Letter #271: Arielle Zuckerberg and Molly O'Shea (2025)
Long Journey Ventures General Partner & Investor at Coatue & Kleiner Perkins and Founder of Sourcery | "The Rizz & Tiz" Winning Founder Recipe
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Arielle Zuckerberg is a General Partner at Long Journey Ventures, a DJ, and the Founder of Lej. Prior to joining Long Journey, Arielle was an investor at Coatue. Before joining Coatue, she was an investor at Kleiner Perkins. She started her career as a product manager at Wildfire Interactive, which was acquired by Google, where she stayed on as a product manager on social ads.
Molly O’Shea is the Founder of Sourcery, a contributor at Pirate Wires, and a Principal at a Family Office. Prior to founding Sourcery, Molly was an investor at Upfront Ventures, New York Life Insurance Company, Trail Mix Ventures, and Global Public Offering Fund. Molly started her career as an entrepreneur, founding BLUE&TUCK when she was a college student.
Today’s letter is the transcript of a conversation between between Arielle and Molly. In this conversation, Arielle and Molly discuss ski lore for VCs, the “Rizz and the Tiz” founder theory, the “vibe” of Long Journey, lessons from Coatue and Kleiner Perkins, being mentored by John Doerr and the principles she learned from him, bad advice VCs give founders, where Long Journey will be in 5-10 years, a framework for follow-on investing, investor price sensitivity and what founders should know about it, valuation narratives, market sentiment and deal flow around AI tools, vertical software, portfolio companies Autopallet and Superpower, operating an excavator, why Long Journey’s office is a house, whether the VC market has gone stale and the advantages of having a personality and being authentic, if the ingredients for being a successful VC has changed, what VCs look for in associates, the importance of the apprenticeship model, building an adult fraternity/sorority, the ideal founder community, whether purpose has dimmed in society, the Wall Street-ification of Silicon Valley, the power of group chats, VCs being value detractive, “Bubbe” wisdom, personal and professional goals, and more.
I hope you enjoy this conversation as much as I did!
[Transcript and any errors are mine.]
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Transcript
Molly O’Shea: Arielle Zuckerberg, welcome to the show.
Arielle Zuckerberg: Thank you so much for having me. It's great to be here.
Molly O’Shea: So I hear you're in Montana. Are you skiing?
Arielle Zuckerberg: Yes, I'm in Montana. I am with family and one of our founders, and I've been skiing a little bit before work every day.
Molly O’Shea: That's fantastic. So the ski lore is real for VCs, huh?
Arielle Zuckerberg: Sigh. Yeah, I know. I hate to be a cliche, but I've been skiing since I was three years old, and it's one of my passions and my biggest hobby, basically.
Molly O’Shea: Well, that's fantastic.
Arielle Zuckerberg: Obsession, really.
Molly O’Shea: Good. I think actually promote hobbies. I think people should be doing sports and being outside, so don't feel bad about it. Embrace it.
Arielle Zuckerberg: Okay. That's great. I am actually a woman of maybe too many hobbies, so I probably need to cut back.
Molly O’Shea: I hear you're also a DJ, so that's another hobby. What else do we have?
Arielle Zuckerberg: Oh, man. I have recently picked up surfing, which I love. Let's see, I have gotten really into romantasy--reading romantasy. During maternity leave in 2024, that was my main source of entertainment while I was nursing, and I've kind of kept that going,
Molly O’Shea: So we have a lot of fun topics to cover today, including lessons from your mentor, John Doerr, the race to $100mn ARR as the new key milestone for early stage companies, how Long Journey prices early stage rounds, and what metrics and signals you're looking for for follow-on financing. But to start, you've become famous for this winning founder theory called the Rizz and the Tiz. Could you just unpack this for us?
Arielle Zuckerberg: Yes, of course. So this is kind of how we think about evaluating founders at Long Journey. Literally, in our investment committee meetings, we talk about whether or not this founder has the right balance of Rizz and Tiz. And what that means--Rizz is charisma, of course, which is, can this person recruit an amazing team? Can they attract downstream funding? Are they going to be a magnetic leader? We believe that neurodivergence is a superpower, and we look for people that live their lives differently, and I think it also represents an intensity and directness. So we want the balance of both, and we think it kind of takes both to be an amazing founder.
*KG Note: “Tiz” is short for “Au[tis]m” in Silicon Valley.
