Pod Insights Sourcery Arielle Zuckerberg, Winning Founder Recipe: The Rizz & Tiz About this episode Behind the Magically Weird: Arielle Zuckerberg on Long Journey Ventures, Unique founders, and Purpose-Driven Investing
Molly O'Shea speaks with Arielle Zuckerberg, diving into her journey at Long Journey Ventures, discussing her unique investment philosophy and the importance of purpose-driven investing. From her hobbies like skiing and DJing to the critical lessons learned from legendary mentor John Doerr, Arielle shares how she evaluates founders using the 'Rizz and Tiz' theory. We uncover Long Journey's creative diligence adventures, the value of unusual startup ideas, and how Long Journey Ventures fosters a unique community for 'magically weird' founders. Whether you're an investor or startup enthusiast, gain insights into navigating the fast-changing VC landscape and focusing on the human element of investing.
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TIMESTAMPS:
0:00 - Welcome Arielle To Sourcery!
01:22 - The Rizz and the Tiz Theory
05:31 - Lessons from John Doerr
08:49 - VC Twitter and Deal Flow
17:01 - $100M ARR AI Companies
22:05 - Portfolio Companies: Superpower, Autopallet
31:45 - Building a Vibrant Founder Community
36:43 - The Role of Purpose
39:52 - Hot Takes on Venture Capital
42:21 - The "Bubbe" Philosophy
44:19 - Looking Forward: Personal and Professional Goals
#podcast #investing #technology #venturecapital #entrepreneur #startup #siliconvalley
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Molly O'Shea? You've become famous for this winning founder theory called the riz and the tiz.
0:05 Speaker 01 We believe that neurodivergence is a superpower. We want it to feel like the home for the magically weird. VC Twitter is like one of the worst places on the internet.
0:17 Molly O'Shea? Yeah, I agree with that. What are some of your most exciting or companies that we should be looking out for right now?
0:23 Speaker 01 One of our founders doesn't believe in smartphones. He carries a disposable camera and a flip phone.
0:29 Molly O'Shea? You're building an adult frat and sorority. So is this like how you're cultivating communities? Like, what does this mean?
0:39 Molly O'Shea? Ariel Zuckerberg, welcome to the show.
0:43 Speaker 01 Thank you so much for having me. It's great to be here.
0:46 Molly O'Shea? So I hear you're in Montana. Are you skiing?
0:49 Speaker 01 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.
0:57 Molly O'Shea? It's fantastic. So the ski lore is real for VCs, huh?
1:02 Speaker 01 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.
1:13 Molly O'Shea? Well, that's fantastic.
1:14 Speaker 01 Really.
1:16 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.
1:25 Speaker 01 That's great. I am actually a woman of maybe too many hobbies, so I probably need to cut back.
1:31 Molly O'Shea? I hear you're also a DJ, so that's another hobby. What else do we have?
1:36 Speaker 01 Oh, man. I have recently picked up surfing.
1:40 Molly O'Shea? Okay.
1:40 Speaker 01 Which I love. Let's see, I have gotten really into romanticy, reading romanticy.
1:49 Speaker 01 Yeah, during maternity leave in 2024, that was my main source of entertainment while I was nursing. So I've kind of kept that going.
2:00 Molly O'Shea? So we have a lot of fun topics to cover today, including lessons from your mentor, John Doerr, the race to $100 million ARR as the new key milestone for early-stage companies, how LongJourney 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 riz and the tiz." Could you just unpack this for us?
2:27 Speaker 01 Yes, of course. So this is kind of how we think about evaluating founders at LongJourney. Literally, in our investment committee meetings, we talk about whether or not this founder has the right balance of riz and tiz. And what that means, riz 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
3:11 Speaker 01 takes both to be an amazing founder.
3:14 Molly O'Shea? Do you have any examples of the riz and the tiz?
3:17 Speaker 01 One of our founders doesn't believe in smartphones. He carries a disposable camera and a flip phone.
3:23 Molly O'Shea? Wow.
3:23 Speaker 01 Yeah. 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 they have the riz, too.
3:49 Molly O'Shea? Well, to your point and to the ethos of LongJourney 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.
