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June 4, 2026 54 mins

Todd Ricketts — Chicago Cubs co-owner and founder of Freespoke, the search engine that labels news sources with media bias ratings — joins the Chuck Toddcast for a wide-ranging conversation that bridges the increasingly intertwined worlds of media, technology, and professional sports. Ricketts makes the case that when people are given genuinely good information from across the ideological spectrum, they tend to arrive at good answers — and that Freespoke's mission is to present all sides and then get out of the way, rather than letting ad sales determine what news you see. He pushes back on the idea that the market alone can solve the data privacy crisis, arguing data may eventually need to be regulated like a utility but that nothing changes until there's a major "event" that creates real public groundswell. Ricketts is candid about Freespoke's challenges — paywalls remain a real obstacle, the left/right labeling is imperfect and done by outside groups, and the political landscape itself is shifting in ways that scramble the traditional categories . He observes that podcasts have become a primary news source because people clearly hunger for long-form content with nuance, that politicians are now visibly afraid of giving long answers because they might get clipped, and that legacy media still doesn't seem to understand why its audience has migrated elsewhere.

The second half pivots into the business of running a baseball team, and Ricketts brings the same straight-talking pragmatism to MLB's looming economic crisis. He argues you cannot sell a salary cap to MLB owners without genuine revenue sharing, because if the league itself isn't competitive then everyone eventually loses — including the owners writing the biggest checks. Players currently take roughly 48% of revenue, a number he expects to climb to around 52% in the next deal, and Ricketts is honest that half of MLB's franchises are still essentially mom-and-pop operations even as private equity money is rapidly entering the sport. He talks about the difficulty of running any sports team in 2026 because fans genuinely feel like they own the franchise, why ownership groups are increasingly building entire entertainment districts around their ballparks to control the fan experience end-to-end, and the painful broadcast rights question every team is wrestling with: fans have cut the cord, the old TV economics no longer work, and ownership has to be flexible with new broadcast partners even as they ask themselves whether season ticket holders should be entitled to free access to every game. Ricketts closes by laying out what would qualify as a disappointing season for the Cubs — a sober assessment from an owner who has watched the economics of his sport, and the media landscape his business depends on, both transform at the same time.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Todd Ricketts joins the Chuck ToddCast

00:45 Providing media bias ratings for online news sources

03:15 When people are given good info, they come up with good answers

03:45 Goal is to present all sides, then let people make up their mind

05:00 You don’t want ad sales for search to determine your information

07:15 Can the market fix data sales, or does the government need to regulate?

09:00 Should data be regulated like a utility?

09:30 There will need to be an “event” to cause groundswell over data privacy

10:30 Does Freespoke labeling news left/right cause users to seek their preferred source?

13:30 Politics are shifting and what used to be a “left” issue is now a right issue etc

14:15 Protectionism has become right and free trade has become left

16:00 How would someone like George Will be labled?

17:30 Labeling is done by outside groups and the labeling isn’t perfect

18:00 The company is for-profit, sells ads and has subscription model

18:45 All the search is AI curated, but people curate the current events page

19:30 Bing and Google are the direct competitors

20:15 The Freespoke algorithm tries to strip out bias

21:45 Some topics get a ton of content from one side & none from the other

23:15 People are informing themselves via podcasts instead of legacy news

24:00 Legacy media needs to understand why audience is going elsewhere

25:45 Popularity of podcasts show people like long form content

27:00 Politicians are afraid of long answers & nuance in case they get clipped

27:30 Paywalls are a challenge for Freespoke,

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
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first box and free croissants for life when you visit
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code podcast at checkout. This is a sponsor I absolutely embrace,
so use that code. So joining me now is the
owner of the Chicago Cubs, and we're not going to

(01:45):
be talking baseball, although I might sneak in a question
or two about what's coming in the next two years.
Those of us who love baseball are worrid we're gonna
lose half a season. So I'm warning him now. I'm
warning you now, mister Reckets. I will have a labor
question towards the end. But you're on here because you've
got a new app and it's more than an app,

(02:05):
and it's sort of an interesting and I think it's
bigger than that, and I think the consumer facing app,
it's called free Spoke. I encourage people to take a
look at it right now, get your free trial right now,
and what it attempts to do. And I'm gonna let
mister Ricketts describe it in more detail, but I'll just
give you my first impressions. You know, it wants to
give you an array of perspectives. Label the perspective, so

(02:29):
you'll see left, right, and middle based on publisher leanings
rather than individual reporter leanings. And we'll get into that
a little bit. But the idea is to quote paint
the full picture. This also particularly on political topics or
on issues that are more subjective than objective. Right we

(02:50):
have in this, of course, is this this war? We
can all be claimed that it's being fought sometimes between
left and right over what is truth, what is what
is real? Et cetera. And this is one of the
more interesting answers I've seen out there. You know, All
sides media is something that I've been very curious about
for a long time, and this is a new entry

(03:10):
into this. And mister Todd Ricketts joins me. Now, so Todd,
how did I do describing it and fill in the
blanks here? Because I didn't do justice to your AI
search engine, which I find also quite interesting.

Speaker 2 (03:22):
Yeah, you know, I think you did a prety good job.
And really what we set out to do was, you know,
I'll step back to like where I came at it from.
It's like, as you look at social media and big technology,
I felt like, oftentimes you're being led down a narrative.
Oftentimes you're being let down a narrative that just reinforces
what they already know about you to a little.

Speaker 1 (03:41):
Information bias, right, It's something that the Internet is really
made that phrase, which was sort of a phrase that
was rarely used pre Internet days, to now something we
think about a lot, you know, yeah.

Speaker 2 (03:53):
And a lot of it is like, you know, these
the platforms are trying to get you to spend more
time there, but they're also just reinforcing what you see
to give you things you'd like. And what that has done,
in my opinion, is like it's kind of driven that
divide in Americans where you know, I think, you know,
in previous generations, people were Republicans or people were Democrats,

(04:13):
and maybe they talked about politics, but nobody took it
to heart in the same sort of way. And I
think we just got to a point where we couldn't
even agree on the facts because where like people are
getting driven down to their own side. And so what
I wanted to do is like create a search engine
and you know, and like a little bit of a
a search engine layered on with AI that kind of

(04:35):
takes in everything that's being published and finds that overlap
and then also kind of defines or kind of tries
to like describe each side in like normal terms, not
no name calling, just say this is how the where
these people are coming from. This is where these people
are coming from. And so you can kind of inform
yourself because I have a lot of faith in the
American people that given good information, they'll come up with

(04:58):
good answers. And so that was kind of like where
we started. And what we did was we built our
own index of the Internet, so we're not relying on
Being or Google, and then layered our own algorithm of
AI on top of that and really trained our AI
to be just the facts. Man, is it current? Is
it relevant? And is it leading? Like when? So what

(05:18):
we say is we're we're not trying to lead anybody
in a particular narrative. We're trying to present all sides,
present everything that we can find, and then let people
make them to their own mind.

