How a VC and tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) & Nabeel Hyatt (Partner at Spark Capital)

4 Aug 2025 · 49 min · 20 chapters

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In short

Andrew Mason and Nabeel Hyatt describe how they used AI (especially Claude) to launch Tabletop Library, a Berkeley membership board-game social club with a physical space, curated game merchandising, and an AI concierge that organizes on-demand game sessions via SMS.

Guest backgrounds

Andrew Mason is CEO of Descript, an AI video startup (video editing agent mentioned). Nabeel Hyatt is a partner at Spark Capital, which invested in Descript; he and Andrew live near each other and both became board-game enthusiasts.

Key claims

The business “wouldn’t have existed without AI,” used as (1) co-pilot for business planning, (2) manual-worker for heavy grunt work (categorizing games into a Dewey-like system), and (3) builder of new experiences (AI concierge). AI improved speed and confidence for planning, permits, and operations; LLMs were weak at spatial floor plans but strong at personas and business frameworks.

Notable examples

Dewey Decimal-style TLCS codes (e.g., cooperative category “400” and complexity weight); Airtable + N8N + Twilio SMS workflow; AI concierge forms a quorum before revealing players and booking tables.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Board Game Renaissance

0:00 to 1:33

Discover the growing interest in board games and the idea of a membership-based club.

“There's this kind of renaissance going on with board games that I've just gotten clued into in the last couple of years.”

The Board Game Renaissance

1:59 to 2:44

Discover the growing interest in board games and the idea of a membership-based club.

“ever had an idea for an app but didn't know where to start, Lovable is for you.”

Turning Hobbies into Business

2:44 to 4:52

Andrew and Nabeel share their journey of transforming a board game hobby into a retail business.

“Nabil and Andrew, thank you for being here.”

The AI Advantage in Business

4:52 to 6:05

Explore how AI played a crucial role in launching their board game cafe.

“So you could just be like, I want to show up and play this kind of a game on Friday.”

Using AI as a Business Partner

6:05 to 8:12

Discover how Andrew and Nabeel used AI to assist in various aspects of their new venture.

“So let's get into what, because this is a very in-person, service-oriented, human, physical business that you're building.”

Challenges and Solutions

8:12 to 12:16

Learn about the challenges they faced in starting the business and how AI helped to solve them.

“The first one is sensibly AI as a co-pilot business partner.”

Persona Development and Market Analysis

12:16 to 14:00

Understand how they developed customer personas and conducted market analysis with AI.

“Just this is where everything goes and you have, I don't know, 100 plus chats in here.”

Using AI for Persona Identification in Gaming

14:00 to 24:12

Learn how AI is applied to identify user personas for a board game business.

“research on and so it's inside of its context window.”

Building an AI Concierge for Tabletop Library

25:19 to 28:02

Explore the development of an AI concierge to enhance game session organization.

“I just can't get out of a How I AI podcast without somebody talking about Vibe Coding.”

Exploring the Database Setup

28:02 to 30:03

Learn about the structure and components of the database created for organizing games.

“It seems like a no-brainer, but it wasn't obvious to us at the time.”
Show all 20 chapters

Why Choose Airtable?

30:04 to 32:03

Discover the reasons for selecting Airtable over traditional database solutions.

“So what do you think should have been in the consideration set before I answer that?”

Utilizing AI for Game Categorization

32:04 to 33:56

Understand how AI is used to categorize games effectively within the system.

“I mean, a ridiculous amount of these cells, to be clear, came from that cloud project we talked about earlier.”

Implementing a Library System for Games

33:57 to 36:09

Learn about creating a Dewey Decimal-like system for organizing board games.

“relevant that looks like records or games that might fit.”

Automating User Interaction with Text

36:10 to 40:10

Explore how user interactions are automated through text messaging and AI.

“And maybe for every – there's five of these.”

The Role of AI in Enhancing Experiences

40:11 to 42:01

Understand how AI enables experiences that would not be possible otherwise.

“contacting three members to see if they can play the game and when one of them says no you contact another it's like maybe you could do something like that but it for organizing a board game night.”

Technical Insights on AI Applications

42:01 to 43:28

Learn about the practical applications of AI in programming and project management.

“but I'm not seeing you pop open cursor in a repo.”

Favorite Games and Personal Insights

43:29 to 44:35

Discover the hosts' favorite games and their thoughts on gaming culture.

“then iterating and brainstorming from there.”

Getting AI to Listen: Tips and Tricks

44:36 to 46:11

Explore effective strategies for improving AI interaction and communication.

“And it's really fun to play with my wife or my kids.”

Connecting with the Guests: How to Reach Out

46:12 to 46:49

Find out how to connect with guest experts and their current projects.

“I can't wait to bring my kids over and see what other cooler games we should get into.”

Connecting with the Guests: How to Reach Out

46:54 to 47:42

Find out how to connect with guest experts and their current projects.

“But also I have to say, yeah, I'm the CEO of Descript.”
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Transcript

Automatic transcript. May contain errors.

0:00Andrew Mason:There's this kind of renaissance going on with board games that I've just gotten clued into in the last couple of years. Both of us had independently thought, wouldn't it be cool if there was like a membership-based social club, like a physical space that you could go to and just show up and play board games, either bringing your own friends like you might do at a board game cafe if you've ever seen one of those, but also you could play with other members.

0:23Nabeel Hyatt:If you're starting your board game navigation, and maybe if you've ever been inside of a board game cafe, you've had this feeling. You walk in and you've maybe played Catan and maybe your friends had you play Wingspan and now there's just like a wall of games and you have absolutely no idea where to start. Well, this has been solved. In libraries, you have a card catalog library system where all of the French history books are next to each other and so on and so forth. This is the kind of thing that would be like literally impossible without AI, but we basically have a bunch of design prompts in Claude back in those projects that help to categorize into kind of a Dewey Decimal system of board games.

