The tech origin story: No straight lines

0:03This week on Great Chat, all the chatter among founders, employees, and the VCs in between us got us walking down memory lane. How did we get into tech in the first place? Banking? Advertising? Journalists? Our path to tech wasn't linear, and we talk about it all here. But first, this podcast is brought to you by Mercury, the fintech used by over 200 ,000 companies to simplify their finances. We're huge fans of Mercury at Great Chat, and we use it to run this podcast. A few of us are 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.

0:41If 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 out our show notes. Hi, everyone. Hi, ladies. I feel like there's nothing else to talk about but the Coldplay concert. Or it's just plagued my timeline. You know, the problem with AI is it's like really shortened the life cycle of the memes because there's just been such a proliferation that every possible combination has been played through. So wait, have you seen good AI memes?

1:22I've seen some incredible good AI memes. Oh, yeah. Like the Trump and Hillary Clinton one. Oh, gotcha, gotcha. OK, yes, yes. All right. I feel like the just like the IRL memes have been hilarious. Like I've really enjoyed the like the Philly fanatic, the like the sports ones where they're reenacting it like every ballpark. But yeah, it's really brought the nation together. I know it's weird. I don't know if I should feel like I don't know what the right emotion is. But in some of my group chats, there was like a big debate about whether or not the CEO would actually be asked to leave. because it feels like we have moved so far past being sensitive to issues like this that it might just have been um overlooked uh but one thing that was interesting um on this one was like the first 24 hours on twitter the memes were like funny and yes of course at the expense of of the two execs but like they were funny and it felt light-hearted and fine and you're part of this cultural moment yes everyone feels united and then you get on linkedin and it was people writing like 26 paragraph essays on like you know this is why we've got policy and blah blah and you're like whoa whoa whoa you're you're the vibes here are off yeah so it was such a stark contrast between like Twitter and LinkedIn for a very, you know, work sort of thing.

2:53And I saw that the former CEO tweeted last night, he's like, should I go on TMZ? Yeah. Or something like that, where I'm like, you know, these moments where tech becomes part of like the national discourse or like something outside is always just so bizarre to me. But I was like, what TMZ is? Yeah. no my favorite was when people were like was this all a marketing ploy so that people would know what astronomer is because nobody definitely do now yeah i mean i mean looked up the investors that they're series d and they've got an incredible list of investors and i'm sure they've got um takes on it but i don't know i thought the company response was good and everything's been pretty clean there are so many actually the concerning part for me is that there are so many fake statements floating around right that's what i was thinking about was like for for a while even even some of us were we we thought the fake press release was a real one right i i was thinking about how quickly news moves uh this day and age and on top of that you layer on the ai video generated video.

4:02And so going down like a layer deeper, there was that VP of HR who people speculated was at the, at the scene as well. And just imagine if you are that person who was thrusted into this like discourse where she wasn't even, she wasn't even there, but everyone, the country was convinced that she, she was, I, um, I used to oversee our disinfo desk at NBC news. And we have to deal with a lot of doxing. And it's really scary how quickly people find out your personal information. They knew one of our employees where their children's school were. They were showing up to the children's school. So it does bring out some of the dark side of how a regular person can get sucked up into this conversation.

4:54conversation um but yeah it's it's it's been a wild um I don't know 48 hours or three days Helen it's funny that you mentioned like the CEO asking you should go on TNZ I feel like I had the same thought other than like the head of HR is like you should reach out to Alex and call her daddy like this is her this is her 15 moments of fame and she should just write it for as long as he can um well I mean like because I've been thinking about like what are the comeback stories for the CEO. Maybe there is none, but there probably is. I think I texted you guys. It's like, he's going to move to Miami and be like very big into crypto and it'll be fine and nothing happened.

5:34Or like, where do you go from here? So I feel like the redemption arc is where like a call her daddy or something like that would be an interesting sort of. Or like launch a podcast about dating or about in the new age. Oh gosh. I don't know. something so extreme yeah um but yeah we'll see one other thing uh that caught my eye this week was i don't know if you guys saw the ted sarandos who's the co-CEO of netflix talking about the fact that um they used ai in some of their films not surprising for me i think it's inevitable um i it's obviously a space i i cover closely but i don't know if you guys had any thoughts about that well for the uninformed like me like where specifically is it showing up is it like for well video like people acting yeah the way they that he described it was that it was for vfx so a lot of the visual effects that you see which again not surprising getting you know tweaking some additional features here and there but there was a bloomberg article that came out a few days later where it said that Netflix is using RunwayML as a collaborator.

