From VC to Builder: Building the AI Tool Shaping the Future of Work | Nick Adams
Kazuki Nakayashiki
May 7, 2025 9:04 PM
Summary
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Introduction of Guest (00:08-00:31): Nick Adams, a seasoned entrepreneur and investor, is introduced. He is the founder of Quill Meetings, a platform designed to enhance meeting productivity, and a venture partner at AME Cloud Ventures.
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Inspiration Behind Quill (01:02-02:40): Nick shares that his journey towards founding Quill Meetings began after exploring AI capabilities, particularly the advancements of GPT-4, which inspired him and a co-founder to create a better meeting scheduling and note-taking service.
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Unique Features of Quill (04:48-06:58): Quill Meetings focuses on generating insightful notes from transcripts in multiple languages. It distinguishes itself by operating locally, prioritizing user privacy, and integrating advanced AI technology to enhance user experience.
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Comparison with Competitors (08:12-10:35): Nick discusses how Quill Meetings differs from other note-taking apps like Granola, particularly in its ability to support multiple languages and maintain data privacy compared to larger, more established platforms.
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Nick's Transition Between Roles (17:57-20:20): He reflects on his experiences as a venture capitalist versus being a founder, noting the excitement of building a product and leading a company, while also acknowledging the valuable insights gained from observing numerous startups as an investor.
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Fundraising Perspectives (49:02-51:59): Nick shares thoughts on the changing landscape of fundraising, stating that while a smaller team can be more efficient, the reasons and methods for raising funds have evolved, especially in the wake of the AI boom.
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Legacy and Impact (58:11-1:00:32): Nick expresses his desire to have a positive impact on people through his work at Quill Meetings, emphasizing the privileges of building products that benefit users and contribute to their experiences.
Transcript
Hi, everyone. Welcome back to another episode of Glasp Talk. Today, we are so excited to have Nick Adams with us. So, Nick is a seasoned entrepreneur and investor, currently the founder of Quill Meetings, a platform transforming how meetings are run by making them truly work for you. And he also serves as a venture partner at AME Cloud Ventures, where he has spent over a decade supporting visionary founders in the data-centric world, with deep ties
to Jerry Yang, the co-founder of Yahoo, and his investment network. And with a robust background in international business development, product management, and startup leadership, and including co-founding tech ventures like EnTrip and evoleas, Nick brings a wealth of experience, bridging east and west in the tech ecosystem. And today, we will dive into Nick's journey through Silicon Valley and beyond, his insights into startup innovation, and how he envisions the
future of productive collaboration. Thank you for joining. Thank you so much for having me, guys. I'm really happy to be here. Thank you. So, first of all, you're a co-founder of Quill Meetings, and we want to know what inspired you to start the company, and what problem are you aiming to solve? Yeah. So, what inspired me was a friend and I, who is now my co-founder, spent some time hacking on projects together over the summer of 2023.
I was actually interested to go into Hollywood and pursue a career in drone videography in 2023, but then GPT-4 came along. And in April 2023, GPT-4 was quite a big moment for the world. It was the moment when the world said, okay, these are not just text generation bots. They start to look like they can reason a little bit, and it got very exciting. So, for years before that, I was working on a product internally for myself at AME that did meeting scheduling.
So, I was using regular expression-based simple decision trees to decide what people meant when they set a time in their meeting, and figure out how to schedule a meeting with them without me having to type an email reply, because I did a lot of meetings as a VC. And so, when GPT-4 came along, I was interested because it felt like, for the first time, you could do this with proper AI without having to train your own model.
And so, a friend and I were equally passionate about the possibilities of a powerful model like GPT-4 with open access, and we started hacking on a project over the summer of 23. And the project itself, we never really felt like was ready for production and ready for customers. But towards the end of the summer, I attended YC Demo Day in September 23, and I took audio transcripts, just basically audio recordings of some of the meetings that I had, and I put them through a local version of Whisper.
And Whisper is an open AI-released, open-source transcription module, and I was blown away with results. I did not realize that you could transcribe audio into really quite accurate text locally on your Mac, and that blew me away. And that, in conjunction with the new LLMs that were coming out at the time, like CLAWD2, meant that you could take the transcripts and you could throw it through an LLM and you suddenly get notes that were better than any notes I'd ever taken on a startup.
That was exciting because it felt really empowering. This was a technology that was suddenly within arm's reach of millions and millions of people that it was never before. And so Mike and I decided to form a company around it, and that's what we do. We basically use Whisper locally. We transcribe audio into text, and then we use CLAWD LLMs in a privacy-centric way to turn it into really great notes and other kinds of outputs. So that's how it started. Yeah, I really love it.