0:56Andrew Mason:I've seen how AI can help you code at an extremely proficient level. You can PM, but you are showing me how you can take your slightly nerdy, little bit niche hobby to an extreme level and even turn it into a business. It's truly the most ridiculous idea. If he had proposed this and we didn't have AI, I would have gone to the mat like this is such a crazy thing that nobody's going to want and it's going to be such a waste of time. But because we do, we can indulge in this kind of stuff and it's really fun. And maybe for every five of these, one of them will be the best thing ever.

1:32Andrew Mason:Welcome back to How I AI. I'm Claire Vo, product leader and AI obsessive here on a mission to help you build better with these new tools. Today, I have Andrew Mason, CEO of Descript and Nabeel Hyatt, VC at Spark Capital. Sure, they're a founder and a VC by day, but by night they used AI to take their hobby and turn it into an in-person business. Let's get to it. This episode is brought to you by Lovable. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to a live domain.

2:12Andrew Mason:It's perfect for marketers spinning up tools, product managers prototyping new ideas or founders launching their next business. Unlike no-code tools, Lovable isn't about static pages. It builds full apps with real functionality and it's fast. What used to take weeks, months, or even years, you can now do over the weekend. So if you've been sitting on an idea, now's the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev. Nabil and Andrew, thank you for being here. What I love about what we're going to talk about is I've seen how AI can help you code at an extremely proficient level.

2:56Andrew Mason:You can PM like 10 PMs, but you are showing me how you can take your slightly nerdy, little bit niche hobby to an extreme level and even turn it into a business. So, Andrew, can you tell us a little bit about what you built with AI? Nabil and I, the way we got to know each other is I'm the founder of an AI video startup called Descript. Nabil is a partner at the venture firm Spark. He invested in Descript. And it turns out that we actually live a couple blocks from each other. And it turns out that both of us have gotten into board games over the last couple years. Do you know anything about board games?

3:39Andrew Mason:I have a six and eight year old and we're just entering board game era in our house. It's a long road ahead. Yeah. Yeah. But when you say that, do you mean like Monopoly and stuff like that? We run the gamut. We do. We just got Scrabble because we're spelling now. So that's good. We got like the Dungeons and Dungeon Mayhem. You know, we're playing like a lot of Dungeon Mayhem. So we're stepping into like the D &D world. And then, no, we have not gotten into these complex board games. Although my friends are trying to get me into this like bird call game, like this birding board game. Wingspan, probably.

4:11Andrew Mason:It's definitely Wingspan. There's a small cohort of parents in Birdal Heights into Wingspan. Yeah, so that's a good example. There's this kind of like renaissance going on with board games that I've just gotten clued into in the last couple of years. I kind of always wrote it off as this incredibly nerdy thing, as you put it. But it's actually a really fun social way to come together or excuse to get off your screens and do something. And Nabil and I started getting together to have like game nights and play together and just found it like hard to pull off with everything that was going on. and one day we were sitting around just like talking about this and it turned out that both of us had independently thought wouldn't it be cool if there was like a membership-based social club like a physical space that you could go to and just show up and and play board games either bringing your own friends uh like you might do at a board game cafe if you've ever seen one of those but also it could you could play with other members and you could offer a kind of service to help people organize games with other members.

5:22Andrew Mason:So you could just be like, I want to show up and play this kind of a game on Friday. Can you see if other members are interested in doing it? So we were like, oh, this would be so cool. And the next time a retail space opens up in the little shopping area in between us in Berkeley, we're going to have to rent it, even though it's totally irresponsible and neither of us have any time for something like this. And sure enough, that's what happened. And so we rented this space when, Nibiel?

5:51Nabeel Hyatt:This was probably four months ago, five months ago, something like that. Yeah. And we've been on a crazy adventure trying to figure out how to be small business owners on top of two well over full-time jobs that we're also managing and families and the rest of that stuff.

6:04Andrew Mason:See, I don't think the listeners or the watchers were prepared for this episode to be What I Built With AI, retail location, physical board gaming cafe. A cafe. So let's get into what, because this is a very in-person, service-oriented, human, physical business that you're building. Very different, Andrew, than I think your business, your AI business that you run now. How did you use AI in the mix of standing up this new opportunity?

6:35Nabeel Hyatt:I think the first thing and the reason I think we feel good talking about it here is that there's just no way this business would have existed without AI. at about 100 different levels, which will become very obvious very quickly. So first of all is just neither of us are small business owners. Neither of us have ever run retail locations. This is like one of the millions of things that millions of people just like randomly say over dinner or talking amongst their spouses or whatever. We're just like, wouldn't it be great if? And AI, and in particular in this case, Claude, is very good at being like, that would be great.

7:11Nabeel Hyatt:Sure, you can do that. And then, you know, this is ostensibly an exercise of like, you know, pulling a thread until the like duvet covers all over that, you know, room and you end up with a retail location. And so the first bit is just we use Claude to ask simple questions like, I want to open up a place to play board games with my friends in Berkeley. These are my goals. And instead of being prescriptive, you're trying to just say what you want. And then it giving us lots of information. So this is a couple of weeks into the project. This is now months ago. An example of just it's giving us how to lay out the space properly, what the budget should be, you know, how to think about pricing, financial projections, the like myriad of 15 ,000 different things that you'll need to do in order to get this thing open.

7:57Andrew Mason:And you said this very simply. You just said sort of what's the business plan for this or was this a complex prompt? Like how did you get to this level of detail on your business plan?

