Skip to content
upshift
All press

PodcastThe Polaris Signal

AI Won’t Replace You. Your Business Model Will.

Shawn Yeager with Jason Keil

Jason and I worked through what AI is doing to small and medium businesses: what it breaks, and what gets built in its place. Outcome pricing, the innermost loop, vibe-coding a tool in an afternoon, replacing the bookkeeper with an agent. And why the taste and judgment you’ve already built up still beats the tools.

If you’ve been selling hours, things are going to get rough.

Chapters

Selected passages

On where the value sits once AI handles the mechanics (10:17):

Make no mistake — it’s not the lawyers. It’s the deliverables and the outcomes. That’s the shift for professional services firms: you’re selling outcomes.

On the innermost loop, the thing AI can’t strip away yet (14:30):

You look at any operation as consecutive rings of loops. The outermost ring is how you interact with the client. You move further in to the innermost loop. That’s the real value. Everything else is going to get stripped away and automated. So what is that innermost loop? What is the thing you deliver that cannot be automated away, at least not yet?

The written version

In writing I’m more direct about the math. Billable hours don’t survive what AI is doing to margins, and the venture money piling into professional services is no longer subtle about it either. The response is 2–3 new offerings rather than another tool to adopt.

Transcript

Shawn: Jason, how you doing?

Jason: I’m good. How are you?

Shawn: I am well. Thanks for having me.

Jason: Good man. Thank you for being on. I am so excited to have you on. So this is a newer podcast. I’m calling it the Polaris Signal. Polaris being the North Star, which has been this guiding beacon for wayfarers throughout time. It’s a changing time right now in business. Times are changing.

Jason: And my goal is to have folks like yourself, experts on who can kind of bring some signal to the noise. So why don’t you just maybe share just a little bit about yourself and your background. I know you well, but. Yeah.

Shawn: Yeah, I’ll try to give you the TLDR. So I have spent 30 plus years in emerging technology, frontier technology, new technology on the commercial side of things. And generally my work, the through line through it, ranging from early web to cloud to mobile to SaaS to Bitcoin, now AI, has been

Shawn: What breaks among the commercial machinery that came before and what has to get rebuilt to make it work. And so that could be, know, what did the web do to advertising? What has Bitcoin done to payments? What has now AI done to most everything? And so what I greatly enjoy and where my work generally is, is how do you take those things, package them, price them, get them to market, reach new customers, generate new revenue?

Shawn: Now, in the meanwhile, I love to build with it as well. So I’ve spent this last six months pretty deep down the AI rabbit hole, like most people. Way too many hours, way too many tokens, but it’s been incredible to sort of get a firsthand experience with what’s possible.

Shawn: So you were early with the web, with Bitcoin, with AI. What does that feel like when you can see what’s coming so clearly? Is it kind of isolating when maybe not everyone else feels and sees what’s coming in the same, like, tangible way as you?

Shawn: Well, I’m not quite Elon, but I would imagine that feels very different. But from my own sort of humble perspective, I think it’s invigorating. Think it is, it’s a personal motivator for me. It’s what has, since I got my first computer when I was eight years old, that has been consistent, which is wow, this is a gateway into something new. And what does this make possible? So more specific to your question, I would say that is.

Shawn: Largely about pattern recognition. Think, I’m a gray beard. So as you get a little older and go through a few of these waves, you see, OK, well, though I think AI is the most consequential technology of our age, as a Bitcoiner, I look forward to it becoming the most consequential technology as things develop. But I think here in the now, AI is just on everybody’s lips. So what’s so interesting to me about that?

Shawn: Is what does it do for our better angels? And there are a lot of ways to misuse and abuse technology, but generally, I see it as neutral, and it’s a matter of how we apply it, and that is probably what’s most interesting.

Shawn: Is there a heuristic that you use for pattern recognition?

Shawn: Hmm. I’d like to claim I have one. I think it’s maybe just accumulated experience. I think it is human nature. I think what does it push and pull and tug on in us as humans? I was having a conversation over lunch with a couple of our fellow friends and colleagues about AI as well. And.

