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

Summary

Podcast Summary: "How to Scale a Profitable Agency with 0 Employees (Using AI Agents)"

My First Million hosted by Hubspot Media features an engaging conversation between Matt Mazzie and Ben Tossel, delving into innovative business strategies enabled by artificial intelligence (AI). Released on June 6, 2025, this episode explores how AI can revolutionize traditional business models, particularly in scaling agencies without the need for a large workforce.

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1. Flipping the Sales Model with AI

Matt Mazzie kicks off the discussion by reflecting on a pivotal business insight:

"My brain kind of exploded a little bit. I was like, oh, so any business you can flip the sales model on its head." [00:00]

Ben Tossel concurs, emphasizing the potential of AI to transform sales approaches:

"AI is not just a product. It can actually be the go to market." [03:00]

Key Points:

• Traditional sales models involve actively reaching out to potential clients, pitching services or products.
• AI enables businesses to reverse this approach by proactively delivering customized solutions to customers without initial contact.
• This shift from soliciting interest to showcasing proof of capability can significantly enhance scalability and efficiency.

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2. AI in Personal Styling and Scalable Services

Ben shares a personal anecdote about training an AI model for color theory in fashion:

"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." [01:09]

Matt adds humor by describing the AI-generated makeover:

"And so you sent it to me, and you were like, you basically sent me an AI version of me... dressed up way better than I actually dress up." [02:48]

Key Points:

• Utilizing AI for personalized services, such as fashion styling, allows agencies to offer tailored solutions at scale.
• AI can analyze individual preferences and provide customized recommendations, enhancing customer satisfaction.
• Productizing such AI-driven services for a broader audience opens new revenue streams with minimal human intervention.

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3. Distribution Mechanics and New Technologies

Ben contrasts AI's distribution capabilities with those of mobile and social platforms:

"AI doesn't really come with new distribution for everybody yet. It didn't come with like new distribution mechanics like the feed, the algorithm." [05:16]

Key Points:

• Unlike previous technological advancements that introduced novel distribution channels, AI primarily enhances existing platforms.
• Incumbent companies leverage AI to improve their product distribution, but broader distribution mechanisms for AI-driven services remain underdeveloped.
• There's an opportunity to develop new distribution strategies tailored specifically for AI-powered offerings.

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4. The Mario Kart Theory: Multiplayer and Network Effects

Ben introduces the "Mario Kart Theory," drawing parallels between multiplayer gaming and product design:

"If you just followed like, everything's better in multiplayer. Like, build things that are like multiplayer by default." [11:38]

Key Points:

• Products designed with multiplayer or collaborative features inherently benefit from network effects, enhancing their value as more users engage.
• Integrating social elements into AI tools can foster community engagement, knowledge sharing, and collective improvement.
• Encouraging collaborative use of AI can lead to more robust and widely adopted solutions.

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5. Making AI Social by Default

The conversation shifts to the importance of embedding AI within social contexts:

"AI has like, this is why the incumbents are moving so fast. It, like, makes your existing product distribution much better." [05:16]

Matt and Ben discuss how AI tools like ChatGPT could be more integrated into social platforms to enhance user experiences:

"Almost everything was baked natively into the products. AI doesn't have like new distribution yet." [05:16]

Key Points:

• Embedding AI directly into social platforms can amplify its reach and utility.
• Social integration allows for real-time collaboration, feedback, and iterative improvement of AI-driven services.
• Creating AI tools that thrive within social ecosystems can lead to more organic adoption and innovation.

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6. AI and Taste: The AlphaGo Parallel

Ben draws an analogy between AI's impact on creative fields and AlphaGo's influence on the game of Go:

"At least it all plays AlphaGo. And at some point, AlphaGo makes a move... and it beats the human." [29:39]

Key Points:

• AI's ability to iterate rapidly and analyze vast datasets allows it to excel in areas traditionally dominated by human taste and creativity.
• In fields like design, writing, and strategic games, AI can outperform individual expertise through volume and pattern recognition.
• The "taste game" shifts from subjective human judgment to data-driven AI optimization, potentially redefining standards and preferences.