8:06Nabeel Hyatt:I'd say there were three things that we at core used AI for throughout this project. The first one is sensibly AI as a co-pilot business partner. It's making the business plan. The second one was AI as kind of like a manual worker, which we'll get to, which is just an unbelievable amount of just like grunt work in getting this open, not least of which is something like trying to categorize hundreds of board games through a unique Dewey Decimal system we invented and then trying to individually label them, which we'll get to in a minute. And then lastly is trying to use AI to make new kinds of experiences.

8:41Nabeel Hyatt:We built this AI concierge service where you can actually just like text a number and say, I feel like playing a certain type of game with these kinds of people on a Friday afternoon. Can you find them and figure it out? And all those coordination problems that end up being kind of impossible to articulate until you have an AI kind of making sense of them back end. So in this first phase, yeah, we don't know what we're doing. So a lot of the process, I'd say, was a cycle of more simple prompts. These are not massive PRDs. We don't even know what it is we want yet. So I would say the cycle was much more like we make a document.

9:16Nabeel Hyatt:And if I had to kind of externalize it now, I'd say the pattern was instead of it being a chat, we're talking to the AI, it talks back to you and you talk back. A lot of it was document generation. And then that document generation would become context for the next set of conversations. And so you're slowly working through like a little bit of a mission statement and a little bit of a business plan and so on and so forth. And then you slowly move that back in. And so each time you're talking back into a Claude project or whatever we happen to be using, it's gaining context more and more and more as you are moving through the project.

9:47Andrew Mason:Can we look at that business plan again? Because I want to go through a couple of the specific use cases. And what I think is interesting about them is you both are busy people. And so I can imagine all of these problems, your big brains, they're all solvable problems in some sense, or some of them are solvable problems. But I bet the speed at which you could solve them was kind of like tremendously helpful to you in your time-constrained world. And so I'd love to talk through like a couple. I think there's some like space layout use cases. Maybe we can start with that just as an example.

10:20Nabeel Hyatt:Well, the thing that won't come through here because this is a single document is if I were to back up into Claude. So this is just literally one document, maybe a month in. If I back up into Claude now, like what you'll see is this is part of a project that has gotten to a somewhat insane level of types of questions. So you mentioned one thing, which is how do we think about the space? But, you know, if I just scroll loosely through here, you can start to get a sense at the number of different things that come up in just trying to open up a small business. For instance, we were reclaiming redwood from a forest.

10:59Nabeel Hyatt:How much redwood should we need? We were trying to write a letter of intent to a landlord. I have no idea. I have never written a letter of intent to a landlord to lease a space. How do we do that? Right. I could keep going through these, but inside of here are things like timelines and to-do lists, Berkeley permitting. That's a fun thing to try and figure out. Right. A draft of a PowerPoint deck that we wanted to send to the landlord to look like we're a legit business. Again, something we could have done. We've obviously both built a lot of PowerPoint decks in our life. But this was for a landlord.

11:31Nabeel Hyatt:Like I can pitch for a VC or a founder or like, you know, or trying to get a project done. I don't know what a landlord wants to see in Berkeley. Anyway, so a lot of it was this. And then the important thing, of course, is that as these contexts, these docs are building up, we're just dropping them in. And you can start to see over here on the right-hand side things like this is the Board Game Cafe overview I showed you a second ago, a competitive analysis of what the market looks like, pricing, figuring out pricing. And then we started to get into things like player personas. So like, okay, what kind of people are going to come to this place?

12:08Nabeel Hyatt:And that, of course, leads into revenue calculations and all the rest of that stuff, which I can show you in a second.

12:14Andrew Mason:Yeah, so it looks like your general workflow was use Cloud Projects, set up a project for the entire business. Just this is where everything goes and you have, I don't know, 100 plus chats in here. And then those chats were creating these documents and these sort of artifacts. And then you were loading those artifacts into the project as context for future chats. And it seems like you're solving a variety of problems. One is like real estate in Berkeley, SOS. then it's you know just calculations whether those are physical area calculations financial calculations and then communications presentations content sort of sort of generation i wonder if you would show us one of the chats and again i'm like really attracted to this um floor plan one because you and you know you andrew and i should pick a different one because it was bad you know it was

13:06Nabeel Hyatt:really bad at floor plan.

13:07Andrew Mason:I mean, well, maybe we want to see how bad it was at floor plan. That could be helpful. Or was there something that it was good at that, you know, you felt like would have taken you a really long time to figure out as a novice in this kind of business?

13:20Nabeel Hyatt:Yeah, you're right. You're right, Andrew. The floor plans, it's good to talk about what's good and bad. So as we tested Claude and in general, lots of models, which we bounced back and forth between here and Windsurf and Cursor and every single AI product we could possibly use to make this thing, I would say you start to get good at finding the edges of it. So obviously, LLMs have no spatial memory. So a lot of the floor pan things it did were pretty poor. But a lot of the persona work, what kind of people would come to a place like this? How often would they come? It was really good at. A lot of business plan things it was very good at.

13:56Nabeel Hyatt:Ostensibly, the kinds of things you can imagine people have written about on the internet and it can do research on and so it's inside of its context window. So this is an example of a persona identification system that we worked on with Claude over the course of a couple of weeks. And to explain it very quickly, like this is the top access X to Y is basically how gregarious you are about games. Are you devoted to playing only one game? I just want to play chess every single day. And on the far right is like, I want to try games all of the time. I want the new game every week and so on and so forth.