4:07 Speaker 01 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 are, you know, have the boldness to go after a really magically weird idea.
4:22 Molly O'Shea? Speaking of the team, so 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?
4:35 Speaker 01 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, you know, the classy logo and 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
5:19 Speaker 01 that was on fire with a guitar and yeah, it was like skulls and shit. It was, it looks like a rock band shirt.
5:30 Molly O'Shea? Merch is super important. I highly support that. So I think that's awesome.
5:35 Speaker 01 Yeah. I mean, we've had other VCs wear our swag at events.
5:40 Molly O'Shea? Okay, that's a positive indicator. So that's working.
5:42 Speaker 01 Indicator. That's a good signal right there.
5:44 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.
6:01 Molly O'Shea? I think you've also been described as the trad VC on the team.
6:06 Molly O'Shea? You guys are just hilarious. I love you guys.
6:09 Molly O'Shea? 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?
6:23 Speaker 01 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 Co2 to being the least weird person at Long Journey.
6:37 Speaker 01 I think that's pretty spot on. But basically, so before I even joined VC, I was a recovering product manager. So I really, 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, you know, he was later stage in his career and had an insane track record.
7:22 Speaker 01 And I was just blown away by how hard he still hustled. So I really felt that I like 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, you know, how far you need to go.
7:49 Molly O'Shea? What kind of principles other than diligence have you learned from him? Like, what would you say like seriously carries on into how you view companies or view new trends in the venture capital world?
8:01 Speaker 01 Yeah, I think one of the most important things I learned from him is that it's all about the people. I think even, you know, when I was angel investing before joining Kleiner Perkins, I was really enamored by ideas and I was very thesis driven. And, you know, 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, you know, some company, some VC firms, rather, you know, take a more active stance in swapping out CEOs if the company is not performing well.
8:44 Speaker 01 But something I learned is like, that's usually, it usually doesn't work out. So, you know, you're really in with this founder for the long haul. And it, which is why it's so important that you're backing the right people.
8:58 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?
9:27 Speaker 01 Okay, I think that VC Twitter is like one of the worst places on the internet. So I think, you know, a lot of people are like, oh, I want to like raise my profile. And I think I'm going to like just tweet a bunch and build my audience on Twitter. And I, I mean, I personally think that that's a little overrated. And I try to think about like, where are the founders?
9:52 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?
10:06 Speaker 01 Um, we are really focused on, this is at Long Journey, this is the year of deal flow. Kind of like, you know, the Chinese zodiac, like the year of the dragon, the year of the snake. This is the year of the deal flow at Long Journey. But 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.
10:32 Speaker 01 Events like one is called Edge Esmeralda where 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.
10:57 Molly O'Shea? So where do you exactly see or anticipate seeing where a long journey is going to be in the next five to 10 years?
11:06 Speaker 01 We love early stage and will always be focused on early stage, pre-seed and seed. But we are building our double down muscle. This is something that we're, we've taken concerted effort. I mean, Lee and Cyan hired me to help with this. And, you know, 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, you know, I think where we're growing as a firm in the next, you know, call it five to 10 years.
11:38 Molly O'Shea? From your time at Kleiner and Co2, what stage were you working on and what kind of deals were you looking at?
11:45 Speaker 01 At Kleiner is mostly Series A and at Co2, it was Series A and Series B with some seed.
11:51 Molly O'Shea? Right. And so you're, you're brought in, you're helping out with a lot of the follow on capital for journey, 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, like slightly later stage?
12:08 Speaker 01 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, you know, 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? Like, is there still something weird about it? Or do we have some unique perspective or angle on like, why, like, why are we the ones who are doubling down and where other
12:51 Speaker 01 people might see the company differently? Like, what information do we have that others don't?
12:55 Molly O'Shea? Are there any specific metrics that are associated with that? I know you said like 100x.
13:00 Speaker 01 That one, the proprietary, like 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, that's what I mean by like, how proprietary is this? Then how de-risked is it? Like, how, basically, how much progress has the company made? And in what areas have been de-risked, especially since our round of our previous round?
