The Exchanges

Q If you were, let's just say you were creating a digital product around how to sleep better, what are your next steps? Like, okay, you have the idea, and then, you know, how do you name it? How do you, you know, what, how do you generate traffic to it? Like, how do you think about growing a digital product like that?

A Okay, so if we're talking about something very simple, like creating an e-book to sleep better, I would definitely use a medium to share what I'm working on. So if it's, if I'm comfortable on the camera, I'll definitely go on YouTube or TikTok, Instagram. If I am better with writing because I'm a little bit introvert, then I will go on Twitter. And I would learn how to share my ideas, learn how to share what I'm currently working on so I can create content out of my daily life. And that would create, it wouldn't make a buzz at the beginning, but I would create an initial attraction. You would get five to like, I don't know, 10 people who just look at what you're doing and they will be here when you're launching. That's would be the first step.

AI assessment note: “I would definitely use a medium to share what I'm working on.”

Q lot of people are going to agree with you. They'll be, yeah, a format, but how do you, how do you develop your own format? You know, there's a lot of, There's a lot of content around developing your own voice, but developing your own voice is very different than developing a format that is going to work and, and get shared by people. How do you think about that?

A Man, those are good questions because I can really retrace the beginning of the journey. I'm like, Hey, I was actually thinking about that. Um, I think it comes to finding, consuming content, and picking the little things you like from each creator. For instance, I like the mindset of Peter Lovell to say, I did that, and having, like, lots of little projects. And I copied that, and I put it in my head, and I was like, now it's part of me. Um, maybe some of your audience know Justin Welch, a really good writer on Twitter. I like the way he writes. Like, it's very clear, concise, super simple to understand. I was like, okay, I love that. I took the way right, and I put it in my head. I'm like, now that's part of my identity. And I mix those creators in my head, and it becomes my identity. So my identity is not really my identity, actually. It's like a mix of lots of things I found everywhere, plus what I've discovered along the way. But at the beginning, there's literally nothing. And if you go back to my Twitter, you really see that things have changed a lot from the very beginning.

AI assessment note: “I think it comes to finding, consuming content, and picking the little things you like”

Q That's amazing. Okay. Um, moving on to your next idea and idea number two, what do you, what do you got?

A All right, if we step, um, all right, maybe we can move from that whatever course you're trying to sell. There's something I love, and it's maybe speaking to only gamers out there, but I'm a big fan of all the Farcraft. I've played games for so many years, and I try to gamify things that have a purpose in real life. So for instance, you could gamify your sleep. You could score points. You can compete with friends. You can lose money if you don't get good sleep, or if you don't track your habits or something like that. I think there's a lot to do in the gamification system because everybody wants better sleep. Everybody wants to eat better. Everybody wants to work out. And I think there is a game gamification things that could help people achieve their goals. And that could be a software by itself.

AI assessment note: “I try to gamify things that have a purpose in real life. So for instance”

Q What do you think you can charge for something like that?

A I would say this would be something you'd want to go more enterprisey for sure. Like starting at a thousand bucks a month, because anyone who has a small con, if you don't publish that much or have a big library, it's not that valuable because you can do it manually. You can just use spreadsheets and have a couple of staff members do it. That's what we're doing now. But let's say you have 25,000 posts. You're like Tom's guide or something. You it's And it's insane to even think of doing that manually, but you need to, to keep this stuff up to date. Cause it's about technology. So I would say you're starting at like 1005 1010 thousand, you know, that big enterprise contract level.

AI assessment note: “Like starting at a thousand bucks a month”

Q And if you were to start something like this, okay, so this is a great idea. I see the need. I actually, I would pay, pay definitely a few thousand dollars a month for something like this. Uh, how would you go about Like, actually starting this. Like, what do you do? Okay, what's next?

A The first thing I would build it for myself. So I'd be my own case study to start with. Um, and it's one of the, those business ideas are usually in my opinion, the best because you're, you're using it yourself. So you can see what needs to be added. What does it need to be done? Where does it mess up? Where is it good? Where is it bad? So first thing would definitely be building a beta that I test out on my own site or a different property that I own to get the nuts and bolts out. Um, and then from there, I'd probably do manual outreach and just be like, you have this massive library. I'm seeing a bunch of posts that haven't been updated in three years. We have software. I'll just go in, use AI, and give it some updates that it needs.