14:30Nabeel Hyatt:And then down the Y axis is ostensibly how introverted versus extroverted you are. Right. So the top, the top right is somebody who literally just wants to play chess with their friends. Like, I don't want to play any other games. I don't want to do anything else. And in the bottom left is somebody who is, wants to really use this to meet new people. And so we ended up with this kind of, you know, three by three matrix of all the different types of personas. And then Claude did a really good job of kind of dividing up and then saying, well, in general, what percentage of those people come to a business, like come to a business like this?

15:06Nabeel Hyatt:And then importantly, what kind of events would you build that would handle the myriad of people that are going there? Because part of our experience when we go to board game shops or card shops is that we kind of feel like they're mostly tuned for a very specific kind of individual, which is like they're going to have if you like playing chess or you like playing Magic the Gathering then you come to Magic the Gathering night and you play with other Magic the Gathering people and it's very and that's I've done that I've played Pokemon with my kids for years like it's wonderful but it wasn't the kind of full penelope of people we felt were now playing board games in this world where it started to become much more mainstream and much more of like a broad social activity and so we're trying to cover for that.

15:47Andrew Mason:So the other thing that I see here, which I think is there's two things that I see are really useful. One is just coming up with a way to categorize your users or your customers by some axie on which you can prioritize some part of your product and your product is these events or ways to attract people in. You know, the other thing that I think is really interesting is if I were to come to a business like this that I was unfamiliar with having lived in the warm waters of enterprise software, I would say like, I know you need a building and I know I'm going to put games in it, but how do I turn this into a business?

16:19Andrew Mason:And what I see here is it's giving you frameworks for, well, you're going to need events and you're going to need private parties or you need open hours, you need closed hours. And how much did you brainstorm the actual business model and shape of the business using AI? Or did you all have a pretty strong point of view of how it would look? Even before we signed the lease, we used AI quite a bit to figure out if this was even a business that could be made viable. Like, I don't know if you can tell, we're not trying to turn this into a multi-billion dollar unicorn. But we are hoping that it's just not a money pit.

17:00Andrew Mason:And we didn't know where to start in answering those questions. So I think what was useful about the floor planning exercise that we did was like, how many people can we fit in here? And I would say that the way that this has gone for us, it's less that there's like particular, like specific tactics or tips or tricks. It's more of like having developed this mindset. But I remember when Amazon was transitioning from being a bookseller to an everything store. And you could buy paper towels on Amazon. And for years after they started selling paper towels on Amazon, I would still go to Costco to get my paper towels.

17:40Andrew Mason:So it's like I thought that was really cool, but I hadn't rewired my brain yet. And I think that's where a lot of us are with AI, where we're like, this is cool. I'm a convert, but I'm not rewired. And there's something that needs to happen where you remember that AI exists as you are contemplating a problem in front of you and you remember to engage it. And that's actually like the biggest thing. And as soon as you get there, a lot of this just takes care of itself. Like right now, we're getting ready to do a vibe coding hackathon at Descript. and I've gotten pretty good at vibe coding the Descript app.

18:21Andrew Mason:And someone on my team was asking me, what are the tips and tricks? Can you record something where you share something? And I couldn't think of anything. It's not really that there's specific ways of whispering to the agents or whatever, as much as it is just remembering that this stuff exists and having it in front of mind. Yeah, I agree with you. I think so much of AI adoption is about changing muscle memory, about where you go to solve problems. And it seems like from the beginning of establishing this business, you said the place that we go to build this business is this Claude project. So the tool number one I'm going to reach for is this AI partner that we have.

19:04Andrew Mason:And I think that pays off dividends as you put more and more. It's going to be really interesting in two years or three years when you have all this context of not only the beginning of the business, but how it's performed over time, what challenges you've had, you know, that's the institutional memory of your business that can only make it better, I think, as a partner moving forward.

19:26Nabeel Hyatt:Yeah, I think a lot of the early part of this project was really just getting in the habit of almost like reminding each other as we just ask some dumb question, like, have you asked Claude yet? Like, and it's, you know, we both live in AI every day in our day jobs. And yet you'd still find that you needed to get reminded. Like it was, it was amazing to me how quickly you had to, you know, I would go to look up information very obviously thinking about it as Google and saying like, oh, how, you know, what are some local board game shops? That's an easy thing that we have this Google kind of search mentality, but, but treating it as a, as a muse instead of as an Oracle was kind of the shift that you like, Like every time I'm going to go think about the thing, I should go drop into this area and use this as the partner to think about this thing.

20:14Nabeel Hyatt:That was the big shift.

20:15Andrew Mason:I'll just say I'm conscious as I hear Nabil and I talk about this that it might sound like we're just like outsourcing thought to this AI and generating like the retail equivalent of slop. But it really like couldn't be further from the case. We were just talking about this the other day, that it feels like that energy, that creative flow that you get in the best parts of creating something new. It's like you're just mainlining that because your feedback cycle is so fast. You can have this thing go out and do a bunch of grunt work, and then we're sitting around in kind of creative ideation, analyzing what it's come back with and building off of it.

21:01Andrew Mason:It's really fun. Speaking of grunt work, for folks that are watching that are not in the Bay Area, the thing that I think is most brave about this is you all went into Bay Area commercial real estate, which is a place that totally terrifies me. And I'm curious if you could just give us a few minutes on how you navigated this real estate transaction with confidence. And I would call it a complicated real estate market. And how you got to confidence you were getting the legal, the regulatory, the local advice that was accurate, you know, using some of these tools.

21:39Nabeel Hyatt:Well, let's keep in mind that there were still lawyers involved.

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21:42Andrew Mason:There are always still lawyers involved.

