Pivot - Ask Kara and Scott!

Episode Date: May 31, 2022

You send us great questions, and we owe you answers. On this episode, we open up the listener mailbag, fielding queries such as: What's the best way to change jobs? How does Kara prepare for her interviews? Why isn't Scott on Shark Tank? Plus, the dating advice you didn't know you needed...and more! Submit your Listener Mail questions for a future episode by calling us at 855-51-PIVOT, or via Yappa, at nymag.com/pivot. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Just go to Indeed.com slash podcast right now and say you heard about Indeed on this podcast. Indeed.com slash podcast. Terms and conditions apply. Need to hire? You need Indeed. Hi, everyone. This is Pivot from New York Magazine and the Vox Media Podcast Network. I'm Kara Swisher.

And I'm Scott Galloway. And today, because we're away for the holiday weekend, we're cracking open our listener mailbag. You've got, you've got, I can't believe I'm going to be a mailman. You've got mail. We've gotten a lot of great questions, and today we're going to dig in and answer some of them

because we love our listeners, don't we, Scott? Do we love our listeners? Yeah, no, I love everything about this except for the people. But no, our listeners? Yeah, anyways. Come on. We love our fans. We love our fans. Yeah, thank you. Okay, good. Okay, Scott, let's kick it off with a question that came in via voicemail. Roll the tape. Hey, Scott. Hey, Kara. I'm looking for some advice. I have a pretty safe job. It's in finance at a rating agency. We've been in, you know, 12-year bull market.

Things are looking a little bit shaky. I have an opportunity to go into an investment banking role. Curious your thoughts with the economy dipping. You know, is this the best time to move? Doesn't matter whether I'm in the rating agency or in the investment bank. I think I could learn more in the investment bank. I think I could learn more in the investment bank and get more out of that position, but also don't want to lose my job six months into it. Let me know your thoughts. Love to hear them. Love the pod. Thank you guys.

I always say go for it. I don't know. He sounds young. Why not? What do you think? I mean, you've shifted a lot of jobs. I constantly am leaving jobs. So I always say, go for it. If you don't like what you're doing, you feel it risky, you could learn something else, go for it. Most of my job moves haven't been a function of choice. I only got fired once. No, I get a lot of these questions. And let me be clear. First off, a lot of it is situational. And what you need is some individuals who, you need a kitchen cabinet of people who you can provide more color to. For example, what are your opportunities, your current opportunity set?

Do you have senior level sponsorship? Are you making good money? Have they recently promoted you? Are you on the cusp of a promotion? Are there family reasons or flexibility that this company provides you. Now, having said that, in general, in general, the way you escalate your compensation faster than the market requires you leaving your job because we have a tendency to see people through the lens through which they were hired and we romanticize strangers. So typically, you end up in a situation where it's hard to maintain

velocity of compensation growth unless you move every three or five or seven years. Now, having said that, what I would do is the following. You need a kitchen cabinet to describe in greater color the situation and get good sober advice. Two, if you in fact decide that you can leave and it's a good option, go into the manager that you work with and don't be threatening, be transparent. I am thinking about taking another job. This is why I am thinking of taking it. And hear what they have to say. Because typically in relationships, whether it's romantic or whether it's professional, you have a tendency to not appreciate the person's full worth until

there is a credible threat they are going to leave. Which sucks. It does suck, and it's true. I hate it. And what you might find is that once they realize there's a credible threat you're going to leave, that they offer you everything you're going to get at the next place and maybe more. Having said that, my general view- And then they're resentful for you doing that, but just go ahead.

That's right. That's right. Yeah. But my general view here is that you need a group of people that can understand the color and the nuance and give you great advice. Two, the reality is it is hard to escalate compensation fast in the market without at least checking the market or leaving. At NYU, I started at $12,000 a year. That was my compensation my first year at NYU. By the time I left, I was making— $12,001. $12,005. $12,000 a year. That was my compensation my first year at NYU. By the time I left, I was making—

$12,001. $12,005. $12,500. I was making over $200,000 a year with all kinds of crazy fucking benefits. Now, was it because they liked me? A little bit. It was because I was good. I put butts in seats.

And every three to five years, I would take a call from Wharton or Cornell, and I would find out what my market value was. And then I'd walk into the dean's office, and I'd say, just FYI, this is what they're offering me. And I was transparent. I don't want to leave, but this is my market value. And then they'd hum and ha and go, okay, give him what he needs. Because organizations, the majority of them, really good organizations, will stay ahead of your compensation curve. And this is advice to managers. I try to imagine every person that works with me is about to leave for Google.

And what are they worth to me? And I try and maintain that compensation. Because the temptation 90% of managers fall into is they seem happy. They seem happy. Oh, give them 8%. I always never do that game with people. I'm like, if I don't want to stay somewhere, I go somewhere else. I just do. I just, if I'm not,

I think you should evaluate whether you're happy in the job. And if you're happy in it, then you do what Scott was saying. If you're not, just move along. I think moving along, and when I was a manager, for the short time I was managing, I always liked when people got jobs. I remember Mike Isaac, who was

going to the New York Times, was working for Recode. And he had really come up at Recode. He was at a, I forget, was it Wire? The back room at Wire, whatever. He did really well. His profile was raised. And he came to me. He was scared to tell me this.

