New Media

“I think if you have a services company, they are one of the best opportunities out there right now. There are obviously people who are crushing it at local, like, strictly local media selling ads and stuff like that. I think it's harder, for a lot of reasons that we could get into, but the simple one is just like your market is capped, obviously. But if you have a services business, and this is the main way that the Austin Business Review has always monetized. I'll help founders with their newsletter.”

“So there's a woman here in town. Her name is Kirtana Reddy, and she writes a newsletter called Selling Austin, which is awesome. It's like a great weekly newsletter, pretty brief. There's, like, a handful of kinda market updates about what's going on in Austin, and then she'll feature a house or something like that. We haven't connected in a while, but at year one, I believe, she did something like $300,000 in what do you call it? Real estate fees? With clients who came to her via the newsletter. So the and that was with less than a thousand readers.”

“Anytime somebody starts to do relatively well in local, they always think about taking it to another city. And I think this is the challenge that a lot of the big companies have had, which is finding the talent to pull it off in the other city. Because the heart of a local newsletter is a connection to the local community. And so I don't believe that you can really write these from afar. And the challenge is if you can find somebody who can really write it locally, they could just do it themselves.”

“The only reason I started my local newsletters because the vision was I wanted to or I want to open a deli. And I was like, how does it how do you, on day one, get a line out the door? You have an audience. I think, so far, my plan is we're gonna do a pop up soon. I do think it's a real opportunity, and it is a real pathway. If you wanna start a restaurant or if you wanna start a brick and mortar, I think you can derisk it by building an audience first, and a local events newsletter is very easy to execute.”

“I think what's gonna happen now is that content will start to matter more than it ever has, and it may be a new way where because it's now being scanned by AI, not just humans. So Gmail or whoever isn't just saying, like, is this a good sender? Is the email passing authentication? Do people generally engage positively with their emails? Okay. Let's put it in the inbox. There's now this new curator in town who is AI, and they are looking at the content of the message and doing things with it.”

“Make sure what you're asking them to reply is quick and easy. So I've probably even suggested, hey. Ask someone to reply to your email. What's your biggest challenge right now? Which isn't a bad question, and you would probably get some interesting responses. But she had the good point that that's gonna take someone some time. They're gonna have to sit and think about that. A lot of people are not going to reply. But if you just say, reply hi, or, I'm curious. What email provider do you use? Reply one, if you use kit reply two, if you use Mailchimp, whatever people will just really quickly do that.”

“Google, Gmail, they have a tool called Google Postmaster Tools. It's free to use. You just enter your domain. You have to verify that you own the domain by adding a TXT record to your DNS. Once you've done that, it will start to populate with the data Gmail has about your domain reputation, your email sending. I'm helping thousands of email senders a day, sending billions of emails. It is the go to tool for me and my team to diagnose what's going on with someone's deliverability.”

“I don't think the word viral in podcast should really sit in the same sentence, like, most times. Obviously, there's clips that pop off and things of that nature. But, in my experience, that doesn't lead to, like, you know, you just being a continued success thereafter. You get that pop, you see it in the data, and then it kind of flatlines back to a a new baseline. Chris has been podcasting for, like, seven or eight years now, and it wasn't until year, like, five that things really started, like, you know, chugging along for him.”

“The single biggest test I ran that converted the best, and this might be unique to My First Million, is we ran a cross promotion with another show. The show that we did it with was just like this guy was a my first million die hard, and he happened to have, like, a really strong audience. He's in the personal finance space. And that single test that we ran was the most successful campaign we ran probably across the entire show. The reason was is, like, if you listen to the ad read, it was literally this guy saying, like, this is my favorite show in the world.”

“One thing that we've actually we're starting to do a lot more is just having a pre call with the guests themselves and trying to unearth what those moments would be. I learned this from Tim Ferris years ago. He had an interview with Edward Norton. And he started that interview with a question about, like, surfing. Tim Ferris describes this as basically, like, the bottom little footer of Wikipedia is where he found that. So try to find those, like, you know, nestled in Wikipedia moments that are very deep, but have potential for that person to get really animated and excited about.”

“We have, like, 12 core partners that we work with. Those core partners get a guaranteed number of impressions across the podcast and YouTube. And then with that, we basically include one to two newsletter features and then one to two Instagram story sequences. We could charge an extra 100,000 just for those things throughout the campaign, but we don't want it to come at the expense of okay. Now this brand's been an extra $250,000 with us and they're not seeing the ROI they want. We'd rather over perform for them.”