21:44Nabeel Hyatt:At some point, you know, there's real estate agents, there's lawyers. But what was really helpful, obviously, is you now hear all these anecdotes of people who, for instance, are still going to a doctor but are taking their health diagnosis and dropping it into LLMs to get a second opinion. I would say the cycle felt a lot like that. I think it was about building a level of confidence that felt like you could lean into the experience because you weren't going to get fleeced. and so we still relied on experts all the way through we still but but i would just sit at night and say like i don't even know we're trying to describe a concept for an experience of this membership club with retail in the front and we're going to do special events in the back and what is the permit for this in berkeley that won't take like two years for me to get done and uh and that's where you get a little bit of confidence as you're navigating through things Andrew would come back and he'd be looking through Berkeley weird like local ordinance websites and copying the pages and dropping them and clawed and getting feedback on them and things like that.

22:45Nabeel Hyatt:And so it really wasn't it wasn't, again, like like I was doing all the work. It was just that I in that instance, I would say I was giving us the confidence, whereas maybe five years ago would you've been like like you would have had the I would have had this fake expression you had, which is just like this seems scary. it seems Byzantine, like the inertia can't even get started. And so I'm just going to go do the other thing. And this will still just be a thing I complain about. And when I fast forward that, it's just the thing that makes me excited is not just that this exists. It's just like, literally, this wouldn't have existed without AI.

23:19Nabeel Hyatt:Two, as Andrew mentioned, there's so much grunt work in getting something like this open that, again, it couldn't have happened as a side gig. It just couldn't have. It would have had to have been a full-time job. And then there'll be this new, interesting, hopefully break-even place that people actually like in the local community. And if you fast forward that, like, obviously, we are in AI and we have some coding backgrounds and we're very highly technical. We're dropping into things like Cursor and Windsurf, which is not what the average local business person is doing today. But if you fast forward three or four years, you can imagine the multiplicative effect as these tools get broader and broader and broader.

23:55Andrew Mason:And for communities, that means you get interesting businesses and places to go and new people to meet and ways to connect that could not otherwise exist. So I'm very much an optimist that the more we can build, the more amazing things we're all going to get to experience. This episode is brought to you by Persona, the B2B identity platform helping product, fraud, and trust and safety teams protect what they're building in an AI-first world. In 2024, bot traffic officially surpassed human activity online. And with AI agents projected to drive nearly 90 % of all traffic by the end of the decade, it's clear that most of the internet won't be human for much longer.

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25:18Andrew Mason:You know, you mentioned Cursor. I just can't get out of a How I AI podcast without somebody talking about Vibe Coding. So Andrew, I'm going to kick it to you to talk about how you actually built an AI concierge for this gaming place. And what is it called? I forget. We didn't mention it. Tabletop Library. Tabletop Library. In Berkeley. Tabletop Library in Berkeley. We forgot to promote it at the top of the show. But how did you build this AI concierge so people could actually access this and have a great experience? Yeah. So one of the ideas that I was quite excited about with this was something that could help organize on-demand game sessions with other cool people that took away a lot of the social weirdness of setting these things up and the social risk in the way that nerds in Silicon Valley are prone to worry about.

26:22Andrew Mason:and so the the mechanism was going to be that you would have you would have this way of saying i want to play a game at some specific time see if you can find a group of people form a quorum and then if you can form that quorum you can reveal us to each other and we'll book it otherwise nothing actually happens and we started out by thinking at the very beginning like okay we'll just find a SaaS software package that gets as close to this as we possibly can. Let's look at table management stuff or other brick and mortar reservation systems. Then we started looking at co-working space management systems.

27:07Andrew Mason:So there was the just standard book a table, straightforward with your friends. And so the idea was that you would be able to use this software to either just book a table with your friends or try to do what we're calling a lfg looking for gamers mechanism where you could say like go out and find this group for me and then book a table and we were playing with all this sas software and it's like it often is where nothing's quite right like you want something so much more custom and then at some point we realized like all we're talking about building here is a relatively simple set of tables, a relatively simple database.

27:49Andrew Mason:And then you could just have like a chatbot living on top of that. Why don't we just build it that way? It wasn't, getting back to that mindset thing, it wasn't at all obvious to us when we started this. We spent a month going down this. In retrospect, I'll show it to you. It seems like a no-brainer, but it wasn't obvious to us at the time. So I'm going to give you a quick demo of what we built, and then I'm going to show you a little bit of how it works, because the one thing about it is we're still building it, and it's kind of slow. So let's say I want to organize a game this weekend, and I can go like, hey, can you set up a game for me any time this weekend?

28:30Andrew Mason:Maybe a deck-building game. So now that goes off to the agent. And I'll show you how we built all that now because it takes a second. And then we'll come back and see its actual reply. There's two parts to this system. One is the database itself, which we built in Airtable. And the other is this workflow from a company called N8N. And let me start by walking you through the basic things of the database. So there's a table where we have all of our users. What's really interesting here is things like availability. So it's going to eventually go and try to recruit other members. Normally in a database, you would store that as a bunch of related tables.

29:16Andrew Mason:But here you can just have free text. This is where you put your gaming preferences in. So it's just like a free text list of the games that the agent will update as stuff goes. So structuring these databases becomes so much simpler. Then we have like the tables that are available in the shop. We have games that we stock. And then we have actually the reservations once they get made. I would like to pause here and just call out you're using Airtable instead of another kind of, I'm sure there's lots of databases that you could have done on the back end if you wanted to. Could you just tell us why Airtable and why you chose to do something like this for this particular project?

30:03Andrew Mason:Yeah. So what do you think should have been in the consideration set before I answer that? Oh, I was just wondering. I mean, I would have just spun up a Postgres database. And if you had a cursor, I would have just gotten straight to just an empty database and a schema. And that's where my developer mind went. So I'm curious why you started with a tool like Airtable? I would not have gone there. I would have been more like, should we be using Notion or some other kind of something with a heavy GUI? Because the nice thing about something like this is we can also build human interfaces for interacting with this directly.