And I was thrilled for him. I was, you'd be thrilled for people that have great new opportunities. This is great. It shows a lot about us and you getting notice. And you need to move on to the next thing. Almost everyone who's worked for me, I'm always like, great. That is great. It shows a lot about us and you getting notice and you need to move on to the next thing. Almost everyone who's worked for me, I'm always like, great, that is great. And so, you know, I think if people, I think it's always good to move on. Oh, I never have regretted any move I've made, any of the many I have made. So I'm going to go out on a limb here. I think you're, I think

you're an exception and I think you're exceptional. You've benefited from platforms, but you've always been sort of a journeywoman, and you have exceptional talent, and I think you have more what I'll call career flexibility than most people. Sure. Because it doesn't matter if it's the New York Times, the Washington Post, Vox, Wondery, you're kind of at a point where you can sort of plug and play and just add water. You are bigger than the platform right now. I think the majority of people, that's probably not true.

But look, what is a no-brainer here? Find some thoughtful, smart. You don't, it is really hard to read the label from inside the bottle. You need a group of people, maybe even some people at work, just lay out everything. This is what's going on with me financially. This is the offer. I don't like this. This is what I like, what I don't like. Yeah.

And you could also use this as leverage to go back to the investment bank and say, he mentioned that he's worried about being fired two years. Say, this is an insecure environment. Can you give me a two-year deal? Most investment banks, if they really want you, will guarantee you a certain deal. That is correct. That way, if in three months they decide to lay off everyone in fixed income, you got your two-year deal. Don't make this decision. Greatness is in the agency of others. Great decisions are in the agency of others. Get some people. Ask for what you want.

Get a kitchen cabinet. And ask for it. Okay. That was great. That was a great question. Good answer, Scott. A little different from both of us, but there you have it. Okay, Scott, this one comes from Aaron B. in Washington, D.C.

It came via email, so let me read it. As the show Shark Tank comes into a year-end season, I wanted to know which shark you trust backing your company. Who's the shark you wouldn't want to get near your startup and And why, lastly, what are your general thoughts on the show? And do you think they should continue the structure they've been doing or is something new they can add to the show? Well, you know, live, I don't know what they can do, live firings. I don't watch the show that much, although I love Mark Cuban. I haven't watched it that much. I think it's fine, the formula. It works. People like it. People want to talk about innovation. I think it

gets people interested in startups. Some of the stuff seems kind of cooked, that stuff I've seen. I get easily bored with it. But I don't know. Scott, do you watch the show? I guess I like Mark Cuban. I don't know. The bald guy, and there's a lady, and I don't know. I have never watched a full episode of Shark Tank. And of course, I'll turn this back to me. I've had two offers to be a shark on Shark Tank ripoffs in the last few months. Really? He didn't tell me this.

Just so you know, he didn't tell me this. But go ahead. I said no both times. I know, but why did you say no? Because I think to be a good angel investor, you've got to be really involved. And I don't have the time or the inclination. And not only that, I'm not a good angel investor. Every small company I hate, I'm like, that'll never work. That'll never work. And so I'm just the wrong guy to be an angel investor. I've made some angel investments, but it's mostly emotional graduates

of Haas who I like or people doing interesting things. And you know what I do with my angel investments? I literally assume I'm going to lose it all. I think of it as consumption, trying to help young entrepreneurs. And I take a little bit of money. But Mark Cuban would be a great investor. But angel investing, I find at that very early stage, I find it, again, I find it a little bit, I don't know. I just, I watch these things. I'm like, I live that. I was that person on the other side trying to figure out a way to get a quarter of a million dollars from someone and scrape it out. And I find it just sort of exhausting. I don't.

You'd be good on that show. You'd have like a horn. I could see. A horn? I don't know. You'd have some sort of prop. I could see you on there dressed in funny clothes with funny glasses. I'd have a drink in front of me. That's true. I'm like, all right. The drunken investor. That's...

What are you guys doing later? Let's have a drink. Hey. I'll drink to that. You have any liquor companies that I can invest in? I'll drink to that. I get pitched by a lot of marijuana-infused... Do you? Every marijuana or THC-infused drink I have been pitched on. Oh, wow. I'm like, what does this say about me?

Wow. Wow. I told you someone gave me mushrooms for a mushroom company the other week. I was like, okay. As an investor, it's a terrible part of the ecosystem unless you enjoy working with young people in small companies. Yeah. So we have no opinions about the show, except we like Mark Cuban. Yeah, don't know anything about it,

except we really like Mark Cuban. What could they add to it? I don't know. Remember that one they tried that wasn't Mark Cuban, where they had an escalator? People rode the escalator down. It didn't work. It was on Apple TV.

Do you remember they had one like that? Wasn't that called The Apprentice, where they're in the elevator? No, I liked The Apprentice. That elevator was The Apprentice. I got to tell you, I liked The Apprentice. I thought it was a great format for the time. And then it got tired. And it was all performative, the whole bit of it. But I

enjoyed The Apprentice. I liked when they got in the car. I liked when they tried to create a hot dog stand and who had the better hot dogs. I hate Donald Trump, but I love The Apprentice. Go ahead. Here's the problem or what I find depressing about angel investing. It's a bunch of young, wonderful people trying to make their way. And they get an investment from you and they overestimate your capabilities. They think if they call you, you're going to give them amazing advice and all they need to do is listen to you. Yeah. And most of the time when they call me, I'm like, shit, I don't know. Yeah, that sounds, that's a tough one. You got any cannabis-abused tequila? I'm literally like, they're like, should we do this or should we not do this?