6:51And it also mentioned that Disney might also be starting to look at working with Runway as well. So this goes down a whole debate around which AI models that these film studios are going to use with the ethically trained model providers that are out there. Disney and Universal Pictures, which is part of Comcast, recently sued Mid Journey. So it's this friction between the legacy studios and this rise in new technology that's going to fundamentally change a lot of the ways that the film is made. I wonder what the end game for all of this is. Is it just to lower costs? Is it to deliver more personalized content?

7:37because, you know, part of the appeal of media is that one piece of content brings a lot of people together. And if, you know, the promise of AI is that you can star in your own movie, then it just becomes so siloed. I feel like we'll miss having these water cooler moments or summer blockbusters that everyone is watching, even if it's not personalized just for them. I mean, I personally think it's going to be like a new genre of like ai generated films the same way that like the blumfield low budget horror film is a category of film this would be a category of film that's like ai generated uh content and then just like overall studios are going to use various parts of ai for editing tools but it's i don't think it's going to be like fully generated for the next Titanic or the next Avatar.

8:31I don't agree with that. I think it's going to be less exciting how AI is integrated into film than people might think. Where my head went was whether one of these providers would position themselves as like the one that is, you know, used and trusted because it's not, you know, it's not rife with copyright issues or they're compliant or they're working in partnership with studios because I think a very unsexy but real way to stand out right now is for companies to position themselves as like the compliance first you know sort of like there's a there's what have you heard of Moon Valley yeah yeah we invested in Moon Valley yeah so Moon Valley like I feel like they um they just their positioning is that they're like this right like they're they do it in a copyright safe way and there's a lot of like legal tech that I think also as you can imagine lead lead with that and it's like yeah it helps you break through or you know differentiate yeah it's i mean i think it's a debate of um it can you get the enterprises or the buyers of these products be comfortable with using these ai tools right and so moon valley is well positioned in that legal obviously a big big one um harvey using claude for example yeah because they've used a more safe ethical model right right there's probably also just some like timing delta right because right now ai if you if you're to generate like a full clip it probably can't be more than like 60 seconds like there's no there's no ai model out there that can generate you know even they're expensive tv series of like 30 i don't even know if the capability exists for that continuity to exist for like 30 minutes or or you know two and a half hours for a movie and at the same time you have the actors who are essentially unionized right and so there is there i'm sure there's like a push and pull between like what the contracts say for the actors versus where the studios can work and how quickly the tech is developing that I'm not close enough to, but it'd be really interesting to understand.

10:29But I mean, in some ways, it's probably just the natural evolution because all movie stars really are sort of like handpicked and groomed and the narrative is said. So in many ways, it's sort of like artificially created character. And now you're just taking that one step further for public consumption. one thing I'll say because I got a package um a lot of packages when we came back but as uh I was reading like Prime Day this year did you guys get anything for Prime Day I missed Prime Day I didn't even I don't even they don't I sort of miss Prime Day too it's not even a big thing yeah well I mean I feel like the lead up to it is so long now that you're like wait Prime Day still hasn't happened because you've been just seeing stuff for it um but I thought that it was slow and I thought that in the beginning that there were a bunch of hot takes about how like people see people don't people are turning against amazon and that they're they're you know uh it's not working anymore and then and then all of a sudden it was like nope biggest prime day in history it's like oh so uh let's say the it's a 24 billion dollars in online sales um over four days that's just in the u.s too which is insane to think about angela what else uh what else are you're watching my brother got engaged recently and he he he and his fiance had this discussion of whether she wanted like a larger diamond that was lab grown or one that was I don't know if the term is real because technically they're called natural diamonds natural thank you I was like the lab grown diamonds are also real um oh my god i'm obsessed with this yes yes and she was like give me the bigger give me the bigger rock and like honestly it is amazing how much cheaper it is like a like a a tenth of the cost um and so i've just been browsing like religiously looking for it's our 10 year next year so i've been i've been preparing zach for the size of diamond that I'm going to be for a harder time.