Speaker 1 (05:29):
So let's talk about the search engine aspect to this,
because you know, I mean that's the part that in
some ways I'm excited to see if this will be
more functional than search in general at the moment, right,
I mean, with the big tech companies so focused on
their AI offerings, search, you know, is search is difficult,

(05:51):
and frankly everybody's search has become monetized, right, that's not
consumer friendly, it is, you know, we're the mark as
I always say, right, like you know, when you do
a search on an old school Google search, it takes
a while before you get out of sponsored content, and yeah,
that's right. Yeah, And so I would, you know, and

(06:12):
I think I'm a little nervous about just turning search
over to AI. It seems like you're trying to bridge this.

Speaker 2 (06:18):
No, definitely, definitely, And so we do protect your privacy,
so we're not tracking you like the other companies. And
you kind of said it without saying it is that
if you're on the Internet and you're getting something for free,
you are the product, like you are being sold. Your
information is being sold. They're trying to find advertisers to
match up with like what kind of tennis shoes you like,

(06:40):
or what kind of car you might buy and so on,
and so you're being sold out there, and there's a real,
like I think, long term privacy concern about that because
maybe people are like, well, I like seeing the ad
from my favorite shoe company and knowing what they're putting
out there. But then you're like, where does it stop?
And how do you how do you maintain control of that?
And also, you know, we want to make sure that

(07:01):
the people that are buying the ads aren't driving the
content you're seeing, like you're saying, like you get a
bunch of advertising your sponsored content to the beginning. So
we're trying to avoid all that and really just bring
the best information we can in front of people. And
when you think about all the AI platforms, whether it
be Chat, GBT or Gemini or what have you, that

(07:21):
still is search. It's not that different than what.

Speaker 1 (07:25):
No, it's just it's curated search essentially.

Speaker 2 (07:28):
Yeah, and it's a thousand times faster. Right If Google,
a regular Google search could come up with something a
thousand times faster, it can just come up with something
that's a little more elaborate and a little more catered
and curated to you, and so it's all about like, Okay, well,
where are those people getting their content and how are
they where are the platform is getting their content? And
how much of it is Reddit and how much of

(07:49):
it is coming from being and how much physic is
coming from Google and other sources.

Speaker 1 (07:53):
You know, it's interesting. You're not the first baseball owner
I've had this conversation with. Well, really, Frank McCourt project Liberty,
Are you familiar with what he has been trying to do,
because you guys are on the same page, and you know, yeah,
And I understood sort of where he came at this,

(08:16):
and I always sort of really much empathized. He said,
you know, fifteen years later, the first five things when
you google Frank McCord is something that happened in his
life fifteen years ago, right, And it was this idea
that you had no control over your own identity and
his whole philosophy. And I think it's it's admirable. But
I don't know how we put this toothpaste back in.

(08:37):
But I feel like you're going down this road too,
which is instead of that us seeking permission of the
tech companies to use their product, that Essentially, apps or
tech companies ask our permission to monetize us, and while
they are technically asking our permission, we're being coerced because
if you don't accept the terms and conditions, you don't

(08:57):
get the updated bells and whistles. Is this something the
market can fix or is government going to have to intervene?

Speaker 2 (09:06):
Well, just to go back to Frank, I think I
think Frank has another layer to what he's trying to
do too, is that, like, and if you're going to
take the information you know about me and take you
to the market and sell it, I deserve to cut
of that. I deserve to get I deserve to get
paid on that somehow. So I'm using your product. It's free,
for sure, But if you're going to go sell information

(09:26):
about me like that that money, I have a right
to some of that as well, if I've opted into that.
And so I don't know how that lands, but I
think it's a great from the philosophical point of view,
I think it's a great idea. I should be able
to go like, well, if I'm going to be on
the Internet and they're going to sell information about me
based on my patterns, my habits, Yeah, I should I
should participate in that as well.

Speaker 1 (09:49):
Well, you know, it's funny. I remember having this large
debate with him, like you know, it's the the And
I've had this discussion with Hi people high people up
at Meadow where we've had this conversation, which is, my
data individually is not valuable, but my data coupled with
a million people in Arlington, Virginia is extraordinarily valuable. How

(10:10):
do you compensate it?

Speaker 2 (10:12):
Yeah? No, I don't know. I don't know what the
right answer is. But I love, like I say, philosophically,
I think it's the right direction, and CAS should be
a meta. I don't know how they rapidly get their
head rep aroound all the data they do have, right,
It's like they have so much they're swimming in it,
and I'm sure that they have trouble trying to keep
it organized themselves.

Speaker 1 (10:30):
Well, And I guess that's the question, is should data
be regulated like a public utility? Is data electricity?

Speaker 2 (10:37):
Yeah, that's a great question.

Speaker 1 (10:39):
I don't you know. I think this is a I mean,
it sounds like you believe this is an issue that
our politicians out of debate. Rather do you have an
opinion on this.

Speaker 2 (10:47):
Well, what I think is it has to happen, is
it has to come from society, like people have to
and I think at some point there's going to be
some sort of event that will make it clear to
people that they should be more we're concerned about their
their Internet identity and how their information is being shared
and who has it and so on. And I think
it has to be people saying like, I'm concerned about

(11:09):
who has my information, and it has to be that
sort of ground swell up before we're going to get
a top down sort of answer. And I feel like
if you if it comes from that direction, then we're
going to get a better answer anyway, because it'll be
come from people expressing their concerns and wanting to control
their own information.