Shawn: One of them, I won’t dox him, but he was sharing that he woke up in the middle of the night last night and literally wrote a poem about AI and the crux of it was that all that is left that it will not, cannot touch is what does it mean to hurt and to lose and to reconcile and to hug and to, not to go too far down that path, but the point being is it appears that it will affect most everything. And so I think to your question, the heuristic,

Shawn: I think is what for me is what does it break and what does it make possible and what do we

Shawn: So, this podcast is just kind of getting off the ground, but my goal is that- Congratulations, by the way. Thank you. And my goal, though, is to get some signal into the hands, particularly of the small, medium-sized business crowd. Times, as you’ve mentioned, are changing very rapidly. And when the sand is, shifting underneath our feet, having that ability to…

Shawn: Process pattern recognition and to know In what ways should we be moving quickly and in what ways should we just be waiting? Right and how do you how do you kind of pull out the pieces because it’s The problem with the internet is that yes, you get access to lots of information more information than Clinton had when he was in presidency like right here in our pockets, but

Shawn: With that information comes oftentimes too much information. And so how is this relevant for a small and medium sized business owner and what do they do in this time of AI?

Shawn: Yeah, well, I have some pretty strong opinions loosely held about that, just because I’ve been looking very closely of late at which sectors are likely to be most significantly affected. I think professional services is right in the crosshairs. I’ve actually been working on a talk to deliver to some groups called AI killed the billable hour.

Shawn: That is the crux of it, right? I think if your business model, be it law, accounting, marketing agencies, engineering, architecture, consulting, this is going to change. And so I think to answer your question more directly, I look at it through the lens of business model transformation. AI is likely the most significant of our time, but it is in a way just yet another

Shawn: Transformation, another disruption, another creative destruction, call it what you will. So I think for small businesses, medium businesses, if you’re a big four, you’ve put, in fact, collectively $10 billion into AI over the last three years so they can go down market. If you’re a small to medium business looking to survive and thrive, I think the best thing, the most important thing you can do, and you touched on this, Jason, is not pay so…

Shawn: Not pay such close attention to the version of OpenAI or whatever Nano Banana, whatever is next that I’ve got a few of running, we probably most of us do, it’s what does it do to your business model, right? So not how do I automate and save so much as what do I do to generate new revenue with new offerings, new products. That to me is the focal point.

Shawn: Okay, so rather than having, to me, it almost sounds like you’re saying rather than having a fear-based mindset, having a mindset of abundance, rather than time to slash and burn costs and fire all my employees, instead, what else can we build? Can we twice as many videos? I saw that example this morning. Absolutely.

Shawn: Yes, and think there are, there’s no doubt that, and I don’t at all make light of this, they’re going to be, they’re going to continue to be tens or hundreds of thousands of people displaced, put out of work, fired. From the standpoint of a business owner and operator, there undoubtedly will come some hard decisions about how that plays out. But yes, I think,

Shawn: It isn’t so much how do I cut staff and cut costs. It’s what can I now do? What sorts of, if you’re an accounting firm, can you deliver 24–7 compliance to a particular set of IRS regulations? If you’re a marketing agency, can you spin up a brand manager per client that runs 24–7?

Shawn: And that’s not an hourly offering. And so it’s easy to say, it’s a little more difficult to build, but these are things that are being built. And there are companies, not to sort of wave the sickle around, but there are companies out there raising hundreds of millions of dollars to automate away entire sectors. So another way of saying, certainly develop some capability and some fluency.

Shawn: With these technologies, but I think it’s also to sort of step back, assess what you deliver, how you deliver, who delivers it, and think about how you can compress the costs, yes, but also expand the offerings and hopefully revenue as well.

Shawn: I like this framing of it’s not that you’re necessarily going to go out of business, but that your business model is going to need to change. That you can thrive during these times of significant change, but you’re very likely going to have to reassess your business model and be innovative in that sense. How urgent of a problem is this?

Shawn: Well, I’ve got some research, and I’ll share it with you for the show notes perhaps, to demonstrate how many tens or hundreds of millions of dollars startups are raising. For example, I think it’s Harvey, if I get this correct, just acquired a law firm, or multiple law firms. And so this is an AI legal product who are now gobbling up law firms.

Shawn: The product, make no mistake, is not the lawyers. It’s the deliverables and the outcomes. And again, easy to say, but I think that’s the shift for professional services firms is you’re selling outcomes. And if you’ve been selling hours, things are gonna get rough.

Shawn: I like that shift. You’re selling outcomes. And so how do you find a pricing model where you are compensated for your outcomes? I would be nervous if I was an employee of that law firm getting acquired by Harvey.

Shawn: Yeah, I would too. And I think I hear tell of, pardon me, some very smart people in our circles that are building products to address this and getting out ahead of these changes. And I’m reminded of, I forget who it was, someone on LinkedIn, video influencer, know, one of the hustle culture influencers, know, and her point, however, was I think valid, which is she said something to the effect of,

Shawn: Imagine that 30-year-old, fresh MBA looking at the HVAC company without a website and salivating, right? And I’m misquoting, I’m sure. But the point is, that’s an opportunity, right? What are the things that AI will not touch until Elon rolls out his 10 million robots, right? I’ve still got to hire somebody to come fix this thing.

