There’s no one more perfectly situated between the tech media and the tech elites who loathe them.
Jason Calacanis built his reputation in Silicon Valley as a feisty tech reporter, waiting in line to ask Steve Jobs questions at the Code Conference. An extremely early investment in Uber suddenly made him one of the most famous angel investors in the world (thanks also to Calacanis’s self-promotional megaphone). Today, Calacanis co-hosts All-In, the second-most popular tech podcast and one of the most popular podcasts in the world. The show is a must-listen in Silicon Valley and the envy of many wannabe thought leaders.
We invited Calacanis on our much, much smaller tech podcast Dead Cat to interrogate what has made All-In so successful and where Silicon Valley’s roiling war with the media is headed. Calacanis, who is reportedly part of Elon Musk’s war room at Twitter, warned us that he absolutely would not talk about Musk’s Twitter. (We tried.)
This was a fun episode that we recorded right before Thanksgiving with co-host Tom Dotan and regular special guest Katie Benner. I’m going to publish a companion article with my reflections on the conversation shortly. Enjoy!
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00:00:05
Welcome, welcome. Everybody Hugh dead cat episode.
00:00:16
We are extremely excited about. We have Jason calacanis, the all
00:00:22
in Host this week in startups, angel investor famous for
00:00:25
investing Uber. I've been ahead of this episode
00:00:29
Katie and and I went on Jason show this week in startups in
00:00:33
2016, and that was like, you were Jason, you're an extremely
00:00:38
early supporter of me, as a, as a young Tech reporter and Cub
00:00:43
reporter at the information. And Bloomberg, I remember
00:00:46
exactly. And in the, the episode with
00:00:49
Katie and I were sort of, you know, discussing Facebook's
00:00:52
content moderation. So it's amazing are toxic to
00:00:55
just like how much some of the like same themes, keep coming
00:00:59
up, but You so much for coming on the show.
00:01:01
Thanks for having me. Yeah, I mean, there's so much to
00:01:05
talk about. How do you is there anything in
00:01:07
the news? Because they're Bob Iger.
00:01:10
Yeah, that's very big low this week, FTX their own house.
00:01:17
I mean, how do you spell your time these days?
00:01:20
I think that that's yeah, this is a starting point.
00:01:23
So I Angel invest in people don't really actually understand
00:01:27
the pace at which the investment is going right now.
00:01:29
I put about 60 million to work a year in about 75 to 100
00:01:34
Investments. I have 22 people on the
00:01:36
podcasting and investment team that's launched this week in
00:01:39
startups all in. So it's a pretty at scale seed
00:01:43
fund, but I must what's called a solo GP.
00:01:46
And, you know, we've invested in 350 companies to date.
00:01:51
And we have the largest Syndicate in the world.
00:01:53
It's like an Angel, Investing Syndicate, called The
00:01:54
Syndicate.com, it's 11 members.
00:01:57
So when I invest in a company, Maybe about half the time the
00:02:00
founder wants additional investment.
00:02:02
So we will syndicated and then I do podcasting in the mornings
00:02:05
with Molly would for this week in startups.
00:02:08
And then I have still have the company inside.com a newsletter
00:02:12
and social new site that I've been working on Dust a couple of
00:02:15
million a year in revenue and so that gives me like a little
00:02:19
media itch to scratch. And yeah, then once in a while,
00:02:22
I work on some special projects and all in.
00:02:25
It's the 21st most popular podcast.
00:02:29
It was 14 this week 14 last week, I was looking at, you
00:02:33
know, one of the list just now an apple, but I'm sure there are
00:02:35
50 different kind of crazy shit to be honest.
00:02:37
Like, I mean, you're being recognized on the street at this
00:02:39
point now, right? I mean, I mean, if I was in a
00:02:42
text City people might recognize me, you know, like I'm in Austin
00:02:46
or new. Your would have been, it would
00:02:47
have any way, right? Because of this, we can start if
00:02:49
anybody like once. Now the thing about all in is
00:02:53
the tech industry is not that popular.
00:02:54
So we wouldn't get to that level without having some other
00:02:57
constituents so Finance. Colleges, like I was skiing with
00:03:01
my daughters and I asked somebody if they were done with
00:03:03
their table and she was like, oh my God, Jake I was like, oh I'm
00:03:06
sorry do we know each other? And you know she said no, I'm a
00:03:08
dentist. I said oh, you know, she's like
00:03:11
I listened to your pot every weekend twice.
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I'm like, why do you listen to her twice and decide?
00:03:15
You know, I'm trying to learn and kind of replaced like Meet
00:03:18
the Press. For me, it's like my Sunday
00:03:19
Morning Show which paradoxically is kind of how I impart.
00:03:23
What I based the forming on what were?
00:03:25
Well, that's interesting. I thought you were going to say
00:03:27
Jason that I'm a dentist and we play all.
00:03:29
During you know, over the speakers at a dentist's office
00:03:32
on your teeth and you'd forgotten.
00:03:34
Yeah. Well people getting a feeling
00:03:35
they're like is that Shema exactly?
00:03:38
It has crossed over in a way that is completely bizarre
00:03:43
college kids. Big time like a lot of them
00:03:45
listen to it and it's saturated makes sense to me that makes
00:03:47
most colleges. A lot of colleges have Venture
00:03:51
Capital clubs now and Venture investing clubs so it makes
00:03:54
total sense. Yeah I mean and people want to
00:03:57
hear us talk about things we're not Experts on like politics and
00:04:01
covid and other topics. Which is that's why people
00:04:03
listen to us. Actually, to hear us talk about.
00:04:05
It's a little weird though. Like, people are like, how dare
00:04:11
you talk about covid and I'm like, aren't you talking about
00:04:13
cover? We're friends and they're like,
00:04:14
yeah. But I don't have a top 100
00:04:16
podcast that I'm like, well, you can also listen to the Pod and
00:04:19
then realize we're not experts and then go do your own research
00:04:22
and elect know your experts. Only I just told you we're not
00:04:25
experts and you told me you'd understand we're not experts.
00:04:28
So why is it so so tweaking that you know non experts are having
00:04:33
a conversation about a random topic.
00:04:34
So this is like sort of but this leads to a tech question that I
00:04:38
think you're equipped well equipped to address which is how
00:04:41
technology has really broken down the barrier between experts
00:04:46
and non-experts, right? Because everybody has equal
00:04:49
access to a public platform or near equal access to a public
00:04:53
platform. So what do you think?
00:04:55
You know, walk me through how you see that sort of as the Cons
00:05:00
of that destruction of the barrier between expertise and
00:05:03
non-expert. Yeah you know we probably all
00:05:07
lived in a bit of a bubble where we just thought, well we can
00:05:12
trust anybody who's an expert, right?
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I just trust my doctor and they're going to give you the
00:05:17
right information. And then people learned over
00:05:18
time like well, maybe my doctor doesn't have all the answers.
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Maybe there are some alternative medicine, or maybe yoga practice
00:05:24
would help me with my back pain. Maybe, I don't need to just do
00:05:26
drugs and, you know, take Vicodin or something.
00:05:29
Right. So people I think over the last
00:05:32
couple of decades probably like you're saying Katie because of
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the internet have had access to the same information as their
00:05:37
doctor. So you're sitting in your doctor
00:05:38
or doctors office, doctor says oh you should take Vicodin for
00:05:41
your back pain and you look it up and you find an article that
00:05:43
said oh this is addictive so well isn't it addictive and
00:05:46
doctors like yeah but I don't have anything else for you and
00:05:47
then somebody else says oh you know I did Hot Yoga it, healed
00:05:50
my back or I lost 10 pounds so I think we've started to maybe get
00:05:55
back to where we should have always been, which is the search
00:05:59
for Is Elusive. And you should take a
00:06:03
multi-pronged approach to figuring out what the truth is
00:06:05
and what the truth is for you. So your truth might be different
00:06:08
than mine and I'm not a conspiracy theorist here but you
00:06:12
know sometimes yesterday's conspiracy theories are
00:06:15
tomorrow's Pulitzer prizes, right?
00:06:16
We've all seen this happen. Let's an example of that.
00:06:19
You think about like their nose or something.
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Yeah, I mean, listen, we all have been journalists for a long
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time and we put their nose on the cover of magazines hiding
00:06:27
but I'm sure all the public a shindig Workforce and Harmony
00:06:31
New York Times. Yeah, I'm sure has put them put
00:06:34
her on the cover. Yeah.
00:06:35
With Marc Andreessen, didn't mark Anderson's wife.
00:06:41
Right? Isn't cases what you rip it at
00:06:43
every flame but Marc Andreessen wrote it.
00:06:47
But yes we did. We did publish it.
00:06:49
We did. I was gonna let that happen
00:06:51
ownership. All right?
00:06:52
Yeah sure. So anyway so there are no such
00:06:53
as one I think actually with covid.
00:06:56
I don't know if you read pro-public has peace with Van.
00:06:59
Fair on the Wuhan lab, the lab theories.
00:07:03
Right. You were to kick it off.
