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Ever feel like your technology stack is running you, instead of the other way around? Even moreso now with AI booming.
Nick Berry interviews Jay McCauley, fractional tech partner who helps non-technical founders stop wrestling with their tech stack and start buying back their time.
Jay left his corporate role in customer success at a software development agency to build his own business, and now works with a select group of founders who need reliable technical support without hiring full-time.
In this episode of The Business Owner's Journey, they dig into what Claude Cowork actually means for business owners, why software for one is replacing bloated subscriptions, and how the shift from done-for-you to done-with-you is reshaping how founders interact with AI tools for business owners.
If you're a business owner trying to figure out how much of the AI wave you need to ride yourself and how much you should hand off, Jay McCauley reveals practical strategies for founders to cut through noise, unleash new productivity, and adapt to game-changing AI and automation, without getting lost in the weeds.
Here’s what listeners can expect from this episode.
You're smart enough to figure out the technical stuff. That's not the question.
The question is whether that's the best use of your time. Jay McCauley describes his role as being someone in a founder's corner, available without scheduling meetings or cutting through red tape, handling everything from backend automations to website builds to ongoing troubleshooting. His clients are already making revenue.
They just need someone to take the technical work off their plate so they can focus on pulling the biggest lever in their business.
Jay only works with a handful of clients at a time, so he can stay heavily involved with them. That means fast turnaround and solutions tailored to exactly what each founder needs. He says: "By working with me, they’re buying back their time to focus on what they need to do in order to move the needle."
Here's a pattern Jay watched repeat itself for over a decade at a software development agency: founders pour tens of thousands of dollars into building something, refuse to release it until it's perfect, and then launch to crickets.
Nobody bought it. Nobody wanted it. And nobody had the chance to tell them that before it was too late.
His advice? “Ship ugly.” Get feedback fast. Every month you spend behind closed doors is money lost and opportunities wasted.
Are you paying $100 a month for a tool and only using one feature?
That's the problem Jay calls "software for one". With Claude Cowork and other AI tools for business owners, you can now solve your one-of-one problem without subscribing to a platform built for thousands of use cases you'll never touch.
Either you build it yourself with a tool like Claude Cowork, or you work with a developer who can whip up a bespoke solution where you're paying minimal infrastructure costs instead of a recurring subscription for the rest of your life.
This is a mindset shift. Instead of thinking about which SaaS product to buy, start thinking about which specific problem you need solved.
Claude Cowork is genuinely useful for low-hanging fruit. Jay gave a great example: give it access to a cluttered folder on your computer, tell it how you want things organized, and it handles the renaming and restructuring in minutes instead of hour (Nick shared a similar win, adding prefixes to 60 or 70 files in Google Drive in under three minutes).
But there's a line. Jay described working with a programmable video editing framework where you can direct edits through natural language. Exciting? Absolutely. Something a non-technical founder should attempt solo? Probably not.
The rule of thumb: if you can fix it yourself when something goes wrong, go for it. If you're swimming further from shore than you can swim back, that's when you call a pro.
Jay is seeing a real shift in what his clients want. It used to be almost entirely done-for-you. Founders didn't care how the sausage got made. They just wanted the output.
Now? More founders want to understand the tools. They want to learn what's effective, get into the weeds a little, and become more capable themselves.
Jay is responding by building out one-on-one guidance for business owners who want to learn how to use Claude Code and other AI tools to optimize manual tasks, replace expensive subscriptions, and move faster.
He isn't trying to turn founders into software developers. He's trying to get them comfortable enough with the tools to see what's possible. Until you've experienced a little of what AI can do, it's hard to imagine where it fits in your business.
