Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: How Roam Research Analyse Product Design, Team-Building, The Future of Collaboration Tools & Applying Tesla Go-To-Market To Roam with Conor White-Sullivan, Founder & CEO @ Roam Research About this episode Conor White-Sullivan is the Founder & CEO @ Roam Research, the tool taking over our industry providing a seamless note-taking tool for networked thought. Prior to founding Roam, Conor founded 2 prior businesses and also worked at HuffPost as a Co-Founder of HuffPost Labs where he reported directly to Arianna Huffington and HuffPost CTO. In Today’s Episode You Will Learn: 1.) How Conor's high school wrestling career taught him "how to win"? What was the founding story with Roam? How does Conor think about when to stay true to the vision and persist vs when to give up? 2.) How does Conor think about the product design philosophy they have @ Roam? Conor has said before, "Roam is not about taking better notes", what is Roam about then? How does Conor think about the importance of adding challenge to a product? What does he mean when he discusses the importance of "low floors and high ceilings" with regards to product design? 3.) How would Conor analyse his own hiring and team-building philosophy? Why are the two most important traits, "girt and autodidacts"? How does Conor really stress these two characteristics in an interview process? Why does Conor choose to live with the team? What are the benefits of this? 4.) Does Conor believe we are in a phase of bundling or unbundling when it comes to collaboration tools? Does Conor believe we will see large players acquire and consolidate over the coming months? Why does Conor compare Roam more to Google than other collaboration tools? 5.) How does Conor think about go-to-market today? What were some of Conor's biggest takeaways for bootstrapping for years with revenue from customers? Why is Conor borrowing from the Tesla GTM? What does that really mean in practice? Items Mentioned In Today’s Show: Conor’s Fave Book: How to Read a Book: The Classic Guide to Intelligent Reading As always you can follow Harry, The Twenty Minute VC and Conor and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? Welcome back to the 20 Minute VC and Founder's Friday with me, Harry Stebbings. And I'm so excited for this episode today. Why? Well, we use this tool for all of our research here at the 20 Minute VC. It's what allows us to have the linkage and the cross-references between one guest and what they say about a specific topic, and how we cross-reference that to another question we use in another episode. That has probably given it away in terms of the company. So I'm so thrilled to welcome Connor White-Sullivan, co-founder and CEO at Rome Research, the tool taking over our industry, providing a seamless note-taking tool for network thought. As I said, I really do just love the tool. Prior to founding Rome though, Connor founded two prior businesses and also worked at HuffPost as a co-founder of HuffPost Labs, where he reported directly to Arianna Huffington and HuffPost CTO.
0:41 Harry Stebbings? I'd also want to say a huge thank you to Jeff Morris Jr. for some amazing question suggestions today. I really do appreciate that, Jeff, and Mahito is on me to thank you. But before we move into the show today, I'm sure you've heard about it, but my word, I just love this product, Carter. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund administration, so you can see real-time data in the Carter platform and work with Carter's team of experienced fund accountants. Simply go to carter.com/20vc to get 10% off.
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2:06 Harry Stebbings? But that's enough from me, so now I'm very, very excited to hand over to Conor White-Sullivan, co-founder and CEO at Rome Research.
2:18 Speaker 01 You have now arrived at your destination.
2:21 Harry Stebbings? Conor, what can I say, huge fan of Rome. And what many people don't know is that we actually structure all of our thinking and preparation for every show using Rome behind the scenes. So it feels a little bit of a fanboy episode for me, but thank you so much for joining me, Stay Conor.
2:33 Speaker 02 That's so amazing. It's a pleasure to be here.
2:35 Harry Stebbings? Well, I would love to kick off Stay and taking a slightly unusual first question, but I spoke to a little birdie before the show and they told me about a high school wrestling career where you had to learn to win. So talk to me about having to learn to win and how that impacted your mindset.
