Maybe Twitter isn't real life

0:04Today on Great Chat, we remember Om Malik and in the wake of his passing, what made him and the tech media era he pioneered so special. I'm Helen and I'm joined by Ashley. Great Chat is brought to you by Mercury, radically different banking loved by over 300 ,000 entrepreneurs. We use Mercury to run this podcast and love recommending it to other founders and fund managers. It's free to get started. Try it for yourself. Visit mercury.com to learn more and apply online in minutes. All right. Hello. Hey. Did you catch up on the New York Times article from the weekend about how impossible it is to make life work in San Francisco when you're only making$380 ,000 a year or whatever the actual number was?

0:51I will admit to like only seeing the like Twitter summary on this, but I can imagine that both you and I are like shaking our heads and like doing the math on our early San Francisco existence because, oh my gosh, at 27, I can't even imagine having a combined$365 ,000 face pay salary with my partner. it's such a sign of the times and how warped I think people's expectations are. And also a bubble because I think the thing that I'm baffled by is these young people, they voluntarily spoke to the New York Times on the record and gave their full name and employer, which means it didn't, as very smart, capable people, nothing, no alarm bells on like a, But this might be absolutely out of touch.

1:52I mean, even I live in the city of San Francisco, and this is extremely out of touch because I think somebody just did like a zoom in on Zillow rents. And it's like, yeah, if you're only looking in these two neighborhoods, like, it's really hard to find an apartment under whatever it was, like$5 ,000 or whatever. But look at the rest of San Francisco and all these other places. So it's also it was very selective. $4 ,000 when you're making that amount of money, like that math, math's for me. Like I have had way worse ratios. I think my first apartment in San Francisco was a two bedroom that I shared with my roommate and we split rent that was$2 ,500 a month, but I was making$35 ,000 then.

2:40So their ratio way outperforms mine. And I was also living a good life. Like I wasn't living lavishly, but I wasn't suffering. Like you wouldn't have spoken to the New York Times about how hard life was. That's how good your life was. I definitely would not have done that. There was like a similar controversy in this city, New York. recently. There was some like man on the street video interview and some guy went up to a couple girls, a couple of young women, sorry, and asked them their salaries and asked them what they did, what their salaries were and what they pay in rent. And one of them like very wisely declined to share her salary.

3:28She did product. That's right. And the other one was a Stripe salesperson? Yeah. Sales at Stripe. And she makes$300 ,000 a year and she pays$7 ,000 for her apartment. Now, what was edited out of that clip later was that she splits that rent with her boyfriend slash partner. But it was like the timeline was freaking out. And it was freaking out on like, wait, she makes$300 ,000. I'm like, oh, you guys don't know how like tech sales works. Like that's not shocking to me, but it was very shocking to the timeline and actually spun out an entirely separate conversation around like no one thinks about like a tech sales career, but it's a great career.

4:17And that can be very true. No, I did not see that. My sister went down that path for a while. But then also like the$7 ,000 rent, which I think if you live in New York, you're not blinking at that. Of course, that kicked off a whole like what is the right ratio of like after tax salary to rent. And I think people who live in cities like New York and San Francisco are very used to having a higher ratio of a higher portion of their income going to rent or going to mortgages because that's just the price of living here and all the opportunities that come with it. But a lesson to young people, don't share your salary with the internet.

4:59With the New York Times. Well, so one sort of short rabbit hole I went down was how I have this feeling that this is a very San Francisco-specific phenomenon. And New York has always been expensive. New York, there is no ceiling. If you want to find an expensive apartment, And it's like, there is, you know, there is no, no limit. I moved to neighborhoods recently. Yeah. But like, New York is still to me a place where you go somewhere and there are all types of people there. And I mean that in like every sense of the word. And in San Francisco, so I'm like, you know, hi, I'm visiting my sister and she is the reason why I moved to San Francisco 20 years ago.

5:39And, you know, sort of like reflecting on one of the, what is the like biggest change, right? There's all these things that have changed. And I keep coming back to, I think when I moved to San Francisco 20 years ago, tech was this small thing. There was always tech, but there was also finance. San Francisco was very much the West Coast finance capital of the US. And now it feels like San Francisco is a single industry town and everyone in the city works in tech. Therefore, the rents get adjusted to that versus accommodating for needing housing, adequate housing for every single group to make a city be successful.