00:07:06
Yeah, you would have been kicked off of social media or your
00:07:09
podcast would be labeled. And you be kicked off Spotify if
00:07:12
you even acknowledge that 18 months ago, and propublica is
00:07:15
going to win, you know, journalism awards for it.
00:07:18
If it turns out to be true and maybe it's not maybe the ccp's
00:07:21
denying it now. So here we go.
00:07:23
Our job as journalists. Wait.
00:07:25
Yeah. So, you know, when I was a
00:07:27
journalist and I started in the 90s One of the first journalists
00:07:30
I met at the New York Times was a cub reporter named Jason
00:07:33
Blair, and he called me on the phone, he said, oh, you have
00:07:35
silicon our reporter. I'm good.
00:07:36
At my new bead is silicon alley. Can we meet?
00:07:38
I met with them and I was like, this guy's a dope like really is
00:07:42
dumb. I was just struck by how stupid
00:07:44
he was and he's like, let me know whatever information you
00:07:48
have. So I could write a story and
00:07:49
I'll get you good press and I'm like sorry.
00:07:52
You know, I went to some of the other New York Jets All Hands
00:07:53
lost like who is this person? Like and you know, kind of eye
00:07:57
rolls or whatever and everybody makes That whole Scandal led to
00:08:01
the downfall of the then editor of the New York Times.
00:08:03
It was actually quite a quite a messy.
00:08:05
Devastating episodes have been history Champion.
00:08:08
Yes, but your point Jason is that you could kind of tell
00:08:11
early on meeting this guy that something was amiss with him and
00:08:13
he seemed even for a journalist fairly dumb.
00:08:15
If yeah, I just didn't seem like the level of a New York Times
00:08:19
journalist. And I was listen, I had started
00:08:20
my own publication, I wasn't getting published by the New
00:08:22
York Times. I just was a hack who started a
00:08:25
newsletter called silicon alley reporter which became a 300-page
00:08:28
color glossy. But you know I was looking at it
00:08:31
and we were really trained hard to like take our time.
00:08:35
Make sure we had three sources, you know, we didn't back in
00:08:39
those days. You didn't want to have
00:08:40
off-the-record sources, that wasn't kind of a loud if you
00:08:43
inserted any kind of opinion you would get admonished.
00:08:47
And, you know, you had time to file and probably, I don't know,
00:08:52
one out of three stories was killed because it wasn't good
00:08:54
enough. So now you fast forward because
00:08:56
of blogging, which I was part of and the Ace in the competition
00:09:00
and the buzzfeed's of the world and Business Insider's of the
00:09:03
world, the pace and the filing in, which people have to do
00:09:06
stuff in the lack of fact. Checking, I'm talking about like
00:09:09
a dedicated fact, check my apartment.
00:09:11
All of that is gone with the exception of a small number of
00:09:14
Publications and so there's going to be more mistakes.
00:09:17
People are filing faster people doing this process journalism
00:09:19
thing which is really lame and they're relying on unnamed
00:09:22
sources. So well, I think there's a lot
00:09:24
of immediately into that, you know, like walk us through the
00:09:27
role that social media has played There.
00:09:29
Yeah, what do you think is played into it?
00:09:32
Okay I mean I don't know I mean because you had mentioned social
00:09:34
media and you mentioned Business Insider and so do you think that
00:09:37
those are the culprits The culprits of what of this sort of
00:09:43
like sped up journalism cycle. This is definitely our
00:09:46
competition, right? People are forced to file faster
00:09:49
and you're competing because it's everything's instantly
00:09:52
published. It's not like you can wait for
00:09:54
the next day in print. So yeah.
00:09:56
I mean, the pace has increased the resources have diminished,
00:10:00
so it's, there's going to be. We learn when stuff is wrong,
00:10:03
much faster. Like, it's harder to imagine
00:10:06
sort of a Stephen glass Jayson. Blair sustaining for, as long.
00:10:10
The other side of this, if you're on the other side of it
00:10:13
and your subjects of, you know, the Press today having been on
00:10:17
both sides, you become acutely aware of the mistakes and the
00:10:22
mistakes hit the subjects Harder Faster.
00:10:24
And so, you know, you look at the New York Times away piece,
00:10:27
you know, they demolish that founder felt very biased to me.
00:10:32
And so, you know, I think that's where the standoff is happening
00:10:34
between the tech industry and certain industries.
00:10:36
And the Press is, there's so much think there's a lack of,
00:10:40
right? Well, first of all, where is
00:10:42
your Allegiance on you? In our, in our decision 2016 and
00:10:48
they're going to have their own truth.
00:10:49
I don't know how that's amazing but like do you see yourself as
00:10:52
a journalist? I mean you talked about doing
00:10:53
random acts of Journalism back in 2016.
00:10:55
Obviously, at one point you really saw yourself as a
00:10:58
journalist. Wow, was a journalist at
00:11:00
Ryerson, had a bunch of riders, ready for me.
00:11:01
Now I would say most people would say I'm a commentator but
00:11:04
yeah probably an informed one. I mean and I think that's what's
00:11:07
happened is you're having because of this contentiousness
00:11:10
Back and forth and you ask my allegiance mileage insists only
00:11:13
to the truth and fairness and kindness.
00:11:15
To be honest, I always know. I mean, I'm dead serious about
00:11:18
that. Like what if I make a mistake
00:11:20
when I'm doing commentary on the subject?
00:11:22
I think deeply about like oh what did I get wrong here?
00:11:26
And I try to make up for it, right?
00:11:27
Absolutely. Whenever something comes up like
00:11:30
Sam Bank been freed now, I'm like alleged alleged.
00:11:34
Let's make sure he's in the word, alleged on the Pod and
00:11:38
trying to, you know, just give a slight benefit of the doubt.
00:11:40
Out until the information was at not sure who is watching all in.
00:11:43
I mean you guys use data from like an anonymous source that
00:11:47
Sachs had on some company's performance.
00:11:49
I'm trying to remember what the common animus or is or do we
00:11:54
have inside information by? Yeah right you guys get to frame
00:11:57
it is inside information. Well, I mean if you're on the
00:12:00
board emanating from know but you guys can't like disclose I
00:12:05
don't think it was a first hand on the I think what you're
00:12:08
getting at here is if you guys what's up.
00:12:11
Happen in the standoff, right? So you have this standoff,
00:12:14
that's occurred. There's equal, there's a both
00:12:18
sides could do better, right? And I would say that the tech
00:12:21
press is far too - and now they put the tech leaders who, you
00:12:26
know. Listen, we have much more
00:12:27
influence now in Tech than we ever did.
00:12:28
It's impacting everything, but I'm not saying, tech companies.
00:12:31
Don't make mistakes far from it. Trust me, I'm an investor in
00:12:33
these companies. Have to do some of the cleanup
00:12:34
work, but now it's happening. People going direct because
00:12:37
they're like, well, we can go direct right.
00:12:39
We don't need the Press. So people ask us to do, you know
00:12:42
many folks have asked us to profile all in and the boys just
00:12:46
decided. No we'll just keep working on
00:12:49
the podcast every week and we're bigger than any, the total I've
00:12:53
Tec public. The top 5 Tech progress isn't as
00:12:56
big as all end now. So why would we even need to?
00:12:59
I'm only coming on this bike is because I'm friends with you
00:13:01
giggling. Yeah, well no, I mean, you came
00:13:04
on my podcast I'm you know I'm right and obviously every should
00:13:07
Tom and Katie's careers because you're fun and interesting.
00:13:10
Because you're like this is going to get me something.
00:13:12
No it's not going to get me anything yet, right?
00:13:14
So it's more like it's a fun conversation.
00:13:16
Absolutely. Yeah.
00:13:17
So I think that's what's going to be the trend Tom since I see
00:13:20
you trying to get in here on the discussion and Eric just having
00:13:22
a hard time. Moderating Tom, I see you want
00:13:24
to jump in and I'll just take this and it's not like you're
00:13:27
the world's best moderator because even when you're not the
00:13:29
moderate, exactly already tips. But I think Tom, what do you
00:13:32
think about sources going direct now?
00:13:35
Well, any sources, just assigning, I'll just go direct
00:13:37
our route around and I won't talk to the Press.
00:13:39
Well, you know, I guess this gets into the definition of what
00:13:42
the Press is and I think you actually sit in a very
00:13:45
interesting place because you have a journalistic background,
00:13:48
right? You've spent a lot about your
00:13:49
career building journalistic institutions that adhere to what
00:13:53
many people would consider standard journalistic practices.
00:13:56
So you're a conveyor of well-sourced Truth as your
00:14:00
reporters and you've tried to do it.
00:14:02
And what I find. So interesting about all in
00:14:04
which I listen to fairly regularly, and I do think it's a
00:14:06
really entertaining podcast. Is that you and specifically
00:14:09
David Sachs. I do spend a lot of your time
00:14:12
talking about this transition away from Legacy Media to going
00:14:15
direct and you've refused to you know participate in any of the
00:14:19
profiles written about you because you see no upside to it.