30:41Andrew Mason:So if we have somebody that wants to call up and book a table or something like that, we can build an interface for somebody to just go directly into it or manage events or something. So it just makes it much easier. And it means that people who are going to be, you don't have to be an engineer or build a front end for every command that you want to do.

31:01Nabeel Hyatt:It's a good prompting though, Claire, because this is, again, this was probably four months ago. It's very possible that four months from now, the right answer is you can one-shot a web interface to all of this. And then there's no, that it looks exactly the way you want it to look like. Like in this world, Airtable, one, I don't have that confidence in Windsurf, certainly not four months ago, as we're getting to Cloud4 and beyond, maybe so. And second of all, this just has all of the sorting mechanisms and filtering mechanisms and a million other things that come along with the human use of typing in 100 games or doing other work in those workflows.

31:34Nabeel Hyatt:It's just helpful.

31:34Andrew Mason:Well, and one call out for folks out there thinking about building something like this is in past lives, I would have thought, oh, my God, I don't want to work with the Airtable API. I don't want it. But so many of these things come pre-integrated now with these workflow builders. So much of what you use with these AI tools can figure out the integration points for you. So you can pick the thing that's easiest for you to use. And when you need to integrate it, I think it's very accessible. So it makes sense to me for a business like this. I was just curious if that was yours.

32:05Nabeel Hyatt:I mean, a ridiculous amount of these cells, to be clear, came from that cloud project we talked about earlier. and then were MCP connected into Airtable and it was just injecting data directly in.

32:15Andrew Mason:Can you talk about that flow really quickly? So you told us how you sort of set up these tables for how many physical tables you have, what games you have, who is interested in what kinds of games. How did you actually populate this data through MCP? I'm really curious about that. Yeah, let me give you an example of that one. So like this is, we have a small retail section in the front and we had this idea of like, what if instead of just putting things in alphabetical order or by like a traditional category, we merchandised and curated these categories. You can see some of them here, like brain burners, silent strategists.

32:53Nabeel Hyatt:Almost like the way your favorite independent bookstore merchandises their books in the front, right?

32:59Andrew Mason:Yeah. But there's this puzzle of how do you pick the games and how do you make them mutually exclusive so that you're not merchandising the same game in multiple categories. And that is the kind of thing that probably people have the idea for all the time when they're opening something, but it just ends up on the cutting room floor because of the amount of time it would take to do it. Or you do it at the beginning and then you're like, it's just not worth it. And you cut it and it just makes it trivially easier to do it. So it's like games about cats, for example, you can do something like that.

33:35Andrew Mason:You just give a brief description of what your category is, and then it'll go off and come up with the games automatically. So it's nice in Airtable that they have these built-in AI fields and stuff like that. Got it. So you're using built-in AI categorization by Airtable to create a category and pull in relevant that looks like records or games that might fit. Right. So that's the way that we use the existing tools. Nabil, what were some of the things that you populated with MCP? Is there a tab I should switch to here?

34:10Nabeel Hyatt:Well, probably the easiest one and the most wonderfully nerdy is if you hit games on that tab and then go click to in library. So one of the things we wanted to do, given this is called tabletop library, is to think about this place. If you're starting your board game navigation, and maybe if you've ever been inside of a board game cafe, you've had this feeling, you walk in and you've maybe played Catan and maybe your friends had you play Wingspan and now there's just like a wall of games and you have absolutely no idea where to start. Well, this has been solved. In libraries, you have a card catalog library system where all of the French history books are next to each other and so on and so forth.

34:46Nabeel Hyatt:And so this is the kind of thing that would be like literally impossible without AI, but we basically have a bunch of design prompts in Claude back in those projects that help to categorize into a kind of a Dewey Decimal system of board games, all of the games in existence and then looks at each game and applies them. So if you look at here, this is a list of games that are in there. And if you look at the bottom, you'll see the TLCS code, like 420.5 on this game, Nemesis Lockdown, right? And that means it is a category name in cooperative. That's the 400 section is cooperative. The 200, the 20 section, 420 is adventure co-op games in adventure.

35:24Nabeel Hyatt:and then the dot five is the weight of the game, one being the lightest weight and five being the heaviest weight as in complexity of the game. And so now you can imagine if you're interested in playing an adventure co-op game with your friends, you walk over to the 420 section and they're all nicely grouped together and then those colors, those yellows and reds are how hard that game is to play and so on and so forth. Impossible, literally impossible without AI.

35:50Andrew Mason:We are really taking people on an adventure here. It's truly the most ridiculous idea that if he had proposed this and we didn't have AI, I would have gone to the mat like this is such a crazy thing that nobody's going to want and it's going to be such a waste of time. But because we do, we can indulge in this kind of stuff and it's really fun. And maybe for every – there's five of these. One of them will be the best thing ever and maybe this is it. Okay, so you've shown us your Airtable. It's hooked up to this workflow, kind of like a Gentic system on the backend. What does that expose to end users?

36:32Andrew Mason:So let me show you this now, right? So it looks like it already set this up when I tried this demo earlier, and it found that. So it's already set up a game for me this weekend with Slay the Spire, a great dick building game. I've scheduled it for this weekend and created a request. And so now what's happened is it's gone out on its own and it's messaging other people who like these kinds of games and it's trying to build enough people to schedule a game. And this whole flow we're using N8N for. So basically what happens is you send a text to this phone number. We hooked up Twilio. It comes in and just does a little bit of basic formatting.