"By working with me, they're buying back their time to focus on what they need to do in order to move the needle." — Jay McCauley
"The worst thing they can do is what I call building in a vacuum. If you build in a vacuum, no one can see what you're doing." — Jay McCauley
"You should ship it fast, get it out in public, in front of people, and start getting feedback from them." — Jay McCauley
"If you're paying for a monthly subscription and you're using one feature, that maybe doesn't make sense for you." — Jay McCauley
"The model changes, the tooling changes, everything like that. So I think it's good to at least have a general sense of what's going on." — Jay McCauley
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The Business Owner's Journey Podcast host: Nick Berry
Production Company: FCG
00:00 What a Fractional Tech Partner Does for Non-Technical Founders
02:58 Real Client Projects: AI Tools for Business Owners
06:40 Why Ship Ugly Beats Building in a Vacuum
09:58 Claude Cowork and Buying Back Time
13:26 Software for One: Stop Overpaying for Tools
15:42 Low-Hanging Fruit Wins with Claude Cowork
18:17 Done-with-You: Empowering Founders Through AI Education
Nick Berry (00:12)
Jay McCauley is a fractional tech partner who helps non-technical founders buy back their time by handling the technical work that slows them down.
Claude, Claude Cowork, Claude Code. There are newer and more powerful AI tools dropping every week and business owners are caught between being too excited and too overwhelmed to even figure out how deep we need to go. Expect to learn what a fractional tech partner actually does and why founders need one. Why building in a vacuum is the most expensive mistake that you can make. What software for one means and why you're overpaying for tools that you'll barely even use.
How to know when to DIY with Claude Cowork versus when to hire a pro. The low hanging fruit wins that any non-technical founder can pull off today. Why smart clients are shifting away from done for me to done with you. how to ship ugly without losing your mind. Enjoy this episode with Jay McCauley.
Jay (01:01)
I felt like
business owners needed someone like that where they would be able to come in and help them take care of things on the technical side where like a lot of business owners, you know, that's not necessarily their strong suit. Maybe they're like a great marketer or a great salesperson, sort of thing. You know, maybe they're not as technically inclined in terms of like putting up a website or, know,
doing backend automations to help them be able to run their business more efficiently. And they may not necessarily need to hire someone full time in order to kind of handle those items for them. that's sort of the gap that I fill for the clients that I work with where it's basically just
kind of someone in their corner where they can reach out and get in touch with someone immediately. They don't have to schedule meetings or cut through red tape and try to figure out the right person to help them and that sort of thing. So it's a quick turnaround time. And that's really what I help my clients with.
Nick Berry (02:02)
so what I hear is, for the idea person, right? Who's like, I've got all of these things that we could be doing, but for every one of them, like there's a website that has to be built or an automation that we're missing, or now it's something I want to use AI for, or we need our, the workflow to be connected together. There are all of these things that it takes us about 10 times longer than what probably more than that.
than it would you, and it's not done right when we do it. Then we eventually come and go and find someone who will maybe fix it for us. You are the guy on retainer who takes care of those things.
Jay (02:32)
Yeah. Yeah.
Exactly. the people I work with are very smart. Like they could very well go and figure out how to do the things that I do, but it's going to, like you said, it's going to take them quite a bit longer to do the, technical things that I'm doing for them. So, really what they're doing, by working with me is buying back their time, like buying back their time to focus on.
what they need to do in order to move the needle. And then they tell me like, hey, this is problem I'm having. I don't have the time to fix it. Help me do that. And so that's basically what I do. I free up time for founders so they can go focus on the thing that allows them to pull the biggest lever that they can in their business. I make sure everything is running smoothly, efficiently.
Nick Berry (03:06)
Mm-hmm.
Jay (03:21)
fixing things if and when they come up on the back.
Nick Berry (03:24)
that feels good to think about it. ⁓ So can you tell me about some of the projects that you've worked on with clients?
Jay (03:27)
Yeah.