I'm like, I wouldn't do either of those things. I'd do the same thing. But I don't know what else you should do. Someone just asked, people ask me to be on advisory committees because they have some semblance that I have ethical considerations. And I'm always like, no, I don't have any advice for you. I get asked a lot. Two things I get asked a lot is book quotes for back of book jackets and advisory. Oh, blurbs?

Blurbs and advisory. And neither of which I will do because largely I would rather watch TV. Anyway, Scott, let's go on a quick break. When we come back more, not Shark Tank, by the way, speaking of TV, when we come back, more listener questions. Fox Creative. This is advertiser content from Zelle. When you picture an online scammer, what do you see? For the longest time, we have these images of somebody sitting crouched over their computer with a hoodie on, just kind of typing away in the middle of the night. And honestly, that's not what it is anymore.

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That's www.alexpartners.com. In the face of disruption, businesses trust Alex Partners to get straight to the point and deliver results when it really matters. appoint and deliver results when it really matters. Okay, Scott, the next question comes from a listener named Utaka from Illinois via email, so I'll read it again. In a recent Pivot episode, Scott said, do you know what most CEOs have in common? Not pipsing people off. Boom! I'm sorry, I added it myself. Why is that? What keeps CEOs, often the most visible embodiment of companies and brands, from being out in front with the asshole persona like many politicians seem to be embracing?

There are cable channels and social media platforms for assholes, so why not asshole cola? Asshole phone service? Asshole coffee? Seems to me there's a market for consumers who love assholes. See Fox News. Thanks always for the great conversation and insights. So what's your asshole meter here on this issue of why not more assholes?

I think there's plenty of asshole CEOs, but I don't know. But you said they don't want to piss people off. I generally find, well, okay. So being an asshole, we live in an environment where everything from investor relations to politicians has become so starched that the market is really receptive to what they thought was authentic. And unfortunately, sometimes authenticity was conflated with being a jerk or saying really inappropriate, angry, non-civil things. And what I have generally found is that the most effective CEOs demonstrate a lot of concern for the Commonwealth. They're good people. And I just think the era, unfortunately, what I hate about the era of tech is that because of

Steve Jobs, mostly, people said, all right, if you're a nice person who's talented, you're talented. If you're a talented person who's an asshole, that must mean you're a genius. If you're talented, you're talented. If you're a talented person who's an asshole, that must mean you're a genius. And I don't, I think that they set the wrong tone for behavior at work. And what I have generally found is over the long term, the CEOs who are successful and build really rewarding long-term careers are people who genuinely act as fiduciaries for their employees. I'm not saying they don't make sure they get paid hundreds of millions of dollars, which they do. But the CEOs I have worked with are generally good people. They're generous, civic-minded people. I mean, I would look at Evan Spiegel. He and I had one lunch that I literally wanted to slap him. Silly. And he's evolved. Like, they evolve.

I think I like evolving CEOs, and I'm willing to give people a chance if they evolve. Of course, they're according to my specifications. But I think a lot of people do evolve, and the assholes do get washed out. I think Scott is right. Elon Musk aside, he's a very performative person. It works for him, but very few other people. There's not a lot of Steve Jobses out there. But here's the thing that the biggest threat in corporate America, and I'm parroting my friend, Dev Seidman, it's not immorality. People who are real assholes, they usually get starched out of the ecosystem. It's amorality.

And that is it's people that spent, go to benefits, have their name on the side of a hospital, are good people, send you a note when your kids are born, but ignore that whole teen depression going on. They don't do anything. And it's not bad morals that's teen depression going on. They don't do anything. That's right. And it's not bad morals that's fucking up corporate America or the externalities. It's ignoring.

It's turning a blind eye to some of this shit. It's amorality, not immorality. And that's where I think regulation has to fill a void. But I don't, you know, the asshole thing, it's great for media. It's great for getting awareness. Yeah. I don't think it works over the long term. Nobody wants to drink asshole coffee or cola, I think. Ultimately, it has a small group of people who also watch, it's a Venn diagram with people who really love jackass. Like, you know what I mean? Like, it's a Venn diagram of a very small amount of people. It turns off most women. It

turns off, you know, it turns off a lot of people when you behave like that. And it works for media. But up to a point, by the way. I think there's a point when you're a hand-waving jackass, it doesn't keep going. It backfires. Well, it works as long as everything in your company is up and to the right. And guess what? No company remains up and to the right forever. You have to be liked. Liked is better than disliked. And that's not to say you don't hold people accountable. That's not to say you don't make hard decisions and fire people. But the majority of the CEOs I know I would describe as people willing to make hard decisions,

but at their core, at their core, they are kind and they are very good at not making enemies. They show grace. And they are very good at not making enemies. They show grace. I remember I have a close friend who was put in charge of all of the magazines at Hearst. And the first thing he did was all the people who were supposed to get his job, he gave them promotions and raises and said, I want them to be my allies. And he knew that they were gunning for him and not being very kind to him because it was a Game of Thrones thing. But he showed real grace and generosity because he said, okay, I want these people to know I have their back.