37:12Andrew Mason:then it looks up my phone number in the Airtable members table here and it finds out who I am and it figures out if I'm a user or not if I'm not a user it has a whole flow and this is the agent you can see there's these long prompts that basically do all of the routing that we've learned that says what to do if it's not a user I'm not going to focus on that one I'll focus on the if they are a user. So if they are a user, we have this like central agent and these are all the tools that it has access to. So these are all Airtable MCP tools. So you have something that can just like get a list of records, something that can create a new record.

37:58And the instructions

38:00Andrew Mason:for how and when to use that are all in this big prompt that we've put together, which you see gets quite long and it's just been like iterated on over time and it's crazy because like you'll see there's parts in here where it's just saying you know use the use the create record tool to to do x y or z and you just reference it in plain text and it knows how to go and find that

38:31Nabeel Hyatt:yeah you're not calling a function or anything like that you're just just literally writing down what you think it should go do and then it'll figure out how to find the function and use it.

38:39Andrew Mason:And so this agent available to your customers via text, so super simple interface, but is routing to your source of truth data for your business. And then it's engaging with other customers saying, I got somebody who wants to play this game this weekend for an hour, an hour and a half. If you're in, let us know and schedule it and it brings those people together. and as somebody who has put together children's birthday parties just even that seems very very useful and i can imagine we've got to turn this into a startup no third startup that's when you when you you've joined my club is when you're you're doing three but um what i imagine as a business owner though like it's cool as a customer that's nice it's a nice experience it's fun as a builder.

39:29Andrew Mason:But as a business owner, you are probably then getting much closer to, you know, your gentle break even goal of higher utilization, more bookings, more people with lower sort of person to person kind of grunt work that has to happen to make that happen. I'll just say, like, I guess so. We never thought of it that way, though maybe we should have. But it's just the nature of this enterprise that that's not the calculus that's typically going through things on i i will say though that um it's not about replacing a human job there's no like a human couldn't do this type of work at this level where you're going out and like contacting three members to see if they can play the game and when one of them says no you contact another it's like maybe you could do something like that but it for organizing a board game night.

40:25It just doesn't make sense.

40:27Andrew Mason:It would be too slow. So this is just, like Nabil was saying earlier, an example of the kind of experience that just couldn't otherwise exist.

40:39Nabeel Hyatt:Yeah, I would say a lot of our experiences started with a situation where if you had a, in that first group of things, it's the business advisor, the co-pilot, which you're right, if we had people that had done this work before and you surrounded yourselves with a bunch of advisors, those are human tasks that get you a couple of business plans. And we built up Python capacity planning tool and a bunch of other stuff that like way outside of even the scope of what we can talk about here that we just built. The second phase of this is it's just enabling experiences that you just never would have done with humans, period.

41:12Nabeel Hyatt:It's not replacing anything. We just wouldn't have offered these services. You would not have categorized by hand 200 plus, 300 plus board games into a category system you would not have set up a bespoke way that i can natural language say a board game category not even a game over text and say like i want to play an adventure game this weekend who likes adventure games that can play between six and eight o 'clock and then have that just like manifest itself into a space and then a table get booked very unlikely any of these products would even exist and and frankly the whole project wouldn't have exist without AI in the loop.

41:48Andrew Mason:And then before we wrap on this section, I just have to call out, looking at everything you've shown, it doesn't seem like you wrote much code to make this happen either. It seems like you wrote a lot of prompts and you hooked a lot of tools together, but I'm not seeing you pop open cursor in a repo. This all looks like kind of no code stuff that folks could use in their day-to-day, even if you're not a software engineer. There's a little bit of code in the N8N stuff. So I think with N8N, you still need to be a little bit technical with the way that things exist now. But that's just a matter of time before this becomes more and more something that anyone can do.

42:29Andrew Mason:We have repos for the website that we built, and Nabil built a whole ratings system for members to rate their games and get recommendations and stuff like that. So there's that, too. It's just we figured that was a little more boring.

42:46Nabeel Hyatt:Yeah, we also have a Python application where we took those personas that we talked about earlier. We fed them with an event programming and then a pricing plan. And then that goes into a Python application that uses Pulp and CBC to basically build out an integer linear programming application to figure out our capacity planning to basically figure out whether we can break even dynamic revenue business model planning. So we can set up plans, map it to personas, and then it just says, oh, if this is the utilization rate of this place, it'll max at 250 members, and then we can loop that back in.

43:23Nabeel Hyatt:So there is some heavy programming that goes on in some portions of this. But Claire, the vast majority of it starts from prompts and artifacts and projects and then document creation and that loop back and forth between producing a new document, adding it into the context window of like this is a new canonical truth of this project and then iterating and brainstorming from there.

43:45Andrew Mason:Okay. Let's wrap. This has been so fun with lightning questions. One no AI and one AI question. So the non-AI question is, what's your favorite game at Tabletop Library?

43:57Nabeel Hyatt:The next one is my answer. Like part of what I love here, and I know that's not a real answer, Claire, but part of what I love here is I actually really love exploring games. I think of it like a movie opening. And we have a culture at one point where you'd really care about the movie opening and you'd think about it and you'd think about the director releasing their next thing. And that's kind of where I've gotten to with games. And hopefully others can get that excited too.

44:19Andrew Mason:Andrew, do you have a favorite? it. Nabeel is such a big shot in the game world that he couldn't actually name one. He'd just alienate too many stakeholders. I like this game called Sky Team. It's a two-player game where you play as the co-pilots landing a plane. And it's really fun to play with my wife or my kids. So that's both a recommendation and an answer to your question. Okay. And I saw a little of this in your prompt. So Andrew, I'm gonna ask you my rap question first, which is when AI is not listening, how do you get to listen? And I will say I saw a lot of like all caps, caution, exclamation, exclamation in your prompt.

