The best career decisions come from the gut

25 Feb 2026 · 45 min · 20 chapters

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In short

Career decisions in the AI era, contrasting “portfolio” careers (consulting/investing across multiple projects) vs “operating” roles (all-in at one company). Also discusses joy as a competitive advantage, AI’s PR problem, and how AI changes work cost equations.

Guest

Ceci Stallmith, Head of Marketing at Lovable. Background: previously at Box (platform shift), Slack (platform marketing), and later ran a GDM consultancy for nearly six years; also did consulting/fractional CMO work across startups (e.g., Twitter, Airtable, Stripe). She has four children (7 and under) and emphasizes flexibility for family and maternity/postpartum choices.

Key claims

follow your gut rather than “lean in”; joy/human connection matter; AI adoption will likely arrive through work tools (SaaS/enterprise) more than consumer apps; AI can raise costs (token costs per employee) and doesn’t replace humans entirely.

Notable examples

Lovable’s hypergrowth; reading from a phone at a keynote (Dario keynote) as a delivery failure; maternity leave comparisons; token-cost-per-employee vs human cost; “real person as luxury service” vs robots.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Welcoming Ceci Stallmith

0:45 to 1:41

The hosts welcome Ceci Stallmith and discuss her admiration for the podcast.

“I've been a long time listener, first time caller.”

Joy as Competitive Advantage

1:41 to 2:30

Discussing a recent statement on joy in the workplace and its impact.

“what did she say the joy is the ultimate competitive advantage or that's at least what we're taking away from it.”

Reflections on Past Work Cultures

2:30 to 4:19

Comparing past work cultures to current expectations around hustle and joy.

“as the ultimate competitive advantage, is truly inspiring and such a great reminder for literally everyone.”

Public Speaking in Tech

4:19 to 5:41

Discussing the challenges of effective public speaking for CEOs and tech leaders.

“I enjoyed the like Claude thinking sort of graphic on top of the aerial shot of her doing like a spin.”

AI's Human Connection Crisis

5:41 to 7:48

Exploring how AI is affecting human connection and communication in leadership.

“Did you guys have any other takes other than, holy crap, what happened here?”

The Future of AI in Business

7:48 to 11:20

Speculating on the integration of AI into business and its implications for workers.

“My biggest addition is, I feel like he crushed it at Davos in particular, which was less of a keynote.”

AI and Work Dynamics

14:00 to 15:24

Discussing how AI impacts the workforce and employee expectations.

“And I think it's just going to become second nature very quickly.”

Exploring Career Shifts

15:24 to 17:52

Introduction to Cece's career journey from consulting to a full-time role.

“Well, we saw a clip from an All In podcast episode.”

The Flexibility of Consulting

17:52 to 21:47

Cece shares insights on how consulting offers flexibility and variety in work.

“Maybe just for some background, I've been lucky to know Cece for well over a decade.”

Motherhood and Career Balance

21:47 to 24:38

Discussing the challenges and choices around maternity leave and career paths.

“and the thing I'll add that it's like the big win is you can drop clients.”
Show all 20 chapters

Navigating Healthcare as Entrepreneurs

24:38 to 27:03

Exploring the complexities of healthcare and maternity as entrepreneurs.

“I really liked the control and flexibility of not feeling like, I think there's a lot of tricky dynamics that come in when you go on a mat leave, depending on the type of company you're at around worrying about your job.”

Going with Your Gut in Career Decisions

27:03 to 28:00

Cece discusses the importance of intuition in making career choices.

“this opportunity with lovable, which is, I think, probably one of the most like coveted sort of operating roles one could have right now.”

Following Your Gut in Career Decisions

28:00 to 29:10

Explore the importance of intuition and personal circumstances in career choices.

“Like there's no way, um, that I'm going to do that.”

The Call of Opportunity: From Break to Full Time

29:10 to 30:44

How unexpected opportunities can arise during career breaks, especially in tech.

“Like I just, I want to just like be here.”

Push vs. Pull Decisions in Career

30:44 to 33:46

Understanding the difference between push and pull career decisions and how they impact our paths.

“And everything shut down and then low interest rates, like venture exploded.”

Cycling Between Operating and Consulting Roles

33:46 to 36:29

Discussing the benefits of alternating between operating and consulting roles for career growth.

“Like the universe is pulling you in some direction and you can like see a path that you weren't even looking for.”

The Shift Back to Operating Roles

36:29 to 42:04

Insights on the trend of experienced investors returning to operating roles in tech.

“Like when you're in an operating role, you have so much depth, but not a lot of breadth, like that company dynamic culture, like it kind of becomes your whole world.”

Insights from a Growing Company

42:04 to 42:52

Gain insights into the dynamics of rapidly growing companies and the importance of being part of their inner workings.

“And I think that being at an LLM is actually a different level of the new class of companies potentially.”

Navigating Career Choices in Venture Capital

42:52 to 43:58

Explore the considerations and reflections on career commitments in the venture capital space.

“Again, with the caveat that if it meets your life stage, if it's actually of interest.”

The Status of Venture Capital

43:58 to 44:27

Discuss the evolving status of venture capital and the mindset required for success in the industry.

“I think a lot of people got into venture because it was high status.”
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Transcript

Automatic transcript. May contain errors.

0:05Ceci Stallmith:Today, we're joined by Ceci Stallmith, Head of Marketing at Lovable. We're going to talk about career decisions and the tension between taking a portfolio approach versus the pull of jumping back into the arena in an operating role in this age of AI. I'm Ashley and Helen is also here this week. 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 I 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.

0:39Ceci Stallmith:Hello. Hi. Oh, hi. Cece, welcome to Great Chat.

0:44Alysa Liu:It is so fun to be here. I feel very honored. I've been a long time listener, first time caller.