AI assessment note: “The first thing I would build it for myself. So I'd be my own case study”

Q I like it. You want to give us one last Brian idea?

A I need to, uh, uh, check my notes on that. Oh yeah, this is another, I think you might sip this one, as the kids say. Greg. So this is another, back to B to B. A content repurposing service. So this is another scratch my own itch thing. So if you work in content marketing and SEO for bigger brands, they always, even smaller brands, they have content that's just sitting around collecting dust that was published once. It's an email newsletter. It's a video. It was a webinar. It's an article. It's a tweet. And they never repurposed that content. And for me, that's the greatest opportunity with content marketing right now is repurposing rather than creating original stuff from scratch because it's cheaper and it has a proven track record already. So in my case, for example, with exploring topics, we have. All this blog content, and we're starting to repurpose it into videos on the, on a YouTube channel that we started. So it's so much easier to create those videos because we already have the building blocks of the article. We don't have to think and say, oh, what should we make a video about? Oh, what should it, you know, what should we start with? We go, okay, here are the biggest marketing trends. We have a blog post about marketing trends that was updated last week. Let's turn that into a video or the reverse. Let's take the video and turn it into a short, a bunch of shorts. And…

AI assessment note: “A content repurposing service. So this is another scratch my own itch thing.”

Q Yeah. So right book. I just pulled it up. Instantly publish your own books on the web for free. No publisher required. So this is basically, it looks like it's how do you make book publishing as easy as blogging?

A Yeah, exactly. Yeah. It's under the once brand here. Yeah. I like, I, I use hey.com, which is a product from the base camp guys. And I love all the simplicity that they've built into their products. And like, if anyone is going to attack that, that model, this, this doesn't seem to be tied into becoming a, you know, New York times bestselling author or getting published under a big brand. This seems to be a way to sort of instantly publish your own book, but I actually think that is just as good an idea as disrupting the traditional, you know, publishing model. Like this seems to be faster, better, easier, have less friction for those who want to get started. And like, do we see a major disruption? Do people in 10 years not publish with huge publishing houses anymore? Is everything done through something like a right book? And I don't know, there's a part of me that says that that's possible or likely.

AI assessment note: “Yeah, exactly. Yeah. It's under the once brand here.”

Q So you would, cause you have a, you have a SEO agency, right? Like, is this something you could offer? Like, would you like, why wouldn't you do it yourself for your own content for your own?

A So we actually have been building a suite of, we've been building a lot of this stuff. And so you're talking about boringmarketing.com. So we've been quietly just like building a lot of these, uh, tools. So this is the direction we're going in. So yes, I mean, I'm a believer, you know, I've, I'm invested in it. And the beauty about this is once you, once you capture an entrepreneur who's, who's like, who wants to build one of these ideas, they need more than just SEO. They need, uh, a bunch of different services and you can build the, and tools. They need a bunch of tools and they need a bunch of services. So, um, it's a super high valued potential customer and, um, That's the way to think about it, right? It's like, you, you want to think about how do I build a business with a high value customer? And this is like one, one great way to do it.

AI assessment note: “we actually have been building a suite of, we've been building a lot of this”

Q of programs for technical talent that exists training for technical talent, but there doesn't feel like there's that much in like the growth marketer content marketer space. Um, so are you saying like develop, like, you know, the programs around taking someone who's not a growth marketer To become a growth marketer and then connecting those growth marketers with, uh, people who want to hire them. Is that the idea?

A I am here to tell you that I love bootcamps. Like I think coding bootcamps have changed so many people's lives. Like I just, I think they are one of the best things that's happened in education in the last 10 years, but this flips it on its head. That's the, the code bootcamp route is take people, make them junior developers at a generalized big company. This is the opposite of that. It's take people, make them extremely senior Very fast, extremely specialized for a high paying, like extremely focused type of job. So growth marketer is one. Um, here's another type of job that you could do this sort of like K-pop factory for, which is a dev evangelist. When a startup needs their first dev evangelist, that person is like a superstar hire. I mean, like, like they have, they, they have star power, they're, they're building, they're great at speaking. Like that person is so hard to find. And the only people out there that you can see doing it are the ones who are already doing it. And you don't just need someone who can do it. You need someone who's going to be the first. And so like, instead of me as a founder, any founder out there, like, Hiring a recruiter trolling through LinkedIn and Twitter and trying to interview like hundreds of people for this one super specialized role. Why shouldn't there just be like the factory that turns out the best people at this low acceptance rate,…

AI assessment note: “This is the opposite of that. It's take people, make them extremely senior Very fast”

Q you don't think someone's listening to this, and they're like, well, easy for you, Jesse. You went to Wharton, and then you worked at Goldman. Like, what about the person who doesn't live in the United States, didn't go to the grade school, doesn't, you know, his friends are, his or her friends are just, you know, construction workers, or who knows, right? What do you say to those people?

