And then on top of that, the loneliness of that, it was my first time experiencing all that stuff. And I was out one night with a few buddies on A Friday night, maybe Saturday night, grabbing some beers. And I was not that engaged, but they were. And I think it was like four or five women. And then three of us, four of us. They're like, let's go to another bar. It's like nine o'. Clock. I didn't want to go. I didn't want to go. Honestly, all I really wanted to do, as fucking lame as it sounds, was go home and, like, cry. But, dude, in what fucking world can you say that to your boys? Like, hey, guys, I'm gonna go home and have a good cry. And you just. You just don't. So I kind of said, like, all I really could say, which was just like, you guys go, I'm gonna. I'm gonna head home. Everybody's like, dude, best friend. He's like, dude, what are you doing? Like, you need to get laid. Just get laid. Like, the scroll's all over you get laid. I was just like, dude, not tonight. I'm gonna go home. All I really wanted to do in that moment was punch him in the face and say, can you shut the up right now? Like, do you have any idea what you're saying to me? But there was no language. I had no idea how to handle that situation. This is my best friend. He didn't know how to handle a situation like that. And so eventually I was just like, you go, I'm going home. I just went home. That was that. There was no fight. It's like, woke up the next day and moved on with our lives and never came up again. I'm going to come back to that. I went through them my whole twenties, having never really forgotten that, how that felt, um, why that happened in the first place. It wasn't just me. It was also a lot on him, but it was also on just, like, guys in general. Like, if we were women in that situation, that would have been handled very differently. That would have been like, oh, my God, honey, let's go to your place, let's get some ice cream. Let's talk all night. Let's hug it out. Like, women know how to fucking handle that stuff. Oh, you don't want to go out with these guys?
Michael Chernow
Great.
Jake
No, we're not going to go out with these guys. Thank you for speaking up. Let's, like, they know how to handle this stuff. We never learn how to handle that shit. It's just, go get laid. Go grab a beer. Go work out. Okay. So throughout my 20s, Moved around a lot, did a lot of stuff, started companies, sold one, raised a fund During COVID took a lot of risks, did a lot of big endurance events, got into jiu jitsu, competed, got my ass kicked, failed a lot. And throughout all of this, confidence developed and I no longer had a fear of looking at a homie and just being like, hey man, don't appreciate this how you're talking to me, I'm gonna go home, have a good night. Like, just don't care anymore. But at 21, I didn't know that. I've asked a lot of questions to a lot of really, really smart people about how do you just handle life in all of the ways? Some examples are, what do you do? I remember asking a mentor of mine, like, hey man, he's 50 year old guy, has two kids, one was in college, one was in high school. It's like, what do you do when you have a really shitty fight with your partner on a Sunday night? Your romantic partner, and then you got to wake up on Monday morning and give an Investor presentation at 8:30 in the morning. You just got to do it. And you didn't sleep at all, you haven't eaten, could barely get a piece of toast down that morning. How the, like, how do you do that? And just like shut it off. And he was like, man, I've been married for 27 years. If you find the answer, please give me a call and let me know. I, I don't know. No one knows this stuff. Okay, that, that's one example of hundreds, maybe thousands of questions I found myself asking over the course of a decade. But I never did anything with the answers. I just applied them to my own life and realized, slowly but surely, I realized no one's putting this stuff out there. The only two people or types, people that are putting this out there are very extreme ends of a spectrum. Andrew Tate on one side of the equation, and I'm very much against him and what he is saying and the communities that are following him. And the other side of the equation is like the soft shaman hippie feathers and sage in the whole nine yards. And it's actually very feminine. Really, nothing in between. And I thought, okay, look, I, I'm not the expert. I'm not a doctor, I'm not a psychiatrist, I'm not a men's coach. I haven't studied masculine any more than just like talked about it with a lot of cool people. But I know social media and I know how to make podcasts. I know how to storytell and I know how to get in touch with people. I know how to yap so why don't I just go out and ask the questions that people are either afraid to ask out loud or don't know to ask out loud. Put it on camera and just put it out there and see what happens? Because there's no way. There is no way I'm the only guy who's struggling with this stuff. So I first hit up a handful of friends who were kind of mentor types to me, and then had I just rolled tape and I was like, let's just talk about a thing and see what happens. And then I asked them, who do I talk to next? And next thing you know, we've done a year of. Of conversations about, about this stuff and learned a lot. And there's been a lot of interesting patterns. There's been a lot of interesting responses that have come up. That's the backstory. So to sum it up, 10 years of just exploring it for myself, trying to just basically one, like, be a better man, Be a awesome man, and then start preparing myself for how do I raise my son one day.
Michael Chernow
Okay, so you finished our podcast episode of the question, what is modern masculine masculinity? Or what does masculinity mean to you now?
Jake
What does it mean to be a man nowadays?
Michael Chernow
What does it mean to be a man nowadays? What does it mean to be a man to you nowadays?
Jake
Yeah, my answer is, it is the same answer it has always been for centuries, which is to provide and protect. But nowadays those words mean some new things. Provide kind of always meant provide financially and provide shelter and food, which costs money. Still, financially. And protect always meant, like physically protect the family from harm. Sabertooth Tiger is always the example. And now I think there's a whole category to both provide and protect that is emotional. How do you provide emotional safety to your woman or your kids?
Michael Chernow
How do you.
Jake
There's a lot of ways. Hold space is a term that I think is very misunderstood and thrown around and actually not spoken about enough. You got to learn how to fucking hold space. You have to learn how to hold frame.