13:34 Speaker 01 Is this a public company founder? Like, can we see this founder be, you know, ringing the bell?
13:42 Speaker 01 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, you know, 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?
14:09 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?
14:18 Speaker 01 Yeah, so our goal, and this is, kind of goes back to the five to 10 years. Where do you see long journey? Our stated goal for this fund is that we are, we don't want to be afraid to put up to $25 million into our best companies. And that's over time. So, you know, our initial check, we're leading pre-seed and seed rounds. Let's call it with like, a one to two and a half million dollar check. So that kind of gives you an idea of, you know, how much capital we want to deploy into our top, top companies over time.
14:50 Molly O'Shea? How do you think about pricing between those rounds? Like, are you super price sensitive? Does, is that a factor that comes into follow-on?
14:58 Speaker 01 Yeah, we are super price sensitive, I would say. And our average entry valuation on the pre-seed and seed side is about 15, which I think is, is quite a bit lower than, 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. I, you know, that wasn't a big focus area of mine at COTU 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.
15:42 Speaker 01 And I learned this pretty early on, like, you know, basically week one at Long Journey. He showed me, like, entering at 25 million versus 15 million, the exit value of the company and how that impacts the fund model is, is very significant. So this is, it's, it's something that we are always keeping in mind.
16:03 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?
16:26 Speaker 01 Yeah, we try to explain this to, to founders when we're kind of like negotiating terms. But yeah, definitely wasn't as much of a concern at COTU. For example, entry valuation, it, it didn't, we kind of thought about the model differently at COTU and that just wasn't kind of the lever that we were focused on.
16:48 Molly O'Shea? Yeah, well, we're seeing those 2021 pricings kind of come cir- full circle.
16:57 Molly O'Shea? It seems like we might not learn from the past as much as we want to say we are. But these like rapid AI, super high growth companies are, are starting to hit that again. I don't know if you saw, but someone just leaked that cursor who's, you know, almost at like 100 million ARR in what, like 24 months, something crazy like that. They're, they're like pricing their next round around like $10 billion. 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?
17:35 Molly O'Shea? How do you feel about that kind of narrative coming back into the market?
17:39 Speaker 01 Well, what I'm seeing is it's made it very difficult for non-AI companies to get funding, I think. Like, a lot of folks are kind of expecting, like, when there are companies out there going from zero to 100 in 24 months, it kind of like 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.
18:19 Speaker 01 But, um, yeah, I think it's made it really difficult for companies who aren't growing in that way to get the attention that they deserve.
18:28 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?
18:48 Speaker 01 I am definitely not expecting every company to follow this trajectory. I think, and I do question, like, 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 think 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.
19:29 Speaker 01 And I think, you know, maybe they'll end up with a couple of tools, maybe they won't. But I think everything's trying everything right now. Uh, so I think we're probably going to see a big drop off.
19:40 Molly O'Shea? Yeah, I, I feel like with, with all of 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. Um, 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 like, you know, put their stake in the ground as like the brand. Um, I, 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.
20:20 Speaker 01 I mean, yeah, it's possible. I actually, I saw an Instagram reel the other day, um, where it was kind of like the millennial and the Gen Z year talking about what tools they use. And the millennial was like, Google. And the Gen Z year was like, ChatGPT. And then it was like this perplexity, this Pika. It was like talking about, um, these AI tools being like the new version of like the SaaS companies of yesteryear. Um, so maybe like they will just, these newer tools will take over. I think the narrative previously was like, oh, like the incumbents have all the customers already. They'll just like add AI into their own tools. But yeah, I think what we could be getting wrong is like,
21:06 Speaker 01 maybe you kind of have to rethink the entire tool from the ground up, uh, to be AI native. And maybe that matters versus like layering it into your existing product.
21:16 Molly O'Shea? Do you expect most of new companies that are coming out to be AI native? Like I, I'm just, I'm thinking, how much of what you're seeing in your deal flow is AI native? And do you want it to be?
21:32 Speaker 01 Yeah, we are seeing quite a few AI native. I would say like, you know, the, the word that people are using is like agentic, which
21:40 Molly O'Shea? I know.
