How to Scale a Profitable Agency with 0 Employees (Using AI Agents)

my brain kind of exploded a little bit. I was like, oh, so any business you can flip the sales model on its head.

Absolutely.

You could basically, instead of reaching out saying, hey, would you like me to maybe do this for you if you pay me and hire me? And versus saying, check this out, I made this for you.

Yes.

You want to work with me?

That's right.

Obviously that's going to be a better sales pitch. But now AI made that scalable. That was not scalable. That's exactly right. If I think about Matt Mazzeo, I think about I think about the word early. So, yeah, whether it was investing in companies early, you got, you know, you were part of a portfolio that had Uber, had Twitter, had, you know, tons of hits. And you were early at CAA to the internet trend.

Yeah.

Like you were saying, like, first one to sign kind of like YouTuber talent to a traditional Hollywood agency or get Hollywood talent to put stuff online. Now you're early-ish and early, uh, on the AI train. Like, you've been texting me for photos of myself and my house, but redesigned using a, like, AI style agent. So can we talk about this?

Well, it starts with my wife making fun of me. She's like, your entire closet is black and white. You don't buy clothes ever. Like, you default to the same exact things. It's like a laughable thing. So, uh, we took a, we took a few months and lived in Japan and Korea, and everyone on every corner is the most stylish person you've ever seen. They're all put together. I'm like, what is it that they all look like? they're out of a magazine and I look a schlub. And I realized that I've just never taken the time to do it. So I'm like, fine, I'm going to, I'm going to try to train this AI model, O3, which is spectacular now and has all the vision modeling. I'm going to try to train it like a Korean color theorist. And that's where I'm going to start. Have you ever heard of these things?

So I've seen on TikTok the idea of color theory. So they like hold up a bunch of swatches and they're like, this one brings out your skin, this one clashes, avoid these. Dude, it's like an allergy test for fashion. That's right.

Perfect example. And like, people spend like hundreds, thousands of dollars doing it. And if you get a stylist in the US, it's like hundreds or thousands of dollars. It's like, again, it's one of these classic like things rich people do that eventually like AI will open to everybody.

Right.

I'm like, I'm going to see if the vision models are good enough. So I run the color theory on myself and my wife and it tells me, okay, you're a soft autumn, which, you know, uh, I was going to say that. I appreciate that. For what it's worth, you're a dark winter, which I think is super, super interesting. But for me, it was like, here are your primary colors. And then I was like, okay, great. Like, what do I need to avoid? And then it gives me a list of like colors that I got to wear and it tells me how to put them together. And as I dig further and further into it, I'm like, oh, can you like give me a capsule collection that I could do? And I'm like, give me brands that I, that I like. Here's my, here's my measurements on like brands that I wear. Here's how I think about it. And I'm like, my wife and I are doing this and we start like building it for each other and then we start productizing it for friends.

And so you sent it to me and you were like, you basically sent me a, an AI version of me.

Yeah.

And then it had me dressed up way better than I actually dress up.

Yeah.

And then it was like, yeah, you can just like push a button and it'll buy this outfit.

That's where we're going to. So like, it's not there yet. And this is part of why, like, people laugh at like the AI rapper, but I actually think like there's a huge moment in time to just be like the rapper. You be the rapper and sell the service, sell the outcome and like do the work for somebody before they even ask for it. Like, I didn't ask you for selfies. I just found selfies of you. I didn't ask you for like your fashion sense and your color. Do you want a color theory? I just ran color theory on you, right? And like I gave you a final output of like, here's a bunch of looks that you're going to look great in. And I got to the endpoint of what you actually want.

So let's put the style thing over here for a second because this is golden nugget to me, number one. This is the one I picked up from you in the last few months, which is this key insight, which is that AI is not just a product. It can actually be AI can be the go-to-market. So what you're doing is very, very smart. And I think you have a few ideas that are in this bucket, but you're like, all right, what if instead of just using AI to, to, to do the job, I use AI to sell the customer, to get the customer on board. And what you're doing is you're basically saying instead of I as a customer have to find you, decide if I want to try it, sign up, pay you, and then you do the work. What you're doing is you're saying, let me just grab pictures of you. Let me grab pictures of your house. You got my house off Zillow or whatever. And then you were like, hey, here's, here's what your house could look like. Want to use my service?

Yeah.

And that, like, do the work up front.

Yeah.

Seems to be like, that's not casual advice. My brain kind of exploded a little bit. I was like, oh, so any business, any business now you can flip the sales model on its head.

Absolutely.

You could basically, instead of reaching out saying, hey, would you like me to maybe do this for you if you pay me and hire me? And versus saying, check this out, I made this for you.

Yes.

You want to work with me?

That's right.

Obviously that's going to be a better sales pitch. But now AI made that scalable. That was not scalable before.

That's exactly right. I think you've nailed it. Like, that's actually the thing that triggered for me, which is like, when I think about like, new technology unlocks, like I try to think about like, did it come with a distribution unlock too? Right? Like I got to start investing at a time when like mobile and social got birthed and like both of them came with totally new distribution mechanics. Like The feed, the algorithm, social sharing, the App Store were all like these greenfield distribution hacks.

Gotcha. So not just apps are new, but App Store is also new.

That's right.

Not just doing a connected tool, but oh wait, social sharing, which is going to make this thing grow.

Yeah, Zinga lets you like share natively as part of the product.

It's not just a social game, it's a social share.

That's right. All of it was baked natively into the product. AI doesn't really come with that, right? AI has like, this is why the incumbents are moving so fast. It like makes your existing product distribution much better, right? You can add auto-suggest, auto-correct, you can like put Gemini in every product. You can tell your Gmail to like, just respond as if you're me and like do all of these things. And if you're ChatGPT, like you were novel enough and early enough and powerful enough that you're now the dominant default for the category. But it didn't come with like new distribution for everybody yet, right? Like there was the custom GPTs that was like trying to get there. There's MCP that's like trying to get there, but nothing obvious. But what did change was it let you do the work in advance.

The cost of work dropped.

The cost of work dropped so dramatically that instead of selling the promise, you can just sell the finished work, right?

And so you sell the proof instead.

I think a lot of people are still stuck in this paradigm of like, you know how there's like all those headshot apps that came around? Like, that's kind of a perfect example. It's like, let's say nowadays it's like 2 to 3 cents to create like a high-res headshot, right?

Right.

Everybody was creating these like headshot products and saying, I'll make headshots for you. And you still have to go in and use the tools and make the headshots and upload the thing. But like, their photos are out there, right? Like, there's probably an addressable market of like, call it 10 million super high intent. Like, they all need headshots, right? You know exactly who they are. You can audit LinkedIn and just be like, their headshots are terrible. Like, we can make it much better. That's your target market. And you could literally just for like a penny, two pennies, like create a low-res version, right? Of it and sell it direct. Don't ask them, do you want to set up a whole new headshot? Just do the thing. Give them a new headshot and then use that as the entry point to a whole other part of the business. Like, I'll do the rest of your LinkedIn. Your LinkedIn could be optimized, right? The second order service can be the service that you actually end up selling, right? But you close them. You got the opportunity to meet with them and close them on those other things because you gave them the value without ever having to ask.

So you could theoretically what you could do is you could basically say, I'm going to do the color theory part proactively and for essentially free for everybody. And then I might even suggest a couple of looks. Yeah. And then if you actually—

if I can do it for you every day, do you want it every day?

