[on-hold music] Welcome to the Rebooting Show. I am Brian Morrissey.
I'm gonna kick off this miniseries that I wanna talk with a lot of independent publishers, because there's a lot of doom and gloom out there with publishing, and there's a, a really vibrant area for a lot of particularly niched media businesses that are being created.
And I wanna highlight one today, literally one of my favorites. It is Mostly Metrics. CJ Gustafson is the man behind Mostly Metric- Metrics, and the reason I like it is because CJ is a practitioner.
Mostly Metrics is focused basically on finance professionals, people who are CFOs, but more importantly, I think people who wanna be CFOs. We can get into that, like there's always an aspiration.
There's only cer- so many CFOs out there. But like anyone, I think, who touches finance ultimately wants to be a CFO, so you wanna be that. CJ's got over a decade of experience in, in PE, M&A, and finance for startups.
He started writing a newsletter in late twenty-twenty, like many of us, during the newsletter boom, and he has grown Mostly Metrics initially on Substack. I think he, he switched to our friends at Beehiiv. Nice move, CJ.
And it was a subscription business, and I know we started talking, like when you were doing subscriptions. And I'm not taking credit at all, CJ, I just wanna say. But I was like, "You're sitting..."
I was like, "CFOs literally make every spending decision. They are the most valuable people to be reaching," and I am really jealous that sometimes I love my media people. I kinda wish I had...
I think I kinda wish my, my audience was your audience sometimes, CJ. I have a question before we go too far. Is it, is it too late for, for me to be anonymous CFO, or do people already know who I am?
[chuckles] Uh, you can be. I mean, our anonymous, anonymous banker is li- is, is only lightly anonymous. I'm just kidding. Most people, most people know it's Blake. I'm a fan of the show, obviously. You can tell.
[chuckles] Awesome. Well, let's, let, let us get into it. So you started writing this newsletter in December twenty-twenty. You were scratching an itch there. You know, it's a typical pandemic story, right?
You're like exiled, I think at the time maybe in Cape Cod, but we started talking when you were in Florida. But, you know, you started writing it and it gained traction and eventually became a business. Yeah.
And a lot of people think that it became a business overnight, but I was screaming into the void for- Yeah... a very long time. So it was, it was like over two years of just four hundred subscribers.
And for context now, you know, we're talking at the tail end of twenty-twenty-five. I'm at seventy-one thousand subscribers in the flagship publication.
But, like, going from just writing online to what I call finding your audience market fit to then finding your monetization model fit of how to gear it towards a business model, all of that took some time. Yeah.
And like we, we had talked earlier. We did a- Yeah... podcast earlier on this. And, you know, I think the...
What's unique about you, like I do think like there's similarities between you and like Lenny Rachitsky to s- to a degree, right? Like I don't know d- if you accept or reject this- Oh, yeah... but he's got a- Yeah...
great business, so I would accept it, CJ. But like I do think there is, because you're, you're focused on a specific area and you bring not like a capital J journalist perspective. This isn't like CFO Magazine, right?
Like you- No... bring practical, real world experience. You know, annual planning like is something that you have done, right? Yeah. You're not like going out necessarily. I mean, you'll do that.
You'll talk to, to fellow CFOs, right? But like you have lived experience. Yeah.
I'm a practitioner of the craft that I write about, and my whole background is helping companies budget their resources to, to get the most money out of it, right?
So I'm, I'm kind of a business person first and foremost, and along the way I picked up all these playbooks on how to budget for your business, how to figure out how many sales reps you have to hire, what metrics you should use to gauge success.
And I was scratching my own itch because I enjoyed writing, but I also wanted to make sure I didn't forget it, because I knew to get to the next stage, and I eventually did become a, a CFO at a venture-backed company.
I needed to have like these playbooks and I was just d- writing it down online rather than, I guess, writing it down like in a diary somewhere. Yeah.
And this was a g- initially when you started to get traction, it was a classic Substack, right? Like it- It was. I started on Substack and I waited until I was at ten thousand free subscribers to turn paid on.
And I'd confided to you a while back when I was still figuring it out like, "Hey man, this, this paid thing is a slog. These people are pretty fickle."
And what I realized is that was very much a B2C motion, and I definitely wasn't optimizing for the lifetime value of a reader.
And there are different ways that you can monetize the readers or the, I guess, the participants in your ecosystem, and I found out pretty quickly that while paid has some, some, some glitz and glamour to it, because a lot of people do put it on their corporate credit card under a learning and development budget, like the stuff I'm writing about is business related.
It's not the best way for me to monetize my audience long term. Yeah. So talk me through that from like a CFO lens, right? 'Cause I mean, you mentioned LTV and, you know, I think subscriptions are amazing.
Like, and, and it's kind of ironic in some way because a lot of your experience or most is, is in SaaS, right? And like SaaS- Yeah. It's all, it's all sa- B2B SaaS companies. SaaS is an amazing, you know, business model.
There's a reason that the, the, the, you know, the brightest minds of our generation, right or wrong, [chuckles] has gone into B2B SaaS. It's not because they're necessarily...
I, I don't wanna speak for them, but I don't think it's because they're necessarily passionate about business software. It's because the dynamicsOf SaaS businesses are pretty remarkable.
Outside of Google, they're like the mo- like one of the most remarkable business models around. At least they work, right? Yeah, and we can get into this 'cause there's so many ironies about my business in particular.
I make money writing about venture-backed B2B SaaS startups for the most part. Yeah. But I am not a venture backable business.
At least I, I don't want to be, and I don't think I appear to be either, and I'm also running a heavy advertising playbook. Yeah, [chuckles] exactly.
So it's- Well, it's the cobbler's son, you know, never has shoes- Yeah... kinda thing. Every single, every single, like, digital agency I ever, like, covered always had a horrific website.
So, uh, you know, [laughs] it's, it's pretty... But, like, you know, the, the, the SaaS playbook is just because it's all recurring revenue, but when you get into content as a product, it's a little...
It's, it's different, right? Like explain the, the dynamics between, like, a recurring revenue software model and, like, a Substack recurring revenue content model. Oh, yeah.
Well, so I came from a world where we would try to sell large contracts to other companies that were recurring revenue. So say they agree to buy $100,000 worth of stuff every single year.
The marginal cost to sell another license to sell to another company is pretty small. When you get- Yeah... into the content business, you have to keep producing that content, so you're kind of- It sucks...
on a treadmill. Yeah. I w- I, I want a business like PandaDoc, where I'm like, "Oh, I need to add one other person who can, like, download this con..." And they're like, "Oh, you gotta pay for that." Oh, yeah.
Like, and now you- What, what... I'm like, "What did you do?" Like, what did you- Nothing... like, literally, what did you do? Yeah. So fr- from that perspective, y- you're always coming up with the goods. You, you...
I'm, I'm a big fan of The Wire, and they would always say, "You gotta have dope on the table."
Like, when you're in the content game, every week you gotta have dope on the table to make 'em stick around, or else people will leave.
Whereas software, like, you know, they take it, maybe they use it, maybe they don't, but it keeps kinda running in the background and, and they keep paying for it.
And what I found too is that it's hard in the content game to sell 100 licenses at once. To sell 1,000 licenses to JP Morgan or something, like, it's really hard to do that with y- a Substack s- subscription.
Maybe I could get, like, 10 people to buy it, but it was pretty hard to go after learning and development budgets all at once.
But what I eventually realized was, and I mean, like, I, I knew it because I, I was a CFO, the buying power of the CFO is extremely strong and valuable. Everything goes through the CFO. Everything. Everything. Yeah.
And what they're buying are usually tools that have a really high sticker price to them as well. So it could be, like, an accounting system, it could be a billing system. These things...
The, the advertisers that work with me on the, on the kinda smaller side, everything starts at ca- $25,000 per year. But on the higher side, they're paying hundreds of thousands to- Yeah...
million dollar plus for these products and services. And so it's a ve- it's a very contemplated purchase too, which, which I, I take seriously.
What's nice about it is it lends to needing to align w- what I look at as, like, the procurement cycle for someone who's reading or listening to my stuff, along with the advertiser.
Because, like, if you come to me and you're like, "CJ, I wanna run one ad on Mostly Metrics," I'm gonna be like, "Thank you, but, like, if I run one ad, you're not gonna be happy with the results." Yeah.
"I'm not gonna be happy with the results." 'Cause Brian, the CFO, is not gonna wake up one day and be like, "You know, I saw that one ad. I wanna pay you $250,000 for a new ERP." Yeah. It just doesn't work that way.