And I've used it, and what I like is you transcribe what we are talking about in the meeting and summarize later, then create a to-do list if we need, and then automatically I can chat with my notes, and that's a great UX, and I think I love it. Thank you. Our philosophy, when you take it up a level, obviously my motivational reasons for starting Quill were on the technology level, but if you take a step up and talk about the more visionary level, obviously there were a lot of
note-taking competitors when we started already. However, they were really focused on transcription and not really great notes. And so we started Quill with the idea that the transcript isn't as important as what you do on top of it and all the things you can generate on top of the transcript. And so Quill's entire user experience and UI is built around the idea that you have a meeting, which is effectively the source of truth, which is the transcript, but then on top
of it you can do lots of cool things cheaply, fast, and very high quality. And so yeah, we are basically an LLM-first note-taking company, and being local means that you don't need a bot in the meeting, and it also means that all of the data and audio stays locally, which we really love. So we are unique in that respect, and we just think we are the best note-taker as well. Obviously a lot of people will say they're the best note-taker, but our customers speak for us,
they flock to us, and we're growing fast, so I think we're doing something right. I think so, yes. Thank you. And at the same time, nowadays so many AI tools and note-taking apps, and also audio transcription services, and one is Granola, and it's AI note-taking app, and I think they are in a similar space, I guess. But what I realized was the difference between Quill Meeting and also Granola was like, in case of Granola, when I speak in English,
when I speak in English, they transcribe, but when I speak in Japanese, because I speak Japanese, and they don't transcribe, so that I cannot track what I'm talking in Japanese. And sometimes I join a meeting, you know, sometimes we speak two or three languages, and they don't take notes, but in case of Quill Meetings, even if I speak Japanese, other languages, it takes notes and then summarizes data, and then I can see transcript,
and that's what I was so impressed in. Thank you. Yeah, thank you for that. I mean, we think about it in terms of how can we build the best possible product, and for us, building the best possible product means that for all kinds of different people in different circumstances, the product just seems to be magical out of the box. It's very difficult to do that well, because you have to think about all the different ways people
are going to use your product, and, of course, with meeting transcription, language is one of them. It's, yeah, it's not trivial, some of the stuff we do. Whisper does support different languages, but we also do clever things to figure out which language you're speaking, and, in fact, just last week, released automatic language detection, so we will, even during the meeting, switch the language of transcription, depending on what you're saying.
And to do all this, and not only do it locally, not only do it well, but also locally, is not trivial, but ultimately, we hope the customer just feels like the product works great, and that we can deal with all that technology stuff, so sometimes I get a bit carried away, you know, talking about the technology and getting excited about what we've built, because it is difficult, but ultimately, we do all this so that our customers don't have to worry
about it. I see. And at the same time, this is kind of another question. I don't know if you can talk or share, but, you know, since you are the now currently board observer at Zoom Video Communications, right, and seems like Zoom is also in, oh, by the way, we are using Zoom, but we are in the similar, I mean, Quill and Zoom are in a similar space, right, I assume, and, no, maybe no, but I wonder, you know, if you can, even, how to say, be in the board of Zoom,
and can you start a company, or, because, yeah, I was wondering if it's okay for the company. Oh, I'm not on the board anymore. I left the board when the company, when Zoom went public, Oh, okay, sorry. Yeah, yeah, no, no, yeah. This would be a conflict, for sure, if I was on the board. No, I left the board a long, long time ago. Eric and I remain in touch and we're friends, but I watched the journey and was basically along for the ride for most of the years I was on the board.
I learned a ton from Eric, and I hope that I was able to provide some value somewhere, but the journey was incredible. We invested in Zoom in December 2012, and watched as they grew very fast, and even then, people didn't really know the name until COVID, but Zoom was an amazing journey. It's a naturally viral product. Eric's done very well there, and I think the product is amazing, and the technology is amazing.
The space-wise, I think all these products, even like Otter and others, have tried to bolt on note-taking and done it and tried to do it well, and I'm sure they're all evolving all the time. We've started the products from the ground up to be LLM first, and to be very modern and feel like magic right away, and we approach it from a slightly different perspective from Zoom. From Zoom, they're trying to create a product that deals with all the notes you have within Zoom, and that makes sense, but a lot of meetings happen outside of Zoom,
and a lot of people's lives are in real life. They're in conference rooms. They're in Teams and Meets and Discord and et cetera, so there's a lot of different ways people pull in audio and conversations, and Zoom will cover some of those, but won't be able to cover all of them. the way we can and also bring people together to a product which is just about that. Whereas as soon as you start adding features onto a product like Zoom, you have to dig around to find
what you want within that platform and probably the user experience isn't great anyway once you're there. Whereas for Quill, we're all about just doing that one thing really, really well. So there is some overlap. There's a lot of overlap with a lot of companies, but I think that we found our niche doing notes and local notes really, really well and for all platforms. So I think that's the differentiation.
Yeah, thanks. And I'm curious, why did you start with desktop application? Because local and privacy are important, but at the same time, letting user install desktop application and spread it is pretty difficult in terms of growth. So how do you think about it? You can grow it later even if it's a desktop application or do you have a plan to make a browser extension or web application that works on the browser? Good question. That's a really good question.
When we think about the products, we wanted to create the best product possible and we could only create the best product possible when it was a standalone app. On top of that, some of the transcription stuff we do, it isn't possible to do in the browser. So that's another reason. I think these days with AI, it makes more sense to install a desktop app. You noticed OpenAI have an app, so does Anthropic. And increasingly, these apps are starting to use tools on your computer.
I believe that the way we're going is more and more tools and useful products will be desktop apps, standalone apps in the AI world. They're right in front of you at all times and easy to use and don't require you to open a browser tab and navigate to a SaaS website. And yeah, I do think the security aspect is huge. Not everyone cares about it, but some enterprises in particular really do care a lot.
And so for them, this architecture actually makes a lot more sense to them. So there are obviously positives and negatives, but we are not seeing that it's causing an impediment to growth. I think people are willing to install an application if it gives them a lot of benefit. So yeah, but it's a good question. Okay, thank you. And so eventually, so local LLM works on the desktop application. So is that your vision? Yeah, let's see where things get to. The models that are out now, they can generate sort of bad notes slowly.
So we have two things to figure out. We need to get the models that can run locally to create really great content. And it needs to be equal to what's in the cloud. Because ultimately, I think people will prefer to get the better notes than the more local notes. And so there's that. And then on top of that, it's got to run fast. So it can't be generating 10 tokens a second, it has to be generating hundreds, if not more tokens a second.
And the third thing is it has to work on most people's computers. And so in this case, I think we're going to wait a while for this. But we're always looking at the newest models and trying to figure out if there's something there. We are going to have something exciting in that respect later this year, though. So you can stay tuned for that. We are working on ways to enable people to use local models if they want for the LLM side.