Yeah, one example would be, I work with an executive coach and he works with founders and CEOs and he also writes a newsletter where he is getting all of this sort of material from his, you know, two plus decades worth of experience being a founder and operator, CEO, and he's turning that vast knowledge that he has into ways that he can help not only his clients, but also help people who are reading his newsletter. So I take that information and distill it into lead magnets in the form of decks that are showing you a very specific process of growing your business or how to hire the right team, how to… properly onboard the people you hire so they make an impact right away, everything like that. So that's an example. And then another example is handling the backend infrastructure of the newsletter platform itself. So doing like A B testing of like subject lines or setting up segments for different readers of the newsletter where You know if a if someone is opening their email, know X percentage of time maybe put this put them in this segment and that sort of thing setting up the lead magnets and automation so the when they Enter their email to get that lead magnet everything fires the automation the sequence of emails goes out properly that sort of thing so that's a couple examples of some things that I do for
a couple of my clients.
Nick Berry (05:08)
it seems like you have some marketing perspective that you're bringing that you can kind of recognize here's what we're trying to create and here's how it's done well.
Jay (05:18)
I have an interesting perspective, I think, in terms of kind of what my background is, because I don't only have a technical background. And in actuality, my technical expertise is something I've started developing more recently. But for like a decade prior to what I've been doing now, I worked in customer success for a software development
software development agency. And so I was working with our clients who were mostly founders, executives, CEOs, that sort of thing, and working with our technical development team. And I was the translation piece between what was happening on the technical side of things and relaying that information to our customers who were on the business side and that sort of thing.
Yeah, I've kind of been working with founders, executives, helping them deliver software solutions and that sort of thing for quite a while. And so I've kind of been on both sides of it where I was on the understanding their business needs and that sort of thing from the client or customer success perspective. And then also understanding now what I'm doing now from the technical side of things. I'm a self-taught full stack developer.
I understand, I think both sides of it, the business side and how the technical sides have to line up in order for the client to get the outcome that they're looking for.
Nick Berry (06:40)
Can we talk about some of the mistakes that founders are making on projects like this?
Jay (06:45)
the biggest things when I was with the software development company
was, and I'm seeing this now they feel that the thing that they're releasing has to be absolutely perfect for it to see the light of day. When in reality, that is probably one of the worst things that they can do because if they are not releasing it and getting feedback from potential customers or current customers, they're not going to know if they like it.
if it's working, what their customers actually want to see in the product. So the worst thing they can do is what I call building in a vacuum. If you build in a vacuum, no one can see what you're doing. No one can see the product, give you feedback and that sort of thing. I would say, it
ship it ugly if you need to. there's a very…
well-known saying from Reid Hoffman, founder of LinkedIn, like you should be embarrassed by the first product that you ship. If you're not embarrassed by it, you have taken way too much time to do it. So yeah, that is one of the things I would say is that you should ship it fast, get it out in public, in front of people and start getting feedback from them. And then you can start fixing things, making it better, giving them the features that they actually want.
Nick Berry (07:59)
How do you get that point across to somebody who has an idea?
Jay (08:03)
It's tough to do because, you know, most of the people that I work with are very high performing and they expect things to be at a certain level and that sort of thing. So it can be hard for the people I work with to do that. They want to, they want their thing to be perfect. And that is definitely not always going to be the case, even if they took, you know, a year developing something and then
put it out there and they could have spent that year building in silence in a vacuum and released it to their customers and then everyone hates it for whatever reason. Whereas if they had released it 11 months ago and started getting feedback from potential customers, paying customers, telling them what they like about it, what's wrong with it, that sort of thing, then
they're that much quicker to really fleshing out what the product is, making those changes, making it better. And it's just a matter of trying to convey that to them where you don't have to be perfect in what you're releasing as long as you are getting feedback. It has to be functional. It can't just be completely not working.
If you get the product into the hands of your users as soon as you can, really, think only good things can happen.
Nick Berry (09:18)
Yeah, because the goal is not a great launch. The goal is to get product market fit as soon as possible, And so when you frame it like that, then it makes it a little bit more palatable to release something that you know you're going to hear about how ugly your baby is sooner.