6:23And I think that post pandemic, we started to see a lot of restaurants struggle to have like waitstaff because there were just no people within, you know, the city limits or even like a short commute. And so I just can't imagine something like that happening in New York City. One, it's just so much larger of a population. But I think the other thing is just like New York has always been a place where you can find a very cheap, you know, small apartment somewhere in like even a pretty good neighborhood. Yeah. I mean, you're probably not living in the West Village and waiting on tables, although maybe you are while you're going to school and if you have help from parents, which is not uncommon in New York.

7:05I think the thing that blew my mind about New York when I moved here was how much having a subway system changes everything because a subway ticket from I'm a far out, you know, stop in a non-Manhattan borough. It costs the same amount as like going one stop like that. And so it's like kind of a great equalizer. And I think that the housing shortage was already a problem in San Francisco, right? Because it's such a small like geographic footprint. And I remember even, you know, in my 20s and 30s in San Francisco, like, you know, there There was already stories about people commuting like two or three hours to get into the city for their jobs and how that was making it impossible for teachers or service workers, etc.

7:55And so I can only imagine how strained that is now when like everything is getting so prohibitively expensive. But yeah, people expect New York to be expensive. And then New York, you can actually be quite creative. And, you know, the apartment market is crazy here too, but it's just much bigger. And so you have more room to play. But beware of speaking with reporters. Like if a New York Times writer wants to put you in a story, there's like a very good chance you will be made an example of in some way. If not by the author, then by the internet that reads that story. Yeah, it reminded me of that.

8:36There was that local paper, maybe in Palo Alto or something. It's been named so many times. So I want to say that this is like decades old. But it was like, gosh, there are so many billionaires. Us normal millionaires can't survive or something. And it was just such an out of touch comment and crazy and highlighted in a physical newspaper. And now we have a new refreshed version of that. I saw somebody on Twitter call it performance poverty this morning on like, you know, these people, they actually think that they are living paycheck to paycheck, but it's most likely that they are maxing out their 401ks and, you know, like paying their credit card bills off in full.

9:20And it might feel like a paycheck to paycheck in that their checking account balance is going low. But like, that's not what people mean. Going on vacations and eating out a lot. That's not what people mean when they say paycheck to paycheck. Yeah, yeah, yeah. No, it's funny. It's funny. I've become an unwitting lead for a story before, but it was like humiliating in a different way. I think I had tweeted about it, but I was at this cafe near Caltrain. I think it was called The Creamery. Do you remember this place? It was like a – Yeah. Near Caltrain. Do you remember? It was like an institution.

9:58Zero ambiance. And a useful location. Yeah, three parking spots and just like dust from the Caltrain. Exactly. And I was – I don't know why I was there, but I was there for some reason. And some guy came up to me and he was like, hey, are you single? And I was like, I am. And then he was like, do you want to try my new dating app? And I like tweeted this as like a self-deprecating thing. And then I became the lead of a San Francisco Chronicle story about dating in the city. So that was my. Oh my gosh, that's incredible. And I'll be Googling that immediately. That was my claim to fame. I had like put it out on the internet.

10:45So what can you do? Speaking of New York. We had a wild election last week. Yeah, I liked your take on it. Whenever the ultra political San Francisco tech crowd starts poking at New York, I'm like, oh, God, something happened. Honestly, I felt like there was more commentary from San Francisco than there was from New York. I know. And it's like all of us are watching all the same people say like New York was the greatest city in the world and now it's over. Everyone needs to move out. and it's like, I bet Mom Donnie's approval rating is like through the roof and people seem really, I was just there.

11:27I was just there in June and it was like the happiest week I've ever seen with the Knicks and weather. I was about to say that Knicks bump is like, you know, the fun thing that I picked up on was if you looked at the folks who like kind of did not perform well in the election they are like huge twitter personalities and i feel like all we read on twitter is how twitter is real life like you have to build a following like screw the mainstream media right and then like it was jack schlossberg schloss schlossberg um and george conway so kellyanne conway's ex-husband you know these guys are like super posters they are they are They have huge followings and, you know, across different social channels and great personas for social.