Did you launch it like TechCrunch or BigLaunch or something like that? Oh, I see what you mean. I see what you mean. We haven't done a lot of big launches. We're really spreading by word of mouth. We haven't done a lot of press. We have some LinkedIn announcements. But yeah, no, the product is not in beta. It's out. But we haven't done a lot of things yet. Yeah, yeah. Okay. Do you have plans to public BigLaunch? I think the way to launch companies these days has changed.
I don't think it's all about one big launch. I think you need to continually throw out announcements and launches of products or features. And that's how you get sort of rolling thunder attention. That's my sense. So we sort of constantly have plans to do that. But we're not going to have like one big launch, I don't think. I see. Yeah. And I think that makes sense because I remember Andrew Chen once published a post about always be launching. Nowadays, BigLaunch one day doesn't work.
So you should always be launching something so that people remember about your product. And I think eventually they start using it or something like that. That's right. Yeah, that totally makes sense. But for the current growth and how and who are you using your product or who are referring to whom? Could you tell us a little bit about your current user growth scene? Yeah, we built Quill to be a general tool for all industries. So it's both a blessing and a curse.
It's a blessing because it means anyone can go ahead and use the product and get a lot of value from it, whatever you do in your life. But it's also a curse because there's less focus. I think we're finding a lot of growth in areas like executive coaching, recruiting, sales and marketing, as well as obviously founders and solopreneurs and VC finance. So there's a whole bunch of different industries where you get a few users and they get excited
and they share it with other users in that industry. And that's happening in quite a few different spaces right now. So that's the user base. But have you found or figured out any interesting use case or you didn't expect? Oh wow, there's an interesting use case or something like that. Yeah, I will tell you one thing. This is a slightly different answer, but I think it's an interesting point.
We are finding that where we thought verticalized players, verticalized solutions would beat us, we're finding that companies are still adopting us. And I find that fascinating and very encouraging. I think it's because they realized that Quill is much more powerful than just a workflow around one industry. So I can't give the name of any particular customer here, but let's talk about potentially recruiting.
In recruiting, you'd expect that there's a workflow company around note-taking that just does everything related to ATS and recruiting. But imagine a customer that decides to go with Quill eventually, potentially, because they prefer that their users actually have a more generalizable product that can do all kinds of different things for their internal team. So I really think of Quill as a product that's kind of the future of the way we work, as much as it is a note-taker. And it's encouraging to see that our customers agree.
We've got another big enterprise customer where I thought they were just on board their sales team because the sales team are the ones having all these conversations with external companies. In fact, they onboarded the entire company and then grew fast and everyone in the company now uses Quill. And I find that just really encouraging. It feels like we're building a product that's more about the future of work than it is just about note-taking from a Zoom call.
Right. I see. Switching the topic to your career and VC part. And you were the managing director at AME Cloud Ventures, right? One of two, yeah. Yeah. So you were an investor and switched to founder. I mean, started with founder and VC, founder. And which is your preferred role? You see different things. As an investor, you see a lot of startups and what's happening in the market. As a founder, you focus on one thing.
How do you see the difference? It's fun. Both are fun. Both have a lot of advantages. Both are privileged careers in different ways, right? It's a great privilege to build a company. It's also a great privilege to invest in companies. My sense is, the cool thing about being VC is you get to meet a lot of people and you get to see some of the best people in the world doing what they do. And that's such a privilege. So you're always pushed.
You also see 5% of what you invest in, even companies that you do invest in, end up telling the future. So you kind of see into the future too, which is nice. And I like that. The problem with being a VC is, as a builder, I've always been a builder. So I've been hacking on my own projects. I learned JavaScript and PHP when I was in college doing electronic engineering. I was more interested in building things. And for me, the web, as it was then web 2.
0 or the beginning of dynamic websites in early 2000s, was more exciting to me than electronics because I could see what I was building. And so as a builder, being a VC was challenging at times because all you can really do, you're kind of like a coach, right? You're on the sidelines. You're watching the players play. And it's kind of fun to watch them play, but you're not on the pitch. You're not feeling the ups and downs in the same way. And you can shout and scream all you want.
And hopefully they're not listening to you too much as a VC, but it's not the same as being on the field. And I think that's the, for someone who likes creating things and likes playing the game, that was always a little bit of a disadvantage. But I did have a lot of side projects. I built the CRM for us internally at Ame. And I also built this scheduling bot I talked about at the beginning. And so I found ways to get my creative outlets and to build things. But being a founder is different.
This time, it's more involved than the first company I started where things are working better. So there's more work. And there's a lot of building which is fun but there's a lot of other things and there's a lot of ups and downs and I definitely last year it was quite cool to sort of realize I worked harder last year than I think I had done in my entire life and that was kind of both a bit scary and draining but also exciting for me so yeah there's advantages to both I think and I'm enjoying the journey and maybe one day I'll
go back into BC. Interesting, so then how did you decide to join AME Cloud actually? I was I'm curious about you know the story behind why you joined, what happened, and Jerry and Richard to you or yeah I was curious. Yeah that was honestly just pure luck. I came to Silicon Valley in 2012 and with my partner and the idea for me was to go and work in product management. I wanted to learn a new trade. I hadn't really done product management.
I'd built a company before but not sort of proven product person so I came to Silicon Valley and started looking for jobs. We didn't know anyone. We had a few relatives locally. I started applying and getting rejected by a bunch of companies. I was interested in working in clean tech. I was probably at the tail end of that being a good idea and the person I was working for in China at the time when I moved here had me do a little bit of consulting with him and introduced me to Jerry who he knew
and so I met Jerry with a few other people in an afternoon and it was fun. We just talked about big data back then. Big data was big. It was 2012 and you know Hadoop had just started, spun out of Yahoo and you've got kind of the cloud is beginning to really take shape. It was three or four or five years after AWS and people were building big data systems and they were taking the they were taking the systems that had been built as ad tech backends within the large tech companies
like Google and Yahoo and they were going out and turning them into data lakes for companies and turning them into enterprise companies. So that was an exciting time and we were talking a little bit about that and then I went to actually Mike's wedding, my co-founder's wedding in Ohio and it was early September or late August 2020 and I got an email from Jerry that I'll never forget. He and I really did not expect this.