Michael Chernow
What does hold space mean?
Jake
I think hold space means to shut the fuck up and just listen, ask questions and listen and just be a safe, warm body, both physically but also emotionally and spiritually. For someone else to just kind of get their off their chest, whether it's directed at you or bitching about someone else, whatever, just like, be there and just, like, listen.
Michael Chernow
You know what? I have learned over 20 years of marriage, and I'm sure you've heard this before now, specifically being in the podcast that you're in. What I've learned is, and I don't know how dissimilar it is from male to female, but I do know for
Jake
sure
Michael Chernow
that as a husband and I think men are wired to want to fix. We're wired to want to fix problem arises. We want to like fix it as fast as possible. Of course, what I've learned is being as, as, as now, being a husband
Jake
for decades,
Michael Chernow
my experience is, is that women don't necessarily want you to fix their problem. The providing, which would ultimately be like fix something traditionally for women, I think makes more sense just providing that holding space piece.
Jake
Yeah, I use the word, the phrase provide safety. Provide safety to people around you, protect them. That's another way to put that, which is provide and protect like providers. Emotional safety, physical safety, spiritual safety, etc, and oftentimes if you think about it, like, how does it feel when you go to somebody and you, you share an experience that you're having that you're struggling with, maybe like you're, you're having a really hard time with your boss or whatever, and this person just keeps trying to like, offer all these solutions, but you're like, no, you don't, like, you don't fully get my therapist. The situation, like, I can't explain. I, I don't know how else to explain it, but like you, that, that's not going to work. It's frustrating. I think any human, let alone any guy, has at some point felt something like that before. I think for women it's like a hundred times that all the time with guys. I said this to my dad recently, almost jokingly, but he was like, I was like, look, I feel like when a woman shares an experience she's having, whether it was a bad day or, you know, something she's frustrated about, whatever. We're like, why don't you just do this? Like, it's pretty straightforward. It's like, no, no, we don't. They don't want to hear the solution. They just want you to sit in the mud with them and feel how it feels to deal with it, to be like going through it. That's it. Like, just sit next to them in the mud, put your arm around and be like, yeah, this is like this. I can totally see how this sucks. And then shut the up and like, it's gonna work out a lot better than if you're like, well, why don't you just do this?
Michael Chernow
So would you say for, for men that are in relationships, like. Because my answer to your question was, was self Awareness.
Jake
Yeah.
Michael Chernow
Right. Like, the more self aware you are, the more capable you are of doing the things that we're talking about doing. Right. Self awareness, patience, pausing, giving yourself some time. Like, because typically, you know, the window breaks. You like ime. You see it immediately. You know, they're cracking the window, Cold air is coming in. It's a winter time. You're like, oh, cold. Calling the window company. You know what I mean? Like, that's how I think men are typically wired. Right.
Jake
Right.
Michael Chernow
And we don't have like the. We don't necessarily have the ability to distinguish between the broken window, cold air coming in, and when your wife brings up a problem that she's having at work, it's like, broken window, call the window company, wife has problem at work with coworker. This is exactly what you should say to that person.
Jake
Yeah.
Michael Chernow
You know what I'm saying? It's like we have a hard time distinguishing.
Jake
Yeah.
Michael Chernow
The, the, the difference.
Jake
Totally.
Michael Chernow
So for the person that, like, is battling with their partner.
Jake
Yeah.
Michael Chernow
Whether it's, you know, woman, man. Like, do you like, what would be advice based on, based on not only what we just talked about, but like conversations that you've had from whatever 40, 50 people that you've interviewed on your podcast.
Jake
Yeah. Well, look, we, as guys, we love playbooks and like, tactics and strategies. Like, break this down for me into logical steps in a script. Here's the script. It's so simple. All you have to do is just ask, what version of me would you like right now? You want me to listen or you want me to give advice?
Michael Chernow
Ask that question.
Jake
Ask that question. They will always tell you the answer every time. It's like shockingly simple.
Michael Chernow
I. You know what's so interesting? I'd be very curious to know what it's like in a homosexual relationship if that is the same thing. Right.
Jake
I don't think it's a. I don't think it's a man woman thing. I think it's a. I personally believe, and I've. I've come to also believe this and this could still evolve. So right now is what I believe is masculine and feminine. It's an energy thing. We all have both. Some days you have more masculine energy than others. Some days you have more feminine energy than others. Some people have a pretty decent 50, 50 split. Some are like 98% masculine, 2% feminine, vice versa. I know tons of women that are extraordinarily masculine almost all the time, and lots of men who are very, very feminine all the time. We have societally assigned stigmas to each of those words. I know a woman who said to me when. She's like, my husband, he's very masculine. He loves power tools, loves cars. He's always fixing stuff. This guy is also a stay at home dad, hasn't worked in like 15 years and hasn't brought in a dollar in a long time. And for the family and is very emotionally reactive and charged.
Michael Chernow
Okay, same guy who loves power tools, loves cars.
Jake
Same guy fixing. Yeah, that's a very feminine guy, but he likes cars and power tools, like, I believe. Is he a bad dude?
Michael Chernow
Not at all.
Jake
Now, she is the opposite. Like, she doesn't like cars, power tools. She loves sundresses and gardening and all that stuff. Flowers. Very soft, feminine, right? No, that's just shit she's into. She is the breadwinner. She works a lot of hours. She's always making the plan. She's like guiding the ship. That works for them. That's a beautiful relationship. They're happy as hell. So I say this at work all the time. I say this with homies, younger brothers, my parents, my girlfriend, everybody. I'm just like, what? What version of me do you need right now? And I think that's just like, for anybody, a kind empathetic question of just like, I can be, I can listen and just shut the fuck up.