I'm going to put a caveat there. Sometimes you got to kill one or two of them. Oh, occasionally you got to shoot people more than often. But I'll give you one of my professional role models. We were talking about kitchen cabinet. My old boss, Peter Henry, who was the dean and youngest dean of a top 20 business school, he was so obvious. Every time you spoke to him, he saw his role as the leader of our organization of Stern, 190 high IQ, unmanageable, difficult people called faculty, running a $200 million

business that had outside social impact on that and really know, like, with tenure, you have no control over these people. Right. And, but what he was so effective was, and he's been a role model for me, was he saw his job morning, day, and night, full stop, was how do I make you successful? Yep. What can I do? I am your advocate. I'm not here to try and get you to work for more, for less money.

He was like, how can I help you? I'm going to use all of my skills, which are immense, to make you really successful. Because if you're successful, we're all going to be successful. All right. So we do not believe in assholes, Yutaka from Illinois. We believe in good people most of the time. Flawed, but good people most of the time. Okay, Scott, here's a question for me. Roll tape. Flawed, but good people most of the time. Okay, Scott,

here's a question for me. Roll tape. Hey, Karen, Scott. It's Jeff calling from Singapore. The question is, it's mainly for Kara, although I also love to hear Scott's feedback. How do you prepare for your interviews? I listen to you across all the various properties and the depth and breadth and the number, the quantity of interviews and the quality is just amazing. I think you may be the goat and I really love the work. I just love to know more about how you prepare, what your process so that we can learn from you. Thanks so much. Bye-bye. Well, that was nice from my brother. No. I just threw up in my mouth. I just threw up in my mouth. I got to say I'm good.

I've been getting a lot of that lately. It's interesting. I was thinking like. Okay, hold on. Let's just look at those last two sentences. I really am good. And I've been getting a lot of that lately. I have.

When you say that, you mean people complimenting you on your interviewing skills. They have. Yes. That. Yes. I've been getting a lot of people. You know what? A couple things,

and then I'll let Scott pontificate on how good I am. I think I spend a lot of time prepping. I have great teams. I have great producers here and at Swyatt, the New York Times, and wherever I am, Recode, Decode,

really prep a lot of information. I only interview people I'm interested in. When I don't, I'm not as interested in them, I have a much less good interview. I just happen to be good at phoning it in when things I'm not that interested in. Amanda was noting this the other day. She goes, no matter what it is, you seem to have something to say on it. But I think I try to pick people I'm really interested in. Like recent Jon Stewart interview, I thought was particularly good. And I wanted to talk to

him. He wasn't particularly in the news. I just was interested in his relevance and the show he was doing. You know, things just strike me. Sometimes some things are offered to me, but most of the time I pick what I am interested in. And that helps a lot, being interested. And when you're interested, you are interesting. I know it sounds like a silly thing. I do a lot of research, but not a ton, not too much. I don't try to do too many scripts. Sometimes the stuff at Code, I do off the top of my head. I'll be honest with you. I don't do a lot of work. I go where the conversation goes. I listen to people. I try to make jokes. There's a lot of humor and stuff. But I'm also prepared to ask the question everybody wants to know. In the case of Stuart, for example, I asked him if he was relevant. I thought he may have, and I didn't like the show when I said so. And I think people like that honesty. I don't know. I just, I'm interested in things. And when I'm not, you'll never see me again, I guess. I don't this to someone the other day, I said, Scott always asks the question of left field that I wouldn't have thought of,

that maybe seems too soft, but isn't, is very revelatory. You often ask the question I never would have thought of, which I like. Yeah, so look, and not that you need it, I do think you're a great interviewer. I think that what you do, and I think Michael Smirconish does this, I think Stephanie Ruhl does this. I think Sam Harris does this. I get interviewed a lot. And what I've noticed about you, and I think you're really good at, is that you set people up to present their best selves. And even if that means asking them hard questions, it's a hard question they should be expecting.

And you give them the opportunity to make their case, and you're not trying to play gotcha. And you give them the opportunity to make their case. And you're not trying to play gotcha. And so, for example, you're, of course, I'll turn this back to me. There's been a few seminal moments in my life professionally. One of them was your interview of me, the first podcast interview. We never met each other. I went on your podcast.

And, like, everything changed for me professionally. You're very good at that. In terms of setting people up for success. In terms of – I'm not exaggerating. I draft off of you. I listen to you interview, and then I ask a question more about the personal or the softer stuff because I'm not a journalist. And so I can ask questions that journalists probably wouldn't ask about, you know, how did you feel, whatever it might be. Also around the listener mail we get and interviews, I don't prepare because I do think that the authenticity comes through when you're sort of doing it real time. That's just my approach. I don't prepare for it. I just kind of go where it takes me, including like, I haven't seen these questions we're answering. No, we haven't either. No, I didn't either.