A Well, again, I say two things. I think, well, one is depending on your age, it does matter where you go to college. And that's like a fun one on Twitter that I always throw at people because people love saying it doesn't. And I can tell you that the biggest meal ticket of my life was going to Wharton. Um, I went to a very average public high school. It was like middle-class immigrant parents. And man, that, that was a, I felt the step. Like I felt the step in my life and I have continued to feel it ever since. So that's one thing if you're 16 or whatever you are and you're wondering and you're reading this shit, like it matters. I think it matters. So that's number one. I think number two is, again, if you're a construction worker, like don't, why would you start a business selling to hedge funds? It just makes no sense. Like sell a business, start a business selling something to construction people, right? Like find the problems in the world you're in. Every business can make money. Like there's no business that doesn't, you know, it's not like selling to construction is better or worse than selling to hedge funds. It's, it's all just what you know. Um, and then the third thing is, I don't, I mean, I don't want to get too spiritual here, but I definitely believe the quote that once you put out into the universe what you're trying to get done, it conspires to help you create it…

AI assessment note: “find the problems in the world you're in. Every business can make money.”

Q It's iconic. But anyway, um, like I'm just imagining like that. That's something that I think when I, when I don't have to think about it, but I get the, the educational drip that I'm looking for. I think that's valuable to anybody, right? That's like competing at a high level. They want to know everything about everybody they're competing against or has competed in the same category before them.

A Yeah, and I also think that if it's, uh, influencer-based or creator-based, you just target people that, you know, if it's for me, let's say, yeah, people who follow me on, on X, just get those people. I'm sure you can get those emails for, like, pretty cheap. And then, and then just send them, like, I think they're, you know, businesses have levels, so, like, level one of this is just the free email with, like, Greg Eisenberg would recommend these two books this month, and here's some key insights from those books, and then, you know, the next level is join the book club, to your point. And it's like, you don't even have to, you know, for 99 dollars a month, we'll just send it to you right away. And then the next level is maybe a membership that, you know, uh, you know, synchronous events and digital stuff. That's the business.

AI assessment note: “businesses have levels, so, like, level one of this is just the free email”

Q Why? That, that business has generated, like, millions of dollars of profits for you. Why would you go and just decide, hey, it's no longer for me?

A Well, first of all, I'm very grateful for the revenue and profit it generates and I love the business and it is a big part of my life. Um, it's just sort of part of how my brain works. I would say like, sometimes I just hit a wall and get sick of something and I just want to move on to something new and interesting. Uh, I generally hold myself back from doing that and like stay on the core business. Uh, and, and the problem is sometimes it's also worked out really well. Like I remember a couple of years ago, uh, like seven or eight years ago, I was so sick of just focus or relying on client work to make money. And you maybe know the cashflow kind of variation when you're just doing client consulting work. And we started the education business with the in-person training and then online training. And that complete, like that moved our run, like burn rate from like three months to like, 15 months to 18 months. And I was like, holy shit, just being super annoyed at something sometimes generates interesting things. Um, yeah. I mean, what I often say is I'm not the right person to be the CEO because I'm the, the, I am the person when I get annoyed with something, even if it's making money, I'm like, I don't want to do this anymore. I don't want us to do this anymore.

AI assessment note: “sometimes I just hit a wall and get sick of something and I just want”

Q just have so much going on. There's just too much. I just want to get rid of it all and go Sell it and live in a cabin in the woods in Canada. So I guess my first question before I even ask any other questions, because I want to learn some shit from you here, is do you get to those phases where you're just done with it all?