0:49Ceci Stallmith:Oh my gosh. It's like the best when you like slide into someone's inbox and you're like, hey, I have a podcast. You come on and

0:56Alysa Liu:They're like, oh, I already listen. I'm in. Oh, the way you did it, I was so humble, Ashley. You're so humble. I was like, yeah, you're really cool. And I've been like following and talking with people about you, saying like, Ashley and Helen need to be the next, the female TBPN. And I'm not making it gender. Ah, there we go. But I legit want to manifest that into the world. I was afraid you were going to say, you have harder hitting questions.

1:15Dario:No, y 'all. You have harder hitting questions.

1:17Alysa Liu:You do love harder hitting questions. And I have been pitching this to people. I'm going to name drop. I've literally brought this up with corporate Natalie because we work with her and been like where's the female tbp at and then i've been like ashley mayor so oh my god yeah oh my god

1:30Ceci Stallmith:killing it yeah i love it i love it you're like the perfect plant on this podcast thank you oh my gosh so much fun stuff to talk about today but can we talk about like i think the thing that has brought joy to all of our timelines first um alissa lu and the winter olympics yeah my gosh

1:47Dario:what did she say the joy is the ultimate competitive advantage or that's at least what we're taking away from it.

1:53Ceci Stallmith:Oh, I don't think she said that. I think that's what I think that the

1:56Dario:discourse has made it crossover and apply to them. And I think that's such a great counter narrative to the 996 hustle, hustle culture of, you know, you just need to grind it out at the office because I felt, you know, we made this comment before that this generation is forgetting that past generations who were sleeping at the office and doing all these things for their startup, they did it because they wanted to. They weren't told that 996 is a corporate policy. And so I don't think that we're going to the space of like, just do what you love. I think that there's many problematic things with that sort of advice.

2:29Dario:But I think joy is, as the ultimate competitive advantage, is truly inspiring and such a great reminder for literally everyone.

2:37Alysa Liu:I could not strongly agree more. This is like where I feel like this actually is very relevant to the topic we're going to get to later, which is following the fun of work. Because work can be fun. And Ashley, I feel like this brings us to our roots at box. I emailed Aaron cold because I saw him give a talk and was like, that guy's just got this energy and I just want to be around it. And it was, there was an infectious joy in that. And that was what like lit my career up.

3:03Ceci Stallmith:So much fun. It was so much fun. The danger is when you do that early in your career, you expect it for the rest of it. And you realize that that is actually like a quite rare to have that. It's funny, Helen, when you were saying like sleeping at the office, Cece, I don't remember what year you joined, but the first box office I was in, there were literal bunk beds in the office and it was like kind of gross. Like I like, as a girl, I tried to stay out of that room. Not, not for any safety reasons, just cause like dudes were sleeping there at night. But like, it wasn't cause of hustle culture.

3:34Ceci Stallmith:There was no like Twitter pressure to be like performing, performing productivity. It was like, people were just so excited to build. And so, So yeah, I think like Alyssa as our like new sort of model for what we all want to achieve. She also really broke through to the timeline because there's this one interview she did where she was just saying like, I love struggling. It makes me feel alive. And that led all of the tech bros to comment on like, oh, like the value of aliveness, which I thought was so interesting. I think I really think AI is really like creating a bit of like an identity crisis for a lot of people.

4:14Ceci Stallmith:And this was like a like being a human is being alive and feeling joy. And it was like sort of like an affirming moment for for the feed.

4:22Dario:We love a good crossover. I enjoyed the like Claude thinking sort of graphic on top of the aerial shot of her doing like a spin. And yeah, there was a lot of this breaking through the timeline in the best way.

4:38Ceci Stallmith:Well, speaking of Claude, it could probably give its CEO some public speaking tips. Helen, this was one you shared in the group chat this week.

4:47Dario:Yeah, I think I was just a little horrified because it was like Dario was speaking at, was it like a, was it like a AI or tech conference in India? Yeah, it was a prime minister.

4:59Ceci Stallmith:I think it was the one where like he and Sam didn't hold hands. Yeah, the non-holo.

5:02Dario:But Dario gave a keynote from what we could see, and he read the entire thing, you know, from his phone. And I think that was just so horrifying for me to watch because like so much of my job, you know, has been like working with CEOs on their public speaking. And I don't know how, I don't know if that communicated that their comms people thought that was okay or that the CEO did not, you know, talk to the comms people. I know they're complete and there's like no way.

5:32Ceci Stallmith:Oh, I do too.

5:33Dario:And she's outstanding. So I was a little bit just like, what happened here? And it was just sort of like the image of it was jarring. But I don't know. Did you guys have any other takes other than, holy crap, what happened here?

5:45Ceci Stallmith:I guess I was sad because I think he's actually not a bad spokesperson. Totally. Yes. I listened to and watched a bunch of his interview with Dwarkesh, the one we were talking about the other week that like inspires me the looks maxing. language. So talk about another crossover. And he was really compelling. Like, I mean, he's like nerdy, but he's articulate. Like as a non-technical person, I was able to like follow that interview, which kind of shocked me a little bit. And so he's capable of, and now of course, like a keynote is a very awkward format. There's a reason why people prefer firesides, right?

6:21Ceci Stallmith:Like my coaching to founders is like almost always try to do like a fireside format unless, you know, you're particularly good at standing up and presenting. And so it's a tough, it's a tough way to do it. But I think like, gosh, reading from the phone, I was, um, I was at an event, uh, last year. Um, and the first lady of California, uh, Jennifer Siebel Newsome was there and she gave a little talk, but she just like read from a binder, like word from forward. And like her intonation was great, but it was, it was just so obvious and you instantly lose your connection with the audience. Like it feels very insincere, even if, you know, it's the most like beautifully crafted speech.

