Rex Woodbury - Daybreak

Rex Woodbury - Daybreak



Rex Woodbury is the founder and Managing Partner of Daybreak, an early-stage venture capital firm based in New York City.

Before founding Daybreak, Rex was a Partner at Index Ventures the premier venture capital firm that invested in Adyen, Revolut, Roblox, Discord, and Figma among others.

Rex focuses on the application layer of technology, often investing in internet, software, and marketplace businesses with the potential for viral adoption.

He also writes Digital Native, a publication about people and technology that reaches 50,000 weekly readers which i highly recommend.

During this episode we discuss about the art of early stage investing (pre-seed and seed), the pros and cons of social media and the power of technology to bring people together.


Writing digital native newsletter

[00:02:07] Calin: I'm a big fan of your newsletter. I've been reading most of your social media posts, and I also read your latest one about the art of early-stage investments. I'm very much looking forward to having this chat with you.

[00:02:19] Rex: I appreciate it. Yeah, I've been writing Digital Native for a few years now and working as a venture investor the entire time. However, I realized I hadn't really written about the art of investing itself, specifically how I think through founders, markets, and products. Most of my writing in Digital Native focuses more on large macro trends and what startups are building along those trends, hastening them along. So this one was a bit of a departure, but mixing it up once in a while is good. I appreciate you reading along and am excited to have a conversation today.

[00:02:50] Calin: You talk a little bit about market sizing. You say you don't really look that much at the market size, but the team is very important, and you want to see that the founder has the X factor. Can you tell us how you assess a team and an investment opportunity?

Early-stage investing and Daybreak

[00:03:09] Rex: Yeah, Daybreak is pre-seed and seed focused, and I always like to use the word 'artisanal.' In venture, over the past few years, we've seen a kind of financialization of the asset class, almost an industrialization of venture. However, I think at its core, venture is structurally built to be a cottage industry. There are only a handful of companies each year that become the breakout, power law companies that the venture model is predicated on. That's why it's important to be in early, to have good ownership, and to be more of an artisanal, craftsman-like venture player, as opposed to the 'spray and pray' strategy at the early stage that some more asset management-like firms have adopted in recent years. Daybreak is very much built on the vision that there's a gap for the next generation of firms that need to be craftsmen-like and hands-on at pre-seed and seed.

And at that stage, it really is about the founder. My view is, of course, the market matters. Of course, the product matters. There are only so many business models that can underpin those $5 billion, $10 billion companies that we need to rely on in venture. So, yes, as an investor, you need to be able to assess what are the right business models, whether this is an attractive market with the right dynamics around capital intensity, potential dilution to my capital, whether it's a winner-take-most market, or whether there is built-in defensibility. Of course, those things are important, but at the end of the day, I really think early-stage investing is all about a person, and having conviction in one person or in a team. And that's why intuition is also important: can you understand what drives people and what that X factor is?

The x-factor in founders and Market Dynamics

[00:04:49] Calin: It's quite a difficult task where, on one hand, it's just super early. So you need to believe in the founder, but at the same time, you need to assess the market and understand, perhaps, the market structure, like the framework in which that market operates. How do you balance that? How do you balance the assessment of a market? Do you look, let's say, at profit margins at existing companies? How do you strike that balance?

[00:05:15] Rex: Definitely understanding the key question for investing, which I think has gotten lost these past few years, is eventually: can this business generate cash flow? That is what matters. And we forget that because the time horizons are so long in tech, and there's become this dynamic of hot potato where, as an early investor, you say, who cares if it generates cash flows in 10 years? Because I'm just going to pass the hot potato to the series A, B, C, and D investors and maybe exit in one of those private rounds. But at the end of the day, the question is: is this a fundamentally sound business that will generate cash flow, that is sustainable and is going to be profitable one day? So, margin structure matters a lot. That's why SaaS is a really elegant model with such wonderful high gross margins. And, to your question about other dynamics in the market, I always like to look for a viral adoption pattern or some kind of network effect. I think that is essential for early businesses to actually hit escape velocity. All startups are new businesses, but not all are a fit for venture or true technology startups. Venture-backable ones should have that potential for virality, for hitting escape velocity, and for growing very quickly. And regarding market sizing, I mentioned in that piece the classic example of underestimating market size could be something like Uber. In the early days, if you did a market sizing analysis for Uber, you might say the yellow taxi cab market is only so big. What you would've missed is that great products like Uber can expand the market because geolocation made it easier to call a car to anywhere, and the ratings system made it safer and more trustworthy. But Uber is also a classic marketplace where it has a tipping effect. Once you get liquidity in the market and you've got the supply and demand side building, you can build in great things like referral loops and there was great word of mouth. It's a business that we saw able to grow very quickly through venture funding.


