2026 Trends: Trust in AI, Healthcare, College, AGI & more

Today in the Sky Lounge, we’re joined by Bryan Dennstedt to review how the AI predictions they made a year ago actually played out—and what’s coming next.

Nailing the Trough
Bryan and Todd predicted an AI trough of disillusionment, and they hit it dead on. Generative AI hit that wall hard this year. But here’s what’s interesting: there’s a clear divide forming. Some CFOs still dismiss it as a bubble that’ll never amount to anything. Meanwhile, when Todd demos AI capabilities in a room of ten people, one or two immediately download it and start using it. The gap between the haves and have-nots isn’t about access—it’s about willingness to engage.


Bryan frames it well with his “light bulbs to motors” analogy. For two years, companies installed AI light bulbs—helpful point solutions that let people work a bit longer, get a bit more done. But the bigger players have been building machines, rolling out factory assembly lines that leverage AI in ways that’ll start showing major wins this year. That’s what pulls everyone else out of the trough.


From Chat Bots to Agentic Workflows
The conversation shifts to what actually matters now: agentic workflows becoming the default. Not more chat bots. Background automations doing real work. Bryan sees companies like ClickUp embedding agentic frameworks directly into their products, while he builds custom agents just as fast on top of existing tools.
SaaS pricing models are going to compress hard as a result. Bryan’s already seeing shifts toward consumption-based models or drastic price cuts. When you can build custom solutions in hours rather than months, why pay multi-six-figures for off-the-shelf software that doesn’t quite fit?


Two-Hour Startups
Todd’s experience with Claude Code changed his entire investment thesis. He went from telling clients he shouldn’t code (too expensive) to shipping complete software solutions in two hours. Not vibe-coded guesses—actual production software built to CTO-level standards. His process: record a conversation, generate a business plan and technical roadmap simultaneously, validate there’s a market, then build only what’s needed for MVP.


This flips the startup funding model. Instead of betting on fresh Georgia Tech grads who’ll spend six months coding, find mid-career professionals with distribution networks and deep domain pain. Give them working software in days, not months. Success isn’t a billion-dollar valuation anymore—it’s a profitable business at $1-5 million.


Local Manufacturing and Trust Verification
Bryan’s wife runs Charlotte 3D Printing, serving everyone from antique car enthusiasts needing custom parts to kids printing school science projects. It’s the beginning of manufacturing’s future: produce local, consume local. Why ship plastic goods from China when you can print them down the street?
The other prediction Bryan’s excited about: trust verification becomes a major business category. When AI permeates everything—videos, conversations, content creation—how do you know what’s real? Reddit threads already ask “is this AI or not?” about every image. Bryan showed his team Will Smith eating spaghetti from a year ago versus now—you can’t tell if the current video is real. That verification layer is going to be worth a lot.


What Didn’t Hit
They missed on VC rebound and LLM memory improvements. Context windows got bigger but not the 10X they predicted. Patents becoming meaningless is still on the horizon, just not there yet. Commercial real estate is struggling as predicted, though “collapse” might be too strong—plenty of people are just concerned about their portfolios.


For 2026, watch agentic workflows, SaaS pricing pressure, local manufacturing, and the shift from technical to business founders. The technology moved faster than institutions could absorb. Now comes the catch-up phase.

Takeaways

  • AI is moving faster than institutions can adapt.
  • The rise of generative AI is reshaping business models.
  • Commercial real estate is facing significant challenges.
  • Venture capital is becoming more conservative and cautious.
  • Trust and safety frameworks for AI are still developing.
  • Niche podcasts are gaining traction and relevance.
  • The SaaS market is under pressure to adapt and innovate.
  • Local manufacturing is becoming more viable with 3D printing.
  • The future of entrepreneurship is shifting towards low-cost, rapid development.
  • AI will play a crucial role in verifying trust in digital interactions.

ABOUT OUR GUEST

Bryan Dennstedt is an accomplished Fractional CTO or Fractional CIO with TechCXO in Charlotte, North Carolina, where he has focused his efforts as a hands-on Fractional CTO and Interim CIO with numerous clients. He is an expert in mobile application development, healthcare integrations, and all aspects of telemedicine and has worked on over 40 engagements in a fractional capacity for the firm. His experience includes managing all information technology operations, from fractional CTO product development to Interim CIO large-scale technology migrations. Bryan works to ensure that his clients’ high-level Information Technology roadmaps are well-defined and then digs into the details to ensure that established metrics, accountability, and results are being delivered by the team he leads. Once a client is up and running with his methodologies, the Fractional CIO capacity can be leveraged in an ongoing model, and it can be ramped up to Part-Time CIO as needed throughout a project.

CONTACT:
LinkedIn: https://www.linkedin.com/in/phingers/
Website: https://bry.net/ai

The story this year in 26 isn't intelligence related. It's alignment. Technology last two years has moved faster than institutions, companies and our people. And we've got to catch up now.

BRYAN'S TALES FROM THE SKY LOUNGE

Todd Merrill:

Hi, welcome to Tales from the SkyLounge. It’s a podcast about business, consulting, and venture investing. We get out there in the world, we talk to people who are making it happen, and we get their stories. And this podcast episode is a special dual broadcast with AIwithBRI.com. Bryan Dennstedt.

Hey Bryan, welcome back. It’s been another year, and a kind of crazy year. How have you been? What’s been going on in your world?

 

Bryan Dennstedt:

Yeah, Todd, thanks for having me back. This is a blast to be back. I can’t believe it’s been a year and we haven’t done a podcast since then, really.

 

Todd Merrill:

I know. 

 

Bryan Dennstedt:

And gosh, so much has changed. So much is growing and going on. And I’m just excited to be back to unpack how 2025 went and look at 2026 with you. So…

 

Todd Merrill:

It’s crazy, isn’t it? Oh, it’s so much.

 

Bryan Dennstedt:

It really is.

 

Todd Merrill:

Oh man. Well, how do you want to start? You want to look at our last year’s predictions here and see how we did, and then maybe? 

 

Bryan Dennstedt:

Yeah, absolutely. I mean, I’ve got a burning topic to jump into, but let’s maybe look through the predictions first, pull out the magic envelope, and let’s see how we did last year.

 

Todd Merrill:

Okay. Yeah. And then we’ll get to your topic, right after we kind of see how we did.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

You know, of course, we used AI, you know, to score. So, first, the things we absolutely nailed. So, I don’t know if we nailed all this stuff or if it’s more subtle than that. Okay. So, we talked about…

 

Bryan Dennstedt:

… I’m going to take the win. Let’s take the win.

 

Todd Merrill:

W, yeah. AI trough of disillusionment. We said we’re going to hit an AI trough of disillusionment. Boy, did we ever, and then, you know, I think particularly generative AI is kind of what we’re talking about here. I’m starting to call it practically. I feel like both of us are kind of like through the trough and then well up the other side, and then there are these weird haves and have-nots that’s happening. I don’t know how you feel about that, or what you’re seeing in your clients’ lives. But you know, are some of them happy about generative AI? At least like there are people like, and you know, there are certain CFOs we didn’t know and love. They’re like, it’s a bubble. It’s horrible. It’s never going to amount to anything. And then there are people that, you know, you talk to them for a few minutes, and you do a demo of capabilities, and then the light bulb turns on. Usually, it’s like 1 out of 8 or 10 people in a room, when I’m given the demo downloads it immediately. Like, what do you mean? That’s like free or 25 bucks? 