And it helps because I think people, you give up some prep, you give up some data, you're not going to be sharp or smart, but people can hear, quote unquote, the authenticity. Yeah, yeah, it's an interesting question. I think one of the things, I do like your offbeat questions. I think I was thinking that I should do that more. It's not my style, but it's also, there's always been several very good answers. Like there was one, I forget the one you asked recently. I was like, hmm, I wouldn't have asked that, but I think it was Ben Stiller, one of them I liked a lot. The other thing that I do is a lot of them. And that's

ultimately why I'm good. When I started, I was not as good. I was very jump in. I was I've done there's got to be 1000s and 1000s of interviews at this point, many more than that. And so ultimately, when you do something over and over, just like an athlete or anybody or an actor, you get better and you get better and better and you have a persona and you are comfortable with yourself. That's the most important thing is being comfortable with yourself and comfortable asking hard questions and not, you know, also the last thing I'd say is every interview I do, I don't care if I interview them again. Like, if it doesn't work out, I'm fine. If it does, so you can't be sort of anticipating the next thing. I'm trying to think who I like as an interviewer. I was trying to think of someone you should, lots of people. I look at lots of people in their interviews. I do think Chris Wallace is actually

good. But it does strike me though, that all the men have the big jobs in interviews, you know, and here I think I'm better than they are. I honestly do. We'll see. We'll see if someone, if my light, my under the bushel light gets noticed by someone on high. We'll see. Oh yeah.

You're such a, such a wilting flower. And so are you kidding? Come on. I know, but I honestly, the guys have the TV shows, the big, okay, whatever. I'm just going to make that point. This is literally the only conversations Kara will have. Hi, I called you. I just wanted to get your thought on the seven offers I have from different mega media companies.

Not yet. They got to deliver. Anyway, you know who was a good interviewer? Barbara Walters was a good interviewer when she did those things. Everyone made fun of her. Barbara Wawa was quite good. She really did did those things. Everyone made fun of her. Barbara Wawa was quite good. She really did. She was good at conversation.

Not everything, but anyway. Thank you for that question. Let's go on a quick break, Scott. When we come back, more listener questions. Thumbtack presents the ins and outs of caring for your home. Out. Indecision. Overthinking. Second-guessing every choice you make. In.

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big savings on plans, and having your unused data roll over to the following month. Every month. At Fizz, you always get more for your money. Terms and conditions for our different programs and policies apply. Details at Fizz.ca. Okay, Scott, we're back. Now one that came in via voicemail.

It's based on your commentary on dating. I like how these are all based on your commentary. Asshole, see you. This one's on dating, which is frightening. Let's play the clip. Hi, Tara and Scott. So, Scott, I've been hearing and reading your insights on dating lately and masculinity. And each time your insights actually kind of trigger me emotionally

because they all just kind of confirm everything I've suspected, but didn't have the numbers or intellect to back up until you provided all of that. So I would really like a monogamous partner in my life and a family in the next decade as well as, you know, career growth, all the things. I want it all. But at this point, I'm feeling discouraged on the relationship side. For context, 30-year-old straight woman living alone. I work remotely in tech, so my community is online. And it just feels like there aren't that many options, and it's getting more scarce with each year I get older. So I am just curious what advice you would give me and other women like me. Is there hope, or should I prepare myself for the reality that my goals for a partner and family might not happen or just might not look the way that I

thought it would because of how our culture is shifting. Thanks. I look up to you both more than anyone else. And I would really appreciate both of your insights. Love you guys. Wow. Whoa. God, I want to cry. I do. What a lovely woman. Oh, wow. Well, you know, I'll have you start. I'll just say it is harder for straight women, honestly, in this world, in this context. Although, you know, it's hard for some men. My son, my 20-year-old, talks about difficulty of dating and isolation quite a bit. We talk a lot about it.

So, you know, I don't know. I don't know. I don't know. Scott, you have much more to say on this. But you sound like a wonderful person. And sometimes I look at, honestly, I look at men, I'm like, you're a bunch of idiots. There's all these amazing women I know that they should be dating. And, like, I have dozens and dozens of

friends who are not, they're in this situation as some are younger, some are older. And aside from me saying, why don't you be gay? Because women really do understand the value of people. That's not an option with most of these people. And so I'm always- Oh my God, you're trying to turn our children gay. No, I actually turned them off. I have several women who's like, I'd like to be gay. I'm glad you're trying to turn our children gay. No, I actually turned them off. I have several women who are like, I'd like to be gay. I'm like, you can't be. You're not allowed.

You like the penis. Move along. So, I don't know. I find it perplexing. I've found it perplexing for many years. I have wonderful, straight women friends, and many of them are single. And most of the men are not. And they also have women that are better than them.

Almost all of them do. Sorry. I think about this a lot. I get asked for a lot of advice around dating. And here's the reality. And, you know, everyone says, oh, there's someone for everyone. No, there isn't. Not necessarily.

And so much of it is a function of just market dynamics. If you live in New York or Miami, it massively favors the man. There are two and a half single women for every single guy in New York. And so when my friends complain about their girlfriends, I'm like, be clear. She would never date you if we lived in Atlanta or Dallas or Ontario, California. You get to add two points on a balanced scorecard of character, looks, economic success when you're a man in certain cities. And in other cities, it favors the woman. So there are a lot of factors here.