2:50 Speaker 02 Yeah, that's hilarious. So I hit puberty pretty late. So I just wasn't particularly physically strong when I was young and when I was going to high school. And I'd actually done freshman football, but had been too slow and too poorly coordinated to do anything except be on the line. But I remember the coach of the football team saying, the best thing you can do that'll get you into the best shape is wrestling. So I joined the wrestling team and then had one particular upperclassman who was just convinced I was going to quit. And yeah, I was pretty dedicated to proving them wrong and to sort of pushing myself past any limits I'd seen. But it took me two and a half years before I won my first match. There was a lot of psychological doubt, sort of not expecting to win, like going in and sort of gritting it out and making sure I didn't get pinned. But eventually I learned one move that people didn't usually see. I practiced that quite a lot. Yeah, I also
3:33 Speaker 02 put in the work and cut weight and happened to get stronger over time. And so by my junior year, I'd end up doing quite well.
3:39 Harry Stebbings? It's an incredible story of kind of persistence. Before we dive into the founding story for Rome, I guess, how do you think about that then? And how do you advise founders on the balance between really sticking to your vision and mission versus acknowledging when something could have been wrestling is not working, giving up?
3:54 Speaker 02 I mean, I think the thing is you can have the long-term vision, but then you also need to tactically be looking at how can you see yourself really clearly? How can you see where are the places where the strategy you have right now, you actually don't expect that continuing on this strategy is going to succeed. So yeah, figuring out how to maintain faith in yourself and maintain faith in your ability to eventually solve the problems that are not solvable or tractable to you today, but figure out how to make progress. And it's interesting because I'm sort of a believer in the, I guess, the power of positive thinking, like luck favors the prepared mind. And if you're going into The situations believing that you will find an answer to them. You're just more prepared to see the opportunities that are there. So there's one thing in terms of psychologically priming yourself to find the opportunities. But you also have to be able to change strategy and not be like too committed to a particular path.
4:37 Speaker 02 So it's sort of like strategic focus and like long term vision and grit. But then tactically, being able to see that there might be many different paths you could go to reach that end goal. It's a tough balancing act, though.
4:47 Harry Stebbings? That certainly rings true, though, when you look at Rome. As I said, I spoke to Mike and Anit beforehand, and they both mentioned that you've been definitely thinking about, but also working on Rome for a long time internally. What was that founding moment for you with Rome?
4:57 Speaker 02 In some ways, Rome is a continuation of the thing that first got me into tech, which was trying to solve problems of collective intelligence and how groups of people can really tap into the wisdom of the whole group, the different expertise that individuals might have, and then figure out how to make sense of a complex world and take action as a whole. So my first company, which I started when I was nineteen, was trying to do this for local governments. So we were trying to crowdsource policy proposals and to show that the registered voters in a town thought that one idea or another idea was good. And for many reasons, that didn't really work. We did end up getting acquired by AOL, which gave me some more space to keep thinking about the problem. But yeah, in a sense, this is a continuation of the problem that I've been working on for over a decade now.
5:35 Harry Stebbings? Did you go to university?
5:37 Speaker 02 I did. I went to UMass Amherst. I didn't end up graduating with a diploma for a number of reasons, but that was actually where I sort of first got my exposure to entrepreneurship. And our first company, we won a few business plan competitions there, which is where the first 10 grand for seed funding for my first company came from.
5:52 Harry Stebbings? Conor, I only lasted four weeks at law school, so do not worry at all on not getting a diploma. But I think you're far stealthier standards than me. I do want to start there because when we chatted before, you said Rome is not about taking head and nose. I guess what is it about then? And what end state you really want to achieve from the kind of the product paradigm with Rome?