Molly O’Shea: Do you have any examples of the Rizz and the Tiz?
Arielle Zuckerberg: One of our founders doesn't believe in smartphones. He carries a disposable camera and a flip phone. And we have another founder who is obsessed with delegating and also uses special focus glasses sometimes when he works that has like these slits in them so you can only see your computer. So these are kind of some of the examples of people who are living their lives differently. But those people are also incredibly magnetic, and have the Rizz, too.
Molly O’Shea: Well to your point, and to the ethos of Long Journey Ventures, you do invest into the magically weird. And sometimes we don't exactly know what that looks like or feels like, but it seems like that's kind of spot on with the type of founder you guys look for.
Arielle Zuckerberg: Definitely. I mean, I think these things are like a proxy for--the examples I gave are like a proxy for people who live their lives differently, and have the boldness to go after a really magically weird idea.
Molly O’Shea: Speaking of the team, Lee says that Cyan might be the soul of Long Journey, but you're the vibe. So what does that mean? How are you the vibe?
Arielle Zuckerberg: I think tactically, what it means to be the vibe is, I am the Chief Swag Officer, and I'm also making playlists for all of our events. But I take these things very seriously, and I spend perhaps too much time on them. But for example, our most recent swag item--I kind of think about it differently. A lot of people have like the classy logo on like a Patagonia vest or something. I like to think about it more as merch than swag. So I find inspiration from like rock concerts, festivals, sports teams, like merch that you would purchase. So our previous piece of swag was like this unicorn that was on fire with a guitar, and yeah, it was like, skulls and shit. It looks like a rock band shirt.
Molly O’Shea: Merch is super important. I highly support that. So I think that's awesome.
Arielle Zuckerberg: Yeah. I mean, we've had other VCs wear our swag at events.
Molly O’Shea: Okay. That's a positive indicator.
Arielle Zuckerberg: So that's a good indicator. That's a good signal right there.
Molly O’Shea: Absolutely. So I know that you've had more of a traditional background, and now you're more of, I would say, like an artsy, kind of intuitive fund, rather than a rigorous, metrics driven fund. I think you've also been described as the TradVC on the team. You guys are just hilarious. I love you guys. So could you just explain more about the lessons you've learned in your arc from coming from more of the traditional venture capital finance world? I know that you've also been mentored by John Doerr at Kleiner. So could you just walk us through that arc?
Arielle Zuckerberg: Yeah, so Hunter Walk, I think famously said--in the email when I announced that I was joining Long Journey, he was like, Oh, you went from being the weirdest person at Coatue to being the least weird person at Long Journey. So I think that's pretty spot on. But basically, so I--before I even joined VC, I was a recovering product manager. So when I first joined Kleiner, it was a big 180 in my career, so I was just trying to scoop up and be a sponge for as much knowledge as I could. And I remember, like, my first week at Kleiner, working on a deal with John Doerr, and we were doing diligence on a company, and he was in this diligence document at three in the morning. And I was like, This is insane. And I was just so blown away by his work ethic, especially for--he was later stage in his career, and had an insane track record, and I was just blown away by how hard he still hustled. So I really felt that I learned to do diligence the John Doerr Way. And what that means is like turning every stone and just running something to the ground, asking all the questions you can, setting up your questions beforehand and systematically answering all of them, no matter how far you need to go.
Molly O’Shea: What kind of principles other than diligence, have you learned from him? What would you say seriously carries on into how you view companies or view new trends in the venture capital world?
Arielle Zuckerberg: Yeah, I think one of the most important things I learned from him is that it's all about the people. I think even when I was angel investing before joining Kleiner Perkins, I was really enamored by ideas and I was very thesis driven, and I had this view of where I thought the--where the world was going. And John Doerr taught me, like, look to the founders to tell you where the future is going and really focus on the people. And another lesson I learned is like, some VC firms, rather take a more active stance in swapping out CEOs if the company is not performing well. But something I learned is like, it usually doesn't work out. So you're really in with this founder for the long haul, which is why it's so important that you're backing the right people.
Molly O’Shea: Knowing that, and how long it's been since you've been there and been in the industry, there's been so many different tide changes, like it's actually exhausting at this point. But I'm just really curious, from your perspective, in this new intuitive role, learning everything that you've learned, what do you think is, like, absolute trash advice that we as VCs, like, keep on either getting or giving?