[00:07:31] Calin: And how do you check virality, or the potential for virality in a product at such an early stage, like pre-seed and seed? And maybe as a follow-up, what do you see in the market right now? What are the terms for pre-seed and seed? I would assume that entrepreneurs have to become a little more disciplined in building something at pre-seed, even generating revenue at seed. What do you see in the market?

[00:07:55] Rex: To answer your first question, I think that goes back to why it's all about the entrepreneur. Often at pre-seed and seed, there aren't products in the market, nor early proof points of traction or engagement or retention. Ideally, maybe by seed, you're able to see a strong K factor of referral motions happening and really early signs that there's actual viral growth. Usually at pre-seed you wouldn't see that, and often at seed, you're also not seeing that, even with the best founders. It's just too early.

The question becomes, is this entrepreneur someone who understands the levers to pull in his or her business? Does this person have a strong clarity of thought on the product side and what are the different hypotheses on how virality will be built into the product? And then also, how will the go-to-market motions work? So it's about assessing whether the market and business model support that kind of virality, but mostly it's about whether the entrepreneur understands how to create that virality. Regarding pre-seed and seed, I mean, pre-seed and seed haven't come down in the same way that late-stage rounds have. They're still at kind of frothy-ish prices. I think the average pre-seed this year was in the seven to ten range, seed was up from 12 to 13 post or so, and the average seed round was around 3 million. There hasn't been a huge correction. I'm still seeing a lot of top seed rounds done in the 15 to 20 range. Pre-seed, maybe more of a two on 10. But I think we are seeing more entrepreneurs be open to a true pre-seed. In the past few years, we saw a lot of founders kind of skip pre-seed and raise a frothy seed. But now, more are realizing it might be more intelligent and savvy to raise a smaller amount of capital, maybe a million, a million and a half, find product-market fit and then raise a more substantial seed round. That can sometimes be a safer path versus setting yourself up pre-product really early on for a frothy seed round, and then realizing the hurdle for series A is quite high.

Daybreak Fund and Fundraising

[00:10:29] Calin: Tell us a little bit more about Daybreak. How big is the fund? How many deals do you want to do per year? Have you already deployed some capital? I think I read something about that.

[00:10:38] Rex: Yeah. So, I registered this fund as something called 5 0 6 C, which is unique. When you register a fund in the US, you can be 5 0 6 B or 5 0 6 C. Most people do 5 0 6 B, which basically means there's a non-solicit; you can't really talk about the fundraise until it's done. For me, it just felt more authentic to do 5 0 6 C, which allows you to talk publicly alongside raising the fund. There are some hurdles to that, like showing everyone is an accredited investor and doing more paperwork. But it felt more authentic to me, aligning with Daybreak's vision of modernizing venture. Part of that meant more transparency and openness with investors and founders about the mechanics of building a fund. The high level is, it will be around a 30 million fund or so, focused on pre-seed and seed. We write 500K to million-dollar checks, which means we sometimes lead at pre-seed or co-lead at seed. Sometimes we can co-lead at seed or invest alongside a great lead that we like. It's early-stage focused, and we really focus on that zero to one with entrepreneurs.

[00:12:09] Calin: Is it hard to raise a fund? I would assume that the markets were much more difficult than in 2020 or 2021.

[00:12:17] Rex: I mean, it's so funny. People, people ask, yeah, oh, it's difficult market, is it? And I say, well, you know, I've never raised a fund before. But yeah, I think it does give a lot of empathy for founders where, you know, I can now say to my entrepreneurs, you know, a lot of the, the GPS at, at bigger firms, you know, haven't really raised capital ever.