Speaker 1 (11:27):
One of the hallmarks of your app is that it
is that it, you know, protecting my privacy, right the
ideas you're protecting user privacy. So this next question I'm asking,
I wonder if this if the if your protection of
privacy gets in the way from you be able to
search the following. But you know, one of the things
with labeling news does it come from the left, right,

(11:48):
or center, is that it becomes almost like a a
a neon sign for those that want their news that way.
And what you find out and what I think I
have frustratingly found out myself and maybe, and I'm curious
if you guys have been able to do some research,
is that while people say they want all perspectives, they

(12:11):
usually only look at one one. Have you been able
to denote, you know, without violating people's privacy, do the labels?
Because this is where I'm torn on the labels. In
this respect, I think the label should be there. I
would just argue put them at the end of the
article and humor me a minute, which is, if you

(12:32):
add the label, then automatically I'm going to our brains, right,
You're just going to read it. I almost like read
it as if somebody from stage left is saying it
or somebody from stage right, versus consuming it, forming my
own opinion and then seeing, oh, this came from stage
left or this came from stage right. And look, it's

(12:53):
a small thing. But I'm curious if you guys had
a debate where do you put the label? You put
it high and very prominent, and on one hand, that's
the premise of free spoke, right, So I get it,
but if you had all done any consumer research of
how people are using the labels.

Speaker 2 (13:11):
You know, I don't know if we've had like that
sort of like sort of survey of where to where
to label it or how people feel about it. My
hope is that when people see those labels, that they'll
see something that's left and see something that's right and
read both articles, or they can kind of come down
to our perspectives where it kind of shows that consensus
and that overlap. But we haven't done anything specific about

(13:33):
trying to track people and if people have patterns of
like this individual goes to it clicks on everything that
says left, or that individual's clicks on everything that says right. Yeah,
but we would have trouble finding that because we do
protect people's privacy and we don't track people in that manner.

Speaker 1 (13:49):
No, it's something because look, I say this as somebody
building my own you know it is you. If you
don't tack you know, essentially prominent left or prominent right,
it is a slower build than if you signpost right.
And the irony is that that's been the conundrum of
American politics. We all kind of revert to the mean

(14:14):
of somewhere between the thirty five yard lines right when
push comes to shove, and yet the dialogue is inside
is on the other side of those thirty five yard
lines in both perspectives, right and so, and the middle
is hard to find, especially we're in the middle of
a pre a realignment todd you know, meaning that you
know what was left is right on some things, like

(14:38):
take the issue of trade free traders are left owners
and protectionist, right, That's what I grew up, right.

Speaker 2 (14:44):
It's it's I would say that in this moment and
this strategy that the President is using to try to
get to it, I think what he wants to do well,
he definitely wants to enshore some of the manufacturers, but
I think in the end what he wants is just
better trade deals than we've had historically. And so I
don't know if like the president necessarily wants terifs forever
he talks in those terms because he's always he's selling ideas,

(15:06):
he's and he's pushing the developer way.

Speaker 1 (15:08):
He speaks like every developer the inabsolute you know, it's
kind of the greatest ever, the biggest ever, the most ever.
I mean, you know, yes, you know he is sort
of a developer first.

Speaker 2 (15:19):
Well, I think I think, like you know, Scott Pascenta
said it a bunch of times that you know, if
other countries got rid of their tariffs, we'd get rid
of all of ours as well, and so it's kind
of trying to like land in this place where there's
just a little less protectionism going on around the world.
And I come at him from this view of like
in nineteen forty five, we signed trade deals with everybody
saying like, we'll buy all the products you can make,

(15:40):
and we're going to secure the sea lane so your
products can make it to the United States, and we
weren't so concerned about what they were going to buy
back from US, and so we had these like one
sided trade deals, and over time that has worked against us.
In the nineties and the early two thousands, we were
like everybody was like this, free trade, free trade, free trade,
Republicans and Democrats alike. And I think the idea that
was sold on everybody at that time was we're going

(16:03):
to take manufacturing from towns like Youngstown, Ohio, and that
may go to Mexico, but then that's going to get
backfilled with high tech, you know, high tech service jobs.
And what happened is we saw a lot of that
manufacturing leave and not get that backfilled. So a lot
of these small cities were left with unemployment and meth
amptam right. I think that's what the President sees. It

(16:24):
sees that like this, these trade deals that have taken
manufacturing away from the US and not brought back the
promise of the high tech service jobs that was supposed
to come in their place. And he's like, well, you know,
maybe we just need to bring some of that back
on chore until we figure this out.

Speaker 1 (16:44):
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I remember during the Republican convention when I heard the
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(18:34):
the eighty four convention for Walter Mondale, you know, and
I don't. And it's and the point being is, so
this is where I I appreciate the labels, but and
I and I think you you hint at this. It's
like you want to keep them simple. But take take
George Well, right, where do you label him? Right? And

(18:58):
I say this, you know, he is to me a
classical conservative small seat.

Speaker 2 (19:03):
Yeah, yeah, that's right.

Speaker 1 (19:04):
But my guess is it doesn't fit your these labels.

Speaker 2 (19:11):
I think I think he's still he's still would be conservative.
He's just you know, maybe he's not in step with
the Republican Party at the moment. Like we just labeled
him Cubs fan and we just hold on to him.

Speaker 1 (19:20):
Hey, we Nats fans claim, you know, he goes to
more Nats games than Cubs games.

Speaker 2 (19:24):
You know, I'm sure that's true, But but he sits
next to me when he comes to Cubs games.

Speaker 1 (19:29):
Yeah, okay, but he has his own seated that's games.

Speaker 2 (19:31):
But yeah, okay, if I can say, can I get
off topic for a second and tell a cude story.
I was sitting next to him at a at a
game against the Mets years ago and Bartola Cologne was
pitching and he was like, he was like, I don't
know if he was forty four or something, and.

Speaker 1 (19:47):
I was like, I told me he was really sixty,
like though he never had his birth rate ticket, right,
I wouldn't be shocked.

Speaker 2 (19:53):
Yeah, exactly. And I'm like, hey, like, I don't all
I know is that you don't get better after forty
I'm like, he must be taking something. I don't know
what it is. And uh, he came out of the
bullpen and you know he at that time, he probably
weighed two hundred and fifty pounds. He was big, he was.
And he's not like super tall either, he was big.

(20:13):
George was city next to me. He's like, you think
that guy is on steroids. And I'm like, well, steroids
and burritos, baby, but yeah, I've had some good times
in Georgia. Oh, it's not to get too off topic.
I know we're talking about.