12:28Oh my gosh. Wait, so you have a natural one now and now you're like, and since that, since I'm open to, okay, I am tracking this so carefully because I think that sentiment is changing, like for sure. Like, can you imagine what the discussion is in the halls of De Beers or Tiffany's or, or, you know, wherever, because they really have to preserve their, you know, luxury sort of status. And, um, I know, I think that that's kind of the last leg it has to stand on because there's really nothing else it's it's brand um and like what we have already assigned the meaning to we've already assigned meaning to a natural diamond which which i think behind that campaign was debier's uh the diamonds are forever was a marketing campaign that debier's started and they kind of segment segmented diamonds as an engagement ring uh stone totally I mean, I think if you just track the stats, like, you know, lab grown diamonds are just, they're growing in market share every year.

13:27And I think it'll look, it'll continue in this trend for a long time. So we'll see. I mean, I am very pro natural diamond when it's like vintage and I like people sort of, you know, I think that's very romantic and cool too. But yeah, I'm pretty much on the camp, lab grown diamond camp. I mean, I want those Kris Jenner like diamond earrings. Oh, nice. I'd never afford them if they were natural. So the lab-grown path allows me to - Would you just wear them to work? Would you just wear them on the podcast? Just think, hey, guys. That's a good question. When would I ever wear them? That's a good question.

14:02I don't know. Nice. Well, I know we survived the A block without mentioning Windsurf Cursor or crazy AI salaries. I would be so proud. But it did get us thinking about just, you know, the why behind why a lot of these founders go into technology or and then that transitioned us into a conversation around how did we all get into tech? And I think none of us had a really linear path. Actually, I learned this in this process of even this week that, Helen, that you started in advertising. And so maybe this week we talk a little bit about, you know, how we got into tech and how we transitioned and some of the various life cycles we had before it.

14:52Yeah, and why we stay too, right? Because I think, you know, we are excited to be here, but we're also, you know, there's a lot that's changed, I think, especially over the last decade plus. So excited to talk about that too. Yeah. So, um, Helen, you, you started in advertising, um, you worked at a traditional advertising agency and, and then the Helen I know is the one who is super early in Facebook. And how was that transition and how did you get into that? Yeah. So a question I get is like, Oh, how did you know you wanted a career in tech? What got you into tech marketing? And I was like, if I'm being honest, I wanted to work in advertising forever.

15:36I was like very intentional about it. Um, uh, like straight out of school, I joined like a big advertising agency, YNR. Um, and you know, I moved from another shop. I got to do a Superbowl commercial, which is like the Holy grail of advertising. And I loved it. I thought I'd do that forever. And like advertising is definitely one of those careers where it's like a slope like this. You make nothing in the beginning and you have to pay your dues for like a decade. And then, And, you know, then you like start making a lot of money. And so I was like on that path. And then in 2008, I will remember this day forever.

16:10It was like June 24th or something like that. And I remember it so vividly because it was like Chipotle, buy one, get one day or something. But you had to do it. I did not expect that you would say that. Yes, exactly. I'm like, I want this to be visual. But like, but there was a catch. Like you had to show up dressed as a burrito. so me and like three or four other you know please find the photo we are as a burrito you take a lot of tinfoil in your like micro kitchen of your office and grab each other in tinfoil and we like went and got our free burritos and we like get up on the elevator we're on the top floor and it's like a movie scene where everybody is like typing in their passwords to like unlock their computers and nobody can get in and they're just looking at each other like hey are you locked into your computer too?

17:00And like my desk was at the very, very far end of the, um, the office. And it was like a slow motion, sort of like me getting to my desk to type in my password to see if I have been laid off. Cause that was clearly while you're wrapped in tinfoil and holding a burrito. Yes. And so I sit down, I was not laid off and it was really only because I was working on like a very, like a revenue generating account that was fine. Um, but we had some, we had some very big financial institutions and they had all fallen and I think they had cut their marketing budget so it was just responsible for the agency to like pretty much let go of 75 % of staff so I was 25 and were you in New York at the time or I was in San Francisco yeah I was 25 and it was bizarre and I think that you know you like you hear about these things right you I I remember the the dot-com bus but I was in college and but this was like oh is this happening like right now.