Yeah.

And you want me to keep track of things that are in style, right? Do you want to personalize it over time?

Right.

Like, those seem like—

and then that's the, that's the upsell. But the kind of the initial sell is pretty powerful. And then you string it together with tools like Clay or whatever, which is like Mass, mass personalized outreach.

Yeah.

So, okay, so what do you have now as an entrepreneur? Now you have the ability to say, all right, for any given market, let's just take real estate agents as a market.

Yeah.

Okay.

I know who the agents are. I know what their listings are.

Yeah.

Let's say I had an app that could, with AI, could take your photos off your listing and I could stitch it together into a cool, like, Instagram-ready reel.

Perfect.

All right, easy. I can then go— I can go into a tool like Clay. And I can say real estate agents, California. I can get all those. I can put an AI agent that will go scrape all their listings.

Yeah.

Because that's all publicly available. Get their listings, get their photos, you do the AI wrapper thing, which says stitch these photos into a social video, a social optimized video. And then I literally just email that person, hey Steve, saw you had that listing on 410 Montgomery Way.

Built you a reel.

I built you a reel for it. I think it'll be really great. You could share this on your Instagram. You know, hope you, hope you like it. Let me know if you have any suggested changes. And the guy could be like, wow, this is incredible. Be like, cool. Would you like me to be doing this for all your listings? I think this actually will help you sell. Sign up for this. And like that sales process is now like what an engineer does versus what a sales guy does. That's right. Let's do another example, because when I heard what you were doing, which we haven't talked about on this yet, but that's okay. I texted Ben and I go, Ben, this is a billion-dollar secret.

Yeah.

Because if you actually learn like a differentiated, scalable, sales mechanic. It's like our friends who started doing Google Ads back in like '05 and they're like, dude, I used to buy clicks for a penny. And like, you know, friends who were doing e-commerce on Facebook back when it was like, you know, $1 CPM.

Yeah, right.

Or less than a dollar CPM. It's like those are billion-dollar secrets that like there's this arbitrage that can exist right now where this new sales model, new distribution model that's less tapped today.

Yeah.

So what's a, what's an example where you could use this?

I think the beauty of like most enterprise software is like you're, you're either helping them make more money, save money, or save time. And it's like most businesses are pretty focused on the first of those, like just help somebody make more money. And so you can kind of go and help almost anybody generate new business, generate new clients, right? And so like the exercise could just be like, hey, I delivered you new clients. Like imagine I am the person running sales for Company X. You can do this with O3. I want to help them generate new business. What are 2 or 3 new innovative ways that I could use O3 to generate business for this company? Just do that playbook for every business. It could be like start a listserv that targets all of the potential customers of that client. It could be create an Instagram account that like highlights that business. Don't even ask permission. Be like best HVAC service, Destin, right? And like create an Instagram account for that person. And do it at scale. And like, if anybody comes in his DMs, be like, hey, I got 3 new customers potentially for you.

Right.

I think those kinds of arbitrage is like now exist for basically every company, right? Because there's going to be this lag. There's always a lag between like what's possible today and like how long it takes the average person to end up figuring it out.

All right. A few episodes ago, I talked about something and I got thousands of messages asking me to go deeper into explain. And that's what I'm about to do. So I told you guys how I use ChatGPT as a life coach or a thought partner. And what I did was I uploaded all types of amazing information. So I uploaded my personal finances, my net worth, my goals, different books that I like, issues going on in my personal life and businesses. I uploaded so much information. And so the output is that I have this GPT that I can ask questions that I'm having issues with in my life. Like, how should I respond to this email? What's the right decision knowing that you know my goals for the future? Things like that. And so I worked with HubSpot to put together a step-by-step process showing the audience, showing you the software that I used to make this, the information that I had ChatGPT ask me, all this stuff. So it's super easy for you to use. And like I said, I use this like 10 or 20 times a day. It's literally changed my life. And so if you want that, it's free. There's a link below. Just click it, enter your email, and we will send you everything you need to know to set this up in just about 20 minutes. And I'll show you how I use it again, 10 to 20 times a day. Um, all right. So check it out. The link is below in the description. Back to the episode.

So you had some ideas that you had sent me. One of the ideas you talked about, you gave me a bullet point, which is, I think it's called the Mario, Mario Kart theory. What's, what is the Mario Kart theory?

Yeah, the Mario Kart theory is, uh, this is actually like, you could have made a lot of money investing in tech over the last handful of years. Um, or at least in the SaaS, if you just followed this one, if you just followed like, everything's better in multiplayer, like, uh, like build things that are like multiplayer by default, like Figma, Notion, uh, Airtable, Slack, Slack, like take the communication tools or the enterprise tooling and like make it real time and, and, uh, and cloud-based. Those things have network effects to them. Those things, like instead of—

Mario Kart's better with friends.

Mario Kart's better with friends. And so like, but like if I look at AI today, it's all siloed. It's almost like I'm having an individual conversation. Like where's, where's like group chat GPT? Like You and I are in a conversation all the time. Like, why isn't GPT in there with us? Why isn't it living with us in those social moments? Why do I never see your exhaust out of your feed? Like, there's a bunch of stuff you'd be fine with sharing. Like, there's a bunch of stuff that we'd all get better at. Like, Midjourney was right. Midjourney, like, built— like, it's almost like lost to history of 3 years ago that Midjourney was like on Discord. They were social by default, that you had channels where you could see everybody's like outputs. And it was like, kind of a magical experience, but almost nothing else went that direction. Like, it's all isolated and private and like hidden and like, it's a, it's like a travesty that like the outputs for the free tier of GPT are private by default.

Midjourney is a great example of bad is better because it's like the product design. You're like, wait, so, okay, cool. I download your app. Like, nah. You open up Discord, you join our Discord, and in the Discord there's going to be 1,000 channels. You know, there's different numbers, just hop into any one, and there's a flood of absolute random people generating absolute random images. Yeah, but it was actually kind of amazing because you go in and suddenly you're inspired. You see like, oh, that guy's using this to design t-shirts, this person's creating like anime, and then you see that same person change their prompt and make their images better. You're like, oh, I never thought to add that to my prompt. Let me copy paste that. So we were all teaching each other the thing. And this is like, you know, this is not the like chef's kiss product design looks sweet in a mockup. Like, no, but it was just like the hacky way to get going. But it actually had this tremendous bet. Like the, the one thing it was great at, which is putting you around other people doing the same thing. Yeah. Outweighed all of the downsides.

Totally. You know, that initial user experience and they could focus on just making the model better. Didn't have to focus on like front-end resources and how to think about it. And like, just, we know it's not perfect, right? We'll eventually get to the thing. But that was like model 5 or 6 by the time they built the destination site. Right. And it frankly feels like less social to me in a lot of ways. They have the feed there, but I'm not like seeing it the same way that I saw it when it was native in Discord. And so, right. I bet there's a bunch of tooling like that. Like the style, the style idea would probably be better as a social environment in Discord. Like you and I are different color types, similar body types. Maybe we should have the similar channel for our like right, for our area.

Because if I saw you actually, like, this would actually be kind of magical, right? Like, if I went in and I'm, let's just pretend I was also Soft Autumn, and I'm like, I'm in with my Soft Autumn, the Soft Autumn boys, we have our channel, and I see you actually like proactively doing stuff.