7:04Ceci Stallmith:And so I think it's an example of like, you can't just expect a message to carry, like the delivery really, really matters for these things.

7:11Dario:Well, so this is where I think like Claude, which I've used, you know, to help me with presentations sort of has, have its limits because, you know, there's a way that the talk track like sort of, you know, nests in your brain when you write it versus you give Claude or whatever, you know, AI of choice, a bunch of your notes. And you tell it to like create a presentation for me with a talk track. Cause I know a lot of people are doing this right now. Right. And then it's like, Oh, then you have to memorize. And then you sort of like lose that connection versus like, here's the storyline and here's me putting it into my own words.

7:43Dario:I don't know. That was just a, maybe he used Claude. And that's like, ironically, the ultimate non-sale for using Claude to aid these presentations.

7:54Alysa Liu:My biggest addition is, I feel like he crushed it at Davos in particular, which was less of a keynote. But like those soundbites and the way he showed up was perfectly crafted. So I think that comms team has done a pretty masterful job on the way they're getting him in the world. And this is interesting for a keynote. my question to you too because you're so expert in this is I do feel like these CEOs have this crazy burden on them right now to show up and to make their schedules are insane we're in this extreme moment where everyone's just trying to parse what's going on and so when they're at their breaking point when they're at the point where they're just like oh like an actual keynote how do I deliver that I think what you're pointing out is people want a human connection in a keynote And reading a barely prescripted thing doesn't feel like a human connection anymore.

8:45Alysa Liu:But delivering a keynote properly is a ton of work. The trade-off is a hard one. And how you get your CEO, founder type to get all the way there is not easy. Totally.

8:58Ceci Stallmith:While running a company, right? I think this is tough. And this is where, you know, you have to be protective of their time sometimes. And not to say that this wasn't the right move to show up at this event because it seemed like a truly, like, landmark AI event where all the other players were there. But it's tough. It's really tough. I mean, I remember back to box, like, Aaron got speaking invitations left and right because he was just, like, so good. and we would have to like actually, you know, push him and push ourselves to turn some of those down. There's also a little bit of risk of like overexposure or if you go into some of those scenarios, underprepared.

9:39Ceci Stallmith:There's a Sam Altman soundbite going around right now where he's, he makes actually what is a really interesting point, but unfortunately I think it hits a certain audience really roughly, which is that, oh, people are so focused on how much training it takes to make AI good. But think about all the energy that goes into training a human. It's like 20 years of like meals and caring. And, you know, it's like actually a really interesting point. Like we have this like human level intelligence and intelligence that is, you know, going to supersede human level intelligence. And, you know, we're upset that it that it takes, you know, all of this energy to create.

10:14Ceci Stallmith:But like, yeah, like an individual human is like eating and requires electricity. But like, of course, of course, that doesn't really go over well with a lot of like a lot of people who are like, wait, are you saying we shouldn't have children? Like, are children too expensive?

10:28Dario:I mean, well, people pointed out that Sam is a father, right? I mean, he welcomed a child a year ago or two years ago at this point. And so it was even sort of more strange to remember that.

10:40Ceci Stallmith:He also had the comment where he was like, I don't know how people had babies before chat. Before chat. It's like the same vein. We use Google search. Dude, I get you. I totally get you, but also this isn't going to land well outside of like people in your world. So this is also the challenge of like constantly having these people out there. And I do wonder, like, I mean, this is a whole other discussion. Helen and I talk a lot about like AI's PR problem. If it makes sense to like pull back a little bit and be like a little bit more thoughtful about like the talking points and the messaging and not having these people be so overexposed because things are moving so quickly.

11:20Ceci Stallmith:It's so hard. There are a lot of feelings. There are a lot of different stakeholders. And it's like a very complex communications environment.

11:26Alysa Liu:You could potentially just hire emotional stakeholders, like a person who's actually more the emotional face of the brand, who thinks about how it shows up, who shows up and translates it for the rest of the world. I have felt this. There's a really big divide right now among the early adopters. Like everyone is playing around with open claw to the open claw sort of discourse and the rest people who do use it casually and get some value out of AI but are generally freaked out. I feel like since Opus 4.5, the rift has gotten really big in terms of the very future forward folks and the casual user of AI.

12:01Alysa Liu:And AI has a massive PR problem. And I don't see the companies that are bringing it forward solving it anytime soon. No.

12:10Dario:A standalone great chat episode in the future.

12:12Alysa Liu:Yes.

Read the full transcript

12:13Dario:For sure. But I think the thing that you mentioned, every big technological shift, I think we see this happen more, right? Like the haves and the have-nots or the people who are the early adopters of technology sort of creating their own echo chambers, right? And then sort of leaving everyone behind. And I think where things get really interesting and what feels different about AI is that, you know, you're seeing Fortune 500 companies or enterprises or like these traditionally more slower moving, more reluctant adopters of new technology sort of lean in. Right. And so that's the part where I feel like is the biggest wild card for me on like, how will this all play out?

12:52Dario:Because at the end of the day, it's possible that AI is delivered to you via some sort of like work-related application and not consumer driven, if that makes sense, right? Like I think we think that chat GPT will reach the masses and that's what everybody's touchpoint with AI is. It could possibly be that, you know, Microsoft Office is super AI native and that's how, you know, the masses are reached.

13:21Ceci Stallmith:Helen, I love that you're making the bull case for SaaS. We're just going to rise those stocks back up.

13:27Dario:That's really what this podcast is all about.

13:29Ceci Stallmith:But this is not financial advice. Buy, sell, make your own decision.

13:35Dario:That's right. Trust your multiple sources.

