Back in the days of Web2’s infancy, budding The Wall Street Journal reporter Jessica Lessin had a hunch about how a few Silicon Valley newcomers could turn the business landscape on its head – when others didn’t want to believe it. That instinct proved to be right and eventually inspired her to build the technology publication The Information, which nine and a half years in boasts a fiercely dedicated subscriber base. We sit down with the founder to talk about how she’s creating stories to serve the next 50 years, the state of reporting in an era of disinformation, and the female founder conundrum.
See omnystudio.com/listener for privacy information.
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Good Company is a production of iHeartRadio.
Speaker 2 (00:03):
I really realized that business readers were not being well
served by the present state of business coverage.
Speaker 3 (00:15):
Hi, I'm Michael Casson. Welcome to Good Company. We're all
explore how marketing, media, entertainment and tech are intersecting, transforming
our lives and the way we do business at a
breakneck speed. I'll be joined by some of the greatest
business minds at strongest leaders who will share how they
built companies from the ground up or transformed them from
the inside out. My bet is you'll pick up a
(00:37):
lesson or two along the way.
Speaker 2 (00:38):
It's all good.
Speaker 3 (00:44):
Today, I have the great pleasure of speaking with a
very longtime friend, Jessica Lesson. Jessica is the founder and
the CEO of The Information and importantly, Jessica founded The
Information in twenty thirteen as an early player really in
building the next kind of leading business news publication and
(01:05):
since then, I'm proud to say I've been a regular
reader since the beginning. But I would think I submit
this to our listeners, but I think it's true in
our business in the way I describe our business, kind
of the intersection of marketing, media, advertising, entertainment, sports and technology.
Kind of think the information lives at that same intersection.
(01:25):
I think it's a must read. I kind of think
if you're not up to date, you don't have the information,
you're not going to be as up to date as
you need to be. So, Jessica, it's great to welcome
you to good company.
Speaker 2 (01:37):
Thank you so much for having me.
Speaker 3 (01:38):
Michael Jessica, I want to give a little bit of
a shout out to the fact that it's fun for
me to be having an interview with you, because for
so many years when you and I first met, when
you were at the Wall Street Journal, you got to
interview me.
Speaker 2 (01:52):
I was growing you all the time. Yeah, so no,
it's nice when the tables turn and I get to
put down the notebook.
Speaker 3 (01:58):
So well, there you go. You've had a remarkable career.
And again, when you were a journalist at the Wall
Street Journal and I was in the middle of some
important stories that you were following, I can say this
with my right hand to God, you were as good
as it gets in terms of getting to the point,
getting to the facts, and really not letting anybody off
easy in a good way, in a respectful way. I'd
(02:20):
love it if you could give our audience a little
bit of walk down kind of you know, Jessica's road
to today. You know, even before founding The Information in
twenty thirteen, well.
Speaker 2 (02:32):
I think I caught not just the journalism bug, but
kind of the technology journalism bug actually in college, and
you know, I was watching a new generation of founder
and entrepreneur build tech businesses and realizing that, you know,
these were going to be really important businesses Facebook, Twitter,
(02:52):
what was happening at Google? And got lucky enough to
join the Wall Street Journal out of college, where no
one wanted to cover those companies. I had an editor
tell me, you know, oh, Facebook, how are they going
to make money?
Speaker 3 (03:05):
And to me it had an investment advisor say to
me Amazon, They'll never make money.
Speaker 2 (03:10):
Yes, plenty of those stories and you know where people
saw like young kids and ping pong balls in their office.
I really thought this was the future business. Every industry
is going to be transformed by what's being built in technology.
Great tech companies will be built, but everything is going
to be changed. And over the course of covering those
(03:33):
companies at the Wall Street Journal, I really realized that
business readers were not being well served by the present
state of business coverage, which to me was not looking ahead.
It was not realizing that P ANDNG is, you know,
rethinking everything about its business and you know, becoming an
(03:55):
experting Google as much as the next business to acquire customers.
And so just.
Speaker 3 (04:00):
It's interesting because you and I talked about this back
then we had begun to work for Salesforce. I want
to remind you of this. And what Mark Benioff had
said to me back then was Michael. I interviewed him
at a keynote for CS I think you were probably there.
Speaker 2 (04:15):
Yep, that rings them hell for sure.