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7. Venture Capital and Investment Strategies

Ben reflects on his investment philosophy, emphasizing hands-on experience and understanding pain points:

"My process has always been, like, I will be better at understanding the pain points." [23:51]

He shares insights from interactions with prominent figures like Peter Thiel and David Bonderman, highlighting the importance of authentic engagement and problem-solving:

"I use the product. And it, like, makes me better. Like when I was talking to Amjad from Replit... I learn Python to, like, figure out how to send him an app in a Repl." [25:03]

Key Points:

• Successful investing requires a deep understanding of the product and the problems it addresses.
• Building authentic relationships and genuinely using the products can lead to more informed and effective investment decisions.
• Investing in foundational technologies and platforms that address enduring needs ensures long-term value and stability.

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8. Personal Stories and Interactions with Influential Figures

Ben recounts memorable encounters with industry leaders, illustrating the human side of venture capital:

"The only time I've ever encountered Peter Thiel was on the opportunity to invest in Replit." [43:01]

He shares a heartfelt story about interacting with Kobe Bryant, demonstrating the profound connections that can form in the business world:

"We take him up to San Francisco... he plays Kobe at Papa Shotty." [59:29]

Key Points:

• Personal experiences and stories provide valuable lessons in networking, perseverance, and the unpredictable nature of business relationships.
• Engaging with influential individuals can offer unique perspectives and opportunities for growth.
• Building genuine connections often leads to unexpected collaborations and successes.

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9. Concluding Insights

Ben emphasizes the enduring importance of building products that meet genuine needs:

"Build something people want... that's true north." [37:02]

Matt and Ben discuss the evolving landscape of AI and its pervasive influence across industries, stressing adaptability and customer-centric approaches:

"There's no safe space. If you could tell me like, oh, I want revenue, like I want... that's pretty incredible." [37:15]

Key Points:

• The core principle of addressing real customer needs remains unchanged, even as technology evolves.
• Embracing AI's capabilities while maintaining a relentless focus on desired outcomes ensures sustained business success.
• The rapid pace of AI development necessitates continuous learning and adaptability to leverage its full potential.

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Notable Quotes with Timestamps

• Matt Mazzie: "Any business you can flip the sales model on its head." [00:00]
• Ben Tossel: "AI can actually be the go to market." [03:00]
• Ben Tossel: "If you can do it for you, do it for them." [02:48]
• Matt Mazzie: "AI is not just a product. It can actually be the go to market." [03:00]
• Ben Tossel: "Build something people want... that's how you build most of these scaling businesses." [37:02]

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Conclusion

In this episode of My First Million, Matt Mazzie and Ben Tossel explore the transformative potential of AI in reshaping business models, particularly for agencies aiming to scale without expanding their workforce. Through personal anecdotes, strategic insights, and reflections on investment philosophies, the conversation underscores the critical role of AI in delivering personalized, scalable solutions and the importance of maintaining a customer-centric approach in an increasingly AI-driven landscape.

Transcript

[Matt Mazzie]

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

[Ben Tossel]

Absolutely.

[Matt Mazzie]

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.

[Ben Tossel]

Yes.

[Matt Mazzie]

You want to work with me.

[Ben Tossel]

That's right.

[Matt Mazzie]

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

[Ben Tossel]

Exactly right. I feel like I could rule the world. I know I could be what I want to. I put my all in it. Like, no days off on a road. Let's travel. Never looking back.

[Matt Mazzie]

I think about Matt Mazzie. I. I think about the word early. So, yeah, whether it was investing in companies early, you get, 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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 on the AI train. Like, you've been texting me photos of myself and my house, but redesigned using a, like, AI style agent. So can we talk about this?

[Ben Tossel]

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 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 the 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?

[Matt Mazzie]

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. These like an allergy test for fashion.