Let me rip out the ERP. I, I, I've seen enough. Um- I've seen the light. [laughs] Yeah. You know what I'm rem...
There was a great Acquired episode, like, a week or so ago, and they had Michael Lewis was interviewing the Acquired- Yeah, I heard that one... duo.
You know what was really interesting was when they started talking about advertising and the business model. The difference between, like, a Michael Lewis and the, I forget the name of the guy, the Acquired guys.
But, like, they, they, they're looking at things from their background as, like, businesspeople first and foremost. He's, like, a writer, right? And so he...
When he thinks about the sponsorship, he, he is like, "I think it should be about things I'm really into and love," and all these things like that.
And it's like, they're like, "Yeah, B2B SaaS is, like, actually better for our audience." Like, you know, okay fine, we might, like, like this, this, this SaaS solution.
But, like, the reality is, you know, Michael Lewis gave the example of some underwear that he really likes.
It's like, well, okay, but, like, the LTV on, like, an underwear purchase is you're gonna need, like, massive numbers.
And the ideal is if you can have Acquired, where they do have really, you know, relative for podcasts, very big numbers.
But they're able to sell in a B2B category where, you know, the, the amount people will pay is just far higher.
And I've experienced this firsthand, because they were giving the example of somebody goes and buys JP Morgan payments. Like, they, they amortize the entire advertising cost over one customer. Yeah.
And I was working with, with a well-known accounting company that sells software for hundreds of thousands of dollars, and I remember in the first two months they're like, "Hey, we haven't seen a sale yet."
And I was like, "Okay, I know. I'm, I'm still producing the content. I, I hope you, I hope you still like it. Like, people are clicking it and stuff."
Month three they're like, "Hey, we've seen, like, some clicks and stuff. We haven't seen anything." Month four, purchases started to happen. Like, and they wouldn't tell me how big the purchases were.
But wait, would they be able to track? 'Cause I think one of the challenges... Everyone... You know, I think B2B is not a secret now. Everyone wants to sort of, like, you know, get in on it.
But, like, ultimately you gotta pro... I always say you have to produce receipts, and it's, it's a little bit more difficult with these long sales cycles.
I mean, your, your, your advertiser are people like Mercury and Brex, and I, I don't... Maybe that is a short... I don't know how long of a sales cycle it is.
But then also the reality of how, you, you know this, like, the reality of how people make decisions when it comes to these enterprise software decisions is, is long and it's complicated.
So how do you end up proving it?And that's exactly what happened because it took a lead legitimately four months to go through the initial, like, interested cycle all the way to a closed deal.
And on that fourth month, one or two deals hit, and it was-- it, it must've been a lot more than they were paying me because then they signed up for the remaining twelve months, and now I've been working with them for eighteen, twenty months straight.
But to your point, that's something that I learned early on, that you have to align the advertising cycles to whatever the procurement cycles are. And inherently, there's a bit of, like, trust that you have to have.
Mm-hmm.
And that's why I look to build long-term relationships with companies because, listen, like, nobody's gonna show up overnight and just, like you said, decide to take out their billing system or something like that.
But if I've formed trust and a habit, habit-building relationship with the user, over time, that will play out.
But we both have to go into it e-eyes wide open that, like, we're dealing with smart people who make contemplated purchases and will also ask other people in their network. Yeah.
So do you only make annual deals then because of that?
I mean, like, I know like, you know, in a-- in, in another podcast you had said that, like, you've pretty much sold out inventory, at least on the newsletter, and I think a lot of the, the podcast for twenty twenty-six.
So are you just focused on having a small group of sponsors? Because there's... You know, look, there's, there's advantages.
I know-- I, I'm asking this because, like, it's, it's something I'm trying to figure out- Yeah... in that, like, you know, the-- to me, it's like, it's not one or the other, right?
Like, having, like, a few really big and important partners is something that I try to have, and I, I do, right? And those are, like, long-term, you know, long-term relationships. They last throughout the year.
But the reality is, and maybe the spaces are different, like, that I need to also diversify and have a bench of people who are-- they're just not going to do year-long deals because of, of-- There's a lot of vendors in, in the space that I operate in, and they don't-- they're not gonna have only one provider, and so their budgets are such that, you know, they might just wanna do, like, one dinner or something of that.
Yeah. But I wanna get them to the point where they're, they're, you know, annual partnerships. Yeah. So I'm fortunate.
I have an amazing salesperson that, that helps me get the word out there, and he helps broker the longer-term relationships.
But we've sold out all the newsletter spots across both publications for next year, and then we only have one spot in Q3 and one spot in Q4 left on, on the podcast at this point.
And thirty percent of those deals that we closed are, are annual deals with partners, where they're in some medium, whether that's a newsletter or podcast, every month for, for all twelve months.
And those don't happen overnight either. O-one of these companies who's doing an annual deal, I met them in, in twenty twenty-one, right?
And they'd actually never purchased anything from me, except m-maybe, like, a couple thousand dollars from one post. But, like, we always kept in touch.
We, we always tried to give each other advice on what we were seeing in the market and stuff.
But these are, like, long-term enterprise deals, which is a fascinating spot to be in because I came from, like I said, the enterprise B2B SaaS world, where you're, you're trying to sell a pretty, pretty big sticker size to somebody, where you have to go through all these chains of approval.
And now I found myself in that, in the advertising business. And so the shortest commitment we'll do is at one quarter. The majority of companies do minimally six months.
But the shortest we will do is three months because the-- that's where I, I know that I can prove the ROI that you're gonna wanna do more. So that, that's kinda where the s-the starting place is.
So you s- so you sell newsletter ads, you sell podcast ads, and then I would say there's, like-- that you sell subscriptions, right? And then I would consider, like, a services bucket, right?
And, and by services, I mean, and we talked about this, like, you know, the, the dinners, breakfasts, whatever you wanna call it, some kind of way to, like... Oh, and I guess you do recruiting too, and that's like...
But break out, like, each of these buckets because you started with subscriptions, and that went well, I, I take it. Yeah. But you, you hit a wall.
Like, I mean, your, your ambition for this business, and this is something [chuckles] we had been talking about before we started this, is, you know, you were a CFO.
Like, you're used to making three hundred, four hundred K a year and then also having somewhere between, like, a, a, a lottery ticket and an annuity where you've got equity up to, like, one percent or so i-in the company.
And, like, you know, these companies, you know, if you sell for three hundred million dollars, that's, that's quite a bit of money.
So when you decide to go let-- to go full in on this, which was early last year, you're gonna, you're gonna have to, like...
Your ambitions are, are higher than, no offense to my journalist friends in Fort Greene, but your, your [chuckles] ambition, financial ambitions are a little different. Yeah.
I-- my financial ambitions were definitely different.
I, I also come from a world where I've been helping grow companies that may make hundreds of millions of dollars per year in dealing with people who are, you know, amazing members of the C-suite who make a lot of money and dealing with investors and bankers and stuff.
So I also interview people every week on my podcast who definitely make a lot more money than me, and many of them are public company CFOs.
So it's funny, like I, I look at the numbers that I deal with, it's still really small compared to the world that I came from. Like I'm- I know. That's such an advantage. It's such an advantage.
I'm very fortunate, but, like, I don't look at it like this is a massive number. I look at it like I'm still an ankle biter.
It's very small, and I'm like, you know, I'm still day one in, in my parents' basement, like, with the numbers that I'm dealing with now compared to then.
But, like, the way that IWhat I had to get my mind around is I'm running a company where I wanna be able to do it again tomorrow, and I wanna keep doing it the week after that and after that and the year after that.
Whereas I came from a world where every company I was at, you were, you were hypothetically always for sale. I came from a world like- You're on a clock. You're on a clock, right? Yeah.
Where most of them were driven, were, were PE-owned? VC-owned and PE-owned. So, so I've done both. But either way, they were investor-backed and- Yeah...
like I, I ha- I had good cash comp, but like the, the point of it was to get to a point where all our incentives were aligned, and we were able to sell the company at some point for, for a big windfall.
So I, I had to step back and say, you know, I, I could keep going as a CFO, and people can look up the comps, but if you're a private company CFO, you can make between three hundred and four hundred thousand dollars in cash a year, and then you get about one percent of the company.
That can either be worth literally zero, or it can be worth a lot of money.