And, you know, I've been on the road having a dozen, dozens of conversations and, you know, just like my, my founders who understand, they say I've said the same kind of talking points to, you know, a million different people. You know, I'm like, I've been there. I get it. And by the way, I know how to raise capital and, and I think that will come into play in helping you hopefully in your future rounds.

so that was another reason I think building in public was helpful for me in that, you know, it's just been very freeing to be able to talk about daybreak as I build it. As I raise it, I'm able to make early investments as we close some capital. But then also I think it gives me an edge in working with entrepreneurs. 'cause I'm able to say, you know, I understand the minutiae that you're going

through, where you know, I've been dealing with trademarking the name and fund formation docs and setting up bank accounts. And, I do believe that starting a company is much more difficult than starting a fund because you have to really build a differentiated product.

And in many ways, in venture, the product is sort of, you know, built in decision making and, and sort of, you know, less tangible. it does give a little bit of empathy and I think, know, entrepreneurs respect that kind of entrepreneurial journey.

Clarity of thought and product differentiation

[00:13:40] Calin: Absolutely. And just touching maybe a little bit on product differentiation, like how do you think founders should think about product differentiation at pre-seed or seed? Like do you think it's something that you need to be, focused on or you just have to iterate on the product and see what works? and that will kind of, guide you in the product differentiation journey.

[00:14:01] Rex: I think it's a little bit of both. I think, you know, often at pre-seed it is very early and so I think the best founders have clarity of thought and a hypothesis and a lot of conviction and what they think is going to be the right approach, but also a lot of open-mindedness to understand what might not work, what might be, something that could be tried if this doesn't work.

So it's kind of a balance of. Clarity of thought, conviction and not being so, so wishy washy or not having a point of view. I think, you know, usually you want an idea that has merit. It's rooted in your own lived experience or work experience. You've done a lot of work in the market talking to customers, you know where to start. But the best founders also are pretty open about what they don't know and that always gives me a lot of, you know, kind of solace in the fact that they probably know what they know if they also know what they don't know. And it's a little bit of self-awareness. And so I think it's very fine as a founder to say, this is our view, this is what we think is sort of the differentiated insight that's missing in this market.

And this is why, you know, there's a compelling why now that's, this is why this approach and this product and this go-to market

is gonna work. That said, you know, there are all of these variables, these A, B, C variables that we don't know, and we're gonna learn in the next six months from the market's feedback, and we're gonna iterate quickly based on that feedback.

Social netoworks and consumerish B2B

[00:15:18] Calin: you have I think like what, 54,000 subscribers. some of the. Post that grabbed my attention was on social media and online communities. a lot of people try to find belonging, internet communities. what are your learnings after doing so much research on. On the topic. So I know that you wrote about Billy. Billy, you wrote about Instagram, you wrote about Snapchat. Where is social media heading?

[00:15:44] Rex: Yeah, it's a good question. I mean, I do think social is a very tough category for venture and you know, I do a lot of consumerish investing, but I always say consumerish because a lot of the investments I do are B2B, they also build along these kind of big shifts and, and consumer behavior. and I think consumer is a tough word because, a lot of the best, you know, consumer quote unquote companies of the last decade are, kind of picks and shovels.

You know what I mean by that is, my partner works at Fair, it's a B2B marketplace. It doesn't touch necessarily the consumer. These people out here on 15th Street right in front of me, probably don't know fair, but they've probably shopped at a store that sources products through it. Similar with Shopify or you know, some of the great kind of Prosumer like companies of the last, notion slack figma, they're very consumer-like in their adoption pattern, but they are enterprise software businesses.

Social I think is a tough category. I mean, it is true consumer. I think it is a tough one now where in a portfolio of, you know, consumer investments, you probably do want some exposure.

Maybe it's a one, two social companies, but. It's so binary. You have to have such product velocity and evolution and really a product of visionary is the founder. you know, we've seen so many kind of hot buzzy photo sharing apps over the past few years, whether it was Paparazzi or BeReal or Dispo or, now Lapse and Locke.

