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Ryan Denehy

Ryan Denehy

Entrepreneur

Oct 20, 2026

7:33
Like, where do you think they're wrong? And where do you think they're right? And like, what's changed since, you know, you first started? Yeah, I think plenty of
7:39
people will make money with AI roll ups.
7:43
But I'm very skeptical that the fundamentally different economics that many of them are underwriting to will actually materialize.
7:55
Too many people that I've talked to that are looking at these AI roll-ups have never actually operated these businesses or done a roll-up pre-AI.
8:03
at all.
8:04
And so it's very easy as a venture investor to look at something like an IT services business in a vacuum and say, okay, all things being equal, we inject AI and get rid of all of the repetitive labor.
8:19
drive a ton of margin expansion a lot of profitability and then we can sort of automate this go-to-market motion that assumes a that all of those things are happening while everything else in the business into the market remains true which it's not there's immense downward pricing pressure so what what i'm hearing from some of the other i.t services roll-ups is that most of the margin expansion that's coming from ai now is a coming from off-the-shelf tools that the 15 other pe-backed roll-ups all have access to and b while that's happening they're losing pricing power over their customers because customers are expecting so much more for less money when your alternative isn't just an i.t service provider it's a gazillion different chatbots that you can go use.

23 MINS LATER

31:55
afternoon that's crazy
10:16
Big time
10:17
... start, s- start there.
10:19
It would've been so easy for us in 2023 to sit there and pat ourselves on the back and say, "Wow, another huge year.
10:28
We got plenty of cash.
10:30
We're number one in our category.
10:32
You know, we, we haven't missed a quarter in ages." You know, all of that.
10:36
Fortunately, we've got a, you know, a smart team, a really smart group of investors around the table, and, and we were like, "Hey, let's, like, read the tea leaves here.

28 MINS LATER

38:33
For anyone who wants to sell their company and are looking at public companies as a prospective buyer and acquirer, like, what are some of the tips you have around public companies specifically?

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