Are startups a young person’s game?

0:04This week, we're tackling a somewhat taboo topic, age. Young founders are valorized, but for everyone else, is it harder than ever to break into tech? How do you stay relevant when you're a decade plus into your career? I'm Helen, and this week we're joined by Ashley, Sally, Mac, and Angela, the whole crew. This podcast is brought to you by Mercury, the fintech used by over 200 ,000 companies to simplify their finances. We're huge Mercury fans here at Great Chat, and we use it to run this podcast. A few of us are also current customers for our funds and startups, not to mention the dozens of founders we've backed as VCs, angels, and scouts that run their businesses on Mercury.

0:40If you're launching a startup or fund, visit mercury.com to apply online in 10 minutes or less. The onboarding couldn't be more intuitive or delightful. Quick note, Mercury is a financial technology company, not a bank. For more details, check our show notes. Hi, ladies. Wow. We have like a full group for this week, which means that none of us are at Burning Man. oh yeah happy burning man week to all who celebrate which is no one here um i'm very much enjoying the quiet streets of san francisco but this year everyone has starlings so we're getting the play-by-play and as you guys know there's a massive desert storm and so the build time is uh it's chaos you guys are we going to talk about how burning man is cursed like in the 2020s we had like yeah that like swamp we had pandemic then we had nothing then we had nothing then we had burning hot man i was there and it was 110 degrees during the day and like 80 at night what was the year where it was miserable flooding wasn't that was last year and now we've got hurricane man like i'm sorry this is insane windstorm man global warming man And they're going to have to move it to like November or some shit.

1:59Like this is crazy. Global warming, man. It's going to move to an underground bunkers in New Zealand. That's going to be the new celebration. Oh, that hurts my soul. Remember, it started at Baker Beach in San Francisco. Maybe they should move it back. Can you imagine all of the people with like the Sea Cliff properties being like, get these hippies the fuck out of my backyard? It's funny. I saw some posts about like how terrible, like there were all these headlines, like do not come. It's like, it's terrible. They're having to rebuild all the camps. And then there are like the staunch defenders and the replies being like, no, this is what Burning Man is about.

2:40It's about resilience. Like this is part of it. Like the funny thing about that is all the CEOs are flying in their private jets and then they're going through their hard labor to build. I think someone else is building their camps would be my, would be my hunch. okay but also low-key guys if you've ever driven into burning man flying is so nice i don't blame them for it people are waiting like 15 hours to get in just like by the time they actually even make it out to bumfuck nevada mac are you the only one of us who's been to burning man no sally's i've been i was gonna say like i i doubt it statistically five area girls one of them has been to burning man probably three like what what inspired you to go i spent a lot of time making fun of my friends who went and um eventually they were like shut the hell up come with us come with us and see how it goes and i had a great time i went twice it was a good time i don't think it's like not my personality but i loved it it was a good time the first time i went i was actually i was leaving san francisco and i was like what's the most san francisco thing you can do before you leave and a month before burning man someone gifted me a ticket and i went with one duffel bag, which clearly was not the prep mode that I needed to go into.

3:52But I survived. I never went to Burning Man, but I did have like an anonymous Twitter account that was like a VC at Burning Man and was like tweeting from the playa. Do people know this? No, I'm like outing myself. I should have like, you guys, they handle, but I want to go back and look and see if the jokes are any good. Um, but that was the extent of my burning man, uh, burning man, uh, participation. All of my closest friends are burners and they have, you know, weeks of weeks and weeks of prep before they leave. And like, I've helped out on so many projects and floats and then never, ever wanted to go.

4:31So I feel like I'm this person that like had every opportunity to go every single year at Living in San Francisco and never went. So I don't know if I'll ever go. I have to say this is not exactly the same thing, but I spent like two nights in the Govi Desert. So it's not the Nevada desert, but it was a very hot desert. And my conclusion was I didn't really need to do that. I didn't enjoy the heat and the sand. I just love hydration. I like hydrated skin. I feel like one of those terrible Burning Man people when I say this, but it's not really about camping. I know. I know. for like, ooh, like I really just love the rustic lifestyle.

