Valuetainment - ＂I Drove The Company＂ - Ex-Daily Wire CEO Says Replacing Him Wasn't Easy

00:00:00.000 Do you miss being the CEO of Daily Wire versus being a content creator today?

00:00:05.460 I know you're still running a business, you're a business guy, but do you miss being an operator?

00:00:09.520 Absolutely, yeah.

00:00:10.760 What do you miss about it?

00:00:11.720 Well, my ambition has never been to be a podcast host.

00:00:14.800 At one time, I owned and operated one of the 10 largest podcast companies in the country.

00:00:20.240 It would have been very easy to launch a podcast during those days.

00:00:22.860 On this side of the Daily Wire, it's actually challenging.

00:00:25.360 So you never did, you never had a podcast.

00:00:26.940 I hosted our backstage show, which we all got together once a month.

00:00:31.180 Every now and then, if there was some thing that we felt like the CEO of the Daily Wire needs to weigh in,

00:00:35.940 I would do a little one-off speak to the audience or a town hall or something.

00:00:40.220 But no, I've never tried to be in the hosting grind the way I am now.

00:00:44.260 How do you like it now?

00:00:46.540 It's an act of creation, so I love that.

00:00:48.540 I like having a voice back after spending a year kind of in the wilderness after leaving Daily Wire.

00:00:54.340 I like having my team back together and being in motion again.

00:00:58.000 But, you know, there's nothing like the thrill of running a business, of running a business at scale.

00:01:02.820 We had 275-plus employees when I left and, you know, a couple hundred million dollars of annual revenue.

00:01:09.260 You know, that's an enormous amount of pressure that always forces you to be your very best.

00:01:15.200 And, you know, it's addictive.

00:01:16.360 You know better than anyone that's an addictive lifestyle.

00:01:18.860 Yeah. So do you think like sometimes because sometimes when when there's a there's a guy like you and I wonder how you're going to answer this.

00:01:25.640 Sometimes when there's a guy like you, when you're working with a guy like you, it's annoying.

00:01:30.280 OK, but when the guy leaves, you also say, shit, he did a lot of stuff we didn't even think about.

00:01:36.080 You know, it's kind of like that guy was doing this and he was doing this.

00:01:39.640 Yes, he was annoying. Yes, he was kicking our ass. Yes, he was difficult.

00:01:42.420 Yes, he was, you know, thought very highly of himself and all this stuff.

00:01:45.800 But my God, it's tough to replace this guy.

00:01:48.060 Do you think something like that happened after you left?

00:01:51.460 You'd like to think so.

00:01:53.060 I know that I wasn't an easy guy to work for.

00:01:55.320 I used to, we used to have, we'd start our day every day with what we called the 1030 meeting where we would get an assortment of people together from the top executives in the company to a lot of the management of the company.

00:02:06.540 And we would just make sure that everyone was sort of chasing the same set of priorities, especially in a news business.

00:02:11.880 You know, it's very dynamic.

00:02:13.060 like things change every day that require an immediate pivot, some story break, some opportunity

00:02:17.460 for one of the hosts appears. Those aren't things that you plan weeks or even days in advance. So

00:02:22.300 you have to be very responsive. And I would often say in the 1030 meeting, you know,

00:02:27.860 I know that I'm a difficult person to work for. I know that if you're looking for work-life

00:02:32.460 balance, this probably isn't the company for you. I don't really believe in the concept of

00:02:36.100 work-life balance. We're building a rocket ship while it's in flight. And that's one of the

00:02:41.640 hardest things you can ever do, but that's what we have to do to pursue the mission of the company.

00:02:47.520 And so in that way, I'm certainly aware that I was a tough boss, but I'm also aware that I really

00:02:56.060 drove the company. The style of leadership at the time was very hands-on, and I was very in the

00:03:04.180 weeds with my team and every day choosing a direction, ordering the priorities of the company

00:03:11.760 and keeping everyone on mission, which, you know, this is, I think it's probably true in every

00:03:17.020 business, but it's particularly true in an ideology first business, that you both have

00:03:22.800 business objectives and missional objectives. And resolving the tension between those two things

00:03:28.400 was also a huge part of what I was engaged in in leadership. And listen, I'm not the only

00:03:33.180 person on earth who can do it but i i suspect that there's some pain points in the transition

00:03:37.960 yeah how do you find because i think who who replaced you caleb the other third one who's

00:03:44.720 the top three big partners are you ben and caleb right so caleb took over but then caleb recently

00:03:50.140 stepped down in the third week of may or fourth week of may and then the new guy is the jeopardy

00:03:54.580 guy or the wheel of fortune guy yeah mike richards is his name so was it intentional for caleb to

00:04:00.680 only go for 12 months or, you know, however long it was, and then to bring somebody else in? Was

00:04:04.000 that an intentional part of strategy? Yeah, you know, I can't really speak to that. That wasn't

00:04:09.220 your decision. That was post. My breakup with the company is a true breakup. You know, I left in

00:04:14.680 2025 in March. And other than, you know, the kind of contractual commitment, you know,

00:04:23.440 a breakup of this nature obviously comes with a lot of lingering commitments and lingering

00:04:27.980 restrictive covenants, and I own a very tiny piece of the company now that's probably primarily

00:04:35.040 a part of the enforcement mechanism behind restrictive covenants as much as anything,

00:04:39.900 but I'm not a part of the company. I haven't spoken to anyone at the company

00:04:43.400 in any sort of official capacity in, I guess, almost 18 months now, so I can't really speak

00:04:50.260 to what happened with Caleb in the last few weeks. Got it. Are you still in touch with them? Are you

00:04:54.540 still in touch with Caleb and Ben? Do you guys still communicate? No. No communication? No, I've

00:05:00.360 said publicly before, Ben reached out to me the day that Charlie was assassinated. Obviously,

00:05:05.160 we met Charlie on the same day when Charlie was only a teenager. And in some ways, I feel like

00:05:10.420 TPUSA, The Daily Wire, and PragerU all kind of came up at the same time and to varying degrees

00:05:16.860 came up together. You know, there were times where we saw each other as rivals, I'm sure. You know,

00:05:22.320 it's a competitive space but for the most part we were we were friends and we were building our

00:05:27.480 businesses at the same time and in the same space and so you know that was a as it was for for

00:05:35.580 everyone it was a very painful moment and it was nice to hear from ben in that in that moment but

00:05:40.720 you know we're not we're not in a place in our relationships right now where we

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Valuetainment - June 18, 2026

＂I Drove The Company＂ - Ex-Daily Wire CEO Says Replacing Him Wasn't Easy

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