I had this sort of vague notion that I might do something as an angel or as a VC in Silicon Valley but I really didn't expect it or want it necessarily. He reached out to me and said hey look while you consider your opportunities in Silicon Valley why don't we talk about how you could be helpful in what I'm doing. You know I was kind of blown away by that email and we went and had a chat for an hour and a half just he and I in his office and after that I remember I still remember that day.
I went to watch the Dark Knight Returns after that. I have a vivid memory of that entire day because it was obviously the first time I'd met one-on-one with Jerry. It was a lovely chat for about an hour, an hour and 50 minutes and after that he said just come hang out in the office and you know give yourself whatever title you'd like and he's like he asked me what I got paid when I was in China and it was very little and he gave me more than that which is still very little for my age but I didn't care at all
and I hung out in the office and started doing stuff for him whatever he wanted right and that was how it started. I think I was incredibly fortunate. I think part of it was I had some experience in China and I did speak Chinese and maybe I'd been a builder before. He liked people who were technical and understood the product and technology side more. I have no idea. I've never asked him to this day why he decided to hire me.
I do think he thought it was a good idea after a few years because we did do some cool things together so I'm pretty sure he wouldn't say he regretted it but I don't know why initially he had that feeling and I'll always be thankful and feel incredibly lucky about it. But you're still in touch with him right even after you left. Yeah I mean he's an investor in our company and you know every week we have partners meetings and I join occasionally so yeah I'm still very much in touch with the team and
Jeff is my colleague who joined only six months or a year after I did and then Rich is there now too so Jerry has a team around him and you know I'm part of that family I would say. Jerry's a very good a very family man and so I feel like I'm part of that family still. Maybe next time you could ask him hey do you remember yeah when you decided to hire me and I will one day I'm sure I will over a glass of wine.
Jerry loves wine he's a great wine guy maybe over a glass of wine one day I'll ask him that question then. How big was the team when started so the AME Cloud? Jerry bought his long-term admin and office manager and personal assistant you could say from Yahoo with him. His name's Cathy and she's absolutely wonderful and she's still with him now sort of 18 or 20 years later and that was the team when I arrived so it was Cathy and Jerry and I was the first investment sort of team member yeah so it was just the two of us again really great privilege
and really fun yeah. I see yeah really interesting yeah and yeah I also want to know the answer from Jerry so why yeah why this decided to yeah I'm sure you have been talking to me for 20 minutes you can't figure it out I can't figure it out either I think you're right there's there's some like I don't know what it is but um you know the the the fun thing about working with someone like Jerry is that you you you have a boss who's also a mentor in many ways and it's not because they
sit down and give you mentorship sessions every few weeks it's just because watching them work and watching them think and watching the way they make decisions and how they conduct themselves with other people and all that stuff is such an amazing way to learn and I really really appreciated that for the early years in particular working with Jerry it was it was really so great and obviously the access we had was was amazing and you know the idea for me and Jeff and others you
know and RETCH was to sort of carve out our own path as well not just rely on the network not just rely on the yahoo connections but to go out into the world and make a name for ourselves and so that became kind of the goal and I think you know most of us we all did that in our own way and we all did deals that you know but I remember the first deal I did where Jerry had never met the company I was uh or had even heard of them you know before and I thought that that was kind
of my first like oh that was that was cool that was that was one that I did that you know that kind of I bought in myself and obviously Jerry was a big part of our brand and but it was it was great to sort of start to make you know make our own hay that's uh it was always so great working with him for that mentorship reason I think and as an investor oh okay as an investor I'm curious about your like investment thesis at the time so that was I think 2012 and now
and you until you served like at 2020 and has your investment thesis changed over time or evolved over time yeah that's a great question yeah we should talk more about that so so I'm a cloud ventures I'm a AME means rain um uh in Japanese and so and Jerry's wife is Japanese so there's a Japanese connection there and there always has been for Jerry we were all about data we started as I said at the beginning of the Hadoop cycle and Jerry had seen how data-driven decisions and
data lakes and big data and even beginning to train models pre-AI really honestly pre-AI or pre pre-AI going mainstream I I'm not going to say that Hinton and other great thinkers were not working on some of the paradigms that we now use in all of our models in AI but the paradigm in sort of mature tech was was was statistics and data lakes and some simple models and some machine learning was beginning to happen too right and that was our thesis if you've got data uh you know
create value from it if you don't have data make sure you have it so our our whole thesis was like finding companies that were data-driven and were becoming data nexus in their space or industry or were you know working with data in some way and and the other differentiator that we we sort of double-clicked on was was uh defensible technology and deep tech so finding companies that had something that was IP first and uh defensible or deep first and finding technologists and dreamers
who were building something that was that was difficult and frontier tech you could call it so those are the two pillars of what we were investing in in the early days and I think largely that remains true for AME and I think they're still very data-driven obviously we had this huge shift in 2023 with with AI right 2022-23 with AI so that that has kind of brought a whole new raft of opportunities it's kind of cheap to say that we were in AI before it was cool but it's
kind of true I would say it's different it's a very different kind of AI now but we were I mean we were investing in robotics and AI and machine learning companies way before it was cool for sure there were only a handful of other VCs interested in this stuff you know data collective um you know obviously there were a few other VCs that were doing things but we were we were getting our hands dirty it was sometimes really crazy and and you know far out research projects but uh that was
that was what we did so we did companies that were doing new new kinds of food tech we did a lot of robotics we did companies that were doing data-driven biology synthetic biology um as well as you know infrastructure and sass and things like that so and we're very people-driven too so another big thing I would say if there were three pillars it was kind of frontier tech data-driven companies and then kind of people and so if we found someone we liked we would want to pull the