5:10I think it's more about like, hey, I want to go do something that feels like a cross between like a music festival and an art festival. And also I can make up for the fact that I have no personality beyond this. I will say like 10 years ago, it felt like Burning Man. And maybe this is just based on who was really promoting it became such a tech thing. And it was like all the tech billionaires were there. And like the jokes were that like deals were getting done on the playa. I don't, is it still a tech thing like i'm just not seeing a lot of it in my feeds like i don't know if it's relevant started to get sponsors and like you know there were like water sponsors and like you know that really changes the vibe of most things there's only one way to settle this which is we have to go in person so i would hate to see angela on the playa riding her bicycle across it's always it's always like that person who like ends up having the best time and has like the most epic yeah watch out guys when great chat goes to burning man i'm gonna go crazy so yeah we'll we'll call our camp hydration camp for for helen yeah sounds good everyone can come to get their moisturizer and like it'll be it'll be it's sponsored by road that's the dream great chat hydration camp sponsored by road i'm manifesting it now wait road like the lip balm like the oh road or row because i don't know we wanted to talk about row as road but we can talk we can talk about not the segue good segue to row row which has huge marketing dollars apparently because it's on every one of my feed with serena williams i was defending serena williams so hard in like the group chat in the comments in the everywhere i was like you guys she's like the greatest athlete of all time.

6:56She's not using GLP ones.

7:01I was wrong. I was wrong. She is out and proud using GLP ones. Greatest athlete of all time. They're for everybody. Oh my gosh. They're all the receipts of Mac. It's so, this is another, another example of like, um, like the bifurcation, like on Twitter, I felt like Twitter was very celebratory or at least my feed, which tends to be more like tech. And then people were furious on Instagram. I went and looked at the post that was like a combo from her and bro, and people were so disappointed and so upset. And I'm sure she had all this priced in. I mean, no one does this and doesn't think about what are all the potential reactions.

7:39But I think that the overriding one I saw and the one that I grapple with the most, because I think Serena has, you know, she should do whatever she wants with her own body, just like we all should. But like, like the impact on like young girls and young women who like have really looked up to hers as an athlete and someone who's like broken a lot of barriers. And, and I think like the message to, to younger women around like weight loss is like a really tricky one to navigate. So that was the, that was the Instagram sentiment. And then on, on Twitter, it was just like, yeah. Yeah. I think generally it's like people are separating her as an individual who should be totally, you know, like she should make her own choices and, and, you know, nobody is criticizing that.

8:20But I think then like, you know, when you're a celebrity, there's also this, all this pressure that, you know, everyone's watching you and there, there are young women who look up to you. And I think, yeah, I just commented like, you know, I think she's like the world's greatest athlete. And there are a lot of young female athletes who, you know, are muscular and athletic and, you know, they probably, I don't know. I don't know how you would feel. I went down a rabbit hole of looking at like the prior like weight loss, medication, crazes. And I don't think it's remotely fair to compare GLP ones to like fen-fen from like a health perspective.

8:55But it was really interesting to see that for prior sort of like eras of this, even for ones that were very mainstream, there a lot of like celebrities that were openly talking about their use. And so this is like a big shift because GLP-1s are kind of like an elite drug, not just because they're so expensive, but because, you know, Elon is using them, Serena is using it. Like there are a lot of people who've talked about using GLP-1s. And we were talking about the group chat. Part of that is because these drugs, you know, have been proven safe for people using them for diabetes for quite some time.

9:32And there seem to be a whole host of other benefits. But also just like culturally, the macro, like we're in this like longevity sort of moment where people are trying a lot of different things to extend life and be healthier. And if you just look at the crazy antics of Brian Johnson, yeah, like taking GLP-1s doesn't seem like a big idea and could actually be seen as something that's like health promoting. And so it's interesting to see how like culture has shifted to meet this moment to make it like OK or even admirable to be open about your use of like, you know, a medication that is not new, but is new in this particular this particular application.

10:14Yeah, I agree with that. Also, I was we were having this similar conversation at dinner last night with a group of friends. And one of the things also is like, people are our age that are using GLP ones are, you know, we're more educated or done more research on the drug itself. Because yeah, it was a diabetes drug that now is has all these added benefits. But as a younger person who, you know, sees this ad and sees, oh, there's no risk to it. But there's plenty of risks that are still yet to be determined, including I think one of the potential side effects is like dizziness or eyesight is one of them that have come up.

10:54And so, you know, my friends who are on it are monitoring these things just to make sure. So I think in that, like, it's a little bit worrisome to me to see that someone like Serena is promoting it. And I think the other thing about it is, isn't Alexis Ohanian an investor in Roe? And that was not disclosed. I know that was some of the fallout. Listen, when we talk about value add, like he said, new bar. Oh, he did. How can I be helpful? Here is my famous spouse to promote your product. I think overall, though, I read that eating disorders are down, like the prevalence of eating disorders. And I think that's a really good thing.