00:14:22
You sort of see it may be partly as they're being antagonistic to
00:14:25
you. Yeah.
00:14:26
It'll be a hit piece, it rises, right?
00:14:28
It's going to be a hit piece. You're like, why participate in
00:14:30
it? They'll write it anyway.
00:14:31
Why should we even bother talking after reporter over it?
00:14:34
And yet, it seems to me and correct me if I'm wrong here.
00:14:36
That you guys spend a lot of your time or believe, you know,
00:14:40
very strong. We that we as reporters are out
00:14:42
to get the tech companies that we want to take these companies
00:14:45
down because at least in the case of, you know, you're being
00:14:48
a Direct Media Company. It's a competitor to us that we
00:14:52
view you as a threat. And so it's in our best interest
00:14:54
to sort of position you as a bad thing because that I don't know
00:14:58
helps our business model or helps actually not the reason.
00:15:01
Okay, explain explain to me the reason.
00:15:03
No. I mean we make zero dollars from
00:15:05
all in famously, there's no ads. Right?
00:15:07
So it's not like we look at it as we're competing against the
00:15:10
Yes, I think the Press has been so unfair for so long that
00:15:15
there's a level of frustration in dealing with them in the tech
00:15:17
industry. And so most people intact, they
00:15:19
would say publicly are just like why bother if the Press is
00:15:23
contacting you it's a negative story and if you were to go
00:15:26
through the New York Times and just pull up the last twenty
00:15:28
stories and there's been some back-channel of like a the New
00:15:30
York Times decided to go - x number of years ago on Tack and
00:15:35
whole truth to power. But you know, this whole we
00:15:38
experience from our side with our portfolio companies, So, if
00:15:41
the Press calls, what people say is, do not respond, it's going
00:15:45
to be negative and just write your own blog post.
00:15:48
Do your own blog, get the message out directly.
00:15:51
The Press is only trying to do something - to get clicks.
00:15:55
We you you like that's the dialogue here in science or
00:15:58
Valley right now. Is there a recognition though?
00:16:00
That the Press isn't just finding these things, that is
00:16:02
actually employees within the companies who are calling us
00:16:05
with the information. Like, when I mean, I understand
00:16:08
what you're saying here. So what is there a second part
00:16:10
of the Shannon. That's like don't comment, don't
00:16:13
work with them. At the same time.
00:16:15
You might want to try to figure out what's happening inside your
00:16:18
culture because you pay these people.
00:16:19
A lot of money. They get a lot of perks and yet
00:16:22
they're still doing the nuclear option of reaching out to
00:16:25
somebody. They've never spoken with, it's
00:16:26
not like the people who are calling me were my best friends
00:16:28
and never any of them. They're not so reaching out to
00:16:31
people who they've literally never met before to go to them
00:16:35
with this information. So you might also want to get
00:16:36
your house in order. There might be an actual
00:16:38
legitimate problem course. Yeah, I know.
00:16:40
Is it just like the Press is? So mean and median because we're
00:16:43
these genius reporters all the time.
00:16:45
People are coming to us. Of course, that's it.
00:16:48
Each situation is different. There could be people leaking
00:16:50
information because there's something horrible that's
00:16:53
occurred like their nose, right? And so, in that case, it's just
00:16:56
excetera. And then there are cases where
00:16:58
like with the New York Times profile of away, I'm not an
00:17:00
investor, I don't know. The founder where they're like,
00:17:03
oh, the founder told everybody in slack work hard because this
00:17:07
is our busiest season and the New York Times makes this Bash.
00:17:10
Inge story about the oh, a Founder, you know?
00:17:13
That she gave like a Esprit de Corp, speech, like work harder
00:17:17
everybody. This is it.
00:17:18
And then a bunch of you know, snowflake employees complain
00:17:21
about. How do you say?
00:17:22
But if you're on time like that, it was an example of employees.
00:17:26
Coming to the times, I don't think away was a company, it
00:17:29
doesn't matter if there is enough to your time on the radar
00:17:33
of the time. So it's like, if that is the
00:17:35
case, that the employees are feeling that way, it in addition
00:17:39
to being, you can be mad at the time.
00:17:40
And but how is it the most important?
00:17:42
How is that the important story? And, and I think I'm were some
00:17:44
good things. I'm saying, like in when you're
00:17:46
having these internal conversations, you can say,
00:17:48
like, the times might be being unreasonable on this story at
00:17:52
the same time. What is going on that more than
00:17:54
one multiple employees would be? So pissed at what you're saying
00:17:58
is no completely harmless speech?
00:17:59
That they would even take that step?
00:18:01
It's not like those employees, knew the reporter Katie our
00:18:05
employees today, more entitled than they were 20 years ago.
00:18:08
Yes, or no. Well that I don't know.
00:18:10
It's On the industry is tourism, that's what people who work at
00:18:21
Starbucks. I would say, you know, people
00:18:22
who work in the industry is that, like, people at Starbucks
00:18:25
are no more entitled play. Don't think you've been to a
00:18:27
Starbucks, but you know what I mean?
00:18:29
Like, I think that if you, if you're looking realistically at
00:18:32
work, I don't think you can say that all employees, are more
00:18:35
entitled. And I don't think you can say
00:18:37
all, I'm sorry, I all up. I'd say all Americans are
00:18:40
entitled. About that, but put it aside.
00:18:42
Don't here's what they say that. There's a huge gap and I think
00:18:45
there are a lot of people who don't have a lot of money or
00:18:46
opportunity, and I've never had lower unemployment is at an
00:18:50
all-time low, but that there's a quality of life alignment and
00:18:54
low wages. And I think there are a lot of
00:18:57
people who are working multiple part-time jobs.
00:19:00
And I don't know that I would say that they're all entitled,
00:19:03
especially since I don't really don't want in their friends or
00:19:05
no, press hammered, Uber for years over driver, pay and more
00:19:10
and more Drive. Let me finish carry driver after
00:19:12
driver, after driver has now, you know, embraced Uber and
00:19:18
they're making thirty six dollars.
00:19:19
An hour is a perfect example of like the Press were all over
00:19:22
this new Innovative product that it turns out people voted with
00:19:25
their dollars, people voted with their time.
00:19:27
People want the flag. I mean like I don't have any
00:19:29
skin in the game in Denver and I use Uber.
00:19:31
I have a lot. I will say still have a lot,
00:19:33
just had a conversation with a driver.
00:19:35
I had to wait, 14 minutes for an Uber the other day and I got,
00:19:38
and I was like, why was the way so long?
00:19:39
And he said, well, We have all decided we don't want to drive
00:19:42
as much because we were taking a bigger cut of our salary.
00:19:46
And he was sort of showing me what we made.
00:19:48
So I was very curious to see what he was going to make on my
00:19:50
ride which was for me $18, he didn't make seemingly that much,
00:19:54
I don't know, but it's funny that you say he's making thirty
00:19:57
six dollars an hour. That's the average total era
00:20:01
said in the last quarter, so you will find employees who have a
00:20:04
process cause in a while. I don't want to hold on, I'll
00:20:12
tell you before we get there, I want to just say one point.
00:20:15
Finally, on this, the issue is not any one of these individual
00:20:17
Stories. The issue is that nine out of
00:20:20
ten stories in the New York Times is incredibly negative
00:20:23
about tech. Now, when I was coming up, nine
00:20:25
out of ten, were probably positive for any positive
00:20:28
positive and it probably would be there are positive stories to
00:20:32
tell and there is not balanced right now and whether it's the
00:20:36
Tech Industries fault because things went off the rails at
00:20:38
times or wealth. E, it feels unfair.
00:20:42
I mean literally she with anyone talking in 2016.
00:20:45
Just to sort of I mean we you made the point first of all
00:20:49
that, like when people get escape velocity, they're only
00:20:51
going to speak with people who there certain are going to use
00:20:54
kid gloves. Like there was an
00:20:55
acknowledgement at the time. Sure that the people were
00:20:58
shopping for safe places to go access journalism.
00:21:02
You were talking about code and we were all being pretty gentle
00:21:05
and you know we all like Cara but there was a reality that
00:21:08
like people knew that they, you know, She I think you said
00:21:12
they'll ask the hard question, but they won't ask the hard
00:21:14
follow-up question. You know, there was sort of
00:21:16
already then in 2016, there was sort of a sense that, you know.
00:21:22
Yeah. Attack was very Savvy about
00:21:24
avoiding sort of difficult questions.
00:21:27
And I guess, I think what Katie's getting that is, what
00:21:29
happened is the workers got very - right, I mean, the sort of gap
00:21:34
between the management of workers spread do discover.
00:21:38
The reason we couldn't write a negative story before, For that
00:21:40
is because the workers wouldn't talk.
00:21:44
I mean or that's your that's your assumption.
00:21:48
It could also be that they felt great about the companies they
00:21:50
worked at, you know, Google employee 15 years ago, have
00:21:54
anything to complain about probably not honestly think it's
00:21:57
Jenner. I think it's like a big part of
00:21:59
this is generational, like I think people just look at work
00:22:02
differently today than they did and when I started in the tech
00:22:05
industry, you were signing up for 60 70 hour weeks.
