The Exchanges

Q listening to this is like, okay, great. The, you have all this amazing context because you have like a team of 55 people or whatever of some of the smartest people in AI and product. I don't have that context. So for people who, you know, don't have that context, but who want good You know, good outputs, be it product, be it whatever, how, how do they bootstrap context?

A The world is a large and lovely place, my friend. So we are not the only people who have produced beautiful work. I think for net new stuff, we're among the best in the world of thinking about AI flows, conversational UX, how to design for trust, especially with agents. Not a lot of people have done that. If you're looking back on this, this is go to Mobbin. Mobbin has an MCP now. Mobbin is a library of a bunch of beautiful apps, their flows, and all of the different permutations. Get Spotify's design system or another one that's similar, create a skill around it, plug into a mob and MCP and all of a sudden you can create this in minutes as well. So this is an only LCA stuff. Maybe the idea, okay, cool retention. You know, we had something called the daily five back in an early startup and maybe these ideas are easier to come by for us or faster to come by from us. And maybe our agents are more plugged into that, but in terms of producing something like this, People can do it just by using the right tools, and creating the right skills, and then slowly loading in the right context over time.

AI assessment note: “go to Mobbin. Mobbin has an MCP now... create a skill around it”

Q I mean, trust. I mean, I could listen to that and be like, yeah, like that's obvious. Like the more someone trusts me, the more likely they are to buy my services, uh, or join my team or, You know, do whatever I want them to do, but how do you go about actually building trust? And yeah, what have you learned about how you can do that efficiently?

A Yep. So I call it the three C's of trust, credibility, competency, and connection. Those are the three things that you're trying to get to as quickly as possible and in the most effective way that I've found. And I could be wrong and there's probably a fourth and a fifth and a 10th C, but for me, those three C's matter a lot. So right off the bat, I try and form some level of connection. Um, and that to me can be across a lot of different threads. Um, but give you an example in a sales call the other day is, Someone came in and they were building a sports media empire. And right away, I figured out what this person's favorite sport was, which happened to be basketball. I don't know if you guys know this or not, but I took a brief run at the NBA. It ended early when I was 15, but you know, I went for it. Um, and so right away, I was able to call back to some basketball talk that brought me back to my childhood and early days, and we just jammed on basketball for a while. And then we talked about the NBA for a while. And then we talked about sports in general and playing sports. And before even talking about what their goals were, their desired outcomes were, I wanted to as quickly as I could form a connection with this person that separated me from everyone else he was talking to. And so that was one way to kind of form the foundation for that, for that call. And I do this time …

AI assessment note: “I call it the three C's of trust, credibility, competency, and connection.”

Q It was, it was Ferrari money, you know, like it was, it was crazy, but would we do it again? I think so, but I'm curious your perspective. Why do we spend hundreds of thousands of dollars on retreats and bringing people together and That sort of thing.

A When we started late checkout, one of the things you told me was one, you wanted to build a forever place to work. And two, you just wanted to have fun. And I think like if you just get obsessive over the balance sheet on like every dollar being fully optimized, and I'm not saying this isn't a good use of money. I'll get to that in a second. But if you start to obsess over the balance sheet and every dollar going to direct high leverage activities like sales, like marketing, like fulfillment, like operations, and you divest in community and culture and fun. You might build a super successful business, but is it the one that you actually want to build and be a part of? And so I think when you said that, and we tell people that when they join, why are we doing it? One man, like just to connect and build some community. We are remote. We are alone in our homes and in our offices. You're out and about a little more, but a lot of these folks are just kind of hanging out and haven't ever even met the team. And so Let's get together. Let's put faces to names in the three D world and, uh, see how folks actually are and kind of stand next to one another, shake hands and have a good time. So that's one. Two is like, I think on the fun note, just have a good time and some spontaneity when you're together and you're just jamming, you know, usually you join a meeting. It has a start and an …

AI assessment note: “One man, like just to connect and build some community. We are remote.”

Q We do something that I don't know if many people do. We call it the nerd in residence. What is the nerd in residence? And why do you think it's a huge unlock to building products that people love?