45:03Andrew Mason:So do you have any tricks that you fall back on when you want AI to really listen to you? I saw a really good video that I think Y Combinator put out recently. And they were like, when you get one, one change that I did as a result of that is when you start getting stuck in a rat hole and you can't get it to do the thing that you wanted instead of just like keep on hammering at it just revert back and try something different Nabil do you have a trick you have a fallback I think I I've certainly gone through all of the

45:32Nabeel Hyatt:stages of grief and anger and all caps to try and get the model to do what I what I want my more recent one is to just try and add context I like I think my most common thing now is to try and throw tokens at the problem. So a lot of times what I will do is copy the problem I have, throw it into another model, and then talk back and forth for 30 seconds to try and stretch out and elucidate the problem and add a lot more detail and then copy that prompt back either as a, it might be at that point as big as a PRD or something really detailed or so on and so forth, but just basically like it's confused and I need to give it a lot more direction.

46:08Nabeel Hyatt:And so let me then partner with a different AI to figure out how to tell what's really supposed to be doing.

46:11Andrew Mason:Okay, this has been such an adventure. I can't wait to bring my kids over and see what other cooler games we should get into. Nabeel, where can we find you and who should reach out to you?

46:24Nabeel Hyatt:Any founder building a wonderful AI product should reach out. That's where I spend all my time nowadays. You can reach me, Nabeel, N-A-B-E-E-L, on Twitter, wherever it's called nowadays, or my first name at sparkcapital.com.

46:37Andrew Mason:Okay, Andrew, and what about you? Where can we find you and how can we help you? First of all, if you happen to live in Berkeley or North Oakland, you should sign up for this thing or check it out. Go to tabletoplibrary.com and sign up for it.

46:53Nabeel Hyatt:Thanks for doing the business job, Andrew. That's very much appreciated, sir.

46:56Andrew Mason:But also I have to say, yeah, I'm the CEO of Descript. And the way this whole thing started was my head of marketing was savvily like, oh, there's this great new AI show. You should go on it. and I like sabotaging my press like normally like I normally do was just like I'll go on it but I want to talk about this other thing that I'm doing that I think will be more interesting but Descript is doing a lot of cool AI stuff too we just launched the first video editing agent so like cursor for video and I'll say like here's my like founder tip this thing this whole side project has been like the best thing in the world for rewiring my brain around AI.

47:42Andrew Mason:When you have your ongoing gig, you're kind of stuck in your existing patterns and people you have to rely on. Starting something from scratch that you actually care about where you couldn't do it without AI, it's the best. I completely agree. I have done the exact same thing. It has been transformative in how I lead in a bigger company. And I will do your marketing person a favor and know this was not paid, but we happily use Descript to edit this podcast. So we have been happy and it's how we get the great quality that you're seeing today. So Andrew and Nabeel, this has been so fun. Thank you for sharing all your tips.

48:20Andrew Mason:Good luck with the many businesses and have a great day.

48:24Nabeel Hyatt:Thank you. Thanks so much.

48:26Andrew Mason:Thanks so much for watching. If you enjoyed the show, please like and subscribe here on YouTube or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at howiaipod.com. See you next time.

From the publisher

Andrew Mason (founder of Groupon, now CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital) teamed up to open a physical board-game social club in Berkeley, with AI as their business partner. In this episode, they break down how they used Claude to generate a full business plan, model financials, plan the space layout, navigate Berkeley permitting, categorize hundreds of games using a custom Dewey Decimal–style system, and build an AI concierge that matches players with games via text. They also share how working on this side project helped rewire how they use AI in their day jobs—and why more people should use AI to build real-world things.


What you’ll learn:

1. How to use Claude Projects as your business copilot to create comprehensive business plans, financial projections, and space layouts

2. A workflow for categorizing hundreds of board games using an AI-generated “Dewey Decimal System” that makes game discovery intuitive

3. How they built an AI concierge service that matches players with games and coordinates group play sessions via text message

4. Why AI enables side projects that would otherwise be impossible due to time constraints and specialized knowledge requirements

5. A simple system for creating customer personas that inform your business model and event programming

6. How to use model context protocols (MCPs) to connect AI assistants to business tools like Airtable without complex coding

—

Brought to you by:

Lovable—Build apps by simply chatting with AI

Persona—Trusted identity verification for any use case

—

Where to find Andrew Mason:

LinkedIn: https://www.linkedin.com/in/andrewmason/

X: https://x.com/andrewmason

—

Where to find Nabeel Hyatt:

LinkedIn: https://www.linkedin.com/in/nabeelhyatt/

X: https://x.com/nabeel

—

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

—

In this episode, we cover:

(00:00) Introduction to the board-game social club concept

(02:44) How AI made a challenging side project possible

(06:14) Using Claude as a business copilot for planning

(12:53) Developing customer personas with AI

(15:45) Using AI to determine business viability

(21:02) Navigating Berkeley real estate and permitting

(25:18) Building an AI concierge for game matchmaking

(28:10) Database design with Airtable for non-technical founders

(32:04) Creating a custom board-game categorization system

(36:20) Demo of the text-based AI concierge service

(40:38) Enabling experiences that wouldn’t exist without AI

(43:42) Lightning round and final thoughts

—

Tools referenced:

• Claude: https://claude.ai/

• Airtable: https://airtable.com/

• n8n: https://n8n.io/

• Twilio: https://www.twilio.com/

• Cursor: https://cursor.sh/

• Windsurf: https://www.windsurf.io/

• Python: https://www.python.org/

—

Other references:

• Model context protocol (MCP): https://www.anthropic.com/news/model-context-protocol

• Tabletop Library: https://tabletoplibrary.com/

• Descript: https://www.descript.com/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

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