00:22:08
You were part of like this pirate Samurai like you know off
00:22:13
the grid. Kind of you know revolutionary
00:22:16
Squad and now text so big that it's everybody and so you're
00:22:20
going to have people who maybe don't want to work as hard or
00:22:23
they're not necessarily consider themselves, Pirates or
00:22:26
barbarians or whatever Steve Jobs and Bill Gates or a framed
00:22:29
it as during the era, I came up and that's fine.
00:22:32
I actually don't have a problem with people who want to work,
00:22:33
nine to five jobs in Tech, there's room for that and
00:22:36
there's room for people who want to work 60 hours a week, I have
00:22:38
it inside my own companies. You know, some people are work
00:22:41
to live in some people live to work Vive.
00:22:43
La difference as far. Far as I'm concerned, if I'm
00:22:45
being honest. Yeah, but I think we're in
00:22:47
agreement here that like a lot of this with a change in
00:22:50
attitudes toward work and there was a time when yes, people were
00:22:55
so happy. Working at Google, you could
00:22:56
call every single employee at the company.
00:22:58
You would never get anybody to tell you anything other than
00:23:01
positive stuff. And so, the stories were
00:23:03
positive. Yeah.
00:23:04
But then they tripled their salaries and gave them more
00:23:06
benefits and unlimited vacation. So, if there's any reason to be
00:23:09
mad at your employer, you know? Well, sure.
00:23:12
But that's what is the entitlement.
00:23:14
Came in. Do you feel Tom that the tech
00:23:17
industry went through a period of extreme entitlement?
00:23:20
Oh, absolutely. And I think it's the, you know,
00:23:21
it's coming home to roost for a lot of these companies right now
00:23:24
because you saw Google as the prime example of this, you know,
00:23:28
setting out these unbelievable perks for all their employees
00:23:31
and as a realizing as they're trying to get people to come
00:23:33
back into the office and find, you know, the same sort of issue
00:23:37
wada, work that they may have had a couple of years ago that
00:23:40
they don't feel it, you know, they've gotten used to a certain
00:23:42
standard of, you know, Snacks in the break room and, you know,
00:23:46
days off and resting investing. And all the stuff that came with
00:23:49
being, you know, a highly desired worker that they can't
00:23:53
recapture for a lot of the same reasons.
00:23:55
But you know what, I when I looked at me we can zoom this
00:23:57
back or push this back towards all in.
00:24:00
It seems like there is a politicization of a lot of these
00:24:03
companies as well. And I've seen a lot of the
00:24:05
communication teams that run these companies.
00:24:08
A lot of them came from the politics world and I think that
00:24:10
the coverage of these companies and Katie can speak to this
00:24:14
Better than anyone here. Mirror is a lot of the way
00:24:16
political operatives communicate and and the reporters themselves
00:24:19
kind of view themselves as almost political reporters.
00:24:22
And I don't know how often I see politicians say oh man, the
00:24:26
coverage of Congress is to - these days, you know.
00:24:29
God you guys are only writing about the scandals.
00:24:30
Why do you talk about all the good bills that we do?
00:24:33
And it's like well, okay, sure, first of all, pass a bill that
00:24:35
also, you know, there is just a reality that with the greater
00:24:39
power and almost political violence that these companies
00:24:41
have there's going to need for the press to write about the
00:24:44
These things in an almost political way, and that itself
00:24:47
is going to just skewed more towards the - I mean, don't you
00:24:50
view? Some of this is almost a success
00:24:52
of the industry that you've been a part of for so long.
00:24:54
That because he's coming so powerful.
00:24:56
They get covered in a way where you question, you know, the
00:24:59
roots of that power and the people at the top of these
00:25:01
companies, 100%. Yeah, I mean this really all
00:25:05
goes back to one company and that's Facebook really
00:25:08
Zuckerberg, you know, he had a pretty a moral compass, you
00:25:13
know, in terms of how to run. Business.
00:25:14
And, you know, it created massive second and third order
00:25:19
effects for society and I think that was like the Turning Point
00:25:22
as far as I'm concerned of when like the press and Tack kind of
00:25:26
split up and it became like pretty hostile and cantankerous.
00:25:30
I think it was that company. And I saw at all kind of go
00:25:33
downhill after that, and you're pretty critical of sock, right?
00:25:36
Ice the worst actor intact. Okay.
00:25:39
But other than that, I really don't have much of an opinion.
00:25:41
No, I mean put it I'll put it this way, you know?
00:25:43
I'm Old school, like people, create products and services
00:25:47
and, you know, there's some love or Joy with the Creator like say
00:25:51
I'm Spiegel and then to blatantly ripoff, Evan Spiegel
00:25:54
away, he did over and over and over again amongst the digerati,
00:25:59
you know, the creators of companies.
00:26:01
It was just like is this really where the industry is going like
00:26:04
Evan Evan Williams or Jack would not do that.
00:26:08
Kevin Systrom with Instagram would never do that.
00:26:10
He did it under duress, obviously when Zach put a gun to
00:26:13
his head and You know, copy stories and put it in Instagram
00:26:16
and so it just it got rid of kind of this congenial like yeah
00:26:21
sure we might take inspiration from what you're doing but we're
00:26:25
going to make it our own, right? So okay sure, you know, every
00:26:29
phone needs to have a calculator and a flashlight and you know,
00:26:31
there's some basic stuff but we're not going to just
00:26:33
wholesale, rip everybody off and I think that was like why he was
00:26:37
so hated in the industry is that he was just this copying
00:26:40
machine. And it was almost like the Borg
00:26:42
came into the industry and kind of You made it just not fun.
00:26:45
Yeah and it was just relentlessness if you don't, if
00:26:47
you don't remember, he did like a poke app and then he to do
00:26:50
like ephemeral messaging and he did like four or five swings at
00:26:53
the bat to try to like take on Snapchat.
00:26:56
Oh I remember it really? Well as a matter of fact I
00:26:58
remember the first time they redesign messenger and it looked
00:27:00
exactly like Snapchat and I took a screenshot of it.
00:27:03
This was at 8:30 and I sent it to Evan that snap and I was
00:27:06
like, does this look familiar to you?
00:27:08
And I think he just responded with like, a rolly eyes emoji.
00:27:11
Sigh. It's like a sigh, you know.
00:27:13
It's just It's kind of rough when you know.
00:27:15
But anyway, putting it aside, you know, I think there's
00:27:19
actually a pretty cool path forward.
00:27:21
Yeah, things don't work. What is?
00:27:23
Well, yeah, it's pretty actually a straightforward.
00:27:24
It's actually happening right now which is if the tech
00:27:28
industry in journalists who work together can be all be
00:27:30
self-aware and listen to each other a little bit.
00:27:33
The criticism, you know, that Tech will have of the presses
00:27:36
like maybe for every two or three stories, where your slam
00:27:38
us can, can we get a profile of something new and interesting?
00:27:42
That's you know, maybe Be not trying to destroy the founder
00:27:45
and get them fired. You know, whether they deserve
00:27:47
it or not, we can debate, but the percentage of coverage the
00:27:50
blend feels unfair and it depends on the publication of
00:27:53
course, but with a company like the New York Times like they
00:27:56
people have just given up talking to but you're pretty
00:27:58
cynical oh like crypto, right? I mean we of course times yes
00:28:02
sort of bullish nft peace and looks silly.
00:28:04
You know it feels like when they we have been in a period where
00:28:07
there hasn't been some great new platform.
00:28:09
There isn't like there a lot of great SAS companies which I
00:28:12
write about all the time but Aren't these sort of singular
00:28:16
platform companies like a Google or an apple that you can point
00:28:19
to right now, or do you are there companies you think really
00:28:23
deserve? That's the me.
00:28:25
Yeah, they're not going to get as many clicks.
00:28:28
And what we have to also recognize as journalists is that
00:28:30
our industry has now moved into compensation, is tied to your
00:28:36
follower count, your ability to drive clicks, and your persona
00:28:39
and now that didn't exist as much when I was coming up, there
00:28:42
was an occasional wall. Mossberg or columnist, Etc.
00:28:45
You know, people who are critics, who had outsized
00:28:48
compensation and deals. But now, you know, when I went
00:28:51
to sell my first book and doing the second one, now your podcast
00:28:56
Rank and your follower count drive your advance or the number
00:29:00
of emails. Your job in journalism, if you
00:29:04
have a quarter million followers or 2500, your compensation will
00:29:08
be decidedly different. So there's a, you know, a little
00:29:11
bit of a perverse incentive now To be full contact to get those
00:29:16
clicks. Here's my question for you Jason
00:29:18
because I think you've outlined a very interesting Dynamic
00:29:20
that's happened with in journalism and I don't disagree
00:29:22
with you to an extent. We've seen this move towards sub
00:29:25
sex, come or or generally the I don't like, how do I relinquish
00:29:29
being a journalist so I can just get this fee direct.