And if you get to the ranks of a public company CFO, you can make five hundred to seven hundred K in cash a year, and it, it could be, it could be five million dollars per year in equity, it could be twenty million dollars per year in equity.
Now, there aren't many of those people out there that that's the, the cream of the crop. But I think I had to step back and say, A, do I think I could get to that point of being like a public company CFO?
Like, do-- am, am, am I good enough for that? Yeah. Because I've talked to some people who are... They are ten out of ten. Killers. They, they are killers. Yeah. They're amazing.
You, and you have to be, you have to be like honest with yourself about like- Yeah... what, you know, your unique skill set is. And I think what you're unique at, and that's why I compare you to Lenny.
I don't know if Lenny is like, you know, the, the... I mean, like, I actually, I sort of know because Alex Schleifer, who does the PVA with me, he worked with Lenny, and he was like, "Oh, Lenny's a great guy."
He's like, "He was one of lots of product guys we had." Like, now I'm not saying you're like one of lots of like CFO people, but like- No... Lenny- I, I probably was. I probably was...
what he had was that he understood the space. He was, he was good, right? He was good at product.
But he also then had that other gear, and that is to be able to create engaging, quote unquote, "content," whether that's, you know, writing an analysis or whether that's podcasting and being able to package it well.
That is a real skill. Now, usually you have journalist content types who are kind of almost like faking it, like with the expertise side.
I mean, the reality of like journalism is they, they train you to be a generalist, and so like you can, you can act smart about all kinds of things, [chuckles] you know? Yeah.
My advantage, Brian, is I'm probably in the eightieth percentile for CFOs, right? I'm, I'm pretty good. Maybe I'm the sixth man off the bench for the Boston Celtics, but I'm- All right. That's good...
but I'm not Jason Tatum. City Moncrief. Like [laughs] Yeah. Right? [laughs] He makes pretty good money.
And I'm probably in like the eightieth, ninetieth percentile for writing, and then I'm also probably in the eightieth or ninetieth percentile in, in business sense on how to make money off of something.
Like put, put me on an island, and I'll figure out a way to sell coconuts. And you take those three things and stack them together, and my goal was to take that and be an N of one.
Whereas if I'm competing just straight up with somebody else... Like I interviewed the CFO of Samsara, and it was like one of the first times on a podcast where...
And, and I'm doing it live as I'm having this realization. [chuckles] I'm like, "This guy is fucking impeccable." Like, I don't know if I'm ever going to get...
'Cause before that, a lot of the CFOs I'd interviewed, like, I was like, "You are amazing. I think one day I can really work at it and become you." Yeah, yeah. I, I know that feeling.
This is one of the first times where I was like, "I don't think I'm ever gonna get to like how good this guy is." But I think in the way that I stack my skills, I can create a category that's my own.
And I also have to say the competition is less too, because it's not something that people are graduating from Wharton or HBS saying, "I'm gonna create a newsletter business," right? No.
No, because the incentives are, are... And the personality types are different, and also the skill sets are different. I, I don't know. I mean, maybe a lot of CFOs are like great writers or, you know... I just don't...
Usually, those skill sets are, are somewhat different. It's definitely more rare for- Yeah... for finance people. Yeah. So break down, so like...
So break down, like ninety percent is now subscriptions, which is like- Yeah... kind of remarkable. That's right. You went from like zero percent... I'm sorry, ninety percent of sponsorships. Yeah.
You went from like zero percent being sponsorships, like I guess a couple years ago, to it being ninety percent because it's so- Yeah... valuable and because you execute real well. Right.
So in the f- first year I, I monetized, it... the majority were subscriptions, and we did like one hundred and fifty K in, in, in revenue.
Second year, flipped on the switch for advertising and also added a podcast. Did one point four. And then the, the next year- Flipped the switch.
[chuckles] The, the next year, and this is where- You're gonna get death threats from, from newsletter people, CJ...
and then the next year, this, this is where I feel like if, if you give me ninety percent, you get ninety percent back. But if you give a hundred percent, you get a thousand percent back.
And this is where I, I said, "I'm not gonna take another job. I'm gonna go full time. I'm gonna make this like what I do every single day." That we got through three million this year, so I feel really fortunate.
So wait, but wait, you had a one point five million dollar side hustle? Yeah. Oh my God. Yeah. [laughs] Yeah. So I mean, and they just- Why are you trying to help me like that, Brian? I mean,
I, I want you to yank open the kimono because I think like, you know, look, a lot of people focus on a lot of like glitzy busi- like, you know, like Emily Sundberg. I, I like Emily. I lo- I like what Feedme is doing.
I think there will be other types of Feedmes. But I believe that like, you know, the sort of...
If, if you are sort of the, the Lenny of CFOs, there's lots of other like CJs of different areas, and that is people with deep-Expertise in that area who then are also able to, to create content that is engaging and, and useful, I think most importantly.
Because you're running this incredibly lean, right? Like, I mean, it doesn't take a lot because... And, and, and I wanna talk about the, the sort of risk of that because y- you, you have to think about that too, right?
Like, I mean, about building enterprise value, or maybe you don't b- build enterprise value. I don't know.
I think, uh, there's a lot of people in this area, count myself as one of them, who is like, "Okay, I've-- I-- I-- this, this works absolutely as a business," but is it a business? Like, is it like I get hit by a bus?
Like, what is it? I saw this tweet from Matt Paulson, he runs MarketBeat.
Mm, I, I like a lot of the stuff he puts out there, and he said, "Everybody celebrates the guys who sold their media business for seventy-five million, but nobody celebrates the people who are clipping off five or ten million dollars a year and get to keep it forever."
And so I thought that was pretty powerful, that like it doesn't- Yeah...
always have to be about how do you sell this thing, and this is coming from someone who literally made their career on raising money, raising hundreds of millions of dollars in selling companies. Mm-hmm.
But I've come around to just the joy and the ability to control something and be- Yeah... your own boss, and to live off the cash flows from that.
So it's just- That's a- It's just- That's an unbelievably important point, 'cause like I feel like we came in this... came out of this era where a lot of people, like, were focused on exits, right?
It's like, you know, and I, I had that. Like, I was part of that. Like, you know, thinking, okay, s- now, you know, I, I haven't had a 401k for, like, 10 years to [chuckles] like...
But, like, there's gonna be some kinda exit, and you can't control that, right? And you can...
If you have a cash flow generating, if you're at three million now and you're running this thing at, at 80% margins or something, like, even for someone who's doing the opportunity cost of being a CFO against that, th- those number...
I've run the numbers, CJ, that works. Yeah. It, it definitely works, and yeah, it, it works. And I, and I did run the numbers on it. I- [chuckles] I hope so... like how much of a sicko I am.
I, I, I worked backwards towards how many at bats do I think I can have in my career as a CFO. And so if you come up with an- Well, you're like, what, in your early 30s? Where are you? Yeah. Okay. I turn 35 pretty soon.
And so I, I feel like I'm 70 though, with the years I've worked and the articles I've typed, Brian. But, um- [chuckles] Yes. But, but I worked back- It, it does age you. If, if- I, I will say that.
[chuckles] I worked backwards towards if I was a serial CFO, let's say I get five more swings, right, before I have to hang it up. First of all, it's a pretty grueling path. You don't truly control your own schedule.
There's a lot of stress involved with it, and maybe only two of those end up panning out. One, you get to even, and two, completely blow up.
Now, there is an element of preferential attachment where if you do great at one, you get to level up the game and you, you keep getting a, a slice of the pie in, in a bigger and more successful potential outcome.
But then I, I looked at it and said, "If, if you can reliably make two million dollars a year or more and control your own destiny, and also take your daughter to dance or karate at three PM on a Tuesday if you want to," like, that, that's a pretty cool life too.
So I don't think there's, like, a right answer, but there's an answer in terms of what do you get energy from and where do you think you're most uniquely qualified to win.
And we touched on it at the beginning of the podcast, the whole B2B SaaS thing.
Like, I'm operating in a model where CJ 10 years ago would say, "This is not as great of a business model, like, on the surface advertising as, like, I don't know, selling cloud infrastructure to a company."
But if I'm really good at this, it is a good model, right? Like, if, if you're really good at the grocery store business, it's...
The, the best grocery stores are, like, a 7% margin business, but if you're, if you're the best at the grocery store business out there, like, that, that can still be a great business.
So it's, it's what do you enjoy doing and what are you uniquely qualified to succeed in? Yeah. So tell me about how you thought about creating, like, the products to get there. 'Cause it's...