13:38Alysa Liu:It is going to happen in work. That's for sure. I think that it's such an obvious shift. We see crazy organic bottoms of adoption at the biggest companies in the world. And our product, that's not been somewhere we're pushing yet. And it's just happening. So like this is it's undoubtedly happening to work. And I think my question is, will we even be thinking about it as agents? Will we be even thinking about it as I think the terms, everything we're talking about right now is the earliest adopter set of terms and concepts. And I think it's just going to become second nature very quickly. But who's going to do that fastest and most effectively?

14:11Dario:Yeah, no, I'm a big I'm a big SAS stand. But I also think that, yeah, I'm one of those people who thinks that AI will be delivered to the masses via work. because, you know, all the AI, consumer AI attempts that I've seen so far, which is mostly in the gen AI space, right, with video and images, et cetera, et cetera. We have had paintbrushes, paint and paper available to literally everybody since the beginning of time, and only a very small subset became artists. So I think this is just another one of those, like, well, just because people can doesn't mean they will, and work is one of those things where, well, you're instructed to do so and you have to.

14:47Ceci Stallmith:Oh, yeah. It feels existential for businesses. And so they're at least pushing that down to their employees. I mean, we feel, I think the interesting thing about this shift is tech is in the front lines, right? We feel this more than anyone. And but we're also in an earlier phase. And Cece, to your point, like the pressure that tech employees feel to use certain tools, like by the time it gets to the average like Fortune 500 knowledge worker, like is it going to be, oh, you need to be using agents? Oh, you need to be using these chat interfaces? Will it be something else entirely? But that's like what's so fun about this shift.

15:24Ceci Stallmith:Maybe on the topic of work.

15:26Dario:Yeah, let's get into it.

15:27Ceci Stallmith:Well, we saw a clip from an All In podcast episode. Helen, I think you were the one to share it, where Jason Kalkanis was talking about how the token cost per employee is starting to be more expensive than the actual human employee, which is a super interesting. I think AI has been positioned as like, oh, we're super charging humans or we're making work more efficient and less expensive. But actually, it's very, very easy. to ramp your costs way, way up with AI. And so this is also just an interesting, as we think about, you know, the broader debate around what work is human, are humans going to do?

16:07Ceci Stallmith:What work is, you know, AI going to do? There's going to be like a cost equation there too, which is fascinating.

16:13Dario:I think the costs are going to be driven down and that's where you see all of these infrastructure investments. So like, I don't think that the token costs now are what we're going to have forever and ever. If you just look at the marginal sort of increase in efficiency over the past couple of years, we are making huge advances. But it doesn't negate the point that we're making here, which is it's not that AI is 10 or 100 X more efficient than the human employee, so why would anyone bother? It's like, well, if the costs are even remotely similar, you start to value different things. And I think that episode that we had Yoni on, where Yoni said having a having a real person as a like house cleaner is going to be such a luxury flex in the future, right?

16:59Dario:Versus like - Instead of a robot. Instead of a robot, like cleaning your house. And I think maybe you might start to see that as well in luxury businesses. Everything's a services business. So that gets us back to like this theme that we keep bringing up, which is like, you know, in this AI world, are you AI proofing yourself by just being a pleasant human being, like being net additive you know, to the party in whatever form that that takes. And so that was kind of an interesting thing.

17:28Ceci Stallmith:Are you in a list of loo in your office environment?

17:32Dario:You're just emitting joy, an infectious joy. You want to be, you know, you want to bring that person into the office and you want to work with them, even if they're slightly more expensive. Okay.

17:43Ceci Stallmith:Well, this is like the perfect, the perfect transition to talk about our bigger, our bigger topic, which Cece is going to help us explore. Maybe just for some background, I've been lucky to know Cece for well over a decade. We both worked together at Box during a different platform shift, cloud and mobile. And then you led platform marketing at Slack after a brief stint in venture. And then you founded and ran a wildly successful GDM consultancy for nearly six years. And just sort of like from afar, it looks like you had it so down. I was like, oh, she's going to do this forever. She's like, figured it out, like the perfect portfolio career.

18:25Ceci Stallmith:But then you announced you were joining Lovable as head of marketing. And that also sounded like the most obvious, can't miss, oh my gosh, of course you have to do that move. So maybe let's start there. What was your life, your work life pre-Lovable like? And how did you make the decision to go all in on consulting and working across many startups and then back to just one startup. And maybe just for some of our listeners who've been with us for other podcasts, this is like a topic that we are super passionate about at Great Chat. And the way we usually define it is like a portfolio life where you have like multiple revenue streams or multiple projects versus like an operating role where you're like super deep and all in on one company.

19:07Ceci Stallmith:Maybe you do like a little angel investing or something on the side, but like the vast majority of your time, energy and income comes from that. And so Cece, you're like a perfect example of someone who's like gone between those worlds. I have loved going between those worlds.

19:20Alysa Liu:Yes. So my life before my life as a consultant, how I got into it, I would say none of the plans I've made for my career have ever gone as I thought they would. So I actually got into consulting. Amen. That's how life is. And I think that's like the best way. It's more fun that way. I like being on more of an adventure where you're following the breadcrumbs than I'm going on this path. I'm going to make this dream happen. I honestly started consulting after I had been at Slack for four and a half years and my husband had been at Stripe for the same amount of time or even longer actually. And we were like, okay, I'd had two kids.

19:55Alysa Liu:So I'd be lying if I didn't say that I made the choice to get into consulting because I wanted more flexibility. And because I honestly looked at the top. I was at Slack. I was reporting directly to the executive level. And I was like, I don't really want that life. That doesn't look that fun to me. So we discussed it. We were like, one of us wants to be with our child more because we'd had two kids at that point. And I'd been working with kids. And I was like, we're both commuting to the city. This kind of sucks. We don't want to miss out on their young childhood window, which is short. It's really brief.

