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I think like CFOs are always looking to get advice from their peers on what they're using. Like, there's always that old adage that no CFOs ever got fired for buying IBM.

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And so in a lot of ways, they're looking for a voice of a person who isn't just like a company just purely pushing them stuff. They're looking for someone who's been using that technology day in and day out.

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[on-hold music] Welcome to the Rebooting show. I'm Brian Morrissey.

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This is likely the last episode of this show for the summer. I'm hoping the Internet holds out in this little Croatian town I'm in for the next couple of weeks.

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It's called Crojan and has this amazing views, and I just went for an amazing run on a great trail in a place that is called Buje, which I found amusing because it means something totally different in English.

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So likely we'll not have an episode next week or the week after and be back after Labor Day. We'll see how the, uh, Internet goes here.

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You know, last week I wrote a piece in the newsletter titled The Media Business Is Still Hard, and I don't want to get too self-referential in either the newsletter or on this podcast.

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Something I wrote about is how hard it is to keep a bunch of balls in the air and to focus on what's in front of you while also focusing on the long term.

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And one of the things I wanted to express in there, and sometimes it doesn't get through, because I get people who say I'm a curmudgeon or worse, cynical, is that I'm very optimistic about the media business overall, and perhaps less so about repeating the models of the past that prove themselves to be wanting.

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But I'm very optimistic about many new models, and I try to highlight many of those in the show, and I'll continue to do so. And one area I'm very optimistic about is expert-driven micro media brands.

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I don't know what else to call them. Business lends itself to this.

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The ideal is someone who has deep operational knowledge in a field, who can also communicate in a way that can transfer that knowledge and experience to others who might want to join the field or those within it.

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And oh, by the way, they have to be able to do it consistently, and this is unbelievably hard to do.

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I don't think a lot of people recognize how difficult the quote unquote content business is as far as having to do it day in and day out, week in, week out, month in, month out, year after year.

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Because that's really what separates the real professionals from those who are just kind of tourists in it. And in some ways, I'm trying to do that with the Rebooting.

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I mean, many of the issues that I discuss are ones that I've dealt with personally over my career, and it's one reason why I don't quite know what to call myself right now. I don't consider myself a reporter.

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I don't edit anymore. And while journalism isn't, as far as I know, a credentialed field, I'm not sure I'm that either, at least not entirely.

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I mean, after all, I'm selling sponsorships and doing things that the College of Cardinals at J Schools would decide are excommunication level sins. But I don't really care much about that.

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I mean, Ben Smith was nice enough today to give me a shout-out in the Semaphore Media newsletter, and he called me a media analyst. I'll take that. And John Kelly of Puck called me a media salon. So I'm getting there.

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Anyway, my point is, I take an expansive view of media, and I believe companies can create media. Although I wish they'd stop playing pretend with this brand newsroom nonsense.

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And I believe that we're seeing the creation of many of these expert-led brands. And I'm thinking of people like Packy McCormick with Not Boring for business strategists or Lenny Rachitsky for product managers.

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And I think CJ Gustafson, who is my guest on this edition, is in this group.

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[on-hold music] CJ is a CFO by day and by night, he transforms into the proprietor of Mostly Metrics, which is the handbook for both CFOs and would-be CFOs. I mean, you should check it out. It's mostlymetrics.com.

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I wanted to have on CJ for a couple of reasons. One is he's one of the rare people who is both immersed in his field but does not suffer from the tyranny of knowledge.

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And the tyranny of knowledge is when someone with expertise can't communicate that expertise without lapsing into jargon or assuming a level of understanding that's not broadly shared.

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Anyone who has spoken to developers has run across this affliction. CJ uses memes in a conversational style with Mostly Metrics to address what those outside of corporate finance would consider very dry topics.

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Which is another reason I wanted to talk to CJ. I wanted to get his take on why the media business is often a terrible business, and how to think of the financial side of the business, because it is critical.

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I've always found it strange that in two decades of covering this business, I rarely spoke to CFOs, and a good CFO can transform a business.

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My own understanding of the financial aspects of the media business is probably one of my weakest areas. I end up on Investopedia all the time because I'm googling things like contribution margin.

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I want to try out something. I'm gonna start in September on the Rebooting, where I get into the weeds of specific functions of operating a sustainable media business.

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That will mean narrowing in on what I think of as the mechanics of the business.

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So instead of operating on the more strategic level, which is probably generously where I mostly write and talk, but getting into the weeds of issues like CAC and LTV and churn mitigation and figuring out sales compensation plans and more.

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I find that as I look to build the Rebooting as its own micro media business, I have to immerse myself in all kinds of areas that are mostly new to me.

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And I've found that over the years that these kind of tactical discussions are in many ways the most valuable ones. So I hope you enjoy this conversation. And one quick note related to the business stuff.

