How Guild AI discovered their real buyers weren't developers — and rebuilt their GTM motion around CIOs and CSOs | James Everingham

**James Everingham** (0:00)
If you think about why VPNs and the cyber security software business popped up, there was intentionally bad actors out there trying to compromise your company infrastructure.
It's like now we have a different problem when you start using AI. You have these unintentionally bad actors possibly trying to take down your infrastructure from within.

**SPEAKER_3** (0:22)
Welcome back to another episode of Builders. As always, this show is brought to you by frontlines.io, Silicon Valley's leading B2B podcast production studio. If you're bringing technology to market and want to learn from your peers, we have a library of more than 1200 interviews with venture-backed founders and marketers where they talk all things go to market. Of course, if you want to launch your own podcast, we offer podcasts as a service to more than 80 tech startups. The idea there is very simple. You show up and host and we do everything else. Now with all that said, let's jump into today's episode.
Today, we're speaking with James Everingham, CEO of Guild AI. James, welcome to the show.

**James Everingham** (1:01)
Thanks for having me on, excited to be here.

**SPEAKER_3** (1:03)
Of course, looking forward to this conversation. You're a five-time founder, you have a lot of history, a lot of things that we can talk about. I want to talk about something very specific, and I want to go back to 1987, the founding of your first company. What was it like to be building technology companies in the late 80s?

**James Everingham** (1:17)
Well, you know, it was actually pretty challenging. I was pretty young, I didn't really know what I was doing. And to make it even harder, I was in Central Pennsylvania, I was in Silicon Valley. So finding capital was a struggle. I think the first time I walked into a bank, I had shorts on and asked for a $25,000 loan and they laughed at me. But I think 13 trips to the bank and I finally got my act down. It was harder. I mean, technology, the market was smaller.
It was more complicated to build things and to get things going. My first company, the reason I even started it is because I had some open-source software. Back then, it was called freeware or shareware. You'd basically say, hey, if you find value, maybe donate or send me some money.
People were sending me a lot of money. So I'm like, well, hey, maybe I should try to turn this into a company. So it wasn't a thesis, it was also a working product that I had to tee off of to get that going.

**SPEAKER_3** (2:08)
I feel like now tech is very mainstream. It wouldn't surprise me someone from Pennsylvania or Wisconsin or like Zimbabwe is into tech now. But back in the late 80s, like you said, being there, what was your exposure to tech in the first place?

**James Everingham** (2:22)
I didn't even think tech could be a possible career path when I was growing up. It was computers. I didn't really know much about them. I started using them early in high school. My mother would be very upset thinking I was spending all my time on this video game, she called it.
It just wasn't a career path. It was actually even more like a blue-collar work back then. My first job, which was before I started my company, was actually working at the university at Penn State.
I had to be there at 8 a.m. I had to wear khakis and a dress shirt. I had to stay till exactly 5 p.m. It was a very different career back then. It had much less impact. Once again, there wasn't a lot of computers, so it was just completely different.

**SPEAKER_3** (3:05)
When you take a look at these five different companies, is there a through line? Is there something similar? Is there a pattern?

**James Everingham** (3:10)
I would say the pattern for me personally, there has been following what I'm passionate about.
I never really set out in my mind with, look, I want to start a company. That wasn't always my goal. My goal was, I've had an observation that I think is important that I could build something interesting, and I want to get it out to the rest of the world. I did try to start a company once because I just wanted to start a company and that was my failure.

**SPEAKER_3** (3:38)
That says something.
Let's talk a little bit about what you're building today, and I want to go deep on the product, but maybe let's talk about how you decided to make this the fifth company. I'm sure if you're like a lot of other founders I know, myself included, I have a long list on the notepad of ideas, things I could go after. What was it about this problem that made you say, yep, that's it, number five, let's go?