Speaker 1 (20:28):
No, no, no, yeah, and I guess that that's my you know.
You know it's funny about political labels, is it's everybody
wants them for everybody else, but not themselves.

Speaker 2 (20:38):
Yeah. Well, everybody thinks they're in the middle, right, everybody
thinks they're that they're they're like the middle of everything,
and uh so it's tough. And and again, yeah, it's
not a perfect system that we have. We we kind
of use outside outside groups that that label content. We
have we have the ability to label it in house,
but we haven't started doing that ourselves yet, so we

(20:59):
looked kind of outside. So it's really just more of
a guy. It's not meant to be this this overarching
black and white of because even even within left and right,
there's like a good range of you know, of spectrum there.

Speaker 1 (21:12):
Well, let me ask this, is this a for profit
or nonprofit?

Speaker 2 (21:15):
It's for profit. Yeah, and so we we do we
do sell ads like and and we do have a
premium service where you can pay five dollars a month
to customize your experience and and put in some of
your preferences. And we're sort of elaborating on that and
trying to expand that out a little bit. So it
is for profit and like you say, like we do
generate revenues that way. We just don't do in the

(21:37):
same way that that other search engines or other platforms
have historically.

Speaker 1 (21:42):
And so what is your how many human beings are
curating and how much of this is is AI is
sort of some you know, sort of audio some sort
of automation, Like how much of the human curation is
in is in the editorial process.

Speaker 2 (22:00):
So when you uh, when you come to the side
everything that you do, as far as when you search,
when you type anything into the bar, that is going
to be automatic from our AI layered onto our our index.
But when it comes to like the current event we
have we do have people to kind of put up
like the current event news that are that's on the homepage,

(22:22):
and that's curated by humans, and that's really just trying
to identify the top stories of the day and kind
of like yeah, give like what's breaking and keep things
current and relevant on that homepage. So that's the only
part that's really human curated.

Speaker 1 (22:38):
Do you do you me I look, I'm a I'm
believing competition whatever it is, and that your organ is
You should always want to have your organization measuring itself
against someone or some entity or what it is. Who
is free spoken? Who are you measuring yourself against it
appenk us is it being what are you measuring yourself against?

Speaker 2 (22:58):
No, I would say it's more being Google still, you know,
those would be that those would be the people we're
looking at. And then because we do have that that
kind of AI larying, if you're spending your time on
chatchibt and Jemini, I always tell people like go ahead,
like compare compared to like the results you get under
from the AI platforms too, to what you're getting at
free spoke.

Speaker 1 (23:19):
Explain how your large language model works. So if I
if you're using Claude or chatchbt for research, Yeah, what
what is the you know, give me, give me the
give me, give me your pitch of why it's better
to use your large your.

Speaker 2 (23:36):
A because we really we really try to strip out
all the bias. You know, a lot of the those
the clouds that are looking if you're looking for current information,
they're looking at places like Reddit where it's there. There
is a lot of bias in Reddit, and so if
it's taking Reddit at space value, it's going to express itself.

Speaker 1 (23:55):
Do you keep Reddit completely out of your system or
how do you deal with Reddit?

Speaker 2 (23:59):
You know, what we try to do is it's not
about trying to keep people out of the system. It's
about always trying to find balance in everything we do.
So if there's if you type on a search on
some sort of topic and there's a thousand stories from
the from the right and only four stories from the left,
we're going to kind of pick four stories from the
right and four stories from the left and kind of
blend those in. So you're not just saying like saying like, oh,

(24:21):
there's only stuff on the right here. We're trying to
like bring in both sides, regardless of how much content
there is all that topic topic from whichever side.

Speaker 1 (24:31):
That's interesting because sometimes there's just some issues that are
just you know, I really don't care what the left
has to say about you know, Trump, Packston versus Cornyn,
and I don't care what the right has to say
about AOC versus Jos Shapiro, right, Like, so there are
some issues that you know, it makes more sense to
me that only the rights animated or only the lefts animated.

Speaker 2 (24:52):
Yeah, And what you find on some of these topics,
it's you know, some some topics don't get covered by
the left or covered by the right, And so when
you if you search on that, you're going to find
a ton of content from one side and none on
the other. And so we were just trying to kind
of kind of come back to that just the facts,
ma'am sort of answer. And so we're trying to pull
from both sides, and so it's not and give a

(25:12):
balanced point of view that doesn't say like, oh, well,
everything on this is from the right.

Speaker 1 (25:16):
If you had your druthers, how would you tell news
organizations in the so called legacy media? You know, and
I don't know what that I know, I know what
I think, I know what people mean when they say it.
I know I'm referring to sort of the quote traditional networks,
the longstanding newspapers, right, those things, you know, maybe the
wire services. What would you like to see as a consumer?

(25:42):
Do you want to know about the author, the editor,
the publication, you know, what would give you? And I
just say this because I think ultimately you know that
that I'm sure has informed how you went about this.
So I'm just so like, what would you if you
were in their focus group saying, hey, help us widen
our aperture so that we have people left, right and

(26:05):
center consuming our content.

Speaker 2 (26:07):
Yeah, you know, I don't. I don't know what I
would say specifically too, was just picking like network news, right.
But what we have seen and we've kind of shaped
our product around that, is that fewer people are turning
to network news or even cable news for their information
and more more and more people are turning into podcasts
like your podcast. Uh. And you know, people like the

(26:29):
Joe Rogan's of the world, and you find all these
the Theo Vaughn's, and they're informing themselves through these these
podcasts that have huge followings. And if I was somebody
at a network right now, I'd see that as a
red flag. It's like, Okay, what are we doing that
people trust Joe Rogan more than they trust us. And
I mean I can start off by saying, well, Joe

(26:51):
Rogan's a great interviewer first of all, but it's not
it's less about like his views because he lets people,
he lets people talk, but he's not necessarily news.

Speaker 1 (26:58):
I mean, right, whatever you think of Joe Rogan, he
makes it. You know, the first rule of of of
any sort of content is make it interesting.