00:29:32
Yeah. It was Casey making at the New
00:29:36
York Times versus stuff. The sub stack, we use
00:29:38
everything, your husband, The Verge.
00:29:40
But I hear what you're saying, average, rather here's my
00:29:42
question just because I think what I What?
00:29:44
I don't quite understand in this argument, which is an
00:29:46
interesting one, which is that your argument?
00:29:48
Is that the more you focus on your brand, the more it
00:29:51
subverts, the quality of journalism, right?
00:29:53
And you need to get the clicks and you're more inclined to and
00:29:55
negative stories. It's that 100% Carlo could a
00:29:58
cat. But do you at all because you're
00:30:00
a personality? I mean, I've known about you on
00:30:02
the scene for a long time. You're a journalist, you're, you
00:30:04
know, you have a million journalist anymore.
00:30:06
I'm clearly a commentator, but was previous nature, right?
00:30:08
And but you also are, we're a known quantity.
00:30:10
I just feel like, I've known your name, you know, within the
00:30:13
journalism, Real world for a long time.
00:30:14
Do you not at all? Feel that you were part of that
00:30:16
Trend that you further that at all that, you know, I further
00:30:18
did for sure. I mean, just hiring Peter Rojas
00:30:21
to be our partner weblog zinc and doing Gadget well, part of
00:30:23
that. Yeah.
00:30:24
I mean, I'm not saying that the trend is the trend, Tom.
00:30:29
The question is, how does it impact coverage and how does it
00:30:33
impact reporter Behavior? How does it impact a journalist
00:30:36
behavior in this age? I think what journalists are
00:30:39
going to learn over time as they need to be a brand independent
00:30:41
of like, Taylor Ranch might be No, the canonical example here,
00:30:45
you know, if your brand has to get bigger than the publication
00:30:48
and she's built the brand that's bigger but that's not solving
00:30:51
your objections to journalism. I guess it.
00:30:53
How did you get that brand? How you get that brand?
00:30:56
How you can get that flywheel going?
00:30:58
I think is the issue. I think actually the criticism
00:31:01
of the wall Tara or the Kara Swisher Arrow.
00:31:04
So if we're going to like compare the criticisms, yeah
00:31:07
eras. And I'm not saying this is my
00:31:08
criticism, this is the criticism inside of Journalism and inside
00:31:13
of the I'll sort of sweet is back then it was access.
00:31:18
So if you had access to Steve Jobs, Kara swisher and Walt made
00:31:23
at least a million or two million dollars each doing those
00:31:25
conferences, right? So then you have to ask
00:31:28
yourself, okay, would they write the most critical piece or not?
00:31:32
They would like to think they would and then access could be
00:31:35
removed. And so and Steve Jobs having
00:31:38
done this with directly with Steve Jobs in a gadget, he
00:31:41
pulled our access that Is a major Financial hit.
00:31:45
When he pulled our access to going to the Steve Jobs,
00:31:47
Keynotes for Engadget, that could have been a death blow.
00:31:50
And I had to negotiate directly with Steve Jobs, to get Engadget
00:31:54
back inside the, the, you know, the right Apple Keynotes.
00:31:57
And so, you know, when you're the publisher of the CEO, you
00:31:59
can see this up close and personal.
00:32:01
I don't think that people had to compromise their coverage back
00:32:04
then, but it certainly had to be on the minds of the Publishers
00:32:08
and the CEOs of coverage and now it's probably too negative.
00:32:13
And it's probably too - because that also drives views, I do
00:32:17
think paid content does change this a bit and I think that's
00:32:21
part of the endgame here. Subjects, co-direct the top
00:32:24
journalists have paid Publications and the search for
00:32:28
truth gets even better for consumers.
00:32:31
But do you think the truth is emerging through direct like
00:32:36
there's so many different types of articles in journalism.
00:32:38
But like it's very hard, like the ft x scandal, you guys are
00:32:42
fairly negative on the media. 'He and sort of positive about
00:32:46
Twitter accounts, you know, surfacing information, but like
00:32:49
coin desk. You know, really sort of move
00:32:53
the needle in terms of saying that there was something amiss
00:32:56
at Alameda research. And I feel like a lot of the
00:32:59
narrative through lines. How people understand the
00:33:01
stories even the apology, David Sachs, all these people are
00:33:05
extremely negative about the media.
00:33:07
Tweet out links to stories all the time.
00:33:10
I guess it can just, it can be frustrating.
00:33:12
The people are so so- about the media.
00:33:15
And then so clearly rely on the media.
00:33:18
For their worldview or to know what's happening.
00:33:22
He's even things, connected person, the world can't can't
00:33:24
piece everything together themselves without some some
00:33:28
reporting. I think independent journalists
00:33:31
and voices is good for journalism and I think subjects
00:33:35
going direct is good for journalism.
00:33:36
It gives people more access and more direct access.
00:33:40
I think that's actually a good thing.
00:33:41
It's going to be a little more messy like you don't just open
00:33:43
the New York Times and Trust everything and move on with your
00:33:45
day. You don't just turn on CNN and
00:33:47
accept everything. Gospel nor should you trust any
00:33:50
CEO or powerful person with their own podcast directly
00:33:54
communicating? They all are going to spin it in
00:33:56
some Direction but it's like Kurosawa and rashomon.
00:33:59
There's like your version of the truth.
00:34:00
There's mine and there's the actual truth as many versions of
00:34:02
trillion party hardy younger. You were touching on before
00:34:05
which I thought made a lot of sense like the axis journalism
00:34:07
piece of it. Basically, you know, They wanted
00:34:12
you know like a Steve Jobs to wanted your audience so they
00:34:15
cared about you being there and there was sort of a give and
00:34:17
take where they could take away access but you had some leverage
00:34:21
because they needed audience. Now with go direct the media
00:34:24
companies have less and less leverage.
00:34:27
Yep. So they don't have any weight
00:34:30
and fitting into an earlier point where you know if you're a
00:34:33
top person you want to go somewhere where you know, you're
00:34:35
going to get sort of positive coverage, what incentive does
00:34:39
somebody have? It's actually face hard
00:34:42
questions. Besides you just being sort of a
00:34:45
masochist to engage with people. But like most people, you know,
00:34:49
like they have no incentive. They have their own audiences.
00:34:52
So they have no reason to face. Yeah.
00:34:54
It's hard questioning. What's the solution that do you
00:34:56
think that's a process? The last time, has anybody here
00:34:58
has two hard questions in the CEO Tick-Tock recently?
00:35:00
I mean, has anybody been able to ask a hard question to
00:35:03
Zuckerberg? You know, right eye, he went on
00:35:06
Joe Rogan right here with you. He's going on Lex Friedman,
00:35:08
right. Gonna go for the Richard.
00:35:10
Will be more upset about that. Like I feel like there isn't
00:35:13
much you're not. You don't seem very upset that
00:35:16
people aren't getting Grissom. I honestly think it's a mess
00:35:19
right now and then sometimes things have to collapse in order
00:35:21
for something new to be built. I think that's part of the
00:35:23
process is that we're going through.
00:35:25
I think this is like the messy middle and there's something new
00:35:28
coming out the other side. The three of you were the four
00:35:31
of us here talking is part of that process.
00:35:33
I think it's the messy eye of the storm right now.
00:35:36
Putting aside my, you know, now that I can have opinions and
00:35:39
putting aside my Media concerns, I guess, I do worry that as a
00:35:44
fan of the show that you guys don't represent the Democratic
00:35:48
party and sort of left wing point.
00:35:50
I'm the only one. Yeah.
00:35:51
And your I mean, your mom, I guess he donates you agreed with
00:35:55
them that like balancing. The budget was your top issue on
00:35:57
the most recent episode I do. Yeah.
00:35:59
But I've always felt that way. I'm a modern vote for a Democrat
00:36:02
or Biden and then, I always chin.
00:36:04
I always vote for the best candidate.
00:36:06
I voted Republican three times in my life, Shameless partisan.
00:36:09
Like the guy is Is, I mean, he don't know.
00:36:12
I just I just feel like there and shimoff is clearly someone
00:36:15
who likes to be connected to the Democratic party, but it doesn't
00:36:19
he doesn't come off as like a True Believer.
00:36:21
I mean, I think what it is is the the Democratic party so far
00:36:24
left that moderates, don't feel at home in the party.
00:36:27
And I think that the Democrats just did well in the midterms
00:36:31
after Sachs was saying that would never happen show and you
00:36:35
guys you guys, oh, I said, I'm pretty sure.
00:36:38
I said it was about, I said it would be Predicted it would be
00:36:41
about Roe v-- Wade and I tortured sacks about it, if you
00:36:45
remember I've already got off pretty fast from being sort of
00:36:50
the like Red Wave. Proponent here, I don't know.
00:36:54
He was pretty honest that he got it wrong and he that the
00:36:56
Republican party needs to learn from it but they won't.
00:36:59
They'll never kick Trump out. It's very bizarre.