11:33Like I grew up dancing and like, you're always in these like very small, you know, uh, leotards and things like that. And so everyone's very body conscious. And so like, I grew up kind of around that culture and I think that it's very different now. So also the Gen Z, I think are more healthier in their weight. I don't know if that's, that's true or not, but, um, like Addison Rae and you, you look at some of these artists, um, they're more healthier in size. You see it like when you go to like collegiate sporting events, like, um, you know, I always have this reaction whenever I like see college cheerleaders.

12:06I'm like, oh my gosh, like all body sizes represented and they're all just as talented. And it just like, that wasn't the case. That's what I was going to say. I didn't want to, I mean, I didn't want to date myself as a millennial, but I was just thinking of that episode. Pretty sure this is like so squarely the millennial. Just like that, which is, you know, the sex in the city spinoff. And there's that scene where Charlotte is very uncomfortable about how she, her body looks in this dress. And then she sees her younger colleagues who are, you know, of different body sizes and openly wearing, you know, different clothes.

12:39And so I was like, oh, I wonder how much of the discourse we're having is in millennial circles and how, you know, I don't know if the Serena ad impacts Gen Z in the same way. Oh, that's interesting. Think about it. So you guys saw the Mid Journey meta story. Any thoughts on that? I went to a dinner last night and somebody was talking about how Midjourney is probably like one of their top most used AI apps. And I was like, for what? Tell me. What's their job? Exactly. And they were basically describing that they create these like fantasy sort of situation, like they use it to create content. She's a founder of a B2B company.

13:20And I was like, tell me everything. And so I thought that was a very creative and interesting use case, but it was just not one that I thought of. And so it was my first time where I was like, huh, Midjourney for a B2B use case. Okay. Midjourney is such a unique case. They're one of the ones that have never taken venture dollar or outside dollar. Respect. Yeah. And they're making a lot of money. So two years ago, it was reported 200 million in ARR. Now they're reportedly up to five. They only have 150 employees. And it is still one of the most used image gen out there. And remember, it's also on like a pretty shitty UI with this like Discord.

14:01And I was talking to somebody about this and I was surprised. And it's just like creature of habit, even though it's not so intuitive to use on Discord. It's been around for a lot longer than a lot of these other image models. So I think an interesting added benefit of having Facebook and Meta, you know, license is interesting because then you have all these applications like you can use through Instagram or other interfaces that are much more, much more useful. I think the other unique thing about this deal was, I think it was Alex Conrad who reported well, and then Alex Wang tweeted right away, is that it's a licensing deal.

14:41And Meta certainly has the war chest to purchase Midjourney if they wanted to. So I'm curious what the behind the story behind the scenes story about that was. I mean, maybe they tried. I think a founder that refuses to take venture dollars might also refuse to sell. If you're running your business the way you want to and you're making half a billion in revenue and you're doing everything on your own terms, I could have imagined this. like even just hearing the word licensing, because that's usually a component of like the acquisitions, like it like makes me, makes me stressed out. But like, in this case, they did like a straightforward license and there's no, you know, there's no CEO leaving to join Meta.

15:21So, so in my narrative inside my head, I have decided that, um, the founder and CEO, uh, David Holes, is that who it is? Like he was the one, he was like, no, thank you. I refuse to be acquired or, um, like, you know, aqua hired and, and here's what, here's what you can have meta. So did you, did you put that scene together in mid journey? Yeah. Right. Like I'm living for this fan. Yeah, exactly. Guys, welcome to my brain. Elaborate, elaborate confrontation between Mark and David. Um, but, uh, but yeah, I love to see it. I mean, the image space is, I mean, we talked about this like over and over.

16:04It's the models are getting so good that you with a naked eye could probably not be able to tell which model was being used today. There are no more weird hands. No more weird Will Smith spaghetti eating. Everything's now, you know, we can defy physics when it comes to image. But I think Meta has been pretty behind. They had their own image model a few years ago that I don't think, you know, people haven't been talking about. It's called Imagine. So we'll see. Maybe a good acquisition target. Something that I've been noticing as I've been getting older in this career is that, and also even just earlier, I worked at a company where our CEOs were under 25.