21:41 Speaker 01 For some reason.
21:42 Molly O'Shea? I don't like it either.
21:46 Speaker 01 But uh, yeah, I think so. We've invested in a couple like vertical software plays that are AI native. Um, and uh, but I think it's like mostly about when we made those investments, it's mostly because like the founder has like differentiated insight into like go to market. So it's not a really, it's the AI is like the cherry on top. Um, but I do think, look, like the chat interface, you know, I think back in like 2017, when this was for like chatbots were first becoming a thing, um, just the experience wasn't that good. But now I think
22:28 Speaker 01 people, it's, I mean, it's just blown up. And I think you can do so much with like the chat interface. Uh, so that's like one way, um, that we're seeing these like AI native apps, like getting tasks done through chat interface.
22:44 Molly O'Shea? I want to break down a couple of companies within the portfolio. What are some of your most exciting or companies that we should be looking out for right now?
22:52 Speaker 01 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. Uh, and they are doing, uh, case picking for distribution centers and they're using swarm robotics. So instead of like one or two, three million dollar robots, uh, they are using kind of like a fleet of, or swarm rather, of smaller, cheaper robots that, you know, are networked together through software. Another one, uh, that has been a high flyer in our portfolio is Superpower, which is like a concierge longevity platform.
23:33 Molly O'Shea? Amazing sweatshirts. I got a sweatshirt. Incredible. Oh, my gosh.
23:37 Speaker 01 It's all about the merch.
23:38 Molly O'Shea? The merch is so important.
23:40 Speaker 01 It's key. It's key. It really is. Um, but I learned so much from Superpower. Um, I actually learned that one of my biomarkers, lipoprotein A, um, 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, um, like really look into that and work on that. So I am a huge fan of Superpower. Um, I really love, in our portfolio, we have a company called Bedrock, uh, which is geothermal for commercial real estate. Um, and I am obsessed with the founder and I, I, I love it.
24:20 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?
24:35 Speaker 01 Okay. I think one of the wildest adventures I went on in my, you know, investing journey is I operated an excavator.
24:45 Molly O'Shea? Oh my God.
24:46 Speaker 01 It was freaking awesome. I like, it was one of the most fun.
24:51 Molly O'Shea? This is diligence?
24:53 Speaker 01 Yes, for diligence.
24:56 Molly O'Shea? Was it like a marketplace for construction vehicles?
25:04 Speaker 01 It was software for allowing people to remotely operate construction equipment. And the company, 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, actual excavator. And I had the fricking time of my life.
25:32 Speaker 01 It's like, this is awesome.
25:34 Molly O'Shea? So I think Cyan mentioned that you guys have a house, like the house is your office.
25:39 Speaker 01 Yes.
25:40 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.
25:50 Speaker 01 Yeah, we wanted to feel like a home, like the home for the magically weird. That's like, kind of what we're, what we're trying to build. It's more than a VC fund. And it, you know, it's more than a community. It's like when, when you walk into our space, we really wanted to feel like you're coming into our home and we want you to feel comfortable.
26:08 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 answer it.
26:23 Speaker 01 What's your opinion on this?
26:24 Molly O'Shea? Yeah, what's your opinion? It's like, I don't know. It's so stale. So, yeah. But do you, do you really, I mean, you, you've come from traditional VC. Do you think it matters? Like, how much of it is nice to have versus like? An actual draw.
26:40 Speaker 01 I mean, it has to be true to yourself, right? Like, I think, you know, Kotu 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 like, this is who we are, a long journey. So that, you know, it, it has to be what's like right for you. I think if you, you know, are trying to
27:06 Speaker 01 kind of convey, yeah, depends on what you're trying to convey and like what your values are. You know, our number one values, chase the magically weird. I mean, not everyone is trying to chase the magically weird. So, you know, they're not gonna have like seashells that you've collected on the beach in their office. But, um,
27:24 Speaker 01 but I think some people, even if it's not, doesn't feel weird or out there, are still like doing it really well. And like, I have great brands,
27:36 Speaker 01 even if that brand is like more buttoned up.
27:39 Molly O'Shea? That makes, yeah, that makes perfect sense.