 

Bryan Dennstedt:

Yeah, that’s right.

 

Todd Merrill:

Are you seeing the same kind of thing with that? Are we in the trough? Are we heading up the other side? Is this hopeless? 

 

Bryan Dennstedt:

Yeah, it definitely depends on where you’re sitting on, on your personal curve, I think. I do think the general society is still in the trough. We’re still heading into the trough, unfortunately, but you know, I’m well up the other side as well. And I heard the analogy the other day about light bulbs versus the motors, like, you know, we have to look at all these paradigm shifts that have happened, and we have been installing the AI light bulbs, the LLM light bulbs, the past two years, and seeing the value that it brings, and like, yeah, it’s great. It’s letting me work a little bit longer, get a little bit more done for every hour, and stuff. But the bigger companies that are really embracing this are building these automations, these big machines. And they’re rolling in the factory assembly lines that are leveraging LLM and practical AI and day-to-day stuff. And I think they’ve been secretly working on it for a year now, and you’re going to start to see some major wins as those come out, that’s going to really help us get out of that trough of disillusionment as a general mass. That’s what I think. We’re light bulbs to motors. 

 

Todd Merrill:

Yeah. The people who get it get it fast. The organizations haven’t gotten it yet, from my perspective, you know, to use your manufacturing analogy, I think people are seeing power tools and going, Ooh, I could use that drill, you know?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then, but it’s just a drill. It’s just like a point solution. It’s like marketing automation or proposal generation, or, you know, follow up on sales proposals, you know, harassing people to go follow up that kind of thing. I think there’s a huge upside once … I think we have to absorb this new change, and the rate of absorption is not as fast as I would hope, but I think we’re living on the edge of tech, you know, so maybe we’re just used to a faster pace.

 

Bryan Dennstedt:

Yeah, we’re a thousand percent used to the faster pace, but you know, it took years for the internet to catch on. It took years for people to get rid of their arithmetic departments and close down the manual ledger books, and switch to Excel. So, we can’t expect them to go fast on that, but calculating and risk-averse companies are going to get dragged kicking and screaming into this age.

 

Todd Merrill:

So, you know, I see a generational change here, right? So, like Copilot three years ago, everybody was forced, you know, force-fed Copilot, and then it’s like, I don’t know, I could kind of see it. Maybe it’s more annoying than useful. And then everything was kind of like ChatGPT. Everything was a chat bot for a minute, right? And then that paradigm was like, hey, you know, customer service agents will do chat bot, buy my Delta ticket, chat bot, you know. But I think now we’re starting to see agentic, like truly come out where you’re doing, you know, yes, it’s natural language, but it’s doing some really powerful things that are not necessarily language oriented, and then these agentic enterprise architectures are going to become important. I don’t think everybody realizes what that is, but I think for next year, maybe that’s something we’ve got to help people at the curve, that’s the way up the trough. Right?

 

Bryan Dennstedt:

Yeah, for sure. I’m putting together decks that are going in and presenting this concept to companies to say like, “You’ve got to stop development work for a month or two and build your agentic framework, and then you’ll be able to go 10 times as fast,” and they go 10 times, and I go, “Yes, if not a hundred times faster.”

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

So, people are looking at like, this is not twice as fast. This is 10 times as fast as you could previously go. Like the paradigm shift for software development life cycles has got to be completely rewritten. All the books have to be thrown out, and we have to go back in. And I almost say it’s Waterfall-ish. Like, the more solid your plans are, the better your agentic output will be. 

 

Todd Merrill:

I want to talk about that a little bit later.

 

Bryan Dennstedt:

Yeah, absolutely. Yeah. We’ll come back to hit us with some more predictions that I think we got a few more wins on the W side.

 

Todd Merrill:

Yeah, that’s cool. Yeah. Okay. Commercial real estate, right. The collapse of commercial real estate. And then, you know, we absolutely nailed that. I think you called it. You said we’re going to see collapses in major metro areas of commercial real estate. I don’t know if I’d call it a collapse yet, but I think a lot of people are pretty concerned about the portfolios at this point, you know, the people who have chosen to go back in the office are largely back in the office. And then there are a lot of people who kind of came out the other side converted to, you know, maybe we don’t need an office. So…

 

Bryan Dennstedt:

… yeah

 

Todd Merrill:

Do you feel like that’s going to change? I mean, I feel like that’s pretty settled science at this point.

 

Bryan Dennstedt:

I still, like, I still feel like we as humans need community. We need our tribe. We need to be able to break bread, and we don’t want to be trapped in these little screens that we’re in all the time. So, there’s going to be this new resurgence of how work is done, like caving, like, you know, like you and me hang out together in a Zoom chat, not talking to each other, but you know, like there has to be something of that. 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

So I think you’re going to see this shift, like in Charlotte, where I’m based, they just launched the Pearl Innovation District for healthcare. So, I’m seeing huge innovation starting to happen in the Charlotte area in the healthcare space, where different entrepreneurs and hospital systems are coming together. So, I think we’re going to have to create these spaces where serendipity can happen, where connections will happen, just like the office settings. So, I hope we see more and more of that, more coworking spaces, more living up top and working underneath, you know, kind of places. I think we’re going to get back to that. I was just watching a video on how everything in China that you need for life is within 15 15-minute walk, not drive, walk…

 

Todd Merrill:

Ha ha ha!

 

Bryan Dennstedt:

You know what I mean? 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

So, like, we have to get back to like the grocery store, the hospital, your workplace has to be accessible and easy to get to in some fashion. So, I think we’re going to redefine living over the next 50 years for sure.

 

Todd Merrill:

Yeah. But it’s kind of like, everything’s a big circle, right? You know, so you grew up in a small town, you could walk anywhere you wanted. You might drive 10, 15 minutes, but that’s okay. You know? And then I think everybody’s kind of, you know, able to do that again, because you used to have to come to the big city to go to a factory or you know, Coca-Cola or the big tech company in San Francisco, and then now we don’t have to do that anymore. You know, you talk about the ex or just not the suburbs, but like, you know, go live on a lake somewhere in the middle of North Carolina, you know, but you can do that now. Right? And then, so how cool is that?

 

Bryan Dennstedt:

Yeah. But I live in a busy part of town now, and on a school day afternoon, it’s only two miles to my daughter’s school to pick her up, but I could probably walk there faster than drive on certain days. 

 

Todd Merrill:

Wow!

 

Bryan Dennstedt:

So, anyway, yeah, we’ve got to fix some of these things, but I don’t see the resurgence, especially in commercial real estate, happening. I think their commercial real estate has to change.

 

Todd Merrill:

I do think your comment about coworking spaces being needed or some kind of event space or serendipity, you know, you can’t, serendipity happens a lot faster with density. And then how do we get to density? I don’t know. I don’t think it’s a bunch of, you know, like Reddit, subreddit forums. 

 

Bryan Dennstedt:

That’s right. 

 

Todd Merrill:

You know?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

I think at some point, you’ve got to go drink a beer with somebody or, you know, eat a salad for lunch or, you know, go do something.

 

Bryan Dennstedt:

I think that’s a much bigger topic for 2026, I want to come back to later ….

 

Todd Merrill:

… okay

 

Bryan Dennstedt:

After the next prediction is around trust. So, we’ll unpack that one in a big way.

 

Todd Merrill:

All right. All right. Next one, the win. VCs are more conservative and performing more in-depth due diligence. You know, there’s a lot of capital concentration. I think a lot of the money, you know, moved into this big name, you know, nobody got fired for betting on OpenAI yet.