Speaker 3 (04:16):
Yeah, I think it was twelve years ago. And I
interviewed him and then he turned to me and said, Michael,
I want to interview you with my sales team. And
I said, why is that? He said, because I built
a company at that point twelve years ago on the
back of cloud computing, and now I'm making this foray
into the marketing cloud, and I need to understand how
(04:37):
to reach the marketer and not the IT person, because
cloud computing would have gone through the door of IT,
marketing cloud would go through the door of CMO. And
you might remember this. We came up with this view
that the CMO and the CTO were becoming one and
the same in many companies because a technology or just
(05:00):
to your point of Procter and Gamble as a for instance,
the chief technology officer at Procter and Gamble has to
know more and more today about marketing, and the chief
marketing officer has to know more and more about technology.
And so I used to kid around and say, the
person with the pocket square is now the same as
the person with the pocket protector hoodie.
Speaker 2 (05:23):
Michael, we liked refer to hoodies exactly, it's not as nerdy.
But no, and everywhere I looked, you know who was
joining the board of Disney, it was Sheryl Sandberg and
Jack Dorsey. And so when I thought of building a
business publication that you know, could build on what the
Journal and the Ft and Bloomberg have accomplished and the
readers they serve, but serve them for the next fifty years,
(05:46):
it was clear to me there was a big opportunity there,
both in terms of areas of expertise of reporting and
coverage and then also of course business model by kind
of starting with a very passionate subscription core. So, yeah,
after eight years at the journal I decided to take
the plunge and start the information, and now we're nine
(06:06):
and a half years.
Speaker 3 (06:07):
In its unbelieved.
Speaker 2 (06:09):
Hundreds of thousands of readers. So it's a little crazy.
Speaker 3 (06:13):
You've been a fierce advocate, both in your just pure
journalistic role but also now your entrepreneurial role, if you will,
of the facts and been a fierce advocate of dispelling
misinformation and really kind of getting to the truth whatever
that you know, I'm funny about that. I think truth
(06:33):
is still a word that can be defined. I don't believe.
I don't want to be political, but I don't believe
in alternative facts. I think that there are just facts
and there are truths, and I think you do as well.
But we're in a world where that doesn't seem to
be everybody's view. Any advice that you can give on
how you stay pure and so committed to that at
(06:55):
a time when it feels like that's a bit of
you know, multiple choice to people maybe is to say.
Speaker 2 (07:02):
It it's an incredible time, and then you add Michael,
you add Ai into this, honestly, And someone came to
me yesterday or a couple of days ago and said,
so you're going to hire a thousand reporters to like
be able to fact check, you know, what coat the
pope is wearing, or just as an example, because there
are memes out there, you know, now with AI you
can really distort reality. So for me, I answer that
(07:24):
question with the reporting process. I have a lot of
faith in who did we talk to, what did they say?
Is it verified? How does the person who told us something? No.
I'm constantly asking how does that person know?
Speaker 3 (07:38):
Right?
Speaker 2 (07:39):
And I think I am a little old school about that,
but I think even in a world where journalists are
only going to be contributing a small sliver to the
overall information ecosystem, that sliver is really really important. And
you know, that's the part of the problem I want
to work on, which is to ensure that continues to
(08:00):
be high quality, original reporting, that is accurate, and that is,
you know, as much as possible, tuning out the noise
and getting back to the basics of sort of what
do we know and how do we know it. I
think as a society we're gonna disinformation we've only we
haven't even scratched the surface of what's coming. But I
(08:22):
am optimistic because we are seeing massively engaged audiences for
quality journalism when it's introduced, and you know, we can
write a story about a troubled startup and you know,
government agencies looking into it the next day. I mean,
there's incredible impact that original reporting is having. Now, I
(08:44):
think we have to be honest that it's hard to
maintain that trust with consumers and many people don't trust it,
but the IMPACT's still there.
Speaker 3 (08:52):
You know. It's interesting just because you were around when
I was in the earlier days. You were new to it.
But in that dot com moment, you know, I would
have emerging companies come to see me and say, Michael,
we're going public in thirty days. We need to build
a brand. And I used to say, oh, you're from
the build a brand in thirty days group. I guy, Yeah,
(09:13):
that's not exactly how it works. It takes time to
build a brand. You can't build a brand. I mean literally,
there were people who'd come in and go, no, no, no,
we're going public in a month. Oh yeah, it doesn't
work that way. And I used to have a round
cabinet better known as the trash can for the people
who said I need to build a brand in thirty
days today, I would submit to you you can build
a brand in a much shorter time than people think.