6:08 Speaker 02 Yeah, so the first step of it is about thinking better thoughts, right? The way we think about it is writing is a tool for thinking. And if you can't get compound interest on your thoughts, if you can't build up a thought structure over time and continually go back and revisit it and revise it, you're limited to just what you can hold in your head. So one of the challenges I ran into when I was an undergraduate writing my thesis, which was also about the software product that I was building, was just trying to put together this like grand unified theory that was pulling from a ton of different domains. Couldn't hold the problem in my head. So the first goal for Rome is we want to make it so that you can collaborate effectively with your past and future self. So that as you read things, as you have conversations and you write those thoughts down, because the act of clearly articulating what you're thinking, it's hard to write things down in your own words. That's something that Rome is not going to be able to solve for you, right?
6:51 Speaker 02 When you read a book, most times people read a book, they forget 99% of the book a year later. But if you actually write down some of the core insights in your own words, just that action alone is going to crystallize the thought, test your understanding of it and help you remember it later. But if you can come across those thoughts and build on them later, if you can say this idea is related to five other problems that I'm interested in, that same unit of thought is reusable, you can get compound interest on your thoughts and you can solve more complicated problems in the future with less effort. But the long-term goal, right, is being able to do that also with other people, being able to build off of other people's belief architecture or other people's evidence that they found for certain things or what material was effective for helping them learn a thing that you're now trying to learn.
7:28 Harry Stebbings? Do you know what's amazing about Rome though is the fact that this next question is kind of inspired through exactly what you said there, which is kind of the correlation of ideas from the past to the present. Because when you look at Rome today as a product, you said specifically to me, Rome is simple but not easy. And so I used Rome and I thought, okay, how do you build challenge into a product? And straight away it came up my episode with Rahul from Superhuman, who said about inserting challenge into a product. And so my question to you is, how do you think about that from the product perspective? And how steep do you want to make the learning curve without being too steep?
8:00 Speaker 02 So our role model for this is Excel. Excel's got 750 million users and the phrase we use is low floor, high ceiling. So a product should have a really, really, really easy entry point. And most of the people who are using Excel, right, they're using it for like shopping lists or they want a tool for making tables and visually laying out the things they're thinking about. But then on the flip side, you have businesses that have been run for 30 years on a single Excel spreadsheet. And so in some ways, Excel is actually a better programming environment. It's a purely functional, reactive, interactive environment. And in some ways, it's better than a lot of the things we have in JavaScript or other programming paradigms. So we want something like that where it's really easy for people to get started. And as they gain proficiency in the tool and as they start to take on more challenging problems, they're able to learn.
8:43 Speaker 02 The tool and extend it and use it really as sort of a programming language for personal productivity and for personal development. A steep learning curve is a good thing because if the mountain is steep, then it takes actually a relatively short amount of time to get to the top of it. It takes a lot more effort, but you can get pretty far, pretty fast. And so that's kind of what we want is that there can be slow paths up the mountain. And there can also be like deep paths up the mountain where someone can gain a lot of power quickly.
9:05 Harry Stebbings? Can I ask, did you think about doing the superhuman style of onboarding to really make that steep path up the mountain? A little bit more gradual and kind of hand hold the way to maximum efficiency with the product.
9:15 Speaker 02 Yep. When we first launched, we did require every person who came in to go through a onboarding call. But we weren't charging from the first day because actually we wanted to be able to lean on end user innovation and see how people were using it. And so we wanted something a little bit different than the way superhuman runs things. And I still do every Tuesday, basically from 10 a.m. to 7 p.m. I'm on user calls. So I'll do a lot of 30 minute onboarding and at some point we will scale a customer success team and do those more at scale. Cause currently I'm backed up for the next month. So we have done that, but also because Rome is what you make it. Like it can be a very simple tool that you're just using and doing daily journaling and taking some meeting notes. And you're occasionally using some of these bidirectional links.