Jay (09:25)
Yep.
Yeah.
Yeah. Yeah. And one of them, I think one of the biggest takeaways that I had from working at the software development agency was a lot of our customers would do exactly that. They would build something for months, pour tens of thousands, if not hundreds of thousands of dollars into it and not get any feedback from their customers or not release it or anything like that. And then they would
finally be ready to launch and it would be crickets and they would be like, you know, what's happening? Why is, why is no one buying this? Why is no one using it? that sort of thing. So, I've seen it a lot of times happen where, people are burning a lot of money and not getting feedback from their customers in terms of how to, build a product that they are actually going to use.
for the fractional tech partner clients that I take on, I only work with a handful at a time.
Everything that I do is very tailored to exactly what the client is looking for. And I'm the person that's doing all the work. So the turnaround time is very quick and
I only work with a select few number of clients because I want to make sure that that is always the case.
Nick Berry (10:41)
Okay, and are you looking for certain types of businesses?
Jay (10:43)
people that are founders of companies and have a non-technical background. They're making revenue, they have money coming in. It's not just someone with an idea and a prayer of turning something into a business. They have a business that's already making money. They just need someone to help them.
take some things off their plate from the technical side of things and allow them to go out and focus on creating value where they're able to, what their strengths are.
Nick Berry (11:13)
I totally understand the void that that fills
there's always this headache involved in getting, in moving one of these projects forward. And I'm glad to see that someone is solving that.
Jay (11:19)
Yup.
it's been very worthwhile and, ⁓ building the business that I am working with very smart entrepreneurs every day on a daily basis,
Nick Berry (11:34)
congrats, man. And thank you again for doing this.
Jay (11:37)
thank you very much. Appreciate it.
Nick Berry (11:39)
So we just, just had our initial interview like days ago, then, Claude cowork comes out. It may have already been out, but there was, a, a weekend, and.
Everything was different on Monday and everybody's talking about Claude. Cowork and even, Ali Abdaal even mentioned it last week. He said two weeks ago, my sleep scores were perfect. Claude cowork comes out the next week. My sleep scores are terrible
I dove into it and it's so interesting. So I wanted to have you come back and about it a little bit more because I think we agree there's definitely potential business owners. cannot ignore it. There's plenty of reason to get excited and
get drunk on the idea and kind of get lost in it. And I think the challenge for everybody is figuring out like, how much do I need to know about how much do I need to try to do for myself and how much do I need to like, just go to a pro and get them to do it. And so Jay, you mentioned to me this software for one idea and it makes total sense. So would you start explaining that?
Jay (12:42)
Yeah.
yeah, it seems like the pace at which things are new technology is coming out is just getting faster and faster. It's kind of hard to keep up. And like you all of a sudden, Claude code was everywhere over one weekend. And, that was kind of the main topic for everyone. But with with all this new technology, I think one of the things that
is worth looking at the tools that you're currently using. you're paying for a monthly subscription of $100 and you're using a product where you're using one feature and paying $100 for it, that maybe doesn't make sense for you. And we're coming to the point where either you yourself, if you're not technical, can get into the weeds a little bit and
try to play around and start building your own things and solve your one-of-one problem. Or you can work with people who are developers or that sort of thing and say, hey, I want this one feature. I don't want to pay $100 a month for it. And they can whip something up for you where most of the time it's either free or you're just paying for the very minimal infrastructure costs to maybe host the app or
couple underlying tools that power it, but you're not paying $100 a month for the rest of your life to have access to this one feature that moves the needle for you.
Nick Berry (14:04)
have you had a lot of people reaching out to you since this last little buzz around Claude trying to figure out like what do we do with this?