Arielle Zuckerberg: Okay, I think that VC Twitter is like, one of the worst places on the internet. So I think--a lot of people are like, Oh, I want to raise my profile. I think I'm gonna just tweet a bunch and build my audience on Twitter. And I mean, I personally think that that's a little overrated. And I try to think about, like, where are the founders?
Molly O’Shea: Yeah, I agree with that. I totally agree with that. It really doesn't carry too much into the real world. So where are you looking for these founders, if they're not on this magical world called Twitter and X?
Arielle Zuckerberg: We are really focused on--at Long Journey, this is the year of deal flow, kind of like the Chinese zodiac, like the year of the dragon, the year the snake. This is the year of the deal flow, at Long Journey. So we've been thinking a lot about this, and we are--we're partnering with this amazing organization called Edge Institute, which runs these like month-long events, like one is called Edge Esmeralda, where young builders gather and talk about the future. So we are just trying to be where the young builders are. So by partnering with things like Edge Institute, working with scouts, working with angels that we really respect, and also have that weird lens that we love. So these are just some of the things that we're pursuing.
Molly O’Shea: So where do you exactly see or anticipate seeing where Long Journey is going to be in the next five to 10 years?
Arielle Zuckerberg: We love early stage, and we'll always be focused on early stage--pre-seed and seed. But we are building our double-down muscle. This is something that we've taken concerted effort--I mean, Lee and Cyan hired me to help with this. And it's something we want to continue to exercise and build over time. We recently did the largest SPV we've ever done. So this is, I think, where we're growing as a firm in the next 5-10 years.
Molly O’Shea: From your time at Kleiner and Coatue, what stage were you working on, and what kind of deals were you looking at?
Arielle Zuckerberg: At Kleiner, it was mostly Series A, and at Coatue, it was Series A and Series B with some seed.
Molly O’Shea: Right, and so you're brought in, you're helping out with a lot of the follow-on capital for Long Journey. So what exactly is your framework there? How do you decide to then double down, like you just said, on these companies, given your experience in, let's say, slightly later stage.
Arielle Zuckerberg: Yeah, we actually have a pretty specific framework that I'm happy to walk you through. So one is, does the company have product market fit? And this actually--for some of our deeper tech companies, we do something more like milestone-based, but generally for most of our companies, it's, Do they have product market fit? Do we see a path to a 10x from here--from the time of doubling down? Does it still feel proprietary? Is there still something weird about it, or do we have some unique perspective or angle on why are we the ones who are doubling down where other people might see the company differently? What information do we have that others don't?
Molly O’Shea: Are there any specific metrics that are associated with that? I know you said, like, 100x.
Arielle Zuckerberg: That one, I think, is more vibes based, I will say. Like, what do we know that others don't know because we've had a longer standing relationship with the company? And, like, what are others missing that we aren't missing? Or vice versa? So that's what I mean by like, how proprietary is this? Then, how de-risked is it? Basically, how much progress has the company made, and in what areas have been de-risked, especially since our previous round? Is this a public company founder? Like, can we see this founder ringing the bell? Is this one of our breakout companies, or is it--would we consider this a flagship deal, or generational company? That's also kind of more vibes based. And then how do we think about downstream investor demand? Because compared to some other funds out there, we're a smaller fund, so we're not going to be able to capitalize the company throughout their entire journey. So what do we think the demand from our downstream peers will be?
Molly O’Shea: How far into follow-on capital do you go? Like, are you going into the Bs, the Cs, the Ds? Is it mostly in the As?
Arielle Zuckerberg: Yeah. So our goal--and this goes back to the 5-10 years, where do you see Long Journey? Our stated goal for this fund is that we don't want to be afraid to put up to $25mn into our best companies. And that's over time. So our initial check, we're leading pre-seed and seed rounds, let's call it with like, a $1-2mn check. So that kind of gives you an idea of how much capital we want to deploy into our top, top companies over time.
Molly O’Shea: How do you think about pricing between those rounds? Like, are you super price sensitive? Is that a factor that comes into follow-on?