 

Bryan Dennstedt:

That’s right. Yeah. 

 

Todd Merrill:

You know, and it’s getting harder and harder and harder for little companies or earlier stage growth companies to attract venture because the bar for venture investment, for what I’m seeing, you know, you’ve got to get like a million dollars ARR, you know, what? Two or three quarters, which is like crazy. Like, nobody could do that. Right? So, I think you’re seeing a lot of interesting alternate ways to start companies. It’s easier and harder to start a company than it ever has been. I don’t know how you feel about that, or you talked to a lot of very early-stage entrepreneurs in your life, too. What are you seeing?

 

Bryan Dennstedt:

Well, even what you and I do as fractional chief technology officers, like the due diligence that I have done this year on behalf of PE firms or whatever, has been accelerated. I’m able to use the AI tools to accelerate my ability to help assess this company on whether it’s viable from a code perspective, from a business model perspective. So, due diligence can go faster now, but be more thorough at the same time. But to your point, like, you know, there’s a lot of really crazy business models out there, but I also see AI being able to bring in such unique, brand new, simple businesses. Like, there’s such a niche for certain types of things. And there’s such an easy way to just bring in a simple business with very little money and grow it to be a hundred, 200 grand a year. So, I think you’re going to see… I certainly hope you see in the Kauffman Foundation and all these other places that entrepreneurship picks up. I mean, we’ve seen nothing but a decline in entrepreneurship for the past 40 years or so, and I certainly hope that AI ushers in, like I think I said last year, a new renaissance era and let that continue.

 

Todd Merrill:

I think that’s absolutely right. I think there’s going to be … I think, you know, with layoffs and stuff, I think there’s a lot of really talented people that need to start a business or have something rattling around in their head, where they can now go try it. And you know, some of these tools make it super easy to try, you know, get in business and figure it out really fast, whether it’s going to go or not, I think that’s super valuable.

 

Bryan Dennstedt:

That’s right. Yeah. You can fail even faster now.

 

Todd Merrill:

And remind me, I wrote a thing for due diligence last week.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

But it’s ridiculous. I’ll show it to you tomorrow. I don’t want to kind of open that one up yet, but I mean….

 

Bryan Dennstedt:

… very cool.

 

Todd Merrill:

It’s crazy what you can do with all that stuff.

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

AI agents are coming. So, we talked about OpenAI launching Operator as a research preview early in the year, and then the new Stack AI agents became mainstream with Operator, Claude agents, and Gemini agents all launching. We absolutely nailed that one.

 

Bryan Dennstedt:

They are 1000% here. I mean, Claude agents, I spin them up night and day, and there’s some working for me right now, I’m sure.

 

Todd Merrill:

Yeah. Oh yeah. For sure. I had to turn mine off, or else all the bandwidth would have gone away. 

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

But yeah, I mean, it’s nuts. It’s really a game-changer for that. A hundred percent agree about Claude, but we don’t want to close the door on anybody else. I think it’s going to be, you know, this big circle.

 

Bryan Dennstedt:

They all have an amazing agent capability. What I do think you’re going to see this year is more LLM Council-type things.

 

Todd Merrill:

What do you mean?

 

Bryan Dennstedt:

Where the older models are cheap enough that I can get answers from multiple models and simulate the best possible answer across multiple models.

 

Todd Merrill:

Like triage.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Okay

 

Bryan Dennstedt:

And so if you look, Karpathy released a codebase of LLM Council, and you can run it. It will hit GPT, Grok, Claude, and Gemini all with the same exact prompt. Pull back the answers, send them back to all four of them, and say, “Which one did the best job? Rank them.” And then it will simulate the best possible combined answer, along with which LLM nailed it the best. So, it’s a really, really powerful way to use agentic frameworks to help remove the bias and help, you know, soothe out. Or what happens when OpenAI has an issue and is down, that’s going to happen in ’26, sometime. One of them is going to have an outage, and if you use an LLM Council type model, you know, okay. One of my three peers is down, who cares?

 

Todd Merrill:

You know, we talked about, this is kind of maybe a hot take, but stacking agents as a concept, I think orchestrator, you know, and execution, agent architectures is a thing big fan, right. And I don’t know, I’ve written several things that do that. But then, you know, where’s it gets ridiculous? You know, you see these things on the internet where somebody spins up 30 Windows with like, you know, the whole coding like cycle and it’s like these three are checkers and these three do pull requests and these three check the checkers that are checking the pull request of the code.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then it just gets, it’s like, you know, it’s kind of crazy. At some point, I think the opposite of that is going to be true as well, where you’re going to have to have smart humans who know what the heck’s going on, you know, you can’t fully replace humans with it.

 

Bryan Dennstedt:

Yeah. But like you’re going to see in Linear and ClickUp and others, that you just assign the work to the agent seat, and the agent will do the task that you assigned it to based on that agent’s persona. So, I think you’re going to see the AI emulating the human societies that we’ve built. Right?

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

Like, we have high-trust certification to help validate that the hospital system is doing it the right way. So, that’s the checkers checking the checkers.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And so we’re going to have those simulated concepts there, and hopefully, it layers in the right checks and balances for us.

 

Todd Merrill:

Yeah. Yeah. It’s going to be an interesting trend to monitor, you know, where’s the line of…

 

Bryan Dennstedt:

… absolutely

 

Todd Merrill:

Yet another AI agent, on top of an agent, or, you know, when does human, the loop, you know, really require. 

 

Bryan Dennstedt:

That’s right. That’s right.

 

Todd Merrill:

We’ll put a pin in that one. We’ll see you next year, and we’ll talk about that one. Okay. Political, David Sachs, you called it, crypto and AI czar, which is interesting. You put them both together, but the techno czar for the new administration.

 

Bryan Dennstedt:

Yep

 

Todd Merrill:

He’s appointed as the point man for AI and cryptocurrency policy. And before diving into AI, shepherded an ambitious cryptocurrency bill, providing legal clarity for digital assets, which is what we’re talking about last year. We were hoping that that was going to happen. 

 

Bryan Dennstedt:

Yep

 

Todd Merrill:

What do you think? Good call? Bad call? Interesting?

 

Bryan Dennstedt:

Yeah. It’s this paradigm of like, you know, how are we going to make money as knowledge workers, as AI comes online more and more and more, right? Like, we all need, you know, we all can’t be Visa and MasterCard. So…

 

Todd Merrill:

… right

 

Bryan Dennstedt:

I don’t know. I mean, the cryptocurrencies are here to stay. The smart contracts are here to stay. They have to find their evolution into the actual day-to-day places. And, you know, I don’t see it going any … it’s not going away, but it has to get built into the day-to-day cycles of the economy. Like, you know, the Bitcoin ATM machines are just a fad kind of thing, but like, how do we lower the cost of transactions down so that more transactions can happen?

 

Todd Merrill:

I think that’s a big one. You know, the cost of a transaction. When it costs you 50 bucks to move a hundred or 150 bucks, like that’s a problem. And when it takes five minutes to move $50,000, and you’re not sure, like, did it go, you know, what’s going on?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

It’s nerve-racking. Right?

 

Bryan Dennstedt:

Yeah, you don’t need to do that. And you see these newer financial places coming online that you see the scams happening on with all the third-party financial people sitting on top of a banking infrastructure, but they’re helping to facilitate the money transfers instantly, right? The Venmo, the PayPal, the Wise. They’re removing the ambiguity of a wire transfer and ACH, but at the same time, have super high fees. So, I think something’s got to change there. 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And I think crypto is definitely the way to do it. That public ledger concept, people need to understand how that works and embrace it, and know that we can help reshape society to something better, I think.