Jason: Right, so let’s talk about that for a second this HVAC example. Let’s say you run one of those HVAC companies and Your website you built a decade ago and you get the calls every day and you go service the HVAC units and you hear about AI and you’re like I Use it as Google. I can ask questions and it tells me answers. Yeah, yeah, I got chat GBT on my phone What do you do like, you may not understand

Jason: How this impacts your business quite yet and what you should do about it and why some software company would wanna, or an MBA student would wanna like acquire that. Like what are the ramifications for that owner? And what does one do?

Jason: Well, I’m reminded, this is a trivial example, but a friend of mine reached out to me not long ago and said that he in turn has a friend who’s got a handful of small lawn care, single solo double operators, and he sort of collected them together and is building a bigger business. So in…

Jason: Few hours and this is not go me this is a salute to the tools I built a simple progressive web app that has one button that you smash and it says start and it because of geofencing it knows where you are and when you’re done mowing and trimming and doing whatever you hit stop and behind the scenes it pulls everything in to generate invoices take payment the whole deal and this is this is a guy doing this in an afternoon for a friend of mine but that’s very doable right so

Jason: I guess if you’re that HVAC owner, you probably, to use the phrase, know a guy, or can find someone who can build that for you and can give you a little bit of an edge, right? Can help you reduce the back office complexities. That create a thriving business? Maybe not. Does it keep you in business? Probably so. And I think, I think it’s Peter Diamandis.

Shawn: His substack references the innermost loop. And the story as he tells it, if I understand correctly, is you go to any operation and you look at these consecutive rings of loops that sort of run. The most outermost ring is presumably how you interact with the client, service the customer, all that. You get further and further into that sort of inner ring, that innermost loop, and that’s the real value. And his message, if I take it correctly, is everything else is going to get stripped away.

Shawn: So what is that innermost loop? What is the thing that you deliver on that cannot be automated away, at least not yet? And that I think is where you have to really focus and then look to be able to automate away the rest to at least keep up if not get

Shawn: Yeah, like I think of customer service having like responsiveness and that human touch. Yes. I don’t know that AI is ever going to replace that.

Shawn: Interesting. So, Fin, went from zero to $100 million in revenue on outcome-based pricing, I think, over the last 18 months, if I get that correct. Now, it is that chat bubble in the corner of the browser, right? That is not the way I want to interact with a company if they just broke my dishwasher or whatever it is, right? At least, probably not, if I had my choice. I’m an older guy, maybe I’m outdated in that regard, but…

Shawn: You know, the point is they now have fully automated away their whole product now is agent based. And that will only fit a certain set of products and industries and customer segments. But absolutely, I think there are others where it’s high touch, right? And you have to keep that high touch.

Jason: I don’t want a SaaS company replacing my HVAC unit. Nor can it. No.

Jason: No, or, and unfortunately, much to my wife’s chagrin, I’m not handy, so I have to know a guy, I have to have a guy. And having someone who’s a trustworthy handyman. I think my last quote was 125 an hour. Pretty good, right? So what does that say? That says that we will, the market will.

Jason: Will orient toward those sorts of skills that I can’t go write code. I can’t get Claude Code to do that.

Jason: So you built in an afternoon for your friend who runs lawn care. Yes, lawn care business. Within an afternoon you built software that has a timer, geo-fencing, invoicing and payments. How did you do that? And how did you implement something like payments, which has…

Jason: Who in turn has, yeah.

Jason: It’s not just software. There’s regulatory products involved and KYC involved and

Jason: I’d love to say it was Bitcoin. It was not, it was Stripe. And so, whole other conversation, whole other podcast maybe, just, with self promotion, but I just published a piece this morning called the CLI is the new API and command line interface, not to get in the weeds, but for anyone who’s a technologist or a builder,

Jason: It is now about optimizing for what agents can consume and drive and puppeteer. And so companies like Stripe have done a brilliant job of making it very easy to direct something like Claude Code or Codex or whatever your tool of choice is at that component, that interface, that tool, and wire it together. And so the shorter answer to your question is, because it is so straightforward, because it is so easy to consume and use, it was Stripe.

Jason: And so with all of the attendant mess that goes with that and the fee structure is, you better than I do. All of the downsides, it was a few hours work from zero to here. Use it. Now, does that mean it maintains itself? There’s all that goes with it. It was workable in an afternoon.