00:37:01
I'm like, if why don't you just say you'll never vote for Trump
00:37:03
and it's like well because he might win the primary I think is
00:37:06
going to win the primary, I'll be honest, I wouldn't count
00:37:07
Trump. I have you surveyed the
00:37:09
audience. Like I mean, it feels Well, I
00:37:10
guess if the Reddit, I don't know if you read the Reddit for
00:37:14
the all end but I do not. Yeah, are you?
00:37:17
By the way? I'm just lasting on the
00:37:18
political anger because both, you and sex are pretty outspoken
00:37:21
and local politics and the Bay Area in San Francisco.
00:37:24
Sure. Is that a thing you're
00:37:25
continuing to be involved with? I mean, obviously, you guys were
00:37:28
dead set on getting chase a removed as DEA, but are you
00:37:31
continuing to involve yourself and local politics here?
00:37:34
Have the done' name? Mayor Jason doctor?
00:37:37
So I have the domain and I've had been I had to me Dollars
00:37:41
offered to me to run for mayor like in campaign donations.
00:37:44
That from David sucks. Now I'm just hot, but but I'm
00:37:47
sure he would in our don't know what I did.
00:37:50
In that case was I just did a go fund me page and I wasn't
00:37:53
involved in the recall. I just hired a local journalists
00:37:56
to cover, strictly the cases and The Human Side.
00:37:59
And I only put five hundred dollars into what happened to
00:38:01
that. By the way, I remember seeing
00:38:02
that I've Gotham by the bay. She wrote a series of Articles
00:38:05
and those articles are picked up by national news that didn't
00:38:07
have the time to, you know, spend 30 40 hours.
00:38:10
Hours, chasing down people who have been the victims of crimes
00:38:13
and the prosecutor who gave all the violent criminals, like a
00:38:17
pass. So, you know, but that's as far
00:38:20
as you're taking that you're not going to try.
00:38:21
I mean, you know, obviously, Mike Morris has got his, his
00:38:24
local news outlet that he's spending quite a bit of money
00:38:26
on. You don't want to know, might as
00:38:28
well. You know.
00:38:29
I'm not a fan of politicians. I don't like politicians all
00:38:32
that much for hanging out them. I get invited to all these like,
00:38:35
you know, lunches and dinners. And then they tell me the price
00:38:38
I have to pay to have lunch with You know, Obama or the lunch
00:38:42
with, you know, Hillary or the lunch with the Santa's and I'm
00:38:46
like what? I paid 25 Grand to have lunch
00:38:48
with one of these people. I barely would want to hang out
00:38:51
with Polish all your friends like to do that, right?
00:38:53
I mean that I guess I don't know why it's not my thing.
00:38:57
I think I could have more impact investing in companies and
00:39:00
raising my kids and go my pockets with.
00:39:03
Are you? So you're not going to run for
00:39:04
mayor or You like, you, like, you guys, like, you guys all
00:39:09
know the value of floating Kara, I considered it loaded that
00:39:13
everybody was running for president.
00:39:14
It's a great compliment. Do you think David Sachs really
00:39:17
wants to be a secretary of state?
00:39:19
You guys have, he would definitely be a cabinet and I
00:39:20
will guarantee you he'll be a Cabinet member at some point for
00:39:23
sure. We will be visiting sacks in the
00:39:25
white house. Will do it all in pod from the
00:39:27
White House. That's it for our lives are
00:39:29
over. Like I sure do not believe that
00:39:31
if could be interviewed by what's-his-name from Barstool
00:39:34
Sports you can I have no doubt that there is it's open season
00:39:39
on who would appear on a podcast I think he's hundred percent
00:39:42
going to be in there. Yeah you don't want to talk
00:39:44
about it but we have to put something.
00:39:46
We what will you say anything about social media?
00:39:48
These days are, you know, you're in the house.
00:39:50
A huge fan of social media. I use social media all day long
00:39:53
days. Well, I mean, I think I find
00:39:59
Tick-Tock completely addicting and I feel really horrible
00:40:04
anytime I use it because yes, sure.
00:40:06
Short half an hour goes by and I'm like, what just happened?
00:40:09
Yes, I deleted it. When I realized I was on
00:40:11
Tick-Tock one day for seven hours.
00:40:13
Goodbye. Yeah, it's they really figured
00:40:16
something out. I think it's a real National
00:40:17
Security risk. I think have to ban the company
00:40:19
or make them well, it's interesting because even if
00:40:23
there are some security risk, you know, China does not allow
00:40:27
Instagram to be used in China. Why would why do we have to
00:40:30
allow a Chinese social media up to be used in the u.s.?
00:40:33
There's a student does not reciprocity.
00:40:36
Ders. We're talking about Tick-Tock
00:40:38
these were trying to ease our way into asking a Twitter
00:40:40
question. We ask you about the Twitter.
00:40:45
You can ask God, This from a totally
00:41:07
different topic. So Eric Tom bear with me.
00:41:10
Can you walk me through? Why?
00:41:11
You can't? Because you used to be receptive
00:41:13
to all this stuff. I am a little too close to it
00:41:16
and then people will, of course, reblog whatever I say.
00:41:20
So when I, when Travis was, you know, running Uber people
00:41:24
assumed that I was a proxy for Travis in other situations.
00:41:29
People assume I'm a proxy for other individuals or that I am
00:41:33
like an official spokesperson or a back Channel or where they
00:41:35
call those people who are in Ticks surrogates yo, so I have
00:41:39
chosen that I don't talk about my friends.
00:41:40
Yeah, it's great like we were talking about his fans with.
00:41:44
Go ahead. Eric.
00:41:45
Well where are you saying we were talking about this before
00:41:47
the show like there aren't enough.
00:41:49
Not with, you know, we were saying this but there are, you
00:41:52
know, there aren't enough surrogates right now.
00:41:53
I think part of the reason, the media has become so - to tie
00:41:57
back to the beginning is because workers are the sources
00:41:59
available. You know, Ilan, what did he fire
00:42:02
like the whole cause of her? They're not the Twitter stories
00:42:05
are just about what the work. As are saying a word with you
00:42:07
guys, was an awesome to be on the ha.
00:42:09
Ha. Ha.
00:42:10
Peace. All right, we'll change the
00:42:12
subject. Yeah.
00:42:15
Leave me out of it. Is it is, I'm a huge fan of the
00:42:18
Twitter app. Yeah.
00:42:20
Yeah, let's change. I like Katie's approach 0, as a
00:42:27
journalist. Here's here's my Katie is such a
00:42:30
better doing this like from an era from World.
00:42:33
Exactly, but here's why Katie you are so much better of a And
00:42:36
Tom and Eric, put together cause I don't just scream at you for
00:42:39
the record. Jason, I have not been yelling
00:42:40
at all here at my strategies reporters but people talk and
00:42:43
talk and talk until they say, mocking sounds and of course,
00:42:45
yeah, I'm breaking your job. Stop you are an excellent.
00:42:48
Do I have to do there? Reporter Chuck careless in my
00:42:51
opinion. Jacob, I actually my first time
00:42:55
meeting you. I kind of cornered you into
00:42:57
talking, to me. Oh, really.
00:42:59
But this it all? Yeah, because you would just
00:43:00
pivoted follow inside.com and PTSD.
00:43:05
Yeah, you wouldn't talk to the Press All and I emailed you
00:43:08
think I found out what you're doing.
00:43:09
If you don't talk to me I'm going to I'm going to write a
00:43:11
scoop a little little time. This piece is coming at us 5
00:43:16
a.m. with or without your participation mr.
00:43:19
Kenneth but I will say that I did that myself.
00:43:21
Yeah, but but for my time and Lolly, one of the things that I
00:43:23
knew that, you know, the most about you is that you were an
00:43:25
early supporter and friend of elon's, I mean, you knew him
00:43:29
from the sirens days you were one of the I think so you were,
00:43:31
you were driving like the preet. I have an early Tesla given
00:43:35
every Tesla and I have Tess was a great car and I remember 16 of
00:43:39
the Roadster and number one of the model S.
00:43:42
Serial number 000, 00 one signature.
00:43:44
And I remember you saying it an interview once that, you know,
00:43:47
after Ilan, he was really down on his luck for a while, you
00:43:51
know, because PayPal, and before Tesla started doing well, he was
00:43:54
broke. Yeah.
00:43:56
And and, and he had talked to you about it.
00:43:57
So you were kind of there for him at a time that he was out as
00:43:59
low as so. You understand him at, you know
00:44:01
the various states of his success and non-success.
00:44:05
What do you think we are missing about?
00:44:06
Ilan as the press, in terms of writing about him.
00:44:09
I have been lucky enough to have a lot of great friends in Tech
00:44:14
and he is one of the great entrepreneurs of our time and
00:44:17
you will figure everything out. It's the beginning in the end of
00:44:20
it with, as much as we can say about you Lon.
00:44:23
That's it? Because I do not speak for Ilan.
00:44:26
I am not a proxy for Ilan, he is on Twitter right now.
00:44:29
You can hit you can you can text me email them to come.
00:44:31
On the show. Let's talk about Twitter on a
00:44:33
different episode. I am curious, like I mean you've
00:44:35
been skeptical. I love crypto.
