3 Tips for Scaling Your Agency Past $100,000 Per Month

Chase Dimond | Email Marketing
40 followers
Sep 12, 2026
In this video, Chase Dimond and Cardinal Mason discuss:
- New money-making method Mason just discovered
- LinkedIn Business Update
- 3 Tips for Scaling Your Agency Past $100,000 Per Month
Welcome back to another episode of the Diamond Download.
Chase, look.
The tree, it's up.
It wasn't a bookshop with one book.
It looks great.
Dude, I'm so excited.
I'm so excited.
We had some Michael Bublé playing the other night.
We're in Christmas mode, man.
Dude, it's nuts.
When we recorded this last week, it was Halloween, and that feels like a lifetime ago.
Oh my god, yeah, I just realized.
Last Tuesday was Halloween.
Yeah, insane.
Time really flies when you're having fun, eh, Chase?
100%.
Let's do this, bro.
I'm excited to chat.
All right, so topic number one, it's this new money-making method that I came up with
on Saturday.
It's called gambling, but it's called being good at gambling.
So my method of choice, okay, first of all, let me just say, I went to the casino.
You ever been to the casino, Chase?
Yeah, it's been a while, but I for sure have.
Do you remember winning any money?
I think I won a little bit, and then I left.
I'm pretty responsible.
I think I won like 50 bucks, and then I bailed.
I would consider it irresponsible to leave when you're winning.
I would say that the more responsible thing to do is just to keep doubling down until
you are up $2,300, like I was.
Is that what you did?
Yeah, so I pulled out $1,000, I left with $2,300.
It's the first time this ever happened to me in casino history, but here's the trick.
I brought a witch with me.
So there are people that are super, they're actually able to do magic and stuff like that.
And so this witch that I'm talking about, every time she pressed a button, we'd make
money.
Every time I pressed a button, we'd lose.
And we made most of our money with roulette.
So you ever played roulette, Chase?
I have.
I normally play poker or blackjack, but I have.
See, those are rigged against you.
The more random, the better, because all it does is require luck.
But if it's a skill-based game, you're going to lose.
Unless you've been, like, listen, if I played poker for like 45 years and then went to casino
and I just like took everything, I could do that, but like, we're young, we don't have
time.
We got to make money now.
So the way to do it is to harness the randomness of the universe and direct it into a game
that I like to play called roulette.
And the way we did it was, we started with like, I think it was like 400 bucks, and we
ran it all the way up to like, I think it was 2,400, and then the rest of the money
we just lost doing other stupid ----, but like, listen, I'm not encouraging anyone to
go and gamble, but if you do, you got to play roulette, you got to go at least 100 bucks
a hand on like a color, and then odd or even, and then lows or highs.
And I think that's the best way to do it.
Don't play video roulette.
You got to do it with like a live wheel, so you know you're not getting scammed.
But pretty interesting.
So I mean, yeah, long story short, I went to the casino this weekend, it was super fun.
Scary, because like, a lot of the people at the casino are like old people, like old,
like in their 80s, which I find kind of weird.
I mean, on one hand, it's kind of cool, because it's like, if you're 80, and you know, you
got like a year left to live, and you got like 2 million in the bank, like, by all means,
blow it at the casino.
Like, what are you going to do with it?
Nothing.
You know what I mean?
Pay off your house?
Maybe.
Like, take it to the casino and see if you can make it 10 million?
Like, way better.
You know what I mean?
I'd rather do that.
But also, it's kind of weird seeing people who like don't look like they have 2 million
in the bank, that are just like down bad, staying on the same slot machine for like
hours at a time.
It's a strange place.
I wouldn't recommend it for like children.
Dude, that's hilarious.
All right, well, next time you go, I'm curious to see how you score.
You should come with me.
Okay.
Sounds good.
Yeah.
California?
Yeah, of course.
Local casino.
I don't know where it would be.
I know a couple probably within an hour, hour and a half.