Jason: Yeah, so I think that is one of my… Now, I’ve gone past the honeymoon phase with Claude Code and these different tools, and that’s where I get frustrated with AI, and I’m like, we’re not there yet. This is not as revolutionary as we’ve been told it is. In many ways. The security, the maintenance, and the details. Yes. Once you start to use the product, it’s really easy to get…

Jason: A brand new website, a brand new invoicing tool, whatever it is, like can build whatever you wanna build. But the security aspects and then every little detail, once you begin to test it, it doesn’t seem to work. How long do you think we have until this is actually like truly disruptive and regular small business owners can build their own tools?

Jason: Well, in that I take two questions. The first is how long until a certain type of builder can close the gap on that last, that the Pareto, that last 20 % is brutal. That is shrinking rapidly. And there are professional software engineers that I read generally daily who just don’t write code anymore. You know, they write prompts.

Jason: And I’ve got to, I won’t bore you with the details, but I’ve got a set of plugins and skills now that have become my tool belt. And would I, would I build a Bitcoin wallet and put it into production? Hell no, because I’m not a professional software engineer. Could I get it 95 % of the way and then go higher? The final five? Yeah, I still wouldn’t probably do it. I’d rather run Sparrow. But the point being for something that is not mission critical.

Jason: I can get 98, 99 % of the way there.

Shawn: For a non-technical, and my background is a study of computer science long ago, and I’ve stayed pretty close to the keyboard for a long time. So I’m not a developer, but I’ve got that background. For someone who doesn’t have that background, I think the greatest glimpse of the future that I have seen is Perplexity Computer. So they took an interesting naming strategy, and they have in fact wrapped all the other products. They’ve wrapped.

Shawn: Gemini and Claude Code and OpenAI Codex and all this. And they put this phenomenal container around it that sits on your desktop and will do just about virtually anything. It’s amazing. Their downsides, it has to stay in sort of their little container and they host it. There’s all these caveats. But the point being for a business owner who wants outcomes, who wants to be able to point a tool, an agent at a folder full of invoices.

Shawn: Or pointed at a folder full of emails and say, know, replace their bookkeeper, sorry bookkeepers, that’s gone. Or triage a bunch of emails, like any of those sort of very, day in day out kind of operational, build a dashboard, right? Build a personal health dashboard. Take my Garmin data, take my everything,. Those tools are great for it and they’re getting better.

Shawn: So in other words, I think for a small business owner who’s got plenty of other things to do, I think perplexity computer, I’m not plugging, but I think it’s a strong indication of where we’re going. Claude Code is another. My wonderful wife who has a master’s degree in artificial intelligence but doesn’t want to touch any of that anymore, she’s the best and she’s at home with our son. The point being, she hasn’t looked at it in two years.

Shawn: Since she was in it professionally last. And three, I guess. But the point being, I finally talked her into sitting down on her Mac and I installed Claude Code, and now she spends 30 minutes in the morning basically setting up a list of work for it to do for a business she’s working on. And so, that’s just another little sort of anecdote for that’s the kind of tooling I think a small business owner needs and has soon, if not already.

Jason: So you mentioned the bookkeeping example. Every small business owner I know has a bookkeeper. And whether it’s in-house or they use a contractor, but you said it’s going away.

Jason: Well, no, I’m not an expert. I’ve never worked as a bookkeeper, never owned a bookkeeping firm or an accounting firm, but I think it’s the kind of work with all due respect. Think bookkeepers have saved all of us at some point from grueling, grueling labor. It is just so easily automatable today. I have a friend, I’m thinking of in Toronto who…

Jason: Today. What do you do?

Shawn: Has a portfolio of small businesses, products mostly, and he replaced his, if he told me the numbers correctly, his $15,000, $16,000 a year bookkeeping service with an agent. And so he just dumps all of his PDFs, all of his emails, all of his documents in a folder, and it just sorts it out, and preps it for his accountant.

Shawn: Can you connect like, Clawed MCP to QuickBooks Online or what? A lot of folks are using QuickBooks Online, they’re not necessarily just uploading invoices to like, some software they’ve built themselves or whatever.

Shawn: Yeah, and a great question. I don’t know. I have to assume that Quick and QuickBooks has a series of APIs. And I’ll use this slightly aside as an indicator. Of all companies, Visa, if you go to VisaCLI.sh, they kind of half shipped a CLI. Know, and- Work.

Shawn: So.