9:54 Speaker 02 You were discussing earlier how when you have an argument with somebody, you're able to pull up points that had come up in previous conversations from someone else. Right. That's definitely a power user use case where you're actually mapping out different arguments and different discussions you're having. Or you're using it as a sophisticated personal CRM or using it for project planning or those kinds of things. It's been really great that we've got such an active community that is making so many, like sometimes full courses on teachable or full courses even just on YouTube, showing people different ways of using the tool, some of which we hadn't even thought of. So if you don't have to do the superhuman onboarding, it is usually better when people are coming through a friend and that friend is giving them their own sort of opinionated approach to Rome. But there's many ways to do things in Rome. So we don't want to force people into just one single way of thinking.
10:35 Harry Stebbings? You said about the incredible kind of community around it and absolutely I've seen some of those videos and it's always a sign of like true customer and product love. I guess my question, and actually I have to give full credit to Jeff Morris Jr. For this, but his question is, how do you build a software cult like you have done with Rome?
10:49 Speaker 02 I mean, you talked to some friends of mine who've seen me working on this for five, six, eight years in the, in the. Idea space, a long time of that I was silent. Like, there was a time where I was like, living in a van and working at the top of a mountain, and I went to India for a couple of years. And I didn't have quite the same engagement with a community of people that were like-minded. But I guess it was about a year ago, I decided to start using Twitter the way that I use Rome. So using it as like threads of threads, like reusing my old thoughts, creating a maze that people could go explore. And the way I started was just being pretty angry about the state of existing tools. And like, why Evernote is a terrible second brain? And just not a good place for organizing your ideas or building up a repository of research. And also talking about other systems, like there's a system that we're a big fan of called Zettelcasten. Unfortunately, there was a book that came out recently called How to Take Smart Notes,
11:34 Speaker 02 on how to implement this, even just with pen and paper. And so we started talking a lot about those, or I started talking a lot about those, and getting into some fights on Twitter with people who thought Evernote was the greatest thing. And that really you just needed the right discipline and enough process, and you could make Evernote work for you. And for me, that's fundamentally wrong. Evernote's not built the way your brain is. And a lot of the friction that you have with reusing thoughts in Evernote is incidental complexity, because they follow this files and folder metaphor from an archaic time. And so, yeah, I've been pretty loud and opinionated about the principles that I stand by and what I think is true, and just sort of put out a frequency. And some people resonate with that frequency, and some people don't. And I think just holding to that integrity attracts people who notice that like, oh yeah,
12:18 Speaker 02 like, I've had the same frustration, I've felt the same pain before, and I want to be part of this different future. So I think that's part of it, is just being pretty articulate about what we think is true, and some people love it, and some people don't.
12:29 Harry Stebbings? Totally. I think it's almost like a mission statement. And the worst mission statements are the ones which kind of everyone agrees with. Do you know what I mean? It's divide.
12:35 Speaker 02 Yeah, there's something that's pretty amazing about having a nemesis. And for a long time, my nemesis has been Tiago Forte, who runs the Evernote. I say he's trying to make Evernote great again. And he's got some really good ideas about knowledge management, but he is committed to being tool-agnostic, and saying like, oh yeah, all tools are the same. But I think that when the tools introduce this unnecessary friction, right? Like, thinking about what file does this note need to be in? Or like, what folder should I put that file in? It doesn't allow for reuse in the sort of fluid way that I think you need to for a thinking tool. But yeah, like, that fight has also just been a great thing for us in our founding moments.
13:07 Harry Stebbings? No, absolutely, it hasn't. It's always been entertaining to see. In terms of kind of the cult-like element, you know, go-to-market's always crucial. And when we tried it before, you said we have the Tesla go-to-market. I'd love to dive into this. What did you mean by this? And how does that mean you think about kind of go-to-market moving forward?
13:20 Speaker 02 Yeah, so Tesla's business plan was build a sports car, use that money to make a more affordable car, use that money to make an even more affordable car. And for the many years that I was working on Rome, it was a pretty unfundable idea. I had some great friends who were investors or who knew a ton of investors, but everyone was like, well, isn't this just competing with Evernote? Isn't Evernote sort of a dead unicorn? And so the way that we were able to run the company, we were very, very fortunate. And also, we made some decisions. I looked into what would be the ideal early user base. Who are some people who are thinking a lot about thinking, who are open to different kinds of habits and workflows that aren't supported by any existing tool? And who are going to be willing to learn those because the problems that they're facing are so complex that they needed a better system, they need a better tool.