Arielle Zuckerberg: Yeah. We are super price sensitive, I would say. And our average entry valuation on the pre-seed and seed side is about $15mn, which I think is quite a bit lower than a lot of other folks out there, and something we're very proud of. I think that also reflects the kind of crazy stuff that we love. But when I joined Long Journey, I wasn't as familiar with fund models. That wasn't a big focus area of mine at Coatue or Kleiner, but Lee immediately got me deep in the weeds of what the main levers are with our fund model. And entry valuation is so, so important. And I learned this pretty early on, like, basically week one at Long Journey. He showed me, like, entering at $25mn versus $15mn, the exit value of the company and how that impacts the fund model is very significant. So it's something that we are always keeping in mind.
Molly O’Shea: Do you think that's something founders should understand more, too? Like, I find there's kind of an often, like a disconnect, because VCs are always seen as like hungry capitalists and are evil, but there is an actual structure behind this, and it's also to protect them in the long term as well. So how do you think about that?
Arielle Zuckerberg: Yeah, we try to explain this to founders when we're kind of like negotiating terms. But yeah, definitely wasn't as much of a concern at Coatue, for example, entry valuation, it didn't--we kind of thought about the model differently at Coatue, and that just wasn't kind of the lever that we were focused on.
Molly O’Shea: Yeah, well, we're seeing those 2021 pricings kind of come full circle. It seems like we might not learn from the past as much as we want to say we are, but these rapid AI super high growth companies are starting to hit that again. I don't know if you saw but someone just leaked that Cursor, who's almost at 100mn ARR in what, like 24 months--something crazy like that--they're pricing their next round around $10bn--don't quote me on that, because we don't know if it's confirmed or anything. Could be just like Twitter fluff. But how do you feel about that kind of narrative coming back into the market?
Arielle Zuckerberg: Well, what I'm seeing is it's made it very difficult for non-AI companies to get funding. When there are companies out there going from 0-100 in 24 months, it kind of resets the bar. And if you are a company that's growing really nicely, when previously you could get an amazing Series A done, I think you're now being compared to these companies that are just blowing up because they're in AI or just because the demand is explosive for some other reason. But, yeah, I think it's just it's made it really difficult for companies who aren't growing in that way to get the attention that they deserve.
Molly O’Shea: So the market is taking a really hard pivot into these extremely efficient and fast growth AI companies. Are you seeing anything like this at the early stages? Like, what is the sentiment from your eyes as an early stage investor? Are you more keen to find companies? Is this the new standard?
Arielle Zuckerberg: I am definitely not expecting every company to follow this trajectory. I think--and I do question--I think a lot of people are really curious and want to try these tools, and I am not 100% sure that a lot of this revenue is going to stick around. I'd be very curious to see. And I think every enterprise out there is thinking about What is my AI strategy? And they're looking, they're probably trying 30,000 tools under the sun or whatever, and seeing what is actually leading to ROI. And I think maybe they'll end up with a couple tools, maybe they won't, but I think everything's trying everything right now, so I think we're probably going to see a big drop off.
Molly O’Shea: Yeah, I feel like with all this like next wave, it's hard to discern how much of that revenue is quality or not, but if you're seeing very large numbers, of course, it's a nice, shiny object, but who knows? Maybe there's a lot of churn that comes with it, but does it--maybe it doesn't even matter in the end, because they are growing that fast, and they will put their stake in the ground as, like, the brand. It's just like something I think about, like, maybe, is there something we're getting wrong here? Maybe that is right. Maybe we should be investing into all of the high flying AI companies, because they are going to be market leaders.
Arielle Zuckerberg: I mean, yeah, it's possible. I actually--I saw an Instagram reel the other day where it was kind of like the millennial and the Gen Zer talking about what tools they use. And the millennial was like Google, and the Gen Zer was like ChatGPT, and then it was like, this, Perplexity, this, Pika. It was like talking about these AI tools being like the new version of like the SaaS companies of yesteryear. So maybe, like, they will just--these newer tools will take over. I think the narrative previously was like, ah, like the incumbents have all the customers already, they'll just add AI into their own tools. But yeah, I think what we could be getting wrong is maybe you kind of have to rethink the entire tool from the ground up to be AI-native, and maybe that matters, versus layering it into your existing product.
Molly O’Shea: Do you expect most of new companies that are coming out to be an AI-native? I'm thinking, how much of what you're seeing in your deal flow is AI-native, and do you want it to be?
Arielle Zuckerberg: Yeah, we are seeing quite a few AI-native. The word that people are using is "agentic," which I hate for some reason.
Molly O’Shea: I know. I don't like it either.