 

Todd Merrill:

Yeah. And I think it’s all the same fintech problems you’ve always had L2, L3 somebody’s got to vouch for the transaction in the float.

 

Bryan Dennstedt:

That’s right. 

 

Todd Merrill:

Take a hit when things go sideways. So, okay. Yeah. So, we nailed that one. Crypto is still bullish. And then it feels like more clarity in the market is going to encourage more, you know, more businesses to stick their neck out and be more innovative. Okay. 

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

Very cool. And that was the next one. Crypto regulatory clarity under Trump. I think we just talked about that, but I definitely got more clarity on the rules. It’s still kind of weird being in the U.S., being in the crypto space, but it’s less so than it was before. So.

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

And then my favorite, the rise of the podcasts and you were talking about niche content, super niche content. How’d you still, I mean, we nailed that one. It’s still ongoing. How do you feel about that? Are you going to, I mean, you kind of, well, how do you feel?

 

Bryan Dennstedt:

I mean, I already have a few podcasts under my belt, but you inspired me to launch this one over the summer. So, AI with Bry, you know, check that one out. Like the niches are here. Like, the strong players that are talking about a certain niche, they just need a few hundred good listeners to help curate the job and the inspiration that you need. I don’t have to go out and help millions and millions of people like OpenAI is doing or billions. Right? Like, I just hope I help a hundred CEOs learn how to embrace AI, figure out their AI strategy, dive in. And so, I’m still very, very strong on podcasts and jumping off the cliff. And I just watched a video earlier today, something about, you know, go out and do more things that embarrass you.

 

Todd Merrill:

Ha ha ha!

 

Bryan Dennstedt:

Right? Like, get out there, get over this fear of being embarrassed.

 

Todd Merrill:

Yeah. Yeah.

 

Bryan Dennstedt:

Right? And a podcast is a great way to do that. Like, we’re going to flub one or two things here on this podcast, but I don’t even know if people are going to notice it, right?

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

You and I might notice it, but you know, for the most part, like get out there and do something, chase the life that you want, and I think a podcast is a great way to help put a stake in the ground and stabilize around something that you’re passionate about. 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And we’re all passionate about something.

 

Todd Merrill:

Yeah. Oh yeah. Good points. You know, I was just thinking through, you know, if you’re super niche, you’ve got the right couple hundred people watching you religiously. What’s that worth? Right? 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then how do you determine value? You know, top of funnel brand is a thing you have to do. Super important.

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

How do you measure that? And then I had a piece of hardware that I’ve been pushing. Like, I’ve, you know, it’s a little recording device. I won’t name the name. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

But, you know, so I was going to give it to one of my clients, CEOs, who’s a portco of probably one of the largest two or three private equity companies on the planet in Boston. And it’s like, what is that worth for me to make that introduction and say, “Oh, you have to get this.”

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

You know, that’s worth a lot, but you know, it’s not going to … they were yelling at me cause, “Hey, you’re not,” you know, I had a referral agreement, and they’re like, “Hey, you’re not promoting us because you didn’t like post 15% off black Friday.” Like, guys, you know, you don’t get it, what I just did for you is way more effective.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

It’s probably going to end up with a lot more business for you in a lot more important rooms than, you know, some Instagram model, you know, saying, “Hey, this is a cool thing. You’ve got to get it or tick tocker.”

 

Bryan Dennstedt:

Yeah. I think it’s that concept. You have to follow your passion on that one and support the products that you really love. And naturally I hope that the brand deals fall out of it, and things like that, but you know, it’s also making sure you’ve got your Patreon and you’re Buy Me A Cup of Coffee links set up or whatever that is too, cause, you know, I still believe 80% of the planet is good and decent people and wants the best for us.

 

Todd Merrill:

Yeah, yeah.

 

Bryan Dennstedt:

So, you know, I think it’s that concept of, you know, you just don’t know. I think a podcast is a great way to plant seeds of serendipity to stand by your convictions and drive stuff forward. So, but yeah, very bullish, like the age of personalized content is upon us with AI. And so, you know, a podcast is a stepping stone towards even more personalized content.

 

Todd Merrill:

I wish I had that screenshot. It happened to me this morning when I was watching your LinkedIn, but just below it, there was a LinkedIn ad. It was like a little cartoon with a bubble. I don’t know. Maybe you saw this one, but I don’t remember what it was for, which my dad will laugh, but it said, Hey, TechCXO, blah, blah, blah, blah, blah. Get you some blah, blah, blah. And then I was like, wait, you know, scroll, scroll. And then it was an ad. It was promoted. It was definitely an ad that was inserted for me with that label. You know, like I work for that company. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

I was like, oh, that is pretty slick. But I mean that’s where we’re headed…

 

Bryan Dennstedt:

Some of the best newsletter programs out there are already doing that, you know? Whether it’s 6 a.m. city or whatever the local one in your city, but they’re keeping track, like Medium. I think Medium does this the best. Any links I click on in my Medium newsletter, the next newsletter is going to have more links like that. You know, like I clicked on this Python thing here or this, you know, workout thing there, I get more articles geared towards me and my Medium feed because it knows which articles I clicked, which ones I read. So this hyper-personalization that AI and tracking are going to bring super, super amazing, because we’re going to go down the rabbit hole even further, but scary at the same time.

 

Todd Merrill:

Yeah. I mean, it’s kind of cool. Sid Mookerji, he has Silicon Road ventures. So, he was writing about this, his big e-commerce, you know, evolution of e-commerce. He was saying, he thinks that there’s going to be a time pretty soon that e and his portcos are building where every website you go to, every e-commerce experience is going to be only … it’s completely unique to you as a buyer. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

I can’t wait. You know, I don’t know what that token utilization cost is going to be for something like that, but it’s going to be glorious. 

 

Bryan Dennstedt:

That’s right. Yeah.

 

Todd Merrill:

Anyway. All right. So, we did pretty good on that one. Let’s go to the yellow lights. Okay. So, partially correct. All right.

 

Bryan Dennstedt:

I like to say we got more wins than yellows and reds. Yeah, hit us with the yellows. 

 

Todd Merrill:

Yeah, yellows, and these are half, right? Okay. So, rising tide lifts all boats, and then we’re going to see a VC rebound. Didn’t really see a VC rebound like we had hoped. I don’t know if that’s interest rate-driven or everybody’s kind of risk off right now, going for the big companies, the big names.

 

Bryan Dennstedt:

I think we did this last year in the age of the beginning of the new Trump presidency, too. Like, that’s a wild card for sure, combined with AI, is changing everything.

 

Todd Merrill:

Oh, yeah.

 

Bryan Dennstedt:

Do I save the cash and deploy it later? Do I put more micro bets out there? You know, I don’t know. I think we saw a lot of people just investing in second rounds instead of more firsts.

 

Todd Merrill:

SPV for anthropic.

 

Todd Merrill:

Exactly. Exactly.