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The Rebooting is doing its first research project.

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It's a collaboration with Video Elephant, and we're running a survey that is basically about how publishers are feeling about their video businesses and where they see opportunities and challenges.

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I'm gonna take the results and with the help from Next to Media's Mike Shields, my former colleague, turn it into a research report that we will then distribute through the Rebooting.

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The survey takes only a few minutes, and it is not one of those surveys that's like a push poll that's really a marketing exercise. This is a genuine attempt to get a read on the state of the market.

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I hope to do more of these in different areas. So this is the first one, but hopefully the first of many. You can find a link to the survey on therebooting.com. Just go to the latest edition of the newsletter.

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Thanks so much. Here's my conversation with CJ.All right, CJ, welcome to the podcast. Thanks for having me on, Brian. I don't get invited to these media parties often, so thanks for having a CFO on.

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That is very true, CJ, because, you know, the finance is often f- for some reason overlooked in talking about these sustainable media businesses. Right. So I wanna do, like, basically a two-part episode.

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One, in which you sort of walk me through, like, finance one-on-one, because I know there are a lot of people out there who they might know some of the terms and stuff like this, but I've seen it up close, and they're at the top of these companies, like, they don't really get the finance part.

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And that is, you know, the defining factor about whether you're gonna have a sustainable business. The good CFO changes the trajectory of the business.

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So give us just a real quick, and then we're gonna do mostly metrics- Yeah... and what you're doing with it. But you're the CFO right now at PartsTech.

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What is your sort of background and experience, just very in a capsule? Yeah, sure.

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So with startup businesses, you can be the one who funds it or you can be the one who accepts the money and then runs the company, and I've kind of been on both sides of the table.

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So I started off on the funding side, and then I moved over to the funded.

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So now I'm a CFO at a venture backed startup, and, you know, I'm trying to make capital allocation decisions for us to hire the right people and grow quickly.

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So being, like, a CFO, like, are you, like, a generalist in that, like, you can go into, like, any business, understand the dynamics? Or how important is it?

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Obviously, you need to understand there are different types of businesses, but- Yeah... you're not, like, a specialist in a type of business. No, I'm not at all.

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I'm actually glad you laid it out that way, 'cause I kinda think about to become a CFO, you kinda gotta get, like, stamps on your CFO passport.

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And what I mean by that is you kinda do your time in different parts of the business.

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So, like, I've been on the sales ops side, where you figure out what quota you should give to a sales rep to make sure the business can cover its expenses.

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I've done treasury, where I figured how to set up, you know, international bank accounts. I've done FP&A, and this is probably like if I was a specialist, it would probably be more on the FP&A side.

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That's financial planning and analysis. Wait, what is, what is that? I do the ad tech acronyms. I don't do the FP&A acronyms. Those are the budget guys, so basically figuring out- Okay...

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how much you can spend, how many people you can hire.

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But at the end of the day, I think, like, a CFO is really someone who has a mind for, like, how do I get the best performance out of the company, and how do I apply numbers to that to solve the problem?

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So you've seen a lot of different types of businesses, right? Yeah. And it seems particularly we're coming out of an era in which it was all about SaaS businesses.

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Like, the SaaS business model is a great business model, right? Yeah. And explain for those, 'cause I think media is realizing some of the flaws of the typical media business model.

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Why, like, you know, from maybe twenty-five thousand feet, not thirty-five thousand feet, why is the SaaS model so powerful? SaaS is really powerful because of its recurring nature.

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So, like, I like to make the analogy of SaaS as kinda like a snowball that's rolling down a hill, and it's accumulating more and more snow.

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So you have, like, this base that you can get revenue out of in a predictable manner every period, and as long as you keep adding more snow to that faster than it melts, your business is gonna grow over time.

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And that makes it easier to make decisions around, hey, how many people can I hire? How much do I think I'm gonna grow?

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Because you kinda have a lot of the, what I call the fish in the boat in terms of what's gonna be billable in the next period. And so that's why people like SaaS businesses. Yeah. And it's...

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I think, you know, venture capitalists love, they love the SaaS dynamics, and that's why there have been so many...

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It's funny 'cause, like, I can remember, you know, when I first started covering these businesses, it was all consumer tech really, and B2B was a backwater to some degree. And anyone who worked in...

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You're a little younger, but, like, [chuckles] you know, the technology that you had, like, at work was...

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O-originally, it was, like, better than you had at home 'cause you didn't have the internet or anything like that. That's why there was Cyber Monday and whatnot.

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But then it was quickly, it was like, oh, my God, why are you making me use Concur? And because a lot of these systems were just, like, ancient and awful.

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And so then the consumerization of B2B got funded, and you-- I, I think you tweeted the other day, like, you know, Expensify. I mean, this is something, like... I remember when we started using Expensify, I was like...