A I don't. Like, I don't, yeah, I don't, I don't let it get to that point. You know, if I'm, if I'm ever, if I'm ever feeling like I'm overwhelmed, and too much stuff is going on, I just, I just take a step back. Like, instead of, you know, Here's one thing I'll say. I actually work every day. Like, seven days a week, I'm working some amount of time. And I know that's not what you're supposed to do, but I do it, because especially in the mornings for me, I notice that, like, I'm really, like, I get, like, one hour of work is, like, in the morning is, like, eight hours in the afternoon and night for me, so if I notice that I'm, like, getting close to being burnt out, like, maybe instead of working two hours, Every day, uh, or on a weekend type thing, I'll just, you know, I'll go to 30 minutes, so I'll just, or, or, or I'll go to zero, you know. Um, so I, I'm very conscious of, about the burnout, and I just don't get too close to the sun.

AI assessment note: “I don't. Like, I don't, yeah, I don't, I don't let it get to that point.”

Q All right. Well, what's on your mind? What's idea number one?

A Okay. So I guess idea number one is, goes to this, uh, crappy startup idea that every kid in college has coming out of college. They're like, and the first idea they come up with is what? It's an app to help you hang out with people when you're bored. And all of these apps have failed. Like all of them have failed. Like they just don't work. There's this negative selection bias where it's like the people who actually want to hang out are not the people you want to hang out with and like all of this stuff. But before we landed on the idea that I'm working on right now in stealth, we actually pursued something that is an iteration of this idea that it will actually work really, really well. Uh, and the idea is that instead of focusing on, uh, nerdy loners in big cities that want to hang out and weren't invited to parties as your target audience, you focus on, um, conference attendees, conference attendees. And the idea is that if you've ever been to a conference, whether it's like tech weeks and crypto conference, whatever it is, you know, most of the action is not actually the main conference events. All of the action is the side events. And actually maybe the more of the action is in the, like the, the private dinners and stuff like that, but really the side events are where the action is. That's where all the cool people are hanging out. That's, they're more interesting. Uh, t…

AI assessment note: “idea number one is... instead of focusing on nerdy loners... you focus on conference attendees”

Q so I think checkbox, checkbox, I think it could be really interesting if you did, Either a text or email, like, it's basically a newsletter, or, or just like a text every week. Like, every week we're gonna send you a text, and like, here's what you need to know, and, and I, you know, and, and just make it, like, remove the noise. Do you know what I mean?

A Yeah, I could totally see that, like, they text, and it's like, here's the specific things you want to focus on this week, and it's just done, and you could maybe even text them back to get more specific advice, like, I'm having issues with this, I'm having issues with my milk supply, I'm like, because there's so, like, I remember when I was postpartum, there was so many supplements I couldn't take, but then you can't just, like, call your doctor every single time, can I take this, can I take this, it's like having someone that you can just ask those questions to, I feel like people would pay so much money to have that solved for them.

AI assessment note: “Yeah, I could totally see that, like, they text, and it's like”

Q you actually grow something like this? So let's just say you wanted to build something like this. How do you, you know, you're, you know, you've built Instagram audiences with three, four or five million followers, you know, probably hundreds of millions of views at this point. Uh, you've probably, you've, you've done eight figures in revenue from those audiences. Like, would you do an audience first approach with this?

A I think if I was to do this, what I would do is put together, like, a very detailed package and a very detailed person, and I would just do direct reach out. Like, actually email the person something, like, very compelling, direct response, like, here's exactly what I'm gonna do for you, and just directly reach out to people, get them on calls, and sell them in. I would probably also do it for free to a bunch of influencers who have audiences of the women I'm going after. Like, looking for influencers who have audience of women who are pregnant or newly postpartum, and actually are looking to pay for a service like this, but when I started See Your Mama, which is a mastermind for seven to nine figure, um, mom entrepreneurs, this was my approach. I literally wrote down in my notes app all of the women that would be a dream to have in, and I just reached out to them one by one, And it was so easy. Like, they were like, this solves my problem. I sent like a seven minute loom video. They were like, this solves all my problems. Sign me up. So I feel like I'd probably just do more of a sales approach than an audience approach with this one and really get that product market fit. Cause I feel like people are going to come back and say, well, does it include this? Does it include this? I'm looking for this. And you can like tailor what you're offering, but I feel like you could get to …

AI assessment note: “I'd probably just do more of a sales approach than an audience approach with this”

Q thing that people don't talk about, which is, you know, if you're able to generate customers, uh, for a startup, people are willing to basically share in the revenues, you know, it's a revenue split basically, you know, so I think that what sort of prompt could you give to people in terms of, You know, how do you come up with an idea for, you know, in the space?