[Ben Tossel]

That's right. Perfect example. And, like, people spend, like, hundreds Thousands of dollars doing it. If you get a stylist in the U.S. 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.

[Matt Mazzie]

Right.

[Ben Tossel]

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.

[Matt Mazzie]

You know, I was going to say that.

[Ben Tossel]

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. Here, 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.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

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

[Ben Tossel]

That's what we're going to.

[Matt Mazzie]

Yeah.

[Ben Tossel]

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 end point of what you actually want.

[Matt Mazzie]

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?

[Ben Tossel]

Yeah.

[Matt Mazzie]

And that, like, do the work up front.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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

[Ben Tossel]

Absolutely.

[Matt Mazzie]

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.

[Ben Tossel]

Yes.

[Matt Mazzie]

You want to work with me.

[Ben Tossel]

That's right.

[Matt Mazzie]

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

[Ben Tossel]

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 birth. 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.

[Matt Mazzie]

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

[Ben Tossel]

That's right.

[Matt Mazzie]

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

[Ben Tossel]

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

[Matt Mazzie]

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

[Ben Tossel]

That's right. All of it was baked natively into the products. 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 autocorrect. 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 ch Chat GPT like you've, you were novel enough and early enough and powerful enough that you're now the dominant and default for the, for the category. But it didn't come with like new distribution for everybody yet. Right. Like there was the cheap jeep custom GPTs that was like trying to get there. There's MCP that's like trying to get. But nothing obvious. But what did change was it let you do the work in advance. The cost of work drop. The cost of work drops so dramatically that instead of selling the promise, you can just sell the finished work.

[Matt Mazzie]

Right.

[Ben Tossel]

And so if 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?

[Matt Mazzie]

Right.

[Ben Tossel]

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 to 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.

[Matt Mazzie]

Right.

[Ben Tossel]

The, the second order service can be the service that you actually end up selling. But you close them. You've got the opportunity to meet with them and close them on those other things because you gave them the value without ever having to.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

And then if you actually.

[Ben Tossel]

If I can do it for you every day. Do you want it every day?

[Matt Mazzie]

Yeah.

[Ben Tossel]

And you want me to keep track of things that are in. In style. Right. Do you want to personalize it over time?

[Matt Mazzie]

Right.

[Ben Tossel]

Like, those seem like. And then that's the.

[Matt Mazzie]

That's the upsell. But the kind of the. 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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. Social optimized video. And then I literally just email that person. Hey, Steve, saw you had that listing on 410 Montgomery Way.

[Ben Tossel]

Built you a real.

[Matt Mazzie]

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 a total engineer does versus what a sales guy does.

[Ben Tossel]

That's right.

[David Bonderman]

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[Matt Mazzie]

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. Because if you actually learn, like a differentiated scalable sales mechanic, it's like our friends who started doing Google Ads back in like, oh, five. 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.

[Ben Tossel]

Yeah, right.

[Matt Mazzie]

Or less than a $CPM. And it's like those are billion dollar secrets that like there's this arbitrage that can exist right now where there's new sales model, new distribution model that's less tap today. So what, what's a, what's an example where you could use this?

[Ben Tossel]

I think the beauty of like most enterprise software is like, you're, you're either helping to 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 two or three 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 list serve 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 H Vac 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 three 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.

[Matt Mazzie]

What, what do you think? So you, 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, the Mario. Mario Kart theory. What's, what does the Mario Kart theory mean?

[Ben Tossel]

Yeah, the Mario Kart theory is this is actually like, you could have made A lot of money investing in tech over the last handful of years, or at least in the SaaS.

[Matt Mazzie]

If you just followed this one.

[Ben Tossel]

If you just followed like, everything's better in multiplayer. Like, like build things that are like multiplayer by default. Big Mike, Figma, Notion, Airtable, Slack. Slack. Like take the communication tools or the, the enterprise tooling and like make it real time and, and, 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?

[Matt Mazzie]

In there? Yeah.

[Ben Tossel]

Why isn't it living with us in those social moments? Why do I never see your ex 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 three 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.