(09:34):
Because the speed of information and all of that or everything,
we know you can. What we also know is you
can destroy a brand three seconds. You don't need thirty days,
you need one second. You can destroy a brand. We've
seen that happen as well. But I want to marken
back to something and this is something that I introduced
into the marketplace a couple of months ago. It was
(09:56):
a word game that I played and I came up
with some words and they apply here, and I'd love
your speed round word association. I was kind of making
an analogy to a Larry David kurb Your Enthusiasm episode
where they talked about at a dinner party the need
for a middler, the person at the dinner party who
(10:16):
will get the conversation started the middler. I think in
our industry, somehow I got the job of being the
middler in a lot of instances to kind of stir
the conversation. So I said, Okay, if that's kind of
my job, if that's kind of my remit in the industry,
I have to come up with the sentences of the
words I was an English major that would enable me
(10:38):
to start a conversation. So I came up with what
I've characterized as media links, t's and c's. Give me
the t's trust, transparency, technology, talent, and transformation. You use
any of those words, and you used many of them already. Yeah, okay,
in this conversation, you've used the transformation, you've certainly used
(11:00):
the technology word. Talked about trust because we're talking about
disinformation and transparency. Where'd you get the information from? I
understand people don't give up their sources, but you're trying
to get to a transparency and then the sea words.
So I've given you the t's. The S words are content, commerce, culture, creativity, community,
(11:23):
and curation. And I can think of a lot of
those words that apply to the information. You're a curator.
You're curating the important information for your audience. Yep, you're
building a community. You are creative in the way you're
approaching it. You are delivering amazing content, and there's a
(11:44):
commerce side to your business as well, and you're marrying
the ability to drive commerce with the content that you're delivering.
I know that sounds kind of trite, but it's true.
So i'd love you to pick any of those words
and come back to me with that in this comment.
Speaker 2 (12:00):
Well, I'd love to pick the tea that I didn't say,
or any Michael, which of course you're so sharp for
pointing out, which is talent And I actually think one
of the things I'm most proud of. You know, we
have more than thirty five journalists who come to us
from the Wall Street Journal, the Times, Bloomberg what they
think are their dream jobs, and they come here and
(12:22):
you know, do the best work of their career because
I think as a journalist inside a big newsroom, I
was really have been trying to focus on ways to
set up today's news talent for success. And this obviously
sends to our business side as well. And we're fortunate
we just hired our first chief commercial officer, Carl Wells,
who ran all of subscriptions for all of Dow Jones.
(12:45):
So I think talent in this moment also is incredibly important.
It's really the oxygen for everything we do, whether it's
you know, break the latest news about how many Twitter
Blue subscribers there are very top of mind this moment,
or you know, really getting the big story inside the
downfall of SVB and so on. So that word resonates
(13:08):
with me a lot. And I think sometimes in news
and media, when we think of talent, we think of
very flashy personalities who maybe lead with maybe a point
of view, and we think less of these kind of
hard nosed, facts driven journalists. But at the Information we
we have a deep bench of talent, and I'm constantly
(13:29):
thinking about how to make this an even better place
for our talent and so on.
Speaker 3 (13:35):
And let's think about that for a second. There's not
a market that doesn't have competition, but it seems like
your market is getting more competition some ways. In some ways,
whether it's what the Smith Boys did with Semaphore or
what Finkelstein and Beckmann are doing with you know, their
new venture, how do you see those as differentiated? Because
(13:57):
I do want to get into that, because you know,
there's another part of this conversation, Jess, that I want
to get to, which is the brand side of it,
because I have a view of how brands are trying
to stay away from news. Yes, we feel so strongly
that news is a great place for brands to reach.
You know, a whole other side of this conversation, a
(14:18):
very desirable audience in the context of news. Yet news
is a red flag to certain people. Yeah, we can
pull that thread back.
Speaker 2 (14:26):
But yeah, I love the question about competition. And you know,
I am a very happy investor in Semaphore and in
about half a dozen other news publications because man, our
industry needs new blood and new approaches, and I'm happy
to support it. But what makes the information, I think
different in addition to our journalism, is the community and
(14:48):
audience we've built around it.
