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The Wartime CEO

The Panel

November 13, 2026

This week we start with Justin’s return to Twitter (November 28, so mark your calendars) and then dig into Brian Halligan coming back as HubSpot CEO to “refound” the company.

Speakers Justin Jackson, Brian Casel, Jordan Gal

TopicsEntrepreneurshipBusinessTechnology

Justin Jackson (0:19)

Welcome to The Panel, where founders talk about building a better business and a better life. I'm Justin Jackson, co-founder of Transistor.fm.

Brian Casel (0:27)

And I'm Brian Casel, founder of Builder Methods.

Jordan Gal (0:29)

And I'm Jordan Gal, founder at heyrosie.com. Great to be back, gents.

Justin Jackson (0:34)

Happy Friday. By the way, it was really nice to hear from Danny Postma on Twitter.

He gave the podcast a shout out. I think this is also just an example of like, people, you think you're doing all the marketing, you think everybody knows about what you're doing. And here's Danny, he's like, he says, I can't believe the legends that got me into startups years and years ago, have a podcast together. I thought you all quit your pods, Justin, Brian and Jordan. So, like, here's the deal, you know, so much of life is just, you got to keep going.

Obviously, we want to make this show the best we can. And obviously, you know, it's got to be good, but it's just nice to hear from someone who's just hearing about us for the first time.

Brian Casel (1:27)

So, I'll tell you what our biggest marketing problem is on this podcast, and that is Justin not being back on Twitter yet. We need our hype man back.

Jordan Gal (1:36)

I know.

Justin Jackson (1:40)

The countdown is on. I think I'm gonna be back late November, folks, so.

Jordan Gal (1:45)

Oh, no way. Okay.

Justin Jackson (1:46)

Yeah, November 28, I think, is when I'll return. There we go. So.

Jordan Gal (1:52)

Is it gonna coincide with, like, Elon being indicted?

Justin Jackson (1:55)

Oh, it did. Yeah. Yeah.

Jordan Gal (1:56)

The Dems are back. Justin feels safe to bring it back in. I've got insider information, you know?

Justin Jackson (2:01)

Turns out, I've been sleeping with Elon and, uh...

I got some inside info. Talking about CEOs, you know, we had... There's this whole Jensen thing and Nvidia, but, Jordan, you talked about wartime CEOs, people coming back to run their company. What's going on here?

Jordan Gal (2:24)

All right, so I just posted a link to the tweet from Brian Halligan.

Justin Jackson (2:28)

Yes.

Jordan Gal (2:29)

Right, co-founder and previous CEO at HubSpot, now publicly traded, and he's coming back as CEO and made an announcement. Uh, Darmesh and I are completely refounding the company. It's day one. Like, all right, it's a, you know, five billion ARR, ten billion market cap, 15 year old company that's gone public, whatever, you know, very established. And the way he put it is interesting, refounding the company. Yeah. Day one.

Here's my honest reaction to this was negative.

This is not a good sign. Okay. It's almost like I'm rooting for them. Like, hell yeah. Like, take control. Yeah. He's got, I don't even know, $100, $200 million of HubSpot equity as the original co-founder. Like, his wealth is tied up in it. All this other stuff. But he still wants to play ball. He wants to come back and get back to work, which hell yeah. So I think we're going to root for him. This isn't the first choice, right? This is not the happy path.

Justin Jackson (3:37)

Yeah.

Jordan Gal (3:38)

This is like, all right, I did the founding thing. I did the start thing. We scaled up. We went public, you know, cheers all around. And now I'm going to step aside and let another CEO come in.

To go back in, that to me signals a lot of worry. It's not that no one's going to get it right, but me, it's I am most likely to get this right because of the DNA and founding the company and understanding the team and all this other stuff. And so how do we give this company the best chance to not just kind of slowly sink into irrelevance is I'm going back in. I'm going to take over CEO. I'm going to refound the company. Now HubSpot has access to capital. They have partners. They have name brand recognition. So I do think they can do a lot with those resources and their mindset, their startup guys to begin with.

I am very interested to see how they do, but it worries me to see this.

Brian Casel (4:36)

I agree. That was my first takeaway when I saw the tweet too. It was like, not only is he making the decision like it has to be me to come back, but it's also like the framing of the announcement is like, this is day one, we are reimagining what HubSpot is. All of that, to me, the takeaway is like, this is an acknowledgement of something is wrong and it needs fixing.

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