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I actually gave our CFO, Steven, I gave him, like, these pretzel rod, his own, like, pretzel rods because he switched it from Concur to... I awarded him this [chuckles] 'cause he switched- Poor guy...

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from Concur to Expensify. Yeah, forward-thinking. It was meant to be a symbolic award, but then the next CFO switched us back to, like, NetSuite or something terrible. Every CFO switches, yeah.

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But a good example of you have tremendous leverage in that business model, and I think that seems to be, like, a really important part of finance.

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Like, how do you determine-- how do you figure out the leverage in your model? It's a great question. I actually think about this too much, and I think that there are two different types of leverage to kinda look at.

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Well, it's cost leverage and then revenue leverage. So the first is the ability to get more from each incremental dollar that you spend.

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So, for example, you can have economies of scale, they call it, where, you know, after you go through the pains of building all the infrastructure, you pay less per unit sold over that same infrastructure as you go.

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And so Amazon went through the pains of building out a massive logistics network, and now they have economies of scale where they can deliver stuff to you, you know, way cheaper than anybody else.

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But I think another example is in software. You can code the program once. I mean, like, you have to fix it from time to time, but then you can sell it a million times over.

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You basically have zero marginal cost of production for each unit. That's like-- that's why software leverage is really, you know, attractive for VCs to invest in. Yeah.

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And so if you were to, like, sort of rank, and I don't know if you could do this, like, the types of business models, like, from, like, most attractiveTo like least attractive.

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I mean, you can just choose, there's tons of different business models, but just like if you could choose like a few, like we'll start with like most attractive and then get to least attractive, which I think is where most like publishing businesses are.

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Yeah. I can definitely do that. I'll try to do it right now. So I think subscription revenue is probably the most attractive, you know, where you pay on a monthly or annualized basis. That's like your Zoom license.

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It could be Notion, it could be Adobe, it could be your gym membership, really, it could be your New York Times membership.

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Then I think the second most attractive is usage-based, and that's, you know, the taxi meter that's running in the background. It's less predictable- Yeah.

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-but, you know, you can get the cost up pretty high depending on how much usage is used, if it's aligned to where the customer gets value out of it. So that could be like Twilio, where you know, you send text messages.

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It could be AWS for your hosting, it could be, you know, your Uber. So those are like two of the more attractive ones. Then you have transactional revenue. So that's...

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This business model is, you know, based on a take rate or, you know- Yeah... interchange. So you could think like Stripe is an example of that. Airbnb takes a cut or vig of every transaction- Mm-hmm... it goes through.

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Substack and Patreon are like two easy examples of the transactional revenue. Yeah. And I-I'll just jump in.

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Advertising technology really is one of these business models because they step in between a transaction and take a small cut off that.

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And, you know, that's why these businesses are valued so much greater than, for instance, the publishers that are creating the content that the advertising is, ends up on. So the intermediary is more valuable- Yes...

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than, you know, the end. You nailed it. And that takes me into the other two types of revenue where I believe, you know, media is traditionally set, and that's advertising revenue.

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So that's either per ad or per search or per action. So like Snapchat does that, LinkedIn does that. And then you have one-off revenue. So that could be events or e-commerce or, you know, consulting- Mm. -type stuff.

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But that's with the services? Services at the bottom. I personally believe services is towards the bottom because there's less leverage in that model, like we discussed.

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Like you're always kind of on a treadmill to produce more, to get paid more, and you can't like sell the same thing, you know, over and over again.

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If you're in the business of, you know, doing like a whale watch tour or something, that's services. Like you, you lose that seat if the boat goes out without somebody in it, you never get that revenue back.

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And you also have to get on that boat every day and take people out. So there's not much leverage in that service. Yeah, tell me about it. I know all about this.

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[laughs] I love all my partners, but like, you know, that is where media exists, and I think there are exceptions to that when you have different leverage when platforms do, when it comes to their advertising businesses.

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A lot of them, not necessarily, Snap's kind of screwed up in a few different ways. But, you know, a company like Google, you know, [laughs] they paid a ton to create a search engine, okay? And they maintain it.

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And they also, by the way, paid a ton to mop up the entire distribution, lock in all the distribution, which the DOJ and other attorneys general are, you know, squawking about and taking them to court over.

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But once you have that dominant position, you know, I always say like Google's ads business in some ways is more reminiscent of like owning a parking lot or they own the highway and they start taking a toll at the end of the day.

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Because if you're, if you operate on the internet, you are paying Google. You are absolutely paying them. You must. And that's just how it is. That's a tax. I don't know where that fits.

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There's actually- It's a good business. There's actually a joke in like my world that, you know, forty percent of all funding dollars just go right back to Google AdWords. Yeah.