Shawn: It’s not altogether clear. But the point is you can now point an agent, you can install their command line interface tool, which for those who don’t know, a CLI is the oldest of the old ways of interacting with software, which is that you’re at a so-called terminal and you’re typing commands and you’re typing dash F and space this and that, and it’s archaic and terrible by some people’s measures. But lo and behold, fast forward.

Shawn: Because it is deterministic, because it is strictly typed and all these other things, an agent, another piece of software can understand it quickly and can make it do what it needs to do. So even someone as stodgy and incumbent as Visa saw the writing on the wall. Stripe is.

Shawn: I’m sure they’re making tons of money off strike, right? I don’t know that you would know the numbers. I don’t know the numbers. But they even apparently, know, perked their heads up and said, crap, we gotta get on this. And so that’s to come back to your question and say, go, I have to believe that QuickBooksQuicken has done it or is doing it. I don’t know how my buddy does it, but I know that he’s replaced his bookkeeper.

Shawn: It’s interesting that archaic software is now running.

Shawn: The future. Right. Well, and you saw this when, when Anthropic announced that they could, they could modernize COBOL, which for anyone from the sixties and seventies, that’s, that’s software from the sixties and seventies that now runs, still runs an insane number of core systems and banks and government and all this – IBM stock dropped 10% on that day as a direct unequivocal, result of Anthropic saying,

Shawn: We will now do what you bill out, professional services, to the tunes of hundreds of millions of dollars a year to do, we can now do.

Shawn: So it’s coming for everybody.

Shawn: Are Visa and Mastercard gonna go away?

Shawn: No, mean, well, and I think, and I’m sure I have borrowed this from other very smart people, but I have certainly come to understand and appreciate that the enduring moats of any technology firm loosely said, we put Visa, mean, MasterCard at least I think is a data company, right? They make most of their money on data, but if we put them sort of in the loose category of technology,

Shawn: It is data, networks, go to market. That’s how you win and stay alive, or stay alive and win. It isn’t software anymore. And so they have tremendous network. They’ve got all the data. And they’re already distributed everywhere. If I had to pick, I would pick Ticketmaster. But maybe Visa Mastercard after that.

Shawn: Comcast.

Shawn: Couldn’t go away fast enough.

Shawn: So.

Jason: And you think you think Visa will retain its market share in comparison to stable coins and Bitcoin?

Jason: Now that to me is a different question.

Jason: Well, the first question was all or nothing. Will Visa die? And that’s a pretty obvious answer, no time anytime soon. But the more accurate answer is ratios, I guess.

Shawn: Yeah, and I think here too, I’ll plug my Substack, which is just sideband.pub, you can plug it in there. For me, it’s mostly just sort of thought experiments. And so one of them is about agent payments and my application of the three body problem, which is that on the one side, you’ve got incumbent capital and the state, which operates sort of as this binary.

Shawn: Regulation creates moats, those with the moats lobby for regulation. It sort of feeds on itself and you’ve got, the visa, the mastercards and all the rest on the other side, I put insurgent capital, which are those who want Bitcoin, not just want, but are, are, putting money where their mouth is putting up capital to help Bitcoin win to a degree stable coins, et cetera. And so, if you look at x402, which Stripe coin base and others are

Shawn: As an agent to agent payment protocol. If you certainly look at where it seems the winds are blowing in the United States federal government, stablecoins would appear to be the victor at least for the foreseeable future. I think we both hope that eventually settles out to Lightning and Bitcoin. In as much as the regulators continue to be the choosers of winners and losers, I think it’s probably stablecoins. And then back to your question.

Shawn: I just have to think that Visa MasterCard will keep their fingers in the pot somehow. But I think the thing that I sort of looked at ultimately in this piece is left to its own devices, and Bitcoin Policy Institute did a great piece of research here. If agents not the anthropomorphize them too much, but if they are left to their own sort of optimization for speed and low friction,.

Shawn: Course they’re going to choose Bitcoin, Lightning, Cashu. Barring that, probably stable coins. Are they going to sign up for a Stripe account? No. So some humans still got to give them a Stripe account. So to me, I think ultimately that’s what’s interesting is to…

Shawn: Look forward to or to look ahead and see will the additional drag and friction that KYC, for example, and the regulatory regimes create, will it be sufficiently painful to those putting hundreds of billions of dollars behind AI? Or will the continued use of Visa and MasterCard and other fully KYC’d and high friction networks just be a cost to doing business?

Shawn: Yeah, until KYA becomes a thing or KYAI, I’m sure. I’m sure like they’re not going to be able to sign up for a Stripe account because of regulation like the federal government requires to have a background check and the social security number and all of these things to ensure there’s no open bankruptcy and fraud and all that.