Arielle Zuckerberg: But yeah. So we've invested in a couple vertical software plays that are AI-native, but I think it's mostly about--when we made those investments, it's mostly because the founder has differentiated insight into go to market. So it's not a really--the AI is like the cherry on top. But I do think--look, the chat interface--I think back in like 2017 when this was first--chatbots were first becoming a thing, just the experience wasn't that good. But now I think people... it's, I mean, it's just blown up, and I think you can do so much with the chat interface. So that's one way that we're seeing these like AI-native apps getting tasks done through chat interface.
Molly O’Shea: I want to break down a couple companies within the portfolio. What are some of your most exciting or companies that we should be looking out for right now?
Arielle Zuckerberg: Yeah, so some of the companies I'm most excited about right now, one of them is a company called Autopallet, which is a robotics company, and they are doing case picking for distribution centers, and they are using swarm robotics. So instead of like one or two $3mn robots, they are using a fleet, or swarm, rather, of smaller, cheaper robots that are networked together through software. Another one that has been a high flyer in our portfolio is Superpower, which is like a concierge longevity platform.
Molly O’Shea: Amazing sweatshirts. I got a sweatshirt, incredible. Oh my gosh.
Arielle Zuckerberg: Yes. Merch. It's all about the merch.
Molly O’Shea: The merch is so important.
Arielle Zuckerberg: It's key, it's key. It really is. But I've learned so much from Superpower. I actually learned that one of my biomarkers, lipoprotein A, is something I need to look out for. It's a marker for kind of like a genetic heart disease, so it's actually led me to really look into that and work on that. So I am a huge fan of Superpower. I really love, in our portfolio, we have a company called Bedrock, which is geothermal for commercial real estate. And I am obsessed with the founder, and I love it.
Molly O’Shea: I know that Long Journey is more creative in how you find companies, how you work with founders. So what's the most wild adventure you've gone on to find one of these?
Arielle Zuckerberg: Okay, I think one of the wildest adventures I went on in my investing journey is I operated an excavator. It was freaking awesome. It was one of the most fun--
Molly O’Shea: This is diligence?
Arielle Zuckerberg: Yes, for diligence.
Molly O’Shea: Was it like a marketplace for construction vehicles?
Arielle Zuckerberg: It was software for allowing people to remotely operate construction equipment. And the company is awesome, and yeah, we--I got to first try on a VR headset and operate a real vehicle via VR, and then, in order to compare their software to the real thing, they then let me into an actual excavator, and I had the freaking time of my life. That's like, this is awesome.
Molly O’Shea: So I think Cyan mentioned that you guys have a house, like the house is your office?
Arielle Zuckerberg: Yes.
Molly O’Shea: You have, like, seashells and rocks that you pulled from, like, an adventure at the beach with your founders. It's like, there's a lot of things going on there.
Arielle Zuckerberg: Yeah, we want it to feel like a home. Like the home for the magically weird. That's kind of what we're trying to build. It's more than a VC fund, it's more than a community. When you walk into our space, we really want it to feel like you're coming into our home, and we want you feel comfortable.
Molly O’Shea: Do you think that's important? Like, how much of the VC market has gone stale? Like, and having a personality and authenticity--like, I mean, I'm leading the question already, but, like, I might as well answering it--
Arielle Zuckerberg: I don't know. What's your opinion on this. I have no idea.
Molly O’Shea: Yeah, what's your opinion? I don't know, it's so stale. So yeah, but do you really--I mean, you've come from traditional VC. Do you think it matters? How much of it is nice to have versus an actual draw?
Arielle Zuckerberg: It has to be true to yourself. Coatue has an excellent brand, and their brand kind of is like excellence and prestige, and I think if they tried to do the same thing, it wouldn't feel authentic. But this is who we are, at Long Journey. It has to be what's right for you. I think if you are trying to kind of convey--yeah, it depends on what you're trying to convey and what your values are. Our number one value's Chase the magically weird. I mean, not everyone is trying to chase the magically weird, so they're not gonna have seashells that you've collected on the beach in their office, but I think some people, even if it doesn't feel weird or out there, are still doing it really well, and have great brands, even if that brand is more buttoned up.
Molly O’Shea: That makes--yeah, that makes perfect sense.