27:41 Speaker 01 I just think it has to be, it has to be authentic, like you said.
27:47 Speaker 01 It, and it has to be like aligned. And I think it really stems from who the like leadership at the firm is. It's like really a reflection of us as people. So I think, well, like, 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, you know, what everyone is standing for.
28:12 Molly O'Shea? Yeah, it becomes more institutionalized and you, you start to miss the actual like early hustle, lean team dynamics.
28:20 Speaker 01 Yeah, you lose your soul a little, little bit, for the sake of growth.
28:25 Molly O'Shea? It, it becomes a soulless place. How do you think the ingredients for what a successful VC is have changed?
28:33 Speaker 01 Yeah, I mean, this is, like I said earlier, you know, the Chinese Zodiac, this is the year of the deal flow. So we've been obsessed with, like, who has interesting proprietary deal flow? And I think if you are able to build a unique network of builders, and Be like an authentic, create an authentic gathering place for those builders. I think that's like one of the most important things. And that's what we are super focused on. Uh, so I think that along with, you know, having your own point of view, like being an individual and not just kind of following what everyone else is doing.
29:18 Speaker 01 And actually like the ability and desire to stick your neck out there and do something different. And having that unique different deal flow, I think are like 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, um, get in early and get in different.
29:43 Molly O'Shea? Do you think skills have changed? Like, what do you think, like, skill wise, VCs should be focused on? Or what you would want to hire for in like different associates?
29:53 Speaker 01 Yeah, so I think like having that unique different deal flows sort of table stakes. Um, and then it's either, and it, it doesn't have to be both, but I think probably both is even better. It's like, you either have to start out with amazing judgment or just like a willingness to learn and ability to, um, just like be really open to feedback and coachable and being able to shift your judgment, which is not an easy thing to do. But, um, I think that is kind of like the key for an associate.
30:27 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. Like, so do you think that's still important?
30:41 Speaker 01 I think it's super helpful and valuable. I mean, it's definitely, I, and I think it's what attracts great associates also. Like they want to learn from amazing partners. And yeah, I think it's like a win-win for both. Uh, the partners want access to younger founders and builders and operators. Um, and like youthful energy, frankly, you know, someone who's gonna like, I mean, when I was at Kleiner, I was going to like, Seven events a week or something and you know flying all over the place to random conferences. And I mean, John Doerr had like an insane amount of energy, but he, you know, he wasn't.
31:23 Speaker 01 I mean, he actually, he was flying a lot of places, but, but not everyone is. So, uh, yeah, I think it's advantageous to both the partners and the associates.
31:35 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.
31:46 Speaker 01 Yeah.
31:46 Molly O'Shea? He doesn't need to do that at all.
31:49 Speaker 01 He's a maniac in the best way.
31:52 Molly O'Shea? Yeah, I think the same with Howard Morgan, like I see him out all the time. They, they love it. It's their life, you know?
32:01 Speaker 01 I also worked closely with Eric Fang, who's now an entrepreneur when I was at Kleiner. And he also, he was incredible and had a ton, a ton of energy.
32:10 Molly O'Shea? Yeah, it's, it's like a funny balance of going to lots of events, networking, but then also like staying put and being focused and grinding. It's just always going to be a balance.
32:23 Speaker 01 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. He, it's awesome.
32:39 Molly O'Shea? One thing that Lee mentioned about you is that you're building essentially an adult frat and sorority. So is this like how you're cultivating community? Like what does this mean?
32:53 Speaker 01 That I'm building an adult frat?
32:56 Speaker 01 That's a hilarious way to put it. Um, how do I put this? So I'm the youngest of four. I'm, I have three older siblings, so I was always like used to a lot of people being around. And as an adult, I don't know, I, and I'm an extreme extrovert, so I love being around people. I actually like, don't like not being around people, like being alone is like, ugh, you know? I'm like, when can I call my next friend to hang out?
33:23 Speaker 01 So I think I, you know, always kind of had a roommate when, you know, I graduated college, I've had roommates and then I kind of just never stopped. So even like 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 another family to live with us. So we just always enjoyed having a lot of energy, a lot of different personalities and like 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,
34:05 Speaker 01 leaning so much on their partners for literally everything where if you live in community, you don't have to do that.
