In this episode, I talk with CJ Gustafson, the former CFO behind Mostly Metrics. CJ didn’t come from journalism or media. He came from operating. He started writing to document the playbooks he’d built as a finance executive. That side project turned into a $3 million business with no full-time employees, built around a narrow, high-value audience of CFOs.

We talk about why subscriptions are a useful base but not where the money is in B2B, how sponsorships actually work when sales cycles are long and considered, and why CJ has deliberately avoided becoming an events company. Mostly Metrics is now largely sponsorship-driven, sold out well into the future, and optimized for cash flow and leverage.

Welcome to the Rebooting Show.

I am Brian Morrissey.

I'm gonna kick off this miniseries that I want to 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 niche 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.

And so you want to be that.

CJ's got, over a decade of experience in, in PE m and a and Finance for Startups.

He started writing a newsletter in late 2020, like, many of

us during the newsletter.

Boom.

and he has grown, mostly metrics initially on substack.

I think you, you switched to our friends at Beehive.

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, your city.

I was like, CFOs literally make every spending decision.

They're the most valuable people to be reaching.

And I am really jealous that sometimes I love my media people.

I kind of wish I had, I think I kind of wish my, my audience was your audience.

Sometimes cj.

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?

uh, you can be, I mean, our anonymous, anonymous banker is

like, is is only lightly anonymous.

I'm just

people, most people know it's

I'm a fan of the show.

Obviously.

You can tell.

Awesome.

Well, let's let, let us get into it.

So, you started writing this newsletter, in December, 2020.

You were scratching a itch there.

You know, it's a typical pandemic story, right?

You're like exiled.

I think at the time, maybe in Cape Cod 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 a very long time.

So it was, it was like over two years with just 400 subscribers.

And for context now, you know, we're talking at the tail end of 2025.

I'm at 71,000 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 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 Ky to, to a degree, right?

Like, I don't know if you accept or

Oh yeah.

got a 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 bring practical, real world experience.

You know, annual planning like is something that you have done right.

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-C-F-O at a venture backed company.

I needed to have like these playbooks, and I was just writing it down

online rather than I guess writing it down like in a diary somewhere.

And this was a, initially when you started to get traction,

it was a classic substack, right?

was, I started on substack and I waited until I was at.

10,000 free subscribers to turn paid on.

And I'd confided to you a while back when I was still figuring 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 glamor 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?

Because I mean, you mentioned LTV and, you know, I think subscriptions

are amazing, like it, and it's kind of ironic in some way because.

A lot of your experience for most is, is in SaaS, right?

And

it's all, it's all set 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, 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 dynamics of SaaS businesses are pretty

remarkable outside of Google.

They're like the mo, like one of the most remarkable business models

around at like, they work, right?

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.

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

exactly.

Well, it's the cobbler's sun, you know, never has shoes kind of thing.

Every single, every single lake.

Digital agency I ever, like, covered, always had a horrific website.

So I, you know, 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 agreed to buy a hundred thousand dollars worth

of stuff every single year.

The marginal cost to sell another license to sell to

another company is pretty small.

when you get into the content business, you have to keep.

Producing that content.

So you're kind of on a treadmill?

I, I want a business like Panda Doc 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, what do you, I'm like, what did you do?

Like, what did you like literally, what did you do?

Yeah.

So from, from that perspective, you, 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 kind of 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 a hundred

licenses at once to sell a thousand licenses to JP Morgan or something.

Like, it's really hard to do that with a Substep 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.

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

Everything goes through the CFO.

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 kind of smaller

side, everything starts at call $25,000 per year, but on the higher

side, they're paying hundreds of thousands to million dollar plus

for these products and services.

And so it's very, 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.

What, what I look at is 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.

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 what?

I saw that one ad I want to pay you $250,000 for a new ERP.

It just doesn't work that

Let me rip out the A-R-P-I-I-I I've seen enough.

I've seen the light.

yeah, you know what I'm re There was a great acquired episode, like a

week or so ago, and they had, Michael Lewis was interviewing the acquired,

I heard that one.

Duo.