[Matt Mazzie]

Yeah.

[Ben Tossel]

And it was like a 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.

[Matt Mazzie]

Majority is a great example of bad is better because yeah, 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 a thousand channels, there's different numbers. Just hop into anyone and there's a flood of absolute random people generating absolute random images.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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 problem. We 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 mock up. 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

Outweighed all of the downsides totally. You know, that initial user experience and.

[Ben Tossel]

They could focus on just making the model better. They didn't have to focus on like front end resources and how to think about it. 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. 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.

[Matt Mazzie]

Because if I saw you actually, like, this would actually be kind of magical.

[Ben Tossel]

Right.

[Matt Mazzie]

Like, if I went in and 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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. 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.

[Ben Tossel]

Right. I designed your. I redesigned your house like from Zillow photos. I'm like, that's a probably better 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.

[David Bonderman]

Right.

[Ben Tossel]

Don't do any of that. Here's a. Do you like this room? I can do the rest of your rooms.

[Matt Mazzie]

Right.

[Ben Tossel]

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 illegal 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 two tool use spreading. Right. And it's like they put the ants, they put the stick in the tree, they get the ants out and another. But I was like, that looks like an ant lollipop. I like that.

[Matt Mazzie]

Right.

[Ben Tossel]

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. Nobody else gets it.

[Matt Mazzie]

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.

[Ben Tossel]

Social by default is always better.

[Matt Mazzie]

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, you know, I have a lot of friends. We're all looking at how we can use AI in our.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah. The workflows.

[Matt Mazzie]

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 tutorial. Whereas I really should just be able to fork that.

[Ben Tossel]

Yeah, right.

[Matt Mazzie]

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.

[Ben Tossel]

That people are doing. I mean like Zapier there's tons of like 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 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. Like makes a ton of sense. Like all the social apps, all the like iOS apps went social. It feels like collective, like forgetting. Right. And some, it does feel like a big market gap.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

First hand experience in doing so I run into the problems of doing that thing. Maybe it's like styling yourself or whatever it is.

[Ben Tossel]

Yeah.

[Matt Mazzie]

And then, and then learn by building.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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 you live in la. I just thought of you. I was like, this is like Hollywood pretty boy. And like actually you're more sure. Hacker ticker. Yeah. You focus on the pretty boy.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah. Yeah. So during COVID I. I have a buddy. Brian Wagner is like one of the best product guys I've ever met. I like back in the day he was building a company and 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 Road Trip, 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 five minutes in silent, two minutes of silence and it's like, I gotta 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 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're 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 code too. It's like if you ever see a company that is like an open source postgres like Firebase Alternative, like that's our ticket A week later by the way.

[Matt Mazzie]

From the outside it just seemed like solve problem. Firebase does this. It's probably fine, right? If you weren't building, you wouldn't know.

[Ben Tossel]

I would never have thought. I would never have thought. He's like, and we 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 and 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 replet competitor. But at the time there was like no development there. And so a couple 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 Tossel, who's like an incredible tinkerer builder investor out there, was an angel in the company, made the connection and we ended up leading the seed round at, at CO2 and did a. A series A there as well. And it's a great company. I love those founders and I, I think it'll be a great investment. But I never would have gotten close, I never would have thought about that idea if I hadn't experienced the pain first.

[Matt Mazzie]

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?

[Ben Tossel]

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. Okay, I got upset. So I'd spent a lot of time with the team at Bytedance and I.1 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 four years ago, five 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 a 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 going to 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, 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. 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 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 to. 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. It maybe it turns into an interesting business. And at the very least, you've, like, seen what the pain points there.

[Matt Mazzie]

Most VCs don't do this, do they?

[Ben Tossel]

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. I love that product. I. We were lucky enough to lead the series, being as a board member at Replit, and 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 technicallyish, 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 it 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.

[Matt Mazzie]

I like it.

[David Bonderman]

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[Matt Mazzie]

So what's their story with Replit and with Amjad? Because 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 investor in it. I hope it's 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.