20:25Alysa Liu:So I thought I'll just dip my toe in the water. He'll stay at Stripe. And my first two clients my first week, this again, just was fortuitous and a gift. We're Twitter and Airtable. And my husband's very good at sales. So he also taught me how to sell, which is part of consulting. I think that like a lot of people try to get into consulting and don't realize that like the sales process is a huge part of being successful. And we just followed the energy and we really did do the different thing. And I think a lot of families that we met in the last five years looked at us like we're a little odd because we decided we're not going to maximize for earning right now.

20:59We're going to maximize for time and we're going to maximize for flexibility.

21:02Alysa Liu:I also, I love variety. So I always worked on platform in my career in some degree. So that means you have developers, you have partners who are really big players like Google, Microsoft, you know, the biggest companies in the world. And then you have customers. So you're always switching your perspective, which I like as a marketer. I like the variety and I loved that in consulting. So the fun of the work of consulting was getting to try lots of clients on, getting to change the type of project you're working on. We were kind of a boutique consultancy too. So I would say that we did lots of different types of work, which I also enjoyed.

21:35Alysa Liu:So I fractional CMO'd. And then I like literally product marketed and launched things for companies. Or I did advising work for a year and a half. So the work really varied in terms of what I did. And I also was really flexible. The other best thing about consulting and the thing I'll add that it's like the big win is you can drop clients. When you're in a full-time role, it's a really big shift to be like, I'm leaving this full-time role and I'm going to the next one. Whereas in consulting, it's like your consulting is the consistent thing. And when you work with a team to the point of it's rare to find a company where there's great energy and where everyone really enjoys working together and the product has fit and the market is fun and it's just like good vibes.

22:13Alysa Liu:What's nice as a consultant is you try people on and you can be like, oh, that's super not for me. Or I love this group and I'm going to come back to that. Like I worked at their table three times. I worked with Twitter from when I started consulting till Elon bought them. And then everyone went away. But so like I had clients that were really long term and then I had clients that I dropped very happily. So it was, that was a really nice variety where you could ramp up, ramp down. I also now have four kids. There are seven and under. And so the consulting life. Yes. We have a lot of children. That's amazing.

22:41Alysa Liu:Yes. And so it was also just a great way to, I would ramp way up right before I'd have a kid and then turn it all the way off for the couple of months that I wanted to postpartum and not have to worry about is my team going to get reorg outside of me or any of those things because I could just take my hands all the way off.

22:57Dario:Oh my gosh, I want to double click on this because this is such a important question that I feel like comes up a lot for women, which is I'm miserable in my job, but they have a great maternity leave process, you know, policy. And so I feel like I should stick it out. And the thing that I say that always blows their mind is like, I have taken maternity leave at a place with 20 weeks of maternity leave. And I've also taken maternity leave, like, you know, at running my own fund and, and, and I can't tell you, yes, it's nice to like continue to have benefits and pay, but there's something else about the, I am truly off in this time is mine.

23:37Dario:And if I feel up for it, I'm going to ramp back up. And if I'm not feeling up for it, I'm not. And so I feel like there are so many people I know that are grappling with that question. So just even hearing you say that is pretty amazing and that you did it both ways, right? You had two kids while working full-time and two.

23:54Ceci Stallmith:You A-B tested, Cece. Exactly. I really did A-B test it. Very on brand.

23:59Dario:Yeah, there are conversations at this level because I think at a high level, it's like, well, how do you get it to all work? And it's like nobody ever does the comparison of the maternity leave in and out of a full-time job. So thank you for the opportunity to discuss that. I will add that I did both with no insurance or like a weird kind of insurance.

24:18Alysa Liu:My husband is a stay-at-home dad. So just to like complete the equation here, my husband left his career and is like fully with our four kids. And like we've invested in my career being the thing we're focused on in terms of like careers that are in a workplace. And we did two pregnancies and postpartum that were like just totally on our own. I really liked the control and flexibility of not feeling like, I think there's a lot of tricky dynamics that come in when you go on a mat leave, depending on the type of company you're at around worrying about your job. I have a friend who's on a mat leave right now and she's at a company where if you don't defend your team, they pretty, and to show its impact, they let it go.

24:56Alysa Liu:Like it's,

24:56Dario:I think that's the default.

24:57Alysa Liu:She's literally like doing calls throughout her mat leave, which is fine. She's fine with it. But like, that was not what I wanted, but I will add like you, the insurance and like all the, if you're in the United States, that is a real factor. And that's something we had to solve for. Like we got quoted$55 ,000 for my birth that I was expected to pay before I delivered. We didn't pay that. I don't want to go

25:19Ceci Stallmith:too far down this rabbit hole, but did you like buy through the state exchange and that was, or were you fully?

25:25Alysa Liu:We did a different thing called a Christian health share. The ultimate cost as I come out to that, never pay what they're asking you to pay you beforehand. And like it covered what the ultimate cost was, which was like half of that cost. But it was one of those, that is the messy factor, I would say, if you're really thinking about it. Yeah, yeah.

25:39Ceci Stallmith:I mean, actually, it's just a real – my husband and I are both, like, entrepreneurial. He has a startup. I have a fund. Neither of us have health insurance through our work. And so that is, like, one of the costs. Like, I love the autonomy of, like, having my own thing and structuring it the way that I want. And same with him. I don't think either of us feel like we could go back, although you never know. But there are definitely some real costs in the logistics. But part of that is just why is our healthcare system so fucked up? That shouldn't be where the friction is.