I think what is challenging is the rise of them to number one on the app store shows that there is consumer demand for something different. But there is such kind of velocity and product execution that is required to maintain that. Right? We saw this most prominently probably with BeReal where, you know, it was a compelling enough kind of, it was more of a feature. And it was structurally difficult to monetize. 'cause time spent on the app was, you know, by definition, quite low. but there was no second act that came from the company. I mean, they had all of these users, they had the downloads, but there was nothing really that they moved quickly enough to capture that attention in, in zeitgeist.

And so it's just a really difficult category. I always say the next consumer social company probably looks a lot more like a Roblox than an Instagram. What I mean by that is all these photo sharing companies, I mean, they're sort of Instagram 2.0, but they really are just kind of, similar to Instagram in a lot of ways with slight twists on authenticity or things like that. I think the next kind of social company is something that's probably 3D more immersive, more game-like, and we'll see what comes, I mean. You know, there are a lot of kind of roadblocks for Gen Z Roblox for Gen Alpha companies coming out, a lot of kind of generative AI plus ROBLOX companies. but to answer your question on, on community, I mean, one of the key theses behind Daybreak and one of the areas I like to invest is this idea that. You know, so many of us are lonely. There's this mental health crisis, this loneliness epidemic, and part of it is ironically due to social media and due to technology. But at the same time, technology is also a potential solution. And the right companies and the great, the right founders can find ways to combat that isolation and loneliness. And, you know, I, I could talk all day about what that actually means in practice on the startup front, but it is a core theme of ours.

Disrupting LinkedIn

[00:18:46] Calin: if you would have to build a new LinkedIn tomorrow, how would you go about it? How would you get, let's say your first 1000 users.

[00:18:54] Rex: Well, I think that's a funny question because I really do actually think one of my hot takes is that LinkedIn is probably the hardest to disrupt of any of the, the social networks. Probably every year in venture there is a hot new company that aims to be kind of LinkedIn 2.0 or LinkedIn for the next generation.

And the reality is the network effects are incredibly strong on LinkedIn. I mean, you've got, certainly, we all, all have our whole work histories there and the vanity of checking our profiles. you know, one of my favorite things about LinkedIn is back in the early days, how The founder has mentioned that they were shocked to find out that the profile people viewed the most was their own profile. which I think plays into, you know, kind of the concept of the seven deadly sins in consumer technology of, of vanity. but I mean, there's such a, a strong base of recruiters there too, and it has a really kind of unique business model, is much more multi-pronged and multifaceted than Most of the social companies.

So, you know, long story short, I think LinkedIn is hard to disrupt. that said, I mean, work is changing very dramatically in that the younger generation wants much more kind of autonomous self-directed flexible work. And so if anyone is to disrupt LinkedIn, I think it is one of two approaches. One is being a more blue collar, given that LinkedIn targets white collar work. and so that's a potential wedge. And the other is targeting more kind of freelance and project based work. And so is there a better way to showyou know, I worked on this freelance design project and you know, this company can verify that I did a great job and oh, by the way, I worked with these people.

I add this collaborators and that's kind of a viral, viral network effect there. A lot of companies have gone after this. Contra does something like this? Poly work started with a thesis, similar read. CV has done some interesting things. I think the challenge is that it is very difficult to disrupt LinkedIn. it's not to say you can't build a, a good business as sort of a, you know, a freelancer marketplace or freelancer kind of job sites. but actually displacing LinkedIn is a formidable challenge.

Coming out and being true to oneself

[00:20:55] Calin: In closing, let's, get personal a bit. from the outside. You know, it looks like you had like this perfect career and perfect life. You went to Goldman Sachs, TPG, Index. Now you have your own fund. Maybe you can tell me about a moment that you struggled in your life and what, what were the learnings that came from it?