Speaker 3 (14:49):
You know, community, there's one of my c words.
Speaker 2 (14:52):
Yeah, I mean, we have a tremendous number of you know,
hundreds of thousands of readers who were spending you know,
nineteen minutes per session. You know, who are coming back,
you know, opening the app, you know, dozens of times
a day. These are professionals really about half work in
tech and half don't, so really broader business professionals, leaders
(15:17):
and sort of all rungs at the ladder, who are deeply,
deeply engaged with the information. You know, they aren't just
clicking on a link they may see across social media.
They are coming to us to learn, for answers, to
be informed. And you know, our audience also excues decades
younger than the other business publications out there with I
(15:38):
think it's about two thirds to a quarter being you know,
mid forties and under, which is a unique audience. And
so I think for anyone, for brands, for other types
of partners, you know, we're unique in that regard, and
I think we have this engine of journalism that continues
(15:59):
to build that loyalty and relationship. But I'm really proud
of the real community. We built a community that also
convenes and you know, we just had a call for
our subscribers and Larry Summers to unpack the unfolding SVB
banking crisis, and you know, we're just jumping on zoom
asking Larry Summers questions.
Speaker 3 (16:18):
There's a great segue because you talk about that community SVB,
you know, Silicon Valley Bank. They are critically important, were
a critically important member of the community that we're talking
about here in terms of tech and you know your
reporting was where I went for the information. Let me
just be clear, not only for the information, but for
(16:41):
the information. I went to you because I knew it
would be the best reporting. But that had to be
really an important moment for your audience just because of
the tech side of it, even though that is not
the limit of your audience.
Speaker 2 (16:55):
Yeah, and I think we were able to lead on
that story, on the down fall of FTX and many
others because we have our ears to the ground. It's experience,
it's knowing whom to call. And you know, we're other
community in many ways, but that doesn't mean we're easy
on this community.
Speaker 3 (17:14):
And I think that's a really really important point. You're
not sickophantic to this community, but you're connected to the community.
You know what I learned, and you were one of
the people who taught me this, so I'm going to
give you back thank you for something you taught me
many years ago. I learned from professionals like you, and
(17:35):
I mean this that when you're dealing with a reporter
in their day job, they are not your friend. That
being said, you can be friendly, of course. Yeah, you know,
that's advice I give people all the time when dealing
with the proper members of the fourth Estate, if you.
Speaker 2 (17:51):
Will, yeah, no, And I think the other way I
think about that too, is that everyone's professional and understands
they have a job to do and also taking a
lot view in terms of building relationships and right now
Sam Altman, the CEO of Open Ai, is very much
in the news. I love the Journal in the time,
seemed to have done the story we did eighteen months
(18:12):
ago on him in the past few days. But I
first met Sam when he was still in Stanford trying
to get attention for a tiny mobile startup he was
launching called Looped And I was the only one with
nothing to do that day at the Wall Street Journal
and took the meeting. And I think, you know, being
able to have built relationships right where you know where
(18:32):
to go, and you know, back to Silicon Valley Bank,
I was really proud that we were the first to
point out that not only were venture funds sort of
consolidated in terms of their banking and their deposits being
at SVB, but SVB was a major investor in their
venture funds. And I think, you know, that was a
story we did that has tremendous significance and I expect
(18:56):
to come up in all the looking back about what
went wrong there, And that was a very classic kind
of story for us that we could really lead on.
Speaker 3 (19:05):
So, Jess, I want to flip to the brand side
of the business. Yes, I go back to you know,
the hard charge politics in our world right now has
made news more suspect for brands, like do I want
to be associated with news? Yes? I know that's where
the eyeballs are, But do I want my brand associated?
And this goes right to the brand safety issue that
(19:26):
you covered brilliantly when that was an issue for the platforms.
You know, the truth is brands need to be associated
with news. That's the advice I give them. If you
want to reach the consumer that you're desperate to reach,
that holy grail. Talk about that from how you absolutely yeah,
And to make a brand feel like they're not choosing
(19:48):
sides they don't want to be. You know, in this world,
I still believe you, it's okay to choose sides, by
the way, just so I can have my opinion out there.
But brands have to be nervous about that. And we're watching,
just as an example, we're watching this back and forth
now with Disney and Florida. So now it's getting back
to he said, she said, you did this, you did that.