Having said this, we have this, because of technology, we now have Porsche polygamy, and that is the top 10% of men in terms of attractiveness get 80% of the mating opportunities, which does not encourage long-term relationships. There is this Peter Pan effect. And then the bottom half of men, because fewer are going to college, fewer are economically or emotionally viable, quite frankly don't satisfy the criteria for most women who sound intelligent and rightfully have high standards as this young woman does. What I would say in terms of advice is that you need to put yourself in a position of as much success or random success as possible, and it's the following. position of as much success or random success as possible, and it's the following. One, force yourself to put yourself in as many situations where a random meeting might take place, and force yourself to be aggressive. Accept opportunities to go to dinner with people. Accept go-to things.

Get out. You don't feel like it. You'd rather stay at home and watch Netflix. Go have dinner with friends. Put yourself in a situation. Put yourself in a situation to talk to strangers. Also put yourself in a situation where if you have coffee with someone and you don't maybe think, oh, this is great, maybe give it another shot.

Maybe have a second date. The best thing in my life, and I'm bragging now, is that I get to raise kids with someone I care a great deal about. And I walked in, I met this person at, I didn't think I was ever going to get married. Quite frankly, I didn't want to, but I didn't think I was ever going to get married or have kids. And it's the nicest thing. It's ended up being surprisingly nice. I saw this person and I said to myself, I'm going to go talk to this person before I leave, before I leave. It was uncomfortable.

And I was at the Raleigh Hotel at the pool. And my oldest son's middle name now is Raleigh. Nothing wonderful will happen to you unless you take an uncomfortable risk. Get out. Go up to strangers. Talk to them. Give men who express an interest a chance. Go start talking to men.

Talk to the guy in front of you at Starbucks. Serendipity is a function of effort. It's a function of effort. That is a very good point. Many of the people I went out with, I remember seeing and not doing anything, and I walked back in. One person I walked past was leaving, and I turned around and walked back in. And you know what I mean? I just did that. Same thing with meeting Amanda. It was a blind date, and I was like, oh, no, I don't do those. And I just said yes. I said yes. Same thing with my first wife. I was very bereft about

breaking up with someone, and I sort of squirreled away. I just moved to California. And when the weather started to turn, I said, I'm going to say yes to everything I'm invited to. Everything, everything. And I went to so many things like over, and then I met Megan. And so, you know, and we had two beautiful children. We got divorced, but what a wonderful outcome for that marriage. And so just, you know, and we have two beautiful children. We got divorced, but what a wonderful outcome for that marriage. And so just, you know, you never know where things are going to go, but you have to. I know people try and try and try, and it doesn't work. And I do agree, men can be, there is a trend, as Scott has talked about many times, about men being disassociated or isolated, especially by pornography, by social. That women tend to focus in on a small group of men

and not all of them. But there's great, there's, you know, there's great men out there. And believe me, again, my son talks about it a lot, like Tinder. He's like, I never get swiped on. I'm like, well, you're fantastic. Like that shocks me.

Obviously, I don't think you should be on Tinder, honestly. You should go out and meet people in person. And I think that's really my only thing is meet people in person. Social media is not gonna, I mean, I know a lot of friends who have met on social media initially, but that is not the way to meet people.

It just isn't. It just isn't. Your friends, your family, work, people you see that sort of interest you, go to group things, in-person things, whether it's church or whatever, is the very best way to make connections with people. Thank you. We should start a dating service. We should become like Yentas.

I love fixing. It's a total mess. I do, too. I have six marriages. I have six marriages to my—I just fix people, but I'm very tricky when I do it. I lie to people about things. But go ahead. But a couple things.

One, is it online dating? Is it meeting people? Is it forcing yourself to go to community? I think it's all of the above. I just think you do all of it, quite frankly, unless it upsets you or discourages you. But the other thing I think that's important is I think it's important to try and figure out a way to train yourself and have cognitive behaviors where you don't define the success of your life based on your romantic relationships or lack of success there. Friendships, your relationship with the community, your relationship with your parents, your friends. You know, what we all want is we all want to be loved and we want a place to put our love.

And there are a lot of different places in addition. And I think our society basically says to women that age that 90% of your happiness is supposed to be driven by your success or lack thereof around romantic relationships. And that's bullshit. It is. You can go for long extended periods of time without a romantic relationship and be very happy because of friendships, because of the love you can get and receive from your family and strangers and helping others and work relationships. So, I— 100%. I got to tell you, when I looked at all those movies, those rom-coms, I remember 27 dresses, all of them.

There's a million of them. I used to think, oh, my God, it sucks to be a straight woman or a man because of all the expectations and the imagery. Like, one of the things that was good about no gay depictions of love for the longest time when I was, now there are many, but there certainly weren't, was that I wasn't that prison of like you meet someone, you fall in love and everything's all heartstrings and flowers. And that was, I thought it was like, wow, you all are in a real prison.

I don't know what else to say. It's like they didn't ever have, we never got, gay people never, for a long time, never got that. And I think it was actually helpful because we didn't have it. Everyone's waiting for Matthew McConaughey. But generally, if you look at the market, and I'm going to make a rough generalization here. For the top 10% of attractiveness, however you define attractiveness for men, the world's never been better. It's too good. I mean, it's literally too good, and it leads to bad behavior.