[00:21:13] Rex: Yeah, I mean, I think I I think, you know, this is such a, a social media concept we were just talking about as well, sort of like the highlight reel and us always kind of overestimating, other people's lives and, and the shininess of it. I mean, I, I am very fortunate in that I come from a very loving family and, You know, feel, feel grateful that we're talking just after Thanksgiving. And so I feel like, you know, especially kind of grateful and thankful for that. that said, I mean, I think, you know, I had a lot of kind of formative experiences growing up with a lot of kind of internalized shame. And so I, I had a very long closeted period. I came out when I was sort of, I think the last week of sophomore year in college around my 20th birthday, but. I probably knew I was gay when I was like 8, 9, 10, very early. And so I kind of had that, like decade of putting on a facade. And, there's a lot of great literature out there.

Well, there's one book called The Velvet Rage. There's one book called The Best Little Boy in the World. But it kind of, they all build on this concept of, you know, I, I think a lot of gay men in America at a young age. Internalized a lot of the shame for being different or not kind of adhering to stereotypes around masculinity or, or what they should be.

And so, they instead seek a lot of external validation to sort of compensate for that and try to be really perfectionists and learn to constantly kind of iterate and refine themselves to seek approval from others. And I think, you know, I'm, I'm a classic people pleaser and it has been a long journey to get away from that, and actually do, because. you know, the, the beautiful side of that is I think, you know, the flip side of, of, pleasing is a little bit of compassion and empathy. But at the same time, it also, in order to really challenge yourself in order to really be happy, you really kind of do have to march to the beat of your own drum.

And so a lot of my friends have helped me shift that worldview a bit. And I don't know, I mean, I, I think the, someone was asking me this weekend, we were kind of talking about, Seeing our friends for Thanksgiving back home and our siblings and then coming back and I was at this kind of big gay party on Saturday night and we were kind of like, wow, we feel so fortunate to be gay because, you know, right when I came out, probably like a year or so after I.

Someone asked like, oh, if you could take a pill and be straight, like, would you? And I was like, of course. You know, I mean, I was probably like 21 at the time. I was like, why would anyone choose a harder life where they're, you know, part of the small minority group and don't you wanna be, you know, the normal, normal sort of person with an easier go at things?

And I mean, that could not have shifted more dramatically over the past. Probably starting around like 23, 24, 25, when I embraced that identity more and kind of was like, actually no. Like not only does this give me insight into a really unique culture and piece of society, but it also gives me this shared kind of through line and connection with people all around the world and a lot of empathy and compassion and, and a community no matter where I go.

And I think it has been the most vibrant part of my life. so, you know, I've really kind of, I think, gone over that arc of A lot of internalized shame and seeking validation and still fighting those things, but come a long way in that.

[00:24:17] Calin: Thank you, thank you very much sharing that. I remember reading one of your posts where you have this picture with the chicks magnet, which I thought that it's very funny because it turned out like to be like the opposite, of what you actually wanted.


[00:24:32] Rex: Oh God.

I think that, I think that was, I forget what, why I put that in one of my pieces. I think it was, well it was definitely a Halloween costume when I was in high school. And I think it was like me trying so hard to fit in by like wearing this funny costume. And of course it was ironic 'cause I was like deeply closeted at the time and no way a chick magnet.

But, very cringey in retrospect. So I don't know why I reintroduced that to the internet archives, but here we are.

Pros and Cons of Social Media

[00:24:55] Calin: talking about social media, how it can push you to wanna fit in and then it will drive what type of posts you post on Instagram. But also on the other hand, you mentioned this Chinese gay person that found a supportive community through the internet.

How do you see like these two trends playing in the future?

[00:25:26] Rex: I mean, I think there's always gonna be a performative aspect to online presence or social media. I mean, you know, humans are often performing for each other in, in some way. I mean, we're just social animals and even sort of quote unquote authenticity of. Photo dumps on Instagram or the spontaneity of Be real.

I mean, there's a lot of performance underlying that, right? Like I think there is a, you know, people are like, I'm gonna post this blurry photo as my third post in my carousel on Instagram. 'cause it shows, I'm like, too busy having fun to like pick, take clear photos, you know? I mean, I think it is, there's always a performance aspect, but what you're saying gets at something that I really love about the internet and one of the reasons that I got obsessed with technology and consumer behavior, which is that. I really do fundamentally believe that. The power of the internet is connecting people in new ways and finding new forms of community. And you know, you see that in Discord has 19 million weekly active servers and they are so niche and I think there are three or 4 million subreddits out there for kind of the most random communities you can imagine. I always think of a quote from Jack Conte at Patreon where he said, you know, you might grow up in a small town where there are a thousand people and you are. The odd man out, the odd woman out. You are really the only person with some really weird interest or you just feel really different in other, but online, you know, one in a thousand, I mean there are four and a half billion people online.