Michael Chernow
I think it's such great advice.
Jake
Yeah, I can. We can solve this right now.
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Michael Chernow
We just have no control over it.
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Michael Chernow
Just even sitting here talking about this, right? Like, because there's such a default setting for most people when it. When they hear the word masculine or they hear the word feminine. The default setting, in my opinion for masculine is typically strength. Right? Strong. Masculine. Strong. That's what I kind of go to. Right? And that's not like a. I feel like that's not like, like my opinion. That's just like how we were conditioned. You know what I mean? Like, you're masculine. That's a really masculine dude. Like, you're like, oh, that guy must be like a strapping, strong guy that's like, you know, out there, like crushing stuff. And then feminine is just like soft, pretty, eloquent. Like, like, just. That's where my brain goes. I go, I think feminine and I think female. I think, I think female. I think, I think like, like flowy, you know, like less rigid. I think masculine. I think strong rigid, like unbreakable kind of thing. Right?
Jake
Yeah.
Michael Chernow
And so I just would be curious because we have this conditioning.
Jake
Yeah.
Michael Chernow
Is masculinity the wrong term for what we're trying to describe here?
Jake
Totally. I love that you bring this up. It's why I refer to the optimist as this is a show about men's mental health and modern masculinity. I think it needs to evolve that I was conditioned the same way and unfortunately, I think it needs to change. I didn't always think that and now I do. Is there a better word for it?
Michael Chernow
Because I think when you say even when you add modern to it, there is always, like, why does it have to be modern? Right. Like, yeah, you know what I mean? Like, we were talking about chivalry yesterday, right? Like, chivalry will never be like modern chivalry. Chivalry. Chivalry is essentially having a set of values that prioritizes respect, specifically coming from a man to a woman.
Jake
Sure.
Michael Chernow
Right. Like, that is kind of like, I, I don't know the exact definition of chivalry, but, like. And so I don't think, like, you either like it or you don't. You know what I mean? Yeah. Masculinity in today's conversations has truly taken a new form.
Jake
Right. Currently in the beginning stages of taking a radically new form. Right. And we have no clue what that looks like. Also, it's very dangerous to talk about it.
Michael Chernow
Yeah. But guess what? Like, if you don't have the balls to talk about it, that's. That's your problem. And if you don't want to hear about it and you want to pass judgment because guys like you and I are talking about it, like, that's on you. It's on you. You know? And if you want to judge someone like you or I who have nothing but, like, the absolute best intentions of trying to just, like, unearth something that could resonate with people, I think also we are, you know, the, The. The amount of times that I've heard, like, yeah, men today are just softer. It's just a softer breed of. Of male. Right. Like, it's just soft. And I don't know where that came from. I don't know. I don't know if that really started because men as, as the kind of like, me too movements and things like that started to arise in service. Men sort of recoiled because they were just afraid of getting called out for saying what they actually felt about it. Right. Like, how many guys do I know that would be.
Jake
That.
Michael Chernow
That would say something and be like, oh, my God, I get crucified if I, if anybody heard me say this, you know, and it's like, Cancel culture has made sharing truths really, really hard because there are an enormous amount of people that thrive on drama. And that's my opinion. Like, it's like you can perceive anything in a controversial way. You can hear anything and try to flip it to make it sound like that person is not who they are.
Jake
Yeah.
Michael Chernow
Right. And so everybody has to tiptoe.
Jake
You.
Michael Chernow
You've. You have no choice but to tiptoe. Like, what do we do about that?
Jake
Yeah.
Michael Chernow
And it, and I will, I will, I will say this and, and, and maybe I do get crucified for saying this. But like it's predominantly men that have to tiptoe. It's predominantly men that have to tiptoe. Would you agree with that?
Jake
Yes. I think it's important to try our best to break down how we ended up here. To start.
Michael Chernow
Let's do that.
Jake
I have a take. I'm going to do my best to break it apart. I'm going to ask that no one clip a half baked segment of this because it could without context. And I've had lots of clips go out about myself without context. So. And normally it's fine, but for something like this, this is important that it doesn't. What I've gathered, I think is this, what I've gathered that I think the story is is something along the lines of somewhere around the mid to late 1900s, and I love this, women entered the workplace more women got their own credit cards and got their own mortgages. Women became, started the journey of becoming equal members of society. I love that my mother was one of those women. My sister is as well, big time. And somewhere along the way I think a lot of men got very threatened by that. It began. One of the many, many conversations that we've seen come out of that is the question of like, could you, hey dude, could you marry a woman who makes more money than you? Like, was any guy ever asked that in 1964? Like, probably not, but like then some wrong way that became a question and of men had a hard time with that, I think due to ego in some ways how they're biologically wired. It was scary for them. It's nothing they've ever seen before. It was not what they grew up in, in their household. So, so that question became an uncomfortable new reality.
Michael Chernow
And, and this is just a fact. Let's, let's.