Okay.
Not bad.
I didn't think California lets you gamble.
I feel like that's one of the things that they would restrict.
Yeah.
There's a couple casinos for sure.
So, next time you're out here, we'll do it.
Okay.
All right.
Next one.
Bringing it back to earth here.
LinkedIn biz update.
This is selfishly for me because I kind of want to know what you guys are up to.
Are you still hiring?
Are you still scaling?
What's going on?
was incredible.
I think I was telling you a little bit on Tuesday that we were doing well.
We were on a high.
We're going to roll out some Twitter stuff.
Dude, last week was the best week by far.
I think we had maybe 18 to 20 people sign up last week just for LinkedIn.
And there was another half a dozen to a dozen people that signed up for Twitter.
And all I did was one tweet and kind of softly mentioned the Twitter thing was coming on
the pod.
So, last week was a great week.
So, 18 to 20 people on LinkedIn, another 6 to 12 on Twitter, and everyone's paying, you
know, 500 bucks.
So, it was really good.
And everyone stays and retains for a really long time.
So, it's just like continually adding to the MRR.
It's been great.
We're hiring a sixth person here soon.
A lot of people signed up.
I feel really good.
What?
You guys are going nuts, bro.
Yeah.
So, do you have any, does Jamie have any ideas on what to do with all this new money?
No.
She doesn't know.
We are doing a backyard project, but no.
She doesn't know.
But, dude, I think I posted like a tweet about this, but essentially what I've been doing
is anytime someone in the program does well, they'll send us a text, typically.
Or if we notice it, we'll send them a text.
And then we'll just screenshot that text of someone who's like, hey, I have my all-time
record.
I had, I don't know, 850,000 impressions last week.
And he's like, my previous best was 700,000, so I'm up X percent.
That was a screenshot.
That's a tweet saying, in our first week with this guy named Chris, you know, he's hitting
records, right?
And oh, this guy just signed three clients, and now he says he'll stick with us for the
entire year or more because it's paid for a year, two years, three years of our service.
So every time I get that, I post it organically, and then I just throw it into an ongoing ad.
I'm up to like 27 or 30 ads at this point, and I'm spending like $30, $40 a day in total
across like 30 ads.
And so every ad's getting like, I don't know, 50 cents to $2 of spend on it, and it's driving
tons of DMs.
So that's really what's working is organic posting on Twitter, boosting it with spend,
targeting my own followers.
Every single day, hopefully someone is seeing something from me about it.
And then the other part of it is about 50% of the people are referring us clients, and
we don't really have like a referral bonus or incentive.
So it's been great.
That's awesome that people are getting different ads over and over again, because like a lot
of people that run Twitter ads will run the same creative for ever, ever.
And it's like, dude, like, let's refresh this.
But like, if you have like 30 different testimonials that you're just throwing out there, like,
it seems like there's just something new all the time, which is really cool.
But yeah, dude, that's awesome.
Do you have people that are like fans of the business?
Like I was thinking about this, where it's like, we do these little LinkedIn biz updates.
I wonder if people like, look forward to like the updates about it like I do, because like,
I'm kind of like a fan of the model.
Have you had anybody reach out and be like, be like, yo, Chase, like the service you're
offering is cool or whatever.
I don't need it.
But it's cool.
But like, I wanted to say like, the business is ******* sick.
Like, do you ever get that?
Yes, but it's targeted.
Like I've had a few people do it, or like the way that the Twitter launched was a couple
people that pay for LinkedIn are like, dude, this business is awesome.
As soon as you launch this business, we were like, yeah, you know, we're stoked about it.
We're jazzed about it.
Like, should we do the same thing for Twitter?
And then someone else hit me up the other day that's a customer is like, dude, I'm in
both your LinkedIn and your Twitter things.
Now, you want to be business partners and do this on Instagram.
So people have hit me up, but it's more like tailored around.
I love what you're doing as a fan, but also a customer.