That means there are four and a half million people as weird as you with that interest. And so everyone can kind of find their tribe and community. and the Chinese founder that you mentioned, I mean, he is the founder of a gay dating app called Blued, and I always say, you know, Dating apps are an impactful company, first and foremost, because they can actually introduce you to your life partner, arguably the most important, you know, decision, and connection of your life. And then, you know, he, he really talks about in the, in the gay world, I mean, gay dating is much more prevalent, I think for straight couples. It's like 40 to 50% of people meet online. I think for gay couples it's more like 70 or 80% now. and yeah, I mean, it, it, it is a really powerful tool to be able to connect with people in new ways.

And, you know, this extends way beyond dating. I mean, you know, it's people meeting people in in Roblox and of course on Instagram and, and TikTok with its pair of social content, sort of putting you in front of strangers. but it's a really interesting theme of online belonging. And of course that also plays into a little bit of Loneliness. and we have to regulate that and put in the right guardrails. But I think it's a very compelling argument for why technology and social media even are actually net positive externalities for society.

Shifts in Consumer Behaviour

[00:27:55] Calin: and what are some shifts in consumer behavior that will point, towards a product that will increase belongingness?

[00:28:03] Rex: I mean, I think the destigmatization of mental health is one piece. I think, you know, you see a younger generation, you know, partly because of people being so open online to talk about their struggles and these topics that, you know, younger people are just much more willing to seek therapy orum, seek out, you know, help in other ways and. that's a, a big generational shift in, you know, the first name of Daybreak before it was called daybreak, was actually tectonic, because the things that interest me are these kinds of tectonic shifts in technology, adoption, and human behavior. You know, one of my mentors was like, Rex, that is way too severe a word and austere and like pick something more you and, and Daybreak is a little more hopeful and optimistic. And I think he was right. But you know, tectonic captures, you know, mental health being de-stigmatized as a tectonic shift. And you know, there are many different ways to invest behind that or build companies behind that.

Right. It could be, a B2C marketplace, like a headway. It could be a B2B company, like a modern health. it could be an AI chat bot, like a robot health, you know, I mean, there are a lot of different businesses writing that shift and also. Catalyzing that shift. but that's one example of, you know, one compelling trend to follow.

[00:29:10] Calin: Interesting. I saw that 776 invested in this group therapy. App, which I thought that it's very, very interesting. So you just get together in a group of five to six people and you just talk, through your emotional state. so instead of having a psychologist, is more like a peer- support group.

[00:29:29] Rex: Yeah, I mean, I think that's, that's true. I mean, I, I spend a lot of time talking to kind of therapists and learning about the space, and I think for a lot of young people, group therapy is actually quite beneficial because it just makes you feel that you're not alone in this challenge. And, and that's particularly true for. Things like eating disorders where a lot of the treatment can just be understanding that there are other people going through this problem. And basically it's a challenge that it's, it's not just you. so I think there are lots of interesting business models around that. And, and, you know, the unit economics for group therapy can have to be more compelling than for one-on-one therapy too. it's just a convoluted and crowded space, and so you have to find the right go to market.

Fred Wilson - USV

[00:30:04] Calin: which investor do you admire and why?

[00:30:07] Rex: I mean, I started writing Digital Native largely because I was reading Fred Wilson at USV's writing for many years and sort of admired how prolific he was. And that changed my view that I felt like too many venture investors were doing content but not actually having a point of view or an opinion, which sort of defeated the purpose and. And of course that's because you have sort of a timestamped history of like your thesis and predictions, and often you're wrong. But my view was, you know, it's, it's more interesting to just take a point of view and have a stance. And I've been wrong many times, but I think at least I'm proud that I like put out my thoughts there.