26:10Alysa Liu:And there are enough of us we should be able to figure out a model to make this work. So maybe this is an action item. Let's grab all the great consultants and portfolio managers and make a solution. But yes. Yeah, great chat group insurance.

26:22Dario:Exactly. Yes, yes. The insurance wing.

26:25Ceci Stallmith:We've had a bunch of business ideas. T.C., I really appreciate your honesty here around how you've thought about things, how you've sort of ramped up and ramped back down, because I think a lot of people feel that if they even step off for a second. I mean, this was one of the big themes of lean in, like don't lean out, lean in. And I think people took that in a very sort of literal and narrow way to be like, I am an executive company and I want to have kids. I have to make sure I'm still getting promoted or still striving. And I think like life is just more fluid than that. And opportunity is more fluid than that.

27:02Ceci Stallmith:And the fact that you sort of architected your life in this way and then had the opportunity, this opportunity with lovable, which is, I think, probably one of the most like coveted sort of operating roles one could have right now. Can you walk us through how that happened?

27:17Alysa Liu:Yeah. I mean, this was, again, we laughed a lot when this whole situation unfolded because because I did feel a little bit like of people who are, you know, climbing the ladder and trying really hard. I've sort of stepped out on purpose. And the fact that this all, again, maybe it was more of an Alyssa Liu moment where it was like, no, when you just really are enjoying it and like having a good time, these things fall in place. Because I started actually at Lovable as a consultant. So I was brought on as a product marketing consultant. and I literally remember my, when I met Anton and this woman who was bringing me on, who's fantastic.

27:54Alysa Liu:Her name's Carrie Lou. She was like, maybe she'll get addicted to the growth and want to join us full time. And I had this like in my head, like scoff at like, like, no, I really like

28:03Ceci Stallmith:my life. Never.

28:04Alysa Liu:Yeah. Like there's no way, um, that I'm going to do that. And also I know what hyper growth is like. I did not know what hyper growth is like in an AI company, but I knew what hypergroup is like, it's such companies. And I was like, it seems different. It is different. I was like, there's no way that I'm going to do that. And the truth is the opportunity just unfolded quite naturally. And I almost feel, and I think this gets a greater piece of maybe what we're talking about and circling around, which is the, it's a little bit of the anti, don't just lean in because everyone's telling you to lean in.

28:36Alysa Liu:What I experienced going through this shift in my career is it's more of a like go with your gut because I think especially maybe there's a useful piece of this as a woman not to over gender but to say like I when I had my children I was like I know that I want to not have to commute really far away from them right now when they're tiny and I'll there there's other religious I just didn't want to deal with I was like I had a gut

28:57Dario:level no it's lovable is lovable fully remote no we're not and we're actually I'm opening the sf office I'm going to be in there multiple times a week I'm going in tomorrow and I like actually

29:05Alysa Liu:really enjoy being around people. So there's a bunch that I love. I just don't have tiny kids anymore. When I was at that stage of like, I don't want to have to deal with this. Like I just, I want to just like be here. And so there's this piece of it, which was like going with my gut into the next piece of work. And with lovable, I feel like it was a gut level opportunity. I also, this is going to maybe sound too much. I felt a level of stewardship where it was like, I felt like I have not been pursuing this. This is not like, I'm not chasing something from an ambition perspective, I like the work.

29:36Alysa Liu:It's generally quite fun. Anton is a joyful, fun person to work with. That's like a really unique opportunity. I'd worked with other founders in this literal space and category. And I was like, I wouldn't want to work with them. I love his energy. I love that he's having fun into the work. And so that was part of the draw. And I also feel like this whole shift is crazy. We're talking about with the, y 'all are covering very well, the PR problem for AI. This is a really large shift for humanity to go through. And so to be offered a position to help shape how people think about all of this work and all of the change that we're absorbing as a species.

30:10Alysa Liu:It's like, I think I actually need to steward that work. It's less I need to go make my career out of it. It's more I need to take it seriously so that we hopefully have a good impact in the world instead of it just being sort of fear, gloom and doom. So that was my...

30:25Dario:Yeah, I love that. No, no, no. I love that. And that's way more inspiring than what I'm about to share, but it definitely resonated because when I left Plaid in late 2019, I was actually taking a career break and I was consulting and fully living the portfolio life. And one of my clients was AngelList. And it was, you know, absolutely not in the works, but like we had COVID a couple of months later, right? And everything shut down and then low interest rates, like venture exploded. And then it was sort of like this calling where it was like, well, I'm fractional, but a couple of things, you know, and I've never shared this before, but it's like, one, it was really exciting to be, you know, on the forefront of, okay, everybody and their mom is starting a fund or everybody's getting into SPVs all of a sudden, because you can take 10 Zoom meetings, you know, in a couple of hours and raise a bunch of money.

31:14Dario:So to be like at the platform where all that was happening felt like there was a straw there. But the other thing was, you know, when Avlo gave me the job or offered me a full-time role, he was like, Angelus has had a remote culture from day one. And I know that it's really important to you because my son's school shut down, that you get to build your hours the way that you want. We've got team members in all different time zones. And so for me, it was like, oh, I could spend my son's waking hours with him at the beach, at the park, whatever, because he's not in school. He was only, I think, six at the time.

31:45Dario:And then at night, I can work around the clock. And so it was just sort of like this perfect arrangement that I felt the calling, but it also worked for my family at the time. And so I feel like these people are always like, oh, yeah, then you ended up at Angelus. And like ending up at Angelus is a big part of my story as to why I decided to become a fund manager. Right. So this whole notion of like nothing is planned, but like you follow your gut and things sort of like they present themselves to you and the answers get a little bit more clearer. So that part really I loved. And I think that what you're doing is not helping people raise more funds.

32:15Dario:It's like shaping AI in our future. And so that's super cool.