Yeah.

And you're prompting it, you're like, oh, I got a wedding coming up, and you prompt it, it gives you a really good recommendation, you actually like take action on it, you upload a photo of you in it, I'm like, damn, that actually worked out, you look good. Now your success kind of like triggers me. Inspires me, teaches me how to use the tool, and then I go back in and use it. Like, that's a fundamentally better experience.

More—

it's going to be a more powerful experience than—

that's right.

You doing this on your own. Me having to discover this, learn this, remember to use it, and then get the only the benefits are siloed in my experience, right?

I designed your— I redesigned your house like from Zillow photos. I'm like, that's a probably better in a social experience, right? Like I just delivered you the work, right? Like I used to have to sell you on the idea that I'm a great designer and call my references, right? Don't do any of that. Here's a, here, do you like this room? I can do the rest of your rooms. You have a different budget. You have iterations. I can do it all for you. But should, that should live in a social environment. Almost all of these experiences outside of like the health ones and the legal ones are probably good enough that like a free social tier would be like accretive to the value. And like right now we're all like these bonobos. Like you ever see the videos of bonobos with like the ants on a stick? Like they're like, they're like the first example of like tool use spreading. And it's like they put the ants, they put the stick in the tree, they get the ants out and the another banana was like, that looks like an ant lollipop. I like that. Right. And they go and do the next thing. And it's like, instead we're like cut off from everybody else. And so I'm the only one eating the ant lollipop and nobody else gets it.

I feel like that's a really big idea. Like, I think you could without— don't need to make a model. You don't even really need to make a new use case. You just have to like design a social experience of the same use case.

Social by default is always better.

Right. So is there anyone doing this right now? Like, is there any, like, have you seen any cool social, like, I want to basically take something like Claude, which Claude is so powerful. Claude's kind of losing the race of the individual user thing. But I'm just thinking like, what would be the Figma type of experience where you, you know, what would be the use case? Like, is it something like with work? So for example, um, you know, I have a lot of friends. We're all looking at how we can use AI in our, in our company. And everybody's kind of self doing the law, the stick in the, in the tree to get the ants where it's like, oh, you set up a thing where you connected it to your calendar and it, yeah, the workflows, it researches who you're meeting with and then it sends you the brief through text message and then you have that and like, oh, I want that.

How did you set that up?

And I have to like ask them for a tutorial, whereas I really should just be able to fork that.

Yeah. Right.

Like, and that's what I think Gumloop and some of these other guys are going to get towards where like, yeah, one person makes a great workflow. It's like that problem should now be solved for the rest of us. And we should just be able to fork that.

People are doing, I mean, like Zapier, there's tons of like, uh, recipes or whatever for like workflows that you can use. The thing that's missing is the social proof. The thing that's missing is like how many people liked it? What are the comments on it? Like, what are the likes? What are the, like the remixes that you're doing? Who's using it? Like if you're using it, that's a big signal for me. Like if I'm doing it and I'm like getting value out of this fashion thing, right? Like that's probably a good signal for you. Like, Those are things that like, I think tip people and it's what's missing. Like these were like lessons of Web 2.0 that are kind of like gone, right? Like they're just like, like we've almost like collectively forgotten a bunch of these things that were like, oh, social by default makes a ton of sense. Like all the social apps, all the like iOS apps went social. It feels like collective forgetting. And some, it does feel like a big market gap.

You know, one of the things I've picked up from you is that you have this, like, your process is sort of like, I go try to do a thing.

Yeah.

Firsthand experience. In doing so, I run into the problems of doing that thing. Maybe it's like styling yourself or whatever it is.

Yeah.

And then, and then learn by building.

Yeah.

And like, I, it's so funny because I thought of you because you started your career with like CAA and you're like this like kind of charming guy from LA.

You live in LA. I just thought of you.

I was like, this is like Hollywood pretty boy. And like, Actually, you're more of a hacker, tinkerer. Yeah, you focus on the pretty boy part. Yeah, no, but you're actually like a hacker, tinkerer type. And I'm curious, I don't know the full story, but like, I would bet that that's led to some very good things in your career, even though you're not building the end company. Yeah, but it's the learning by tinkering that led you to the investment that led you to the opportunity after that. Can you tell a story that—

Yeah, yeah, yeah. So during COVID I have a buddy, Brian Wagner. He's like one of the best product guys I've ever met. I like, back in the day, he was building a company. I was like, that's not the right company. But this is a guy who just like, I want to spend time around because we just— I love jamming with him. I love the way he thought about it. And so we'd always like built different products together. It was like our weekend hang. It was like the thing that we would do. And, during COVID we got obsessed with this idea of a product called Roadtrip, which is like a music listening product that you co-listening. And it was like you could talk while listening to music. And it's like it was this experience where like when we got into it, We would be in a room and I don't know if you've experienced this. You probably sit on a phone for like 5 minutes of silence, 2 minutes of silence, and it's like, I got to get off this phone call. It's like the most awkward thing. But if you sit in the— in a room with somebody and there's music playing, it takes all of the edge out and you could last for like hours in a room with a grown man and have like a conversation that dips in and out as long as there's music playing in the background. It's almost like the music creates the substrate that lets you pay attention. And we started building this thing and, um, you know, it ended up not working. We couldn't figure out retention. Turns out live is really freaking hard. Synchronous is really, really hard. But in the process of building it, we were like, God, Firebase just sucks. Firebase sucks. Every, like, it's like, I'm in the Google universe. Like everything is tied to the universe. Like if somebody, Brian, I remember this moment where he's like, dude, if ever you see a company, I was, you know, investing early stage at CodeTwo. It's like, dude, if you ever see a company that is like an open source Postgres, like Firebase alternative. Like, that's our ticket. A week later.

And by the way, from the outside, it just seemed like, uh, solve problem. Firebase does this. Yeah, it's probably fine, right? If you weren't building, you wouldn't know.

I would never have thought. I would never have thought. He's like, then we had built so many social products. It's like every time you got to go through the same thing. It's like you're stuck in this like Firebase universe. Then eventually you try to like cycle off of it and it's like a pain in the ass to migrate and you ever do it. And they weren't upgrading the product a lot. Now they're actually putting a little bit more attention because it's like their Replit competitor. But at the time there was like no development there. And so a couple of weeks later, it's like YC, I'm looking at the list of the YC companies. I'm just ripping through it and I'm like, Supabase, open source Firebase alternative. Right. And I'm like, okay, this is just, this, this feels like a great moment in time. And I'm talking to, I'm talking to one of my partners. He's like, I love this idea. And, and Ben Tossell, who's like an incredible tinkerer, builder, investor out there, was an angel in the company. He made the connection. Direction. And we ended up leading the seed round at COTU and did a Series A there as well. And, um, it's a great company. I love those founders and I think it'll be a great, uh, investment, but I never would have gotten close. I never would have thought about that idea if I hadn't experienced the pain first.

And so do you, when you're going into them, is it like, I'm doing this to learn, or I'm doing this because I think this is the next big hit and it just turns out that's wrong. And then the learning was like the consolation prize. Like, mentally, how do you approach that?