34:11 Molly O'Shea? What do you think the biggest challenge of that is? Like, I can't imagine. It's always happy-go-lucky.
34:19 Speaker 01 No, it's not always happy-go-lucky. You definitely sacrifice, you make sacrifices, but you do it knowing, knowing like why you're doing it. And, you know, when you choose to live in community, sometimes, you know, there's like 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, it's, you know, 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 knowing, having, you know, the correct expectations and knowing what the trade-offs are
35:03 Speaker 01 going into it. And we've just chosen that we want to make those trade-offs.
35:08 Molly O'Shea? Since the office is a house, would you put founders in there and like open the doors for building a community within the long journey office? Like, I'm just wondering, like...
35:24 Speaker 01 So we have a guest room and we let visiting founders stay in the guest room. But yeah, we're like starting to host events there. We're starting to view it as a place to gather our community. I mean, as you know, I love music. I think, you know, 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.
35:51 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, what are the components that make it like really vibrant?
36:06 Speaker 01 I think like being the place where people can talk about their boldest ideas and not be afraid of, you know, what people think about it is how you build an amazing community for builders where they can like 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 fricking wizard at this.
36:47 Speaker 01 But like, 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 like a piece of stationery and write to someone who played a huge role in a core memory and then like had them write down the address and then we sent those off. And we think things like that help you reconnect and like, just really like tie into your purpose. And that's what we're trying to create.
37:21 Molly O'Shea? Purpose is one thing that Cyan and Lee had mentioned multiple times when we were talking a couple of months ago. Why do you think that purpose has kind of like dimmed a little bit in society? And why do you think we really need to hone in on it?
37:41 Speaker 01 That's a great question.
37:44 Speaker 01 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?
37:59 Speaker 01 So I think maybe that instinct or insecurity has held people back from talking about it.
38:06 Speaker 01 Whereas it's really fricking important and people need to embrace it. And I think, I actually think like Gen Z does a really good job of leaning into this. And, um, and yeah, I, I'm really glad that Cyan has been pounding the pavement, talking about this and not being afraid to talk about it, uh, cause it's fucking important.
38:27 Molly O'Shea? Yeah, yeah, it's super, it, it really is because we've slowly created a very atheist culture of people chronically online that don't connect with individuals in the real world anymore.
38:41 Molly O'Shea? And if you're living in that monotonous or like monotonous cycle, you do lose a grasp of like, oh, if I have like access to everything in the world, what's the point? And like, what is my true meaning or like, what should I believe in? And so it's, it's really awesome that you guys are cultivating such a strong community and brand around you to fuel the next, you know, generation of founders to, to lead with purpose and to have such a passion behind them and pursue these wacky, crazy ideas, or sorry, wild, weird ideas with a resonatise.
39:20 Speaker 01 One thing I'll add is like, there's kind of been this like Wall Street-ification of, of VC. And if I were to think about, you know, people on Wall Street talking about purpose, like, they're probably rolling their eyes, right? Like, this is not something that a lot of investment bankers talk about or, or, or think about, at least I assume.
39:44 Speaker 01 Maybe, maybe I'm wrong. Maybe there are like really, you know, people have done their eat, pray, love thing and have then gone back to investment banking. I don't know. But, um, but yeah, we're, we're trying to kind of be the opposite of that.
39:56 Molly O'Shea? I think, I think we feel it more because we're closer to culture. Like tech is like very connected to culture and making culture. Someone said like, I think the hot take, their hot take was like Silicon Valley is actually like the epicenter of culture because so much innovation comes out of it. And that like, that shouldn't be overlooked. But if, if like, we have the opportunity to continue to like, 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?
40:34 Speaker 01 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 like unhinged, best, hottest takes and interesting info is all on group chats. That's kind of my hot take. And so I think like, I am not as, you know, I'm not like doom scrolling on Twitter as much. I am just, but I am a part of a lot of like really interesting group chats. And that is where I think the most vibrant conversations are happening. I think most value add is dumb.