(20:10):
You're picking on us. It's a news cycle, but yet
it's exactly there. You know, Disney's point. Bob Iger's point
was Disney is entitled to have an opinion just like
anybody else, and it shouldn't be something that requires punishment
from the government, is really what he was saying.
Speaker 2 (20:26):
I mean, it's a hugely important to show. I tell
you my partnerships with brands, and you know, we're so
fortunate to work for everyone from Apple to Accenture. I
mean we it's been really incredibly energizing to see how
we can kind of open up our community of subscribers
to partners and then come to us for a reason.
They want to reach decision makers, to build relationships with
(20:50):
them over you know, sometimes for a specific campaign or objective,
but really to build relationships over time and to influence
people who are going to you know, be very important
clients and partners to them over the long term.
Speaker 3 (21:04):
And Jess, you know, I'm a baseball guy. When I
grew up, I played baseball and it was my sport.
Not so much today, but back then, and I was
one of those walking encyclopedias because I knew every fact
in every detail. And there's a famous baseball player named
we Willie Keeler who was in the twenties or thirties,
and his tagline was hit him where they ain't. And
(21:28):
my argument to brands is, if you want to hit
them where they ain't, that's great. But if you want
to hit them where they are, and hit them where
they are in the right mentality, in the right mode,
where they're seeking information, I.
Speaker 2 (21:40):
Think that's a key. And we're all so different, you know,
I can't speak for sort of a generalist news publication
whose mission is just to cover all the facts of
the day, good or bad, right, I think that can
be more complicating for brands. You know, what we are
is we are a resource to be, you know, to
go into that next meeting and know what the heck
is how in the digital ad market or who's really
(22:03):
up or down inside Google at the moment. And I
think the relationship our readers have with us, they put
us in this sort of you know, secret weapon, although
we're not so secret anymore that everyone's reading us, but
we're a resource. We're there to help them solve problem.
Speaker 3 (22:18):
Well. I will tell you, Jessica that Ben King and
Andrew Cohene, my current and former chief of Stuff, can
tell you how many times my briefs for the day's
meetings have the information as the source for the information
that I'm getting so I can tell you that firsthand,
they are both shaking their heads to say, thank you,
you make their job easier.
Speaker 2 (22:39):
Well, well, that's what we love. And so I think
when it comes to the brands we work with, it's
how can we help you a brand, you know, reach
some people in this community, build these relationships yourself to
drive your business forward. And I do think that publications
that want to build very meaningful partnership businesses in the
(23:00):
coming decades, as we do, you know, need to sit
more on that side as solving real problems for the
partners as well as our audience. And I think when
you can do that, there's a tremendous opportunity because to
your point, there's so much consumer engagement, but you know,
long gone or the days of just thinking you're going
to throw something up and get some eyeballs and that's
(23:21):
going to work for anyone. And so I think, you know,
with our partnerships, we've really work to craft everything from
e bank components to surveys, to white papers to conversations
and you know, really build our programs off you know, newsletters,
so many things. It's really fun to be working with
brands right now.
Speaker 3 (23:40):
So Jessica, I want to come back to something that
is dear and dear to your heart and as well
to mine. We talked about talent, but you know, the
other subset of that is is the need for diversity
and talent. And number one and number two an area
that I know is near and dear to your heart
and certainly to mine, is you know, the entrepreneurial side.
(24:02):
And you know from a gender perspective, the opportunities for
women entrepreneurs. And you know I can speak to this
firsthand because my daughter in law was a entrepreneur who
was the co founder of the Wing. I think know that,
of course, and you know I watched what she went
through as a young founder. Did my best to be
a you know, not a mix in father in law,
(24:25):
but give her as much advice as I could. But
I watched some of the things she went through, good, bad,
and indifferent, building a business from a back of an
envelope to a business that reached a very high point.
Speaker 2 (24:37):
Absolutely, ecuation and.
Speaker 3 (24:38):
All of that and then combination of pandemic and other
things got in the way. But I watched the difficulty
that a young woman entrepreneur went through that I don't
think a young male entrepreneur would go through. I just don't.
I've been around the block enough to say.
Speaker 2 (24:53):
Yeah, I don't either, Michael. I agree with you. I mean,
I think there's are there horrible female founders, of course,
you know, but I think there's no question that the
world sees women in leadership in general, let alone at
the helm of a hot startup like the Wing or
I suppose the Information or other places you know differently,
(25:16):
And I think, you know, there is a lot. We
have a huge women event coming up this fall, and
so I'm in a phase of assembling data as we
look out ten years almost in the history of the information,
what has and hasn't changed for women in technology and business.