'Cause I, I guess, like, I think you've been, like, very disciplined about not getting pulled into being an agency. Like, I think a lot of times- Yeah...
in media you are, and maybe I'm telling on myself here, you're just, like... You're, you're a dog with your tongue out, and you're, like, trying to, like, you know, you're like, "Yes, yes. I'll do that. I'll do that.
I'll do that. Absolutely. I'll be there." Like, "Yeah, I'll do that." And you end up losing sight... It, it's very easy, I will just say, to lose sight of not keeping the main thing, the main thing, right?
Because ultimately- Yeah. I say no to, I say no to almost everything. Right.
Because I realize this funny thing that happens when you have, like, a modicum of success, and I'm not saying I'm at the top of the game or anything, but just, like, when you get some traction, you start to have opportunities pop up where it's like, "Will you angel invest in this?
Will you be an advisor in this? Will you be speak at this event?" And all those things are friction against the main thing that got you there.
And what I realized is nobody's gonna wanna hang out with me, nobody's gonna want to sponsor my stuff if that stuff isn't good.
And there are a lot of people out there who say, "Oh, I have a newsletter, like, why can't I get good rates on this?" Or, "I have a newsletter, why isn't it growing?"
And it's because they don't make the newsletter the main thing. I look at my... Like, you could call it whatever you wanna call it.
Like, it, it arrives in your inbox, and you can query it on the web, but to me it's a product. It's something that I take pride in.
It's something that I hope has a certain feel to it, and you get a certain, you get a s- certain, like, dopamine hit when you read it.
And, and I, and I try to take that really seriously, because if I don't have that, I don't have anything else.
So you, you do small scale events, 'cause I think about these things as like-B2B is kind of a cheat code, honestly, B2B media, in that like compared to consumer media, which is con- in constant upheaval because the lack of control of distribution, the lack of control of monetization with programmatic.
B2B, it's hard. Everything is hard, right? But like nothing is like reinvented. B2B typically is a lead generation business. Yeah.
You sit between a buy and a sell side, and you provide leads to the, the sell side to the-- to their prospects. And those leads can come in various forms, right?
They-- people can click on a, click on a, a, an ad in your newsletter. You know, some people will do, you know, like webinars.
You can do like co-branded research reports where information gets passed or you can do in person. I would call it sales enablement.
I call that like sales enablement to some degree, where you're matching up literally a buy and a sell side, and that's where, that's why B2B is so event-heavy. He makes the game so simple, folks.
No, but honestly, like you've given me great advice on this because you, you, you told me that time th-that we met up in New York, you, you gotta have receipts for no matter what you do, right?
Like that-- You gotta give them a receipt at the end of the day for I brought people here, I brought leads here. You can prove something.
The way that I've tried to construct it is there are network effects between everything, right? And- Yeah...
just having been the person too who gives the budget to the marketing teams, I understand that there are different categories within it, right?
So I'm a sicko in the, in the sense that like I, I think about the marketing budget in terms of how I would budget for it as an FP&A person, and the results and how they trace the pipeline of how a CMO would see it, and then how a CFO would look at the results.
So for me, the newsletter is the demand gen that is directly attributable, that comes from a different budget. And then you have the podcast with it, which is more brand-oriented, right?
It's the, it's the air game if the newsletter is the ground game. Yep. And then you have the events business- Yep... or, or kinda, you know, add-on that you can do where you actually get physical people in a room.
And that is the most valuable one. That is the most valuable.
That is the mo-- And I am lucky enough to have built relationships with CFOs where I do these small dinners where I get twenty-five to thirty actual CFOs in a room, and a few of the seats are, are for sponsors that we sell.
But I'm not an events business. I'm clear with everybody about that. That's just something I do because I enjoy hanging out with the CFOs. I enjoy giving the sponsors other avenues. Oh, it's a slippery slope, CJ.
It is a slippery slope. I don't wanna be in events business. Like I never got into this. Like I, I'm actually an introvert. We're, we're gonna be talking in like two years about CJ Con and [laughs]
and then- But, but I think the key to that, Brian, is you have to- You will, you will, you will see what the events budget is for Brex and Mercury, and I suspect you'll put on your FP&A.
I don't even know what those letters stand for. You'll have to tell me a little bit. But like- But, but you wanna gate that though, right? You don't wanna give away the, the golden goose- Oh, yeah...
without having them sponsor either the newsletter or the podcast. Yeah. Hundred percent. So the way that I, I do it is like I wanna build a long-term relationship- Sure... with you.
Let's plan on something around the two medium brands, media brands, and then we can also figure out something with the events and reports. And all of this has a network effect to it. Yeah.
You know, I th-- I've been thinking about it a lot about...
And you know, I think a lot of times peop- th-there's lots of words that are used as euphemisms, but I think there's a difference between having a partnerships business and like a sales business. Yes.
A- and y-y- they're just, they're different. Like if you go back to that Acquired podcast, they have a partnerships business. They partner with, you know, JP Morgan Chase payments, and they do a bunch of different stuff.
They'll do like client dinners and whatnot, but like they'll do, you know, uh, uh, the event at the whatever Chase Center, et cetera, and that is a partnerships business.
Sales businesses are, you know, typical B2B media businesses where you, you send out like a wave attack of salespeople to knock on every single door, you know, and, you know, s- pump out emails, get more meetings.
More meetings means more proposals. More proposals means more sales. "Hey, ha- have you gotten the key card sponsorship? What about the Wi-Fi?" "Okay, well, you know, we can do the sponsor-tini." You know?
And that is, that's a churn business. You know, a lot of people in B2B, at least in my area, have a fifty percent churn of their clients, and you gotta keep, you gotta keep filling that pipeline because...
And it can work in different categories. So, you know, I always, you know, going back to my-- the last company at Digiday, you know, that was in the beginning of the growth of programmatic advertising.
What happened was, you know, venture capitalists funded a whole bunch of point solutions that could never really be companies, but they were very motivated.
Once they hit their Series B, they had, they ha-- it went into sales and marketing. You know, like SaaS. Like what are- Yeah... what is Pandadoc paying to like give me that extra login?
A-all their money goes to sales and marketing.
And when you have those like LUMAscapes, there would be these landscape slides of like that bucketed all the different like providers that literally were just taking a bite out of like an ad as it moved across from like [chuckles] a brand to ultimately a publisher or a platform.
It was like how a bill becomes a law, but like much more grotesque. And you just machine gun those logo slides, you know? [chuckles] That's a sales business. Partnerships businesses I think are different.
They are different, and one of the advantages I have is coming from the space and actually having purchased a lot of the, you know, stuff that-People are advertising. Like I've- Yeah...
worked with Brex and worked with- I was listening to your Tipalti ad. Ha- as, as someone who has used Tipalti, I was like, "Oh, man, I don't know." So, so that, that, that helps, but I...
it also helps that, like, I'm not accepting sponsors who I- I'm like, "That doesn't even make sense for my audience." And that's where a lot of the churn comes from, 'cause people are like, "A dollar be a dollar." Yeah.
Like, money be green.
And to me, it's I only wanna work with-- I want to align myself with the best products out there because it-- what we were talking about before of wanting the, the point of playing the game is to keep playing it. Yeah.
I can only do that if I'm working with great brands that are around and also growing. And I do think a rising tide lifts all ships, that if I'm working with the best brands- Sure...
and I'm putting out great content, like we both grow. And that, yeah, that does sound kind of woo woo, but if you're just chasing it for the next dollar, like that's a pretty short-term- Yeah...
that's a pretty short-term perspective. It's funny. It's like you do have... Look, you've done an amazing job, but you do have a lot of built-in advantages.
And one is just like, I'm so envious that, and tell me if I'm wrong, you're in like a stable category, you know?
Like, I mean, one of the challenges that I run into just operating a business, and I just think it's a feature, not a bug, is because there's so much upheaval in it, particularly- Yeah...
you know, most of my clients are, you know, doing business with me in order to sell some form of software to a large consumer publisher.
Their businesses are in such upheaval that the pr- the provider side, the technology side, is always changing. They change their target. Like, I will have a client... This is like a therapy session now, CJ.
I'll have clients, I always have this, where all of a sudden they're like, "Yeah, we're not selling into the category anymore." They're just like, "Publishing, there's no money there, so we're just gonna stop.
We're gonna stop. We're, we're, we're focused on marketers, retail media, or whatever. We don't, we don't need that." And it's like lit- and they're like, "No, no, no, it's not you. You did great."