[Ben Tossel]

There, the origin story, is amazing. I mean, what, what just stood out.

[Matt Mazzie]

To you from him or that?

[Ben Tossel]

I mean, just that he was always. 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 working in like PC bongs or whatever, like in his hometown and like to like just get access to the computer. It was like the same thing that like, you know, the when. When people were like spending time at like the research labs and 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 computer.

[Matt Mazzie]

As a kid in Jordan.

[Ben Tossel]

As a kid in Jordan. And then like, you know, and then he was obsessed with like spreading it to everybody. So he was like one of the first guys at what's it called, Code Academy in 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 end point. 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 waiting 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, 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 six months to validate the thing, but it really just gets you to the. The entrance of the maze, right? And it's like, now you've got to go through, like, what's up, idea guy? Welcome. Yeah, welcome.

[Matt Mazzie]

You ready?

[Ben Tossel]

Yeah. You up for this? Because the maze sucks, and you're gonna 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, like, the world telling you your idea is gar 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 guys 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's with the ideas fully. The MVP is 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.

[Matt Mazzie]

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

[Ben Tossel]

Oh, dude, the taste copers are even more.

[Matt Mazzie]

It's even. They're upstream of the idea guys. They're like, no, no, I don't even make the idea.

[Ben Tossel]

I just taste.

[Matt Mazzie]

I just judge the idea.

[Ben Tossel]

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

[Matt Mazzie]

Okay?

[Ben Tossel]

Do you understand this moment that happened a decade ago with Alpha? Everybody's like, best at go chess. 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.

[Matt Mazzie]

I remember hearing that.

[Ben Tossel]

Yeah, this is the quote. It's like, at least it all, you know, we're safe. And it's like, you know, at least it all 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 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 VCs safe, it's like, it's all about taste and psychology. All those people are going to experience, like, a taste moment where it's like, where they're going to be Lisa dolled and they're going to have a moment where it's like you're going to present their taste and the AI's haste to the end consumer. Because 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. 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 a McDonald's burger more than you're like, you know, St. Charles for 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 leased the 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.

[Matt Mazzie]

Well, dude, this just happened. Like, remember, I don't know, rewind five, seven years ago. And it was like self driving cars. What people working on.

[Ben Tossel]

Yeah. What's going to happen to the truck drivers?

[Matt Mazzie]

It was like the truck drivers and the grocery store checkout people. It was like, you know, we're just gonna have to find them new jobs. And then all of a sudden, like Dolly and these other tools came out. I was like, oh, it's actually us.

[Ben Tossel]

It's every.

[Matt Mazzie]

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 chat GPT.

[Ben Tossel]

Yeah.

[Matt Mazzie]

And like the modern wave of tools we're good at. It was like writing. They did like the fake podcast of Joe Rogan talking to Steve Jobs. And I was like, oh, podcaster, 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

But I definitely don't think it's the. 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

While you take one and it's just gonna play the like the law of large numbers and get it, get it right. Just by doing so many variations.

[Ben Tossel]

Like. Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

And so I'm like, sit down. I'm like, oh, shoot. Like, the idea was really great. I told like five people that do. They're like, that's incredible. This is great. You should do this. And then I sit down. I just actually have to do the work. I'm like, oh my God, this is so hard. How do I What. Where do I start?

[Ben Tossel]

Yeah.

[Matt Mazzie]

Are they in a cafe or they're a bar? Where do the characters, what do they say? And so I go to chat GPT 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 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 ego about it. Gives me another one, gives me another one, gives me another one. And eventually, like, it got pretty good at doing that scene and pretty good measured by your.

[Ben Tossel]

Your taste. My taste, as by your taste you enjoyed. Right.

[Matt Mazzie]

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.

[Ben Tossel]

Even lift a volume was there.

[Matt Mazzie]

The volume is going to win in a taste game 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, a thousand ads in a catalog, quantitatively testing which one gets the highest row, and they're doubling down on that.