14:02 Speaker 02 And so we actually got off the ground by getting customer funding from some folks in the Effective Altruist and particularly the AI safety community, people who were thinking about AI risk. And I would say like the broader Bay Area rationalist community. And so people who were really thinking about how they think and how do they figure out what is true? And how do they process their emotions as well to deal with the biases that are inheritance from our ancestors? And so our go-to-market was really a handful of these organizations that paid us sort of an enterprise license where we were working really closely with the researchers. And as long as we were building features that they wanted or that they would use, we'd keep getting the contract extended for another month. And that lasted us for really the first two years of the company and allowed us to build from something that was really quite complicated and wasn't really intuitive, wasn't really easy to learn.
14:47 Speaker 02 But these researchers had enough pain and saw enough potential that they wanted to keep using this really early version of the alpha. And that got us to the place where we could actually launch. And then from there, Rome, it's really different. I have a lot of respect for Ivan and Simon from Notion. I've met with them a bunch, but their approach is like, it's got to be really intuitive for every user who comes in. Let's play to the lowest common denominator. You shouldn't really have to change your way of thinking to use Notion. And we take the opposite of approach. So our strategy has been, let's go to the people who are willing to learn to use a power tool. And then many of them are Writers or their investors or their founders or CEOs. And so there are a lot of people who aspirationally want to think like those people. And when they see that someone is having success and they're writing more, they're feeling more on top of their game for running their company or for making their investment thesis or like you,
15:33 Speaker 02 they're able to run a better podcast, they're able to ask better questions, they're able to pull up better insight. All those things really help drive the next wave of users who often then have a bunch of people who look up to them. And especially when you see people starting to produce more output. There have been people who've said Rome's the reason they didn't drop out of their master's thesis. Or like Rome allowed them to suddenly take their SubSak and make it something that's paid because they're producing three times as much with the same amount of effort. Those sort of testimonials then drive the next wave of adoption. So that's the way that we look at it is starting with something that is sort of for like elite intellectual athletes, but then make it accessible and make it something that other people can learn to and grow into.
16:06 Harry Stebbings? Listen Conor, I adore Rome. I don't think anything would have kept me in that legal degree. I have to admit, but I do want to ask, you mentioned the product there and we really delved in there. In terms of the team building the product, when we spoke before, you said something really interesting. And you said, I hire for grit and auto didacts. So how do you think about your hiring philosophy? And I guess, how do you really stress test those two in reality?
16:27 Speaker 02 So I spent a really, really long time founder dating for this company because I knew this was my life's work. My first company, we had a small exit that gave me some financial freedom to go live in a van and work on this and not have to worry about a paycheck for many years, which is great, but this is the project that I want to be doing for the rest of my life. And so I wanted to be really careful about who I brought on to the team and who was somebody who I wanted to make that sort of lifelong commitment to. And actually, I was still in India at the time. And I remember hearing about 42, which was a tuition free, peer-to-peer coding university that was funded by a billionaire in France. And I saw Paul Graham tweet about it saying, you know, this isn't another coding bootcamp, this is another MIT. And their filter processes, you know, there's like a two hour long online test that you take that's basically just a logic puzzle, sort of feels like an IQ test. But it's also a test to see, will you keep going
17:12 Speaker 02 all the way through the two hour time limit? Will you actually like keep doing this hard thing and have that dedicated focus for two hours? And once you get there, you get invited for a month-long application process, which in the batch that I was in had basically a 70% attrition rate because you're Teaching yourself C, there's no teachers, there's just some YouTube videos and a incredibly onerous machine grading system that will fail you for the whole day for, you know, a syntax error. And so there's a lot of emotional pain that people go through as they're trying to teach themselves a new programming language and also having this rough grading system. And I met my co-founder there because he was the one who was up at 4am in the lab. And he was able to teach me a bunch of stuff. And so he had the communication ability, he was like clearly amazing self-directed learner.