Speaker 2 (27:06):
Yeah, and he like I mean, Joe Ruggan is wherever
he's at, he's like, I think he's a good interviewer
because he just asked a question and then he stops talking, right,
and he lets people just go on and on and on,
and then he'll go down rabbit hole. But if I
was like at CBS or Somelace someplace like that today
and say like, hey, you know what, why why are
we losing people to these other these other platforms and

(27:27):
these other forms of media, and like really question, It's like, okay,
so we were holding on to people that are, you know,
in one profile on the spectrum of politics where we
have them, and do we want to expand and make
it more consumable or if you just want to focus
on the people that we have and and kind of
stand in their lane. No.

Speaker 1 (27:48):
I mean, you know, I could tell you where where
I was running into problems was just on length of interviews,
and you know, and that's that was the that was
always the fight. And I used to say, look, you know,
I referred to the Sunday shows as baseball analytics, meaning
there was this point in baseball where everybody had the
same data. Right at first, it was an advantage for

(28:10):
teams that were using data, and eventually everybody's going to
use the same data, and then all of a sudden,
everybody understood how to you know, do the do the
you know, you know, do the do the the switch
whatever when they when they would move all the infielders
to one side or the other, and you know, bring
in the lefty, the left the righty, righty and all
this stuff, and it was becoming almost predictable and you knew.

(28:33):
And was same with Sunday interviews, meaning everybody's knew, oh
it's seven to eight minutes. You know, I can fill
a buster question one and this and this is the
pattern and you know, it's this tyranny of if it
just it was no different than anything else you could
see during the week. And I used to argue, no, no, no,
you got to be you know, this has got to
be the long interview. Don't be afraid of it. And

(28:55):
what are what's podcast treating teaching us? People want thirty
to forty five?

Speaker 2 (28:59):
Yes, well, I mean that's because there's so many of
these issues today that where you know, you and I
could be asked on a question and you're like, well
what do you think of this? It's like, well, my
ten second answer is like I agree with that, and
I don't agree with that.

Speaker 1 (29:10):
I'm going to interact. You've already proven it once. Look
at the trade No, look at the trade conversation we had.
It was not a simple answer, and it isn't right.
It is a complicated answer, and you were giving a
very complicated nuance response, which if you were doing a
five minute segment on one of the cable channels, which
you've done a few times, you know, boy, if I
gave that long answer, then I'm you know, I'm not

(29:32):
going to be able to talk about this, this, and this.

Speaker 2 (29:34):
Yeah, no, one hundred percent, it's one hundred percent. You
get into that. I think you hit right onto. These
sound bites don't allow any of the commentators or any
of the journalists that are part of it to like
really dig deep, to like that second level of information.
It really it is a problem on television and cable
with these short little it's like just ten seconds, like

(29:55):
what's your one little sound bite? And even politics gets
into that too, where it's hard to have a long,
comprehensive answer answer to anything if you have to put
it into ten seconds.

Speaker 1 (30:06):
Well, and then politicians then you get the extra issue,
which is they're they're now afraid to do numances because
they're afraid something's going to get clipped. Yeah, right, exactly,
you get clipped, right, and then that becomes I mean,
trust me, I've been clipped for years now. Like you
said this, I'm like, yeah, but did you hear what
I said? This? And this, which totally changes the context

(30:27):
of that.

Speaker 2 (30:28):
You know, right, everything's taken out of context all the time.

Speaker 1 (30:31):
Right, And it's one thing I've I'm guessing, I don't
want to guess are you making individual deal with the
news organizations because I don't see any Wall Street Journal,
and I'm wondering. Are the paywalls a challenge for this?

Speaker 2 (30:47):
It was are a huge challenge. So luckily a lot
of our users on the places that they like, they
have a subscription already to places like Wall Street Journal,
but we don't. We don't highlight or downgrade anybody's results
based on whether there's a paywall or not. We try
to bring the headlines and the little snippets that we
can grab and give it the best we can, so.

Speaker 1 (31:08):
It is included in your search. So would be there
the Atlantic anybody with a paywall?

Speaker 2 (31:13):
Yeah, all that the paywalls do get included in there.
They just might may not get as highlighted as as
well because we don't have enough information on those particular
articles to give a full.

Speaker 1 (31:28):
I will say the labels on the sports coverage, did
you guys debate whether you needed it or not?

Speaker 2 (31:37):
Yeah? I can't remember. It's been a little while since
we did that.

Speaker 1 (31:40):
I mean, take the Athletic and you note in the
about page because the Athletic is labeled left, and in
the about page you say, look, it's the publisher, and
in this case, the New York Times is the publisher.
I totally understand where you're putting the New York Times.
But you're like the Athletic, I don't know, like I
just don't think of them as you know, yeah maybe
culturally if you none of.

Speaker 2 (32:00):
Them are nice to me, so we should just put
them as wrong at least maybe not nice to our team.

Speaker 1 (32:08):
But that was the one where you're like, huh, okay,
I don't know if I you know sports, you know
there's a handful of places that are trying to put
a political lens in their sports coverage. I hope that
doesn't become a fad.

Speaker 2 (32:23):
That's going to be more like driven by like the
advent of the world, like because we draw from those
guys than gomseelves directly. So they're they're putting that label
on there and it's uh and we're trying to we're
accepting those as you know, as a base just to
have something.

Speaker 1 (32:39):
So let me give you the one Devil's Advocate question
that something like this, because you know, crowdsourcing subjective material
I think is a is a winner. I'm a big
fan of it. I want to know, right, at the
same time, fact, just because something's crowdsource doesn't mean it's true.
So the separation of truth and you look, you made

(33:00):
your you made your mark in the financial world, and
you're making your mark on on actual data and truth. Right,
So what's the what's what's what do you feel as
if free spokes responsibility is on the miss and disinformation
side of things?

Speaker 2 (33:17):
Well, you know, if you go in and you click
on perspectives and any of these topics, right, what it
does is it's finding that that gray area that or
that that overlap between and so often what you find
is that like if it's misinformation, it's coming from one
side and it won't show up on the other side
at all. And so in the perspectives it kind of
you kind of get the overlap of like what both
sides acknowledge as true and a lot of that, a

(33:40):
lot of the other stuff gets kind of it's taken
over to, you know, the left and the right itself
as you as you kind of page down on this
on these searches.

Speaker 1 (33:49):
What's two point oh? I mean, I I have an
idea of what free Spoke two point oh would be,
but I'm curious what what you have planned in your head.