Can we expand to X, Y, Z and platform?
And let's partner up.
So some people have, but it's more like that.
No, man.
This is an off the cuff question.
This is not obviously on the list, but like, do you have any businesses like that where
like, you probably wouldn't use the product, but you're a fan of the business?
Yeah, that's interesting.
Like a fan of like the model, right?
Like I think like something's really genius.
Or the brand, like, yeah, if you just think that they're cool, but like, I don't know,
you probably wouldn't use it, but you just think everything they do is great.
Yeah.
I mean, I think like, I guess not specifically a brand that doesn't come to mind, like can't
think of a brand necessarily.
But there's like some models I've been interested in.
Like, I think it's really cool, like with Sahil Bloom and kind of, you know, Nick Hubert
are doing like, they built this massive social following, right?
And now they're like rolling out businesses.
Sahil, I don't know him personally, but he looks like he's partnered with this one guy.
And this one guy is just building tons of productized services around Sahil and Sampar
and Cody Sanchez and some of these other people's brand equity.
I just love that model of like pairing influencer or creator with someone that wants to do operations
and like marrying the two.
So I guess, you know, not that that's anything new or special, but I think it's really cool
how it's being done.
Like, you know, Sahil will put out a tweet or Sampar will put out a tweet or the big
guy on YouTube, Ali, I want to know, Ali Abdaal, or he's like the productivity guy butchering
his name.
I think I know who you're talking about.
These guys put out one post or one video and that's like seven, eight figures sometimes
of ARR.
So I think that's really interesting.
What about you?
Do you have any thoughts?
I mean, the first one I thought it was Taylor Swift, like not a fan of the music, but I
love the way that like, I think Taylor Swift is one of the greatest like marketers, entrepreneurs,
business people of all time.
She's a billionaire now.
Did you know that?
Insane, yeah.
My wife's a big fan.
She told me about that.
I don't know what happened.
It's insane.
Billionaire.
I think she got there before Drake, which is crazy.
She's 33.
Yeah.
I think she's 33.
She did it.
Not a Taylor Swift music fan, but like big fan of the way that she like has built her
brand like every, like one out of every two women in America is like a Swifty.
Oh, and dude, and it transcends like demographics and ages.
Like my daughter Shay is three years old and loves Taylor Swift.
Like whenever I'm in the car with her, she goes, hey, throw on that t-shirt song from
Taylor Swift.
And I like, they're on the song.
Um, you know, my wife went to the concert, you know, spent thousands of dollars on a
ticket to go to the concert.
Then Taylor Swift dropped a movie that was like a one day sale of like these movie tickets.
My wife bought four tickets, one for her and then three for her friends.
I think those are like $20 tickets.
I think Taylor Swift did like $26 million on movie tickets in like 24 hours.
And then I think went on to do more.
She opened up more tickets.
My wife and her friend at the concert, after the concert ended, they waited in line for
a good 45 minutes to an hour to buy merch.
And the merch was really expensive.
By the time they got there, they only had like double or triple XLs left.
And my wife and her friends still bought them and do, they bought like this basic jacket
for like 80 bucks.
It was like this, it probably costs $2 to make.
They bought it for like 80 bucks and they waited 45 minutes.
You know, her new album came out recently.
All this stuff.
It's just crazy.
She elevated her boyfriend, Travis Kelce, Grateful.
I'm a fan of him too, man.
He's a handsome kid.
Dude, he's in all the commercials, he's all the attention.
So just her notoriety and her association is massive.
I didn't realize Jamie was like a Swiftie like that.
Yeah, I knew she was a big fan and then all of a sudden, all these things started coming
out.
So you talk about I don't spend a lot of money, like all my money goes towards Taylor Swift
for my wife.
Well, I'm so sorry to hear that.
You are part of the problem, but yeah, no, I was just, I was thinking that because like
I've been fascinated by like the model since I've seen like what she did with Aeros to
her and bro, like everything she touches just makes me, like it's insane.