17:56 Speaker 02 And he had dropped out of college as well because he wasn't impressed with the seniors in the engineering program he was in. He didn't see like, hey, if spending four years makes me like them, I don't want to do that. And he went out to 42 because someone told him it was the hardest thing they'd ever done. And that attracted him there. And the fact that he was seeking out the hardest possible challenges, the places for peak growth. And then he ended up having the fourth highest score in the history of the school when he graduated. But more importantly, it was his work ethic and his sort of drive for continuous improvement. So that for us, that's sort of what we look for in everybody is like, are they the kind of person who's going to be able to go through the dark night of the soul when they're working on a problem that hasn't been solved before? And are they going to be able to maintain faith and keep pushing themselves to their limits? Hire for talent, train for skill. We wrote it in Roman closure and there's a lot of reasons for that.
18:39 Speaker 02 But when I first made him the offer, the first offer I said is like, well, you just taught yourself C in a month. If you can teach yourself closure in a month, I'll give you a job. And he learned it in three weeks and then made him an offer to be a co-founder like maybe three or four weeks after that. Cause he was so fantastic.
18:51 Harry Stebbings? I do love that as a story. It's an amazing to hear the relationship there, but it's also amazing because you do also choose to live with the team. So Mike told me about this. Why did you decide to do this? And what do you think of the benefits of living with the team?
19:03 Speaker 02 I mean, it's a family, right? I mean, for us, it's like, this is much more than a business, right? This is the future that we want to see. I want to build this graph of the world's knowledge so that my kids don't ever have to go to school. They can learn the things that they want to learn and find peers and find mentors and establish credentials based on the quality of their work. I think that maybe this is also part of the reason there's this sort of cult behind it is like Rome is a philosophy. It's a belief about how the world should be. So we try and put that kind of thing into practice and have an orientation towards truth seeking in our personal relationships and everything. But just having those like really close bonds and having all that time to know each other. As full people. Now we're growing the team. We currently have one of our first hires. He was brave enough to brave the airports during the pandemic and come out here and stay here for six weeks.
19:46 Speaker 02 But we are going to be primarily a remote company, but it's still great to have people come out and stay for six weeks or a month. And just like really get immersed in the culture and for us to just be able to know somebody as a whole person and know like, what are they wrestling with personally and just have those kind of bonds. Cause I believe in, we can do a lot with a pretty small core team and it's good to know people for the long haul and be invested in them for the long haul.
20:06 Harry Stebbings? Totally. You said about kind of mapping the world's knowledge down, kind of the ability for your kids not to have to go to school in some respects. I guess people kind of compare it to Evernote.
20:13 Speaker 02 In all respects, in all respects, yeah.
20:16 Harry Stebbings? But people compare it to Evernote, to Notion, to other tools. And would you argue that actually Google's a much more comprehensive comparison in terms of mapping the world's knowledge?
20:24 Speaker 02 Guillermo from Zeit tweeted that he felt like us and Notion had a better claim for mapping the world's knowledge. Yeah, I think there's something to be said that Google set out to organize the world's information. And now they're organizing all the information about their users to serve the perfect ad, which is not the same thing. We think a lot about research is actually, you know, not just search. Search will give you a single answer to one question, but it won't give you a path of like, here are all the questions you need to ask along the way to reshape your questions or like reframe your question. Here's the path to get from where you are to where you want to be. It's a much harder process and it's one that requires, you know, you have to know where the user currently is. And so for us, what we want is a layer on top of the web of each individual's personal brain.