And I tell you, Michael, very little has changed.
Speaker 3 (25:35):
And I agree again, Jessica, you know I watched it firsthand. Yeah,
I must tell you it was painful to see some
of the extra difficulty that they encountered, not just my
daughter in law, but her and her co founder that
I don't think men would have encountered. They weren't less
(25:56):
equipped to handle it any means, but yeah, but they
were handling things that I would never have had to handle.
Speaker 2 (26:04):
And I think that's true you know, I know the
female experience. That's true for other underrepresented groups in tech
for sure, and across the board and in business. And
I think it's a time where we have to be
aware of it and we have to find ways to
build up and support, you know, the people who were
stepping out there to do things. I also think if
you look at women in technology, it's a moment. It
(26:27):
feels like a changing of the guard. To me, we're
seeing a lot of women step aside switch their roles
who have been great leaders in technology, like Sheryl Sandberg,
Susan Wijiski, and I think there's a question. I see
a lot of amazing women rising through the ranks, but
not all of them are as visible or want to
be as visible. And this is something else I think
(26:49):
I'm trying to understand and maybe slightly champion to be
a little more visible, because I do think seeing role
models makes a big difference.
Speaker 3 (26:58):
Well, it's what they did with c or the initiative,
which was so logical because the tagline, if you remember,
was you have you can't be her if you can't
see her, and that mentality works if you can't envision
yourself somewhere you're never going to get there. Yeah, able
to form that mental picture and say I can do.
Speaker 2 (27:16):
That, Yeah, absolutely, But this flip side, you know, I
think for women who want to be you know, who
are in the trenches, like they had their work cut
out for them to just be badass at their job
right without taking all the time. So it's kind of
you know, I have three boys under the age of six,
it's you know, I'm optimistic, and I personally just want
(27:40):
myself and the information to kind of be ahead of
those stories, to be telling them to push back. You know,
early on in our history, one of the first big,
big stories we broke was about a venture capitalist who
was sexually harassing female founders, and you know, that story
ended up shuttering his f and we continued on the
(28:01):
thread and really launched the me too movement in Silicon
Valley right before Hollywood. And I just don't think that
was it was not a story other publications covered, but
it was when we covered, and so it's an important
part of our DNA.
Speaker 3 (28:15):
Well, Jessica Lessen, this has been an important part of
my day, my week. To be able to have somebody
as bright as you and as articulate as you share
your thinking and your thoughts and your vision. I want
to thank you. We could go on forever, Jess, but
we've covered a lot. I appreciate it. I do want
(28:37):
to schedule a second round with you, because there's so
much more I want anytime.
Speaker 2 (28:41):
I think everyone in our industry should just hold on tight,
Michael and buckle up because a lot of changes coming
and so it's really fun to unpack it with you.
Thank you for having me.
Speaker 3 (28:56):
I'm Michael Cassen. Thanks for listening to Good Company.
Speaker 1 (29:01):
A Good Company is a production of iHeartRadio. A special
thanks to Lena Peterson, chief Brand Officer and Managing Director
of media Link, for her vision on Good Company, and
to Jen Sealey, vice President Marketing Communications of media Link
for programming amazing talent and content
Good Company is a production of iHeartRadio.
Speaker 2 (00:03):
I really realized that business readers were not being well
served by the present state of business coverage.
Speaker 3 (00:15):
Hi, I'm Michael Casson. Welcome to Good Company. We're all
explore how marketing, media, entertainment and tech are intersecting, transforming
our lives and the way we do business at a
breakneck speed. I'll be joined by some of the greatest
business minds at strongest leaders who will share how they
built companies from the ground up or transformed them from
the inside out. My bet is you'll pick up a
(00:37):
lesson or two along the way.
Speaker 2 (00:38):
It's all good.
Speaker 3 (00:44):
Today, I have the great pleasure of speaking with a
very longtime friend, Jessica Lesson. Jessica is the founder and
the CEO of The Information and importantly, Jessica founded The
Information in twenty thirteen as an early player really in
building the next kind of leading business news publication and
(01:05):
since then, I'm proud to say I've been a regular
reader since the beginning. But I would think I submit
this to our listeners, but I think it's true in
our business in the way I describe our business, kind
of the intersection of marketing, media, advertising, entertainment, sports and technology.