A I think the best way to come up with the idea is to start with how would you sell it? So basically, uh, don't build stuff, but just see what people are actually looking for. And for example, like I give precise examples from, from my own journey. Like I saw a lot of people asking about SEO, for example, like people were asking how to get backlinks, how to grow, how to, you know, uh, Grow the demand rating, et cetera. So when you see those requests, usually you see people answering how to do it with like seven steps. And some makers kind of like that, just, you know, they read the steps and they implement. But, uh, since most makers now are actually busy, like they have even full-time job or, or their side project say that they want to save time. And then if you rub that little kind of list of actions into a tool, I call that micro SAS, uh, and it, Just does one thing, uh, but it doesn't clear. It's clear what to expect and it's easy to recommend. So like my, my game plan is this, like I want people to recommend my tool under those posts. Like if somebody asks like how to do X and then somebody comes there and says, I did that using this tool. And if tool just only does one thing, then it's easy for the user to remember This tool, and to recommend that tool, comparing to the tools doing, like, a lot of things, like, then it's hard to remember exactly what it does.

AI assessment note: “the best way to come up with the idea is to start with how would you sell it”

Q So what I love about you is you hijack, you hijack the narrative, and you do it through art, and That's the lens of our conversation today. Uh, you've got a few cool ideas. I just want to jam with you. Um, where should we start?

A Well, the reason I hijacked the narrative is I started in advertising technology back in like, 2008, nine, 10, when Facebook's API was emerging and YouTube and the iPhone were emerging and realized that there were these new centers of attention. And there were certain metrics or places that you, metrics you can manipulate or places you needed to be seen, uh, in order to capitalize on those, those attention portals or places for attention. And, um, that's where I really honed my skills that I'm now kind of playing out in art. Um, most of my art to date has been me starting with a headline, thinking to myself, like, what headline could I make? And then reverse engineering actually, actually how to do it. Which publication to pitch it to? How to create enough digital artifacts to tell the story? Um, I've shied away from that, and I would say, like, in 2020, when the pandemic hit, I was looking at you and Jack Butcher leading these digital communities, and realized that was definitely the future. Um, so I, I would say that you guys were a big inspiration for that, um, and started an art community, and then realized there was all these ancillary businesses In addition to being a direct consumer artist or a gallery artist, um, that were fascinating, that supported the entire ecosystem and community, and that not a lot of entrepreneurs were building. And so I think that's where we're …

AI assessment note: “so I think that's where we're going to start”

Q to, the way to think about it, I think, is start with a business that You know, produces cash and, you know, is profitable, and then acquire, and that's, that's also the HubSpot model too, right? Like, HubSpot created the CRM, high margins, and then they started acquiring media after they figured out that, okay, we've got this great margin business, let's go spend twenty million bucks on the hustle.

A Totally. Totally. I think that this is the bigger trend that's happening in all business is, do you know, aero electronics? I think we talked about them last time. Um, six billion dollar market cap. Like they've basically been rolling up like Electronic components at magazines and blogs and like, you know, any like industry publications for the last 60 years. That's their whole strategy, right? They're just a content machine and they're selling a commodity products. That's the only way that they can do this. And I think that this is going to become the standard. Like I, this is how I think about owned media, right? It's like, it's this long-term investment that can never be taken away from you. And like, as this thing grows and if it lives on long enough, like the cost Like the upfront cost of starting that thing approaches zero over time, right? So it's like an infinitely decreasing curve because you're just like amortizing it over like as many, as long as the existence of the company happens. I think the other piece too that people don't realize is that it's marketing leverage. Like why does a HubSpot or any of these other companies like, you know, and this is something that I learned when I was at Rupa Health, like we saw that we grew this podcast that became like known within the industry. And companies that previously would not even take a call with us were inbounding bein…

AI assessment note: “Totally. Totally. I think that this is the bigger trend that's happening in all business”

Q going to be one newsletter in a topic, right? Like you go leave and start your own thing. Uh, so I think you have a lot of opportunities and obviously find the right person to work with, but I don't know. I feel like there's something cool there. What do you think? I feel like you would say, no, go start your own thing. Don't go work for someone else.

