In this conversational interview, Matt Paulson and the host discuss the gap between AI hype and its practical limits in running a business. They note that while AI tools are increasingly powerful, they cannot replace human decision‑making or run a company autonomously. The conversation moves to how AI has become a mandatory narrative in startup pitches, likening it to past trends where every company highlighted diversity or inclusion. Paulson argues that the most valuable opportunities lie in work AI cannot automate—particularly skilled trades such as plumbing and electrical work, which are seeing soaring hourly rates and attracting private‑equity roll‑up interest. He cautions that the e‑commerce roll‑up failures of the past may repeat in the trade space if investors overlook the hands‑on nature of the work. The interview then shifts to Paulson’s personal experience trying to sell his media company, MarketBeat. After receiving low‑multiple offers in 2016 and dealing with family challenges—including two NICU births—he decided to retain ownership, later rejecting overtures from private‑equity firms. He reflects on how personal life events, burnout, and the realization that selling would not materially change his lifestyle shaped his decision. The discussion concludes with a philosophical take on the operator versus owner mindset, using a Walt Disney anecdote to illustrate the idea of designing a personal sandbox rather than choosing a false binary between ownership and operation. Throughout, Paulson emphasizes a cautious, experience‑driven approach to AI, valuation trends, and entrepreneurship.
Chapters
I think about, Matt, as I got rid of my last company with payroll and like as I've just got my coaching business, like my God, the amount of shit I'm able to do with AI right now is fantastic, you know? But it's not like I can't like just ask it to do, like it's not gonna take the business and run with it. So it's very interesting to me where, and like, and from what I've gathered too, like the LLM structure, they don't even see a path to AGI. Compared to like, I don't know, it's just fascinating to hear you say it.
And yeah, well, I remember when GPT-4 came out and it was like such a big deal and frankly it was, but like people was like, I'm gonna start a business and ChatGPT is gonna be my boss and I'm gonna work for it. And like, obviously that didn't work out. Like those people don't have businesses today.
Um, are you seeing this stuff come up in, um, in your pitches or how, like, how are you seeing, so when I say stuff here, let me clarify. So what I have noticed, um, With the boardroom playbook that I've got, I mean, everything ends up coming down to cash and to financials and how the business produces more cash. So it becomes this first principle constraint that's deterministic, and it's becoming more and more aware. I become more and more aware of how many advisors and consultants have no idea what they're doing because they plug it in and they give you something and you're like, it's just wrong. But they don't know that it's wrong.
Yeah.
And like, are you seeing like, how are you, how is that, is that coming up in places that, yeah, I don't know.
You know, every startup we talk to has an AI story of some kind. You know, I think you just kind of, it's like something you have to do. Like, you know, if it was 2020, everybody would have their slide about like how we're being inclusive, right? And then like, society changes and like that's not the thing anymore. And now it's 2025 and everybody has to have the AI, like here's how we're gonna do AI. And 5 years from now it'll be like, here's how we're gonna use humanoid robots or whatever the thing is, right?
Yeah.
Yeah. So it just like, part of it's like the, the, the narrative is this and I gotta go along with it. So here's my story.
I have to at least address it to some degree.
Yeah. But, but a lot of it just like, it's like, I don't know, it just, I, I don't think every business in the world needs AI to succeed. Like, I think what will become more valuable is the stuff that AI can't automate. Like, you know, plumbers making $100 an hour is like going to be a real thing very soon, if it's not already, because like, no, you know, not many people want to do it and it's a very valuable thing that we all need. And like, yeah, the trades, it's going to be a great time to be in the trades.
Oh my God, Matt, the, uh, the trades up in the Twin Cities, I mean, you're $150 an hour for electricians, plumbers. I mean, like, I'm seeing it already. And it'd be really interesting as the private equity roll-ups in the trade space come to fruition, because with the debt being more expensive and then the inflation on the payroll, it'd be interesting to see if all these roll-ups that everybody thought were so obvious 5 years ago come to fruition on the back end.
Well, I mean, we saw how it played out in e-com space. Like, it obviously didn't end well, right? I think we'll probably see some of that in the trade space, but there's a reason these businesses are hard and not everybody starts them. You can't abstract away all of the actual work that happens to happen.
That was so well said. Oh my God. What allowed you to— What was your experience over the last 10 years of the hype of selling businesses, right? Because you saw it in the e-commerce space, you saw it in the digital space. I mean, and then 2020, it ramped up with all the cheap debt and the free money. Like, what kept you from having, or did you have those conversations? How did you stay focused?
I did try to sell my business in 2016 and nobody offered me like more than 3 times EBITDA, and then I didn't sell it. So like, yeah, I kind of fell for the hype cycle for a little bit, and we had some personal stuff going on in our family that like made me think like, I just need a break from work for a while. But like the right offer never came. I told the guys at the brokerage that we were working with, like, somebody wants to offer me 4 times EBITDA today, like, I'll probably, you know, take it. And I got like 3 and then they were surprised when I didn't want to take it and it's like, well, whatever, I'm going to go back to work now. And then like from there, like, you know, things at home kind of settled down and like we had— so we had 2 NICU babies is kind of the deal. My wife had 2 tough pregnancies and like, but like that settled down. Kids are fine, just kind of went back to work and then like eventually, like I realized, oh, this is actually something pretty special. I should probably hold on to it. And now it's like I don't take the emails, I don't take the phone calls from private equity venture people. There's a firm that bought another financial media company in our space and they reached out and I was like, "Well, just so you're aware, I'm never going to sell MarketBeat and I'm not acquiring any businesses. So if you want to talk, that's fine. Just know that I'm not for sale and I'm not buying." And then for some reason, they never followed up.
I can only imagine that from 2016 to call it 2021 or '22, the multiples doubled, tripled, or whatever it could have been. And did you ever think about— because maybe you might not have gotten it, but I think what I've seen over the last 6, 7 years has been actually overpaying for a lot of these companies. So did that ever change your mindset?
Eventually I had enough money where it didn't matter. There's a lot like people sell for life-changing money, but like, you know, if I had sold MarketBeat, it probably wasn't going to change my life at all. Like we weren't going to move houses or like, yeah, we kind of already bought all the stuff we wanted to buy other than like the jet. Like, so it just like didn't matter at that point. Like I just kind of like doing the thing and I want to keep doing the thing. The other thing that I've noticed in town here, I've got some friends who have kind of built businesses to say mid-seven figures up to the eight figures, even one nine figures. Who have sold their businesses, all kind of guys my age. And then like after they sell and get out of the thing, like they either don't have anything to do or the next thing is not nearly as cool as the first thing they did. Like I've seen it happen like 4 times here in town and like, it's like, I see that happen to you. I'm not going to do that.
You're talking to one right here, by the way. Yeah. And like, it's a It is so such a— and that is why this concept of like you have a— there's this operator role and there's this ownership role and just understanding. I mean, Matt, after— I mean, again, it's been almost 10 years since you saw that presentation that I did where I like the messaging tweaked over and over as I learn more and more.
The—
it's a false choice, I think, of like when someone— because like it sounds like when you were having the family stuff, it's like, okay, well, I'm, I'm exhausted. But then it's like we commingle the asset versus is the job. And like, and that's why, you know, you were explaining how you tinker around in the stuff that you love and then you give yourself space. Like, I— there was this story about Walt Disney that really resonated with me, Matt. So his brother Roy was like his, like, co-partner or whatever, like doing all this stuff. And when he built out Disney World, he's like, I just want to play for the rest of my life. And that's how I think about business. And it's like, hey, like, you can design your own little sandbox. Yeah.