32:19Alysa Liu:I totally agree. That feels exactly like the experience I went through, though, too. And part of it was that I'm on calls at 530 in the morning, and it does work a little better with my family for me to be working very early. So I feel you on the setting up for an optimal family life because you are a whole person. You're not this little work automaton. And following where the opportunity leads, it's great. That's the best path.

32:44Ceci Stallmith:Totally. I mean, I don't have as perfect a narrative as Helen going from Angelus to having a fund. But like there is no way I would have started a venture fund if I hadn't been like Angel and Scout investing with friends and like running it like a little fund. And then when I left Glossier and started spending more time on that during my portfolio career phase, when, as Cece, funny enough, I was also consulting with Twitter among other companies. That's awesome. There may have been some overlap there. I guess one framing that I often use is there are like push decisions and pull decisions. And push decisions sometimes are like, oh, I'm like in a role and I'm unhappy, so I need to find a new job.

33:27Ceci Stallmith:Or I think I right now there are a lot of people who are maybe at some companies that are not big players in the AI wave. And they feel a lot of pressure to like find one of those jobs, like one of the coveted operating jobs. So you sort of feel like a pusher, like a, you know, sort of like internal and external demand versus pull. Like the universe is pulling you in some direction and you can like see a path that you weren't even looking for. Like I love those moments and you can't architect them. But I think if you like have enough going on, if you have enough surface area and serendipity, like they will find you.

34:04Ceci Stallmith:And so I love, I think a gut decision is a great way to frame these moments. One thought on the portfolio and operating since we've all done both of those is I'm curious if you guys think there are benefits to cycling between the two because we've all done that as well. So the benefit of not just picking one lane but being an operator and then having more of a portfolio structure and then going back into operating. Cece, maybe this is very fresh for you, but do you feel like that's been to your advantage beyond the benefits to your work-life balance?

34:38Alysa Liu:totally I mean I was getting to the point with consulting where I felt like I either needed to take the work we were doing especially I also had finished having kids I think that was there was part of again the reality to my consulting experience was got to work with really interesting clients like Stripe like the really cool clients high growth super interesting while also being in this very little kid stage and we had wrapped like I was done and I had gotten to the point with my business partner who's amazing, where it was like, okay, do we take, I have more in the tank again. So do we take this to, it's a big agency and we hire people and we make that bet, or do we sort of see what's that next chapter look like?

35:19Alysa Liu:So I definitely like the moving between the two because I think they fuel each other. I also think, again, this comes back to me liking variety and getting a little bored. I had gotten to the point where I was like, okay, I know I could get the set of clients. I know I could sort of knock them down. And I actually, the full, full story for me with getting to lovable was I was sitting there brainstorming with my husband and being like I think if I go back right now to consult with someone it's going to be like cloud code cursor lovable bolder replet and I'd like listed them out and then just got a text like a day later from someone pulling me lovable which was really funny but I realized like I was kind of bored of just I had lots of sass clients that I could work with there's a moment happening right now too in the market that is a little too interesting not to dip your toe into to your point on if you're working in something that's not very AI forward, it's hard not to want to get into that AI opportunity.

36:06Alysa Liu:So I find there's a lot of value switching. And I also find there's a lot of value just because like the type of work, it's fun to flex yourself and like keep those muscles engaged. And then I also, again, I think everything's kind of seasonal and I like to be growing at all times. And I'd gotten to the point with the consulting work that I was doing where I was like, either I need to grow the consulting or I'm going to go back.

36:26Ceci Stallmith:Don't you think cycling through between the two of them also like kind of keeps you honest in a really interesting way. Like when you're in an operating role, you have so much depth, but not a lot of breadth, like that company dynamic culture, like it kind of becomes your whole world. And it's actually very hard to like think outside of that company bubble, but, but you're kept honest by like, you know, you, you touch everything. Um, whereas like consulting, you, you have like a lot of breadth and less depth. So you actually get to see how things work across a bunch of different places and you can sort of challenge assumptions and norms on any one project, but you're not necessarily touching everything.

37:03Ceci Stallmith:So like, you know, depending on the depth of the arrangement, maybe you're giving a lot of advice, but not like pulling it all the way through. And so I've always thought it's kind of a magical combination because like each one sort of keeps you honest from like the last phase, right?

37:17Alysa Liu:Absolutely. There are things that you, like I miss the being external and being able to just like call the thing out so explicitly and being like, it doesn't matter if I just drop a bombs.

37:25Dario:I'm here to drop bombs. It's a very different position to be in. I think even if you are thinking about having a long-term career in investing, possibly, the benefits of going back to operating or maybe even trying operating for the first time are you grow your network around that company and that industry. For example, so much of my angel portfolio is fintech, developer tools, API companies, because I started angel investing when I was at Plaid, right? And so it's not like I set out to be a fintech investor. It's just sort of like where my network was. And so similarly, I think about, you know, if I were to go back to operating and it was at an AI company or, you know, as more of a foundational, horizontal AI company, oh, well, these are the types of people that I would be working alongside.

38:09Dario:And these are the things that I would be learning. And then most likely my deal flow would mirror that, right? And so I think that there are so many benefits from cycling between the two. I think somebody, I was going on a walk with someone the other day and she's a career investor. And she was saying that like one thing that she's realized is that as an investor, you build your network sort of one by one. Every 30 minute meeting is how you're building it. But you don't get scale. And what she was meaning by that was like, OK, well, I was at Facebook, you know, for five years. And during that time, more than 10x its growth.