 

Todd Merrill:

Yeah. It’s a scary time to be an investor because, you know, I was helping one client, I want to be a little bit vague about who they are, but with a certain topic and then it was going to be a builder by, and then we didn’t think build, we’re going to go help them research, as well as AI adoption things where they said, Hey, you know, if we could do blah, blah, blah, that’d be really cool, but we don’t know how to do it. Okay. We’ll go shopping. Go look for a couple of solutions for them. Found a couple, three, four, five solutions, two or three actually answered the phone. SaaS companies that were early stage, you know that.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Probably Series A-ish kind of range, kind of sort of had early, you know, couple-year-old AI ML visual model kind of stuff. And then, nothing was quite right. And, you know, a couple of us looked at each other and said, you know, we could probably write this pretty quick with one of these frontier models, did it, and they got 8% of solution that was appropriate for this client and said, Hey, what, you know, for a quarter of the cost of one year of these other folks, which is multi six figures, would you like this custom software that does exactly what you want? And then, so if you think about it? They said, yeah. And then on a Tuesday morning, we’re able to recreate most of it. And then, you know, so all these SAS companies are like, it’s how do you compete with that? Right? Their whole business model is challenged now, where just because you have software doesn’t mean anything. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

It’s, you know, I think a lot of investors are looking at that going, holy crap, what do we invest in? I don’t know.

 

Bryan Dennstedt:

Yeah. So, yeah, it’s super, super interesting. I wish I had the inner mindset, but I think it’s, yeah, I don’t know how to add more to what you just said. It’s really, it’s spot on. Like, everybody’s doing their unique thing. They’re trying to figure out the AI stuff as much as they can, too.

 

Todd Merrill:

I think where this is going is a combination of what you’re calling niches, you know, like lots of tiny little companies that are low six figures ever, right, and nice little business for a couple of people. And then, what’s wrong with that? You know, and they might need a little capital, a little bit of help on the services side to get going. And maybe that’s the way we start companies now. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Maybe it’s not, you don’t need half a million dollars to go in six months for a year to go build software, right? Before you even know.

 

Bryan Dennstedt:

You definitely don’t, you definitely don’t.

 

Todd Merrill:

Yeah. You can be up and running in a couple of weeks, and then, you know, the distribution and it’s….

 

Bryan Dennstedt:

But it comes back to the plans.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

Like, if you don’t have a really well-thought-out business model and you don’t … like, I’ve been working with a founder who’s got a very detailed business plan, and she started vibe coding it. And she’s realizing, oh, I didn’t have this built. I didn’t have this built. I thought I had everything, all the I’s dotted and T’s crossed, and I don’t. But at the same time, trying to land a waitlist and everything else. So much to do as a business owner. So, the strategic planning. That’s where the money should be going right now. Not into the development side. 

 

Todd Merrill:

Amen. All right, next one. That was kind of sort of yellow, VC portfolio reorg and/or capitulation. I don’t think we’ve seen capitulation this year. Yeah. Everything’s kind of static, and everybody’s kind of holding their breath still for my seat.

 

Bryan Dennstedt:

Yeah, I would agree. I think everybody is buckled down and waiting to see how some of these chips fall. And I think that we’re all going through this learning curve of AI as well. You know, like we’ve all got to learn it, see how we want to use it, embrace it. So, I have to just go back and look at other paradigm shifts that happened, you know, the internet coming out. I mean, there’s clearly going to be some major winners and some major losers, but we’re trying to avoid some of those things by being a little conservative right now.

 

Todd Merrill:

Yeah, for sure. Trust and Safety Frameworks for AI, specifically, well, early, right? I think you got out in front and then got a little backlash from the business community for being a little bit too strict. And then I guess the U.S., the Federal Government got out in front and said, “Hey, no state regulations allowed.” So, it seems like everybody thought about it for a minute and understands this as it’s important, but we didn’t get anything with super teeth yet. You know, there’s no AI insurance yet, that I know of, that you can get, kind of like cyber. What are you seeing on that? Do you think anything is going to move this year?

 

Bryan Dennstedt:

I think somebody has to be bold enough to put out the official AI policy, and hope they’ve got the right numbers on it. But I guess I’m seeing people doubling down on their cyber insurance and having the AI pieces included or excluded from their cyber side of things. You know, it’s really the errors and omissions insurance. 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And it’s a better understanding around … you know, Kevin Carlson and I talk about this all the time around, you know, and as an artist, what writes a lot of this stuff is copyrighted, and then the code that it generates is generating it from open source codes and so it’s just a weird blending of laws and stuff that we’ve got to sort through and figure out. You know, there’s the big lawsuit over the books and the authors that happened a few months back, you know, played out. And I think we’re going to see more of that in ‘26. 

 

Todd Merrill:

Who owns stuff? I think that’s a big deal, right? 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then I think there’s probably something in the healthcare space where you see people you know, chatting with their AI, whatever that means about relationships or, you know.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Like, you know, who’s liable when the AI is like, oh yeah, you know, go start your whatever business that’s completely insane. Yeah, good call. Go for it. You know, and then you lose your shirt. Yeah, it’s going to be, or, you know, therapist, you know, family therapist, or I don’t know.

 

Bryan Dennstedt:

Well, I’ve enjoyed putting these predictions last year together as our first time. So, speed through quickly the negative ones for us, Todd, so we can get to our 2026.

 

Todd Merrill:

We only had two. 

 

Bryan Dennstedt:

We don’t need to…

 

Todd Merrill:

… and that was it. 

 

Bryan Dennstedt:

Okay

 

Todd Merrill:

So, patents are becoming meaningless. You know, we kind of miss that one. You know, I don’t know. I still agree with that one. I’m going to still stand on that one. I still wouldn’t do another patent if I did another startup, unless I was in some kind of healthcare pharma, you know, biopharma, and then maybe some kind of fundamental, you know, patent on AI. Like, if you’re going off and …

 

Bryan Dennstedt:

… it goes back to what you just said, ownership, who’s going to own stuff, and why do I put these secrets out there knowing the AI can reverse engineer it? So, yeah, I mean, you’re going to want to play offense and defense and do it, but I agree with that prediction still, just maybe might be a year or two away.

 

Todd Merrill:

All right. The last one, LLM memory improvements. You called 10X improvement. We didn’t quite get the 10X, but we did get bigger. 

 

Bryan Dennstedt:

Yes

 

Todd Merrill:

I think it’s challenging, right? With the current architectures. I don’t know. I think there’s got to be a … I think we’re going to get bigger contexts. It’s going to pay to play, and it’s going to be expensive. Yeah, I think it’s a limit. I think something’s got to change, and we’re going to have some kind of fundamental?

 

Bryan Dennstedt:

Yeah, we think that the MCP was going to be our savior, but we didn’t realize, when we connected 27 MCPs that choose up the context window before you even start typing.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

So, you know, I think we’re level setting the MCP aspects of it. And I do think RAG storage is still a strong option, but yeah, I think that we have seen a significant increase in the power of, you know, GPT-5 and the newer Opus, and things like that. And so it’s hard to know how many tokens we really need, but I think it’s that the key difference between humans and the LLM still is that you and I can think on the fly and recalculate on the fly way quicker than an LLM. LLM is always going to take 15, 20 seconds to do its thinking, and then it has to reset the context. And so until the context windows get large enough and it can recalculate its prompt on the fly as it’s listening to new input, like you and I can do as a human, it’s got a ways to go, and I’m not worried about them taking over.

 

Todd Merrill:

Yeah. I’m with you in that, you know, that efficient compute, you see in that chart with the efficient compute horizon where you go out, and you throw more processors at it, and it only gets a little better, a little better, a little better, but it never gets beyond this one logarithmic boundary. Yeah. I think we’re there. I think we’re seeing, you know, hey, we know it can do focus things pretty well. Can’t do everything. It’s like the old thing I used to tell people when I drop into a chaotic turnaround, you know, we could do anything, but we can’t do everything. Right. And that’s kind of where we are. It’s an efficient, you know, little co-processor, and you do a lot of really good damage. That’s it. I think we did pretty good last year. What are you looking at for 2026, or what’s on your mind for next year?