12:20And it just didn't translate to vote. So I was like, ooh, what does that mean? And the guy, you know, and the winner, very low profile, you know, not a tweeter. And so it's like, oh, that's a narrative violation. I don't know what to make of that. I mean, I bet if I went door to door on my block and asked how many people were on Twitter, it would be very few. It would mostly be my house. What do you mean, Ashley? I think it's just such a good reminder of what a little bubble it is. I loved Angela's question, which was, if I live and work in San Francisco, but I'm not on Twitter, does that mean I'm technically outside the bubble?

13:05And I was like, ooh, thought provoking.

13:11I mean, one version of the bubble. Yes. I think Angela, since you work in venture, you can't be outside all the bubbles. So true. I don't want to draw too distant a parallel, but it does feel like that right now is everyone must become like a media company. And that is the the path to power and influence and capital and winning races. And even as someone who like enjoys that strategy and maybe like employs it in the tiniest way in my own career, like it's kind of refreshing to see that not. Oh, totally. The case. I mean, again, like politics aside. Right. Yeah. But in all things, actually, you're so right.

13:58Like I was just thinking how sometimes it's like a little, you know, uninspiring to be like, is this who we have? And this idea that there is this underground of potential candidates or, you know, potential leaders that are that do not have a social media footprint that are extraordinary and capable of winning is like very inspiring. It's like, oh, the pool just got much bigger. It's not just the people that I can see. Speaking of being extremely online, should we talk about Ryan Peterson's big moment this past week, which had nothing to do with supply chain. I think he went on, was it Harry Stebbings or which podcast it was?

14:37Yeah, 20 BC. The little clippable, rage baby thing that went viral was he said that working from home or remote work specifically is white collar fraud, right? He goes on to say that he's got a three year old and a five year old and when he tries to work and like the idea of working from home is a total fantasy you can't get any work done they're like constantly coming in and bothering him and so that's why they're in the office five days a week and that's why you're seeing this return to in office and um you know i think there are a lot of people who believe that but i think it sort of struck a nerve in particular with a lot of you know i think in this case moms um who already, I think, sort of battle this, you know, unfair question of like, oh, well, how will you juggle being a mom and being a founder or a fund manager or in these questions that men usually don't get.

15:33But his sort of throwaway comment about this sort of, I felt like it sent us back in terms of like, oh, great. I mean, there are so many parents, they're usually millennial parents who talk about even just being able to work from home two days a week and how much that helps them, not having to commute specifically. I have a slightly different take, which is that I think this was great. I think a lot of people do believe this already. And he voiced it. And then there was just instant pushback. I mean, maybe some people are only listening to the pod or only seeing this, you know, this comment, this clip in isolation.

16:17but it sparked this really big dialogue with a lot of super impressive people weighing in and having a very different viewpoint. And so I think I'm now – this is the kind of thing that five years ago would have like pissed me off. And now I'm like, great, let's put all our shitty opinions out there. And then let's have the debate in public and let's see that there are like so many different ways to do this. And especially, again, when it's sort of like an unspoken assumption, I think those are maybe the most dangerous. And so it was fun. Like Claire Vaux, formerly of LaunchDarkly, now she has her own company.

16:59I think it's called ChatPRD. She has her own podcast. She's very much like an AI creator, influencer person on X. I think she quote tweeted. It was like, this is a skill issue, which I thought was such a fun comeback. But like, and then listed all the ways that she's like balanced having a super ambitious, successful career with having kids. May Habib of writer sort of responded to this in a very nuanced way. In a recent podcast interview with Alex Conrad of Upstarts, there were also a bunch of men who pushed back. So I'm just like, let's just put it all out there. And at the end of the day, there are people who are not going to be able to work from home with a bunch of kids running around.

17:42That is probably true. And then there are people who are able to do it beautifully. And everyone gets to pick and figure out what works for them or doesn't work or whether they... I think the future looks a lot more like that where there's this spectrum and CEOs are honest about what company culture they want to build. And then workers self-select, right? Like that's why the carry linear thing that we talked about a couple of weeks ago where he's like, everyone on the founding team or exec team, they're parents and we really fight ourselves for having work-life balance, although we're not allowed to use that phrase anymore.