You know what was really interesting was when they started talking about

advertising in the business model, the difference between like a Michael Lewis

and then, I forget the name of the guy, the acquired guys, but like they, they,

they're looking at things from their background as like business people.

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.

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 given the example of

somebody goes and buys JP Morgan payments.

Like they, they amortize the entire advertising cost over one customer.

And I was working with, with a well-known accounting company that sells software

for hundreds, 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

But wait, would they be able to track?

'cause I think one of the challenges every, 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 pr 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, you're, your, your advertiser or 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 have been a

lot more than they were paying me because then they signed up for the remaining

12 months and now I've been working with them for 18, 20 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.

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 in a habit, habit building relationship with the

user, over time that will play out.

But we both have to go into it eyes wide open that like we're

dealing with smart people who make contemplated purchases and we'll 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, 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 podcasts, for 2026.

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 and that like, you know, there, 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, but I want to get them to the point where their,

their, you know, annual partnerships.

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 30% 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 12 months.

And those don't happen overnight either one of these companies

who's doing an annual deal.

I met them in, in 2021.

Right.

And Nate actually never purchased anything from me except 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'll do is, three months, because that's

where I, I know that I can prove the ROI that you're gonna want to do more.

So that, that's kind of where the, the starting, place

So you, so you sell newsletter ads, you sell podcast ads, and

then I would say there's like, 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, breakfast, 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.

But you, you hit a wall.

Like, I mean, your, your ambition for this business, and this is something we

had been talking about before we started this, is, you know, you were a CFO, like

you're used to making 300, 400 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 1% or so in the company.

And like, you know, these companies, you know, if you sell for $300 million,

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 Green, but your, your, your ambition, financial

ambitions are a little different.

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 to definitely

make a lot more money than me, and many of 'em 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.

I know that's such an advantage.

It's

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, it's 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 I, what I had to get my mind around

is I'm running a company.

Where I want to be able to do it again tomorrow.

and I want to keep doing it the week after that and after that, and 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

on a clock.

You're on a clock.

Right.

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 like I,

I, 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 300 and $400,000 in cash a year, and then you get about 1% 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.

500 to 700 K in cash a year.

And it, it could be, it could be $5 million per year in equity, it could

be $20 million 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?

Because I've talked to some people who are

they are a 10 out of 10.

They, they're killers.

They're

Yeah.

Yeah.

And you have to be, you have to be like honest with yourself about like

what you know your unique skillset is.

And I think what your.

Unique yet, 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 is like, he was one of lots of products guys.

We had like, not, I'm not saying you're like one of lots

of like CFO people, but like

No, I, I probably was.

I

probably

Lenny 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, you know?

Yeah.

my advantage Brian, is I'm probably in the 80th percentile.

For CFOs, right?

I'm, I'm pretty good.

Maybe I'm the sixth man off the bench for the

All right.

That's Good.

I'm not Jason Tatum of CFOs.

Reve, like.

Yeah, right.

Hey, hey.

He makes pretty good money.

and I'm probably in like the 80th, 90th percentile for writing.

And then I'm also probably in the 80th or 90th 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 'em 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 I'm doing it live.

As I'm having this realization, 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.

This, this was 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, 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,

It's definitely more rare for, for finance people.

So breakdown, so like, so breakdown, like 90% is now subscriptions,

which is like kind of remarkable.

You went from like 0%, I'm sorry, 90% in sponsorships.

You went from like 0% being sponsorships, like I guess a couple years ago

to it being 90% because it's so valuable and because you execute real

Right.

So in the f first year, I, I monetized it, the majority were subscriptions and

we did like 150 K in, in, in revenue.

and second year flipped on the switch for advertising and also added

a podcast, did 1.4, and then the next year, the next year, and this

is

where,

threats from, from newsletter people.

Cj,

and then the next year, this is where I feel like if, if you give me.

90%, you get 90% 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 3 million this year.

So I feel really

so wait, but we, you had a $1.5 million side hustle.

Yeah.

Oh my God.

Yeah.

So, I

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 busy, like, you know,

like Emily Sunburg, I, I like Emily, I lo, I like what Feed Me's doing.