Speaker 2 (33:56):
I'd love to, you know, I'd love to hear your
two point oh. But I think as we go forward,
what we want to do is we want to add
more customization to our premium product and let people really
kind of tell us what they want and shape that
that experience for themselves. So I think that's what we're
going to be working on for the rest of the
year and try to get more and more people into
that product.

Speaker 1 (34:16):
I mean, look, I know I know what I'd be
doing if I were at the hotline using this as
a tool right now, because it would perhaps give me
the opportunity I want to know, what are the what
are the where's their agreement? Show me the agreement between
between left and right and I and then highlight the disagreement. Yeah,
tell me where you know, like, because that is a

(34:37):
consumer right of news and analy analyst. It allows me. Okay,
they believe it's this is the reason, and they believe
it's this is I got it. Okay, and I think,
you know, my guess is that's where you're headed. Right.
Round one is putting all this together, you know. Round
two is getting to all that. And the only fear

(34:59):
I have and what I've envisioning in my head is
do I want a human being doing this or do
I want AI doing this? And I know that it's
easier probably to have AI do it. It might be
ninety five percent good, but then you worry about the
five percent that AI doesn't understand, you know, because it's
just a probability thing, and then it can screw up

(35:19):
the perceptional whole thing.

Speaker 2 (35:20):
Well yeah, yeah, the AI is only as good as
the person who trained it or the people that train it, and.

Speaker 1 (35:24):
So we can garbage out right exactly.

Speaker 2 (35:27):
And so I think I feel pretty good about our
technicians who kind of live this every day, who are
trying to really forget that AI to able to identify
bad information on its own right, and then again kind
of bring that again. I keep saying, like that, just
the facts, just the facts. We're trying to, like, just
put the facts in front of you and let you
read them and make up your own mind as to

(35:49):
what makes sense to you. And I think, yeah, we'll
get better and better in that as time goes on
and as we have more searches and more.

Speaker 1 (35:56):
Do you see a newsletter business for you?

Speaker 2 (35:59):
Maybe maybe they could be.

Speaker 1 (36:02):
What do you think is the next business here and your.

Speaker 2 (36:05):
I was actually going to start my own podcast and
call it the Toodcast. So I think you're going to
be hearing from my attorneys pretty soon.

Speaker 1 (36:22):
And you got better at You probably have better paid
attorneys than I do. You know, Here's what I learned
by calling it the Toddcast. Uh Todd. First of all,
as somebody, you know, when your last name is Todd,
everybody assumes your first name is Todd. I've been third
generation of this. All all the male Todds in my
family ended up just succumbing to their last name being
their first name. But I had I got to take

(36:44):
this with me from NBC because they couldn't. You know,
NBC never lets intellectual property leave, but they couldn't claim
that they could use the Chuck todcast for somebody else.

Speaker 2 (36:56):
Yeah, sound somebody else in Chuck that'd be right.

Speaker 1 (37:00):
So this is the this is the hack. If you
work for somebody else, name a product after yourself, and
at least you have a boxer's chance of keeping your right.

Speaker 2 (37:11):
So you're with, yeah, So, but I don't. I don't
really know if we're going to get into the newsletter business,
but we might. The world is changing and just.

Speaker 1 (37:22):
The basic business ad ad sales and subscriptions the two models.

Speaker 2 (37:27):
Yeah, so we just need to find more people and
more people, more people.

Speaker 1 (37:31):
So of course, all right, before I let you go,
I don't you know, don't get an owner of a
of a sports team, and you probably somebody probably prepped
you in the fact that I was a one of
the founders of Sports Business Journal, So cut my teeth
and cover, you know, create essentially creating the daily sports
business beat, which the industry didn't think it needed until

(37:55):
we created the product and then it then you know,
Sports Business Journal is what it is today. So baseball
in twenty twenty seven. This is one of those difficult
things because from sixty thousand feet. The answer seem obvious,
the details are very difficult. If there's a sal can

(38:16):
you sell a salary cap without complete equal revenue sharing
among the owners?

Speaker 2 (38:23):
Yeah. I think the answer is the short answers yes,
the network news answer is yes, and a little bit
more detailed answer is. All the other leagues have kind
of gone through this, right, They've all had that growing
pain of getting into having a hard tap and having
a hard floor to make sure that the league stays competitive.

(38:43):
I think what you'll see in baseball is we'll have
sort of a revenue sharing model that might have to
do with TV rights, like taking more TV up to
the league and splitting that and making sure that every
team has enough to breach the floor. And if you
think of that, it just like taking one hundred million
dollars the pain roll away from the Dodgers and taking
it to the Pirates and making sure the Pirates have

(39:04):
enough money to cover it.

Speaker 1 (39:05):
And you, as the owner of the Chicago Cubs, who
frankly have more opportunity for revenue than the Minnesota Twins
or the Pittsburgh Pirates, you're going to be okay with sharing.
You know that you're basically contributing more to the pot
than the Pittsburgh Pirates in the Minnesota Twins.

Speaker 2 (39:23):
I I I, yeah, No, I'm comfortable with that. Like,
if the league doesn't have competitiveness, we're going to start losing.
And so we need to have a competitiveness across the board.
Although I will say in baseball doesn't spending money doesn't
always turn into results. The Dodgers beauty of the.

Speaker 1 (39:39):
Best three and five, Please don't ever get rid of it,
because it's the great equalizer, right the Dodgers. You know,
trust me as a Nats fan, and you know, if
you get the Dodgers in a five game series, you
got a chance you can't beat on a seven.

Speaker 2 (39:54):
Well, you know, and if you just look what's happened
at the Cubs this last week. I look at some
of the teams we played, I'm like, there's no one
guy in that other dugout that's good enough to be
on this team, and they just beat us. So it's
like you kind of you have to roll with it.
But we do need to find like that that balance
and get into this thing, this this era where you know,
it's good, it's good for the league. If all the

(40:15):
teams are profitable at some level and not losing money,
and we have a little bit of competitiveness on the field.
I think that's good to be good for baseball. And
you know, some of the modeling that we've worked out
internally is that you know, right now, players get about
forty eight percent of revenues in Major League Baseball. And
then and the model we're going to present that. You know,
I'm not I'm not part of the Major League Basketball,

(40:38):
but you're going to be. Are you on any of
these committees where you'll be sitting down now? In fact,
my brother is our owner representative, so he's he's much
closer to the league and talks to the connatural lot.
But but my instinct says that, like we're going to
go from someplace where it's forty eight percent of the
revenues today to like fifty two percent of the revenues
in the future baseball, Right, Yeah, that's right. I like that.
I think you and I think the NFL about there

(41:00):
in the NHL, I think they are all just above
fifty percent. So what you'll see is like it's actually
more money to players, just in a different form than
the giant free agent contracts with hundreds of millions.