That's frustrating, but you're not gonna have that, honestly. Well, that, that's, that goes back to having a business sense. I would never choose to play a game- Shout out, business sense. Facts. [chuckles]...
instead of a different game if I wasn't gonna play on, on, on not easy mode, but have some... I, I wanna be running downhill with this, right? Like I, I didn't wanna be- I like to run uphill.
You know, you're a runner, and like I think- Yeah... you get stronger running uphill. But that, that's why it was attractive because, A, I, I was a practitioner, so I could speak from a, a perspective of like- Yeah...
knowing some shit, right? I didn't wanna be like some dilettante that like was like... What's the saying? Like those who can't do, teach. I didn't wanna be that person.
That's why it was important to me to, like, actually sell the company and have an exit that I was a part of before doing it on my own. Second, it, it's a durable category that I'm in, right?
People have three to five-year contracts with a lot of these different software providers. And third, I understood that the ICP was someone that had a lot of decision-making authority for their department- Yeah...
as well as the rest of the company. So looking at that, like thinking about where you wanna invest your time and what you could be doing elsewhere, it seemed like a pretty, pretty good bet.
So d- let's talk a little bit about the, the content because, like- Sure... I think what you quickly... Like, and I think
y- your area like lends itself to it, but I think y- obviously your experience lends it to tactical. Get- Super tactical... tactical. Oh, man.
There's so many books out there written on strategy and so few books written on tactics.
If I think about what gets somebody promoted at a job and helps them make more money, it's literally like, "Give me the Excel formula to type in for this thing." Yeah.
It's not, "Well, hypothetically, I think AI companies have worse margins, and what will that maybe bring to you?" This is another advantage of not coming...
of coming from the practitioner side versus, like, someone like me. I'm like a weird sort of thing, but, like, w- who... You know, I come from, you know, a journalism background, right?
And so, like, we do like, you know, narrative and all of that kind of, of, of stuff which is- People think that tactics are below them. They really do, especially- I don't... in my category.
Like, you see a lot of people out there who write these thought pieces, and I was like, "That was interesting. I can't really do anything different in my business tomorrow." And so- Yeah. Here's a playbook.
Here's a framework. Yeah. Yeah. Here's a prompt for ChatGPT that'll help you, like, figure out your P&L. Like that, that's worth it, right?
You'd pay $15 a month, or people would pay to get in front of your eyeballs because you're somebody who's in the know and actually trying to make decisions within the company. Yeah.
But it's also, it's where you come from, right? 'Cause like you gotta- It is... you gotta dance with the one you brung, and like if- [chuckles]...
if one of your unique skill sets is not FP&A, but it's like, you know, narrative and being able to like, you know, write th-that way, you know, it doesn't make sense to, to do a bulleted list of like the ChatGPT prompts that will get you this or that and the other.
So, yeah. I also find that there's a lot of value in leaning into the if you knows, then you knows. So there are certain things that if you've been in the role before, like wink and a nod, you'll understand.
And having that relationship with the audience over time, it demonstrates that, like, you've been where they are before, and just that, like, you're, you're a part of the world they're in. And a lot of people...
You don't wanna read something and feel like it's an outsider trying to tell you how to do your job, or that they're speaking down to you. And I- Right...
hope that in my writing, a lot of it comes across not just as, here's how you do something, but here's how I felt when I was having imposter syndrome in this role for the first time.
And I was like, "Is, is there somebody gonna walk in the room and be like, 'Who let this guy in here to make these decisions?'"
And so a lot of it too is looking back at either times where I didn't know what to do or when I was trying to figure it out live. So it's not just like, "Hey, this is the definitive way to do something."
It's, it's kind of a view through someone's career as, as they figure shit out. So you've... Y- you're in an enviable position right now in that you have-Sort of content market fit.
The business is, is working really well, right? And so you have a ton of flexibility. I know you'd like to like, you know, say, "I've got 17 kids, and they all need, like, childcare and everything."
Like, you've got that covered. You have, you, you have money to invest in the business. Yeah. Right? And then the question is how? Because you have a very lean structure. I don't think you have any...
Do you have any full-time employees? No. You have no full-time employees. You've got, like, a podcast producer, you got someone on, obviously does, like, accounting or whatnot. Or maybe you do it yourself, I don't know.
You've got, you've got a sales k- sales guy, I guess I'll call him. [chuckles] Who's your salesperson? Sales guy Matthew. Sales guy Matthew, okay. Yeah. Good, good. [chuckles] You got, you got, you got him.
Who else, who else is in your, like, stack? So there are two producers. So everyone's a contractor right now. Yeah.
They invoice me for the work, and I'm trying as long as I can just to not have the overhang of, of, like, running a big W2 company. Maybe it's because I'm also a little bit burnt out from having done that as a CFO.
Wait, talk to me about, talk to me about that, because I think that is different in many different ways. I'm sure you run into this, 'cause, like, you're in the civilian world, right?
So, like, I mean, you run into people and have to explain to them, like at like soccer games or something like this, what you do, and they probably look at you are like, "Are you okay?"
Like, [chuckles] "Are we-" Oh, yeah. "Can I help you or something?"
[chuckles] It's funny, my wife was at lunch with my daughter, who's four, and another woman from daycare with her daughter who's four, and somehow they just start talking about what, like, the husband's doing.
The woman is, like, a high profile, like, commercial real estate executive. Her husband works at a hedge fund. [chuckles] And she's like, "Oh, what does your husband do?"
She goes, "Oh, he has a, he has a podcast and writes online." [chuckles] You're in Conne- And she's like- You're in, like... Wait, where are you? You're in Connecticut, right? Yeah, I'm in the Westport area. Oh, okay.
So yeah, I mean, you're like, [chuckles] your neighbors are, are not, are not podcasters. [chuckles] And so the lady's looking at my wife like, "Do I need to pick up the check?" Like, are they... Is this- Are they okay?
Are they okay? But people don't really-- It doesn't really occupy, like, a space in your mind where you can benchmark it. Because saying like, "Oh, I'm a tech CFO," it, it, it does have a certain amount of cache.
Yeah, yeah. It's like it's easy, then you can go on to the different things. Whereas I had to, like, take like an ex... I'm like, "Okay, so here's what it is that I do." Here we go.
It is hard to explain, but the way that I've looked at it from the beginning is, you know, you make the content the main thing, and then you have an audience, and you essentially have a customer list, right?
Because I came from a world, Brian, where we would invest millions and millions and millions and millions of dollars into building a product, and then we would cross our fingers and invest millions and millions and millions and millions of dollars into a sales and marketing team to go out and try to sell it to people who, like, hopefully they wanted it.
What I've done is the reverse. I built the customer list and the audience. I respect their time with every single piece I put out there.
Hopefully, they trust me, and now I can figure out what needs that they have around that.
So the areas that I'm investing in are recruiting, which I'll touch on first, and I hired a, a full-time recruiter, also a contractor, so I don't know if you'd call that full-time.
If you're the IRS listening, it's not full-time. No, absolutely not. They don't have an office or anything. They work for other clients. No, they don't. But they, they don't have an office.
They bought their own computer. [laughs] Control their own schedule. What... And what happened is, like, they're...
Having this type of business, it's kind of like the serendipity engine, where you, you just meet people and they tell you things, and they find it interesting.
And when you have a channel for distribution, things come up. And so having beers with a number of CFOs at these dinners I host, once again, not an events company, but I do hold them.
And within the same month, two CFOs just said, "Dude, can I just pay you to help me hire these, these people? I've, I've had the hardest time doing it." And I had said I didn't wanna be in the recruiting business.
Like, I actually don't really like recruiters. I'm sorry if you're listening and you're a recruiter. I'm sure you're a nice person.
But, um- That's the best way to get in the recruiting business, is say you don't like recruit- recruiters. I, I don't. I've, I've had to pay millions of dollars in fees before if I've been- Yeah, I know.
This is, this is how it is. It's like I had this problem and then I solved it. Yeah. Yeah. And so I was like, "Yeah, sure, I'll give it a try." And so I put out the bat call to the audience, "Are you looking for a job?"
Blah, blah, blah. Hundreds of people say, "Yes, I am." And so now we have a... Basically we've hacked the pipeline. We've activated a pipeline of people that we can pre-vet and then matchmake instead of- Yeah...
like recruiting with the people on the other side. So that's, that's one of the big bets for next year. And it's, it's not like just a money grab either. Because with recruiting you- I'm helping them get jobs. Right.