Shawn: I’m sure somebody’s working on it.

Shawn: Meanwhile, I built a skill that can bootstrap an agent onto Nostr with its own cashew wallet in five seconds. And again, it’s not some magic I did, it’s just doable. So on the one hand, I had to give it the 100,000 sats to start with or whatever, but that can happen. You can say do this and it will download a skill, get up and running. Use a single mnemonic to set up its wallet and its Nostr public-private key pair, and it’s got an identity and a wallet and off it goes. And it’s buying things.

Shawn: That is real today, thanks to calle and others who built Cashu and similar technologies. FiatJaf for Nostr versus Stripe. So those are the two poles.

Shawn: Yeah. I think you’re right about the incumbents having they have so much power and the regulation. That’s a big part of why I made a pretty radical financial decision and started selling rental properties to buy Bitcoin. And initially it was like a ratio, maybe 10 percent. It just ended up being, all in. But in part, it was because the ETFs were approved. And I felt like, OK, if Wall Street’s in. Right.

Shawn: Those guys have. Yeah, yeah, these are no longer like just guys like in their basement,. Correct. Yeah. And so I think of along the same lines, I guess, with AI and payments and some of these changes that are taking place. So if you’re a small business owner. A lot of these terms, I think, are probably over your head, agents and all of that, like, should I?

Shawn: Tail risk is now significantly diminished.

Shawn: Internet.

Jason: I run a payments company, like what should I do? Should I set up an agent? I’m not venture backed and have like thousands of employees. And I think there’s so many of like the HVAC company and the auto repair shop and the dentist and all of that, where they are providing their product or service. And a lot of this stuff is just over their head. And so where are we at today in terms of the relevancy for the everyday business owner?

Jason: I have shared this story with a lot of people recently because, and I should remember, it is a brand new substack by a fellow I have followed for a while, and he calls it Near Zero. And the reason, I believe, is because he’s writing these future fiction tales of what will happen when the marginal cost of technology approaches zero. And so he tells this story, I’ll try to do it justice,

Jason: Of some time in the near future in a Midwest farm town when a woman, a farmer, who has automated her crop irrigation and any number of other systems by vibe coding. She’s vibe coded a bunch of tools that have genuinely and materially improved her life and her business. And so this particular example, I believe, is the irrigation system is connected to satellite data.

Jason: The satellite provider changed the data format and it broke everything downstream, which goes to the maintenance question that few of us talk about. Like you can one-shot or vibe code something, but then you gotta feed the thing, right? You gotta keep it alive. And so the protagonist of the story is a guy who operates out of what was Ted’s tractor repair, and now it’s Ted’s AI repair. He is an AI mechanic. And so he comes in.

Jason: To help her break this, or rather fix this system that has broken, not by any of her own doing, but just by the mere fact that the data format changed and nobody kept tabs on it. So my point to that is, think there are now or will soon be material benefits to just about any business if you think through who supplies to me the data that drives my business, right?

Shawn: Could I cut five hours out of my work week by taking some auto parts supplier who’s got some janky website who sends me an Excel spreadsheet once a week that I have to pour through or hire someone to look at and check against inventory and I’m sort of making this up, but it’s generally grounded, I think. Could I?

Shawn: Myself or I know a guy, I’ve got a nephew, whatever that situation is, which soon we will all have that niece or nephew who could spend a few hours and wire those things together. And there’s five hours of my week back. So it may change nothing about the front of house, so to speak. It may change nothing about what happens between the counter, the service counter, and the customer. But then again, maybe, maybe it does for you as a small

Shawn: Automotive shop what the dealers and the manufacturers do today, which is to be preemptive, right? And to, certainly Valvoline sends out their mailers and all those things, but I’m thinking of like the small, smaller mom and pop shop who can create higher touch. They can create lower friction. They can automate away some of that back office mess. So I don’t have terribly specific answers, but

Shawn: I am confident that if you do two things, one is you look at what delivers the most delight and the greatest outcomes and benefits to the customer, and you go hard on that. And then you look at where all the cost and complexity and friction is, and you map that to what AI can tackle and automate away.

Shawn: This is why I brought you on, I think this is so helpful. This, bringing on these two concepts of high touch and delighting your customers. It doesn’t matter what industry you’re in. If you can delight your customers and not just, high touch may be the wrong term, but emotionally touch them where they leave feeling like someone cares. I…

Shawn: Absolutely not.