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[upbeat music] Yeah.

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And by the way, a lot of this AI and, you know, the business models are still unclear about AI, but, you know, the big tech companies can't necessarily make these giant acquisitions.

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So what they're doing is it's like a total round tripping, is they're putting money like, you know, Microsoft put whatever, a billion dollars or something into OpenAI, but a lot of that money's coming right back to Microsoft th- because OpenAI has to buy the compute somewhere.

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And so i-it's a way of controlling the company without necessarily, you know, getting entangled with the FTC.

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So basically, media is a terrible business because they [laughs] because it relies disproportionately on advertising and services revenue. Is that the long and short of it? Yeah, I think it is.

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And there's one other kind of leverage, and that's on the revenue side. And that's, you know, you wanna go out and pay to acquire a customer once and then stack multiple revenue streams on top of that customer.

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So I think people also like software businesses because they can upsell and cross-sell additional products.

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And media businesses traditionally, you know, you can sell them one subscription, but it's pretty damn hard to sell that same person seven different subscriptions to other stuff. Yeah.

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Although The New York Times is, you know, I think it's an interesting example of...

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And it might be-- and unfortunately, The New York Times is always the example used because it is probably an exception to the norm, right?

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Uh, of being able to make that pivot from an advertising business with services to a subscription business, and now they have a bundle of subscriptions. And I think one of the issues is TAM, right?

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Like, what is your total addressable market?

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And the total addressable market for news subscriptions, I remember when they first did their subscription, I was doing a podcast with Meredith Levine, the CEO, and I'm like, "There's not that many people who are gonna take out a New York Times subscription."

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And like, you're not gonna... Like Netflix, it's like everyone watches TV. Like that is a, that's a massive-TAM, but like yours is very small.

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And now, well, now they're into games, now they're into food, now they've got The Athletic, which is kinda news, but it's really different.

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And, you know, that's because the ne-news as an addressable market is not as big as a lot of people sort of think. At least for, you know, there's half the country that would never get the New York Times subscription.

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They just won't. It's true. I don't have a New York Times subscription, but I have probably ten subscriptions to more niche news outlets that are, you know, about finance or about business or about a specific sport.

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Like, I'm a big fan of track and field, and I, you know, I don't have, like, an ESPN subscription, but, you know, I read The Lap Count on Substack, so that, that's an example of one I think that I pay for. Yeah.

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But I think it's interesting to, particularly for media, when you talk about, like, niche and is understanding that addressable market, right? Do you...

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Explain, like, why it, that's important because I think a lot of time, at least when people are talking about it, they're not focused on...

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You know, in, in Silicon Valley, it's like, well, they just go for the biggest TAMs, it seems like, for the most part. [chuckles] They'd rather have a small part of a massive market than a big part of a tiny market.

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Yeah. I mean, your TAM is essentially your runway of how many customers you can sell into, and I'm a big TAM nerd.

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I mean, like, I can't walk into, like, a bakery in Boston without, like, trying to calculate the TAM for blueberry muffins, like, in the area and how many they need to sell to, to stay in business.

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And my wife doesn't really like to hear me rant about it.

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But nonetheless, in any business, you wanna figure out what your TAM is because you're creating a product that, you know, you're trying to sell to a specific niche of people.

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And when you have a smaller TAM, you have to eventually add more products, or else you're gonna run out of people to sell it to.

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And I think at the core of any TAM conversation is basically, like, a per unit, you know, cost or revenue multiplied the number of people or users that are out there.

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So you can have what's called a bottoms-up TAM, and that's when you're actually doing the math of, hey, you know, there are, you know, seven thousand people in New York, and I think that they'd each pay seven bucks for this subscription, and it costs me five bucks to make.

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And then you can do the top-down ones, which, you know, companies like Gartner and Forrester are famous for just telling you how big it is. Yeah. Those are [chuckles] more qualitative measures sometimes. But what is it?

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The... If you torture the data long enough, it will confess.

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Which is something that also I think we've all, anyone who's been in this business, I assume in any business they've seen this, is like, particularly when forecasts are being made.

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My favorite was forecasts that I'm like, there's a difference between a forecast and a goal.

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And just because you're setting, like, a goal for the sales team, which by the way is never the actual goal because it's like, it, it's always just set, and I'm like, "We're not, like, managing to this goal, right?

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We have a different one, right?" Like, let's not present this as a forecast- Brian, that's our finance secret... because it's the goal. You can't reveal that to the public.

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Like, I thought that people didn't know that there was, you know, a board plan and then an operating goal. I was like that the sales team would be told, "This is our forecast for the year."

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And it's like, oh, no, we're not spending to that, like, forecast versus the... We'll, we'll come in like totally two million there, three million below that. But, you know, gotta incentivize.