Yeah. And it, it makes complete sense. And I... As I said before, like, I mean, 70 odd thousand. There are not... I don't think there are 70,000 CFOs in, in America. I could be wrong.
But you've got a lot of people who... And this is the reality of any of these businesses, is like you have aspiration. I mean, you were not even actually a CFO originally when you were start- Yeah... creating this.
When I started it. But, like, you know, people are on that path, and they want to, to get there, and that's like a, a, a normal, a normal progression, right?
But, like, you know, this service makes complete sense because for a few reasons. One is, like, I hate job boards. Like, I hate them.
Like, I've tried to do them, like, so many times, and it was never worth, it was never worth it.
You would collect these, like, little, like, $200, like, hits, like, again and again and again and again, and you would think that it would be like, oh, automated. It'll be all automated and stuff.
It was always, like, incremental. And so with recruiting, you get like, what? Like, 20% of the first year? We're just doing flat fee based on the role.
So I'm only hiring for managers, directors, and VPs of finance, and it's a flat fee based on success, based on that role input of- Yeah, but the flat fee is worth way more than, like, 200 bucks.
It, it's a very healthy fee. [chuckles] Yeah. You know, I mean, look, you take some amount of risk, and then, like, I think this is interesting because it's pretty servicey. It is.
And- I mean, it's a services business offeringIt is, but you can only get to that point if you already have the trust of the people. 'Cause I look at it like the customer are all the guests that I've had on.
I've had-- I've interviewed over two hundred CFOs at this point. And then the-- So that, that, that's the demand side. And the supply side are the a-aspirational- Yeah... CFOs who wanna get there at some point.
So it's kind of like you have the- And so they signed up. So you, you had like hundreds or even thousands, I don't know how many, like who signed up who's on the supply side. Yeah.
Like within the first week, like three hundred people signed up. That's great. So I haven't been marketing it very much until the full-time recruiter, not full-time- Okay... the recruiter starts. Yeah.
Okay, so that's gonna be a services line of, of revenue. That's the services line, and it's a, it's a very high margin services line too, which is great. Yeah, it's not creating white papers. No.
No offense to white papers. And then the other angle that I, I was pleasantly surprised by how awesome it is, is doing reports which are also sponsored, but around- I love reports. I love reports... tech-technology.
I know you do. I know you do.
[laughs] And mine are around purchasing decisions for technology, because if you have the audience to distribute it to and you have the audience to survey, then it's first party data that others- Yeah...
don't have, right? So that, that supercharges the efficacy of it. But do you sell those as like lead gen, or do you sell, uh, or demand gen, whichever you wanna call it? Like, or, or do you sell that as...
Like how do you, how do you monetize that? It's fixed price based on like this bill of goods that you get.
So maybe like I interview the CEO along with it, and you get up to three quotes, and then if you want to engage with us for the lead gen list too, then that's a, another separate amount. But the- Oh, okay...
two reports we did last year made the same amount as the ten dinners we did. Seriously? Yeah. I gotta change my reports.
So the reports, the reports are, are good, and it's something I enjoy doing 'cause I just like- Yeah... I'm a weirdo. I like enjoying doing the PowerPoint slides.
And then the third thing that we're doing is an extension kind of of the reports, but it's live benchmarking for tech stacks. So if you're a CFO, they used to say like, "No CFO ever got fired for buying IBM."
It, it's very true. You wanna know what other people are using.
And so I have enough people out there who are curious about it, where we can create the benchmarks and you can go in and figure out what's being used within your tech stack. Yeah.
And so I think G2, for those who've used it for tech before, I think it's like not specific enough to...
Like even if you're a marketer, you go on there, you're like, "This is kinda like close to what I need, but it's not specific enough."
I'm just maniacally trying to serve my ICP, which is a venture-backed or PE-backed CFO, and what they would need to make a, a purchasing decision.
So tell me about Mostly Growth then, because like I'm interested from a brand perspective because like, you know, you've got a few different brands out there. I don't know if it's like, if it's...
You've got Mostly Metrics is the, the flagship- Yep... newsletter, right? Then you've got Run the Numbers behind you there. That's- Yep... like your podcast. But then you, you've got Mostly Growth. Yeah.
So the way I look at it is like the house brand is Mostly Metrics, right? That's the main thing. Yeah. And then Run the Numbers is kind of the audio version of that, but in interview form.
And then what you can do is create more specific audiences off of that or tangential audiences to it. Sure.
So I have another newsletter called Looking for Leverage, and you are the one who taught me this, that you- Oh, really [laughs]... you, you can go even more niche into the niche, and it's actually more valuable- You can.
Yeah... on a per subscriber basis. And so that's my newsletter for private equity. Just merely from segmentation-- for segmentation purposes, it actually gives you leverage, actually. Yeah. Yeah. Yeah.
And it's, it's not meant to be the, the biggest newsletter. Like- No...
I'm sure if somebody out there could get the thirty-two NFL owners on one email list, that would be a very valuable list, even though there's only thirty-two people on it.
If I can have twenty to thirty percent of all private equity-backed CFOs who operate a little bit differently on one list, I don't need to have- Yeah... thirty thousand subscribers.
I could have nine thousand subscribers, and it's just as valuable as some newsletter out there with two hundred thousand subscribers. Do you know what percentage of your revenue is
tied to the newsletter versus non-newsletter? 'Cause I think one of the sort of- Yeah...
if I were to like do one of those like trends of like twenty twenty-six, I mean, I've been beating this drum for like, for years at this point [chuckles] is I'm kinda bearish on quote unquote newsletter businesses.
I mean, I think newsletters a-and selling newsletter ads is, is great or, or subscriptions. I just think the ceiling is fairly low for most categories. La- you're not...
Most people are not gonna build Industry Dive and, you know, they're... Th-that's the reality of it.
And so you're gonna have to end up becoming a quote unquote media company, and media companies do other things, you know- Yeah... because that's the reality of it.
I think about this so often, Brian, because ri-right now it's about forty percent newsletter revenue, forty percent podcast revenue, ten percent reports, ten percent dinners.
And none of it's possible, though, without the newsletter stuff, right?
So Ben Thompson was saying how one of the best ways to monetize is to use written word to then get people over to the audio format, because that has a larger surface area for monetization.
So if I look at my newsletter, I only do one sponsor per post, right? If I look at a podcast, it's a... it's less dollars per sponsor, but you can have six sponsors per- That's some healthy monetization.
I was just listening to one. Yeah. And but then you also look at it, like if I give you sixty minutes worth of content- Hey, I'm not, I'm not gonna...
Hey- I think ten percent of it, it's, it's- You're, you're not gonna get complaints- That's a trade, right?... about monetization from this guy. You got the wrong person here, CJ.
[laughs] But I do think over time, podcasts have a larger... They have a higher ceiling. But I also think that in bad times, people pull back more from those because it's less attributable.
G-going back to like where in the marketing budget does that sit? A lot of that money is risk capital that the company's putting up around branding.
And so when the going's good, it's good, but you do wanna diversify.Yeah.
And so final thing is like when you're looking out for like a three year, I don't know if you do like three-year plans, 'cause I, I, what I was saying was like, you have the luxury of looking ahead and being really thoughtful.
You probably take it for granted, but I'll be honest, like a lot of, a lot of people in this space who are like solo plus people doing like these independent like media businesses, they're on a treadmill.
They're on like a sales and services treadmill, and there's a lack of, of visibility. You know, I think one of the things
that is different for, you know, people who go down this path is you go from knowing pretty much what you're gonna make, like, you know, and fine, there'll be a bonus that's a little bit variable maybe- Yeah... to
you gotta like, you know, you, you have no idea.
And I mean, and for a lot of people, and, and I think this is where partnerships really come in, you just simply do not know, particularly if you're in a volatile category, how much money you're going to make.
You can try to forecast it out, but like it's really, at least I've found in talking to people, it-- the variables are like so great. It is nice that I know the minimum I'll make- Yeah... for, for this year.
But I mean, like me and sales guy Matthew were talking yesterday. We're, we're literally working on partnerships for twenty twenty-seven and twenty twenty-eight. So yeah, it, it...
People could say, "Oh, you can just sit back and chill, right? All you have to do is produce the content now."
It's like, no, I only got to this position because we had inked a one-year deal for twenty twenty-six in late June of twenty twenty-five. So I'm still very much on the prowl to line up these longer term partnerships.