Speaker 1 (41:12):
No, I mean this is look, I mean, I know
we're going to hear it's, you know, the Scott Boris
view of the world, right, you know, basically unlimited free market.
Great if that's the way it worked. But you know,
let me ask you this as a as an owner,
and for me, I'm going to call you relatively new.
I say relatively new, right if you if you've only

(41:33):
been an owner for about ten or fifteen years compared
to seventeen yeah, right, compared we have some people that
have been owners for you know, generations rmuch longer for sure,
and you were in the particularly in the finance world.
What's the what's the same about operating a sports franchise
and what is different as a you know, everybody says, well,

(41:55):
you got to operate it like a business now, but
a sports franchise, boy, it's complicated. Because you know, we
were discussing this before we started. Your fan base thinks
they own the team and unlike and only the Green
Bay Packers have a fan base that actually can say
they own a piece of the team. Although I'm sure
if you guys started selling shares you do pretty well.

(42:18):
So what's the same and what's the big difference.

Speaker 2 (42:22):
I think a lot of the same is just trying
to run you say, run it like a business. It's like,
how what are we doing on ticket sales? Are we
selling every ticket that we can? Are the tickets price right?
Where are we with our corporate sponsors and how they
can contribute to the team in ways that we can't
go with other places for So it is very much

(42:44):
a business. And on the other side, you have these
opportunities to be completely irresponsible sometimes where you're like.

Speaker 3 (42:51):
Okay, we're just one game out and if we win
our division, it's going to mean this, and so do
we go out and and and get that extra free
agent or or or or kind of get outside our
own discipline. So you always have those opportunities, And I
got to say, like, I don't think it's the craziest idea.
Sometimes it's just it doesn't always work out and then
you generally regret it.

Speaker 2 (43:12):
But we we keep it pretty tight ship. We have.
We really have a great team of people. There were
a lot of great people that were at the Cubs
when we bought the team, and we've supplemented that with
a bunch more and it's it's a very disciplined business.
And when we look at those opportunities to step outside

(43:32):
our disciplines and like the discipline, especially when it comes
to the baseball team itself, we think long and hard
about it.

Speaker 1 (43:39):
What didn't you know that you were like, oh my god,
I wish i'd known this.

Speaker 2 (43:46):
It's been a little while since since we bought the team,
and it kind of went through it. It's what you
don't see is the backside business side of all the teams,
and and you look at other teams and you see
how their run and you're like, gosh, I really I
wish I could give them some advice. I wish not
every team in every league is run with the same

(44:07):
sort of professionalism that we have. And that's why you
kind of see some of the variations of teams that
can make money or lose money and so on and
so forth.

Speaker 1 (44:16):
So I'm doing this sports history podcast with Jayadande, and
we've done three deep dives so far, the Dodgers, the Steelers,
and the Warriors. And you know what all three have
in common is that their original owner was essentially the
local sports promoter. So like Art Rooney for the Steelers,

(44:36):
he was the guy that the NFL went to, hey,
do you want this franchise? Because he was the guy
you went to if you were bringing a boxing match
to Pittsburgh and you wanted to promote it, and he
was that guy. And the Warriors owner the first one
in San Francisco was sort of it was like a
nightclub owner. You know when I say that, he didn't
own a night club, but it was the equivalent of
where you were just can I bring in a marquee

(44:57):
name to bring in fannies in the seats so I
can sell a few extra concessions, like how much you know,
we've seen this transition from sort of the family business model,
right the small business owner model, to the twenty first
century business you know, acumen, Harvard Business School type of

(45:18):
mindsets and take baseball. Would you say eighty percent of
the teams are in this bucket now? Or you know
how many of the teams are still in the mom
and pops phase of operations?

Speaker 2 (45:29):
Maybe you know, maybe half and half. I'd have to
like go through team by team and see where they're apposite.
It's definitely has a few things have changed in the
last twenty five years that have changed the way the
businesses are run. First of all, you've seen institutional money
kind of coming into some of these teams, you know,
these big of these big guy.

Speaker 1 (45:45):
Do you have any private equity? Do you guys have
brought any in? Have you guys brought private equity in
or not?

Speaker 2 (45:50):
We have like a wide range of limited partners that
we brought out at different times, Like we sold off
some of the team to renovate Wrigley Field, so that
a lot of that that was all privately funded, and
we did that through selling a little bit of equity.
But what's happened is like these as you bring in
that institutional money, they want to bring in that professional management.

(46:10):
And the second thing that you're saying is that as
teams need new stadiums, the city, county, state governments are
less and less inclined to finance those. And so that
I don't think that's a problem. But what it does
is it changed the mindsets of the team. Whether they
start saying like, Okay, well, if we're going to fund
our own stadium, we're going to want to own some
real estate around our stadium. We're going to want to

(46:32):
own all of our parking lots, We're going to want
to control that fan experience from a perimeter that's not
just the venue itself. And so that's why you're seeing
these kind of entertainment districts. And you know, we kind
of we built one around Wrigley that's been really successful,
and others you're doing that.

Speaker 1 (46:48):
You tell me, I don't feel like Wrigleyville was a
thing until you guys kind of made it a thing.

Speaker 2 (46:54):
You know, we really had that mindset of wanting to
control the neighborhood and control that fan experience for the better. Really,
you know, we're just we want to make sure our
fans are having a great experience when they come to
the ballpark. And I don't and I don't know what's
changed about sports specifically to make it like this, but
it's no longer just about the two and a half
hour game or that. You know, even for football, you know,

(47:15):
the football you have tail getting before the game, and
and for baseball you were starting to see it's like
people come down early to get something to eat, and
then they go to the game and then they're going
to go out maybe to a show. We're just go
to the bar and to have a few beers. Like
it's an all day experience. Regardless of how long the
game itself is, and so people are trying to like
make sure that that experience is positive for everybody.