Jason: We’re so far away from AI ever touching. And at the same time, if your back office, your spreadsheets, your PDFs, your admin, if you can just get started with automating some of that away, and maybe you don’t know, but I think for me personally, one of the biggest tools which you are helpful bringing this tool in my tool belt is just asking, but…

Jason: But not necessarily asking random people, just ask the AI and keep asking. So while you could do this, this, and this, those terms are over my head. What does this mean? What does that mean? I don’t know what a SQL database is. Tell me more.

Jason: Or invert it and not to interrupt you but I would say the other big thing for those who are dipping their toes in Have it interview you right? So if there is a workflow If there’s just something, I receive and I keep I keep coming back to that example I’m thinking about automotive suppliers. I don’t know. Maybe they’re all maybe they’re all integrated now, but I doubt it and so if you receive ten Excel spreadsheets a week and you’ve got to manage those deal with those

Jason: Deduplicate those, copy paste those. That’s trivial, right? So jump into Claude Code or ChatGPT and say, hey, I have this workflow. I have this situation where every week I receive 10 Excel spreadsheets, and I’ve got to do x, y, and z. I’d like to automate that away. Interview me for any questions you have that are not answered in what we just discussed.

Jason: And then let’s build a project to do that. And so the whole takeaway there is something as simple as having an interview is great. And then it could be you walking around with your phone doing speech to text out in the backyard, sipping a beer, doing whatever you want to do. And then you dispatch it to go build something. And nine times out of 10 these days, it’ll get it right.

Jason: Fascinating. One of my challenges, just personally, is that we have to be really careful with what we give AI for security reasons. I’m in payments and we deal with sensitive data. So, I don’t know what the answer is there for folks that are having to be really cautious about what kind of data you’re giving. I think one of the fears for lot of folks is like, what?

Jason: What are these like data hungry machines going to do with all this data? And particularly as a company, you don’t want to be giving out your client sensitive data. So that’s one of my challenges personally is like all of this sounds great. All of this sounds cool, except that I’m not going to give it my clients payment data and any kind of anything that’s sensitive at all.

Jason: Yep.

Shawn: So what’s, yeah, so I the good news there, and shout out to our friends at Maple AI, and so they are a terrific alternative to big AI, right? And so what they have built is a way to cryptographically assure that what moves from your device, be it your laptop or your phone, to let’s just say,

Shawn: The cloud where the AI does its work and then gives you a response back cannot be seen, captured, collected, used by any of the underlying hardware cloud providers, et cetera. So bottom line, end-to-end encrypted, great option. The open source, open weight models, which simply means they are not owned lock, stock, and barrel by Google, by Anthropic, by Meta, they’re getting better every day.

Shawn: And they’re becoming tuned in a way, know, everybody’s probably knows somebody in their neighborhood who’s gone and bought an Apple Mac Mini and put open claw on it and off they go. Most of those are going to be tapping into some backend cloud AI provider, but you can run them locally. And so in other words, you can have a private offline AI that runs on a piece of hardware in your office, in your home.

Shawn: And that’s becoming increasingly accessible. It’s not the easiest path these days, but it’s getting better.

Shawn: And it is a very, it’s a completely legitimate concern. You know, for example, and I forget the body that recently put this forward, but there is a piece of legislation either proposed or now passed that states that in the U.S., I think it’s the Bar Association, lawyers cannot submit.

Shawn: That have been generated by AI, forget the details, but the point is that legislation is already starting to perk its head up. So not just, I don’t want to risk my data, my client’s data, my personal data, but there will be regulatory regimes that say that you cannot actually use AI to produce this.

Jason: That seems like a healthy thing.

Jason: Yeah, we’re free market guys, right? So, yeah. So we’ll see. How that works out. But I think there’s, you got to pump the brakes at some point.

Jason: Yeah, for sure. Yeah. What other topics do think we should cover before we wrap this up?

Jason: Huh, well.

Shawn: Other end of this and I’ll try to fit my…

Shawn: Yeah, we’re just putting up this podcast, my goal is, I’ve been in this payments business for like 16 years and there’s so, we’re still onboarding merchants just to accept credit cards from paper checks, okay? It’s pretty common that we’re still onboarding merchants from keying in the card data into a physical terminal and they just don’t even know that there’s an online…

Shawn: Gateway that’s safe, that they can key in the card data. Yeah, they don’t trust it because there’s just so much lag time in catching up with technology. Like they don’t even know where it’s Stripe or any of these like tech products,? And I just think I have a lot of empathy for these folks because they are just trying to deliver a good product and service and put food on the table. And my concern for them is that the

Jason: The foundational layers of business are so rapidly changing right now that we need to get some of these tools and ideas and understanding into their hands. So, it may be an entrepreneur, it may be someone who’s been running their business for 30 years. It may be someone young, it may be someone old, but the goal is to get some of these tools into the hands of entrepreneurs and business owners. And…

Jason: And just have a good conversation and see if we can at least start the conversation. Absolutely.