00:44:38
Like what do you make of sort of the FTX unraveling?
00:44:43
Like, how much worse do you think this is going to get?
00:44:46
I think that 99% of it is fraud and incompetence.
00:44:52
I'm talking about the entire crypto space and one alleged
00:44:56
alleged after you have answered alleged alleged but not looking
00:45:01
good. I think 99% of crypto based on
00:45:05
the meetings I've had and I've been hundreds of meetings, I've
00:45:08
had over the years, I'd say 99% of it is a grift or incompetence
00:45:13
or some combination of grifting competence and naivete.
00:45:17
The technology tool stack that you would call Web. 30 is a
00:45:21
collection of interesting components of other Technologies
00:45:24
whether it's encryption or decentralization, we had
00:45:26
decentralized BitTorrent or Nutella or whatever their
00:45:30
encryption Technologies existed blockchain technology.
00:45:33
All this stuff is like you know, interesting components But other
00:45:37
than Money store a money transfer.
00:45:38
Most of this stuff does not have a viable customer base.
00:45:42
And so, almost all of the companies I met with, I would
00:45:45
ask them to show me the product or talk to me about the
00:45:47
customers, they show me a white paper and tell me I was stupid.
00:45:50
And you know, when I had them on the podcast I say hey had do
00:45:52
Quan on the Pod hey explain to me what this tarot Luna thing
00:45:55
is, he could explain it, I asked them three times to explain it
00:45:57
to me, you couldn't explain it. I was like well I don't get it,
00:45:59
I guess I'm dumb and I'm one of the greatest Angel Investors of
00:46:02
all time and have been in tech for 30 years.
00:46:04
So I know I'm not the smartest guy.
00:46:06
But I'm definitely not the dumbest guy.
00:46:08
I should be able to get you live through like the.com.
00:46:10
Boom we have the crypto. This is worsening.
00:46:13
This is worse. Craig was much worse.
00:46:15
Chemically more like what its impact or in the.com Era.
00:46:20
People were true believers. They thought they would figure
00:46:24
it out. And the thing, got overhyped, in
00:46:28
this case, I think people are deliberately buying tokens
00:46:32
flipping them to retail. And I think when the
00:46:35
investigations come out, It's going to be a really bad look
00:46:38
for a lot of people in the tech industry Beyond crypto or only
00:46:42
crypto. Just it's crypto is where this
00:46:44
is manifesting. There's, you know, when you buy
00:46:46
shares in a startup you're locked up for 10 years, right?
00:46:49
Like I buy Uber, or I have Robin Hood shares.
00:46:52
Yeah, maybe some secondary offerings, come Masa comes in,
00:46:55
or Yuri, Milner comes in wants to buy some people shares.
00:46:58
You know, privately can happen. It happens one out of a hundred
00:47:01
times. You know, this was, I think
00:47:04
people because I was in such These meetings and I was
00:47:07
watching people do this, they were lawyer shopping, which is
00:47:11
where, like a lawyer doesn't give you the answer you want.
00:47:13
So you just go to like the fifth sixth, seventh point.
00:47:16
You start going down like two lawyers and Cayman Islands,
00:47:19
lawyers in Panama and all of a sudden some lawyer for a million
00:47:22
five tells you yeah we can totally set this up in Panama
00:47:25
and whenever you're picking a jurisdiction and a law firm
00:47:30
based upon the eventual outcome that you're going to get sued or
00:47:34
arrested you're doing something. Being that you probably
00:47:37
shouldn't be doing and if you can't do it in Delaware, if you
00:47:40
can't do it with a Wilson sonsini or whatever Law Firm
00:47:43
Fenwick or you probably shouldn't be doing it.
00:47:46
And so I was watching Founders getting these like legal
00:47:49
opinions and then setting up these, you know nonprofits or
00:47:54
know where they would store the coins and they would sell the
00:47:57
money. And then VCS were buying the
00:47:59
coins and then liquidating them. And there's no, there's a whole
00:48:02
zoo injuries law. It's is oh, do they invest in
00:48:06
crypto? They were involved.
00:48:08
So just just a bit. I hear it said of instead of
00:48:11
the.com bust it's more like the junk bond scandals and the penny
00:48:14
stock can't scandals of the 80s where it was like totally
00:48:18
unregulated. People were making the rules.
00:48:20
They were shopping for attorneys, it's almost the same
00:48:22
exact pattern and then flipping everything to retail and getting
00:48:25
out and then screwing an entire generation for investors.
00:48:28
Is that what I think it is? You just said that's what it
00:48:31
feels like to me. For sure.
00:48:32
That day I like because and it doesn't find out about analogy
00:48:36
it Yeah, the.com thing was just a bunch of like, folks who
00:48:39
thought, hey will eventually figure this out, you know, and
00:48:42
we may not have enough people right now to justify this
00:48:44
valuation but we'll fill it in. It wasn't like I'm going to buy
00:48:47
a bunch of these tokens and then I'm going to sell them on
00:48:50
something to a bunch of, you know, bag holders in the public.
00:48:53
And I'm going to start doing podcasts about how amazing
00:48:55
cryptos going to change the world and use my previous you
00:48:59
know trust in my brand to go flip these things.
00:49:01
Right? And you know there are some
00:49:03
moments of things being real. I do think like nfte Ticketing
00:49:07
or four mayb stock photography or music licensing.
00:49:11
Where, like, I took the stock photograph, I work for the New
00:49:14
York Times and I agreed with them.
00:49:15
As a Stringer, they get half the rights.
00:49:17
I could have the right. There's what it hopes and
00:49:19
dreams, you know, things could be dope.
00:49:22
Yeah, Dow's douse. Have some interesting
00:49:25
components. I've looked at those now, it's
00:49:27
not legal, but when you look at Securities Law and you decide,
00:49:30
I'm going to break Securities Law because somebody in another
00:49:34
jurisdiction, told me, it's okay.
00:49:36
Shame on you. It's one thing for Airbnb to be
00:49:38
like, you know, I think these laws around what's a hotel and
00:49:42
what's me renting? A place renting, an extra
00:49:44
bedroom. I'm going to interpret it this
00:49:47
way and there's no consumer harm when there's no consumer harm
00:49:50
and you want to bend or evolve the rules for ride sharing or
00:49:54
for you know, airbnb's that's one thing because you always
00:49:57
have the consumers who come to your events defense and say
00:50:03
listen, I'm making eight hundred dollars a month right now.
00:50:05
Selling my extra room justo The government to tell me, I can't,
00:50:07
it's my room, I'm paying for it. Well, don't we have property
00:50:09
rights? The same thing with Uber right
00:50:11
Wilbur took that strategy in New York, lifted that strategy.
00:50:14
Hey, tell the mayor de Blasio that you know, we shouldn't have
00:50:17
a cap on Ubers because of this evil Medallion industry.
00:50:19
Now you go to, you know, these crypto folks and it's like yeah,
00:50:24
you need to defend my right to sell some, you know, you know,
00:50:28
civilians in Florida these tokens that are worthless and
00:50:31
it's like what? Yeah, this is like the Wolf of
00:50:33
Wall Street. Don't you think the same thing
00:50:36
could be being said about spax like have you guys been hard
00:50:39
enough? Just because I liked about this
00:50:43
back craze. Okay, so in terms of facts, one
00:50:47
of the things. So there are a range of specs
00:50:50
and I've had a couple of my companies go public - back and
00:50:53
it's a little bit frustrating because as much as you want to
00:50:56
get liquidity for your investors, we had desktop metal,
00:51:00
a really cool 3D printing company, very real company with
00:51:02
real customers that love. Are real products.
00:51:05
But we had company staying private for too long, like uber
00:51:08
and Airbnb and then we start to have companies going public too
00:51:11
early. If the framing of these
00:51:13
companies was to the public, these are highly speculative
00:51:17
Investments. Do not make them more than five
00:51:19
percent of your portfolio to percent of your portfolio.
00:51:22
Whatever it would have been fine.
00:51:24
But the problem was you had this Robin Hood, you know, Wall
00:51:28
Street bats, you know, everybody betting on stocks in a very kind
00:51:33
of you know, aggressive fashion. And almost in some cases
00:51:35
gambling as opposed to like, but your mouth was the avatar for
00:51:39
this back. Well, some of those companies
00:51:40
are very real, you know, the company sees fact, some of them
00:51:43
are very real and then some of them like, you know, a Virgin
00:51:46
Galactic are like a speculative. You can get, I don't have a
00:51:49
problem with adults, buying a speculative company or a real
00:51:53
company that has, you know, five years worth of Revenue or one
00:51:56
that doesn't they just need to be educated properly, you know?
00:51:59
And so I think it was almost like they were too successful
00:52:03
with L investors the retail investors needed to not run
00:52:07
these things up but that's what happens in the market.
00:52:10
Like I think Joe be the The veto company you know I don't have a
00:52:13
stake in this a cup of my friends invested in it.
00:52:15
I got I want to buy the shares in that company, I've been
00:52:17
watching it like to do a j trade.