Jake
Yeah. This is just like how in the United States over the last hundred or so years, like how things have played out last like 50 years then. This is my version of the story. A show called Sex and the City came out in the 90s. And this show, I think it's a great show. I love Sex and the City. Learned a lot about women by watching Sex and the City. Sex and the City for anyone who doesn't know, is about four women who are all very different from each other, who are best friends, who live in New York city in the 90s. And they are, they have a lot of sex and there's all every Episode, there's a different guy essentially who's in the picture and they're just figuring it out. And I think that show was important for the zeitgeist because was the storyline of basically for the first time ever in all of human history, for what, hundreds of thousands of years, all of a sudden a woman can go live by herself, buy her own things with the money that she makes on her own and can go sleep with as many guys as she wants and like be free and do this thing. Something that men have been able to experience for a lot longer. And so grandma never had that. Mom sort of had that a little bit, but she still got married at 24 years old. So grandma and mom told daughter, you need, you need to lean into this. You need to go have your sex in the city years. Because I barely had it and grandma never had it. Like you need to have that. And I'm 30. These are all the women in my peer group for the most part. And I'm from the Northeast. Women from the south have noticed or the Midwest a little bit less, just based off of cultural values. But that is a storyline that I have seen take place. So then they go to college and then birth control is a thing, so now they can sleep around safely. All incredible advances in our society, which again, I'm very for and I love it. And then the me too movement happens and social media is a thing. And so all of a sudden we saw a lot of vengefulness and revenge, feelings of vengefulness and revenge taking place in society where for the first time it's like men, especially white men, have had a grade for all of human history. Now is their time. Now is the time for them to shut the fuck up and sit down and like, let someone else have their moment. And that got pretty extreme because it also meant we need to tear those men down and tear those men down. A lot of awful guys who have done awful things got into a lot of trouble in that time. Good monsters, glad that they got what they deserved. I'm glad that we shined a spotlight on really shitty behaviors and I'm glad that that still happens. But because of that, now you've got a lot of very innocent everyday guys terrified, terrified to ask a question, to pay for a woman's meal, to hold a door for her, to ask her on a date, to kiss her at a bar. And now we're in the mid 2000s. And then you've got more women now going to college and graduating from college than men. You have more women Getting jobs now than men. And why? Well, I just think the pendulum swung really intensely in that direction. Again, I'll keep saying it. Awesome, awesome, awesome. This is happening with the women, the men. A lot of these men chose to recoil and stay silent and live in fear. And I think now we're starting to swing back from that. This podcast exists for that reason because we should be talking about this stuff. It's not about tearing men down. It's about equipping them with a new understanding of what does it mean to be a man? What does it mean to provide and protect and be masculine? And here's, I think the, the wildest piece that shocked me. So I put this show out there about a year ago and over the probably first like three to six months of, of it being out there, I was met with, I mean, tens of thousands, tens of thousands of dms and comments from women. Wasn't expecting that at all. And the vast majority, almost all, were somewhere in agreement of like, oh, thank God, like, I, I've been looking for a man. I don't want to date women. I don't want to date a woman. And for some reason these men are acting like women. I have women, I have my friends, I have my mom, I have my sister. Like, those are my women. I don't want to sleep with them. I don't want to marry them. I want to marry a fucking man. Where are the men? Thank God that now there is a community forming or podcast starting, whatever that like, can help men become men. But there are some new guidelines and rules that we do have to follow to be a good man nowadays. What are those rules and guidelines? Like, no one knows. That's where we are. That's how we ended up here. But the women want this. The women want to be approached in public. They don't want to go. They don't want to approach you in public. They don't want to. They want to be asked out on a date. They want to be picked up in your car. They want you to walk to their door and knock on the door and pick her up with a flat, with a bouquet of flowers. Like, they want that. And a lot of guys think they don't want that. Some women don't, but the vast majority, they do.
Michael Chernow
Why do you think some guys think they don't want that?
Jake
Because some very loud woman at some point told them, if you do this, you're wrong and I'm gonna make sure that your life is ruined.
Michael Chernow
Why do you think that woman felt that way?
Jake
She probably that was Me Too movement. That was that era. And I think she probably had some very nasty experiences with men herself, unfortunately. And I feel a lot of compassion and empathy for her. And quite frankly, I don't blame her for, like, hopping on the bandwagon of MeToo movement and. And just. And speaking up. Good for her for speaking up and, like, saying she's pissed. It definitely sent a loud message, and we. We heard the message, but now, you know, okay, let's hear the message, and let's just stop being so scared, though. Let's have a conversation about it.
Michael Chernow
Why do you think holding the door for a woman today could potentially be viewed as chauvinistic as opposed to chivalry?
Jake
I really struggle to understand how that chauvinistic, candidly.
Michael Chernow
But it. But it.
Jake
But it is. In some ways, some people believe it is.
Michael Chernow
Why do you, like, where would that come from?
Jake
I think we discussed this yesterday a little bit of the conversation of power. Just a. I think it just naturally fits into the category of what my creepy uncle used to do. Like, according to a female. Right? Like, Anything a traditional man would do to, like, court and treat a woman, whether it's in the category of chivalry and it's actually quite respectful, or it's in the category of, like, super disrespectful and way over the line. It just all got bucketed into one assumption, into one massive bucket and was like, that's. That is outdated. It is chauvinistic. It's not modern, and I don't want it. I don't be treated differently. I don't want. I. I can open the door for myself. Don't think I'm strong enough to open a door. I've heard that before. Directed, direct. Directed towards me at times. I remember one time I was playing darts at a. A party in Brooklyn a couple years back.
Michael Chernow
Sounds pretty masculine.