[Ben Tossel]

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 bite dance and TikTok to like, 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, you know, I can't tell you how many mistakes I watched. That's so true.

[Matt Mazzie]

The Algo is literally the definition of taste, of taste. It's your taste, and it's already proven that the Algo dominates.

[Ben Tossel]

That's right.

[Matt Mazzie]

You know, whether it's editors inside the company or it's me for myself, it's better than. Than what I could do for myself even.

[Ben Tossel]

It's funny. And we make these mistakes all the time. I'm watching. I mean, you could argue that Apple lost the entire podcast business based on, like. Based on their. Their religion around taste. Like Apple. 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, 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.

[Matt Mazzie]

They, there was like the original originals, right?

[Ben Tossel]

The originals. It was like a 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 dollar channels and they gave a big budget and then they gave like $5 million for the native creators like Phil DeFranco and Michelle Fawn got like little touches of like cashier in 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 he 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 mod 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 taste makers so what do.

[Matt Mazzie]

You think it looks like? Let's say AI just keeps getting better.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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 gonna have, you know, so what happens? What happens to us? What, what do you do? How do you think about that?

[Ben Tossel]

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.

[Matt Mazzie]

Right.

[Ben Tossel]

And it's to me that's like, 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.

[Matt Mazzie]

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

[Ben Tossel]

Yeah, I've only, I've made, I made three investments post CO2 as an angel. All of them follow the same kind of framework. One of them is to a buddy of ours in the, in the travel space and the other two are founders that I back before. But all of them are basically agent platforms. 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 he's a genius.

[Matt Mazzie]

Correct.

[Ben Tossel]

Just 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 Deliver, which was like third party logistics for everyone. It was like Amazon prime for everybody. He worked at Amazon in fulfillment and then built Deliver, 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.

[Matt Mazzie]

What does that actually mean? So like they're building an agent that's going to be like, let's say your logistics.

[Ben Tossel]

Yeah, employee.

[Matt Mazzie]

But he himself is literally like kind of auditing the, like the answer.

[Ben Tossel]

He and the team that he is building are saying like, hey, we know exactly what goes into building world class fulfillment in logistics. We've done it at Amazon, we did it Deliver. Like I know all the details now. You've got a company that's an SMB, it's an E comm 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, 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 delivered.

[Matt Mazzie]

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. 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, 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.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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 the best teacher actually should have few billion students.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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 is the best at travel planning and booking? Who's the best at logistics, you know, workflows, planning and analysis?

[Ben Tossel]

Who's the best coding?

[Matt Mazzie]

Who's the best. Who's the best engineer? You know?

[Ben Tossel]

Right.

[Matt Mazzie]

It's actually not who's the best engineer. Engineer is who's the best engineer, period.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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.

[Ben Tossel]

This piece and do the digital work that they would have done for you. Right.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

That's amazing. I want to do some stories with you.

[Ben Tossel]

I have here. Oh, this is some pictures. These are scary.

[Matt Mazzie]

We're going to draw a card, and then I want. Is there people that you've encountered in your life? I want you to tell me some.

[Ben Tossel]

Stories or story time.

[Matt Mazzie]

Take a card. Yeah. And show the camera. Who'd you get?

[Ben Tossel]

I got Peter Thiel.

[Matt Mazzie]

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

[Ben Tossel]

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, you plan to lose in most cases. And I didn't, I didn't end up 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 pull out a W. And 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 trice. 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 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 genuine. 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 the. One of the best on, you know, investors of all time, or I can have Matt, and Matt loves me and, and, and that was his choice. And 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.

[Matt Mazzie]

Who you got?

[Ben Tossel]

David Bonderman.

[Matt Mazzie]

Okay, tell his story. Who's he and David Bond interaction.

[Ben Tossel]

David Bonderman passed recently. David Bonderman was the founder of tpg. David Bonderman was a guy I got to Know, later in life, he worked with a very close friend and mentor of mine named Rick S. And he was. During. During my sabbatical, one of the things that I did was like, I'm just gonna 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 short list. 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 huge investor in, like, the airline industry and, you know, had owned sports teams and was like a titan of industry and did it his way.