“There's a guy named Grant Owen. He's got a show that is relatively new. If you go to his Instagram, his first post is like a pinned post, and he lists out, my goals with the show. One of the bullets says, keep your head down for five years and then look up. So it's like, if you love this medium and you want to do it long term, you kinda have to have that insane mindset of, like, just fucking grind on it for five years, really go hard, and then assess, is this working?”

“Write, Grow, Sell has a 91 Net Promoter Score. And if you're not familiar with that term, it's a really high score, higher than Amazon, Netflix, Apple, Chick-fil-A. And Write, Grow, Sell is a program. It's a course, community, and a set of resources that helps you build a profitable and successful newsletter from scratch.”

“So we're building tools that you can add on to that. So that's Claude skills, which are incredibly powerful and easy to use, Claude project instructions and workflows, and then prompts that you can use across Claude or Shad GPT too. One of the challenges of the course is you sit down, and we have incredible curriculum that has changed the lives of hundreds of people, but you still got to watch it and do the work. And so we're flipping that on its head where you should learn from the curriculum, you should use all the resources inside, but even if you don't and you just use the AI tools that have been trained on hundreds of hours of our content, our curriculum, our podcast, my newsletter, you're going to get your investment back just through those AI tools.”

“Big fans of Claude. Yeah, it's just so much superior when you need it to actually write and sound human. So I think the big update is, number one, we're adding way more AI tools that do the work for you.”

“And one of my favorites that you added is that a lot of beginners when they start Write, Sell, they get hung up on is the name of their newsletter, especially if you're just starting out and we have a newsletter name generator now. So a lot of cool stuff in there.”

“And so the big reason we're doing this sale and we're reopening enrollment because I'm having a baby, May 5th. Me and my wife. Not just me. I shouldn't say hi. And you're having a baby. And we're having our second daughter. And I mean, frankly, we're offering this at the lowest price that it's been available since launch, since January 2024. Because of that, because I'm taking a couple of weeks off, because I want to continue to bring in cash for our team of 10 people at GrowLetter, invest in our annual conference.”

“And the final thing, another reason why it's a lower price than it has been before, it's literally $1,000 less than the last time we sold it, is because it's not going to be a live cohort this time. I may do this again in the future, and that will be a much higher price. But I want you to be able to work to the program on your schedule, not on my schedule, so when you join Write, Grow, Sell, you get access to everything instantly.”

“I sent out a properly copy written email where I was just like, hey. I have too much inventory on this thing. Last call to get it. No pictures. No nothing. One link. And that was my first $10,000 day that I ever did. I never made that much money in one day before outside of, like, Halloween or something. And I was like, woah. Something's up with this.”

“So in the past, I thought, man, if I could just make software and sell it, I would be the king of the world. And that was true ten years ago. It is not necessarily true. The moat of just having a piece of software is not really big anymore. So it's really hard to sell those small tools unless you're in a very niche industry or there's some extra rules around it.”

“I actually did. I rerecorded my whole course a long time ago because I used to use a lot of profanity and just weird examples, and I made a copywriting for business course. And I recorded the whole thing. I wore a suit and tie, and it flopped hard. And every business that is like, why don't you buy this version instead of the normal one? They're like, no. No. No. We want the stupid version because, like, that's what is is, like, fun.”

“We're gonna pay you I'm gonna make a $10,000 a month, right, for six months. And then what's gonna happen is, unless you hit certain goals by that sixth month, the seventh month, you only make what percentage of that goal you hit. So if you hit 1010% of your goal number, we'll pay you 10% of that $10,000. I think a lot of sponsors, what happens, they pull the plug, and then it severs the tie. So then I feel like, oh, they don't wanna work with me? Whereas this way, I'm still making money, but it goes down, and there's a natural conclusion to the sponsorship that feels very natural and not like they yank the cord.”

“I said, do you send out cold emails to drum up? You know, he's just like, I'd rather go to one conference and just host a private dinner with four people rather than sending out 10,000 emails. Because of those four people, something will come up two of them, and two of them may not do direct business of with us, but they might, like, intro us later or later in a career change have some sort of, like, you know, synergy, whatever. More business comes from all of those than all of their outreach combined.”

“Did you see, like, the, what the acquired podcast guys are selling podcast ads for? Over my Twitter 4,800,000 for a pre roll. Four episodes, twenty 20 nine season. Four episodes for mid roll ads is $4,700,000. I think they're selling out because this they're selling into 2028 and 2029.”