Jake
Playing darts. Me and two. Two women just, like, shooting darts in the backyard. And he was at a party, and I'm not that good at darts. Just not. But, like, I can hit the dartboard. One of the gals that I was playing with sucked at darts. Missed the board by, like, six feet every time. And I was just like, hey, do you want me to, like, can I show you how to hit the dartboard? And she turned to me, she threw the darts on the ground. Was like, I don't need you as a man to describe how to throw a dart at the dartboard. And I was just like, okay. Like, I'm thinking, this has nothing to do with the fact that you're a woman and everything to do with the fact that you just suck at darts. It's that simple. I didn't say anything. I was just like. And I just walked away. And you know what? Like, how am I going to respond to that? At a party in public in Williamsburg? So that. That, to me, is the vengeful feminist.
Michael Chernow
Do you think any of this really exists without the fuel of social media?
Jake
It's a good question.
Michael Chernow
Yeah.
Jake
In historically, like, if we didn't have social media, would we still have ended up here?
Michael Chernow
Yeah.
Jake
Oh, I don't know.
Michael Chernow
The beginning of this. The beginning of this, in my opinion, was Monica Lewinsky.
Jake
Okay, sure was the beginning because it
Michael Chernow
was pre social media and it made massive headlines. Yeah. The most powerful man in the country. Right. That was, in my opinion, when this conversation began to truly take shape. And. The sad part about it is that the Bill Clinton, Monica Lewinsky debacle was one of millions of situations like that. Right. The big powerful boss sleeping with the
Jake
secretary
Michael Chernow
happened forever and ever.
Jake
Yeah. Not a new story.
Michael Chernow
Not a new story, but because it was the most powerful man in the country, maybe the world, it made headlines. Right. And I. It really it up for us because not every guy in a position of leadership. Let's not even use power, because now leadership and power get completely. Because there are these guys, right? There are these guys that like. Like, I. And I don't care you guys can bash me for this or not, but Donald Trump is the perfect poster child of the power leader collab mashup that sends chills down the spines of lots and lots and lots of people, both male and female. Right. Guy walked into the room and the whole. The energy just changes, you know that kind of guy. I know that kind of guy. Donald Trump is the ringleader of that. Right. Do I think it's good for some things I do. Like when you're like, you know, when. When somebody's threatening to. To, you know, annihilate a country with a. With a massive bomb. Like, you want a guy like that to be like, whoa, whoa, whoa. Let's talk about this. Right? Like, you want everybody to be on their toes when a guy. But in general, that guy is, like, not loved by many, many people. Right. That guy is feared by many, many people, specifically if you work for him. And the sad part about it all is that I'm a leader. You're a leader. You own a company, you've got employees. You're not a vengeful like. Like, you know, angle Seeking creep. But unfortunately, you have to be very, very, very careful about what you say and how you say it, because you could very easily be categorized in that bucket.
Jake
Yeah.
Michael Chernow
And that is, I think, the problem that. That, that. That all of this has created. Right. And that is why I think it is. Masculinity was never a bad thing when I was a kid.
Sponsor/Ad Voice
Like, it was like, you heard the
Michael Chernow
word masculinity and you were never like, oh, that's toxic. Never. Yeah, it just wasn't like. It was not a bad word.
Jake
Right.
Michael Chernow
It just wasn't a bad word. You know, and it was clear what it was, and so it's very interesting. But, you know, I'm not a female, and you're not a female. And I remember when Black Lives Matter happened, right. And I was the CEO of a restaurant group, and I had 350 employees, and 50 or more of them were ethnic. Not from, you know, either. Not from the United States of America or African American or whatever. Right. Like, we were like, you know, we were. We were like the United Colors of Benetton at Seymour's, a meatball shop. It was like a little bit of everything, and it was wonderful, and it was incredible, and we loved each other, and it was just an amazing business.
Jake
Yeah.
Michael Chernow
And I was also young. I was 33 or 34, and nothing like that had really ever happened in the world with me being in a leadership position. Like, I was leading 350 people, and I didn't know what to do because the ones that. The people that were speaking out about it were either getting praise or absolute pushback and getting put on blast. And. And. And the ones that weren't saying anything were all getting. It was. It was. It was. It was basically all pushback. Like, your silence is worse than your. You know. And so I was put in a position for the first time in my career being a leader to have to figure out what I was going to do here. And I just did not know what to do. And so I am a product of New York City public schools. I grew up in New York City. I went to public school. There were thousands of kids that I went to school with. And I personally, as a white kid in New York City going to public school, like, I just never thought of black, white, Puerto Rican, Indian, Asian. Like, it just.
Sponsor/Ad Voice
It was like, you're.
Michael Chernow
You're. You're my boy. It's like that was never like a friction point. Ever. Yeah, never once was it ever like a friction point. Right. I got into fights with white kids, black Kids, Puerto Rican kids. I went and hung, and my best friends were white kids, black kids, and Puerto. Like, it just was my. You know, like. And so my thought was, you know what? I'm just going to say that I grew up in New York City. I don't think about color. I don't see. I don't even see it. It doesn't register for me as, like, a distinguishing element. Yeah. You know, when I consider somebody's character who they are. And I got slammed, slammed hard. And the reason why I got slammed was because. And not necessarily from my employees, although some, but really from the masses. You're not black. You, as a white person might not have seen color, but me as a black person saw color. And I was like, damn, I tried to do the right thing. And I just didn't think far enough down the road of, like, how this could affect someone who was a person of color when I said it. And so when we talk about this masculinity thing and we talk about, like, the. The females that, like, you and I, as men, could women see it differently? I would imagine. Right. Because it is a topic about men, but it's coming from the female audience. The Black Lives Matters was a topic about racism, coming from black and African. African Americans. Right. Like, and so we're. We're caught in these positions in these places where, like, how do we. How can we communicate about this without people with people with people truly seeing, like, the good intentions of wanting to be able to work through it and communicate properly and not offend? Like, how can we talk about these things without offending?