A I, I would say both. Like, go work for someone, because you can do things at scale, and test at scale, and there's, especially in social, specifically, social and product, you know, when you, when you launch a new feature to millions of people, or hundreds of thousands of people, you really pay attention to what that product is, and if it's dialed, versus you're just putting it To potentially no one or same with social, like you're tweeting to a million people versus just tweeting to a hundred people. Like you really, you really instinctively over time learn about how to connect with people and you can take that in the future and apply that to your own products. So I would say go work for someone, but at the same time, go also be testing what you're learning on the side.

AI assessment note: “I, I would say both. Like, go work for someone, because you can do things at scale”

Q around DeFi and stuff like that. But yeah, I think there's a lot of opportunities, but then at the same time, I'm like seeing all these like meme coin stuff and it like, to me, it takes away from the industry to take it seriously. So I'm curious, what are your thoughts on meme coins in general? And like, do you consider meme coins of, you know, a venture opportunity?

A Yeah, I'm here, here, I'll give you the, I'll give you both sides of the argument, I think. Here's the meme coin suck argument. Meme coin suck because there's all this attention on crypto now that Bitcoin just broke through its all time high. People are looking back at, at crypto at, you know, there's the Bitcoin halving this week. BlackRock and Fidelity have their Bitcoin ETFs. Like the space is clearly coming back and we're entering another bull market. So all these eyes are on crypto and all we see are these stupid meme coins. That's the, And it's like, guys, like, come like you're doing what we thought you kids would do playing in your stupid little crypto sandbox. You're creating these stupid meme coins. That's the, that's the, that's the meme coins are stupid argument. The meme coins are good argument is just that, um, marketing is harder than ever in today's world. Like finding attention on the internet is nearly impossible today. You can get these quick little hits, maybe a viral tweet or something. If you're, if you're Greg and you know how to tweet, but like for most people, marketing is impossible. And what you're about to see are a lot of meme coins actually turn into real businesses. So you're going to see like the way I think about meme coins right now is there's like the meme coins that you can just kind of speculate on whatever. Everyone's going to have fun with…

AI assessment note: “you're about to see are a lot of meme coins actually turn into real businesses”

Q That'd be cool. That'd be cool. Um, what else you got for me?

A What else we got? Um, swag up for premium blanks. Like, basically, I've been trying to, for my little brand do within, make a couple sample hats. And I'm just frustrated with the whole process of making a hat that is not just a print on demand or embroidery on demand type of thing. But I also don't want to start a hat company and like, don't want to be in like a direct to consumer merch situation. And we think about this a lot with late checkout too. And how can we have high quality products that we can give our customers, team members, you know, future partners, And I think there's a big opportunity for a brand in a box for gear that feels really cut and so high quality, but isn't a print on demand type, you know, churn and burn system. So I think you layer on three PL like and fulfillment on the back end of that warehousing, et cetera. And you can basically build like a marketplace. If you have the, Um, the suppliers and the production, you could facilitate these, like, brand in a box experiences for companies that are not traditionally doing things like IRL or with physical products. So I saw Notion a couple weeks ago launch these, like, really beautiful chore jackets, and it just had, like, the little Notion icon. And I don't like using notion, but I would wear the mess out of that thing. It was so cool. And the photo shoot was amazing. And I think there's just these intern…

AI assessment note: “swag up for premium blanks. Like, basically, I've been trying to”

Q And, and just curious, like, why wouldn't you, why wouldn't you build this?

A Oh man. I, I think that there's one of those things where if, if you're a builder and you go off and you spread yourself too thin and, and you're trying to do too many things, you just, you go an inch deep on everything and you just really don't do it. The product justice, right? Like you don't, you don't spend the time and I I'd have to really, Put together a team to go build this and, and, and be heavily involved in the early days. And, you know, I just recently sold my last startup and, and kind of exited out of web three, which was, which is its own madness. And honestly, I really enjoy, um, just Talking through and working with some of like, you know, leading experts in different fields and, and, and doing that on a podcast format. It's like, it's really a lot of fun for me to have these great guests on my show. So I think podcasting is kind of my, my next chapter for, for at least for a while. I need to take a break from startup world.