Arielle Zuckerberg: It has to be authentic, like you said. And it has to be like aligned--and I think it really stems from who the leadership at the firm is. It's really a reflection of us as people. So a lot of firms are really big now, and it's really hard to lean into that authenticity when you have more and more people, because it becomes like a watered down version of what everyone is standing for.
Molly O’Shea: Yeah, it becomes more institutionalized, and you start to miss the actual early hustle, lean team dynamics.
Arielle Zuckerberg: Yeah, you lose your soul a little bit, for the sake of growth.
Molly O’Shea: It becomes a soulless place. How do you think the ingredients for what a successful VC is have changed?
Arielle Zuckerberg: Yeah, I mean, like I said earlier, the Chinese zodiac? This is the year of the deal flow. So we've been obsessed with who has interesting, proprietary deal flow? And I think if you are able to build a unique network of builders, and create an authentic gathering place for those builders, I think that's one of the most important things. And that's what we are super focused on. So I think that, along with having your own point of view, like being an individual, and not just kind of following what everyone else is doing, and actually--the ability and desire to stick your neck out there and do something different, and having that unique, different deal flow, I think, are the two key things. Otherwise, it's like you're just going to do the same consensus shit that everyone else is doing, and you're going to do it later because you don't have access to that deal flow. So get in early and get in different.
Molly O’Shea: Do you think skills have changed? Like, what do you think skill-wise VCs should be focused on, or what you would want to hire for in different associates?
Arielle Zuckerberg: Yeah, so I think having that unique, different deal flow is sort of table stakes. And then it's either--and it doesn't have to be both, but I think probably both is even better, is you either have to start out with amazing judgment, or just a willingness to learn, and ability to just be really open to feedback and coachable, and being able to shift your judgment, which is not an easy thing to do, but I think that is the key for an associate.
Molly O’Shea: Do you think the apprenticeship model is important? Is that something that--I mean, coming from your experience with John Doerr, like, that's a pretty good apprentice right there. Do you think that's still important?
Arielle Zuckerberg: I think it's super helpful and valuable. I mean, it's definitely--and I think it's what attracts great associates, also. They want to learn from amazing partners. And, yeah, I think it's like a win-win for both. The partners want access to younger founders and builders and operators and, like, youthful energy, frankly. Someone who's gonna--when I was at Kleiner, I was going to like seven events a week, or something. And flying all over the place to random conferences. And, I mean, John Doerr had an insane amount of energy, but he wasn't--actually, he was flying a lot of places. But not everyone is. So, yeah, I think it's advantageous to both the partners and the associates.
Molly O’Shea: Yeah. He has a lot of energy. I recently met him over the Fall at a conference, and I was just surprised he was still going to conferences. It was really impressive. He doesn't need to do that at all.
Arielle Zuckerberg: No. He's a maniac--in the best way.
Molly O’Shea: Yeah, I think the same with Howard Morgan. I see him out all the time. They love it. It's their life.
Arielle Zuckerberg: Yeah. I also worked closely with Eric Feng, who's now an entrepreneur, when I was at Kleiner. And he also--he was incredible and had a ton, a ton of energy.
Molly O’Shea: Yeah, it's like a funny balance of going to lots of events, networking, but then also staying put and being focused and grinding. It's just always going to be a balance.
Arielle Zuckerberg: Yeah. I mean, our associate, Luke, I am loving how many events he's throwing, how many events he's going to. He's always gathering young builders in unique ways. Like he did a Hibachi dinner. It's awesome.
Molly O’Shea: One thing that Lee mentioned about you is that you're building essentially an adult frat and sorority. So is this how you're cultivating community? Like, what does this mean?
Arielle Zuckerberg: That I'm building an adult frat? That's a hilarious way to put it. How do I put this? So I'm the youngest of four. I'm I have three older siblings, so I was always used to a lot of people being around. And as an adult--I don't know--and I'm an extreme extrovert. So I love being around people--I actually don't like not being around people. Like being alone is like, Ugh. I'm like, When can I call my next friend to hang out? So I think I--I always kind of had a roommate when I graduated college, I've had roommates. And then I kind of just never stopped. So even when my husband and I got married, we had a roommate. And then when she moved out, we got two more roommates. And then when they moved out, we actually invited in another family to live with us. So we just always enjoyed having a lot of energy, a lot of different personalities, and living in community. And I think especially my husband's an introvert, and I think it's just a tall ask for your partner to be everything to you. I don't know. People are just relying so much, leaning so much on their partners for literally everything, where if you live in community, you don't have to do that.