Jake
Yeah.
Michael Chernow
If you don't have the intentions of offending. You know what I mean? Like, it's.
Sponsor/Ad Voice
It's a very hard place to be.
Michael Chernow
Yeah, right. Like, it's a hard place to be because your intention is not to hurt someone's feelings or to make somebody feel inadequate in any way, shape or form, but, like, the. The tiptoeing is, I think, where it makes it really, really difficult to move forward, you know, because most of the people. And I will say, by the way, like, there are definitely terrible people. Like, we've called out. Like, you were. You were a piece of shit scumbag that.
Jake
That.
Michael Chernow
That did the things that the MeToo movement called out and highlighted. You deserve every single second of pain and suffering that you. That you got every second of it. And I know plenty of men that. That got it and deserved it. Hundred percent. Like, 100%. But the, the. The umbrella that opened that most of us got kind of like put under as anybody in a leadership position, specifically leadership position, the fire is on your ass at all times.
Jake
You know, I think it's a good thing that MeToo movement happened. Black Lives Matter happened, and that scared the out of us. I think that's a good thing because. Take Monica Lewinsky, Bill Clinton, he cheated on his wife with his secretary. That was wrong 100% shouldn't have done that. And for a very, very long time, people were getting away with things that they themselves Knew was wrong 100%. And I think that now we're in an era of walking around in our daily lives as anybody person or as a leader or a parent or on social media where you have to think twice before you do something or say something. You may have a natural human thought to, like, want to do something that's not cool or say something that's not cool. Because every single fucking human being gets that. Intrusive thoughts, as some people call it. People used to just act on that stuff, and there was no consequence. Now there's a. There are consequences. Good.
Michael Chernow
Yeah, I agree.
Jake
Like, keeps us in line. And I think I'm glad that we're in a moment. Hopefully this lasts of like, take a sec, people, and think about, before I do this thing or say this thing, is this the right thing to do or say? And if it's not, don't do it. Because if you do or you say it, you're gonna get flamed. Your life is done. It's a lot to lose. I think that's good. But it is still important, I think, to look the way I. I at least try and, like, I don't know if I'm great at it or perfect at it, but the way at least I go into these things, these tough conversations or show up in a room or whatever is. I just go play the card of radical transparency and honesty around where I'm at. So that might look like. Before I have this conversation, whatever I'm. I don't. I'm nervous to have this conversation.
Michael Chernow
You are?
Jake
Or just like, I would say that out loud.
Sponsor/Ad Voice
Oh, yeah, me too.
Jake
Like, I'm nervous. I don't know what. I don't want to say the wrong thing.
Michael Chernow
100.
Jake
I don't want to offend. I don't want to hurt anybody. But it's worse to stay silent. Can we. Can we just be adults here and, like, try to have the uncomfortable conversation and almost like you just are releasing liability.
Michael Chernow
But guess what? So that's what you and I are doing here, and we're actually. We're actually courageously having this conversation because guess what? I too, am nervous. Yeah, I too am nervous. Right? Like, I'm not joking. Multiple times throughout this conversation, the thought came through my mind, am I going to release this podcast?
Jake
Sure.
Michael Chernow
Right.
Jake
Me too.
Michael Chernow
And, and, and, and, and what? What? I'm. What I think I have. I want to be able to talk about these things. I just shared about my sexual molestation journey as a kid on a large platform. And I feel like, why can't I be the person willing to take the pushback? Willing to. But. But also willing to have the courage to have the conversations. Yeah. Because I'm here to say. I'm not racist, I'm not chauvinistic. I'm actually, I, like, love everyone. That is just the truth. And people could be like, can hear that right now, listening to this podcast and be like, this fucking guy doesn't know what the fuck he's talking about. This guy is privileged white. Whatever. It's just the truth, man. I'm telling the truth.
Jake
Yeah.
Sponsor/Ad Voice
I've got.
Michael Chernow
I don't judge based on. I judge people based on the actions that they take in life. Right. How they, how they conduct themselves, not what they look like, not the sex that they are, not what the decisions that they choose to make with their sexuality. None of that.
Sponsor/Ad Voice
I could care less. I could care less. I support all of you,
Michael Chernow
but I do think it's important that we have these conversations because so much, so many
Sponsor/Ad Voice
of us are so scared to have
Michael Chernow
the conversations that need to be had in order to make progress.
Jake
Yes. The way I think of it, and I don't know, this is just how I look at things these days, is I'm going to show up and be very vulnerably raw and real about what I'm experiencing in that moment. It might be like, I don't know how to have this conversation, or I'm really nervous to ask the following questions, but I think it's important. Whatever. Like, just be totally real and put it on the table of what. Where you're at. Then go slow, take your time. Like, really think thoughtfully about what you're about, what you're thinking, and then say it very slowly and be very careful and maybe even say things like dancing around my words here. Whatever. Like, just take. Put some care into this shit and act and speak in a way that I genuinely can a thousand, thousand percent look in the mirror after and say, I handled that the best I could with as much integrity as I really think I can. Like, genuinely do your absolute best and your most integrity, and then my job is done. That's it. How someone else wants to react to that, that's not on me anymore.
Michael Chernow
I'm going to finish with this last question because I think it's an important one. And. And have you had a woman on the podcast?