trigger on them unless they were doing something maybe in advertising or consumer that we didn't like um as much so it was really very people-driven um and so you know Eric has who came into the office in 2012 for the first time was was very much a team a team that's a person that's as well as sass obviously but um yeah and regarding team and meaning like your point is like in and including early employees maybe, but what trait or character or personality do you look for
or did you look for at the time for founders or is that yeah Stanford grad and yeah for sure yeah they must be smart but besides those. You're talking about potential investees right so uh potential founders yeah yeah potentially yes yeah I think it's a little bit like dating you know you shouldn't necessarily have like a list of things that you're looking for in a partner because then you might find one thing that doesn't match and then you say no or you might find that
everything matches quite well and you say yes I think there's a lot more to it than that uh we everyone has to carve their own path when it comes to being an investor and making decisions some firms have particular processes obviously but ultimately it's up to the individual who decides that they're going to talk about this company at partners meeting or maybe even bring their company in and and what causes a partner to do that so for I think it's different for everyone
right so the and in Adami we had the process of um if one of us really liked something unless there was a veto um from from Jerry effectively we could do it so it was actually very partner driven we were quite autonomous which is really great and that was very empowering my process was um and I think it evolved uh but I would sit across the table from someone and what you're trying to do is decide is this someone who I would work for uh is this someone I would buy from
and is this someone who I think that the best investors I know in the valley would back as well right and I think like and most importantly is probably the first one right would I work for this person you know the the best people aren't just smart they're charismatic they are uh well rounded they're authentic and they are um colored in different ways they have all kinds of different you know stories in their past that are that are to add to their story themselves
and so as someone's conversation unfolds and it usually doesn't take that long there's kind of like a a moment where you're like wow this is this this person is quite impressive and impressive basically means I would I would potentially work for them uh I think they can convince customers to buy from them and I think investors are going to want to back this person going forward and then you look at all the other things right you look at the technology and you look but often you know
I think we're also a lot of investors are doing what I'm doing and then they're filling in the gaps with all these other things that they that they need to get across the line uh ultimately so much of it is about people and I think you can get you know you could say that what if it's a good person a bad idea well honestly like that doesn't happen very often because good people don't generally work with bad ideas so it tends to be that if you like the person sitting across from
you you can start to get to the next stage and I think that was the main hurdle you know that was the main sort of gate gate I guess when I was a VC but everyone has a different way of thinking about it um you know like I'm a product and a technology person right so it was also easy for me to sort of start to say well ask more difficult questions or ask even just slightly probing questions about how things worked and if I felt like I was thinking of things that they were not thinking of then that
was not a good thing right I wanted to be um they need to be ahead of me thinking about things and finally the way people communicate is very interesting too so so what I found is that the smartest people and the best communicators they would understand very quickly where I was at when I was listening to them and then they would move the conversation faster forward you know much faster and they would skip things and they would they would bring things to my level and try and
push me even harder right and I really enjoyed that and I think that's the mark of a really of a smart person who's a good communicator you'd be surprised how many people who might seem like good founders but they will just go through the pitch exactly as the pitch is rather than adapt their conversation style or the communication content to the person they're sitting across the room from and I just think that that's weak you know so there was another small signal but it's all about people
I think in that sense so yeah how was the you know founder of zoom so Eric so how how do you see him yeah Eric was introduced to Jerry by I think Dan or Bill Tye, Dan Scheinman or Bill Tye thank you guys if you ever watch this I mean we've said thank you many times but had many dinners together Eric came into the office and was nervous and he was excited to meet Jerry you know Eric is Eric is very confident person he has a very he I think Eric is one of these people
who from a relatively young age probably mid-30s really began to truly understand the way the world works and the way that engineering teams work and the way the business works in many ways Eric should have been made head of Webex when he was there and that might have actually stopped him going and making him creating zoom Eric was already a leader within Webex right he was basically the first engineer and he built the engineering team within Webex in China mostly but he didn't just
build the engineering team he understood the way the world works so he when he came to us it was very obvious there was a confidence there that was going beyond just oh I'm a geek building a better product out of Webex he understood the nuances of go to market and how to sell and how to you know drive enterprise customer growth and actually he hired the first sales guy he hired was great and Greg eventually left after the IPO but built the company up from zero to 100 million
ARR and and so we got a sense of someone who is very well-rounded and who is kind of wise for his age and I think on top of that the product just worked you know one of the contentious points internally for us with zoom was at the time there was blue jeans and personally I believed that the future of video conferencing would be web-based and on would be on the browser and not in a standalone application actually and Kay you asked earlier about this I mean you know zoom did very
well with a standalone application you know you can get so much more done you have more access to underlying processes and services on the on the pc or the mac that you just don't get in the browser you can control the experience a lot better and I think that's an insight that Eric had in his wisdom when he started zoom that we didn't initially agree with because we didn't know it as well but I think we became confident with it as we used it Jerry we had a partner's meeting
um which uh shortly after we met Eric where we uh tried zoom while Jerry was in his plane um so Jerry was in his plane on you know weak satellite internet and it still worked and that class was a big sort of you know tick in the box of like wow this is robust right they figured out a lot of network robustness here this is quite impressive um but I remember at the end of that meeting that first meeting with with with Jerry and I uh Eric
was he would probably hate me for saying this but he had like a very sweaty like underarm because he was very he was very nervous to meet Jerry he was Jerry was like his idol right and I I think it's it's so it's so nice when you have someone who you look up to but ultimately definitely certainly for me and maybe for Jerry too kind of flipped or at least you kind of people rise up to their to meet their heroes and then they often will rise further in other ways and I think that's