18:18And like linear is doing great. And so maybe there are people who are keeping score and they're going to get real nitpicky on like, well, enterprise value accrues when people are in office and 9-on-6-ing or whatever. People are going to vote with what job offers they take, where they deploy their capital. And that, in my mind, that is fine. I have three close friends who took jobs at OpenAI over the past year or two who have kids. And they all approached it in a very similar way. They were like, I made a pact with my husband or wife, and I'm going to go work at OpenAI for one year. And I'm going to 996 it and never see the kids.

19:06And basically, my partner is going to be a solo parent. But that one year will get us one year of vesting. It'll give me a bump on my resume. It'll refresh having been at this really recent AI company. And that's our plan. And I was like, what a great plan. So the challenge is retention, right? It is very expensive to like be training and churning employees. And so, you know, I think that there are trade-offs that we have yet to see because we're still so early on this cycle. But isn't it great too that like rather than getting mad at companies or leaders for the cultures they've set, like just having more transparency around it and people are opting in.

19:45because like the worst thing is to join a flex sport or an open AI thinking you're going to like work remotely and like have chill out. Like, you know, it's, it's, that's, that's unfair. And so I think as long as everyone is going in eyes wide open, that's great. It's funny. When I first saw this clip, I was like, oh my gosh, hair. I just, I saw Harry Stebbings excerpt and I thought he was the one who called it white collar fraud. And I was like, he did Ryan Peterson such a disservice by framing it that way because otherwise this is just like Ryan saying what he's capable of. And then I listened and I was like, oh, Ryan, you've gotten too good at the internet because you did this.

20:26You did this to yourself and you sound like an asshole when you could have just sounded like a human being who's like figuring out what works for you and what you believe and how you're setting culture at Flexport. So it's also funny. I think sometimes people in an effort to get engagement to engagement backs to make things worse for themselves. But who knows, maybe this is considered a huge win by Ryan and his team. Maybe. Should we dig into our main topic for today? It's a little bit sad. A lot sad. Definitely sad. I was going to say like the second half of last week was sort of like a wash.

21:07We had some very sad news that Om Malik passed away at the very young age of 59. You know, what followed, which should have been predicted, but I don't think that we had seen anything like this in quite a long time, was like sort of an outpouring of love and remembrance. It just felt so different than how people usually mourn somebody in this industry. And so Om, he started GigaOm, I think it was 2001? Yeah, he was doing it on the side for the first years. And I think in 2005, I want to say, he went like all in on it. That's right. But he had a career, you know, he was a reporter at, where was he?

21:51Was he at Forbes? He was at Forbes. He was at Red Herring. He was at Business 2.0. Oh, so a lot of the, like, obviously Forbes is still around, but publications that define a certain earlier era in tech. Definitely. And then, so to me, I mean, my personal story with him was just, I worked in advertising, never paid attention to tech or the startup scene. But then I started, you know, interview process at Facebook and I needed to get smart. How does this industry talk? And what does any of this mean? And I remember reading GigaOM pretty religiously. And so that to me was like my sort of like my one-on-one into the startup and tech scene.

22:31Your indoctrination. Totally. And what a great guide, right? What a gentle, wonderful, wonderful guide. And so I think GigaOM eventually shut down in like 2015 and OM became a full-time investor. So he started as a venture partner at True while he was running GigaOM. And then he became a full partner and then eventually a partner emeritus. And so he would still duck back in and do some fun things with the team. And so I was so lucky to be able to work with him during my venture partner gig. And so very sad for the team at True. And so the thing that we've been wondering is like, what made him unique?