17:55And that day I went home and my roommate had a, just a friend from college who was over, who was like very early at Facebook. And he was like, Hey, do you want to work at Facebook? Because we're hiring people who have advertising experience. And it was just like this perfect storm of, of whatever. And he's like, Sheryl Sandberg had just joined. And she, her whole story was about how she wanted to do brand advertising at Google but never really got the chance and at Facebook she believes that Facebook will be the largest audience and therefore brand dollars will move to Facebook and there's an opportunity to present a product to the market that is the equivalent of television ads and television ads were all I did and so I remember going to my room and like printing my resume like printing it and handing it to him and he like handed it to the hiring manager the next day and like I got a call that is how and then yeah of course I have a job later but like that was unexpected a crazy confluence of a bunch of things that happened like within a week um and yeah so you just never know and so and of course like I've been in tech ever since and that was a very long time ago but it was and how was it like how was it joining Facebook at that time because you've you've only worked in an advertising agency, very different structure.

19:17And then, well, so Asian parents, my parents were like, Facebook, um, why not Google? Um, or something, you know, so it was very, it felt very risky and crazy. And I think this is what is hard to imagine, but you know, like at the time it didn't feel like I was going to go join a rocket ship and people around me were not impressed that I was going to go join Facebook. Like even at the ad agency, I remember when I said I was leaving, they were like, are you crazy? You were saved. Like we spared you. We gave you a promotion in title only. And, and, and like, it felt, it didn't feel like I'm joining this, you know, inevitable thing.

19:53But remember at the time we didn't have Twitter. Oh, we did, but it wasn't what it is now. And we didn't have all of this coverage to validate that like startups were the next big thing or that this was obvious. And, um, so yeah, I joined, it was like, I think low 700s or high 600s number of employees. So it was like, you know, it wasn't super small. I think it was series D and we had healthcare or health benefits and basic things like that. But it was definitely scrappy and the business side was very underdeveloped. And I don't know, it was awesome, but I had no basis of comparison. And I think the thing that I always say is like when that's your first foray into a venture-backed startup, that's a very high bar.

20:34And if Zuck is your first example of a founder, again, very high bar. And, you know, but that's, that's sort of guided the rest of my, my career in tech. I kept looking for that. And, you know, now I can say, I think that was a generational company. And there was something very special about Facebook, especially at that time that you just can't appreciate when you don't know anything else. Right. Yeah. I also wonder if like that, that mentality back in that era has shifted now because of, you know, you see the things that happen at windsurf at the the deals that happen and you're starting to value first of all you're you feel like everything is a rocket ship or everything for the first six months feels like a rocket ship and so people are it feels more or less loyal to these companies maybe or i wonder what the like barometer people are are measuring against and and maybe like i don't know, Helen, like if there was something that you learned from Facebook that you see parallel now?

21:38Oh, that's a good question. You know, I think that at the time, if you had asked every single person at Facebook when I joined around the time that I joined, if they thought that they would work at Facebook, I don't think a single per or a startup, I don't think a single person would have said yes. I think maybe actually I take that back. A bunch of ad salespeople who were like early at Yahoo would have said yes. They were like, oh yeah, that was awesome. I want to do this again. right um but i think everyone else sort of fell into it and there wasn't this discourse of like you know how joining a startup can be a very reasonable you know um career path or a way to give for some people you know get generational wealth like i don't think that that was something that people thought about and so for the time remember it was like great financial crisis we got a lot of people who like got laid off from bear you know bear stearns and lehman brothers who were just like uh i can code sure i'll join this social media company right like it was a lot of people who whose plans went sideways who joined and i think that that was um pretty unique because now i think that when people join a startup they're like i've always wanted to work at a startup like i watch the social network i've been reading tech crunch since i was 10 you know like it's like i I think it's become easier to sort of understand what this could look like as a career path and a lot of people plan for it.

23:00I think, Helen, like it's crazy to think of a time when Facebook didn't have an advertising business, you know, sort of like now, like$150 billion later. But I think what was interesting about the wave of startups that we saw over the past 15 years was the actual like the business function had a lot of value to add. Right. Like building out the advertising business, people with an advertising background, like figuring out that model was really important. And I think people were compensated for that. Right. Sally's Sally's favorite Nikesh was like the highest person paid at Google. And he was a business.