really wonderful I think that's definitely what Eric did I still can't believe honestly I was part of that journey to see Eric kind of pitching to Jerry almost like a like his like sort of I don't know like a junior like his junior and then to become the very successful business person Eric's become and watch that in 10 years is just a wonderful wonderful journey to spectate right interesting in that sense I was curiously since you regret I mean I mean let's say in case of Zoom
I mean you invest in so many companies and you went through so many company and invest decide you know which company you invest in but let's say in case of Zoom I don't know how many x you know 100 x or or thousand x I think you invested in but if you let's say if you invested in 1 million but if you invested in 10 million the return was you know 10 x or more right so in that sense do you have any regrets that oh we should have invested more now of course everyone says that
of course everyone should always invest more in the winner are you the the you sometimes you should look at that kind of situation and say rather than say we should have invested more which we should have you should say how do we pick another one of those I think sometimes in venture people look at the lost upside or the downside too much what they should do is look at the gained upside and then double down on that and figure out how to do more of that
so so I think regrets they serve a purpose in some ways because they teach us stories and and you know ultimately we probably should have invested more in Zoom but the fact is how do you find the next Zoom and the next Zoom I don't think you know you're really good adventure until you can do it like two or three times in a row but I think you know you're really good adventure until you can do it like two or three times in a row and so you know that that is the learning
the learning is Zoom worked why how do we find more like that and you know that's and be thankful really be very grateful for that that we didn't pass right that that would have been the problem that would have been a real regret so you know however many dollars in versus dollars out you get the point the point is Zoom was a massive winner for everyone involved and and I think the point of venture should be to find as many of those as you can and not to worry too much
about everything else in essence any investment you missed but you should have invested I don't know maybe tons there's so many oh my god so so yesterday there's so many there's so many you know and sometimes we laugh at each other internally because I'm like oh you know I you know I wanted to invest in this and we didn't and and you know the fact is that there's lots of things that I would have wanted to invest in that wouldn't have worked out and there's things that
they wanted to invest in that you know I said no to whatever I didn't like so we all make mistakes and they're kind of group mistakes but you know that so yesterday Matilde will not remember me, but maybe she will. But yesterday, I signed up for Front, which is a service which provides unified inbox for various platforms. And it was funny. It was the first time I'd ever signed up for Front, because obviously, as a company, in AME, I didn't need to do it.
But for Quill, where you're now using Front, and I just remembered that that was one that we missed. I saw Matilde when it was a $12 million pre. And I remember meeting her at a coffee shop in San Carlos in Pete's. I remember exactly where we sat. And I won't go further as to why we didn't invest in that company. It was probably as much my fault as anyone else's. But that was one of the many misses. And there's so many.
You know, the good thing about misses is at least you saw them, right? If you're not seeing misses, then something's really wrong with your deal flow. So you should also take stock in the good things. You should look at the good things, right? Interesting. Do you think that a lot of investors or VC are learning from the missed opportunities? I mean, learning from success is much easier and easy to analyze. But at the same time, if you miss something really big,
and if you don't learn from your failures, and that's the problem, right? Yeah, I think there's a lot of problems at VC. Another problem is that it takes a very long time to learn. So it takes five or 10 years to learn because the cycle is very long. Yeah, I think you need to learn from your mistakes. I think you need to. I mean, I have quite a strong, I have a, maybe, and this might be slightly different to my team,
but I feel very strongly that you shouldn't worry about, that you shouldn't worry about the companies you invested in that went to zero. I think you should only worry about companies that do really, really well. And make sure you don't miss those. And so that is kind of my philosophy, is that it's really all about the winners. Because the winners cancel out everything else big time when they win big. And yeah, you should be looking at companies
that you saw that became big companies, and you passed on, and figure out why. Why did you pass? And was it a good pass? Or did you pass actually for the right reasons? And then maybe the market changed. And maybe you were right at the time, and then you just were unlucky, right? Or were you just wrong at the time? What was it exactly that made you pass? So much, guys, of VC is feeling. And I think if you feel really excited about something,
sometimes it's just right to do it. If you feel excited about something, but you don't quite know why, then you don't do it, and the company becomes big. Then the learning should be, next time I'm excited about something, I should do it. It doesn't even need to be some data-driven thing where they didn't tick the right box in a spreadsheet, or the right match with what you wanted, thesis didn't come out, right?
It should just be, I'm quite intuitive person, so I maybe over-index on this sometimes too, to a fault. But I really do think that gut feeling accounts for a lot. Yeah. Interesting. Just kind of switching topic, but you mentioned Jerry, the founder of Yahoo, was your mentor and boss, and you learned a lot of things from him. What is the best learning from him, or did you get any advice from him that you remember?
Yeah, what is the best learning from Jerry? Or repeated advice, always he's saying X, Y, Z, or something like that. Yeah, Jerry taught us a lot through osmosis, and then not so much implicitly. She's a very humble person, I like that a lot. I think some of the things are not so much about business, and just about how to be a good human. Jerry's very famous and rich, but is extremely humble and kind as well.
He doesn't seek attention in any way, doesn't want it. Really downplays it actually, would prefer to avoid attention, and I really respect that, and like that a lot. And also he's very kind to people who he's just met as well. He's very patient, and just a very good person. And I think seeing someone be very successful, and also a very good person, is a sort of nice reminder that wealth and fame don't always cause people
to become more difficult to work with, or sort of more negative experience with them. And that's always been an amazing thing. Other than that, Jerry was very empowering to us. He really gave us a lot of autonomy, which I really respected as well, and trusted us. I remember the first time I was in a meeting in a group with Jerry, and Zod, and Ash, Ash was the head of product, and Zod was a CTO, and they were investing on their own at the same time.