Jay (14:11)
I have and yeah, it depends. I think it's different for every situation where if you are someone who likes getting your hands dirty, kind of learning new things and has the time to do it, it's I think it makes sense to at least start sort of familiarizing yourself with these new tools, whether it's Claude Cowork, or if you want to dig in a little further and start.
playing around with Claude code and that sort of thing. You can do that if you have the time and interest to do it. If you don't have time, then I think that's where it could make sense to find someone who specializes in things like that. someone like myself or other developers, they can teach you or they can just build sort of bespoke custom solutions for you.
Nick Berry (14:53)
Yeah. I mean, you need to know something about it. You need to be, to be learning and trying to keep up at least on the surface level. But the real question is like how deep to get in because it is bottomless and it's going to keep coming. let's not think that this new newest version of Claude is the end game here. It's going to be the thing that everybody's lathered up over for a little while until there's a next thing.
Jay (15:16)
Yeah. Yeah.
Nick Berry (15:17)
it's probably going to be
another level up from there.
Jay (15:20)
For sure. something is literally coming out every day. Like the model changes, the tooling changes, everything like that. So I think it's good to at least have a general sense of what's going on. not have your head completely in the sand. even myself,
something new comes out every day, I don't pay attention to every single thing. When things start getting a little traction that's when I kind of dig in a little bit further.
Nick Berry (15:42)
Yeah.
let's talk about things that you should, are probably worth a rookie or new getting in and trying to do themselves or learn about versus the things that you might think it would be fun, but it's probably just not worth your time to do it.
Jay (15:58)
one thing Claude Cowork is very good at, I think we're all a little bit messy and cluttered in terms of organizing files on our computer or something like that. one thing that's a great example of what you can do with Claude Cowork is just give it access to a specific folder on your computer where you know you need to
organize it a little better, rename some things, that sort of thing. And it will, you can just give it the output that you want. you know, every file that pertains to so-and-so should have this prefix with it or whatever the case may be. You can give it access to that folder. It will go in and automatically start cleaning up your file names. could create new folders within that folder,
organize things by subfolder, that is, that's an example of like a low hanging fruit thing you can do where that's a very simple thing. You can offload to something like Claude Cowork. You don't have to like outsource that to someone else or you don't have to spend, you know, an hour doing it yourself. You can talk to Claude Cowork, give it that prompt and have it done in a matter of minutes as opposed to hours trying to do it manually yourself.
Nick Berry (17:07)
And you worst case scenario, you could probably fix it if you had to. Right. Like that's, that's a big thing that scares me is I can build well beyond what I can maintain. It's like I can swim very far from the shore, much further than I can swim to get back.
Jay (17:13)
Yeah.
I
Yep. uncomfortable about getting a little out in front of your skis, maybe one thing you could do is reorganizing files or folder names or that sort of thing. You can make a duplicate of it. you know that if something catastrophic happens that you don't have any idea what is happening and it deletes some important files or something,
then you've got the backup. And then you can also just tell it to, like, if something happened, be like, actually, I did not want you to do that. Revert the changes you just made, and it'll go back and reverse the updates that it did, as long as it's not something catastrophic you did, which typically is not something that's going to happen.
Nick Berry (18:05)
so the file organization, think that's something that it just makes sense. it's a pretty safe project and it's, definitely helpful. And then, something I use it for pretty regularly is just creating scripts for.
Jay (18:11)
Yeah.
Nick Berry (18:17)
Google Drive, Google Sheets, I renamed probably just added a prefix to a folder 60, 70 files in it earlier this week that would have taken, I don't know how long it would have taken, an hour to do that, one at a time or close to it. And it probably took me 30 seconds to tell Claude. It probably took Claude 10 seconds to give me the answer. And then,
Jay (18:18)
Yeah.
Nick Berry (18:37)
within a total of three minutes, the job was done. That was faster than me even telling somebody else to do it. So those are the type of things that I think are like nice little baby steps, but you were telling me about a project that, that you had that I think is like a good example of.
Jay (18:44)
Exactly.
