A
Aj Cassata
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APPEARANCES
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Nov 6, 2026
If They Say "Yes" Right Away, You're Losing Money
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Preston LeeHOST
Now, what should my pricing look like? AJ, where do you think he ought to start with something like this?

AJ CassataGUEST
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.

AJ CassataGUEST
And essentially, as you get, you know, as more time goes on, you can start to be more picky.
12 MINS LATER

Preston LeeHOST
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?
No Portfolio, No Problem… Here's Where to Start
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Preston LeeHOST
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.

AJ CassataGUEST
And I was actually, yeah, I was actually just, um, I wasn't even trying to be in the bagel niche.
9 MINS LATER
More Clients, Less Freedom — What Went Wrong?
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AJ CassataGUEST
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.

AJ CassataGUEST
And it's going to really help illuminate all the things you're spending your time on.
7 MINS LATER

Preston LeeHOST
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.
Always Chasing Clients = You're Doing This Wrong
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Preston LeeHOST
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?

AJ CassataGUEST
But the first thing is try to see if you could create some recurring revenue in the business.

AJ CassataGUEST
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
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14:19speaker_0ADVERTISER
Um,
Why Premium Clients Aren't Finding You
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Preston LeeHOST
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?

AJ CassataGUEST
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.

AJ CassataGUEST
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.

AJ CassataGUEST
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.

AJ CassataGUEST
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.

Preston LeeHOST
What do you think about that kind of offer? Good, bad, in the middle somewhere? What do you think?
Are You Charging Too Little… On Purpose?
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AJ CassataGUEST
... 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.

AJ CassataGUEST
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.

AJ CassataGUEST
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.

AJ CassataGUEST
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