It's curiosity sometimes. It's because I'm solving a problem. It's because I have an idea that's been sitting on me and nagging at me and I just got to build it and get it off my brain. Sometimes it's like, I just think this is going to be a category that's going to be huge and I have to like understand it. Like I built a live or a video shopping product. I, um, I got upset. So I'd spend a lot of time with the team at ByteDance. Uh, and I, one of the, I used to spend like a few hours a month and we would share notes on like what I saw coming in the US and what they saw coming out of China. And it was just like a really fun jam with like the team at ByteDance. One of those sessions we spent on like video commerce and I was just like, you know, it was like 4 years ago, 5 years ago. And I was like, this is going to be just like such— it was such a massive category in China and nobody had cracked the nut in the US and you've seen attempts at it. And I was like, it just feels like somebody's like, we're all just close on it. I was like, I'm gonna go build in that space so I can understand why it's not working here and like, what's broken here. And so I built like a— my wife is a Korean expert and knows beauty really well. So we built like a— the first shop we built was like around Korean beauty products. And I like went through the whole process. I went and found wholesale. I went and spent hours at like different Korean beauty shops to like get a sense of like what were the products and like what was the full stack of a Korean beauty process. They told me how shitty my skin was. Uh, and like, I went through the whole process with them and built the store on TikTok and like did the fulfillment myself and was like going down. Because I think that's like, that's one, it's fun to learn these things. Two, the only way to do it is get close to the metal of it. And if you just approach it out of curiosity, like it's just a win no matter what it— maybe it turns into an interesting business. And at the very least, you've like seen what the pain points there.

Most VCs don't do this.

Do they? I don't know. Everybody's got a different process. I think like my process has always been like, I will be better at understanding the pain points. I think it'll resonate more with the founders if I can like cogently talk about how I've used the product. Like those things matter. And it's like you're, you have more authenticity and it's like, I don't know if other people do this, but it's like my best way of learning. Like I actually know what the product does. I actually use the product and it like makes me better. Like when I was talking to Amjad, from Replit, from Replit, who you did an awesome pod with, by the way. I love that, that episode. Uh, I love that product. I, uh, we were lucky enough to lead the Series B. I was a board member at Replit and, uh, partially because like I love tinkering and it was like a tinkerer's dream that you would like never have to worry. And I was technical-ish, but like never could have built like some of the products that I wanted to build. And it was like the idea that Replit would help me get closer to being able to unlock that felt like something that everybody would want. Turns out it was like perfect timing for like the entire AI wave as well. But like the way I got to, to spend time with Amjad was like, I was just using the product. Like the first meeting I ever did, I built a REPL. I was like, free to hang. And I was like, I learned Python to like figure out how to send him an app in a REPL that I could like, you know, pick a meeting time. And it was like VC courtship.

I like it. So what's their story with, with Replit and with Amjad? Because, uh, he seems like a real force of nature. Like when he came on the podcast, I just really thought like he just seemed impressive to me. He seemed like somebody who's got a shot to build one of these generational companies. And I don't know if Replit will— I'm an investor in it. I hope it succeeds. I think it could succeed. But like, I just think he was really unique and that product was really unique and the story of how he got there.

The origin story is amazing.

What stood out to you from him or that story?

I mean, just that he was always happy. It wasn't like a new thing for him. He like didn't have access to, you know, to the tools of technology, knew how powerful they would be and would like find whatever way possible, working in like PC bangs or whatever, like in his hometown and like to like just get access to the computer. It was like the same same thing that, like, you know, the— when, when people were, like, spending time at, like, the research labs in, you know, in Silicon Valley to, like, get access to their first computers, it felt like he was going through that, like, hero's journey, right? Just to get access to computers as a kid in Jordan. As a kid in Jordan. And then, like, you know, uh, and then he was obsessed with, like, spreading it to everybody. So he was, like, one of the first guys at, uh, what's it called, Code Academy. And, like, you know, he was— it was, like, the mixture of true believer technical enough to build it, knew what the pain points were for him and for like everybody else who was coming up, has like real mission to like make a billion, like there's going to be a billion developers. And if he has anything to do with it, he's like going to get to that endpoint. And then he's almost like an endurance athlete in the sense that he's willing to wade through like decade of boredom. Like it's like, it's sexy now because like there's Replit Agent and like you can build your idea and you can vibe code. And he's like, it feels like a wild roller coaster ride right now. But it was like years of wading through like school, like going to schools, building tools for teachers to teach kids how to code and like the infrastructure needed to full stack it and a religion around the fact that you had to full stack it. You couldn't outsource these things. And it was like all that minutia would like— there's a lot of people out there who are like, I'm going to build the ultimate vibe coding platform. It's like, You know, this whole moment we were in and like where it's like the idea guy's time and like everybody's like, now's the time for the idea guy. It's like the idea guy, like now you get to skip like what was the first 6 months to validate the thing, but it really just gets you to the entrance of the maze.

Right.

And it's like, now you've got to go through like—

What's up, idea guy?

Welcome. Welcome. You ready?

Yeah.

You up for this? Because the maze sucks and you're going to tear apart every idea. It's all that matters is like the number of iterations on the experiment you can run and like ripping that idea you had in half and like telling you, like the world telling you your idea is garbage. And like giving you the feedback that like is brutal and honest from your customers that they hate your idea. And it's like maybe there's a kernel of something from that idea that leads you to the next one. It's like the idea guy's time has come in that like we can validate ideas really fast, but it's like, I don't know if you've experienced this, but like just because you can build the thing, like, and we've moved from like your Apple Notes to like Repl with the ideas fully, the MVPs built, doesn't mean that you want to spend the next, you know, decade eating glass for that world. I have a lot of friends who are like idea guy, builder, product people who are like, I'm just looking for the person who wants to take this idea over.

Right.

Like, that's actually the job.

Yeah.

It's like the job is the, you know, going and spending time like courting a dentist to sell them a product.

It's like the same thing with people who are like, taste is all that matters now.

Oh dude, the taste coppers are—

Because it's even more, it's even, they're upstream of the idea guys. They're like, no, no, I don't even make the idea.

I just taste. I just judge the ideas. I hear another person talk about taste in this market. You know, you ever read the articles of Lee Sedol from a decade ago? Do you know this story? Oh my God, it's an epic story. Lee Sedol is like the Korean master of Go.

Okay.

Do you understand this moment that happened a decade ago with AlphaGo? AlphaGo is like everybody's like, chess is a known thing, but no one will ever get to AlphaGo. And it's like, there's more possibilities in AlphaGo than there are atoms in the universe was like the quote.

I remember hearing that.

Yeah, this is the quote. It's like, at least it all, you know, we're safe. And it's like, you know, Lee Sedol plays AlphaGo, and at some point AlphaGo makes a move, and it's like this absurd move that nobody's like, this is a— AlphaGo made a mistake. You know, all those possibilities have made a mistake. And it's like 78 moves later, the AlphaGo beats the shit out of the human. And like, he's sitting there looking at the mirror. He retires. It's like a sad story. Like, he retires. And it's like, you know, the quotes are things like, I never truly scratched the surface of Go. And it's like, You know, I'm embarrassed and I feel helpless, like the feelings of helplessness. And it's like, I feel like everyone, you know, is going to have that moment. And it's like all those people who are talking about VC safe, it's like, it's all about taste and psychology. Uh, all those people are going to experience like a taste moment where it's like Lisa Dahl, where they're going to be Lisa Dahled and they're going to have a moment where it's like, you're going to present their taste and the AI's taste to the end consumer. Cause ultimately taste is in the eye of the consumer. It's in the eye of the customer. And it's like they are the ones that are arbiters of taste. You think you're a tastemaker until you put like the burger in front of the person. They're like, actually, I like this burger more. It's like, but that's a McDonald's burger. You're like, yeah, I like the McDonald's burger. Billions of people like the McDonald's burger more than your like, you know, Saint Charles, Fort Charles burger. And it's like, I prefer this thing. And so you might, you know, it might not win the award, but it wins the, the choice of the consumer. And so I think all these people who are like, taste is our salvation, are going to get Lisa Dolls. It's going to hurt real, it's going to hurt real bad. They're going to run into the brick wall of consumer choice on taste.