Nick Berry (18:54)
something that it's exciting. It's, it's valuable. It's something that a business owner might think, you know what? I can, I'm going to go and I'm to have it make me those things. And that's where you in that gray area though. It's like, I don't know, man. You maybe some things you just want to get a pro to do.
Jay (19:03)
Yeah.
Yeah. So it depends. Like there's certainly levels with either comfortability or time you have to spend and that sort of thing. So one of the things that I've been playing around with is there is basically this coding framework that takes video editing software and essentially turns it into programmable commands.
So instead of, you're a podcast producer, you do video content, everything like that. People like you are paying for video editing software and maybe, you know, paying teammates and stuff to do that stuff for you. One thing you can do is like you can essentially use this video editing software, which is free to use and essentially have a conversation with Claude or
plug code if you want to get a little bit more involved in it and you can just tell it in natural language the edits that you want to make to the video what kind of style transitions everything like that and you can literally just type out sentences and have it edit the video for you so definitely some interesting stuff there yeah
Nick Berry (20:10)
Absolutely. Yeah. I mean, you can't ignore it. is like some of the familiarity, how much of this, you're going to start doing some type of guidance for business owners who are wanting to get into doing some of this on their own, right?
Jay (20:22)
Yeah. Yeah. So, you know, kind of what I've learned over the last year or so working with, with clients, like building software solutions for them, that sort of thing. There are some where like, they want to be completely hands off. They don't want to know what's going on. They don't want to know how the sausage is getting made. They just want to, you know, have the end result. And what I've come to, what I've been seeing more recently is like,
Like you were saying, everyone was talking about plug cowork and that sort of thing. Some of them are very interested in learning what tools are effective, how they can use them themselves to become more effective in their business and make their lives easier. yeah, I'm recently going to be starting to kind of show people and work with them kind of on a one-on-one basis.
kind of learn what they're struggling with currently or what is sort of manual tasks that they think can be optimized by some of these new tools and then working with them and teaching them how to do that. if it's, know, if they're making video content, editing their videos, like show them a way to do it much more effectively or use a free tool as opposed to
you know, paying a huge monthly subscription for something that they don't necessarily need. So what I've seen more recently is like, it's shifting a little bit from a done for me thing where like everyone wants to just have the output and they don't care about learning what it takes to get there. And it's shifted a little bit more to done with you where like they want to start learning how to use these tools, start getting into the weeds a little bit. Like I don't think they want to become
software developers if they're not currently, but it's just being more comfortable using these tools effectively.
Nick Berry (22:05)
And being that getting comfortable doing what you're talking about also kind of enlightens you as to what the possibilities are. Cause as much as anything, that's where our minds need to be right now. It's not like if you're, if you are the business owner, you can't just expect that someone's going to show up and say, here's what you should do now. Right. This is, ⁓ it's you need to be kind of applying your imagination and, seeing where do you think.
Jay (22:13)
Yeah.
Yep.
Yeah.
Nick Berry (22:31)
what could it do for you? And it's hard to imagine until you've experienced a little bit of it because we don't have anything else like this.
Jay (22:38)
Yeah. Yeah, think, yeah, for sure. It's there's a lot more to interacting with like, like chatbots, like Claude or chat, GBT, that sort of thing. lot more to it than just asking it random questions and treating it like a, maybe a different version of Google, like a
Nick Berry (22:39)
So.
Nick Berry is an American entrepreneur and business advisor, whose track record includes founding, leading, and advising award winning small businesses since 2002. He has built companies in multiple industries, hosts The Business Owner’s Journey podcast, and created the Business Alignment System™ framework that helps owner-operators scale without burning out.
After his most recent exit he founded Redesigned.Business to advise and coach to other entrepreneurs and business owners who are looking for a trusted (and proven) advisor.
Among peers, colleagues and clients, Nick has been referred to as 'The Anti-Guru', due to his pragmatic approach and principled leadership. He shares his thoughts, experience, and lessons learned each week in The Golden Thread newsletter.