I think there'll be other types of feed mes, 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 want

to talk about the, the sort of risk of that because you, you have

to think about that too, right?

Like, I mean about building enterprise value or maybe you

don't build enterprise value.

I don't know.

I think that there's a lot of people in this area count myself as one of

them who is like, okay, I've, I've, 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 Market Beat and 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 75 million,

but nobody celebrates the people who are clipping off five or $10 million

a year and get to keep it forever.

And so.

I thought that was pretty powerful, that like, it doesn't 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.

But I've come around to just the joy and the ability to control

something and be your own boss and to live off the cash flows from that.

So it's just,

that's an, 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, now, you know, I, I haven't had a 401k

for like 10 years during like, but like there's gonna be some kind of

exit and you can't control that.

Right.

And you can.

If you have a cashflow generating, if you're at 3 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, those numbers, I've run the numbers.

Cj.

That works.

It definitely works and, yeah, it, it works.

And I, and I did run the numbers on it.

I, this is like how much of a sitco 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

Well, you're like, what, in your early thirties?

Where are you?

Yeah, 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,

Yes.

but, but I

work backwards towards if, if,

that.

I work 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 $2 million a year

or more, and control your own destiny and also take your daughter to dance or karate

00 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, see, '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 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 do 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,

Yeah, I, I say no to, I say no to almost everything 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 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.

What I realized is nobody's gonna want to 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 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 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 co and 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.

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.

the game so simple, folks.

No, but honestly, like, you've given me great advice on this

because you, you told me that time that, 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.

And the way that I've tried to construct it is there are network

effects between everything, right?

And 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 and 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's, the ground game, and

then you have the events, business or, or kind of, you know, add on

that you can do where you actually get physical people in a room.

And that is the most

That is the most valuable.

That is.

And I, am lucky enough to have built relationships with CFOs where I do these

small dinners where I get 25 to 30 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

Oh, it's a slippery slope, cj.

It is a slippery slope.

I don't want to be an events business.

Like I never got into this.

Like, I,

Okay, we're gonna, we're gonna be talking in like

two years about CJ Kahan and,

but,

and

but I think the key to that, Brian, is

you'll, you'll, you'll see what the events budget is for Brex

and Mercury, and I suspect you'll put on your fp and a, I don't even

know what those letters stand for.

You'll have to tell me a little bit,

but

but, but you wanna gate that though, right?

You don't want to give away the, the golden goose without having them sponsor

either the newsletter or the podcast.

So the way that I, I do it is like, I want to build a

long-term relationship 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

Yeah.

You know, I, I've been thinking about it a lot about.

And you know, I think a lot of times people, 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 and, and they're just, they're different.

Like if, to go back to that acquired podcast, they have a partnership

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, the event at the whatever, chase Center, et cetera.

And that is a partnerships business, sales businesses.

Our, 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, pump out emails, get more meetings, more meetings means more proposals.

More proposals means more sales.

Hey, have, have you gotten the key card?

sponsorship.

What about the wifi?

Okay, well, you know, we can do the sponsor teeny, 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 50%, 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.

And 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, it went into sales

and marketing, you know, like SaaS.

Like what are, what, what is Panda Doc paying to like, give me that extra login?

All, all their money goes to sales and marketing.

And when you have those like lu scapes, 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 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, 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

worked with Brex, I've

I was listening to Tipalti.

I'd 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, like money be green.

And to me it's, I only wanna work with, I wanna align myself with the best products

out there because what we were talking about before of wanting the, the point of

playing the game is to keep playing it.

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 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.

That's a pretty short term perspective.

it is 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.

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, 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, 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, literally.

And they're like, no, no, no.

It's not you.

You did great.

That's frustrating.

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 instead of a different game if I

wasn't gonna play on, on, on, not easy mode, but have some, I wanna

be running downhill with this.

Right?

Like, I, I

didn't

like to

run uphill.

You know, you're a runner and like I think you get stronger running uphill.

that, that's why it was attractive because a, i, I was a practitioner so

I could speak from a, a perspective of like knowing some shit.

Right.

I didn't wanna be like some Dante 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'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 as well as the rest of the company.