23:37He was a business guy. But I think what's different about this AI wave, which not to bring it back to Windsurf and the events that have just happened is I think most of the employees that were left behind at Windsurf if we're on the business side, because that's just less of a focus. Like monetization is actually more clear in some ways. Like these startups are generating money way earlier and at way higher scale than in previous cycles. And there's so much more of the values ascribed to the technical talent. So I'm curious as we go through the next five years, how that influences people like ourselves who don't come from that technical background in terms of thinking about joining startup or their place in the tech.

24:21With Windsurf, what I was trying to figure out was like, you know, they're saying business functions, but that could mean so many things. Right. And like, but if it's sales to me, that just makes sense. I mean, we had salespeople even from the very early days making a million, like a million dollars a year because they were just killing it. Right. Like Facebook was doing a really great job with ads and that was cash that they could, you know, invest in Bitcoin or whatever, and then do better than everyone else who was getting equity. So, I don't know. I'm kind of torn on the whole, like leaving the business functions behind.

24:52I think that is for some roles in particular, like, like sales, something that you like sign up for immediately, but not sure. Angela. And I also learned this week that you grew up in Silicon Valley, which I thought I knew all about you and I'm learning something new every day. And you had a more, I would say traditional venture path, but how did you navigate that? And I assume if you joined around the financial crisis as well, right? And so like, how did that shape your thinking? Helen, it's interesting to hear your story about what happened in the, like in your advertising company. I feel like millennials of our, like of our age cohort have all of this like generational trauma and the great financial crisis.

25:35And I feel like from growing up in Silicon Valley, the dot com bust was one as well, because things were like really booming. And then all of a sudden things fell apart and very tangible ways for like average rank and file engineers who had, you know, taking out credit card loans to really exercise their options, which are now totally underwater. Or we've been paying taxes on equity that was now totally worthless. And you see some of those dynamics happen again. Again, I was talking to a friend who works at a very highly valued private company, and he was saying like he is paying to work at this company because the taxes he's paying on his equity are more than he's getting paid in cash.

26:16And so like the hope is that the equity is worth something because you're negative cash flow today. And it's interesting to see those same signals. But the human impact was really real for the people that lived here. And then to go through that again, just a few years later in the financial industry, I think just puts you in a little bit of a different mindset. But my version of Helen's story is I think this must have been six weeks or eight weeks after we started at Goldman in the summer of 2008. So this was already after the fall of Bear Stearns and right when Lehman was collapsing. They called all of the first year analysts who were just a few months out of college into a town hall meeting and then basically summarily cut a quarter of the people or move them to different orgs.

27:08And these are very high achieving, high functioning people who gave up other options to be here. And so it was very jarring to see people at the start of their career think that they're on one trajectory and get moved to another. Most of those people are very smart and talented and figured it all out. But it was just very crazy to see. And it gives me a lot of empathy for what employees at a lot of tech companies must be feeling now with the, I think, Sally, you called it the rug pull of what's been happening around corporate change. And so I got pulled back because one of the staffers I worked with at Goldman had joined SoftBank and he was looking to hire someone on his team.

27:50And so, like, I think we often say the world is small and your journeys are long. So 10 years later, we were reunited at SoftBank. Cool. Because in between you did private equity, but you weren't focusing on tech. I did private equity. I focused on a bunch of different industries. It worked on cruise lines. It worked on hospitals. But I actually did a little bit of a deep dive on Web 1.0 companies. and it's funny to think about it. I always laugh because we looked at eHarmony and I remember we were going through our investment committee decision and we were talking about online dating and what online dating was.

28:34And this is when there weren't really many free options and you had to answer all these questions. And people were just like, oh, but why would people want to date online? And it was this foreign concept. But 10 years later, it's sort of the de facto way that people are dating. So it's interesting to see over even just the journey in my own career, how quickly tech trends can change. Sally, how'd you get into tech? Well, actually, the financial crisis is how I got into tech. Before then, I started a career in journalism. I always thought that I wanted to be a war correspondent, like many naive young journalists that want to go into the industry.

