Sep 1, 2026 · 28 min · 12 segments
Visit https://www.pamjordan.com to work with Pam’s team. ✖️✖️✖️ What if the technology you’re investing in to grow your business is actually costing you more than you realize? In this episode of…
Don GregoriGuest
Pam JordanHost
What are some mistakes that you see small businesses making when it comes to software and AI? Because there's a lot of financial mistakes.

But what are the big, give me like two or three that you're seeing over and over that small business owners are making when it comes to software, tech, AI?

I'll say the first thing is really, and it's kind of like, you know, even at a big business when you've got an RFP, you know, certain companies, they go with, you know, the lowest cost provider.

You have to look longer term with software, right? Software isn't a one and done.

It really does require a lot of maintenance, right? There are new versions that come out.

So you really have to make decisions about your software, not only about what I need for this defined window, right? I'm looking to get something released in September and here's the goal.

And that's just maintenance and not only, okay, well, how does this evolve based on customer feedback? If you have a diverse clientele, like what might need to be customized for each of them? We've got these increasing vulnerability exploitations from malactors, especially with AI.

They're using AI to exploit vulnerabilities and phishing and taking sites down.

You need a stronger security posture and a vendor to work with that actually understands that.

And so I think that there's that, and then there's the iterations you want to be able to scale.

And, you know, when you build something for a defined need, it doesn't necessarily translate to I need to scale this 5x in a year because all of a sudden, you know, I've hit a growth spurt.

And so a lot of times what happens is you go with a cheaper provider, which may be offshore or something, and they just don't have the capability to pivot, to scale.

And so I don't think it shouldn't be a race to the bottom for the cheapest product.


And the engineers are really thinking through all the critical thinking and the requirements and the guardrails and everything to control AI.

If you don't have that right, AI is building code in a day that would take engineers weeks to do.

So if you're off just a little tiny bit in the beginning now, you're off a mile.

And you may not know that until your clients are using the software a month or two months down, and that is where the rework is now getting even more costly.

What are some mistakes that you see small businesses making when it comes to software and AI? Because there's a lot of financial mistakes.

But what are the big, give me like two or three that you're seeing over and over that small business owners are making when it comes to software, tech, AI?

I'll say the first thing is really, and it's kind of like, you know, even at a big business when you've got an RFP, you know, certain companies, they go with, you know, the lowest cost provider.

You have to look longer term with software, right? Software isn't a one and done.

It really does require a lot of maintenance, right? There are new versions that come out.

So you really have to make decisions about your software, not only about what I need for this defined window, right? I'm looking to get something released in September and here's the goal.

And that's just maintenance and not only, okay, well, how does this evolve based on customer feedback? If you have a diverse clientele, like what might need to be customized for each of them? We've got these increasing vulnerability exploitations from malactors, especially with AI.

They're using AI to exploit vulnerabilities and phishing and taking sites down.

You need a stronger security posture and a vendor to work with that actually understands that.

And so I think that there's that, and then there's the iterations you want to be able to scale.

And, you know, when you build something for a defined need, it doesn't necessarily translate to I need to scale this 5x in a year because all of a sudden, you know, I've hit a growth spurt.

And so a lot of times what happens is you go with a cheaper provider, which may be offshore or something, and they just don't have the capability to pivot, to scale.

And so I don't think it shouldn't be a race to the bottom for the cheapest product.


And the engineers are really thinking through all the critical thinking and the requirements and the guardrails and everything to control AI.

If you don't have that right, AI is building code in a day that would take engineers weeks to do.

So if you're off just a little tiny bit in the beginning now, you're off a mile.

And you may not know that until your clients are using the software a month or two months down, and that is where the rework is now getting even more costly.
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