So looking at that, like, think about where you want to invest your time, um,

what you could be doing elsewhere, it seemed like a pretty, pretty good bet.

So let's talk a little bit about the, the content, because like,

I think what you quickly like, and I think your area like lends itself

to it, but I think obviously your experience lends it to tactical,

Super 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 'em make more money.

It's literally like, give me the Excel formula to type in for this thing.

It's not, well, hypothetically, I think AI

companies have worse margins and what will that maybe turn into?

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 who, you

know, I come from, you know, a journalism background, right?

And so like we do, like, you know, narrative and all that kind of,

of

People think the tactics are below them.

They really do.

Especially 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

a playbook, here's a framework.

yeah.

Here's a prompt for chat GPT that'll help you like figure

out your p and l like that.

That's worth it, right?

You would 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?

Because like, you gotta, you gotta dance to the one you brung.

And like, if, if one of your unique skill sets is not fp and a, but it's like, you

know, narrative and being able to like, you know, write that way, you know, it

doesn't make sense to, to do a bulleted list of like the chat GPT prompts that

will get you this or that and the other.

So,

I also find that there's a lot of value in leaning into

the, if you nose and your nose.

So there are certain things that if you've been in the role before, like winking 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 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, it's kind of a view through someone's career as, as they figure shit out.

So you've, you, 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, 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 and whatnot.

Or maybe you do it yourself, I don't know.

you've got, you've got a sales, sales guy I guess I'll call.

Who's your salesperson

sales guy, Matthew.

sales guy?

Matthew.

Okay.

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.

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 'cause I'm also a little bit burnt out from having done that, as a

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, 'cause like you're in the civilian world, right?

So like, I mean, you run into people and have to explain to them like,

like soccer games or something like this, what you do and they probably

look at you or like, are you okay?

Like, I mean like, can I help you or something?

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 and she's like, oh, what is your husband dude?

She goes, oh, he has a, he has a podcast and writes online.

You're in, you're in like, wait, where?

You're in Connecticut,

yeah, I'm in the Westport area.

Oh, okay.

So yeah, I mean, you're like, your neighbors are,

are not, are not podcasters,

So the lady looking at my wife, like, do I need to pick up the check?

Like, are they, is

this, 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

Yeah.

Yeah.

It's like, it's easy then you can go on to different things.

Whereas I like take like an exhale.

I'm like, okay, so here's what it is that I do.

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 brand 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 in 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 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

did

no, they don't.

But they, they don't have an office.

They bought their own computer, control their own schedule.

what, and what happened is, like there, having this type of business, it's kinda

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 want

to 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,

That's the best way to get in the recruiting business is say

you don't like recruit recruiters.

I've, I've had to pay millions of dollars in fees

Yeah.

I know.

This is, this is how it is.

It's like I had this problem and then I solved it.

And so, I was like, yeah, sure, I'll give it a try.

And so I put out the bad 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 match

make instead of 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.

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, like you have aspirational, I mean, you were not even

actually a CFO originally when you were

Yeah,

creating this.

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,

Yeah, but the flat fee is worth way more than like, 200 bucks.

it, it's a very healthy fee.

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

it's a services business offering.

it 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 200 CFOs at this point.

And then the, so that, that, that's the demand side.

And the supply side are the a, aspirational CFOs who want to get there at

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 300 people signed up, so I haven't

been marketing in very much until the full-time recruiter.

Not full-time, the recruiter starts.

Okay.

So that's gonna be a services line of,

that's the services line and, It's a very high margin

services line too, which is great.

Yeah, it's not creating white papers,

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

I love reports.

I

technology.

I know you do.

I know you do.

And, 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 don't have, right?

So that, that's supercharges the

But do you sell those as like lead gen or do you sell or demand

gen, whichever you wanna call it?

Like, or, or do you sell that as like, how do you, how do you monetize it?

It's fixed price, based on like this bill of goods that you get.

So maybe like I interviewed the CEO along with it.

you get up to three quotes.

Then if you want to, engage with us for the lead gen list too, then

that's a another separate amount.