AI assessment note: “I think podcasting is kind of my, my next chapter for, for at least”

Q So what's the story? He, cause you know, what's the story with him? I know he, he grew up in, or he was living in Key West. I think he was like poor, you know, playing on the streets. Well, you know, how did he go from, you know, playing the streets of Key West to being a multi-billionaire, owning a bunch of companies?

A Yeah. So he actually tried to get into, he wanted to be a musician. He knew that about himself and he tried to get in to, um, the music industry, uh, through the front door. So he went to Nashville and he tried to get a recording, uh, deal and he would come in and the record labels would be like, we don't know how to classify you, right? Like you're not, you're not country music. You're not rock music. So he tried, he, he got a couple of records out, I think the traditional way and they, Utterly failed. Um, and he actually picked up and went to kind of green pasture Key West at the time, uh, which when he went there was like a shell of what it is today. Like rent was super cheap and he was actually, uh, going from bar to bar saying to them, uh, I'll, I'll, I'll play here for, for tips and booze. And that was his fee, uh, if you will. And he basically was super scrappy and lived off of Uh, of tips and slept where he could, uh, in the beginning, but he went, uh, he, he slowly started to develop, uh, a name, uh, for himself. And he actually, uh, you know, he was playing so often that his style started to become, uh, more formalized. And since he was leaving, living in, uh, Key West, he started to make that a part of his persona and a part of his, uh, of his music. And, um, he just, Worked his tail off going from venue to venue, uh, around key West. And then he started to expand an…

AI assessment note: “he slowly started to develop, uh, a name, uh, for himself.”

Q to B media podcast, uh, that podcast actually went a little bit viral. If you haven't listened to it, um, go and check it out on the channel. But, you know, do you have any, do you have any thoughts on, you know, categories that make sense? Um, and how you, how do you think about B to B versus, you know, your classic B to C funny meme account?

A Yeah, you're asking obviously excellent questions because it has to be in categories that you could monetize them in some way. So having a bunch of, you know, prank channels, uh, get together isn't gonna be, isn't gonna be great. Uh, but you could certainly focus on, um, like one category that I love consuming content on is like the building category. So I love watching YouTube videos that are people constructing houses or doing home repairs or doing a product reviews of, uh, Of tools and services. That could be a very, a very lucrative field to enter because there's a bunch of ways you could monetize that on the back end. I'm also in the finance world. So that's the one that I know best. And obviously there's lots of ways to, to monetize people that are interested in stocks or investing or, or real estate through, through brokerages. Uh, that you could, uh, you, you could partner with, or there's tools out there that you could sell to people that have interest in that. So those would be the two that come to mind, but I'm sure there's lots of categories that you could apply it to.

AI assessment note: “one category that I love consuming content on is like the building category”

Q They've been split testing this and doing all kinds of optimization of this over the course of years. So if they are sending four emails per day, after you give an email to them, that, that isn't by accident, right? That, that was all pre thought about and tested. So their data clearly showed that sending lots of emails to really get people to convert is the way to go.

A Yeah. So you bring up a good point. Something I've been thinking a lot about, which is, you know, recently a lot of, uh, a lot of founders that we know are obsessed with conversion rate optimization. So how do I get, you know, as much juice out of this lemon as possible? And I get it, right? If you're converting at eight percent and then you get that up to 12%, that could be the difference. That could be, that could, you know, like be hundreds of thousands of dollars, not millions of dollars, Uh, of profit for your business that year. So like it may, you know, I get why people optimize for conversion rate, but I think that people are making a mistake by just optimizing for conversion because it's not really long-term thinking. Um, you know, long-term, and this is like a half-baked thought. So workshop with this workshop, but with me, but it's this idea that like, yes, I could send four emails a day and I'll probably increase sales and. You know, that's great. But think about those people who unsubscribed and who are now going to tell their friends, oh, you know, or, or they're at a dinner table and someone brings up the Motley Fool and they're like, oh, I got so many annoying, annoying emails from them. I had to unsubscribe. So I think that there is a balance between conversion rate optimization and, um, no optimization. And I actually call it community rate optimization, CRO. …

AI assessment note: “I think that people are making a mistake by just optimizing for conversion”

Q Let's dive into affordable housing. I'm like selling my Apartment right now. So it's sort of top of mind. Um, I saw that Joe Gabbia, the co-founder of Airbnb is building. He raised like, I think like. Fifty million bucks or something to build. 40 or fifty million bucks to build these, a startup around small prefab houses. What's your thought on the whole prefab housing opportunity?