[Matt Mazzie]

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

[Ben Tossel]

Well, he worked for the Bass family, and he was like, he, like, helped build in, 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 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?

[Matt Mazzie]

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

[Ben Tossel]

I called Rick Hess, and Rick was building a. 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, like, 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 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 a hundred percent. And so I got to go and spend like a three hour session with Bondo and I was just like laying out where I saw AI going. I'm like showing him mid journey, I'm showing him like chatgpt, you know, and, and like just walking him through all the new products and, and he's just silently like kind of like riffing on it and like asking a couple questions here and there and, 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 friends who are smart and, 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 gotta 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 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 six 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. 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 the 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 a. Invest in trains and have it be like one of the most incredible business, you know, pieces of advice.

[Matt Mazzie]

All right, this episode is brought to you by Mercury. They are the finance platform of Choice for over 200,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of. And then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive. And you could tell that it's actually made by a startup founder. It's an entrepreneur. You could tell it's made by somebody who used other banking products in the past and didn't like all the different rough edges and annoyances and decided to, you know, actually fix it himself. And really any type of entrepreneur you are, let's say you're an agency. Well, one of the things every agency has to do is be able to send invoices easily, create them, send them to customers, and stay current on your balances with all your customers. Well, you can do that inside Mercury. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show. For more information, check out mercury.com Mercury is a financial technology company, not a bank. Check show notes for details. All right, we got three more.

[Ben Tossel]

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.

[Matt Mazzie]

What's an example?

[Ben Tossel]

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, 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 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 a fundraising. The handshake protocol. Like, we protocol the industry. And it's like, we're at, like, the furthest end. Maybe not the furthest end, but we're like the match the mature part of this industry. Like, when I got into it, there were, like, 10 seed funds in my 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 like the founder. You went to YC, there were 50 other people in the room. You kind of, like, you 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 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, CAH 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's 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 1811 VC, you had this boutique. You're like, I've got this board member that's my person. And then Adrian 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, 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, 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.

[Matt Mazzie]

Right.

[Ben Tossel]

You know, so I think what I took from that was like you can look at an, 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 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 are the startups really care about? It's like customers and attention, the scarce resources 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 capitalized.

[Matt Mazzie]

What's that guy's name? Jilly Something he invests in Whiz and like every security Sharpie. Basically he was like, he unbundled the Andreessa 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. You know, 500 companies and you'll get to 2 million in arrangement if you invest with us.

[Ben Tossel]

Yeah.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

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

[Ben Tossel]

Yeah.

[Matt Mazzie]

And like kind of create a little bribery network that like actually worked. And actually it's like turns out huge, huge results. Like you know, way outperforming results by figuring out that platform.

[Ben Tossel]

Yeah. And I think like those are like what he's continuing to do is find like what those gaps are, what the, 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.

[Matt Mazzie]

And part of what the startup founder wanted was like, you know, the brand a 16C.

[Ben Tossel]

I want.

[Matt Mazzie]

Cool. I want to be at the. I want Andrea Godala 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, what actually resonates most.

[Ben Tossel]

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

[Matt Mazzie]

Credibility.

[Ben Tossel]

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 billion, like how many trillions of dollars of Market Cap or like from those people were among the. You said you sell the association with Market Cap.

[Matt Mazzie]

All right.

[Ben Tossel]

Derek Cheater. 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. There's almost no equivalent though for sports stars because something embeds in your brain something 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, sports media company. And they're like, we want to spend time. And like I, 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. We go out to this nice restaurant in, 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 eight year old. And he's like, this is like the moment of his life. And so he's going, he's like, captures himself. Mr. Jita. Mr. Jita. 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. The guy recommends those, 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 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 he 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.

[Matt Mazzie]

I always have, like, a different level of cool.