And so it seems like a sweetheart, like she's been around since like 2006 or something like
that.
That was when she was dropping music.
Like I remember there's the first song, one of the first songs I ever learned on guitar
was a song called Teardrops on My Guitar by Taylor Swift.
Yeah.
Anyway.
Yeah.
Fan of the model.
Products.
Whatever.
Oh, let's not forget that she drops the same album back to back.
Like bro, like songs that she recorded 10 years ago, she just re-records them and drops
it again and charts.
Like she's literally all the top 10 on Billboard.
She's like eight of them right now.
Yeah.
It was that whole thing that happened.
Like my wife explained, like the whole thing that happened with Scooter Braun, right?
Like he sold or her bought her old stuff and she was just like, F it.
I'm just going to re-record.
So now everything's called like Taylor's version.
It's the exact same song.
It's just re-sung.
And like my wife is too, like whenever we're playing music in the car, she wants to make
sure it's Taylor's version, not the old version.
It's like, what?
It's the same thing.
My wife's like, no, we got to support Taylor, not Scooter Braun.
It's just like, it's crazy how diehard these people are.
Yeah.
No, that is a little crazy because like Taylor Swift has more money than you guys.
So like it's kind of whatever, you know what I mean?
I kind of like the old versions.
I haven't listened to the new versions, but regardless.
Okay.
Last one.
Let's end it off.
This is inspired by, listen, I'm not going to name any names, but like I know a lot of
pretty intelligent entrepreneurs or seemingly intelligent entrepreneurs that have agencies
and just can't break past like the 100 to 150 a month mark.
Yeah.
As far as I know, you guys flew by that in like your second year or third, maybe whatever.
But like, I just, I'm thinking about like all these people, I like, I know there's challenges.
I know that there are people that like, I don't know, maybe they want to prioritize
something else, but like you guys have kept up your product.
You've kept up your revenues, but continuously growing and it seems like your margins are
like pretty standard, you know what I mean?
For an agency, what would you, what would you tell an entrepreneur who's struggling
to get past?
Let's just say 150, right?
Because I feel like that's like a really sticky point for a lot of agency owners.
Like what would you tell people if they're struggling scaling past that?
Yeah.
I think it's normally like three things, right?
It's like acquisition, retention and process is kind of like the simplest way I think about
it, right?
I think a lot of people that can't scale have probably all of the above problems, right?
Acquisition, they're just not acquiring clients quickly or effectively or at scale, right?
They cannot fill their pipeline up.
I think that's one.
Number two, I think they can't retain clients, right?
Like, you know, they need to, if they can't acquire clients, go into huge retention mode.
Like if you can save a client and draw them out to a two, three, four, five year deal,
obviously, right?
They're not going to sign it up front, but if you can keep them for that long, maybe
you don't have to be as good at acquisition, but you're really good at retention.
You slowly and surely kind of add to it, right?
I think the last one is like process.
A lot of people are just flying by the seat of their pants.
They're very much in the business for better or for worse, often for worse in that stage.
They are the business, right?
And if they take a day off, which they probably can't, and they do certain things like things
just crumble.
So I think like acquisition, right?
Like what are the, what's the channel or what are the channels?
For us in the early days, like a lot of people, it was cold email.
It was DMs.
It was those types of things.
And now everything is just outbound to inbound.
And what I mean is like we create content and that drives clients.
So it's like just scaling and building a personal brand today because it takes a long time.
It took a couple of years for us to get to the point where everything came inbound.
And now it's just like, dude, I can post on LinkedIn.
I can post on Twitter.
If I can send more newsletters, just a little bit more each week, it compounds.
That probably gets us another three, five, seven clients a month if we just do a little
bit more.
Retention, right?
Like we've gone through the ebbs and flows of services and prices and times and teams
and whatnot.
But the better you are retaining clients, the more referrals you get, the less chasing
you have to do, the less onboarding you have to do, the better.