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What are the, what are the most important metrics when you would be, like, looking at, let's say, a media business, right?

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If someone came to you and was like, you know, "Analyze this media business," what would be the most important metrics you would look at to understand its sustainability, financial health? Yeah.

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I think I would look at how much revenue I can generate per employee that I have there, so basically revenue per head, and that's like the easiest top-line check I would do.

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Then I would look at my average revenue per customer or user to see if that's growing over time, and that's by either selling them more stuff or, you know, they're using it more and, and increasing over time.

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And like the, you know, north star here is to increase your lifetime value, and that's how much you get from a customer for as long as you have them over time.

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And what you wanna do is flex that against your customer acquisition cost, and that's what you spent in sales and marketing dollars to initially get them.

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And so, like, a quick rule of thumb is that you want your lifetime value versus your customer acquisition cost to be more than three X.

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And I think media businesses traditionally get caught in what I call the LTV to CAC kinda death trap, where you have to- Yeah... pay a lot to get a customer, but then they churn out or they don't spend enough over time.

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Yeah.

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And also, I think one of the challenges is the CACs can fluctuate, like, quite a bit, the cost for ac-acquisition costs, because, you know, we see this a lot, like, with the first generation of newsletters and even newsletters now really.

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A lot of people are spending a lot to acquire customers, and the DTC business, DTC e-commerce business to me was sort of indicative to that in that the, these businesses only worked with artificially low CACs.

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Like- Right. Right... it was kind of like these, the tech businesses that literally could only exist in a zero interest rate phenomenon, and then everyone was crying when interest rates weren't zero.

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And it's like, well, of course, they're not always gonna be zero. Like, you can't blame Jerome Powell for this. This is, like, history.

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And if your business can only exist when interest rates are zero or the cost of acquiring a customer through Facebook is, like, instantaneous and really cheap, well, you're at risk.

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And I think a lot of these DTC businesses turned out to be even worse businesses than publishing businesses. Yeah. You know?

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I think there was this Zurp phenomenon where people were able to, you know, put a dollar out into the ads ecosystem and get five dollars worth of customers back, and that just doesn't exist anymore.

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That's gone away.Yeah. So one of the other sort of the keys to growing any business, but I think, you know, the media business has been through this, is how do you finance growth, right?

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And a lot of media businesses, not a lot of media businesses, but there was this brief period of time in which media businesses were raising venture capital and loading on debt.

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And we saw this with Vice, we've seen this, you know, with BuzzFeed, we've seen this with others, and it didn't work out at all. I mean, is... Are most particular...

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Just leave aside media, most publishing businesses, they're not made for this way of financing growth, it seems like.

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I think that Lenny Rachitsky did a really great article on this, Lenny's newsletter, about, like, how not every business needs to necessarily be venture backable, and that's okay.

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I think, you know, the venture backed way of doing things is based on a power law of, you know, one out of twenty things works out, and that's not always the healthiest way to grow a business, especially the news business, where you're not able to just throw a lump sum of money at a market and gobble up users as quickly.

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In fact, you may actually do yourself a disservice and burn through that TAM or burn through that market by going at it, you know, not as thoughtfully.

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But I think, like, when I, you know, sit back and look at how to finance business growth, y-you're either funding the people who are building the product, the people who are selling the product, or the people like me on the finance side, who are really helping those people do what they do better.

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And, you know, when I think about the media business from this perspective, the easiest example is to think about financing a writer, which is kind of like a widget that, you know, has a cost a-attached to it and a revenue, you know, hopefully attached to it over time.

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Okay, wait a second. Wait, wait a second. Yeah. You're calling me a widget. I don't like this. Back in the finance office. Get... [laughs] Yeah, get back in your Excel spreadsheets.

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[upbeat music] You, you think about, you know, each person as a unit that ramps up over time to produce revenue.

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Maybe they're producing, you know, two podcasts for you a week that make X dollars and one newsletter which makes Y dollars.

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And you can basically forecast out, you know, how I finance the amount of people I hire over time based on what their run rate productivity will be and how much money they can bring into the business.

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It's funny 'cause, like, I was always against this sort of unit economics approach to publishing, at least in the companies I was at, because people were contributing different... For instance, with subscriptions.

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Business Insider was across the hallway, and they approached their subscription product as pure unit economics. Like, how many subscriptions did each writer produce? Okay.

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'Cause everyone wants to know the productivity of their employees. And employees should want it, because if you're more productive, you should make more money, et cetera, et cetera.

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The problem is, people subscribe to a bundle, and it's really hard to understand who contributed to that decision for someone to take out a subscription. And so you end- Attribution's hard. Yeah.

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Because, like, just the same way as, like, Google would always get, you know, too much credit because they were at the bottom, you know, right before the transaction- Yeah...