A You came up with that term. I think I was calling it a contributor in residence. Lame was calling it creator in residence. Lame. Like you came back with nerd in residence. And again, in your marketing, the way you speak, I think that really hit the nail on the head. So nerd in residence. Is essentially someone who's focused on the new project, who's obsessed with it and is thinking about it all the time, loves what they do. And again, it doesn't feel like work to them because they absolutely love it. And so when you have someone like that on the team and not only on the team, but sometimes leading the project, we're stacking the deck in our favor to staff it properly, to get insights and intel to resonate with the community, which is really important to us. And then three, Not take a bunch of brain power and energy away from you or I, because we have someone in there thinking about it, feeding us information, and we are able to do what we do best to operate, market, grow, and give kind of strategic recommendations on where to take it. But the tactics and the obsession is done by the nerd.

AI assessment note: “nerd in residence. Is essentially someone who's focused on the new project, who's obsessed”

Q Knowing what you know now, well, you know, would you have quit? Would you have never started on that, on that, on dash?

A No, I think. Would have done it the same and wise. I mean, obviously like knowing what I know now, maybe we would have changed the schema a little bit or change the value proposition a little bit, but. I'm not, there's no regrets for what we did. We learned a ton. We got better at design as a result because we were reviewing, essentially we reviewed over a thousand plus design submissions in a matter of a couple of months. Had to grade all of them. Came up with a grading system. We just got a crazy good understanding of the talent pool out there and how to really evaluate great design. We sell design. We are world-class designers. It made us better. So even though, you know, we lost the battle, I think we won the war.

AI assessment note: “No, I think. Would have done it the same and wise.”

Q And just because you use ChatGPT does not make you an AI native company or an AI native person, right? That's like the The, the thing, you know, I speak to people and I'm, and they, they say they're AI native, and then I, I look into their workflows and it's, they're just using ChatGPT.

A I, I couldn't agree more. It's like if you had a website and called yourself like a tech company, it's just, the gap is massive. So you've good, it's good that you're using that stuff. Don't get me wrong, but we want to really build this moat. That's what an AI native org can actually unlock. Is this system, which is comprised of people, agents, and context. We'll get into each one of those. That produces incredible speed, where you can produce anything in minutes. I flashed a little teaser of that. We're going to do a couple of those. And then Signal, where you actually get to hear from the market often, really quickly, and then all of that feeds back into the system, and this gets smarter and better over time. Tracking so far.

AI assessment note: “I, I couldn't agree more. It's like if you had a website”

Q Theo, upon reflection, 20, 23, what else have you learned?

A I'm gonna build off this. You, uh, Jordan, you did a good job of building credibility and forming connection there. So way to steal my trust formula in gen in January before I knew it existed. Um, building off this, uh, and Jordan's gonna take on, you know, your agency and where you are today with late checkout is that everyone runs on batteries. So you have to figure out what charges and drains yours. Um, that Is I guess it wasn't a learning in 20, 23, but a real big reminder, um, that You know, people, projects, problems to solve, what you do outside of work, they all have an impact on your batteries and you have a finite number. And some people are running on a cyber truck battery and some people are running on double A's. So, you know, know how much you got in the tank, but at the end of the day, things drain and things charge your batteries and do more things that charge your batteries and way less that drain them. Yeah. Nice. I love that you still have double A's. Um, so I think like burnout occurs when your batteries get drained and it doesn't mean you've worked 60 hour weeks. It doesn't mean you are like burning the candle at both ends. It probably means you're just doing things that don't get you fired up. And, or with people who kind of grind your gears or taking energy away from you instead of building you up and charging your batteries. So, you know, we've worked wi…

AI assessment note: “everyone runs on batteries. So you have to figure out what charges and drains yours.”

Q Is there any, you want to give us a couple more?