Jake
Oh, yeah, Many.
Michael Chernow
Okay, what is. I've got to listen to a few of those because I think that that's really. I would love to.
Jake
I would.
Michael Chernow
I really want to know. And this is my bad. I have not asked enough women this question. What is masculinity mean to you? Is there a difference between what masculinity meant when you were a teenager, what masculine masculinity means to you now as an adult? I will. I want to know. I want to know.
Jake
That question I've asked every single guest on my pod. What do you think it means to be a man nowadays? That's the closing question. Even if the episode had nothing to do with men. And I mean, I had an episode once with a woman about. About detoxing and cancer. I was like, look, we didn't get into this at all, but what do you think it means to be a man nowadays? So everyone is asked that question, and the women have shared some amazing answers. Everyone shared great answers. The women have especially shared phenomenal answers. And it's typically to the tune of a man nowadays. Just kind of two things. Number one, fucking does what he says he's going to do. Says what he. Do what you say. Say what you do. Like, does what he says he's gonna do is a man of his word. Like, and. And the stories that I hear from that, from friends, from podcast guests who are women, etc, like, it blows my mind how often men. How many men are not men of their word in any way you can imagine. Yeah, I'll pick up milk on the way home. And you fucking didn't. Doesn't matter. What happened? It doesn't matter. You said you were gonna pick up milk and you didn't get the milk. I don't care if it's because a fucking swarm of bees attacked you in the car on the way home and you crashed. Like, you just. There's just no excuse. You just didn't do the thing. You said you were gonna do that too. Like, I'll never cheat on you. I'll never leave you. I'll never hurt you. And then you fucking did. Maybe it was 11 years later you.
Michael Chernow
You did.
Jake
So, yeah, women have a really hard time trusting us. And the Next answer I get is something to the tune of a man nowadays knows how to be in his masculine and in his feminine and doesn't have a problem with that, can be man enough to do feminine or say the feminine thing or have a feminine feeling and express it like that to them is the sexiest, most attractive, most manly thing you can do. That was pretty shocking to me as I started to hear that a lot. And I agree with it. To look a woman in the eye or another man in the eye as a man and say, I'm sad. Sad.
Michael Chernow
I think we gotta finish there, man. I mean, wow, what a, what a
Jake
strong
Michael Chernow
nerve wracking, but like courageous conversation. Yeah, right. Like I, like there are going to be people that listen to this and probably hate me and then there are going to people that listen to this and commend the two of us for like having the courage to have this conversation.
Jake
Because do you feel that was in pure integrity and like you handled that
Michael Chernow
as best as you could, A hundred percent.
Jake
And however someone's going to react, that's,
Michael Chernow
that's, it's out of my control.
Jake
We're never gonna, never gonna please everybody. And I think that's a huge problem is it's so simple with content these days. And I, you know, I make podcasts, so I'm always thinking about content. Everyone's afraid of that. So. And then the word AI slope, like that's a whole thing. It's the same shit which is just like nothing has an edge or an opinion or a controversy or any provocation anymore. It's just vanilla. Everything is like meant to please everybody. Therefore there's nothing interesting about it at all. There's nothing interesting about it all. You know, it's like the best part of journalism ever is op eds, opinionated editorial, opinionated editorial. Like that's fucking good content. But no one does that anymore. I think it's important to have an opinion.
Michael Chernow
Where can people follow along your journey? The optimist, your business?
Jake
So Instagram, it's Theoptimist podcast. My company is called Thursday Labs. We produce podcasts for startup founders and venture capitalists. And then the Optimist is the show I host. So my, my Instagram handle is at Jakefrom Thursday, kind of like Jake from State Farm. And I post a lot about the show, but also the journey of making a lot of podcasts and my budding endurance sports career, which is always going to be an amateur career.
Michael Chernow
Dude, this is great. Yeah, man, this is great.
Jake
Important stuff.
Michael Chernow
I, I knew I wanted a Today's been a bit of a string of pods, and I wanted to finish with something that was going to just kind of, like, fire me up. And this one definitely did, because whenever I'm scared, but I use courage to kind of push through, I feel like we end up with strong outcome. Yeah. When courage is a part of it,
Jake
you know, Appreciate you just doing this, man. Seriously, it's. You know, I. Of the episodes I've done probably half, maybe a little bit more, like, go there, you know, like, say the thing that people are thinking and are afraid to say and just, like, have an original, like, real, authentic point of view.
Michael Chernow
Ladies and gents, that one was real, and I'm really happy we had it because I feel that I'm at a place in my life where I want to be able to have these real conversations, and I want to be able to look fear in the face and say, hey, you know what? Like, there's. There's a lot of people. And not just this conversation that we had. There's so many topics that are. That people, you know, the amount of people that I know that, like, secretly voted for Donald Trump in this past election. Right. Like, let's have these conversations. Let's have them and really do our best to, like Jake said, when you're having them, slow everything down and don't let a, like, guttural reaction to something that somebody says inspire you to say something that. That you potentially didn't think through, even if it was for 30 seconds, whether it's on a platform like this or just a conversation with friends and family. Like, give yourself that grace to just pause for a minute and just think through what it is you want to say before you say it. And maybe there are going to be people that are going to receive it the wrong way and they're going to flip it and they're going to contort it and they're going to, you know,
Sponsor/Ad Voice
clip it without the context.