A We're looking for a company that doesn't use a ton of money to figure out how to make it work. And, you know, the problem with a lot of these businesses is you're taking a really big bet that prefab housing is going to be the future. They raise a ton of money and they consume a lot of capital, but we haven't really seen any of them kind of go through that J curve and get out of it. And we're looking for a more capital efficient way to approach the space. You know, from a financing perspective, it's sort of a weird credit problem. Because let's imagine I wanted to fund construction. I could fund regular way construction, like general contractors. Um, and you know, that seems like it might be risky because have you ever heard of anybody having a good experience with their contractor and feeling like they didn't go over budget and pass time and get the permits done on time and all that stuff. Like I haven't. Um, and so the prefab homes might be easier because they're sort of copy and paste. The problem though, is like your severity of loss on a prefab home is quite high. So let's imagine, you know, I don't, I don't know Joe Gabbia, but let's imagine he came to us and he said, Hey guys, like, you know, I agree with you. Starting these companies is incredibly capital intensive. It's really difficult to get a venture outcome if I'm going to have to raise hundreds and hundreds of mill…

AI assessment note: “the problem with a lot of these businesses is you're taking a really big bet”

Q I appreciate it. So on this podcast, we talk about different business ideas, um, and, and different niches and trends. You prepared a few, which I think are, are fascinating. Um, and I want to start with suffering as a service. What do you mean by that?

A Yeah. It's funny. Cause it's almost like SAS, right? It's like the same type of acronym. I just think normal life has gotten so soft and easy, you know, Uber eats to your apartment, go puff for deliveries. Um, and that's why you see all these people doing, you know, tough modders, Spartan races, ultra marathons. People are craving that type of discomfort. It actually makes them feel alive. Um, even like these dark retreats, like in the last year, I don't know about you, but like five people I know are like, oh yeah, I just sat in darkness for a week. To like find myself and like, you can position that however you want. That is suffering, like in some way. And it's like, I think you can get really creative with that. And I think it's a massive opportunity. Like you do have to imagine just normal life is just going to get easier and easier, right? We're going to have to do less and less. So people will need more things like that. And so like, honestly, it's a big part of what I'm doing. Like this run cult, I just started this run club. It's kind of like shared suffering. And I think that's why people like it.

AI assessment note: “People are craving that type of discomfort. It actually makes them feel alive.”

Q Yeah. Awareness and affinity. That's what, that's how I describe it. Shoreform is great for awareness and affinity is, uh, Is what you call it?

A Like the connection and, and yeah, like an analogy I used the other week, sorry to interrupt you, is like short form is like, short form is like passing someone on the street. Maybe say hi for a second, but it's a short interaction. And long form is like sitting down with them for dinner. It's like, oh, you're really getting to know them now. Um, Dylan, Dylan even had a better analogy with that. He's like Dylan Jordan. He's like, yeah, short form is, you know, on the street, you don't choose it. It just happens to you kind of like short form scrolling on a feed, but long form, you're choosing to meet someone you're clicking on a video. It's totally different.

AI assessment note: “short form is like passing someone on the street... long form is like sitting down”

Q I have a newsletter. I could easily Do podcasts, short form, long form, you know, long form, like a bunch of other platforms, you know, TikTok, Instagram, shorts at the same time. And it took some awareness to basically be like, no, like that, that's actually a bad idea. Like go what? Like, and I love that flexible with the format. Is that what you said? Flexible with the format?

A Well, yeah, that that's what I did last year to make it super tactical. Last year, I didn't have those videos, right? The animated videos that got hundreds of millions of views, and I didn't have obsession as a brand. So at the same time, I basically was like, all right, I'm going to commit to this one message, but I'm going to be super flexible with the medium that I use to get the message in front of more people. And that is like a thing that I don't think anyone does. And, and if you, most people don't do either, but when you do both, what it got me is a ton of new, new fans and a ton of actual true fans who will, you know, put obsession in their bio and come to my run cult. It's like, that's like one of my favorite ideas I've came up with that, like strict with the message, flexible with the medium.

AI assessment note: “Well, yeah, that that's what I did last year to make it super tactical.”