 

Bryan Dennstedt:

I don’t have a whole bunch, but I want to throw out five or six, and then we can bat those around a little bit, and I’m sure you’ve got a pretty strong list, too.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

So, on the AI front, I mean, I think the agentic workflows, some of the stuff we’ve talked about are going to become the default inside of companies, like whether they realize it or not, either through a tooling or whatnot, but I think that’s going to be, you know, we’re going to see fewer chat bots and more background automations and agentic workflows happening. 

 

Todd Merrill:

All right. Are people going to build them? Are they going to buy them?

 

Bryan Dennstedt:

I think it’s going to be both. I think you’re going to be met with, you know, ClickUp rolled out an amazing agentic framework. These companies are trying to embed them in, and then there are people like me who are on this bleeding edge, and we’re building them just as fast as ClickUp is. So, it’s going to be that both avenues are going to be successful. 

 

Todd Merrill:

Your agent goes here on top of somebody else’s framework?

 

Bryan Dennstedt:

That’s right. 

 

Todd Merrill:

I think that’s the way to go. I think people are going to buy them initially. And then once they figure out, oh, we’re paying a lot of money for these, and there’s going to be this new function, kind of like old school Fortune 500 IT applications development, internal IT apps, that’s going to come back around for companies of all sizes, where you have one or two people that are going to nerd out and make those kinds of agents for you. I think that’s the way to go. What’s your second one? You had another one?

 

Bryan Dennstedt:

On the business side, like you know, I’m already seeing some companies start shifting, but the SaaS pricing models got to compress hard. Like, I think you’re going to see some royal shifts in either consumption usage or drastic cuts to SaaS pricing, as you know, agentic rolls out. So, I’m very concerned about the SaaS market.

 

Todd Merrill:

Well, you know, this is a hard one because, yeah. SaaS is dead, long live SaaS, right?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

You’ve got to have a place to put everything. That’s not going to go away. Right? And then as a scoreboard or a common denominator repository, that’s useful. And then there’s business logic, right? On top of, but you know, if you have to implement Salesforce or NetSuite or something, and then you have to pay a bunch of people, a bunch of money to customize it, like, let’s just build it, you know, for exactly our company, and then we don’t have to shoehorn anything. I think that’s going to happen.

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

Yeah. I can’t tell you how many times I go into companies and then we look at their marketing motion or, you know, cause that seems to be a fertile ground for practically AI, and then, you know, you kind of go maybe we don’t need a CRM, you know, like a formal CRM, but you need a lot of agents to do the same kinds of things, but they can be highly customized. So, the way you get to SaaS is going to change, and is it going to be the God box up in the cloud? I don’t think that’s true anymore. I think it’s got to be way more flexible than that.

 

Bryan Dennstedt:

That’s right. And I think it’s going to shift down to our phones. I don’t know if it will happen in ‘26, but that’s the next wave that’s going to come for sure.

 

Todd Merrill:

Oh, what do you mean by that?

 

Bryan Dennstedt:

I think that we’ve got this GPU model of LLMing right now, that’s got to shift and change, I think. Some of the research that I’ve been seeing and reading is that there are new frameworks that are coming out that are going to push a GPT 5.2 type model to be able to be run on a phone-contained.

 

Todd Merrill:

Okay

 

Bryan Dennstedt:

Like, you can’t do that right now. I can’t say that’s a ‘26 prediction, but I think that’s where we’re heading as a trajectory is that I need to move these models into my smart glasses. I need to move them inside the robot. I need to move them inside my smartphone. And so we’ve got to be able to run a very powerful model on a small CPU, and there are going to be ways to accomplish that.

 

Todd Merrill:

Yeah. I mean, well, you know, in 2019, I can remember writing stuff for the Google glasses. We did Chicken eight or vision for Chick-fil-A, you know, where he identified that’s French fries, that’s, you know, milkshake or whatever. But that was TensorFlow, right? And then you had very specific, you know, it was pretty hard, but you could do it. And then you load it right onto the glasses and then it could run. So that was back then, you know, so I know we can do more better now. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

I think that’s a natural evolution ambient compute. It’s going to be a thing that tags right along with that. I think there’s going to be, like, we were, I’m starting to record everything. Well, I guess we’re recording this.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

But I don’t have my normal recording device. When anybody says, “Hey, I got an idea.” I go, “okay,” you know, “let me record this,” you know?

 

Bryan Dennstedt:

That’s right. 

 

Todd Merrill:

But I mean, we’re going to start recording everything all the time for purposes of transcription.

 

Bryan Dennstedt:

Meta just bought Limitless, right? That Limitless was the pendant you wore, and it records everything, every moment. And so we’re moving… what’s that Robin Williams movie, like, I don’t know. Whether it’s altered carbon or that one photographer, Robin Williams movie, where your whole life is recorded onto the chip, you know, so let’s play the highlight reel.

 

Todd Merrill:

Truman Show

 

Bryan Dennstedt:

Yeah. Truman Show. Exactly. 

 

Todd Merrill:

No

 

Bryan Dennstedt:

So…

 

Todd Merrill:

Huh? Yeah, I don’t know. Yeah. That’s going to be interesting.

 

Bryan Dennstedt:

I got two more, one on people and one on society.

 

Todd Merrill:

Sure

 

Bryan Dennstedt:

And then I’ll let you hit us with yours. 

 

Todd Merrill:

Yeah, yeah.

 

Bryan Dennstedt:

I think, you know, you and I are lucky that we’ve grown up in this programming world, and that’s going to shift. I think programming as a career path has to shift big time. But I think the key thing is that those who are directing AI are going to outperform those who are just using it. And I think there’s a subtle, but very distinct difference between knowing that certain things are biased and this is how I get what I want, versus I don’t know, I’m stuck. Here’s my problem. Help me, you know, that kind of thing. So, I think you’re going to see these builders versus coordinators, these directors of AI versus users of AI. And that’s going to create this again, a dichotomy, but the most exciting one, I mentioned it earlier that I think we have got to figure out. And it goes back to everything that’s raising up with AI is, ownership and all those things is, is trust verification.

 

Todd Merrill:

Okay. 

 

Bryan Dennstedt:

I think, you know, I’m using AI to create videos. You know, we’re using AI to help us with this podcast, all these things. Like, AI is going to permeate every aspect of society. And how do I know that’s really Todd sitting there? You know what I mean? So, like, there’s going to be this whole new business empire that’s created out of trust verification. Was this real? Was this a human? That is a core product category. That’s going to bloom in 2026. 

 

Todd Merrill:

Gosh, half of Reddit is like, hey, is this AI or not?

 

Bryan Dennstedt:

Yeah, yeah, yeah.

 

Todd Merrill:

And then I was like, oh, I don’t know. Look at that toe. And you know, fish looks weird.

 

Bryan Dennstedt:

Yeah. I just showed my team earlier, you know, Will Smith eating spaghetti one year ago versus Will Smith eating, that’s the meme going around. You can’t tell if that’s the real Will Smith eating spaghetti or not at this point with video-generated AI.

 

Todd Merrill:

Wow!

 

Bryan Dennstedt:

It is that good.