21:04 Speaker 02 And for them to be able to share parts of that with the whole public, the whole world, parts of that with some of their friends or certain collaborators. And to be able to have basically a read, write web, a web where if I see a connection between two documents, even if I wasn't the original author of those documents, somebody else who has those two documents in their database can discover that I've connected them. Or someone who's reading something can see, if they're friends with me, they can see that I've drawn a connection. So yeah, that's the future that we want to have is one where it's not algorithms that are determining how the world's information is organized. Those can be helpful, but AIs are statistics machines. Well, we're interested in how does someone at the margin, who's the first person who ever saw a connection between two things, way before an AI can see that connection, like how can they make that connection explicit so that other people can follow their path?
21:44 Harry Stebbings? We mentioned those tools earlier and I kind of find it clarifying often things about kind of the binary statuses of bundling or unbundling. When you look at kind of the collaboration tool space today that we mentioned and that people I think probably wrongly put you in. Do you think we're in state of bundling or unbundling when analyzing that market today?
22:00 Speaker 02 It's interesting because I've used and I've seen other people use all sorts of tools for organizing their thoughts. Like they'll use their Kindle highlights and then maybe they've got some dedicated software for reading PDFs and for building mind maps of the papers that they're reading. And then using something like Figma for laying out a bunch of thoughts, digital whiteboarding, all this stuff. But none of them have a paradigm of like reusing ideas in different contexts, taking the same data and showing it in different contexts. So I think sort of moo, like not yes, not no, right? Like in some ways, it's the wrong question. I think Notion's done a pretty great thing of saying, hey, actually you want your notes and your tables together. You want your Airtable to be, and Airtable's also working on notes as well. But if the underlying paradigm of all of it is not one that's generic enough to fit the domains that you're thinking about. That's one of the reasons we're so bullish on graph databases is that they're a better representation
22:45 Speaker 02 for the relationship between thoughts, the relationship between projects, the relationship between people. And yeah, most of the tools that we have out there are based on the SQL databases and like tables and rows. It doesn't have the same kind of structure. So yeah, we're starting to see some rebundling, but I want to live in a world where I can take the same information and view it in multiple different ways, interact with it in multiple different ways, but be able to always reuse the information that I got from one application in a different context, in a different view, like when the problem is slightly different.
23:14 Harry Stebbings? Listen, I totally agree. What a shit question. Terrible question. Hit me, hit me, though.
23:18 Speaker 02 You can get away with a lot because of your accent. It's great.
23:21 Harry Stebbings? Honestly, people either think I'm Harry Potter or Benedict Evans, so I'm totally winning either way. I do want to move into my favorite, though, Conor, which is a quickfire answer. I say a short statement and then you hit me with your immediate thoughts in like 60 seconds or less. Are you ready?
23:34 Speaker 02 Sure. If I ramble, you gotta give me the buzzer.
23:36 Harry Stebbings? I'll give you the buzzer. Okay, so favorite book and why?
23:38 Speaker 02 How to Read a Book by Mortimer Adler. It's an algorithm of thought that changes how you read all other books. It was definitely very influential for Rome. You don't want to waste time on bad books and for really good books, you want to give it a much more thorough reading. And How to Read a Book is the guide to an auto and ad act continuous education, classical liberal education. It's fantastic.
23:57 Harry Stebbings? What's your superpower and then your weakness in company building? Thirty seconds on each.
24:02 Speaker 02 I guess like maybe some combination of like wild vision and grit. I think that being able to clearly picture a future that I want to live in and communicate that and find the other people who believe in it has been great. And then I'd say probably one of my weaknesses is just organization, right? That's why I needed to build Rome. I'm pretty ADD and have a million thoughts and it's hard to get them into a great process and into a great structure. So I try to build a prosthetic brain to make up for the weaknesses of my first brain.
24:27 Harry Stebbings? What would you most like to change about the world of tech and startups today, Conor?