But the two reports we did last year made the same amount as the 10 dinners we did.

Seriously, I gotta change my reports.

the reports, the reports are, are good and it's something I enjoy doing.

'cause I just like, 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 stack.

So, if you're a CFO, they, you used to say like, no CFO

ever got fired for buying IBM.

It's, it's very true.

You want to 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.

And so I think G two for those have 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 kind of 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, the newsletter, right.

Then you've got Run The Numbers behind you there.

That's 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.

And then run the numbers is kind of the audio version of

that, but an interview form.

And then what you can do is create more specific audiences off of

that or tangential audiences to it.

So I have another newsletter called Looking for Leverage, and you are

the one who taught me this, that you, you, you can go even more niche

into the niche and it's actually more valuable on a per subscriber basis.

And so that's my newsletter for

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, I'm sure if somebody out there could get the 32 NFL owners on one email

list, that would be a very valuable list, even though there's only 32 people on it.

If I can have 20 to 30% of all private equity backed CFOs who operate a

little bit differently on one list.

I don't need to have 30,000 subscribers.

I could have 9,000 subscribers, and it's just as valuable as some newsletter

out there with 200,000 subscribers.

know what percentage of your revenue is tied to the

newsletter versus non newsletter?

Because I think one of the sort of.

If I were to like do one of those, like trends of like 20, 26, I

mean, I've been beating this drum for like, for years at this point.

is, I'm kind of bearish on quote unquote newsletter businesses.

I mean, I think newsletter and, and selling newsletter ads is, is great.

Or, or subscriptions.

I just think the ceiling is fairly low for most categories.

Le you're not, most people are not gonna build industry dive and, you

know, they're, 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, because that's the reality of it.

I think about this so often, Brian, because right, right now it's about 40%

newsletter revenue, 40% podcast revenue.

10% reports, 10% 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.

'cause 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

Some healthy monetization.

I was just listening to one.

Yeah.

And, but then you also look at it like, if I give you 60 minutes worth of

content,

good.

Hey, if you're, you're not gonna

get complaints about monetization from this guy.

You got the wrong person here, cj.

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.

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 want to 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, 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 finally be a bonus.

That's a little bit variable maybe, to, you gotta like,

you know, you have no idea.

I mean, and for a lot of people, 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, 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 2027 and 2028.

So yeah, 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 2026 in late June of 2025.

So I'm still very much on the prowl to.

Line up these longer term partnerships.

So in that sense that you can never rest.

You're, and you talk about that acquired podcast with Michael Lewis,

they said they're working, they have sponsors already signed through 2027.

Like I want to get to that point.

So like there's always a the next mountain to, to

They also have the number one technology podcast in

the world.

So, that is, that is like an advantage of, so, I mean, but do you want to,

like, what do you want to build, because 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, because I mean, I imagine from the personal, 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, we've got, we've got a little bit of a tire 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, finance, class.

I don't know.

How do you think about.

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, your finance

department, someone who, who doesn't take themselves seriously, but

takes the work itself seriously.

and I'm a huge fan of Deadspin and, and now the defector.

So those are like the publications that I grew up on.

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 Bar Stool, boss 'em 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 mine went to, I can make more if I package

the newsletter and podcast together.

This is a pretty simple

Oh yeah, I remember that.

I think we talked about that.

I

I called you 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

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

but it's not like he's doing his own podcast and, like.

Because you gotta figure out what, what's the most that you could clip off

somebody else's podcast or newsletter?

I'm just making up numbers here.

I don't know what it is, but let's say it's 25% 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?

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?

Well, you just hire 'em, right?

Like, I mean, you, that's, 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?

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 and a.

You have to tell me what fp and a is.

Financial planning and analysis.

The

Okay.

Okay.

There you go.

We're gonna create an fp and a like sub-brand 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, and this is the hardest part for me to get my brain around, I

think part of what makes it special is the scarcity that I, that I could do so

much more 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 get to strap 'em to the mast of the boat so he

The sirens.

The siren

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 want to create a fund.

I don't think I'm uniquely qualified to pick the companies.