[Ben Tossel]

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.

[Matt Mazzie]

Yeah, well, this might be the one that is.

[Ben Tossel]

That is. That is the one. I grew up as a. As the most die hard of die hard Lakers fans. I grew up in la. I went. I. I was a. I went to college during. During the Shaq Kobe years and the high school. In the Shaq Kobe years, high school, you know, Christmas was like Laker game 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. A Kobe Bryant partnership. And it was like, for a split.

[Matt Mazzie]

Second, how does that happen? Kobe reaches out.

[Ben Tossel]

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.

[Matt Mazzie]

Like, I'll get.

[Ben Tossel]

Do you want me to come now in the car. I'll come right now and we can do it. And 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 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, 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 three 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 adventure. Every blog post that I ever loved. Like, I'm going through all the girly posts, the Wilson post, and like all the, all the stuff and thinking that he would like never read it. 2am 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, when is this guy sleeping? It must be like going crazy because he was injured. He was like, just like texting. And then eventually he goes, I really want to go spend some time and meet. Like we'd suggested, 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. And we do like the tour of Twitter. And Twitter had just bought vine and we're like, walking around. We're onboarding him Divine and doing the Conversation with Dick and Adam, Dick Costello 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 there's Papa shot basketball. And the kid. Have you ever watched those people who are, like, savants and papa shot.

[Matt Mazzie]

Yes.

[Ben Tossel]

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.

[Matt Mazzie]

Yeah, they look like the Tesla humanoid.

[Ben Tossel]

Robot that's just like. Yeah. You're like, this guy. Is that to the T? And Kobe looks in and he's like, I gotta do it. And he walks up behind the guy and he goes, I got next. And all the engineers see, like, Dick and Adam, and they see Kobe and they're like, holy shit. Like, Jimmy's about to play Kobe. And they rush in. It's like vine has just come out. They're all, like, taking video of this thing. And, like, Kobe goes. He's like, bang, bang, bang, bang, bang. And hits, like, 80. And then, like, Jimmy goes. And it's like, bang, bang, bang. He hits, like, 82 and the Room, like, erupts. And it's like the greatest moment in this guy's life. He has never. It, like, it the whole, like. It's like, no one will ever believe this moment, right? He, like, I beat Kobe at Papa Shotty. That guy. And, like, you expect every. You expect Koe to be like, oh, congrats, dude. High five. And I just remember the look on Ko's face where he was, like, legitimately pissed. It was like. It wasn't like a fake P. It was like, I'm buying one of these things never happen.

[Matt Mazzie]

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

[Ben Tossel]

I'm never letting that happen again. And he, like, walks out, deletes his Twitter account. Yeah. Anyway, so it. I. It was. Was pretty incredible, like, getting to spend the time with him. And then, yeah, we. He was like, hey, I really want to build a shop. And so for a brief moment, we had, like, a side fund that we were putting together with Kobe, and we made, like, two investments. 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.

[Matt Mazzie]

This is amazing.

[Ben Tossel]

Super fun.

[Matt Mazzie]

Thanks.

[Ben Tossel]

Thank you, buddy. Doing it, I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off on a road, let's travel. Never looking back.

[David Bonderman]

All right, so when my employees join Hampton, we have them do a whole bunch of onboarding stuff. But the most important thing that they do is they go through this thing I made called Copy that. Copy that is a thing that I made that teaches people how to write better. And the reason this is important is because at work or even just in life, we communicate mostly via text. Right now, whether we're emailing, slacking, blogging, texting, whatever, most of the ways that we're communicating is by the written word. And so I made this thing called Copy that that's guaranteed to make you write better. You can check it out. Copy that dot com. I post every single person who leaves a review, whether it's good or bad. I post it on the website. And you're going to see a trend, which is that this is a very, very, very simple exercise. Something that's so simple that they laugh at. They think, how is this going to actually impact us and make us write better? But I promise you, it does. You got to try it at copythat. Com. I guarantee it's going to change the way you write again, copythat. Com.