Michael Chernow
Like, Jake had, you know, asked us to make sure that we did on that one thing that he had mentioned about, like, the Sex and the City theory. But I am grateful to have the ability to have these conversations, even though I am telling you right now, as I say this, I am scared. I'm scared and I'm nervous, and that's just a fact. But I'm doing it anyway because I do think that we need to massage this sore muscle. We just do. We need to figure out a way to loosen it up a little bit. And I'm not some famous celebrity that could potentially you know, nobody's, you know, clipping this a thousand times in tmzing this so I can have these conversations and hope that the community knows that it's all for the bet. It's all with the best of intentions. It's all with the best of intentions. And I probably didn't say everything the right way throughout the conversation. I'm sure when I go back and listen there, I'm gonna, I'm gonna, I'm gonna say, damn, man, like, I could have spent more time before I said that. But I, I, I am grateful for you guys listening.
Jake
Can I add a small piece to that?
Michael Chernow
Yeah.
Jake
I think best thing we can be doing at large is just, just be curious, lead with curiosity. Go sit with your friend who looks very different from you or someone you have never spoken to or whatever. And if it comes up, just be like, what's that like for you? How does that feel? How can I support you in that? How? This? Why that? What, like the who will, when, where? Why? Just like ask questions and, and be interested to learn, interested to grow, interested to evolve your own opinions. Scary. It's, it's weird, it's new. But I think that that's the, I just think that's the recipe is just like, just be curious and open.
Michael Chernow
I mean, I, I think that what you just said is really like, the thought that went to my, through my mind is like, when we think of a masculine man, we don't think of a curious man necessarily. Right?
Jake
That sucks.
Michael Chernow
Yeah. Yeah.
Jake
This is part of the exploration of what is a modern masculine mean? It's right. Be curious.
Michael Chernow
Yeah, I think that's a good, a good way to sum it up. So share this podcast if you feel inclined. Give us a five star rating and a review if you're feeling super generous. And I'm so grateful for you guys for tuning into the pod, subscribing to the pod, being part of the community. We talk about a lot of stuff here and you know, we, we certainly talk a lot about habits, rituals and routines. We also talk about masculinity and, and spirituality and, and you know, every once in a while we, well, we'll touch on, I don't know, psychedelics or something. But, but we've, we've evolved the podcast to be a little bit broader in terms of the topic of conversation. And this isn't the first conversation on the podcast that we've had about masculinity. I've had it a few times now and so far it's been received well. And I hope you guys received this one well. And just know that if there's something that irks you, there's something that bothers you, that we struck a chord in some way that was not positive for you. Shoot me a dm. Shoot me a DM At Michael Chow. Like, I'm happy to talk. Be curious. Shoot me a DM. Anyways, I appreciate you guys. I love you guys. And until the next one, y', all, peace.
Podcast: Kreatures Of Habit Podcast
Host: Michael Chernow
Guest: Jake Hurwitz (Host of The Optimist Podcast, entrepreneur and podcast producer)
Date: March 25, 2026
Theme: A raw, vulnerable conversation exploring how masculinity is evolving in modern society, the challenges men face in expressing vulnerability and emotional strength, and frameworks for becoming a ‘better man’ in a changing world.
Michael Chernow welcomes Jake Hurwitz to unpack the notion of modern masculinity, how men can be both providers and protectors in new ways, and why emotional honesty is essential. They dive deep into personal stories, shifting social landscapes, and actionable advice for navigating today’s complexities around gender roles, vulnerability, and integrity—all while both men openly wrestle with the fear of saying the “wrong” thing in a culture of judgment.
Jake’s Story of Suppressed Emotion (00:00–05:19)
Growth Through his 20s
Traditional vs. Modern Meanings (09:36–10:44)
Holding Space vs. Fixing Things (10:47–14:19)
Cancel Culture’s Impact
Radical Transparency & Courage
| Timestamp | Speaker | Quote/Insight | |---|---|---| | 00:00 | Jake | “All I really wanted to do, as fucking lame as it sounds, was go home and, like, cry. But, dude, in what fucking world can you say that to your boys?” | | 09:43 | Jake | “To provide and protect...now there's a whole category...that is emotional. How do you provide emotional safety?” | | 10:47 | Jake | “Hold space means to shut the fuck up and just listen...just be there and listen.” | | 15:53 | Jake | “All you have to do is just ask, what version of me would you like right now? You want me to listen or you want me to give advice?” | | 23:54 | Michael | “Cancel culture has made sharing truths really, really hard because there are an enormous amount of people that thrive on drama.” | | 31:25 | Jake | “It’s not about tearing men down. It’s about equipping them with a new understanding of what does it mean to be a man?” | | 49:23 | Jake | “I think it's a good thing that MeToo movement happened...that scared the shit out of us...Now there's a consequence. Good.” | | 52:52 | Jake | “Just be totally real and put it on the table...do your absolute best and your most integrity, and then my job is done. That's it.” | | 54:57 | Jake | “Women have especially shared phenomenal answers...A man nowadays does what he says he's going to do...and also knows how to be in his feminine and masculine, and isn't afraid of that.” | | 64:11 | Jake | “Just be curious, lead with curiosity...ask questions, be interested to grow, evolve your own opinions...That’s the recipe.” |
For men struggling to communicate emotionally:
When discussing difficult topics:
For societal progress:
Follow Jake Hurwitz:
Follow Michael Chernow & Kreatures Of Habit:
For listeners seeking a nuanced, brave, and real take on what it means to be “a man” in 2026, this episode reframes tradition, embraces emotion, and models how to courageously open conversations that matter.