38:43Dario:Like I just sat there. I didn't go to networking events. I didn't do anything. But because I was a cross-functional, you know, employee and the company was going through hyper growth, like my network was just sort of growing around me without me having to like be deliberate and put like effort towards it. And so I think that if you are lucky to join like a fast growing company, you know, as like sort of like the thing that you cycle away from investing into operating, like that can absolutely benefit you later if you decide to go back to investing.

39:09Ceci Stallmith:I mean, I love the network building adventure. I'm like constantly just amazed by the caliber of people I am meeting on like a daily basis. And like, because I sort of set my, it's like meeting fascinating founders. I'm meeting really brilliant other investors. I'm meeting operators. I'm like learning about things from experts, but there you miss the, like being in the trenches with people, which is where I feel like bonds really deepen. Like I have to be so intentional to take relationships beyond like the transactional or the polite to something that feels like much deeper. And actually, Helen, this is where I feel like the emerging manager community gets really deep because we have so much empathy for each other and how hard it is to build a fund.

39:51Ceci Stallmith:But like, actually, it's really hard to build a deep relationship with a founder you end up passing on, right? Like there are lots of like connections that you make, but they lack depth or longevity, just given the nature of how you're meeting them. And I really like, you know, I think back to Box and maybe just because it was like my first startup job, Like I'm on group chats right now with people who are, you know, like we're still just talking through career stuff or life stuff. And those relationships just go so deep. And I've had such staying power, I think, because we just like really saw some things together and went through some crazy times.

40:29Um, Cece, maybe like last question in this, in this, um, on this theme is, um, I have

40:36Ceci Stallmith:to imagine like, I mean, you are, you are part of a trend, um, uh, of like, you know, people, I mean, there are a lot of people leaving venture roles right now to go back into operating. I think a lot of people who have options and very desirable skill sets who like maybe had found some other way of working or other, like are going back into the arena and taking these like big, big roles at AI companies. And I imagine maybe you get asked for your advice from other people who are considering making the move to whether it's a lovable or an anthropic or an open AI or some of the other ones you mentioned.

41:10Ceci Stallmith:And how would you, like, coach someone on thinking about a decision like this?

41:14Alysa Liu:I mean, I think it comes very much down to the why of what they're doing because a lot of the time people had moved to a different type of role, either because it drew them. I have a lot of friends who I feel like I had a lot of pressure for a minute to like go raise your, like, where's your AngelList SPV? Like, what are you doing on the fun side? Because that was such a big. You don't have a fun. I know. Can you believe it? And honestly, because I had worked in venture for a teeny bit, I was there for a year at Bessemer. And I realized, like, I don't, that's not the kind of work that actually lights me up.

41:44Alysa Liu:So I think that there are a lot of people who tried that on. And I think there's probably a combination of it's not actually the work you wanted to do. and it's just we're going through such an acute shift right now in tech it's hard not to want to cut your teeth at one of these companies again i mentioned the hyper growth the growth is crazy like the growth is we have blown past our january targets in ways that no one would have ever expected at lovable and it's been really interesting being part of something where you're trying to set aggressive targets and you're beating them and you're you kind of understand why and you're just trying to keep up um it's very fun to be in the middle of that so i think that I probably would push people to if there's interest in going back full time, it's worth it for a little bit of time because you get to see the inner workings of this new class of companies.

42:32And I think that being at an LLM is actually a different level of the new class of companies potentially.

42:38Alysa Liu:But it's very fun being at this sort of like we're working together, we're getting insights across everyone. So I think there is a new way of working emerging that's worth being part of. And I do suggest that people do that. Again, with the caveat that if it meets your life stage, if it's actually of interest. Because I think that, I don't know, would you ever go back full time, Ashley? I think that's something I wonder for you.

43:03Ceci Stallmith:Yeah. Well, it's funny because a venture firm is a very long-term commitment. And you're sort of remaking that commitment with each fund that you raise. And so when I've had these moments where I've had to decide, like, am I all in? I play the game of like, what if OpenAI or Anthropic like wanted me to come lead comms? And actually my answer, I mean, I think it would be so fun, but my answer thus far, not that anyone is asking me, by the way, it's just like my little mental exercise has been no, but I think a lot of that was just because I was ready to move on to like a different career chapter.

43:38Ceci Stallmith:And I think I'm lucky in that comms is one of the most like transferable skills to venture because everything is storytelling at the early stage and everything's storytelling when you're building a firm. And so I feel like I haven't had to give up my first career, but now I get to apply it in a very different way and learn some new things. But, but a hundred percent, I mean, that's a real question to be asking. And it's one that, yeah, a lot of fund managers are asking now. I think a lot of people got into venture because it was high status. Now it's kind of like low status compared to like being in the operating roles.

44:08Ceci Stallmith:I think that's actually so healthy. My My hot take is venture should be low status or like lower status.

44:14Dario:It should be a cottage industry of like freaks who really want to do this for the long term.

44:19Ceci Stallmith:Yeah, you got to be a total weirdo and you got to be okay, like not having any real control over outcomes. And being wrong 90 % of the time. Yeah, it's great. Yeah, exactly. Well, thank you so much for joining us. Thank you guys so much.

44:35Dario:Thank you for listening to Great Chat. Have questions for us? make sure to submit them at anothergreatchat.com. See you next week.

From the publisher

This week, we revisit one of our favorite topics: how to decide between operating roles and the portfolio life when it comes to your career. Ceci Stallmith joins us to talk about jumping back into operating as head of marketing at Lovable, and we get radically candid about all the things: stepping off the career ladder, balancing work and parenting, and the power of going with your gut. We also fangirl over Alysa Liu, lament Dario’s recent keynote, and wonder whether employing humans will someday be a luxury flex.

Mercury is back as the headline sponsor for year two of Great Chat. Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

This podcast is edited by Eric Johnson from ⁠LightningPod: https://lightningpod.fm/

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