16:49And that's very famously part of the narrative. It's really interesting, especially as I read more and more headlines, that it's getting harder and harder for young people. Even if they come from a top five school out of a really great CS program to break into tech. and so something that's been like on my mind is it feels like the available window for tech is shrinking from like just for young people to like a smaller and smaller window it almost feels like you've got like 10 15 years where uh you're very you're in very high demand in tech and i just wanted to like chat about that with you guys because we all come from like different tech backgrounds we've all seen different eras of tech different corners of it um but i think it's really interesting.

17:32And so I think maybe we can like start out with like, have you guys been hearing that it's harder for young people to break into tech? And like, what do you think is fueling that? Like, do you buy into this whole like, AI is a better junior engineer than like an actual CS grad? Or do you think that there are other things that are fueling this? I mean, I'm just going to challenge the notion that it's actually harder for people to break into tech. I think it's actually always been quite hard, maybe outside of a few like elite universities. I remember when I was at Social Capital, I was running marketing, but I also had like talent and I would get these like beautiful resumes, like so much more impressive than mine was when I was applying for my first job.

18:13And like they had all the hot internships, they had all the sexy degrees and they were like dying to get into tech. And I think what's different now, a couple things. One is tech is so much more of a like desired destination career wise, right? When I graduated from school, I'll just go ahead and confess in 2007, all of my peers were like trying to get into investment banking. That was sort of the default. And now I actually feel like getting into tech is the new default, the new sexy job. And so there's just so much more interest. And then you combine that with like the headlines around AI and how it's going to take people's jobs.

18:53And like five coding allows like one engineer to do what 10 used to. And so it feels like right now it's more of like a narrative than an actual change. Now in five years, that might be very different. But actually tech has always been kind of insular. Once you're in, you're in and you can maneuver around. But I think it's actually always been pretty hard to to break into tech. And there's just like a different flavor of it today. I'll take, yeah. I, so I'm, I'm a little bit in agreement there. Like, I think the denominator is just getting larger, like, but I also think numerators getting larger too.

19:24So I think, you know, I'll take the sort of like slightly different example. I joined Facebook in 2008 where we had a lot of people who were STEM inclined, maybe graduated with a CS degree and went into investment banking or some sort of like quant, you know, at a hedge fund who were laid off through the recession and like decided to solve a puzzle, like on the Facebook careers site. And then I think there was this thing where like, if you solve the puzzle correctly, like they would fly you out for an interview. So you had all these kids like, yeah, I have a, you know, one or two year, you know, severance package from Bear Stearns and sure, I'll fly out to Palo Alto to maybe think of this job.

20:04And so like, that was, that was like a super interesting time because you had people who were sort of like, all right, yeah, I'll give tech. Tech wasn't a hot thing yet, because I think we were still kind of recovering from the dotcom bust, right? And so you kind of had this like, you know, reluctant sort of, I guess I'm in tech. I mean, I fell ass backwards into tech as well, right? I worked in advertising and sort of like segued into Facebook because they started focusing on brand ads. And so it was a crazy thing, actually a similar story where when I was at Dropbox, we were hiring really quickly on my team.

20:35And the recruiter was just like, you know, we never check the online sort of submissions, right? Like, apply online, like, we never check those, but let's just check just to see. And she pulled out, you know, here's the summary, and here are like the top 50 people. And I think like, I was, I really was stunned, because, you know, as somebody who went to like, a Big Ten school, and like, you know, had a very non-traditional path into tech, I had all of these Ivy League graduates who did two years in investment banking or consulting at the top firms, basically writing me these like four page cover letters on why working on my enterprise marketing team at Dropbox is like their life's goal.

21:15I was like, what? And so like, I think that's when like, you know, we really saw this shift probably similar to when you were at social capital where it's like, oh, this is like the thing that the elite kids do, right? And now, I bet it's more normal, right? There isn't that shock value. It's like, you know, you think about investment banking, consulting, and you think about working at a tech company. I guess my question is, how do we define breaking into tech? Like, would you consider getting an entry level job at Cisco, breaking into tech, right? Not to pick on Cisco, but it's like, is it just Mag7 or super hot late stage AI company?