Molly O’Shea: What do you think the biggest challenge of that is? I can't imagine--it's always happy go lucky.
Arielle Zuckerberg: No, it's not always happy go luck. You definitely sacrifice--you make sacrifices. But you do it knowing why you're doing it. And when you choose to live in community, sometimes there's a standard of cleanliness, or a standard of clutter, or just--you have to reevaluate what your norms are, because you're kind of averaging out across more people. So yeah, the household isn't always run how exactly we want it to run, but the benefits we get from living in community far outweigh that. So it's just like having the correct expectations and knowing what the trade-offs are going into it. And we've just chosen that we want to make those trade-offs.
Molly O’Shea: Since the office is a house, would you put founders in there and open the doors for building a community within the Long Journey office? I'm just wondering...
Arielle Zuckerberg: So we have a guest room, and we let visiting founders stay in the guest room. But yeah, we're starting to host events there. We're starting to view it as a place to gather our community. As you know, I love music--I'm like, can we turn our basement into a listening party, like a zone for a listening party or listening room? So this is how we're thinking about it.
Molly O’Shea: If you had to design the ideal founder community with like, crazy ideas and constant iteration, what would that look like, and what are the components that make it really vibrant?
Arielle Zuckerberg: I think being the place where people can talk about their boldest ideas and not be afraid of what people think about it is how you build an amazing community for builders where they can really be who they are and--another thing we think about a lot is we think people do their best work when they feel tied to their purpose. And how do you create moments where people feel even more tied to their purpose? Some examples that--we have a Head of Platform, Mike, who is like a freaking wizard at this. But for example, we had a sci-fi movie night. We played Eternal Sunshine of the Spotless Mind, and the theme was core memories, and we had everyone fill out a piece of stationery and write to someone who played a huge role in a core memory. And then had them write down the address, and then we sent those off. And we think things like that help you reconnect, and just really tie into your purpose. And that's what we're trying to create.
Molly O’Shea: Purpose is one thing that Cyan and Lee had mentioned multiple times when we were talking a couple months ago. Why do you think that purpose has kind of dimmed a little bit in society? And why do you think we really need to hone in on it?
Arielle Zuckerberg: That's a great question. I think it's making a resurgence, but I do think maybe--I don't know, even sometimes talking about purpose, I get a little insecure, like, Do I sound really hokey, or do I sound really woo woo? So I think maybe that instinct or insecurity has held people back from talking about it, whereas it's really freaking important and people need to embrace it. And I actually think Gen Z does a really good job of leaning into this, and--yeah, I'm really glad that Cyan has been pounding the pavement talking about this and not being afraid to talk about it, because it's fucking important.
Molly O’Shea: Yeah, yeah. It really is. Because we slowly created a very atheist culture of people chronically online that don't connect with individuals in the real world anymore. And if you're living in that monotonous cycle, you do lose a grasp of like, Oh, if I have access to everything in the world, what's the point? And what is my true meaning? Or what should I believe in? And so it's really awesome that you guys are cultivating such a strong community and brand around you to fuel the next generation of founders to lead with purpose and to have such a passion behind them and pursue these wacky, crazy ideas, or sorry, wild, weird ideas, with the Rizz and the Tiz.
Arielle Zuckerberg: Yeah. One thing I'll add is, there's kind of been this Wall Street-ification of VC. And if I were to think about people on Wall Street talking about purpose, they're probably rolling their eyes, right? This is not something that a lot of investment bankers talk about or think about--at least I assume. Maybe I'm wrong, maybe they're like, really--people have done their Eat, Pray, Love thing and have then gone back to investment banking. I don't know. But yeah, we're trying to kind of be the opposite of that.
Molly O’Shea: I think we feel it more because we're closer to culture. Like tech is very connected to culture, and making culture. Someone said, like, I think their hot take was, Silicon Valley is actually the epicenter of culture, because so much innovation comes out of it, and that shouldn't be overlooked. But if we have the opportunity to continue to create new generations based off of whatever technology they're using, or AI tools--like that is important. Do you have any hot takes for us? What are your hot takes on the venture world?