 

Todd Merrill:

Well, at some point, does it matter? And you know, if we’re going to blur who owns what and what’s real, like what a confusing universe, but maybe it’s okay. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Like, Hey, that’s right. Will Smith is eating spaghetti. 

 

Bryan Dennstedt:

Well, or like Elon’s theory is we’re in the matrix anyway.

 

Todd Merrill:

So, I don’t know, gosh, I’m going to have to, that’d be a New Year’s Eve topic for the evening.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Geez. All right. 

 

Bryan Dennstedt:

Hit us with yours. Those are my couple of quick predictions.

 

Todd Merrill:

All right. So, I want to shout out manufacturing.

 

Bryan Dennstedt:

Oh yes.

 

Todd Merrill:

This is your little Russian stacking dolls thing that you sent, and I got the puzzle piece out. So, I got to post that, but like your wife… so it’s funny that came about the same time. I don’t know if you knew this. My dad’s a plastics engineer originally. So, you know, he’s one of the first guys to go to college for that as a chemical engineer, worked for Rubbermaid for the first part of his career. So, I told him about that, and he got all excited.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then, went to our favorite Claude, you know, business analytics prompts that I have lying around, and then, you know, we’re like, hey, let’s do a business model for on-demand 3D printing. You know, kind of, your wife has a company doing that. I think that’s the future. I think that’s exciting.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

You know, how do we get manufacturing? You know, China is great. China has done really good at cheap stuff, but it always bugged me that it’s like, why do we have to make it there, put it on a boat, spend all this gas to get over here so we could buy it for cheap? Like, it didn’t make any sense. 

 

Bryan Dennstedt:

That’s right. That’s right. 

 

Todd Merrill:

So, maybe this is the thing that kind of lets us, helps us to produce local, consume local, you know, be able to buy our sheets local. Like, my hometown is a big textile town historically. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

It’s hard to go buy sheets, you know, get to go buy them on Amazon. I don’t know what they feel like. You know, maybe they’re itchy. Maybe they’re not, you know? I don’t want to live in that world.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

I want to be able to figure out how to go buy stuff locally from the place down the street.

 

Bryan Dennstedt:

Well, it’s the beginning of the future of manufacturing, like my favorite science fiction thing is Von Neumann probes, where they’re self-replicating probes that we send it out. So, they’ve got the 3D printers and everything built in them that they can self-replicate when they gather enough raw material. Right? But this is the beginning of it, right? Like, anything that’s plastic-oriented right now. You know, my wife saw this coming in and built this little business, Charlotte 3D Printing. So, it’s charlotte3dprinting.com and, you know, threw up the website, threw up a couple of quick blog posts, and boom, it comes up first for Charlotte 3D Printing as a keyword.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And we’re getting leads, and it’s a whole bunch of unique manufacturing things, people with antique cars that can’t find parts.

 

Todd Merrill:

That’s exactly what we’re going to do with my dad. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

His an antique car guy.

 

Bryan Dennstedt:

Right. Yeah, exactly. And Dungeons and Dragons models that are unique.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And I crafted this cool little dragon, and I want it printed myself. She had somebody print a school science project. I built this in AutoCAD, and I just want to print it for my teacher, you know? So, all these unique on-demand and again, unleashing this creativity of society that’s there in such a big way. So, I think local … everything has to shift to local. We’ve got to grow our food locally. We’ve got to manufacture locally. Like, everybody needs to have a little 3D printing hub and whatnot. So, I think that you’re going to see that continue to boom. 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

And that’s something that AI can’t do right now, right?

 

Todd Merrill:

Yeah. Well…

 

Bryan Dennstedt:

AI can’t print things. But AI helps for sure. Yeah. 

 

Todd Merrill:

Right. Yeah. You need that creativity. And then, like The Fourth Turning book, I don’t know if you’re familiar with that, but like the art, like my kids are a little older than your kids, but that generation that’s just now coming of age.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And in high school, they’re supposed to be the artists, you know, the whole grand scheme of things. So, I think we’re going to see a lot of creativity.

 

Bryan Dennstedt:

My kids are younger, and I see them all the time. One of them in particular likes to just hang out with the Echo device and have conversations, and I have a very young child right now. And I was holding her just last night, I think, thinking about that same exact thing, is like, she’s going to grow up in the age of AI Angels or Jiminy Crickets or whatever you have on your shoulder, that’s guiding you through life. Like, is this really what you want? You know, are you going to take that drink? Are you going to smoke that cigarette? Like, you know, the agent is going to be there guiding you and helping you and/or reporting back to the parents.

 

Todd Merrill:

Everything’s recorded. Your dad and mom are watching.

 

Bryan Dennstedt:

Yeah. Yeah.

 

Todd Merrill:

Synopsis will be provided. 

 

Bryan Dennstedt:

But manufacturing is going to blow up. Like, you’re going to see, again, personalized manufacturing.

 

Todd Merrill:

Yeah. And coming back to the onshore, I think it’s a big, big part of that as well. Local, buy local, grow local.

 

Bryan Dennstedt:

Yeah 

 

Todd Merrill:

One thing I want to get out there that changed my life this year. So, I went really deep on the anthropic ecosystem, trying to help the sales and marketing non-technical parts of the C-suite. Wound up with MCP, and that was a game-changer. And then I kept going, and I found Claude Code. 

 

Bryan Dennstedt:

Oh, my gosh.

 

Todd Merrill:

You know, and I’m a coder. I’ve always been a coder. I haven’t coded in a while. And you know, a year ago, I would tell clients I can code. You should not pay me to code. That’s too expensive. And then, so right around Father’s Day, I started saying yes to these little projects cause a lot of people say, “Hey, I’ve got this idea.” And then, you know, I just wanted to see what it would do. And then haven’t found the bottom of it yet, which surprised me. I didn’t think that’s where I was going to go. I thought I was going to just be able to tell people, well, it’s okay, but you know, this is going to vibe code you crap. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

So, a lot of complex thoughts here. So, I’m basically shipping. I’ve got this process where I’ll record people, and it goes back to your planning, right? I think planning is super critical. So, I’ll record people in conversations, take the transcript, and put it into my planning models. So, I’ve got a couple of really nice prompts that I’ve added to, you know, refine those where I’m going to generate a business plan with a technical plan at the same time. So, you’ve got a product mark, you know, that product management roadmap generated simultaneously with the business needs. So, you’re going to build the things. The only things that you need for MVP. And then I have a couple of things in there, like, I don’t know if there’s competition, and when the pricing is, is there a business here? Are you wasting your time? And then, what’s the minimum, minimum? We got a code to get it in the market. And then my thesis was okay, we can launch a lot of companies here. If I can remove that milestone of you need software to sell in 10 days or less, 10 hours or less, sometimes it’s two hours to get the stuff launched with a domain name in AWS, and it’s not vibe coded. Right? You can’t just say, “Hey, I want a thing.” Right? And then let it guess. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

That’s not what we’re talking about. I think it’s I have very strong preferences as a CTO with decades of experience on how I want stuff built. I’ve got all that stuff kind of engineered in. I can hit a button, and then it goes fast in that lane. Right? But think what that does to businesses, right? So, it gets you, like, if I could say, hey, before new year’s, which is what two days, I can have you in business and you can be selling, but you got to prove to me, you can sell this stuff and then next quarter we’ll do phase two and then maybe phase three, and then what does that do for the world? So, I think, you know, just kind of extrapolating that out, how we start businesses changes, what we invest in changes, a lot of ideas that were marginal now become doable, and with not very much effort. It’s a fast-food era of software.