A One that's maybe less applicable to work that I love is the dose makes the poison. I think this one to me is really all about balance and that everyone is unique. You know, Greg, you've been living up, living it up in Miami. You probably pretty, pretty good with the sun by now. I haven't seen the sun in six months. So like sunshine is good, but then it's bad. And I think for me, the dose makes the poison. If I'm out for 20 minutes, I'm going to burn to a crisp. You could probably hang all day in the sun. So That applies to many different things, and I think even, you know, you can think about it to your soft skills as well, or your hard skills as well, like patients. I have a lot of patients. The dose maybe is higher until it becomes poisonous. There's a, there's a threshold and an optimal dose, so to speak, and then you move into poison. Knowing when you hit poison on the things that you do and the things you embody, to me, is super critical and can really help you out. So that, that's one I also just love heaven is an, is a new pair of glasses. Like that's one of my favorite because it's just, it grounds you to perspective. When you're like, holy shit, the world's on fire. This person just led, this one's not showing up. They dropped the ball on that. Not that the team does this often, but you know, I'm being a little bit dramatic for, uh, for effect. If you just put on a new…

AI assessment note: “One that's maybe less applicable to work that I love is the dose makes the poison.”

Q Is there any, you want to give us a couple more?

A One that's maybe less applicable to work that I love is the dose makes the poison. I think this one to me is really all about balance and that everyone is unique. You know, Greg, you've been living up, living it up in Miami. You probably pretty, pretty good with the sun by now. I haven't seen the sun in six months. So like sunshine is good, but then it's bad. And I think for me, the dose makes the poison. If I'm out for 20 minutes, I'm going to burn to a crisp. You could probably hang all day in the sun. So That applies to many different things, and I think even, you know, you can think about it to your soft skills as well, or your hard skills as well, like patients. I have a lot of patients. The dose maybe is higher until it becomes poisonous. There's a, there's a threshold and an optimal dose, so to speak, and then you move into poison. Knowing when you hit poison on the things that you do and the things you embody, to me, is super critical and can really help you out. So that, that's one I also just love heaven is an, is a new pair of glasses. Like that's one of my favorite because it's just, it grounds you to perspective. When you're like, holy shit, the world's on fire. This person just led, this one's not showing up. They dropped the ball on that. Not that the team does this often, but you know, I'm being a little bit dramatic for, uh, for effect. If you just put on a new…

AI assessment note: “One that's maybe less applicable to work that I love is the dose makes the poison.”

Q a lot about building companies via the ACP framework, audience, community, product. And in an AI world where this exists, you know, your product, just like, you, you have this deep connection between the community and the product. Um, and You're just able to create a, a product that has a high, higher probability of success when you have something like this, right? Otherwise you're just kind of flying blind.

A Totally. And this, like the fidelity of the insights that you get again, that perfect, 20, 20 vision because of the context is awesome. So you can go to results and eventually you can see everyone here. This is a little custom thing that we built, but again, did it all with Claude. Wasn't that challenge. It's not like, you know, it was all elite engineers doing this. We were able to do it. And then you can have a report generated and when 50 people, 20 people, 10 people have kind of gone in and tested, you've got that. So I think a really cool opportunity. You can see the speed impact on speed. There's a little grid here. We don't have to talk about them all, but a proposal might've taken up to three days and now it takes minutes. You can saw that clickable prototype again, not a prototype in Figma, not a design prototype. If functional prototype could take one to two weeks to figure out what to build, do it, get it out in people's hands, took minutes, not only to get the prototype done, but also collect feedback and then potentially synthesize into the second version. So a lot of cool stuff. If we have five minutes, Greg, do you want to jam startup ideas, or are we out of time?

AI assessment note: “Totally. And this, like the fidelity of the insights that you get again”

Q Yeah. And how about we do one last idea from both of you?

A Okay. I'll make this one a quick one. Call it right hand. That's what, uh, this idea is called. Um, it's not fully fleshed out again. I'm gonna cop out a bit with the category, but, um, so 99.9% of businesses in the US are small businesses. 80% of those are businesses with zero employees. That means one person. So that's one set of stats. Another set of stats is Influencer, the industry, the valuation of the influencer industry has 11 X'd in the last seven years. You know, two million influencers today generate over a 100,000 dollars a year at least, and then there's like a top cohort that's generating well over 500 K. The problem, as we've mentioned earlier, is a lot of these single player businesses or kind of solo businesses, solopreneurships, a lot of these creators that are hitting at scale or starting to scale, sorry, you need a right hand. You can't keep doing it all alone. If you really do want to scale, there's two ways to scale a business technology and people and, or software and people, but I like technology as a better, um, as a better kind of bucket. And maybe I'm wrong. Maybe there's a third and a fourth, but those are the two that come to mind technology and people. And I was on a call with a creator today. He is going over the million follower mark, but more importantly, his reach is like, Very unevenly distributed. If you look at someone else with his follower…

AI assessment note: “Call it right hand. That's what, uh, this idea is called.”