41:19 Speaker 01 Unless it's something we think about is documentary level value add. If you're not gonna provide documentary level value add, then it like, it doesn't matter. And it's all super marginal.
41:32 Molly O'Shea? I also believe that value add is, is something that like, VCs should stop marketing. Like just don't market it. The most like value add VCs can give is like, commercial value add and like opening doors for contracts and like customers, honestly.
41:52 Speaker 01 Yeah.
41:53 Molly O'Shea? It's, it's such a, value add is such a weird marketing angle. Um, I don't know. I think that's a really good one, honestly. You got me fired up.
42:04 Speaker 01 Yeah, we we also talk about like not being value detracting, which like some VCs actually are like some VCs give like bad advice and are really proactive in a bad way. And we're just we're trying to not like, 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. Because you're building a company. We're not building the company. You are.
42:31 Molly O'Shea? Yeah, I think the note says like 80 to 90% of investors actually provide negative value.
42:39 Speaker 01 Yeah, I've heard that also. Yeah, so we're just trying to be in that, you know, 10 to 20% who aren't.
42:45 Molly O'Shea? Alongside Purpose at 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?
42:59 Speaker 01 Are we talking about being a bubby?
43:01 Molly O'Shea? Yes, we're talking about being a bubby.
43:03 Speaker 01 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. And a bubby is, bubby is a Yiddish word for grandma. So think of like, you know, your your grandma and what it represents is like, your grandma's probably seen some shit. So she's been through a lot. So the, you know, roller coaster and ups and downs of the startup journey are not going to faze her because she's, you know, she's probably been through a war, maybe two. So that it's like even keeled, like unfazed by by the ups and downs of the startup journey. And then also unconditional love, but
43:47 Speaker 01 tough love. So grandma is going to be direct and tell you how it is. But also, you know, she's going to make you a cup of soup when you're sick and and she's going to give you all the hugs and kisses. So that's kind of what that represent. It's like the directness, tough love, but unconditional love. And, you know, being unfazed by the ups and downs of the startup journey. Some investors, you know, if something horrible is happening at the company, they're going to be like, oh, no, woe is me. But, you know, Bubby knows that everything's going to be okay and has that perspective from experience.
44:24 Molly O'Shea? We need the wisdom.
44:25 Speaker 01 Mm hmm. Bubby wisdom. And, you know, there're going to be like cookies around and shit.
44:31 Molly O'Shea? We need cookies. We need wisdom.
44:34 Speaker 01 Yeah.
44:34 Molly O'Shea? It's important.
44:35 Speaker 01 Yeah. It's like, so we kind of, um, the Long Journey Office, we also like, kind of wanted to feel like grandma's house in a good way, not like the smell, but you know, like a cool grandma.
44:50 Molly O'Shea? Maybe not the smell.
44:53 Molly O'Shea? So to close out, I just want to end on a good, positive note. What are you most looking forward to this year?
45:00 Speaker 01 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. It's my first kid.
45:15 Molly O'Shea? Congratulations.
45:16 Speaker 01 Thank you. Uh, 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, um, I think just like continue to make awesome, weird investments, uh, in founders that are kind of pulling the future forward. Uh, and you know, hopefully seeing like downstream investors agree, agree with our weird taste.
45:46 Molly O'Shea? If it's any indication, I've definitely seen that your portfolio is fantastic and I have no doubt about that.
45:55 Speaker 01 Thank you.
45:56 Molly O'Shea? Well, thank you so much, Ariel. It was a pleasure and I hope you have a wonderful time skiing in Montana. I'm very jealous.
46:03 Speaker 01 Thank you. Are you a skier?
46:05 Molly O'Shea? I snowboard.
46:06 Speaker 01 Awesome.
46:07 Molly O'Shea? Yeah. I hope that's okay. I know there's a rivalry there.
46:10 Speaker 01 Oh, no, I, I actually snowboard. I had an interlude of snowboarding when I was about 10.
46:15 Molly O'Shea? Love that.
46:18 Molly O'Shea? All right. Well, go enjoy the slopes. Thank you so much.
46:21 Speaker 01 Thank you.
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