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Aj Cassata

Nov 6, 2026

3:15
Now, what should my pricing look like? AJ, where do you think he ought to start with something like this?
3:21
Yeah, well, I think it was...
3:22
I saw somewhere on maybe your LinkedIn, you posted a graph one time of basically a line going up, and on the x-axis, it's how selective you can be with your clients and your pricing, and on the y-axis, it's your experience.
3:36
So I think kind of what you were hinting at earlier is that as...
3:39
It was different stages of the agency.
3:41
And essentially, as you get, you know, as more time goes on, you can start to be more picky.
3:45
And that typically comes with raising prices.

12 MINS LATER

15:22
Like, how do you kind of, I don't know, decide timing on, on when to raise your rates? Cause I think we've talked a lot about how do you decide if you should, but how do you know when's the right time?
1:54
So how do I land my very first client? I'm curious, do you remember your first client, AJ? And how did you find that client? And while you share, I'm going to try to remember my very first client.
2:07
Yeah, it definitely takes me back.
2:09
I think my first client ever was a bagel shop and we built them a website.
2:13
This was maybe eight years ago.
2:16
And I was actually, yeah, I was actually just, um, I wasn't even trying to be in the bagel niche.
2:20
It was just, Hey, I'll take any client that I can get if I'm starting out.
2:23
Right.

9 MINS LATER

11:06
Again, that's QuickBooks.com slash workforce.
2:06
You ever experienced this or known anyone that experienced this?
2:09
Yeah, absolutely.
2:10
And it sounds like.
2:12
what you were saying, perhaps just not make it enough, but I would always just be first asking why am I working around the clock? What am I actually doing? And a really helpful exercise is a time audit where you just keep a notepad paper next to you for a week or two, ideally two weeks.
2:30
And just write down everything you're doing for those two weeks.
2:33
And it's going to really help illuminate all the things you're spending your time on.
2:37
And then you group them into categories.

7 MINS LATER

9:50
from 90% good to 100% good when in reality you just need to ship it and charge your client and move on to the next project.
2:39
How do I even that out and make my business feel a little more predictable? What advice would you have to kick us off here, AJ?
2:48
Yeah, that is the age old freelancing dilemma, right? Right.
2:52
There's two things that come to mind.
2:54
I'm really curious to hear your thoughts as well, Preston.
2:56
But the first thing is try to see if you could create some recurring revenue in the business.
3:01
Even if you have a business or an offer that doesn't feel like it.
3:04
Recurring revenue where it's project based, there's always something you can offer on a monthly basis, like whether it's consulting, whether it's maintenance, etc.

11 MINS LATER

speaker_0ADVERTISER
14:19
Um,
2:38
So the real question at the heart of all this, AJ, is how do you land higher paying clients? What recommendations do you have for Pueblo?
2:48
Yeah, for sure.
2:49
So...
2:51
I think, especially because you mentioned local clients, it really comes down with changing how you market, right? If you want to land a different type of client, you have to change your marketing, you usually have to change your offers, and the whole way that you're acquiring clients has to change.
3:05
And especially because you mentioned he's a local business, I know that a lot of freelancers, and myself as well when I first started out, typically don't do any marketing, right? They rely on referrals, they rely on networking, people that just come through word of mouth.
3:18
So if that's what's happening here and the clients that are coming to you through word of mouth are just very, very small businesses, then you just have to kind of step out of that entirely and just start doing some proactive marketing campaigns, right? There's a point in every freelancer's journey where they have to stop being reactive and start being proactive, right? Stop taking what just comes in and start actually going out and taking a more strategic approach to the business they want.
3:43
Because what's going to happen is, and probably what's already happening is, if you get referrals, like people refer you to people that are like themselves, right? Like if all of your clients are very small local businesses, well, who do they know? They know other small local businesses, right? So you're kind of just going to be trapped in this vicious cycle if you want to move up and beyond, right? As far as where to find these premium clients, I mean, I run a cold email agency, so I'm pretty biased, but I do think that's the best place for everyone to start.
9:01
What do you think about that kind of offer? Good, bad, in the middle somewhere? What do you think?
4:24
Mm-hmm
4:24
... pay me just really any price just so I could get the experience, right? So it definitely has a lot to do with, um, where you are in the journey, but I, I think a good rule of thumb no matter f- where you are is if you think, if you feel like you can raise your prices, then usually there's more room.
4:37
Because I find most people, a lot of freelancers especially, um, they will typically, you know, very much underestimate their pricing more often than overestimate it.
4:46
So if you feel like there's room, then there's, there's probably room.
4:49
Um, but really my best rule of thumb is just raise it every so often.
4:53
You know, like, i- if you're, if you're pretty new, you can pretty much raise it a little bit on each new client until you find that sweet spot where you start to get a lot more resistance, right? Um, and then typically from there, you know, like, we'll usually raise our prices maybe once or twice a year a little bit just to keep up with inflation and, and rising costs and added value in our service.
5:10
Um, but yeah, the best thing you can do if you're unsure is just keep bumping it up incrementally until you start to see some serious resistance.

13 MINS LATER

18:21
Mm.

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