Q on our door. I, a part of me is like, we should hire all these people and we'll figure out things to do. That's being aggressive. Conservative is being like, oh, you know, we're in the service. We have a ton of services business. It's like maintain, like, think about it as build profitable companies. And as profit grows, hire more people. How do you think about conservative versus aggressive?

A One, I think is the opportunity and how rare or how Common the opportunity is. So when we're looking at a hire, that's not a hell yes. That's not a, absolutely. We need to hire this role today and they're good, but there may be, again, everyone is unique. You're all snowflakes. Don't, don't worry about that. That's not what I'm saying. But if the expertise plus the uncertainty feels common, feels like we'll see it again. I think you lean into conservation or being more con more conservative. If it's a, like, how are we speaking to this person? Their skills, the fit, again, we optimize for fit, less about hard skills and soft skills and like where they went to school and where they worked, but more about fit with late checkout and how we roll. If the fit is like off the charts and they're going to be a level up to the entire team and they're in a function, isn't something super unique to one of our businesses only if all the stars are aligned. To me, it's like a conservative way to be aggressive. Like we have to jump on those opportunities and make Put our best foot forward or make our best offer. And so I think there's an opportunity factor that goes into it. Another one is just for us knowing what's going to be like a net positive and a net negative, uh, or a potential net negative. And I don't know if we always have the answer for that, but I think that boils down to, are we …

AI assessment note: “One, I think is the opportunity and how rare or how Common the opportunity is.”

Q And just because you use ChatGPT does not make you an AI native company or an AI native person, right? That's like the The, the thing, you know, I speak to people and I'm, and they, they say they're AI native, and then I, I look into their workflows and it's, they're just using ChatGPT.

A I, I couldn't agree more. It's like if you had a website and called yourself like a tech company, it's just, the gap is massive. So you've good, it's good that you're using that stuff. Don't get me wrong, but we want to really build this moat. That's what an AI native org can actually unlock. Is this system, which is comprised of people, agents, and context. We'll get into each one of those. That produces incredible speed, where you can produce anything in minutes. I flashed a little teaser of that. We're going to do a couple of those. And then Signal, where you actually get to hear from the market often, really quickly, and then all of that feeds back into the system, and this gets smarter and better over time. Tracking so far.

AI assessment note: “I, I couldn't agree more. It's like if you had a website”

Q conversation with more information around, okay, I was going to go build a startup, but now I'm going to build a studio or, hey, I'm like an executive at this company and I was going to go build this like one moonshot bet. I'm actually going to go build like a few of them. So walk us through one project that failed, how you knew and why did it fail?

A Sure. Um, I think a good one that I'll say is actually there were some indications of success and so even harder to walk away from, but It's a good example, nonetheless. And I think coming back to what you want to arm people with, the checklist we've created of what these businesses need to be really helps with understanding, should I go build a studio? Should I go build a single project or invest in a single product? And if I'm building the studio, what am I building? You have to hire an operator, i.e. if you're serious about it, you need someone to kind of lead. If there's no owner, nothing will get shipped. We want to make sure that it's a sustainable business in some way, shape, or form. So a path to revenue. Why now has to be strong. There has to be some kind of unfair advantage or reason why we might succeed. We've had, and you've had an insight around creators and audience being real jet fueled to early adoption, whether that be just to a newsletter at a content play or whether it be to a service. So those are a few criteria. One thing that we did try back to your question on what What studio project did we start, really kind of invest in, and then decide to pull the plug on? We called it Dash. You remember Dash, Greg? You were in those early calls, man. Jamming on Dash. The future, you know, was our oyster. We were excited. We were going to change the face of design and…

AI assessment note: “One thing that we did try back to your question... We called it Dash.”