Well, dude, this just happened. Like, remember, I don't know, rewind 5, 7 years ago and it was like self-driving cars, what people working on.

Yeah.

What's going to happen to the truck drivers? It was like the truck drivers and the grocery store checkout people. It was like, like, you know, we're just gonna have to find them new jobs. And then all of a sudden, like, DALL-E and these other tools came out. I was like, oh shit, it's actually us. Oh no, it's us first. It's the graphic designers, the copywriters, the— like, you know, like, what were the first things that actually ChatGPT?

Yeah.

And like the modern wave of tools were good at? It was like writing. They did like the fake podcast of Joe Rogan talking to Steve Jobs. I was like, oh, podcasters, all right, that's gone. Like, you know, it's just a matter of time, you know. And so I don't really think there's really any sort of like safe space. Yeah. But I definitely don't think it's the, um, oh, I have, I have unique taste. Because you're right, like whether the AI maybe has better taste or it takes 1 million shots on goal.

Yeah.

While you take one and it's just going to play the law, like the law of large numbers and get it, get it right just by doing so many variations. Like, yeah, I tried to write a movie script. I was like, oh, I want to write the opening scene of this idea for this movie I have.

Yeah.

And so I'm like, sit down. I'm like, oh, shoot. Like, the idea was really great. I told like 5 people that idea. They're like, that's incredible. This is great. You should do this. And then I sit down and I just actually have to do the work. I'm like, oh my God, this is so hard. How do I— where do I start? Are they in a cafe? Are they in a bar? Where do the characters— what do they say? And so I go to ChatGPT and I upload a script of The Social Network and I upload like all of Aaron Sorkin's like work and I'm like, all right, you're kind of like Aaron Sorkin. But you're also me. And, uh, you get— here's the idea for the movie, give me a draft. Gives me a draft, kind of sucks. I'm like, give me another one. Gives me another one instantaneously with no, with no, uh, ego about it. Gives me another one, gives me another one, gives me another one. And it eventually, like, it got pretty good at doing that scene.

And pretty good measured by your, your taste, by my taste, by your taste of what you enjoyed, right?

But what I'm saying is, like, even if— let's say my taste maybe is right or maybe it's wrong, either way it did 10 attempts before I could even lift a finger.

The volume was there.

The volume is going to win in a taste game. It's going to take 1,000 shots on goal. Same thing with like ads, right? Like if you look at like fashion brands that do good with Facebook ads, go look at their ad library. It's not like they have one David Ogilvy sitting in the room and he just comes up with this one beautiful ad. They're running like 1,000 ads in a catalog. Yeah. Quantitatively testing which one gets the highest ROAS. Yeah. And they're doubling down on that.

It's so funny because like we've gotten over the idea of taste in all these like really fuzzy areas of like human consumption and it's like taste on video taste. Like, turns out like people preferred the algorithm of ByteDance and TikTok to like your following, your, you know, programming on television. Like your years of study of what people are, you know, enjoying got replaced like by like the algo. Um, you know, I can't tell you how many mistakes I watched.

Uh, that's so true. The algo is literally the definition of taste.

It's your taste.

And it's already proven that the algo dominates That's right. You know, whether it's editors inside the company or it's me for myself, it's better than what I could do for myself. Even.

It's funny. And we make these mistakes all the time. I'm watching it. I mean, you could argue that Apple lost the entire podcast business based on like, based on their, their religion around taste. Like Apple found that. Yeah. So like Apple started the entire podcast movement, right? Like they owned every podcast got launched on Apple, right? And they were like, we really— on the other side of Apple, they're like, we really need to own the future of entertainment. And they're like, what is the future of entertainment? It's like great shows. It's HBO. It's taste. That's tasteful creators, tasteful makers, like things that are just like—

no slop.

No slop. But on the other side of the house, the volume was being made by people that didn't look like the top Hollywood creators and all of them, no, no product iteration, no help for monetization, no like featuring of them, no studio production, no tools, no budgets, no like give them metrics and data back. None of the things that you would do if you had like a million free creators doing things and building awesome audiences that turns out can now sway elections. And all of them start on your platform. And then you fast forward, it's like, where's the, where's the most of that consumption. It's like YouTube and Spotify. And you're like, they fumbled. And they fumbled because like they didn't think it was tasteful and they missed it. And it's like YouTube back in the day did the same thing. They actually had half a billion dollars for content. They, there was like the original—

Originals, right?

The originals. It was like half a billion dollars. And they came to all the agencies and say, we want your best creators. And we all went and pitched them $5 million channels and they gave a big budget. And then they gave like $5 million for the native creators, like Phil DeFranco and Michelle Phan got like little touches of like cash here and there. Like the only channels left standing were the creators, the native creators. It didn't match the taste profile of like the advertisers that were upstream of all of this shit, but they were the ones creating stuff that people wanted. I mean, Sam Altman's got like the initiation point for basically every new business that's getting built, right? And it turns out he ran YC for a long time. We're not like that far away from him saying like, hey, why not just build like a funding model into the next GPT and be like, somebody's talking about starting a business. I actually like that business. Like, do you think it'll make money? Let's provide them like credits. Let's provide them a little bit of funding to get going. And like, I don't know, does that change how investment works? Is that maybe like upstream of all of the tastemakers?

So what do you think it looks like? Let's say AI just keeps getting better. Yeah, there's no, there's no life raft for the taste guys or the idea guys or the whatever. Like, AI is getting better at all these things and you're going to have, you know, so what happens? What happens to us? What do you do? How do you think about that?

I think you just keep creating things that people want and like, you know, use the tools to piece them together. And it's like, just get to the final, get to the answer faster. Like, do customers want this thing? And give them, give the customers what they want. That's true north. Like, build something people want. Like, it's the YC mantra. It's like, build a product people want. And it's like, how fast can you get the product to people that they want? And like, How many times can you iterate on the thing so that eventually you get the thing that people want? And it's like, just laser focus on that and cut everything else out of your life. And like, that's how you build most of these, like, scaling businesses, right? And it's, to me, that's like, uh, that's never going to go away. People are always going to want things and you can use these tools to provide those things to them. And there's probably a good arb for, for the next long while. Like, we got a long period of time before this stuff filters through the economy. Because it's not how fast the technology is moving, it's how fast people adjust their reality and their habits. And that's like the friction that actually exists here. Technology is mind-boggling, but like my mom learning how to second brain is like, even you and I learning how to second brain is really hard.

Do you, uh, do you have any other AI sort of theories or frameworks that are interesting that you've been noodling on?