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even though they didn't create the demand in a lot of cases. You gotta show up good on the spreadsheet, basically, CJ. That's basically what I've learned.

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I think it's putting yourself in the way of the money in a lot of aspects to show that attribution.

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I love how you used Google as the example, 'cause that's, like, something, like me working at tech companies, we've always struggled to figure out, like, what was not Google, 'cause it always feels like Google's taking credit at the end of the day because they're in the way of the money and right before the transaction goes down.

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So that, that was a good example. Yeah. I mean, like, I... A lot of...

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I covered search early on, and, you know, they had to decide early on whether they were gonna allow competitors to buy trademark terms, and it was controversial. It was legally vague at the time. And, you know, the...

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They were just like, "Oh, we're just gonna lawyer up and fight this," because there's too much money to selling Best Buy the Best Buy search term. [laughs] Like, you're not... There is no value being created.

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Someone is typing in Best Buy and you're putting a Best Buy ad. [laughs] You do not need, you do not need rocket science to execute on that. I mean, it's just a tax. And, you know, companies pay the tax. It's fine.

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You operate on the internet, you- Yeah, it's a tax you pay to play the game at the end of the day. Yeah. I kinda want that. I would... I say, like, maybe the analog version would be, like, owning a parking lot.

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I always thought, like, owning a parking lot's a great business because, like, the only thing you really need to do is just make sure that the people, you know, the, the, the kids or whatever who are collecting the money aren't stealing too much from you.

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I mean, 'cause otherwise, like, w- I don't know. You, you don't really need to do anything. You just have a parking lot. And, you know, you just have- Yeah... a few people taking the money.

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It's probably the best business model that's out there. It's one of the best business models, CJ. Yeah.

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Okay, let's talk a little bit about, about Mostly Metrics and why you started writing about this, because I think one of the things that I've noticed with the newsletter world, I'm thinking about writing about this actually later this week, is I think there, there's, like, a few different sides to it.

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There's, like, the hustle side to me, and there's, like, a lot of people who are really good at finding seams, I guess, in distribution, and they're generally younger, and they're more, like, general and, like, one,

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one month they're writing about, like, Chrome hacks and the next they're AI experts or crypto [laughs] experts and-Rinse and repeat. And I'm not very bullish on that side of the business.

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And then there's this sort of journalist refugee side, which I'm probably part of it, but then I think the part that I'm really interested in, I think it's hard to like pull off, are those that have deep expertise in areas like you do, but are also able to consistently write and explain and communicate engagingly and effectively about it.

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And that's, you know, that combination is pretty rare. I think it's more rare than people think. So what made you- Yeah. -sort of start Mostly Metrics? So I am a finance person.

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It's kinda weird for a finance person to enjoy writing, but I write Mostly Metrics, which is a newsletter about financial metrics and business models and company performance.

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And my audience is mostly tech CFOs and people who work in finance, strategy, and operations at those tech companies.

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So, you know, all those people we were joking about that we stick in a back room, and you don't get to see that much, but we're pulling up on about thirty-five thousand subscribers or nerds like me, and I think like I started it because it was my playground to try out different business concepts I was learning.

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I was working at a hypergrowth startup, helping them raise money, helping them, you know, give salespeople quota and, you know, the best way for me to learn it was to actually try to explain it again in my own words.

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So I did that, and then it was also my way to document, you know, different concepts.

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So like in a couple years, if I did become a CFO, which I ended up, you know, getting into that seat, I could have it to rely on and look back on.

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It would be a playbook of sorts because, you know, where I work, people get hired if they have a playbook to help your company get to the next level.

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And the third piece, which is probably the most critically important, at least to me personally, is that it was my way to kinda write myself into rooms that I couldn't get into otherwise.

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And what I mean by that is like, I think of the Internet as a cool place where, you know, if you start posting stuff that's like somewhat intelligent and written in a compelling voice or a different voice than people are used to seeing or hearing, it, you know, it's kinda magnetic.

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You know, people find each other who talk about similar things, and as a result, you get to talk to people with more experience than yourself and learn from them.

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So it's accelerated my career and I think my learning curve. Okay. So how are you... I mean, it's, is it still like a side hustle? It's a side hustle. It is, but I'm making money off it, which is kinda cool now.

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I mean, I did go paid- Which is amazing -on Substack and... Yeah.

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And [chuckles] I have to give you actually a lot of credit because when we talked last, I was bouncing around like what I was gonna charge for advertising.

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So like, I have paid subscribers, you know, in, in the low single digit conversion off of, you know, my, you know, total free subscribers, which is awesome. Like, I love the subscription business model.

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But when I was talking to you, you were like, "Well, why don't you also do like one newsletter per week that's free and you do advertising?"