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 a hundred people to shell out a thousand

dollars, which is, that's a considered purchase to give somebody a thousand

dollars, it's still only a hundred thousand dollars per your 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

kind of 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 struck with, and I've struggled with

this a lot, is on sales, right?

And I've tried a whole bunch of different approaches to, to sales.

And I think this is 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 competitive, 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 recognize 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 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 would've 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,

Oh, it's the biggest hack because I was listening to the Acquire 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 and having a buffer in between.

You get to play the good guy with everybody and you just say, no, no, no.

Buy the newsletter and podcast.

We'll talk about the other stuff later.

Because 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,

doing like this weird host red ad where the other person, 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 skews.

Like it's not.

skews versus 60,000 of a 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 if, 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

But it cheapens.

It cheapens the main thing when you do that too often.

So yeah, you can be like, you know what?

I'll go speak at something for X amount this time around.

What I found is better, and I stole this from Prof G, is you only have two

prices, fucking expensive and free.

And there is no shame in going to the free bucket because it shows that you

really value their partnership and you'll go above and beyond for them and

you want to 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 because I think

that's healthy for the long term of it.

It's not, you know what, that's $5 over there.

If

Right.

This is the sales versus partnerships.

Honestly, because a lot of this is no shade at my, 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 want to chop up everything, to want to create new SKUs,

to create, I want to create custom SKUs.

I remember early in my career being like, or 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, what could cocoa break?

What are you talking about?

What is a cocoa break?

And, you know, the salesperson had like, you know, roller skated away at

that point, sort of left me, left me with a deliverable of a cocoa break.

And I, and so it's really easy to get pulled into having.

It's the, the 60,000 skews.

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 and like just staying

below it in terms, because you, you do have to do self-promotion and I hate it.

I hate that part.

I hate some of the like,

You're really, you're good at it.

I think

well I ho I hope because it comes across as genuine.

Like I'm not out there just showing LinkedIn posts of

you should buy this or that.

Or,

time for a thread.

yeah, ti time for a thread.

Like, I don't do any of that stuff.

'cause I think it cheapens everything else you do and makes

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.

I'm very impressed with how, how you, 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 want to 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 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.

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 $200,000 of my own

money into it and, and lost it.

And I've tried five or 10 other ideas that just didn't pan out.

And it's just so funny that the one that costs 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 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 in 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

Right.

Well, you also, you talked about, about it not getting bored, like that being

the well, the, you know, some people 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 you're, you're, 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 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, his stuff kind of like drives me nuts a lot of times.

'cause I'm like, I don't need to go down a memory lane to something you

wrote in 2013, like in paragraph three.

Just as like a editor.

It offends me.

but I know that he has a lot of, of, of fans

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 20 20 13?

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, he takes a photo.

He's just, you know, and like that scales, that's why he's been able to

do this for whatever, 15 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

Oh yeah, it's a Mexican.

Everything's a Mexican restaurant.

Is it a chimichanga?

Is it

yeah, is it a burrito or is it, is it a burrito bowl?

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 Ky 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 attention for, for

me and do it better next time.

And then what I also think about is if I'm at 70,000 subscribers now and

I was at, you know, 60,000 last year, I mean, there's a lot of people who

didn't read it the first time around

Oh my God.

I used to have these reporters who we would be talking, If any of listening.

I, I, I 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 edit.

I'm the editor and I don't remember.

So

Yeah,

we're safe.

I wrote it now, don't remember.

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 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 wanna write about.

Okay.

Final thing.

What are, what are, what are some like three media comp 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 want

to, I wanna learn or emulate from parts of, of those businesses.

If I could have dinner with anybody, it would be Scott Galloway.

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 up

Yeah, but he is also like taken that cash flow.

He, he's beyond that part of it.

The business itself of

being Scott Galloway is pretty amazing.

Yeah, and I mean, like, I am.

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 'em on the same RSS feed and then

break them off as experiments?

What does he do with the cohost?

What's the amount of time the cohost 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 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 Stanzi, he writes, hello Operator.

I think it's a super tactical, you know, newsletter for PE the

Operators, Kyle Harrison writes investing 1 0 1 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.

man.

Great.

Hang.