Yeah, I've only, I've made, uh, I made 3 AI investments post-COTO. Um, as an angel. All of them follow the same kind of framework. Um, one of them is to a buddy of ours in the, in the travel space. And the other two are founders that I backed before. Um, but all of them are basically agent platforms. Um, one's called Cognition, which is like the maker of a product called Devin. And the founder, Scott, was a founder that I backed once before. And Scott is like a genius, correct?

He's an actual mathematical genius.

Among many things. One of the, one of the things I was riffing on was like, it's possible that Devin is just Scott in the background answering all the coding questions because he's so good. And then another product is called Augment. It's Harish Abbott, and Harish was a founder of a company that I was on board of called Deliveroo, which was like third-party logistics for everyone. It was like Amazon Prime for everybody. He worked at Amazon in fulfillment and then built Deliveroo, sold it to Shopify for a couple billion dollars. And like, Harish is one of those humans where like, if you could imagine what the ultimate like logistics hire would be, you would hire Harish. No detail escapes him. He doesn't mind staring into the abyss of like a warehouse and figuring out how to optimize every minute detail of like product comes in. Where does it go? What platform? How do you get optimized? What's the routing down to the minute? Like, he's that brain. It's just his— it's his gift. It's his dark gift. And so both of these people, actually all three of these people have these dark gifts where it's like you could never in your wildest dreams hire Scott. You could never hire Harish to do your logistics. But what you can do now is they've like, they've built these platforms that are agentic. And so it's like, imagine if like the reinforcement training was done by the ultimate employee and that was priced at tokens.

What does that actually mean? So like they're building an agent that's going to be like, let's say your logistics employee, but he himself is literally like kind of auditing the, like the answers.

He and the team that he is building are saying like, hey, we know exactly what goes into building world-class fulfillment and logistics. We've done it at Amazon. We did it at Deliveroo. Like, I know all the details. Now you've got a company that's an SMB, it's an e-com, and it's like, you don't know the knowledge that I have, but I can program it into, into an agent so that like all the workflows that you're eventually going to have to do, this agent can help you with. And it'll give you the things that would otherwise take you a lot of time, even if you were the best in the world at, it'll do those things automatically for you. And so I think we're moving to this world where like the best, the best at a task will be able to productize themselves as these agents and deliver.

So, you know, when social media came out, yeah, one of the cool things that happened, one of the reasons why there's this word influencer is because prior to social, the only people you knew who did a thing were the people around you. You were limited by your geography.

Yeah.

And the internet, the superpower of the internet is that it vaporized geography. So, you know, like We, when we had a baby, we're following these like it mom influencer types who are teaching you like how to like get your baby to sleep and like little tips on, you know, swaddles and diapers and all these little things. Like I'm getting the best mom coaching and dad coaching from like not just my geography, but like the world. And those people became, so the best teachers were not teaching in schools anymore. The best teachers were teaching on Instagram and YouTube and other places like that. And they were getting millions and millions of followers because like the best teacher actually should have a few million students. Yeah. And so the best got rewarded in that way. And so that's what the internet, you know, like, like last 15 years has done. And now with agents, it's kind of the same thing. It's like the best employee. You're no longer limited to who you can afford or who's nearby you, who you can hire locally, but actually like, no, globally, who's the best at travel planning and booking? Who's the best at logistics, you know, workflows, planning and analysis?

Who's the best coding agent?

Who's the best, who's the best engineer, you know, right? It's actually not who's the best engineer is who's the best engineer, period. Yeah, he can program himself in the same way that like content creators were able to like make pieces of content that scaled. And, you know, I can go to sleep and millions of people can listen to this podcast. And now they're doing that with like a piece of software, a piece of code that's going to actually like take their brain and be like, yo, I got, I got that guy's brain here in this piece. Yeah.

And do the digital work that they would have done for you. Right.

And they can now— and just like the best teachers have millions of students, the best employees now actually work for millions of companies is what's going to end up happening.

Yeah.

Yeah, that's amazing.

I want to do some stories with you.

So I have here—

oh, this is scary pictures. These are scary.

We're gonna draw a card, and then I want— is there people that you've encountered in your life? I want you to tell me some stories or story time. Take a card.

Yeah.

All right, show the camera. Who'd you get?

I got Peter Thiel.

Peter Thiel. Do you have any Peter Thiel, uh, either lessons learned, funny encounters, interesting stories, seeing him in action? What you got on Peter Thiel?

Uh, the only time I've ever encountered Peter Thiel was on the opportunity to invest in Replit. We were both going for the opportunity, and I think when you go against somebody like Peter Thiel, um, you plan to lose in most cases. Uh, and I didn't, I didn't end up, uh, losing the opportunity to invest in Replit. And I think part of it is like the realization that like any given Sunday in, in, in a lot of games, like a lot of people count themselves out, but on any given Sunday, you have the opportunity to, to, to pull out a W. And, um, I, I love that product. I love it authentically. Like I use it all the time. I love the vision of like empowering like a billion people to build the companies that they want to build. And to like, I feel viscerally like the tinkerer's dilemma of like, I'm not an expert. but I wish that I were, and I wish I could bring this idea to life. And that software is this like bicycle. And I don't, I'm like, I'm on a tri— I'm on a tricycle. I'm on like training wheels at best. And like, this thing makes you feel like you're on a motorcycle. And it's like, I love that feeling. And if you can tell that feeling to somebody and get them as excited about it as you are and use the product and obsess over the details of it, like I would send Amjad like every product thought I had, every, like I'd have, like I'd have shower thoughts about it. I was like, you know, whatever. And it wasn't like work. It wasn't like, you know, the art of the VC deal. It was like, I just genuinely, I genuinely loved it. And then I think there was a moment where, like, where he was like, I can have a guy who's probably one of the best on, you know, investors of all time, or I can have Matt. And Matt loves me. And, and, uh, and that was his choice. Um, and so So I think that's the— I think the lesson is like, if you, if you really do the work and you really love it, like, you might not win them all, but any given Sunday you could pull out the dub. Bondo. Who you got? David Bonderman.

Okay, tell his story. Who is he and what's your interaction with him?

David Bonderman passed recently. David Bonderman was the founder of TPG. David Bonderman, uh, was a guy I got to know, um, later in life. He worked with a very close friend and mentor of mine, um, named Rick Hess. And he was during, during my sabbatical, one of the things that I did was like, I'm just going to go and try to spend time with people who I've always admired and never really gotten to, to meet. And David was on the shortlist. David had ultimately been part of the group that acquired a majority position in CAA. And I'd gotten my first exposure to him there. And he had just had this like incredible storied career of like how he, you know, he ultimately, you know, he was a huge investor in like the airline industry and, you know, uh, had owned sports teams and was like a titan of industry and did it his way.

And what was his come up, by the way? Because like, you know, that's cool stuff you do at the top of the mountain.

Well, he worked for the Bass family. He was like, uh, he like helped build like the investment strategy for the Bass family in Texas. And ultimately like pivoted that into— I think the first investment was like Continental Airlines, where he made his first real, like, buku exit and ultimately ended up building TPG into like one of the titans of the private equity industry. And I got to spend a bunch of time with David, like hours at a time. He was like the kind of guy where like he was late in life, but he still had it. Like he had— he'd have these days where he was just like as hot and fired up as anything. And so So some days it would just be like, let's just spend time talking about his job and his career and like lessons along the way. And then other times—

sorry, how did you do this? So you're on your sabbatical, you're like, I want to spend time with these people. Would you call them up? You're like, hey, can I just come hang for a couple days? What do you say?