So we were meeting in partners meeting. And I remember at the very beginning of my time with Jerry, at some point they were talking about a company, and they all just turned to me and said, what do you think? And I was kind of blown away, because I come from China where things are much more top-down, and someone as young and inexperienced as me would not be asked what they thought. And I kind of paused, I had an opinion,
but I paused almost out of shock, because I was surprised to be asked, and have the room go silent to hear my response. So I think that kind of autonomy, and being given a lot of trust by Jerry, was also like a really big part of the journey for me, and really great. So I think if you find employees you like, you need to like basically fully trust them. That feels like a good learning as well. Now, Jerry's incredibly smart though.
So you just have to think faster when you're working with smart people, and be more prepared, and it forces you to be a better person and work harder too. He also works incredibly hard. You know, Jerry and Eric are the two people in my life who respond to emails faster than almost anyone else I know in my entire life. And I do not think that's a coincidence, that basically the two billionaires who I know best
are the two fastest email responders, right? Jerry prefers lowercase sometimes, which is funny, but yeah, they don't stop moving. And they keep their mind active, and they keep working. And I think that is a lesson for everyone. It's a tiny lesson, but very important, right? Is that him? Really him? Or is that AI? Different? Which one? That's definitely Jerry, yeah. Yeah. And did you write down those advices and learnings
on somewhere? And also, did you publish it somewhere? No, again, maybe I've taken this too much to heart, but with Jerry, again, this sort of don't try and get attention thing kind of sunk in quite heavily. So yeah, I haven't done a lot of writing about these things or anything like that. Feels like these days, everyone is trying to get attention and trying to participate in that for me is quite draining. So I don't do a lot of like blogging or stuff like that.
Maybe I should do more, but what do you think? Should I do more? Yeah, I want to learn from him, learn from you. So for smart people and good human beings. And in terms of increasing the number of people who have good mind, so we need to tell their story, right? So, but you know, if knowledge is isolated, so we cannot access it. That's true. Yeah, that's true. I think the best learnings though, maybe the most important education
is to teach people how to learn because ultimately the most important lessons don't get taught, they get learned by experience. So maybe the most important thing is to say, well, you know, to figure out these things, you have to go and fail and succeed and try it yourself. And then you kind of, those are when you really learn something important, I think. And it's impressive that you back to founder, to become founder and doing something
and trying something new and that's amazing. And, oh, then I wanted to ask this question. So since, you know, nowadays, thanks to AI, so there is a word, you know, VIVE coding and also VIVE revenue, meaning using AI tools. It's VIVE coding, VIVE revenue. And then it's for AI, that startups or company using AI, it's kind of easier to make money at the beginning. So in that sense, some people say, oh, you don't need, you shouldn't,
you know, as a startup founder, you shouldn't raise much money. And because you can make revenue using AI and also AI, like using Casa, Windsurf, you can save your time. I mean, improve your productivity so that you don't need to hire a bunch of software engineers at this moment. And what's your thoughts on fundraising for startup? Because you have experience on both, right? As an investor side and a founder side.
And would you recommend raising a bunch of money or try to keep the team small and raise less money and make revenue? Personally, I like small teams quite a bit. It's more fun. There's less politics. It's more efficient. I think there's some things you just can't do with a really small team. Enterprise go-to-market is gonna remain one of those for a while, for sure. So I think the question is dependent on the entrepreneur.
Some entrepreneurs may be deciding that this is something they want to do. They want a path where they want to have a big team and raise a lot of money. Sometimes though, if you raise money and you grow the team ahead of the product market fit, it can be challenging. I've seen that a lot. Sometimes large capital raises can kill companies as well. So you've got to be a bit careful. We definitely live in a different world.
I don't think you can prompt. company into existence, even though you can do a lot of stuff with cursor and AI now, you still need to be able to call, basically call the AI out when it's wrong. And so you need to have some skills there. I think we are getting more efficient, for sure. So you won't need as many people on the technical team as before.
And there is an advantage to have a smaller technical team. I definitely think that's true. It's exciting. I don't know where it goes. Fundraising-wise, a lot of it seems to go into marketing now. It feels like companies raised big rounds simply so they have a press release to say they raised a big round. Maybe there'll be a bank that gives a loan that isn't actually real dilutive capital, but it looks like a round, and now Forbes will take you seriously. I don't know.
It feels like there's a lot of things going on right now with the attention economy, where it is a lot about how much attention you get to your company. One thing that I noticed with the AI wave is that, unlike cloud and mobile, the AI wave doesn't come with a built-in distribution channel. So you don't get an advantage for starting an AI company today that you used to get when you started a mobile or a cloud company or a SaaS company, because nothing's changed with the distribution.
So that means people are just shouting louder and louder and trying to vie for our attention. So the question is really, in this attention economy, how are you going to get attention? That, to me, feels like a bigger problem really than the technology in some ways, and sometimes raising a round can help solve that problem. So I think the power dynamic has shifted. The reasons for raising capital have shifted.
The amount that needs to be raised has definitely shifted. For example, if you've figured out distribution, you probably don't need to raise money anymore to scale. Yeah, that's true. And I don't know what big VCs do with their big doshes of cash, honestly. Maybe they'll just pump money into companies later in a later stage and wind up having companies never go public, which is also dangerous. So it's a very interesting time right now.
And if I were in VC, I would probably be trying to figure out where to go where people are not going. Maybe I'd be investing in things that are not AI, because I think some of the companies that are not AI are having more trouble raising rounds. But there might be some really great companies in there. So it's an interesting time, but I think it really depends on the situation. But do you have a goal in your mind for, let's say, for queer meetings? Is there a goal like IPO, M&A, or you want to keep independent as a company?