 

Bryan Dennstedt:

You need to have me back. We need to untie/unpack that topic for an entire hour. I mean, you’re spot on.

 

Todd Merrill:

All right. Yeah.

 

Bryan Dennstedt:

I mean, that is exactly right because I’ve been fortunate to be an advisor and a judge at some of these weekend hackathons, and the stuff I saw two or three years ago versus what I see this past year coming out is just mind-blowing what they can accomplish in 48 hours, you know, full website built out, pricing models done, sign up, you know, onboarding. 

 

Todd Merrill:

Well, that’s two hours. Yeah.

 

Bryan Dennstedt:

But think from me and you meeting as strangers to creating the brainstorming session to whiteboarding it, to bringing it to life in 48 hours, like they’re walking away with a viable business that has already generated money. Right? You know what I mean? Like, I already reached out to my LinkedIn network and generated five grand in sales in 48 hours of a hackathon. 

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

Like, yeah. And you and I know we can do that all in two hours. Once we have the framework set up. Like, I proved it with my daughter just the other day. We built an app and launched it together in less than 45 minutes.

 

Todd Merrill:

And then, so now, so like what happens, right? So how do we make money? How do we impact the world positively? Right?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then, I want to start a bunch of companies, right? Or I want to help a lot of people start a lot of companies, and it’s no longer about the investing model used to be go put 50 grand on a couple of juniors at Georgia Tech. They’re really smart, and they’re going to code something really amazing. Yeah. That’s stupid. 

 

Bryan Dennstedt:

Right

 

Todd Merrill:

Now, it’s about like, go find somebody that’s mid-career that’s got this burning desire itch to go, you know, solve a problem. Just needs a little bit of software, knows a lot of people or, you know, a fair amount of people, and is not the technical founder, it’s more about distribution, sales and marketing. Right?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then, you know, you’re just a decent, you know, we’re back to business founders.

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

And then boy, that’s like completely upside down from where we have been. Right? Where’s your MBA? 

 

Bryan Dennstedt:

That’s right. 

 

Todd Merrill:

Well, and then I don’t want a fresh out MBA, right?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

I want somebody who’s kind of got a lot of friends. They’re going to buy this thing because they’ve been living the pain and, oh my God, yeah, I’m so glad somebody fixed that for me, and then we don’t have to have, you know, a billion-dollar valuation.

 

Bryan Dennstedt:

That’s right.

 

Todd Merrill:

You know, we can be successful at 5 million or 2 million or 1 million. Anyway, I don’t know. So, for me, that’s like the big game-changer. And then that works at scale. And so we’re using that same process. And PE companies that are decades old that have a mess, right? And we’re going to PE companies and saying, hey, you know, some of these problems that were intractable, where you have all these old ancient technologies that nobody remembers how to operate, and everybody’s scared to breathe on it. We now have the ability to grind through a bunch of stuff in a hurry, make a plan, you execute the plan, and then turn this thing around, whereas before it might’ve been untenable to bring it forward.

 

Bryan Dennstedt:

Yeah, absolutely. Well, all right, let’s pivot into a lightning round. Then I’ve got two or three. I know you’ve got a few, so you know, throw one out and I’ll react to it for two seconds, and you can, and then we’ll switch.

 

Todd Merrill:

Your turn. Go ahead. What do you got?

 

Bryan Dennstedt:

Is college still worth it?

 

Todd Merrill:

Oh, geez. I don’t think so. I don’t think so. I’ve got one kid who’s 21 in college, and I’ve got one who’s 23. I told him to go to tech school to be a mechanic. Or, you know, we’re still figuring that one out, but one wants to be an artist. One wants to be a mechanic. He’s not learning what he needs to learn in college.

 

Bryan Dennstedt:

I like what you just said before I asked you the question. It has to be paired with execution. College is probably still worth it if it’s paired with execution.

 

Todd Merrill:

Certain things, you need college. You know?

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Is it worth it for an English degree for $120,000? 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

Not a chance. World models. We talked about AR/VR last year. You see all these folks coming out of meta and all the big thinkers, abandoning LLM is not the cool thing anymore. What do you think?

 

Bryan Dennstedt:

Yeah.

 

Todd Merrill:

World model is going to be the way we get to AGI. Is it going to be incremental? What’s it going to open up? Or is that going to be like a nothing burger?

 

Bryan Dennstedt:

Gosh, you stole my next question, AGI by 2027. So, let’s answer that together, I guess. I mean, I ran into capitalistics.

 

Todd Merrill:

It’s not going to be the thing.

 

Bryan Dennstedt:

It’s right. Exactly. That’s exactly right. Cause it’s like, they’re still in a capitalistic society. There’s still going to be competition. There’s still going to be competing on that front, but, you know, somebody is going to break through this barrier, and the robots are coming.

 

Todd Merrill:

2026 is this year healthcare gets disrupted, finally.

 

Bryan Dennstedt:

Gosh, that’s a tough one. I am working with so many healthcare companies that are doing their darndest to make sure it happens. I definitely think, you know, we’re past the light bulb stage. As I mentioned way early, you know, there’s some big changes coming where we’re not just putting a scribe in place, but at the same time, the incumbents in the institutions that we’ve built up over the past hundred years are going to be extremely hard to break and change and get to the heart of it.

 

Todd Merrill:

Yeah

 

Bryan Dennstedt:

So, I’m not sure.

 

Todd Merrill:

I look at these monster mega companies, and they just can’t get out of their own way, and they’re just hemorrhaging millions of dollars in lost revenue opportunities. And then, they won’t spend 50,000 bucks or a hundred thousand bucks to explore a couple of quick solutions, like, it just mind-boggling.

 

Bryan Dennstedt:

That’s right. I mean, I think the story this year in ‘26 isn’t intelligence-related. I think it’s like alignment. Technology last two years has moved faster than institutions, companies, and our people, and we’ve got to catch up now.

 

Todd Merrill:

I think that’s the theme for 2026, absorption, right? Tech is moving so fast, and it’s going to get out over our skis a little bit, and then everybody’s got to kind of catch up. 

 

Bryan Dennstedt:

Yep. 

 

Todd Merrill:

Well, I think we’re at time. So, any last topics you want to throw out there before you hang up on 2025?

 

Bryan Dennstedt:

We both have a list of another 15 or so. So, maybe …

 

Todd Merrill:

… we need another podcast.

 

Bryan Dennstedt:

We do a Valentine’s Day special or something.

 

Todd Merrill:

All right, let’s do it next time. 

 

Bryan Dennstedt:

Yeah

 

Todd Merrill:

On your show. We’ll do it on your show next time. How about that? 

 

Bryan Dennstedt:

Perfect

 

Todd Merrill:

All right

 

Bryan Dennstedt:

I’ll line it up. 

 

Todd Merrill:

All right. What’s your podcast?

 

Bryan Dennstedt:

Check out AIwithBry.com. You can learn all about AI. We talk about learning, leveraging, and leading with AI. So, very similar veins, but we’re both here, Todd, to help change the companies and set them on the right trajectory with AI in a big way. So, I appreciate you having me on the show again.

 

Todd Merrill:

Yeah. Thanks, Bryan. It’s always fun.

What is the Sky Lounge?

Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

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ABOUT OUR HOST

Todd Merrill, Interim and Fractional CTO, CISO

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Connect with and learn more about Todd here:

email: Todd@SilverbackCTO.com
phone: +1 678-521-5305
calendar: FantastiCal.App
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