23:18And then what about these tributes? What are some themes that are coming out that feel so unique and frankly, really different in this moment? I saw a Hunter Walk short post where he was like, at a time when tech is sort of like figuring out its moral compass, like we're losing people who... Figuring out is a nice way to put it, Helen. What did he say? Spinning? The moral compass is spinning? yeah yeah the implication was like we are not in a in a in a great place and that wasn't meant i didn't think to be political because i don't think om was known to be political but what he was known for and you can read this very clearly in a lot of the the tributes is that he was very honest and he always spoke his mind and you founders felt like they could count on him to be very honest about what he thought of their product and their ideas but in a way that made them feel supported and cared for like he was on their team and so you know held back no punches whether it was just in person you know dialogue or in a review like in a in a actual like tech review like in his newsletter and i think that that's pretty special because today and this sort of like you know rage baity pick a side sort of you know thing that we're subject to that is so rare and so So to be able to both be honest and critical, but also do it in this way that was full of love to me feels pretty unique.

24:48Yeah. I mean, I think you knew Owen better than I did, given the true relationship. I mean, I crossed paths with him a handful of times in my early PR career and also a little bit socially. I have a lot of friends who are very close friends of his. and he officiated their weddings or godparents to his children. I was blown away by the tributes, not the depth of them, but the sheer number. I knew how important he was to a group of people that I know quite well, but then it felt like dozens or hundreds of stories and tributes with that same level of depth. And I think for folks who – obviously Om was like very prolific in his blogging days, but he was also like an introvert and he was kind of quiet.

25:45So it's just like amazing to sort of compare like what you know of someone's persona with like, oh my gosh, like he – I don't know how he scaled his friendship and his empathy at the level that he did. And over so many decades, my Twitter feed and Instagram feed and text messages were like, you know, filled with own tributes and memories. And I was just like, wow, this must be so confusing to like a 20-something in tech. Assuming that they're even seeing what the algorithm is showing me, how can one person not only have touched so many lives, But like be so beloved, especially in this era when there is a lot more contention and controversy between, you know, the builders and the people who are covering tech.

26:40And so it kind of like brought me back to, you know, the earlier – we sort of entered, Helen, the startup industry around the same time. And I think like the thing that made this possible, aside from, you know, there's the specifics of OM as a person, but then there was the broader context of like how small the industry was then. How could he have officiated this many weddings? How could he be a godfather to this many kids? It was small and he was like spending time with founders for years before writing about that. You know what I mean? These were actual relationships. It was far less transactional.

27:19And I think to your point around the seeming disconnect between he was beloved, but also he was like critical and honest and how can those things coexist? Like I feel like tech was not only small, but it was like younger and maybe more fragile coming out of like the dot-com bust. And like I think he really came at it from a place of like wanting to make tech better, like products better, companies better, leaders better. And people felt that intention. And so it was like a very human time. And it's very hard to reconcile with, you know, like obviously there are real relationships being formed.

27:59Yeah. Today. But, but the, what we see, the performance, uh, that we see every day on, on, you know, uh, various social media websites is, is much more antagonistic or much more transactional or much more marketing oriented. And so that like, it's just fascinating how much things have changed in like, you know, just the past couple, not even two decades. Um, Um, and, uh, and I think like the, this moment has been really like emblematic of that. Yeah. So, I mean, I think one thing that it did for me was sort of reflect on like how different things are today. I mean, you can reflect on how different was probably back then, but also what does that mean today?

28:43And I think, you know, smart people are able to hold two opposing ideas, you know, at the same time, they're able to navigate nuance. They're able to, you know, take critical feedback and not let their emotions get in the way. Right. And your number one rule, assume people are smart. I actually thought, wow, we are assuming people are stupid today because it is so pick a side. Journalism should be celebratory. You know, what's with all these takedown pieces? Why can't we just be positive? And to me, that's like, oh, we are treating our audiences that they're stupid. And so to me, like that, it made me think about, oh, that's imagine of being a young person starting your career.

29:28And that's what you see that you're treated. It's like pedantic. Even if you go to Ohm's Twitter, the pinned post that he has literally is from November 2022, a month after Elon bought the platform. And it starts with less Twitter, more writing, or less Twitter, more internet, or something like that. It doesn't mean that he's going to stop sharing his perspective and stop writing and being a part of this ecosystem, contributing to it. whatsoever, but it's just like, this is not the way I want to do it. And, you know, and then you look at one of his last tweets before he passed, which was like him standing up for Keith for boy, about how he's an excellent investor.