And so I always try to do that with Digital Native, and Fred always did that with his writing. so I'd probably say him. And then I also, you know, a lot of Daybreaks, kind of vision is built around kind of emulating a lot of aspects of USV and that I think they have been very disciplined in their fund sizes.

They've been disciplined and Being more artisanal and early stage and high conviction. And, you know, I don't expect us ever at, at daybreak to be a 50 person team. Certainly not the 500 person kind of asset manager. I think we'll be ideally kind of a lean partnership of, you know, three to five folks in three to five years and, you know, kind of stay kind of nimble and small.

And so I like how USV is is thesis driven. I always say you have to be You can be thesis informed, but founder first in this job. And, and that's kind of the tone I like to strike with Daybreak, where, you know, we have a lot of views of where the world's going and where the compelling opportunities are, but, and it's all about the people and finding the people who are able to build that into reality.

Consumer Behaviour and Technology

[00:31:38] Calin: It's all about the people and what gets you unreasonably excited nowadays?

[00:31:43] Rex: I kind of geek out about all aspects of tech and people in the intersection of the two. I mean, you know, right now, I guess, you know, seeing AI in real time and, you know, just the past year we've had from, I. You know, it's been about one year since chat GPT launched and you know, tools like Mid Journey or like Magic and you know, it just feels like we have so many kind of incredible moments and we're very early in the application layer there.

But you know, the kind of through line I think of my career and interests are, you know, that intersection of people in tech or culture in tech and understanding how people use technology to communicate with each other, to create things, to earn a living, to collaborate. I mean, Is that is interesting to me and it's, it's both B2B to C.

It's B2B, it's B2C, but it's really around these elegant, beautiful products that make life more enjoyable and easier for people.

Tiny Beautiful Things

[00:32:35] Calin: And tell me about a book that had an outsized impact on your life.

[00:32:39] Rex: One book that comes to mind is a more recent read. It's actually called Tiny Beautiful Things by Cheryl Strayed. so she was actually the author of Wild, which was made into a movie with Reed's Witherspoon and, tiny, beautiful things. It's actually this compilation of. When she was, before she was really a prominent author, she took this job writing, column online, anonymously or synonymously, called Dear Sugar, and her name was Sugar. And she would kind of, people would write in and say, you know, I'm struggling with, you know, my, my relationship with my dad is really afraid and I'm not sure whether I should invite him to my wedding or, you know, I had a miscarriage and. You know, my partner's not really understanding of it or all these really kind of thorny emotional issues. And the way she responds isn't like a normal advice columnist. She weaves in her own story and it reads more like a memoir. but it's an incredible book and one that I came out of it being like, yeah, I really, truly think this gave me a better window into humanity and made me a more empathetic person.

And it's a beautiful book. It's very moving. It's a lot of different vignettes that are assembled together into this cohesive hole. But, that is probably the book I recommend most often to people and usually people are, are really big fans and like it so tiny, beautiful things. I recommend that to anyone listening.

Advice to younger self

[00:33:54] Calin: Tiny, beautiful things. and the last question, if Rex from 10 years ago would listen to this episode, what would you tell him?

[00:34:00] Rex: I mean, I think it took me a little bit. In my career to start thinking more first principles about the things that interest me. And it's such cliche advice of, you know, do things that are interesting to you and that's, you know, that's what you should do for work. And of course it's ob it's a quite privileged thing to do and say as well. I don't know. I mean, it took me a little while. I was, I was kind of on a path that I thought I should do and. You know, kind of following more of a ladder and then I stepped back and asked myself the question, which I always tell younger people to, to ask themselves as well of, you know, when you're reading the newspaper or, you know, a more updated version would be like when you're. Like, reading articles online or even when you're watching YouTube videos, like what are the things that actually are interesting to you that you wanna learn about, that you wanna read about? and for me it was always really people and technology. and so that helped me kind of hone in on the things that I really like and spend time on and, and less sort of being reactive and more being proactive about spending time on those things.

So I wish I'd gotten there a little sooner. I think, you know, hindsight's 2020, but, That, that would be my advice. Just to kind of actually be truer to the things that interest you.