29:13And so is that what Christiane Amanpour did? exactly that's the person i thought of as well i picture sally like in like some golf you know sort of yeah yes location it's like such a like you look amazing you look so good yes yes but you know when the reality settles in is when you realize that oh in your young 20s you're gonna have to move to syria or the middle east somewhere and you know spend your majority of your 20s there And then it was, you know, I did intern for Anderson Cooper. I interned at MSNBC. I did actually start a major or double major in poli sci and journalism because I thought this was the career I wanted to take.

29:57And then I was in college when financial crisis hit. And I was like, what the hell is this? I was living in New York City at the time. Majority of my friends were in finance. And I didn't know what an equity or a stock or a bond was at the time. but then somehow got an internship after some prep at CNBC and then joined Bloomberg. I joined Bloomberg right out of college and then worked at CNBC for a decade. And so as part of my coverage, I did more of macro. I started by covering IMF World Bank and then more banks and then M &A, and that's how I got into tech. at a time where we were starting to cover more IPOs.

30:41And we weren't doing a ton of private market coverage at the time. One of the big IPOs we covered was Alibaba. And before it went public, obviously it was a huge, you know, massive company out in China. Before then, we hadn't really spoken about Alibaba before. And so Jack Ma and Joe Tsai, who the two executives, senior executives, came into the office. We had to do this whole explainer. And then we pitched this concept of, hey, we should cover private companies a little bit sooner because, you know, you don't want to just introduce a whole new, you know, company vertical days before the IPO. So again, this like sounds so obvious now, but at the time we were so focused on public markets and stock picking.

31:28And I think like how people, you know, what they get out of CNBC or various business news has obviously shifted because of the amount of information that are out there. And so that's how I got into tech. And then I pitched this show idea called, now it's called Squawk Alley, which is a tech show on the network. Again, not a novel idea now, but at the time having a tech dedicated show was an interesting pitch. Then I moved to San Francisco in 2017, right around when Airbnb and Uber and all these companies were going public and I wanted to be at the center of the action. I didn't know a ton of people and then expanded my network there.

32:15I will say, though, transitioning from an editorial side of covering tech and exposure to tech and then actually going into an operating role in tech was definitely a more challenging journey than I thought. So I think like a lot of people in journalism or, you know, even now, especially now, actually, because unfortunately, the size of the industry is getting smaller. So there's a lot of layoffs. And so a lot of my colleagues are looking to transition into tech. And so have asked me for various advice. And frankly, it's not very a linear path in that either. You can't just transition from an editorial role to like, let's say, a BD role, even though a lot of it is around storytelling and, of course, dealmaking.

32:59But I did actually end up joining United Masters, which is a music tech platform that's backed by Andreessen because of my relationship that I had, or I knew some of the partners there during my CNBC days. But it wasn't a very easy transition. We spoke almost a year before I joined. Um, and then I, you know, I was overseeing BD and partnerships and then, um, took on corp dev role where I got exposure to, um, more of the deal making side of things, which again, I, I, um, I had no, no experience. So I kind of learned it on the job. Um, I think one important thing is just like framing, um, the story of what you've learned.

33:43Um, and we can definitely get into that as, as another topic, but yeah, definitely not linear path and definitely not an easy transition as I think people expect from journalism to tech and we see it in various forms. That's super interesting. Like I, so I taught a class for Northwestern School of Journalism. Like so Medill has like a West Coast campus and there's this class that I called careers in tech, right? Basically they want to take a bunch of journalism majors in their both their undergraduate and master's programs and like kind of prepare them that a lot of the jobs that you thought that you might be graduating into are no longer exist right it was very smart of them to do this and so a lot of what I had to sort of talk about was like how do you transfer that storytelling skill but also like one that when you were talking Sally I was reminded of was I think when you're a journalist, you are right with the subject, right?

34:44You are exposed. The names that you were just sharing like are incredible. And every day you're like meeting with fortune 500 executives and like heads of state and like, you know, all these things. And then if you think about like what a content strategy role is buried within a marketing team of Google, right? It's like you have a very different day to day and the people that you interact with on a day to day basis are not heads of state, right? So it's just sort of, I think that I did not realize that transition on like kind of imagining what your day to day and who you are interacting with and who you're talking to was turned out to be like one of the biggest sort of like leaps for a lot of a lot of these folks.