It does. For the – call it the 50 through 90 for men, it's okay to good. For the bottom 50 percent of men, they're literally shut out of the market. I mean, they're just shut out. They don't have – you know what? They don't have bad dates because they don't have an opportunity to date anybody. You know what? They don't have bad dates because they don't have an opportunity to date anybody.

So there's huge variance, good and bad, in the quality of romantic opportunities for men in this country. For women, across almost all of them, I would describe it as just generally mediocre to bad. Yeah. For all. It's just. Yeah, for everybody. The variance is enormous. Beautiful women who get older. Beautiful women who had a great amount of choice then get older.

You've seen lots of people talk about that, which many people don't feel sorry for them. But that happens. It really is hard. It is hard. Here's my only last piece of advice, then stop me. I have one more. Date men who have been raised by lesbians. They're the best men.

They are. They are. They are the best men. I know you're such a man. What I will reinforce here, and this is for me, maybe this is our next show, a dating show. I think a man's relationship with his mother is a real tell. It's a real tell. It is. And also, I tell, you know, I've had women say, oh, I don't want to date him. He's divorced. I'm

like, the fact, if you meet a 45-year-old man who's never been in a long-term relationship, that's a red flag. You'd rather date a guy who's been divorced because what it means is he's capable of committing to someone. So the reality, and I'm going to be harsh now, women in their 20s are the most attractive person in the world for biological reasons. Men see them and think, okay, must impregnate this young fertile person. And they develop a series of expectations that sometimes decline faster than their expectations do. And it's very sad. The world is biologically unfair to women. Men, and then at the same time, it's unfair. It's a little bit unfair on young men. A 23-year-old has no game in our society. No game. He doesn't have the random hookups in college. And every attractive 23-year-old

woman wants to date a hedge funder who can take her to the Hamptons. And I'm being a huge generalization here. Yeah, that is a huge generalization. I know nobody who is like that. Sex in the city, they described it perfectly. There's a power flip. And that is men's sexual currency goes up as they get older and more successful, and women's declines. And it creates anomalies and weirdness along the way. Agreed. Anyway, this stuff is fascinating. It is. It is.

We should have a dating show. That's what we should do. But let me just stress again, lesbian-parented men are the best men in existence. Lesbian-parented men? They are. Is there a dating site for that? There should be. I just was thinking of that.

They are great guys. Every guy I know is great. Does your mom own a Subaru? The new dating service. We had a Subaru. We had a Subaru. What a shocker. Well, I had other cars, too.

Don't start. There are stereotypes for a reason. Don't stereotype me. There are stereotypes for a reason. I had a Volkswagen. I had a Honda Minivan. You have terrible taste in cars. I do.

As good an interviewer as you are, you have bad taste in cars. I love my bad cars. I hate cars, but it's fine. I get the cheapest one I can get that has enough seats. That's how I buy cars. Man, it was like there was a scratch on the car. And I forget. I must have like was taking snow off of it the wrong way.

And I got all these scratches. She's like, you put scratches on the car. I'm like, yeah, whatever. Like, I don't care. I hate cars. I hate cars. Anyway. This woman, this woman has a key component.

And one of the reasons she wants to get out there is in this won't, this can't come through on an app. She has a really nice vibe. Vibe, yes, she does. And you want to lean into your strengths, and that vibe comes through in person. So you want to get in front of as many potential romantic partners in person, because you can just listen to this woman talk, and you're like, I want to know this woman. I would make one correction. I look up to both you more than anyone else.

Maybe not. Maybe you should change that. Yeah, that's not a good both you more than anyone else. Maybe not. Maybe you should change that. Yeah, that's not a good way. More than anyone else? Fine if you look up to us, but not more than anyone else, especially this guy. Anyway, all right, last question. This is a fun one. Subaru.

Subaru. It comes from lesbian-parented men. LPM, you can put that on your Tinder profile. My mom's a lesbian. LPM, lesbian-parented men. It comes from John C. in on your Tinder profile. My mom's a lesbian. LPM, lesbian parented men. It comes from John C. in Larkspur. Oh, that's where my brother lives. It came in via email. Let me read it. Hi, Karen Scott. My wife and I enjoy the show greatly. We have our own six-month-old golden child, and you two provide a biweekly dose of sanity to our crazy lives.

We recently started discussing events we wish Pivot was around for. They want us for historical events. I'd love to hear your takes on the Chinese firewall and Y2K as they unfolded. What events do you wish you could have covered on Pivot together and why? Oh, Y2K would have been fun. I was at E-Trade and Yahoo that night. I was with Dave Filo of Yahoo and then the CEO of E-Trade, Kathy Levinson, and nothing fell apart. It was a terrible story. I would have liked to have had Scott there for that. I don't know, what events do you wish we'd covered today historically? The Spanish Inquisition, I think, probably, right? Well, Y2K was Web3. It was basically just, it was marketing blather to try and make money at consulting firms, but made hundreds of millions of dollars, if not billions, to helping companies prepare for this Armageddon called Y2K.