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And like, I'm the business model person, and you were kinda like, "Why don't you have all the business models?" I was like, "Hell yeah, that's a great idea."

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So I started doing that as well, and like what I've stumbled into- That's my experience in media, it's like if there's a dollar somewhere, run, don't walk. [laughs] That's generally, that's the econometric approach.

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But I was like describing who my audience was to you, and you were like, "CJ, I think there's a dollar over there you should pick up." I was like, "Okay, cool." Exactly.

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But what I did stumble into is that, like my audience is decision-makers at startups who have budgets, and I just kinda wanna riff for a second on what you'd said before about like the different types of newsletters that are out there.

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Yeah. Because like in my mind, I think there are like four, and I'll kinda tell you how I ended up in, in this spot.

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But like at the base, you have like social commentary, which is just like, you know, maybe it's humor, maybe it's just interest.

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Then the next level, you have news or aggregation, which I think that's what all those AI newsletters are at least trying to do, which is just scraping together stuff- Yeah, they're aggregation -that people can read.

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Yeah. Yeah, like they're not coming up with, like they're not coming up with something that's novel. They're just, you know, bringing it together.

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And then you have in the third bucket, stuff that makes people better at their jobs with tactical and specific advice.

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So like maybe that would be a newsletter that shows you how to invest in rental properties and make money.

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But like what I was able to carve out is this fourth bucket, and that's, you know, stuff that's highly specific to help people make more money at their jobs.

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But what's nice about it is that their company will often foot the bill for it.

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And I think that's kinda in the space in where Lenny's newsletter or the Pragmatic Engineer or now, you know, Mostly Metrics kinda tries to situate itself. Yeah, I mean, that's always, like I used to call it like OPM.

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Are you down with OPM? Like other people's money. And that's why business c-class a-airlines [chuckles] or business class tickets are so expensive because people are like, "Yeah, okay, whatever.

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Three thousand dollars to fly to Cincinnati? Sounds good."

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Because if it's other people's money, they're less price sensitive, which is why Bloomberg is as expensive as Bloomberg is because- Yeah...the people are not price sensitive.

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So no, it's a great area, and I always thought like, you know, to reach CFOs, 'cause CFOs make...

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I mean, obviously they're a very valuable demographic, and people will tell you, "Oh, you need a sales kit with how much money they make." I'm like, "You don't need that.

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You need to know if they make technology buying decisions." And like, just like Steven Roella got in Expensify and then Jo-John Sow. I like John Sow, but I, we disagreed about this NetSuite business.

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And, you know, he swapped in NetSuite, and that's a very valuable audience because the CFOs are making a ton of spending decisions, you know, indirectly and directly because you need software to run these businesses.

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You do. [upbeat music] I think like CFOs are always looking to get advice from their peers on what they're using. Like, there's always that old adage that like nobody's, no CFO's ever got fired for buying IBM.

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And so in a lot of ways, they're looking for a voice of a person who isn't just like a company just purely pushing them stuff.

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They're looking for someone who's been using that technology day in and day out, and that's kinda where I found my niche as someone who is of that world and writing about what he's doing day to day.Yeah, and I think that is like key because, I mean, it's no offense to actually know some of the people over at cfo.com.

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Now they're owned by Industry Dive, which has done a tremendous job for media business. But yeah- Yeah.

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It's totally different when someone has sat in the seat, is writing about it, then look, there's different ways and people bring different types of value, but it's totally different when, you know, you have that sort of peer level, and I think that is a, a really interesting a-and vibrant area to grow.

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I think the... In some ways it's very difficult to pull off because not many people can do both. You know [chuckles] there's... And it's just like y-you mentioned like Lenny Rachitsky.

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I think, you know, you know, he's a great example.

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I don't know him, but like he's a great example of someone who, you know, I think for other peop- some people will be like, "Oh, well, there's like so many other product people who are so much better at product or something."

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I have no idea. Maybe he's the best in the world. He doesn't have to be necessarily the best in the world. Like, what he's really good at is he's able to understand and have that- Yes.

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-like empathy, but like the expertise, and he's really good at being able to create compelling content, and that combination is rare. Very rare.

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It's totally rare, and it brings me back to like this quote that Scott Adams had, the creator of Dilbert, and he said like, "You know, I'm not the best writer in the world, but like I'm probably in the eightieth percentile.

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I'm not the best artist in the world, but I'm probably like, you know, the eighty-fifth percentile, and like I'm not like the funniest person out there, but like I'm pretty damn funny."

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And like I kinda think about myself in, in, in a similar way. Like I'm probably not the best CFO in the world, and in fact I'm, you know, pretty new to the role, but like I, I do it day to day.

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I'm probably not the best writer in the world, but I enjoy it and like it's something that, you know, I try to get better at.