21:50Or, you know, how do you define that? to a certain degree. I think it's a little bit of like, it's like any, I think tech feels a little bit more democratic than almost any other industry. I don't, I don't know if that's true. I don't know other industries well enough to know if that's true, but like certainly like relative to finance, I think tech is pretty democratic. It's like, if you can get a foot in some type of door, then like, all you have to do is go actually prove that you're valuable. Like when people ask about like, how do you get a job inventor? I'm like, there's a trillion different paths, like you're going to have to find your own way, which is such an annoying fucking answer, but it's so true.

22:25Cause it's not one of those things. Like if you are doing finance, like there's a very clear path for how you get into private equity. And it's kind of about like, can you execute and do you make consistently good bets with that? Like, yeah, you can take like a clearly defined path, but most like you can also come in crazy ways. I think the question is like, do you get the brand or the network that like gets you to your next job? Right? Like either you get that company, that company logo that makes someone take a look at your resume, or you meet enough interesting people that you can network your way to your next job.

22:58So like, I guess, I guess you don't even have to be like, you don't even have to be in the Bay Area, although that helps. Like you can also go get Twitter famous. Like there's a trillion different ways to make it happen, but none of them are easy. Yeah. And I think it's also how you like tell your story about it. So like, let's take that Cisco job example. Sorry, Cisco. is like if you're in you want to be as close to the product or close to the ai part of the business and then okay you you network your way like you said ashley uh into a job that is a stepping stone but if you just go into cisco just for the hell of like joining cisco or okay let's let's insert another company in the similar space then um like you have to be very intentional about which group you join within that.

23:47And knowing that that's going to be your way of saying, hey, this is my exposure into AI, especially if you come from banking with very little or no tech exposure. Something like I had to somewhat do as someone who didn't have tech exposure had media and journalism exposure. And so you have to be intentional about which groups you're kind of navigating knowing that it's a stepping stone for where you want to go next. Switching gears a little bit, what about the people who have been at Cisco for their entire career? I know. Cisco, again, like she said, switch it. Cisco is becoming more relevant now because they're doing AI infrastructure stuff.

24:21I'm just going to put in. There's a real shortage of network engineers. This is a real problem. Long Cisco. Go study network engineering and go work at these companies. Also, Cisco has longevity that most Valley companies could fucking dream of. That's true. I'm not actually shading it. I, in my defense, I did count it as a tech job. Low bar. But switching gears a little bit, I think like the other half of this equation and one that like sparked this conversation, because we talk about how hard it is to break into tech all the time. Like there's nothing revolutionary about that. Although I do think like it's interesting to like really critically examine that.

25:00The other half of this is like, I have worked at no companies where the CEO was more than 15 years older than me. The only company I've worked at that where the CEO is older than me was Facebook and Zuck is exactly like five weeks older than me. So like, literally, that's the only one. The same age as Aaron at Box and the same age as Emily at Glossier. And then Chamath is older than me. So that was my one foray into a more senior. He is. I mean, he looks so fit. But I mean, I think the other half of this. We're keeping that in, Helen. Sorry. Go ahead, Mac. But I think the other half of this is what does when everybody in leadership is older than you are.

25:50And I'm sure some people have experienced the conversation that happens when you see someone who's like really experienced apply, like really experienced and like, to be frank, older apply for a position. And a lot of the conversation ends up being, do they really want to do this role? Like what can they grind? Are they hungry? Yeah. Yeah. What does like long term success? Like what does a, what does career longevity look like in tech, especially if you don't end up as like the CEO, if that's not your dream or goal or desire? I would say, yeah, I've been a hiring manager, you know, across all of my roles and had pretty large teams and had like pretty reasonable, like sort of age diversity.

26:32And there are some roles where I really do value experience and, you know, sort of like the lived experience of having done that specific thing across multiple companies. And so I'm sure that that is true of many functions within a large tech company. The question is, when it's a small tech company, right? Like how much is that true? Because I can see it working. I saw it, you know, firsthand at like 1000, 2000 plus employees, but like when it's just 20 or 50, right. It's like, I think that it's, it's like a pool where every drop in the pool, right. When it's small, it just, it sort of impacts culture and like, you know, there's more surface area.

27:10And so that's the kind of, you know, I, I I'm curious about that. Well, and a lot of people who have like risen in their careers, especially if they've gone from like IC to managing to like managing managers might think they want to join an early startup and they actually don't because it's like very unsexy when you like have to do everything yourself. And I've seen founders make this mistake time and time again. They hire a VP into like their first, you know, they want a marketing leader who can like grow with the company and they hire someone who's just been like away from the work for so long.