Jason: Yeah, what I would humbly offer then is perhaps a repackaging of what I’ve already said, which is…

Shawn: Don’t be afraid to presume that some are. I choose the word consequential on purpose. I think it is the single most consequential technology of my lifetime. Consequential doesn’t mean best. It doesn’t mean benign. It doesn’t mean great or positive. It just means consequential. And so I think, and I say this in earnest, if the goal is to sort of ride out the last few years of your.

Shawn: Time running the business, then by all means, your family member or partner who is going to pick up the mantle and go, give it to them. But I think if you’re still in the game for a while, it’s unavoidable. So first is fluency and understanding, and that to me is just hands-on. And so we’ve got events here at Bitcoin Park. Tomorrow, in fact, is an open-claw meetup.

Shawn: And so there are opportunities like that to be in an environment where you’re not going to be worried or embarrassed that you’re going to delete something or break something. But just get your hands on it and come to understand that it is a force multiplier. And I think that’s what’s so incredible about it is with some fluency and some skill up-skilling with these tools, it is remarkable what you can do. And it is changing just about daily.

Shawn: Don’t be afraid. Become familiar. Get your hands on. And as a business owner, as an entrepreneur, as an operator, think about what you could do with 10 to 100.

Shawn: Think about now, and perhaps these are not yet your best and your brightest, right? But think about what you could do with 20 more sets of hands, right? And that, as I say, could be simple automation. It could be spinning up agents that run 24–7 to monitor. I built a newsjacker. It was a PR product.

Shawn: And it just watches for any news stories about a particular topic. So you can build things like that, right? If you want better press, if you want more press engagement, if you want better performance of your Facebook ads, let’s get real specific, right? There are tools now that will allow you to automate entire suites of so-called A-B testing for Facebook ads. That might cost you five to $10,000 a month from a marketing agency. Sad for the marketing agencies.

Shawn: But that’s now within the reach of someone who’s got a basic level of skill. Two things, don’t be worried. Have a healthy skepticism, certainly always, right? Don’t trust verify. Get your hands on it so you can verify. And then start to think about what would you do, as I say, if you spin up, not to commoditize human labor, but if you could spin up 10 to 20 virtually free employees to do a lot of the

Shawn: Lower value, high friction work, what would you do and how would that change your business?

Shawn: So three of my favorite ideas from this conversation are have an abundance mindset over scarcity mindset. You just touched on that again. Don’t live in fear. Have this skepticism, healthy skepticism, but don’t just hide and cover your ears and say AI is not happening.

Jason: The second one, what was the second one that I had? I know what it was. It was to delight your customers and automate the backend. So don’t replace your, maybe some companies will automate their phone service from humans to AI. That’ll be, yeah, yeah, yeah. That’s part of my frustration.

Jason: The innermost loop.

Shawn: We know how that goes.

Jason: Bucket list items in life is to get to a point where I never have to call a 1–800 number again. That’s like whatever assistant I need to hire, whether it’s a human or an agent or whatever, it’s like no more phone trees. That’s like on my list of, vision board, right? No more phone trees. But yeah, this idea of continuing to have that human touch in your business, but being pretty radical about seeing what you can automate behind the scenes.

Shawn: As if you don’t someone else will. And I hate to throw around, seemingly threatening phrases like that, but I do believe that’s true.

Shawn: The market forces are at play.

Shawn: And I’m not a young man, and I’ve figured this out. Let me just say that, right? So mean, this is not just for the 20s, 30 something young bucks. It’s accessible. I will say this. I’ll also sort of say that, or I will say rather, that I think AI as a set of tools, as a technology, as this force multiplier, is profoundly more powerful when you’ve got the knowledge behind it. You’ve got the…

Shawn: Operator skills, you’ve got the entrepreneurial skills, you’ve got the design skills, you’ve got taste, you’ve got connection with customers like that, then you wield this powerful tool in a way that, again, not to anyone’s exclusion, but an 18-year-old can probably fire through two long nights full of Red Bull and build something amazing, but they’re not going to have your insights into your business, your customers, your operations.

Shawn: So I would just put that in there as well to say that if you feel like you’re on the back end of this thing.

Shawn: You can wield it with the knowledge you’ve got more powerfully than someone who’s just new to that game.

From the Riverside transcript export, lightly cleaned. May contain errors.