So in that sense, like you can never rest. You're-- And you, you talk about that Acquired podcast with Michael Lewis. They said they're working-- They have sponsors already signed through twenty twenty-seven.
Like, I wanna get to that point. Sick. So like there's always an, the next mountain to, to climb and- They also have the number one technology podcast in- Yeah, I'm a huge fan.
[chuckles] So that is, that is like an advantage of... So I mean, but do you want to... Like, what do you wanna build?
Like, 'cause I mean, I think you can go in so many different directions with this business, and I'm just interested in how you look at it balancing sort of the personal with the, the sort of CFO mindset, right?
Like, 'cause I mean, I imagine from the personal- Yeah... you're like, "I like being able to walk my dog in the morning. I like being able to go to my daughter's, you know, recital." And the sort of CFO perspective is,
okay, how do we scale this? We've got [chuckles] we've got, we got a little bit of a tiger by a tail here, and there's a lot of different directions you can go. You can go deeper or you can go broader.
You could become, I don't know, like the ringer of like, you know, the, the, the finance class. I don't know. How do you think about it? I'm a huge fan of The Ringer. Bill Simmons is like my idol.
I often look at it like, I hope my voice comes across in my newsletters as if Bill Simmons worked in your accounting department, in your finance department.
Someone who, who doesn't take themselves seriously, but takes the work itself seriously. Mm-hmm. And I'm a huge fan of Deadspin and, and now The Defector, so those are like the publications that I grew up on.
And I've studied their models, and I just... I-- what I can't figure out how to crack the code on is how do you create an ecosystem where
people come and create content and they all benefit from the platform, but they don't churn out the top?
So if you look at anybody who's been at Barstool, Bussin' With The Boys, Alex Cooper, they all got to a point where they just said, "I can monetize this better on my own."
And I mean, I started my podcast on a network where I learned a lot, but like very quickly my CFO mind went to, "I can make more if I package the newsletter and podcast together." It was a pretty simple equation.
Oh, yeah. I remember. I think we talked about that. I was like, "Oh, I know." [chuckles] I called him before I, before I left it actually for some advice.
I just, I just don't know how you do that at scale, and so that's something I've, I've put in there- So you don't wanna bring on others.
I mean, you have like a collaborator that you work with on one of your, your podcasts, but it's not like you wanna hire a bunch of- But it's not like he's doing his own podcast and like...
'Cause you gotta figure out what, what's the most that you could clip off somebody else's podcast and newsletter. I'm just making up numbers here. I don't know what it is. Mm-hmm.
But let's say it's twenty-five percent or something. You have to make a lot of money for it to be worthwhile after you factor in the cost of sales and production, right? Mm-hmm.
So you invest a lot of time in getting it up and running, and you may not make any money for a year or two unless they bring their own audience to the table, and then they leave.
Like from a CFO brain, that's not a very good business proposition if you're churning your assets, your revenue generating assets, right? Sure. And so- Well, you just hire them, right?
I've put that in the- Like, I mean, that, that's something... Yeah, you know, you cast someone in the role versus like having someone established.
You're like, "Okay, well this area, you've got, you've got sales guy Matthew out there killing it based on the podcast I just listened to," right? Yeah. And you're like, "Okay, we've got excess demand.
Let's push this demand into new categories. Let's create even, an even more specialized, you know, an FP&A..." You have to tell me what FP&A is. Financial planning and analysis. Okay. The budget people.
[chuckles] Okay, there, there you go. We're gonna create an FP&A like sub-brand- Yeah... and you can own... You know, you've got people that you can like push into that, and we're gonna cast someone in, in that seat.
You're gonna-- We're gonna put someone in the seat. Yeah. And I, I think this is the hardest part for me to get my brain around. I think part of what makes it special is- Yeah... the scarcity. Right.
That I, that I could do so much more- Totally... and I could make more money, but I've said no to a lot of things. And I think there are way too many stories of people... It's so hard.
It's like Odysseus, you gotta strap them to the mast of the boat- Sure. [chuckles]... rather than just- The sirens. The siren call. Yeah. Yeah.
The siren calls of being able to be like, "Well, we said no to that advertiser. We could put it on this lower profile one over here." So I'm trying to stay away from that.
So I've put that in, in the hard pile of getting... People are messy also, so putting that in the hard pile. Another thing I've put in the hard pile is-Investing other people's money.
I don't like-- I don't wanna create a fund. I don't think I'm uniquely qualified to pick the companies. Oh, interesting. I'll do some angel investing on my own maybe, but, like, that's still not the main thing.
And I think, like, a community is also something where you're playing on hard, 'cause if you have a-- if you convince 100 people to shell out $1,000, which is-- it-- that's a, a considered purchase to give somebody $1,000, it's still only $100,000 per year business.
So you're looking at what's the marginal amount of dollars I can make per hour of work, and what's the scalability of it. So those are, like, the three things that I've put in the too hard for now pile.
So I don't have a great answer of, like... And that, that's kinda what makes it special, right?
That's why I'm doing it too, because I'm not showing up every day and doing the same thing, and tomorrow I could, I could decide to do something a bit different. So how do you decide what you do and what you do not do?
I mean, one of the things that I, I was struck with, and I've struggled with this a lot, is on sales. Yeah. Right?
And I've tried a whole bunch of different approaches to, to sales, and I think this is n-natural to any of these kinds of businesses where there's so much leverage in talking to the chef, you know.
Like, you've got competit- Th- Everyone has choices out there, right? And you're going up against mechanized restaurants and, you know, the, the chef is on, you know, name on the door, but isn't anywhere to be seen.
And there's leverage, and you've recognized that very quickly.
And some people, like for instance, Acquired, you know, I was really surprised where they said they still handle-- They, they, they basically do all the sales themselves, and that's a- Yeah... pretty sizable enterprise.
But their model is such that that makes sense, right?
And you've talked about this, and I, I, I thought you had m-made a really interesting point, 'cause it's one that resonated with me, is that sometimes you need, sometimes you need a buffer to keep, keep you from, like, harming yourself.
It, it- Oh, it's the biggest hack.
'Cause I was listening to the Acquired podcast too, and they were rattling off some other stuff, like, "We'll come and speak at this event, and we won't charge you, and we'll do this or that."
And I would never throw stones at them because, like, they're the, you know, put them on the Mount Rushmore. But if you have a buffer in between, it can force people... Like, I'm a people pleaser at heart.
Like, I know people think CFOs are, like, they just wanna say no to everything, but I actually wanna say yes to more stuff. Yeah.
And having a buffer in between, you get to play the good guy with everybody, and you just say- That's it... "No, no, no, no. D- buy the newsletter and podcast. We'll talk about the other stuff later."
'Cause otherwise you end up with this bill of goods. It's, like, 17 different things. You're, like, dancing at their kid's birthday party. You're, you know- I know this DJ...
doing, like, this weird HostRed ad where the other perso- like, the founder's on it, and you just sign up for unnatural things that aren't scalable.
And having the buffer has allowed me to make the sales motion more scalable. Right.
And that was something that came out of that Acquired episode, 'cause they talked about the Costco one that they did, the, the case study they did. And, and Costco has-- They have a limited number of SKUs.
Like a th- Four thousand SKUs versus 60,000 of Walmart. Right. And I think what I've noticed in, particularly in media businesses that as you're always chasing revenue in most media businesses, right?
And there's always... I-if there's, if there's any sort of the siren call of media, it's incremental. There's always this siren call of incremental revenue.
And particularly- But it cheapens, it cheapens the main thing when you do that too often. So yeah, you can- Yeah... be like, "You know what? I'll go speak at something for X amount this time around." Yeah.
What I found is better, and I stole this from Prof G, is you only have two prices: fucking expensive and free.
And there's no shame in going to the free bucket because it shows that you really value their partnership, and you will go above and beyond for them, and you wanna be there for, for them, and you actually enjoy working together.
And I do a lot of stuff that's free, and I don't charge them for it- Right... because I think that's healthy for the long term of it. It's not, "You know what? That's $5 over there if I-" Right.
This is the sales versus partnerships, honestly. Because a lot of...
This is no shade at my s- my sales brethren, because I, I respect and honor salespeople because they're good at, at stuff that I'm absolutely not good at, and I will admit that.
That said, I, I have noticed a tendency throughout my career in a lot of sales to wanna chop up everything, to wanna create new SKUs, to create, I wanna create custom SKUs. I remember early in my career being, like...