I called Rick Hess and Rick was building a new strategy for investing. I was just helping friends. And he was like, I was spending time doing, you know, doing— I treated like all of my friends and family kind of like I was still in the portfolio VC mind. I was like, I'm going to treat them all like portfolio companies. I'm just going to go do things for them that matter and help. And so I would help friends like start companies. I would like go over and clean out their garage. I would like just, I had time for the first time in my 20 years. And like, I just wanted to spend time with people that I loved. And I had a list. I wrote a list of all the people. And I like would say, hey, I have time for the next couple of weeks. Can I help you on something? And so Rick was like, well, I'm building this thing and I'm partnering with David. He's like, why don't we go over and talk to him about it. And one of those trips, he was like, hey, David's really interested in AI. Will you like put together some thoughts? And I was like, 100%. And so I got to go and spend like a 3-hour session with Bondo. And I was just like laying out where I saw AI going. I'm like showing him Midjourney. I'm showing him like ChatGPT, you know, and, and like just walking him through all the new products. And, uh, and he's just silently like kind of like riffing on it and like asking a couple of questions here and there. And, um, And at the end he's like, so what are you going to do? I'm like, I don't know. I'm going to invest in a couple of friends who are smart and building stuff here. I'm like, what would you do? And he goes, I'd buy railroads. And I'm like, okay, this guy's— maybe, maybe he's just gone crazy. Maybe he's gone crazy. I'm like, I didn't understand what he meant. I'm like, you got to explain that to me. I don't know what the hell you're talking about. He goes, well, there's two ways to play it. One is these— this world is moving so fast that everything is changing. And it's like if you built software today or you build a product today, it feels like it's moving so fast that it could be obsolete in 6 months. And so that's shifting sand. You can play towards the bleeding edge, but that's where everyone is going to be playing because it's shiny and it's fun and it's distracting. Or you can buy a railroad and it's like, think about the things that in the times of most change are still going to be here. And it's like, focus on the industries that aren't going anywhere. And it was, it was like this moment where you're like, oh, I'm talking to like business Yoda. Um, and it was just like a really interesting framework. And it's like, I think does apply is like the business that, that I've been, that I ended up spending a bunch of last year working on is in a really old, dirty industry that is like going to be around forever, but applies these tools to it. And so I kind of like met him in the middle. Which is like, I was going to use the tools that are available today to help an industry that I knew would be stable in the face of all of this change. And so he was just like one of those guys where he could like pull out an invest in trains and have it be like one of the most incredible business, you know, pieces of advice.

All right. We got 3 more.

I think the thing that I pulled from, from Mark was like the idea that like where venture was heading and the institutionalization of venture, and it kind of feels to me like we're at the almost the apex of that. Like when I joined this industry, like there was all of this tribal knowledge. There was like things that were hidden secrets.

What's an example?

Well, like, you could like, like how to write a term sheet was like unknown. Like how to do a closing process was unknown. Like how to, you know, the real mechanics of the industry were unknown, let alone like the metrics of like what is good, great, bad growth metrics or retention or net dollar retention. Like a lot of venture today feels like like it's really like institutionalized and it feels like even like further out we're at this point of like the industry where it's like the knowledge is all shared, it's all public. People have like posted almost as much institutional knowledge about an industry as possible. We have like documents like the SAFE that like revolutionized it. Like YC created a whole process for like how to institutionalize fundraising, the handshake protocol. Like we protocol the industry. Today. And it's like, we're at like the furthest end, maybe not the furthest end, but we're like the mature part of this industry. Like when I got into it, there were like 10 seed funds in market that like, you know, you didn't have to be good. You just had to be alive to like go and find these things. And there wasn't a ton of competition. There weren't like mega funds coming in and doing seed rounds. It's like you met a founder, you liked the founder, you went to YC, there were 50 other people in the room. You kind of like said, hey, I like this one, let's do it. And you got to a handshake on a on a note. Mark, I think, saw where the world was heading on this. He's like, all of these asset classes are maturing and we're going to build like a much bigger platform for it. And I think was inspired by a lot of the CAA mentality early on of like CAA shifted the way that agencies had been done. It went from this like, I represent one client with one deal and it's like boutique, but also like strategically, like Ovid had this insight that like if I rip an agent away from another agency, all their clients come. And it was like, whereas at CA, one client sat in the middle of 10 agents with each of their own, like, personalized expertise. And it's like in VC, the same thing kind of existed. You had one, one, one VC, you had this boutique, you're like, I've got this board member, that's my person. And then Adresen comes along and it's like, no, you've got all of us. And we all come with this like value proposition. And it's like recruiting and marketing and all of these services and he like, it was the realization that like VC was a service industry and institutionalizing of that, that like changed the way that a lot of venture was there, like had been done. And then everybody rushed to create platforms and teams and like structure because they were just beating people on that, on even if it wasn't like effective, right? They pushed the edge of that and they owned the brand of that, of like what a platform VC could be. And the other edge you had like Benchmark and, you know, Founders Fund and like people who are like, you need me and, or Founders Fund where you're like, you don't need anybody, right? You know? Um, so I think what I took from that was like, you can look at an, uh, at any industry, VC included, and like bring a new institutionalization to it. And I think they're still doing it. I think they just acquired Turpentine, uh, and Tornberg. And it's like the realization that like one of those edges that you're competing against is like distribution, media and You know, if you can bring customers, right? Like, what do the startups really care about? It's like customers and attention. The scarce resource is attention. And so it's like we're going to build attention into the offering. And it's like that feels again ahead of like the customer-first centric, like customer-centric, like response. And it's like most VCs were selling things that weren't necessarily like what the customer needed, right? It was capital.

What's that guy's name? Gilly something. He invests in Wiz and like every security startup. You know, this guy, basically he was like, he unbundled the Andreessen model. He's like, cool, we're not going to help you with, you know, marketing or recruiting. Like, we have a network of CISOs at the top 500 companies and you'll get to $2 million in ARR if you invest with us.

Yeah.

And then to those guys, he was like, hey, you're going to own a piece of this portfolio.

Yeah.

While you're sitting in your job, you're going to also be a venture investor, a venture partner in our fund.

Yeah.

And like, like kind of created a little bribery network that like actually worked and actually is like—

Turns out to be really effective.

Huge, huge results. Like, you know, way outperforming results by figuring out that platform. Yeah.

And I think like those are like what he's continuing to do is find like what those gaps are, what the customer really wants. Right. And it's like, if you could tell me like, oh, I want revenue, like I want— that's what I really want. And you can deliver that. That's pretty incredible.

And part of what the startup founder wanted was like, I want, you know, the brand A16Z.

I want cool. I want cool.

I want to be at the— I want Andre Iguodala to be like at our— I want to meet him. Like, I want these different things that, you know, again, just work backwards from what actually resonates.

Most VCs were selling cool, right? They were selling, they were selling, uh, maybe not cool. They were selling, uh, the promise of de-risked, right?

Credibility. Yeah.