It's fun to run an independent company that's growing and making money. It's kind of the way it used to work. Let's see. I don't know what's on the cards for us. I think we're quite happy with the state of the company right now. And we are building every day, and that's fun. It's super nice to wake up every day and see what you did the day before and to see customers who are using your product every day. I think it feels so good.
So to me, that's what I love doing. And I've never done it before at this scale. So it's just super fun. And where it all goes, I don't know. But we're not going to run out of money, so we don't need to fundraise, which is great. And we'll see whether we decide to raise another round. We're getting to pull into enterprise quite a bit now, so that might be a new path for the company as well. But it's nice to keep options open.
I think that's what founders can do these days, is just have a lot more options. So it's great. Amazing. And by the way, this is a broad question, but nowadays, AI is crazy, and people are using so many AI tools. Do you have any thoughts on recent AI snapshot, like work, job, skills needed in this era? Or you mentioned a mini-manager in early AI. Yeah, exactly. Yeah, I do. Yeah, it's interesting, right? The current generation of AI, it's kind of like a junior employee.
So sometimes it gets things right, and sometimes it doesn't quite understand and gets things wrong. So because it's a junior employee, the skills that are needed these days, I think, are managerial and experiential. It means that people of my generation are actually at an advantage, because we can make judgment calls and we have experience. Junior employees are definitely, real junior employees are at more of a disadvantage, because they won't necessarily have the skills that fill the gap between the AI and what's needed
for the company. So I think gaining that experience, I think if you're young, is going to be important, whether you start your own thing or whether you work for a company that's using AI. But becoming a sort of mini-manager of lots of agents and figuring out how to call them out and make the right judgment calls, that's really going to be the big skill of the future, I think, because I don't think AI is going to take all of our jobs at all.
It'll just make us more productive, and the people that will make most productive are the people who know how to use it the best, and the people who know how to use it the best are the people who have the most experience with whatever the AI cannot do, and being able to guide it. So that, I think, is sort of shifting the workplace quite a bit right now, and Mike and I and our few employees can just do so much with AI now. It's kind of amazing.
Do you use any AI tools in your daily work or your personal life? Yeah, I use Quill, obviously, and I also use Cursor a lot. I like Cursor. I haven't tried Windsurf a lot. I know that they're similar, but Cursor has been really, really great, especially in the last six months. It's really come a long way. So yeah, got a lot done with that. I love the agentic feature within Cursor. What other AI tools do I use a lot? Not a lot of others, actually. Day-to-day? No, no.
Coding and productivity, meeting productivity, are the two ones that I use a lot. Oh, and I do use ChatGBT, too. ChatGBT, for me, is like Google now. So yeah, I don't know if you guys feel the same, but feels like that's, it's kind of going to replace Google as a place you go to answer any question and get results. So we'll see where all that goes. I think OpenAI is talking about advertising as a business model, so that means they're definitely going after, or they're beginning to feel the crunch of, you know, they
have enough users, and so what you have to do eventually is you have to start to think about advertising. So we'll see. Yeah, I use pretty much the same AI tools, ChatGBT, Anthropic Cloud, and I prefer WinSurf, but yeah, I know both, but I use both, but yes. Yeah, yeah. What do you prefer about WinSurf? Why? What do you prefer? It's kind of UI, UX, it's a slight difference, I think. Hard to tell, but yeah.
And also some of my friends like WinSurf and use WinSurf, so I can ask some questions to them, so I think that's the reason, I guess. Yeah. Yeah, nice. Yeah, I mean, we're in a whole new era, right? Companies are growing very, very fast, some of these companies. The people I talk to seem to think that the steam might run out at some point, and they kind of reach a cap quite quickly. I'm not so sure. I feel like these are generational companies that are getting built in AI, so it's a very exciting time.
It's a really, really exciting time. You know where a company of 10 or 50 people can get to $100 million in ARR in two years. That's exciting. There's something new happening now, and it makes me feel a little bit, maybe a bit of FOMO for not being an investor, because it does feel like the dot-com times. It feels like 95, 96 right now. It's exciting. It's exciting. Yeah. Thank you. So, okay, two more questions, and one is advice, and do you have any advice to, let's say, younger self or aspiring
founders or engineers? Any advice at all? Any advice? Yeah. Yeah, I think just build. Just build. Build and sell. I do think that marketing is more important than I had realized, and I would say, you know, build and have an adventure, but also don't be naive to distribution. Yeah. Oh, I remember, like, there's a famous saying, like, first time founder, focus on product, and second time founder, focus on distribution, and yeah. Yeah. It's interesting.
So, okay, yeah, the last question. Since Glasp is a platform where people share what they're reading, learning, as their digital legacy, and we want to ask you this question, what legacy or impact do you want to leave behind for future generations? Yeah, I have very, very low bar, very low goals here. Nothing exciting. It was fun being an investor, and maybe I'll be an investor again in my future, but the joy you get from building products that people use, and they tell you they like,
and you can see they're using in the analytics, is like nothing I felt before, and I would love to just grow the company I'm building or a future company very large that I'm having a positive impact on hundreds of thousands or millions of people. This is a wonderful feeling and a great privilege, and to be able to influence people. and that also just to give them benefit through something you've built and designed
is such a privilege. So that's all I would like to be able to do, yeah. And that's the mark you leave. And ultimately, I think that people die, blah, blah, blah, but what you leave is everyone you touched and then they will have something in them, even if your product dies in 50 years or whatever, and then they've benefited from it. So I think the web of life means that you're always giving back something. And if you can give back to lots of people,
that's really a great privilege. That's all I want. Really beautiful, and I feel the same. And yeah, thank you. And thank you so much for joining today. Yeah. Of course. Thank you for having me. I appreciate it.
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From VC to Builder: Building the AI Tool Shaping the Future of Work | Nick Adams
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