Or, uh, at, I, when I was editor, like, being, like, handed this, like, "Oh yeah, we sold this, like, you know, Cocoa Break sponsorship at the event." I'm like, [chuckles] "What's a Cocoa Break?
What are you talking about? What is a Cocoa Break?" [laughs] Yeah. Or, you know, the salesperson had, like, you know, roller skated away at that point.
[laughs] Sort of left me, left me with a deliverable of a Cocoa Break, and I... [laughs] And so it's really easy to get pulled into having s- the, the 60,000 SKUs.
Some of it too is just, I don't-- I try not to do anything that I get, like, the ick from. And in the business I'm in, the hardest part for me is, like, finding the line that you're comfortable of going up to. Yeah.
And, like, you're staying below it in terms of... 'Cause y-you do have to do self-promotion, and I hate it. I hate that part. I hate some of the, like- Really? You're good at it, I think.
Well, I h- I hope because it comes across as genuine. Like, I'm not out there just sh-showing LinkedIn posts of you should buy this or that or- Time for a thread. Yeah. Time, time for a thread. People still doing that?
Like, I don't do any of that stuff because I think it cheapens everything else you do and makes- Yeah... it look more transactional. No, I agree with that. I'm terrible at the self-promotion stuff myself.
I have to get better at it. I'm going to get better at it in 2026. I promise. All right, cool. Are there any other topics we didn't discuss? This has been a long one, but I, I, I'm, I'm always- This is fun...
I'm very impressed with how, how you- Thanks, man... how you've built this. And, you know, I, I think, as I said, there's, there's so many different directions that you can go with it.
And I think I really admire when people are disciplined and thoughtful about the type of business that they wanna create and, and it intersects with the kind of life they, they wanna live too.And I think that's different in these kinds of businesses because you can't...
You know, like, you can't separate the two. You're like- You can't. You can't. And the, and the biggest-- So, like, what people may not know about me is I've always had some sort of side hustle, and I've actually...
Like, people say, "This is-- this seems like a successful business. How lucky are you?" Like, I've had a lot of things fail.
Like, I had one startup where I plowed over two hundred thousand dollars of my own money into it and, and lost it. And I've tried five or ten other ideas that just didn't pan out.
And it's just so funny that the one that cost no money to get started and has the best margins and is, like, authentically me and something that I enjoy doing.
And I always thought it was such bullshit when people are like, "Find something you love that doesn't feel like work." I'm like, "Dude, that is the worst advice." Like, how...
Everything's always gonna feel like work, and to a degree it does, but it, it was just reflecting back, it's interesting to find the thing that you love, and it was kind of there all along.
But it's also an amalgamation of, like, your experiences along the way, where there were a lot of times that I was working a job and I was like, "I feel like I'm at a dead end here," or, "I'm not enjoying what I'm doing."
But it all kind of informed this thing I find myself doing now that I- Right... I couldn't have predicted. Well, you also...
You talked about, about it not getting bored, like that being the- That's the biggest challenge, man. It really is. Well, again, some people c-call it burnout or something 'cause I think any, in any of these kind of...
I hate the word creator businesses. I don't know what to call them. But, like, the, the risk is that, right? Is that, you know, I would always say it's like, you know, people would want to...
I, I never liked running columnists from, you know, the industry 'cause I'm like, you know, most people, they can write a couple of things. They can't, they can't produce regularly, and they lose interest or...
You know, I think that's what you say about, like, getting, you know, getting bored. And the, the question always becomes like, is there enough, right? Because, like, you know, you can... It-- Like, is there...
Because how many times- You're, you're writing about growth margin... you're doing tactical, right? So I mean, if you draft off the news, right? And that's why I think a lot of...
For instance, when I started writing, it was more like... It was actually more tactical from my experiences, you know, operating these businesses.
And, you know, I find, like, you, you, you end up, like, getting pulled into, like... And I think that's my journalist background, but you end up getting pulled to drafting off, off the news 'cause you're always...
You basically... If you think about, like, say, Ben Thompson, right? I personally...
H-his stuff kinda, like, drives me nuts a lot of times 'cause I'm like, I don't need to c- go down a memory lane to something you wrote in twenty thirteen, like, in paragraph three.
Just as, like, a editor, it offends me. But I know that he has a lot of, of, of fans out there who- I don't know how he remembers that he wrote something. I don't remember half the stuff I wrote. No, I...
That is actually the most impressive thing 'cause I'm like, "Really?" I'm like, "You, you remember what you wrote in twen- twenty thirteen?" Right. "You expect us to, like, care?" But he has a lens.
He has a lens, and then everything that goes past his lens, it's... He just [snaps finger] he takes a photo. He's just- Yep. Yep. You know? And, like, that scales.
That's why he's been able to do this for whatever, fifteen plus years.
If you're saying, "Here are the playbooks, the tactics that you need to be, like, you know, the best, like, finance professional," are you gonna run out? I think you can remix enough stuff that you don't run out.
Oh, yeah. It's a Mex- everything's a Mexican restaurant. Is it a chimichanga? Is it an enchilada? Is it a burrito? Yeah. Is it a burrito or is it, is it a burrito bowl?
And I mean it in a way that you can continue to improve it over time, too, 'cause I was nervous about that.
And I remember Lenny Rachitsky had the advice that he said, "I think about every piece as like a puzzle piece, and I'm trying to fill in this mosaic, but I still reserve the right to come back to a piece, like, let's say it's on, like, net dollar retention for, for me, and, and do it better next time."
Yeah. And then what I also think about is if I'm at seventy thousand subscribers now and I was at, you know, sixty thousand last year- Totally... I mean, there's a lot of people who didn't read it the first time around.
And so- Oh, my god. I used to have these reporters who we would be talking... If any of them are listening, I, I... They still like you overall, but this part drove me nuts. We'd be talking about some...
It's like, "Oh, you know, we, we should do a story about this," and someone would be like... Would always say, "Oh, you know, I mentioned that three months ago in, like, you know, paragraph seven."
I'm like, "Well, I'm the ed-" Nobody remembers. "I'm the editor [chuckles] and I don't remember." Yeah. "So I think we're safe." [laughs] I wrote it and I don't remember. Yeah. So I have to often remind myself of that.
But yeah, I mean, every business will have its challenges, and that's also why it's important for me to talk to the people who read it.
And that's something that, like, if you're doing the Eisenhower Matrix of what is urgent and important versus important but not urgent, like, talking to your readers is something that- Yeah...
is incredibly important, but it's never urgent to, like, set up a meeting or put a Calendly link out there and be like, "Tell me about some metrics you use to, like, run your business."
And so I started doing that and meeting with people, and that's been the most refreshing thing. And they're always like, "Thank you so much for, like, giving me advice."
And I'm like, "No, thank you for, like, re-energizing me and giving me just, like, something to put in my head that maybe I'm taking a shower later," and I'm like, "That's what I'm gonna write about." Okay, final thing.
What are, what are, what are some, like, three media compa- media businesses? They can be, like, you know, newsletters. They can be podcasts.
They can be larger entities that you look at and you're like, "You know, I wanna, I wanna learn or emulate from parts of, of those businesses." Yeah. If I could have dinner with anybody, it would be Scott Galloway. Yeah.
I just love what he's built with his business and his personality and, and how he's, like, vulnerable at times with, like, just figuring stuff out and his failures. So he's definitely out, uh, up there.
But he's also, like, taken that cash flow. He, he's... Beyond that part of it, the business itself of being- He can stand alone... Scott Galloway is pretty amazing. Yeah.
And I mean, like, I'm, I'm, like, a student of the game, so I'm like, "Okay, so how does he distribute his net new podcast? Does he put some of them on the same RSS feed and then- Yeah... break them off as experiments?
What does he do with the co-host? What's the amount of time the co-host is on there?" And so, like, I try to study that type of stuff 'cause there isn't really a playbook written on it. I respect him a lot.
Like I said, I've always been a huge fan of Bill Simmons and what he's built. And then [sighs]
on top of that, I mean, like, there are a lot of other smaller writers that I love to read, and not many people have, have heard of them. Like, my friend Paul Stanzik, he writes Hello Operator.
I think it's a super tactical, you know, newsletter for PE-backed operators. Kyle Harrison writes Investing 101 as an investor.
And so, I mean, like, I, I just try to read a lot of other people because I do think that everybody has, like, at least an hour worth of knowledge that they can impart on you to, to help you in your business. Awesome.
CJ, thanks for doing this. Really appreciate it. Thanks, man. Great hang. [outro music]