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And I'm probably not, you know, the best business-minded person to run a media company, but I understand some media stuff and enough to be dangerous. And if I stack those together, it's kinda like a killer combination.

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And I think people like Lenny have carved out a niche because, like you said, they also have empathy when they go about doing it and understand like what the audience wants to read because they've been in those shoes.

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Yeah. And I think the other thing is like understanding whether you have the community or the audience. And there, there's both types, you know.

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And look, I think community gets thrown around a lot, but if you can like put yourself in the center of like a group of people, particularly a group of people within businesses that often don't have the excuses to

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get together with each other, it is... And I know events have a different... You left a comment. Like th-there's a lot of drawbacks to events. You know, you have to keep putting them on.

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It's a total treadmill, but the margins are very good, let me tell you. If you do them well, they're very good. But, you know, that is tremendous leverage.

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Like I just remember, you know, someone like for instance in a publishing company like ad ops people, right? Like ad ops people, they wanna nerd out about ad ops with o-other ad ops people.

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And like, you know, the businesses that serve, you know, the place I used to be in some ways served like the ad ops community is... And it is a community. Like people love to talk ad ops.

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It's a good place to be, you know, and I'm sure CFOs are the same.

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I think, I think it is, and there have been a couple of communities that I think writers have, you know, put themselves in the middle of and then created cool businesses on the back of it.

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And funny enough, like a lot of them are backed by The Chernin Group who found them. But I mean like- Yeah. -Barstool Sports did it, and then they bolted on betting. Golden Sports card auctions.

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Like I used to be obsessed with baseball cards. I still kinda am.

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I mean, they put that on steroids, and then like if you think about MeatEater or, or Hodinkee, the watch brand, like all of those companies have found a way to use writing and community and then build pretty sustainable businesses on top of them.

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Yeah.

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I mean, 'cause like you probably, you know, the sustainable business model in some ways, there's a bunch of different ones, but one of the, one of the best ones is to be a front for a different business with way better dynamics.

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You know, ideally some kind of commerce business or, you know, data business is amazing. I mean, look at- Yeah. -Bloomberg's like, you know, the example, and obviously it was like, "I wanna be the- Yes.

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-Bloomberg of this." It's like, yeah, me too. Yeah, that'd be great. Like I'd love to have a terminal business.

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But yeah, I mean, that's, you know, media as a, uh, just as a business is challenging, but media is a way to, to attract an audience and to build a connection with an audience that if you can transfer that to a far better business with better business dynamics is a great place to be.

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Yeah, and I think that there are some creators now who are ins-instead of building a product and going looking for customers, which is what most startups do, they build an audience and then figure out what they can sell them, whether that's data or whether it's like a, an event or something.

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And I think media has an amazing opportunity to use the distribution it has as the leverage for- Yeah. -another business instead of just stopping short of just the writing. Yeah.

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I mean, former, uh, a former guest of this show, Adam Ryan, uh, he's at Workweek, and they have a collection of like- Yeah. -creator B2B newsletters, and

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they're doing this with their franchise brand, and they're trying to... Yeah, they've got the distribution, and now they're like, "Okay, and here's a tool to be able to..."

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I, I guess it'll be like a SaaS model to be able to like find new franchise opportunities for something. It's-- Look, if it works, it's amazing.

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I have my doubts about people trying to build technology or media companies. I-- But maybe. I have no idea. I mean, usually it is... Like for instance, like Vice at its best was a front for a production shop, you know?

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And a lot of times media is the front for like a services business, like an agency business, but that's not like... You wanna get at something that's data or, you know, or commerce to some degree. And I think a lot of...

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Chernin clearly follows this thesis. Yeah. And data is kinda, you know, people joke that it's the new oil, but talk about leverage. Like, I mean, y-you don't always have to even build software around it.

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You're just selling somebody like a spreadsheet or something that's very specific to their industry and gives them alpha to whatever they're working on that day.

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Like that's what I find most attractive, like outside of just the writing opportunity that I'm working on now.

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Like there are so many different things within the finance industry that you could potentially sell somebody, whether, you know, it's compensation benchmarking for hiring decisions or, you know, headcount trending data.

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Like these are the things that I think once you're writing about it day to day, these opportunities start to pop up that you would have never seen otherwise. Yeah, exactly. Awesome. CJ, thank you.

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Our internet held out here in Croatia, there in Connecticut. Yeah. This was a lot of fun. Thanks for having me on. I really appreciate it. Okay. And I'm a big fan of your show. Yeah, cool. Thank you. Appreciate it.

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Thanks again, CJ. Thanks. [upbeat music] Thanks for listening. Thank you to Jay Sparks for producing the Rebooting show.

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If you have a podcast that you're considering making, you should check out Podhelp us and what Jay can do for you. Go to podhelp.us.

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