And then process.
I think that's where the biggest things break down.
People don't know who's doing what.
You know, they don't have things that are templatized or systematized.
So those are like the quick kind of fire ones for me.
What are your thoughts?
I mean, yeah, like you guys have been really good at creating content and like just sort
of like being the go-to.
Like, I mean, I don't know anybody else who has like more of a grip on like email in the
space than you do.
Yeah, I'm trying to think like, I mean, humbly, like you must know that you are kind of like
the email king, especially with your new format.
I was actually like, I was texting Ben.
I was like, Chase is like funny now.
Because you've always been funny.
Like I know you as like a funny guy, but like you like.
Yeah.
Oh, the likes and the comments.
And it's like, it's like your humor, which makes it like so like endearing.
And, and I, yeah, I think like, I don't think there's anybody else who's really doing it
like you guys.
In terms of retention, like I remember, like you guys, you guys have any like legacy clients
that are sticking around from like 2018, 2019 still?
We just lost one of them.
Like Original Grain, we signed in 2018, 2019.
They left a couple months ago to bring it in house.
But we had them, I don't know, let's call it four-ish years.
I think Hydrant is still with us.
That's four-ish, five-ish years.
So we probably have maybe about a half a dozen clients that have been with us for five years
so far.
And a lot of, a lot of clients, dozens of clients that are at year two, two and a half,
three, that if you give us another six or 12 months, you know, I think we'll still be
with us.
So a lot of clients are legacy.
And obviously, right?
Like there's a lot of new clients that just signed on today, yesterday, last week.
And would you recommend like maybe investing a lot, like basically more money than you're
comfortable spending like in product?
Like I think that's another thing that holds people back.
It's like they get, they're scared to get big because they know their product is going
to slip.
Would you say to people like maybe like spend money on like a really good operator, over
hire so that you, like you can kind of go like that?
Yeah, a hundred percent.
And dude, you saw the stuff that we had on notion.
I thought that stuff was good.
We just did like a huge overhaul recently.
We moved over to ClickUp maybe about three to six months ago and that got completed probably
about a month or two ago.
And the new process we have is just like insane.
Like I, I thought like notion was like really good and it was like over my head how good
it was.
Like ClickUp is just like next level.
Some of the stuff that the team's implemented, I can't take any credit.
I have no clue how they did it.
I still don't even know how it works.
Thankfully I don't have to use it.
But like, it's really cool.
Like they're showing me things and I just kind of randomly peek into channels and see
some of the looms of it.
It's sick.
That's dope, man.
Not sponsored, by the way.
No, not sponsored.
Not sponsored.
I don't care if anyone uses it.
But, but invest in some project management system.
Notion, ClickUp, Sana, Trell.
Like I don't really care.
But invest in that.
Someone has to own it.
Someone has to manage it.
Someone has to update it.
Like it needs to be fluid.
It needs to be evolving.
Iterate feedback.
So 100% over invest in systems, processes, and people.
And it's like a lifetime of difference.
Because the times that we've done that, we've been great.
The times that we haven't done it, it's like, it's twice the cost.
Because it's the cost of having to change and then the cost of having the time it takes
to change and the clients maybe churn.
So yeah, do it once right versus we've done it a lot of times wrong and then had to adjust
and fix, which is hard.
This is great, man.
This is great.
I hope everyone scales to 155K.
That one extra client, dude.
Squeeze that one more retainer out.
Good stuff.
Anything else, dude?
No, this is great.
I love the Christmas tree.
I love it, too.
Thank you.
Hey, wait.
Do you have my hand?
Wait, hold on, Chase.
One more.
Wait.
Let me get my little sign out.
Broccoli here.
You should have worn it the whole time.
Thanks everyone for tuning in to the Diamond Download.
This has been Cardinal Mason and Chase Diamond.
Find us on social media.
You guys know where to go.
We'll see you next week.
Cheers, brother.