Speaker 1 (47:39):
Should baseball games be available for free? In Chicago? The
Chicago Cubs always be available on supposed free TV, and
should that be a philosophy of Major League Baseball?

Speaker 2 (47:49):
I'm going to I'm going to shift a little bit
and say all team owners want their fans to be
able to see their games on TV. But the world
is such upheaval day, whether it's you know, the cutting
of the court on cable has happened so quickly and
so much shifted to these strips services that I think

(48:10):
that it's not just baseball, it's football. Is everybody's kind
of in the space of like, Okay, we were trying
to get our games out to be seen, but we're
also still trying to get paid for the games in
the old way that we were when we just went
to Comcast and they just gave it. You know, they
gave you a button.

Speaker 1 (48:27):
Hey, we'll sell the ads. Well, we'll make it on
the back end. And I'm guessing media networks like, no,
maybe you guys can sell the ads well.

Speaker 2 (48:36):
And the funny part is is that everybody was paying.
Everybody thought they were getting Cubs games for free when
they had their cable, but they weren't. They were paying
for it in their cable bill, and always just included.

Speaker 1 (48:47):
Yeah Apple companies for years just passed along and you
didn't realize. And then when you disaggregate that bundle, you're like, well,
somebody's got to pay for this. You know, it was
always I joke. You know, I've made a lot of
money over the years on OPM, other people's money, right,
whether it's newsletters that were so expensive that it became
a business expense, so there was no individual that you

(49:09):
went to for a subscription. And you know this, a
B to B business is sometimes more stable than a
consumer facing business.

Speaker 2 (49:17):
Yeah, that's right. And I think what people are finding
out is they were paying more for their sports than
they thought. You know, if your if your cable bill
was one hundred and fifty dollars, I'm just making it
a number, and you're like, well, I bet I've been
in paying like two or three of that goes to sports,
and you're finding out, well, actually it was like twenty five.
And now if you want to get those same games,
you're gonna have to pay twenty five dollars a month

(49:37):
to have that, and so it's all it's all just
in flux, and I know that there's the bigger brains
in mind are thinking about it, and all sorts of
people outside in sports are concerned about it. But at
the end of the day, I think, you know, we're
just we're just trying to find out where people want to.

Speaker 1 (49:52):
Have one dumb request. I'm a season ticket holder. Why
do I also have to spend extra money to watch
the games at home?

Speaker 2 (50:00):
Yeah, that's a good point.

Speaker 1 (50:01):
You get here that because I always you know, it's
interesting what season ticket holders have always gotten at the
MLB Extra Innings package. Yeah, like that's always come with
the deal. But look, some of this was new, right.
The Nets were part of the of the group of
teams that all had to scramble to put together a
deal before the season started. So it's possible they'll stick

(50:24):
these things through. Well, let me let me close with this.
What's this If you don't win a division, If you
don't win the division this year is the season of failure?
If you don't get in the playoffs, is it a failure?
What's your what's your the goal is always win the
World Series. So I'm going it's but what's what's your
realistic what's a disappointment to you this year? Because baseball is.

Speaker 2 (50:45):
Hard, you know, we kind of you're going back to
that baseball discipline and business discipline. We shoot to be
in the playoffs every single year, so if we're not
in the playoffs, that's one season to us. Yeah. And
when I look at our roster and I look down
the talent that we have, I feel like we have
an incredibly competitive team. Now we don't have a Dodgers
as far as like the payroll numbers, but when I

(51:07):
look at like the talent we have top to bottom.
If we can, if we can get some of these
injured guys back on and get everybody playing, get you
every ready to aggress back to their norm right, Uh,
they're there, have an average season. I think we have
an incredibly competitive team, which is kind of your sky's limit.

Speaker 1 (51:24):
Have you like bugged your guys going why didn't we
sign Murakami?

Speaker 2 (51:27):
But never mind? You know, no, No, I feel like
as as an owner, you have to like turn that
over to the baseball guys. And because if you get
too involved, you can't hold them accountable, right, Like if
you if you tell them who to get who we've.

Speaker 1 (51:42):
Seen other we've seen other owners, and they get really involved.
And then if it doesn't go well, especially at the
say started the first third of the season, then you
only have one person to play.

Speaker 2 (51:54):
Right, That's exactly it. So I never want to be
the person that gets blamed. So I throw out ideas,
but I don't I don't like live and die by them.

Speaker 1 (52:03):
Well, pre spoke, this is how much of your bandwidth
is on this?

Speaker 2 (52:10):
Yeah, well a lot, I'd say a lot of it
at the moment, I'm sure until Yeah, like i'd say
like half of my time spent on free spoke for that.
At the moment, we're trying to get our product in
a way and place that we like and find new users.

Speaker 1 (52:24):
Well, I hope you know, just keep reaching down to it.
There's a lot of great, sort of what I call
entrepreneurial local news sites that are really trying to fill
the gap, and that to me is you know, the
information ecosystem. What you're trying to do is something I
think we need. And there's a lot of decent bottom
up journalism. They just need a little awareness because Google

(52:46):
makes it hard. Google and Facebook made it at first
made it easy to be a local publisher, that made
it quite difficult. And if you could be in place
to help local because that's been the biggest thing that
is killed local publishers is how good rule is messed
with search and awareness. And this feels like an opportunity
for local news to get to get some you know,

(53:07):
to have a site that won't hide there or that
will only boost you. I mean, it feels like you
have to pay Google to get boosted. I'm not saying
that is how the business works, and I know they
would claim it isn't, but that's the way many of
these local news entrepreneurs. Yeah, that's the way they feel
like it works.

Speaker 2 (53:23):
Yeah, no, it totally. It totally is how it works.
And so we're we're trying to combat that and and
really just informed people. So if you have if you
have sources that and that we're not crawling. You're not
saying to show up and free spokes, let us know
and make sure we get it added to our index.

Speaker 1 (53:39):
Well, like I said, I love what the all sides
guys do. And uh and I know him pretty well
and he works really hard on that on that bias
rating system, and I know the advont stuff too. I
mean it's it's good metrics to you. So Todd Ricketts,
this was a pleasure to get to know you. And uh,
like I said, I love what you're trying to do

(54:00):
and I encourage people to check it out.

Speaker 2 (54:02):
Great. Yeah, thanks for having mem m h m hm
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