00:52:19
Like maybe I should buy some of this because it's it's cheaper
00:52:22
than it was as a public company. Even BuzzFeed BuzzFeed is worth,
00:52:25
250 million or something crazy like buzzfeed's doing three or
00:52:30
four hundred million in Revenue but their valuations. 250 what
00:52:33
BuzzFeed I've decent media property.
00:52:35
Why is it worth so little and that one out by his back.
00:52:37
So yeah specs we want to have more that we want to have more
00:52:42
public companies and we want to democratize access to them,
00:52:45
right? But it was probably the bad
00:52:47
timing of when this happened, when retail was kind of losing
00:52:50
their minds. Buying everything that was a new
00:52:52
issuance and, you know, trim off can defend himself if he wants
00:52:55
to, but, you know, I think it's so fun to talk to him.
00:53:00
So, you know, if there's right you mentioned at the beginning
00:53:03
of the podcast. There's obviously so much going
00:53:05
on right now. How do you sort through and
00:53:07
determine how would you rank the tech stories happening right
00:53:10
now? In terms of like broad
00:53:12
importance beyond the tech industry which are the most
00:53:15
important like three stories. Do you think?
00:53:18
Well, the most important stories is, how many people does it take
00:53:21
to run Amazon, or Google or Facebook, or another company, or
00:53:26
any other company, think a company, any company until?
00:53:29
And the truth is, people were hiring for a growth cycle.
00:53:34
That was two or three years out, that was kind of how Larry and
00:53:37
Sergey explained it to me back in the day with Google.
00:53:40
They just wanted to get as many many talented people in the
00:53:42
building as possible and then figure out what to do with them
00:53:45
later and everybody copied that Playbook and it was also a
00:53:49
blocker strategy. They wanted to have smart people
00:53:51
in the building. Let them run amok.
00:53:54
You know self-organized we're paying you three or four hundred
00:53:56
grand a year but you figure out what you want to do.
00:53:58
Go find to interesting people in run work.
00:53:59
Ed or Google+ or come up with Google video, you know, just
00:54:03
self-organized. Whoo.
00:54:04
Carrots. You know, we're we have a
00:54:05
money-printing machine that strategy permutated all
00:54:08
companies, whether it's boober, which hasn't done a riff
00:54:11
recently or Airbnb, which did a bunch of riffs and got to
00:54:14
profitability and Facebook the mighty Facebook, you know, he
00:54:19
finally decided to cut the staff.
00:54:21
So I think what we're going to see is a lot of companies,
00:54:24
getting a lot smaller in Tech and a lot more focused and it's
00:54:29
going to be a pretty brutal 20:23.
00:54:31
I predict that being said, I'm investing more than ever.
00:54:34
Because now valuations for start-up companies where I
00:54:36
invest, you know, they've gone back to when I invested in Uber,
00:54:41
it was a five million dollar company and you know, I see
00:54:45
companies regularly that don't have the traction and don't have
00:54:47
TK that are asking for 25 million and I'm like, hmm, like
00:54:53
your no TK. This company doesn't have the
00:54:56
promise of Uber or so, why is it worth 25 million?
00:54:58
I'm saving myself. But now these valuations have
00:55:01
come back down to earth and then teams are doing more than less.
00:55:04
Oh, oh. Austerity for America, writ
00:55:07
large controlling spending austerity measures inside of
00:55:11
companies, it's going to be 20. 23 could be gnarly.
00:55:15
Let alone a black, isn't it? It's going to be ugly.
00:55:17
Yeah and then if we have a real recession, all right.
00:55:19
Well no, it's going to be, I think it would be a real
00:55:21
recession. What I'm worried about is, if
00:55:23
some unknown unknown happy about Taiwan or or Ukraine, Russia,
00:55:28
like we know about those. I'm worried.
00:55:30
I'm saluting like 9/11. Yes, yes, yes.
00:55:32
But 9/11 golfer, Add situation is really like that.
00:55:37
Could send this into a contagion like event where, you know, you
00:55:43
would have a lot of we could go from 3 or 4% unemployment to 10
00:55:46
and the 10 million jobs we have open could go to 0.
00:55:48
That's what I'm worried about right now.
00:55:50
Last question here. Jason just took forward here on
00:55:53
the media side of things. Yeah.
00:55:55
Where do you, where do you see that headed?
00:55:56
I mean, you mentioned BuzzFeed, let's not even touch them
00:55:59
specifically. But like, you know, what's going
00:56:01
to happen to, you know, the status It's of the Legacy Media
00:56:05
companies. Well I mean I did get Molly
00:56:07
would a career journalist as well to join me for this week in
00:56:09
startups so keep that in mind. So I'm pursuing both, you know,
00:56:13
I wanted to have somebody who's a great journalist like Molly be
00:56:15
my co-anchor on this week in startups for a reason.
00:56:18
She brings like a level of seriousness and credibility to
00:56:22
the Pod, you know, which kind of balances out my bash.
00:56:24
They can nature, she's robbing to your, to your Howard.
00:56:27
I get it probably more like more like my Molly would you know
00:56:32
like my credible Finance journalists like okay.
00:56:34
Not to diminish. Roger Bollywood yeah.
00:56:36
Molly's my mollywood. Yeah, that's it basically time.
00:56:38
She's like a super credible, you know, career journalist who
00:56:42
worked at the New York Times CNET and Marketplace so, but now
00:56:45
she's learning how to be an investor to.
00:56:47
So it's kind of neat. I would say, I think, you know,
00:56:52
the independent newsletter and the Kevin Kelly's thousand.
00:56:56
True fans is going to be very alluring to the top journalists.
00:57:00
And I think top Publications are going to just continue to pursue
00:57:04
Do subscriptions over advertising, so they can spend
00:57:08
more on it. I mean, the information is doing
00:57:10
a really solid job, Washington, Post doing a really solid job,
00:57:13
you know, that's put it on pretty stable, you know,
00:57:16
footing, I think the New York Times with their collection of
00:57:18
subscription assets, like the athletic and crosswords and
00:57:21
whatever wire cutter, pretty Savvy move and the more you have
00:57:25
subscriptions, the more predictable, it is in the less
00:57:27
you're dependent on click baiting strategies, like
00:57:30
Business Insider pursues you know, wouldn't know, it's not a
00:57:33
dig at me. But we, when I say something on
00:57:36
all in, you know, where we have a topic, they might drag that
00:57:39
out, five different stories that are all 300 words and, you know,
00:57:43
they, you know how they do sure yeseo the headlines, it's a
00:57:46
whole it's a whole thing. Yeah.
00:57:48
So you can't take the Washington Post, you know, and Insider and
00:57:53
Casey and Eric and you know like there's a lot going on here it's
00:57:57
not one thing. It's kind of feel like we're
00:57:59
talking about paper, you don't like to make a magazine or a
00:58:02
newspaper you can make Paper towels you can make toilet
00:58:05
paper. Like paper can do a lot of
00:58:07
different things and you know making content can be a lot of
00:58:10
different things. Yeah but I think is a s'mores
00:58:13
your vest in the universe right now.
00:58:15
Maybe to just ask an appointed way you think it's a good man
00:58:18
stuff. They didn't have a, if the New
00:58:20
York Times didn't have super voting shares, I would invest in
00:58:25
the New York Times. If they had, they have god
00:58:29
control over that company, legs anything, they just won't run it
00:58:31
profitably or I think they'll run it.
00:58:34
The benefit of their 6th 7th, 8th 9th, 10th Generation, not
00:58:38
the benefit of the public, or the shareholders or the
00:58:41
employees. Very interesting.
00:58:42
What value Act is doing right now, I find it fascinating that
00:58:46
they would even bother but to see them go in as an agitating
00:58:53
Force. It's just really tough.
00:58:55
I think the best thing the family could do would be To
00:58:59
figure out a way to. Yeah.
00:59:02
I guess this was a I guess this was season 2 of secession but a
00:59:08
way to make this in the Public's interest and and have like a
00:59:12
butt in succession, they're trying to sell it to the like
00:59:14
the murdochs. You know, it's not to the
00:59:16
public. You don't do you want them to
00:59:20
ourselves? I believe.
00:59:22
I'm happy with the elite family runs near times.
00:59:25
I think they do. You want to have met around the
00:59:27
New York Times forever? Eric, what you want to have,
00:59:29
man, run the New York Times forever is what you're saying?
00:59:31
No, I mean, they had a female editor at one point.
00:59:34
One point they did? Yeah.
00:59:35
Yeah. And this is what you want to
00:59:38
keep the patriarchy in charge, okay?
00:59:39
Eric, we know where you stand. You want the patriarchy two
00:59:42
legs. It's interesting.
00:59:43
When you're back on your feet, you bring up woke politics.
00:59:45
I thought you guys hated woke politics but I'm okay.
00:59:53
Thank you. I really appreciate it.
00:59:56
Thanks Jason. Goodbye.
01:00:09
Goodbye. Goodbye, goodbye.
01:00:11
Goodbye.