“I think if you're, like, an alien and you come and look at humans or how they're using their computers and stuff, like blogging people differentiate blogging and social media, and I'm like, I think social media is blogging. Right? So let's say Twitter or x, whatever, Instagram. I have a piece of content, a picture, a text update. I post it on this network. People read it and comment on it. That's blogging. It's the same thing.”

“Daniel O'Shea, the guy who is the director of x engineering team, he told me this. Everything I'm building has to be defensible by, like, ChatGPT seven. Right? So it used to be with ChatGPT sorry. Before ChatGPT, OpenAI, you had to give it long prompts. Everyone thought everyone's gonna be prompt engineers. I was telling people from the beginning. I'm like, the next model that come out, you will not need this prompt. It just gets that good.”

“Buy Then Build has sold about a quarter of a million copies, which puts it like, it's one of the best selling, business books in human history. Did you have any meaningful audience before the book launch? Zero, Matt. I had zero. In fact, like, one of the early reviews was, like, my I like it's a good book. My my only criticism is, like, who is this guy?”

“I knew that the ETA, Entrepreneurship Through Acquisition, club at Harvard Business School was putting together a conference. So I reached out to the MBA students, and I was like, hey. I just wrote a book on this subject, and look at Amazon. Look at all the reviews I'm getting. Would you mind if I sent free copies to all of your attendees? And they're like, no. That'd be amazing. I'm like, great. And I was like, all I ask is one thing. Just take a picture of the book there at Harvard.”

“Exceptional content is really a mix of a few things. Number one, strategy. Number two, tactics. Number three, a unique framework. And number four, a story or a case study. And that's it. If you can weave those four things together, you end up at, you know, Stanford Business School teaching classes. You end up with, you know, the single best course or curriculum out there.”

“Every book, falls. You launch, and your launch dictates as high as it's gonna get, and then they fall. And it either falls like a brick because it's a it's a terrible book. That's code for average. The average book sells 400 copies over its entire lifetime. Okay? Or it falls like a feather, Okay? Because it's great content.”

“Please, please, please, for the love of god, get yourself a whiteboard and put it in your workout room. Okay? And that's my setup. And so I get up in the morning. I'm usually thinking about whatever I'm thinking about, and then I start caffeinating. Right? So it's like coffee, exercise, and whiteboard, and what are you doing in between sets. I always try to work in shapes. So it's either some kind of Venn diagram or some kind of, you know, quadrant or some kind of triangle.”

“I sent out an email just to my list that was like, hey. All you guys are always asking me what I'm investing in. And here's my a team, and I've got more money invested with them than anyone else. And I invested $50,000 in this project, and I'm just inviting you along with me. I sent it. And I raised we we had we had room for $1,350,000, and I raised 4 and a half million dollars in four hours. That was the power of my email list.”

“Email has never been more important than it is right now. AI is gonna come in probably in the next twenty four months or whatever, and there's gonna be so much noise and so much nonsense. But if you can get in now and build your newsletter now and people will start reading it now, then they know when that newsletter comes in that that's the one I read. Right now is the time to be building your newsletter, and that's actually what I think has been the most impactful thing I've ever done.”

“We actually are the new family office is what I'm trying to explain. When you are a family office and you're investing and you walk in and say, I'm writing a $5,000,000 check, the thing is is you're not getting a 70/30 split with the sponsor like a like a guy writing a 50 or $100,000 check is getting. You're getting a 90/10 split, like a 20% gap. So I'll go in and get that 20% carried interest and effectively split it. So, like, our team gets 10%, and then all of our investors get 10%.”

“We, to this day, turned down we do not extend an invitation to enroll to 75% of people who apply. We don't let them in. Like, we are not in the we separate you from your from your money business. We are in the can you actually do this, and we have the highest acquisition to member ratio in the entire space. Hands down. Unparalleled results for people.”

“It's not just about the TBBN brand and the audience and that. It's about John and Jordy because they are gonna be reporting to the head of PR essentially at OpenAI, and they want them to do something beyond just the show to somehow help OpenAI with their public relations or communication strategy that's not just doing the podcast.”

“Sam Altman framed this thing as, like, a marketing problem. He said, these guys, John Geordi, are genius marketers. If AI were a political candidate, it would be one of the least popular in history. And given the amazing things AI can do, I think we need to be a lot better at marketing for AI.”