I mean, think about how ridiculous that is. When all the clocks and machines turn 2000, everything's going to fall apart. People were freaked the fuck out. Literally, my New Year's Eve that year of the turn of the century was at Yahoo. I just can't even believe I did that. What a loser I was. The thing that popped into my mind, I did with Stephanie Ruhl, we covered the Facebook IPO on Bloomberg. We said, we want you to come in and do live coverage. It was the most uncomfortable thing I've ever done in media because, I don't know if you remember, the IPO was delayed for two and a

half hours. It was supposed to go public at 9.. Yeah. It didn't go to – we sat there for three hours trying to think of things to say about Facebook. It got so – Nice blouse. It was this guy named Paul Kudrowski who's a really thoughtful guy. He is very thoughtful. Who I haven't heard from in a while. I know. What happened to Paul?

I don't know what happened to Paul. I think he's just snowmobiling and skiing. Probably. I think he has a nice life. He owns an island. But we sat there for three hours trying to come up with something to say about. Anyways, but I don't. I think the introduction of iPhone would have been fun to cover.

I went to that. So that would have been fun to have you there. Probably Steve Jobs would have thrown you out by that time. Oh, I'm going to see Top Gun tonight. That just popped into my brain. Good, good. With my voice. Maybe the very first Top Gun.

That might have been interesting to cover together. To cover? I think probably the iPhone introduction would have been really interesting for you and I to cover. I think Windows 95 would have been fun. That was there, too. Windows 95? I was a grad school. Yeah, Jay Leno was there, too.

Jesus, you're old. I'm real fucking old, let me tell you. I think what would have been good? When the internet went commercial, I was around for that. Scott wasn't with me. I don't know. I think we're exactly where we should be. Here's one.

Let me just ask what you would have done. When Walt and I interviewed Mark Zuckerberg, and he sweat that time. That was several, many years ago. What would you have done in that situation? There he was. We asked him about privacy and stuff like that, and he suddenly started sweating. When you're saying he sweat? Yeah. Remember, he almost fell that, and he suddenly started sweating. When you were saying sweat? Yeah. Remember, he almost fell over, and he's all sweaty. What would you have done? That was

a great- Oh, I don't think I had the maturity and the experience you guys did. I think you handled that perfectly. You gave him- Yeah. Didn't you give him a tissue or something? I don't remember. I made him take off his coat and gave him a tissue. Yes, I did. I was mom. Yeah, I don't have any insight there. I thought you guys handled that correctly. I think the iPhone debut would have been a really interesting thing for us to talk about and cover.

Oh, by the way, I would have been the guy who got it wrong because, you know, I bought three iPhones and I returned them all for my BlackBerry. I could not get off my BlackBerry. I had to buy five different iPhones. But that makes sense. A lot of people were like that. A lot of people were like that. That wasn't fresh. I loved the iPhone from the minute I got it.

I loved it. I thought it was great. Yeah, I loved my BlackBerry, too, by the way. I think that would have been fun. Covering BlackBerry would have been fun. I don't know. Lots of things. We're just good.

We like new, fresh things. But largely, we would like to cover the Spanish Inquisition. I don't want to answer this question. I thought the question was going to be, do you have any advice on parenting? And just let me say, if you're the dad of a six-month-old, pretend it's not awful. It is. It's not. It's not awful.

He's wrong. Zero to two, awful. No. Awful. Two to five, bearable. And then it gets actually pretty good. Okay. So let me just help you, my brother.

You're in Vietnam, but there's a plane out of Vietnam once the kid hits kind of two or three. So, just hang in there. Be supportive of your partner. No, this is so inaccurate. Be supportive of your partner. It's just an experiment to keep the thing alive. No. But it gets less and less awful every day. Every day. Saul was a delight this morning, laughing, laughing. We had a great time. No, no. The sleeping thing is a problem, but that's in general. Babies are awful. No, they're really not. They're not. They're not sleeping thing is a problem, but that's in general. Babies are awful. No, they're really not.

They're not. They're not awful. By the way, Amanda does most of the work with Saul, but nonetheless. They're not. They're not. You're wrong. I'm sorry. They're delightful, golden children.

There's no reason for us with a baby. We're never having a baby together. Let's just say that. All right. And on that note, those were great questions. That's a weird thought. I know that's a weird thought. Wouldn't that be weird? We should do one of those things where you combine the baby faces and see what our baby would look like. Let's do that. I'm trying to think how we collapse Shark Tank into a program about you and I having a kid.

That would be some kid. I would totally sue you for support. Anyway, those were great questions. Send us more. If you've got a question and you're curious about it, go to nymag.com slash pivot. Submit it for the show. Okay, Scott, this was a very lovely show. I really like this. I love our fans. I love our listeners.

I think they're amazing, and I love talking to them. Please come up to us at any time. We love talking to you. We think it's great, and it also makes our sad little insecure lives a little better. Anyway, we'll be back on Friday with a regular episode. Scott, please read us out. Today's show was produced by Lara Naim and Evan Engel

and Taylor Griffin. Thanks also to Drew Burrows and Neil Silverio. Ernie Andretod engineered this episode. Make sure you're subscribed to this show on Apple Podcasts. If you're an Android user, check us out on Spotify, frankly, wherever you listen to podcasts. Thanks for listening to Pivot from Vox Media. We'll be back next Tuesday for another breakdown of all things tech and business. Nothing really wonderful will ever happen to you without taking an outsized risk. We talk about that professionally, but it's also true

personally. Start a conversation. Push the limits of your comfort zone. The best relationships are a function of the serendipity and the effort. Go up, talk to people, get out there.