24:31 Speaker 02 I think that for all the talk of black swan farming, a lot of it's really bullshit. I mean, it's been amazing to me how many people want to invest in Rome now versus how few wanted to a year ago, when like $10,000 would have made the world of difference for us. So I would like to see actually just like much larger investments in people who had actually risky or ambitious ideas that were pretty far away from having traction. So I think that that's something I would like to see is like more small investments in much larger arrays of problems.
24:58 Harry Stebbings? Who was the first check into Rome and how did it come about?
25:01 Speaker 02 First check was a guy named Richard Meadows, who's famous for eating only pizza for a year. He's a business journalist and I had been trying to build sort of a framework for autodidacts, sort of a secular religion or like a learning cult, as we called it during the time where I was prototyping Rome stuff. And he actually came to a retreat in Mumbai and he's a writer and got interested in the Zettelcast and thing and he played with a very early prototype that I had. And he was the first check into Rome and he's a great friend and helped us write the white paper later, you know, a year and a half later, helped us write the white paper. Maybe it was actually only six months after we invested, but yeah, he was the user of the product.
25:36 Harry Stebbings? What a story. I do have to ask, when I say success, who's the first person that comes to your mind?
25:41 Speaker 02 Jesus Christ.
25:43 Harry Stebbings? I was going to ask why, but I think it's probably fairly obvious on that one. Okay, hit me, this is the toughest of all. Next five years for you and for Rome. Actually, there was an interesting one that was posted on Twitter. When you think about the most ambitious vision possible for Rome, what would that ambitious vision be?
25:58 Speaker 02 For us, I don't know whether five years is tractable for this, but when I think about the long-term vision, it's some kid in Somaliland or Turkmenistan or wherever is able to, without ever going to To a school, learn all the things that they need to learn and reach a point where they can actually win a Nobel Prize or a Fields Medal or in a less ambitious thing, you know, get a job at whatever the SpaceX is of that time, just on the merits of what they have contributed to the global knowledge graph and have a replacement for the existing institutional financial system and that. But I think, in the short term, I think the way that we do peer review research is fundamentally completely broken. The way that we store the accumulation of all of our civilizations' knowledge in PDFs that are hosted by Elsevier is just wrong. And so that's in terms of long-term ambition,
26:42 Speaker 02 I want to make it possible for people to chart an efficient path to the frontiers of knowledge and then push that frontier further.
26:47 Harry Stebbings? Conor, as I said, I've been such a fanboy of the product for a while now. As I said, it structures all of my thoughts and allows me to keep friends but also put my arguments across. So thank you so much for saving my social network and I've so enjoyed this.
26:58 Speaker 02 This has been fantastic. You're exactly the kind of person who we, you know, you're talking to tons of brilliant people and the fact that you're able to reuse that knowledge and use it to push thinking further, you're a perfect user. So I'm very thrilled to hear that you've been using it.
27:14 Harry Stebbings? I have to say, I did just love that discussion with Connor and I just couldn't be more excited for the time ahead with Rome Research. And if you'd like to see more from Connor, which is a must, you can find him on Twitter at Connor, that's C-O-N-A-W. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at HStebings1996 with two Bs. I do love to see you there. But before we leave you today, I'm sure you've heard about it, but my word, I just love this product, Carter. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund administration, so you can see real-time data in the Carter platform and work with Carter's
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28:41 Harry Stebbings? Hims, all trusting Terminal with their remote teams. And you can find out more today at www dot terminal dot io, that's terminal dot io. As always, I so appreciate all your support and I can't wait to bring you a fantastic set of episodes next week.
Previous 20VC: Mark Cuban on His Relationship To Wealth and Risk, Why Coming Out of The Pandemic Will Be The Best Time In The History of Mankind To Start A Business & Why Silicon Valley Investors Are Like Old Hollywood Next 20VC: Floodgate’s Mike Maples on 3 Key Breakthroughs Startups Experience in Success, The Rise of Angel and Operator Funds, Multi-Stage Funds Re-Entering Seed Investing and The Insight Development Framework Page updated October 26, 2026 · transcript and summary are machine-generated