“Generally, in many cases, when you shut down their advertising business and they only run ads for the parent company, OpenAI, for example. They're immediately perceived as less independent. They're perceived as, like, shilling in many ways just for that one company. And it feels like a media business when you have different brand partners, different logos on your website and your podcast, it feels like a real, like, legit operation.”

“He said the main insight is the gap between full time and part time is insane. A ton of creators and almost no one is actually full time. Everybody has a company, a fund, a product, a course, something to pull them away from the main thing, the core thing. If you keep the core thing, the core thing, success will come.”

“I call this the land grab mindset. You want to like, when you're a niche media creator, let's say you own a category, HVAC. You wanna have, like, the HVAC newsletter, but then you also wanna have the HVAC podcast, and then you wanna be doing great clips, and then you wanna have the HVAC course and the HVAC coaching program, the HVAC conference, and they listen. Like, you wanna just land grab everything and just try and get everything in your space and have something to offer everybody, but that's actually is not what's gonna make you successful.”

“Another thing is live streaming. It's the next hot thing in b two b content. And what's so powerful about live streaming is it can be repurposed into literally every other media format, and nothing else can be said of that. So, obviously, you have the live stream, then that becomes a YouTube video in itself. It also becomes a long form podcast.”

“If that company actually ran independently, had their own business model, and only gave 50% of their inventory to the parent company, they could keep going sustainably for a long time without relying on additional funding from the the the ownership company. So I think and that's how you win media too. Like, the best media brands have been around for a hundred years or at least a decade.”

“Now OpenAI buys TBPN. So if you're building an audience and you have a valuable niche, you are a potential acquisition target. So start building towards that and think what would make you valuable to these larger players.”

“So, salary transparent, she started as a TikTok account, and you might have seen them if you're on social media where they go up and, like, interview people on the street and ask them how much money do you make. And they obviously think that The US go viral. It's, you know, been this, like, cult sensation. And I think most creators might just stop there. They say, I've got a million followers. I'm getting brand deals. I'm good. What else is even possible here? And, you know, from the early days, I felt like she and eventually had you know, has a little bit of a team behind her. It's built more intentionally as, like, how do we actually expand this as a business”

“And I think just this week, Plaid bought this week in fintech, which, again, is not a traditional, like, creator in terms of how it's more of a traditional newsletter brand. But, again, it proves that same model, as we've been seeing, like, works. And I think with with creators, we're we're seeing a lot of, like, investment in terms of, you know, people want, like, a face to the brand”

“And, like, even with me, like, I struggled for a while because I was like, I'm building my personal brand. It's under me. And I was like and I wrote from a newsletter. It was just my name. And I was like, no. I need an entity that feels like it could grow from beyond just me when eventually I will have two you know, not enough time to to build this out. And so I think that does derisk you in a way. So you build your personal brand, and then you say, I'm building this as a brand, as a business, as a community, what have you.”

“But I think for this creator model, the way that I think about it is, like, if at you're as a creator, you are almost like, a label of sorts. Right? You're attracting people that are interested in the things you have to say and your experiences, etcetera. And when you start to build this, like, audience or community, what people don't realize is that your audience is probably likely to get along really well.”

“Well, like, something cool like Jay Klaus is doing. So he's got his, you know, high ticket creator science community. And they're just pegging it to the conference, to the the kids' Craft and Commerce conference. So it's like, can you peg it to something that people are already traveling for? Like, I think there's ways you could get, you know, creative with it, basically.”

“I mean, I wouldn't say there's a typical number. I think you would be well, you wouldn't be surprised given the nature of what you what you do, but most people would be surprised at the amount of people that are running 7 figure businesses, and it's them a couple of, you know, maybe some contractors, maybe one employee, and, you know, some VAs and things. Like, I think that is really that lean creator business that is very, very successful.”

“My mom quit her job, in choosing tech sales, big tech career, and, bought a house in Italy, started documenting that. She found that a lot of, you know, people, her core audience were these, like, middle aged women that had the money to spend, like, a very valuable demographic, and they, like, love to travel, and wanted, like, experiences to go to. So she's like, let me start hosting some retreats. And some of them were, like, real estate focused in terms of people that wanted to to move abroad, and others were just, like, for fun. But that's been kind of, like, her surprise business model of sorts is she's got a she's got a paid Substack community. She's making money through her retreats”

“But I think the big the big opportunity here and I've been trying to do a lot of research around this in terms of how many creators out there actually, you know, have x amount of followers, have this money and they're not doing newsletter. And, like, there's a lot. There's a lot of people that are they're leaving it on the table, and and and what would that look like if if they kind of expand into their own audience?”