The promise of credibility that we, that we were something that had been like validated. They were selling like, if you got a Sequoia investment, like, that's like, this is a real business. They've, they've looked at billions, like how many trillions of dollars of market cap or like from those people? We're among that. You said you felt the association with market cap. All right. Derek Jeter. I have, I have one absurd Derek Jeter story. That's super funny. So one of the things you realize at a talent agency and being around like like A-list stars all the time is that like a lot of people go a little bananas. Um, there's almost no equivalent though for sports stars because something embeds in your brain when you are a little kid that these people are like larger than life. And so I am a young VC at Lowercase and Derek Jeter and his partner are starting like a media company. A sports media company. And they're like, we want to spend time. And like, I saw all of this, anything like media and tech, I was like, I saw for years. And so we like go out for a dinner and we go out to this nice restaurant in Beverly Hills. And we're sitting down, it's the three of us. And up to the table walks a guy. And the guy is like the thickest, deepest New York accent that you have ever heard in your entire life.

He's like, hey guys.

And like, He sees Jeter and he's like about to talk about the specials and his face melts. The guy almost like he gets like time is a flat circle and he is lost. And it's like one of those moments where you see him like, like reverse age into an 8-year-old. And he's like, this is like the moment of his life. And so, uh, he's going, he's like captures him like, Mr. Jeter, Mr. Jeter, like I'm a big fan. He goes through the whole thing. And at some point we all order the same thing. We order like the special that the guy recommends. It was like truffle pasta. He comes back to the table a little bit later and he's like, you know, it's fresh truffle on top. And he gives me a little bit of fresh truffle and he gives the his manager a little bit of fresh truffle. And then he's over at Mr. Jeter and he looks at Mr. Jeter and he's putting the fresh truffle on and it— and he just like, he— his brain freezes, but his hand doesn't. And it, it gets to a point where it is, it is so funny that we just start laughing as it's happening because it is an ongoing mountain of truffle on this plate.

It is—

the whole plate is black. It is a—

it is—

it must have been hundreds, hundreds of dollars of fresh truffle on Mr. Jeter's plate. And he's like, he's just looking at Mr. Jeter and he's like, I think you got it. And it was just one of those moments where you're like, it's really funny to watch people in that moment of their life. I don't have, I don't have like a good lesson from it.

At least have like a different level of cool.

It's like, it's another thing. It transports you to being a little kid. And so, you know, I've had, I've had one of those experiences myself.

And, uh, yeah, well, this might be the one.

That is, that is, uh, that is the one. I grew up as a, as the most diehard of diehard Lakers fans. I grew up in LA. Uh, I went, I, I was a, uh, I went to college, uh, during, during the Shaq-Kobe years, in high school in the Shaq-Kobe years. High school, uh, you know, Christmas was like Laker game, uh, on TV. Like, that's what we did. He's one of those people for me that was like, I got to watch this guy and then I got to be obnoxious at college, like watching this guy beat the crap out of the Celtics. And it was really fun. But as a— again, at Lowercase, I had an opportunity. There was a brief moment in time where I was managing director of a fund called Lowercase 13, which was a Kobe Bryant partnership. And it was like for a split second.

How does that happen? Kobe reaches out.

I had a friend who was advising Kobe. Her name is Betsy Skolnick. And Betsy said, hey, Matt, Kobe is, I think he'd been injured at the moment. He was like, he's thinking about what comes after basketball. And he's always been obsessed with tech and venture. And he really wants to learn. Will you come down and have dinner and spend time with, with Kobe and teach him a little bit about venture capital? And this is my Jeter, like, like truffle moment. Like, I'm like, let's go. I'm ready. Like, I'll get, do you want me to come now in the car? I'll come right now and we can do it. And, uh, She's like, great, we'll set up a time in the next couple weeks. You can come down. So Chris and I go down and have dinner with Kobe, and we like sit there and he's like asking questions. And it was like one of these things where you can kind of tell some people like whether they have like, um, the second gear of curiosity. Like sometimes they ask the surface question and then there's another layer of curiosity where they ask like every relevant follow-up question that you could imagine having been in the industry for a long time. You're like, oh, this person's gone through and like they have real depth of curiosity. They want to know the details. They don't want just the surface answer. They want to be like, but how? This is actually what makes you great at like podcasts and interviews is like you do the second question. You don't just leave it at the first. You do the follow-up. And he did it for the entire— it was like a 3-hour dinner. By the end, he was just like, this was awesome. Thank you so much. I'd love to find ways to do this again. Will you send me stuff that I can read? And I was like, okay, I'll send him some stuff that he can read. So I put together like a, like the, the essential reading list of Venture— every blog post that I ever loved. Like I'm going through all the Gurley posts and the Wilson Post and like all the, all the stuff and, uh, thinking that he would like never read it. 2 AM, I get a text being like, I read that post. And it was just like, whoa, he was like in it. And he would like text and like, we'd have these conversations in the middle of the night. I was like, what's this? When is this guy sleeping? It must be like going crazy because he was injured. He's like, just like texting. And then eventually he goes, I really want to go spend some time and meet, like we'd suggested, like I was like, you can come with us and go to San Francisco and meet a bunch of the startup companies. He's like, I'd love to. Again, thinking like, he'll never do it. He's like, let's go. When, when, when are we going? And so we take him up to San Francisco and we go to see a couple startups and we spread it out. It's like early stage apartment startups. And then we go to Twitter and, uh, and we do like the tour of Twitter and Twitter had just bought Vine and we're like walking around, we're onboarding him to Vine and doing the conversation with Dick and Adam. Uh, Dick Costolo and Adam Bain. And he's like, I want to see the whole place. So we go down to like the engineering floor and he's walking past one of the, like the hang rooms for the engineers. And there's a kid in there and, uh, there's Pop-A-Shot basketball. And the kid, have you ever watched those people who are like savants at Pop-A-Shot?

Yes.

And they can like both hand it. And it's like, they go into like whatever the fourth gear of like the Matrix, you know, they're in it and they're like both handing and like, yeah, they look like the Tesla humanoid robot. That's just like, yeah, you're like this guy. Is that to the tee? And Kobe looks in and he's like, I got it through it. And he walks up behind the guy and he goes, I got next. And all the engineers see Dick and Adam, and then they see Kobe and they're like, holy shit, Jimmy's about to play Kobe! And they rush in and Vine has just come out so they're all taking video of this thing. And Kobe goes— bang, bang, bang, bang, bang, bang— hits 80. And then Jimmy goes and it's like, bang, bang, bang, bang, bang, bang, he gets 82. And the room erupts and it's the greatest moment in this guy's life. He has never never been like it. The whole world, like, it's like no one will ever believe this moment, right? He'd be like, I beat Kobe at Pop-A-Shotty, that guy. And like, you expect every— you expect Kobe to be like, oh, congrats, dude, high five. And I just remember the look on Kobe's face where he was like legitimately pissed. It was like, it wasn't like a fake piss. It was like, I'm buying one of these things, right? Never fucking happen.

Yeah, I will destroy you the next time I see you.

Never letting that shit happen again. And he like walks out, uh, deletes his Twitter account.

Yeah.

Anyway, so it, I, it It was pretty incredible, like getting to spend the time with him. And then, uh, yeah, we, he was like, hey, I really want to build a shop. Um, and so for a brief moment, we had like a side fund that we were putting together with Kobe and we made like 2 investments. Um, it was like one of them was ended up being Stripe out of that fund, but he had a, he had a business partner who ended up like trying to renegotiate and we don't do those kinds of things.

So anyway, Matt, full of stories. This is amazing.

Super fun. Thanks for having me.

Thanks for doing it.