Arielle Zuckerberg: Okay, this isn't necessarily about the venture world. All the best content is in group chats. It's not in blogs, it's not on Twitter. The most unhinged, best, hottest takes, and interesting info is all on group chats. That's kind of my hot take. And so I am not as--I'm not doomscrolling on Twitter as much, I am just--but I am a part of a lot of really interesting group chats, and that is where I think the most vibrant conversations are happening. I think most value add is dumb, unless it's--something we think about is documentary-level value add. If you're not gonna provide documentary-level value add, then it doesn't matter, and it's all super marginal.
Molly O’Shea: I also believe that value add is is something that VCs should stop marketing. Like, just don't market it. The most like value add VCs can give is commercial value add and opening doors for contracts and customers, honestly. Value add is such a weird marketing angle. I don't know. I think that's a really good one, honestly. You got me fired up.
Arielle Zuckerberg: Yeah. And we also talk about not being value detracting, which some VCs actually are. Like some VCs give bad advice, and are really proactive in a bad way. And we're just--we're trying to not--we're here if you need us, and give us a call, and otherwise we're going to try to stay out of your way as you're building your company. We're not building the company. You are.
Molly O’Shea: Yeah, I think Vinod says like 80-90% of investors actually provide negative value.
Arielle Zuckerberg: Yeah, I've heard that also. Yeah. So we're just trying to be in that 10-20% who aren't.
Molly O’Shea: Alongside purpose, Long Journey Ventures--there is another component that you are known for and like to provide in the ethos of being an investor. Could you share more about that?
Arielle Zuckerberg: Are we talking about being a Bubbe?
Molly O’Shea: Yes. We're talking about being a Bubbe.
Arielle Zuckerberg: Yeah. So this is one of our core values. It's basically our North Star for how we interact with our founders. Or aspirationally how we interact with our founders. Bubbe is a Yiddish word for grandma. So think of your grandma--and what it represents is, your grandma's probably seen some shit, so she's been through a lot. So the roller coaster and ups and downs of the startup journey are not going to phase her, because she's probably been through a war, maybe two. So it's like even-keeled, unfazed by the ups and downs of the startup journey, and then also unconditional love, but tough love. So grandma is going to be direct and tell you how it is, but also she's going to make you a cup of soup when you're sick and she's gonna give you all the hugs and kisses. So that's kind of what that represents. It's the directness, tough love but unconditional love, and being unfazed by the ups and downs of the startup journey. Some investors, if something horrible is happening at the company, they're gonna be like, Oh no, woah is me! But Bubbe knows that everything's gonna be okay, and has that perspective from experience.
Molly O’Shea: We need the wisdom.
Arielle Zuckerberg: Bubbe wisdom. And there are gonna be like, cookies around and shit.
Molly O’Shea: We need cookies. We need wisdom. It's important.
Arielle Zuckerberg: Yeah. So the Long Journey office, we also kind of want it to feel like grandma's house--in a good way. Not like the smell, but, like, a cool grandma.
Molly O’Shea: Yeah, maybe not the smell. So to close out, I just want to end on a good, positive note. What are you most looking forward to this year?
Arielle Zuckerberg: On the personal side, I have a 14 month old, and he has just started taking steps and walking, and it is so beautiful to see--he's my first kid.
Molly O’Shea: Congratulations.
Arielle Zuckerberg: Thank you. And we're also trying to grow our family, so we're trying to have a second kid. So that's on the personal side. And then on the professional side, I think just continue to make awesome, weird investments in founders that are kind of pulling the future forward. And hopefully seeing downstream investors agree with our weird taste.
Molly O’Shea: If it's any indication, I've definitely seen that your portfolio is fantastic, and I have no doubt about that.
Arielle Zuckerberg: Oh, thank you.
Molly O’Shea: Well, thank you so much, Arielle. It was a pleasure. And I hope you have a wonderful time skiing in Montana. I'm very jealous.
Arielle Zuckerberg: Thank you. Thank you. Are you skier?
Molly O’Shea: I snowboard?
Arielle Zuckerberg: Awesome.
Molly O’Shea: Yeah, I hope that's okay. I know there's a rivalry there.
Arielle Zuckerberg: Oh, no. I actually snowboard--I had an interlude of snowboarding when I was about 10.
Molly O’Shea: Love that.
Arielle Zuckerberg: Yeah.
Molly O’Shea: All right, well, go enjoy the slopes. Thank you so much.
Arielle Zuckerberg: Thank you.
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Wrap-up
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