Kind of think the information lives at that same intersection.
(01:25):
I think it's a must read. I kind of think
if you're not up to date, you don't have the information,
you're not going to be as up to date as
you need to be. So, Jessica, it's great to welcome
you to good company.
Speaker 2 (01:37):
Thank you so much for having me.
Speaker 3 (01:38):
Michael Jessica, I want to give a little bit of
a shout out to the fact that it's fun for
me to be having an interview with you, because for
so many years when you and I first met, when
you were at the Wall Street Journal, you got to
interview me.
Speaker 2 (01:52):
I was growing you all the time. Yeah, so no,
it's nice when the tables turn and I get to
put down the notebook.
Speaker 3 (01:58):
So well, there you go. You've had a remarkable career.
And again, when you were a journalist at the Wall
Street Journal and I was in the middle of some
important stories that you were following, I can say this
with my right hand to God, you were as good
as it gets in terms of getting to the point,
getting to the facts, and really not letting anybody off
easy in a good way, in a respectful way. I'd
(02:20):
love it if you could give our audience a little
bit of walk down kind of you know, Jessica's road
to today. You know, even before founding The Information in
twenty thirteen, well.
Speaker 2 (02:32):
I think I caught not just the journalism bug, but
kind of the technology journalism bug actually in college, and
you know, I was watching a new generation of founder
and entrepreneur build tech businesses and realizing that, you know,
these were going to be really important businesses Facebook, Twitter,
(02:52):
what was happening at Google? And got lucky enough to
join the Wall Street Journal out of college, where no
one wanted to cover those companies. I had an editor
tell me, you know, oh, Facebook, how are they going
to make money?
Speaker 3 (03:05):
And to me it had an investment advisor say to
me Amazon, They'll never make money.
Speaker 2 (03:10):
Yes, plenty of those stories and you know where people
saw like young kids and ping pong balls in their office.
I really thought this was the future business. Every industry
is going to be transformed by what's being built in technology.
Great tech companies will be built, but everything is going
to be changed. And over the course of covering those
(03:33):
companies at the Wall Street Journal, I really realized that
business readers were not being well served by the present
state of business coverage, which to me was not looking ahead.
It was not realizing that P ANDNG is, you know,
rethinking everything about its business and you know, becoming an
(03:55):
experting Google as much as the next business to acquire customers.
And so just.
Speaker 3 (04:00):
It's interesting because you and I talked about this back
then we had begun to work for Salesforce. I want
to remind you of this. And what Mark Benioff had
said to me back then was Michael. I interviewed him
at a keynote for CS I think you were probably there.
Speaker 2 (04:15):
Yep, that rings them hell for sure.
Speaker 3 (04:16):
Yeah, I think it was twelve years ago. And I
interviewed him and then he turned to me and said, Michael,
I want to interview you with my sales team. And
I said, why is that? He said, because I built
a company at that point twelve years ago on the
back of cloud computing, and now I'm making this foray
into the marketing cloud, and I need to understand how
(04:37):
to reach the marketer and not the IT person, because
cloud computing would have gone through the door of IT,
marketing cloud would go through the door of CMO. And
you might remember this. We came up with this view
that the CMO and the CTO were becoming one and
the same in many companies because a technology or just
(05:00):
to your point of Procter and Gamble as a for instance,
the chief technology officer at Procter and Gamble has to
know more and more today about marketing, and the chief
marketing officer has to know more and more about technology.
And so I used to kid around and say, the
person with the pocket square is now the same as
the person with the pocket protector hoodie.
Speaker 2 (05:23):
Michael, we liked refer to hoodies exactly, it's not as nerdy.
But no, and everywhere I looked, you know who was
joining the board of Disney, it was Sheryl Sandberg and
Jack Dorsey. And so when I thought of building a
business publication that you know, could build on what the
Journal and the Ft and Bloomberg have accomplished and the
readers they serve, but serve them for the next fifty years,
(05:46):
it was clear to me there was a big opportunity there,
both in terms of areas of expertise of reporting and
coverage and then also of course business model by kind
of starting with a very passionate subscription core. So, yeah,
after eight years at the journal I decided to take
the plunge and start the information, and now we're nine
(06:06):
and a half years.
Speaker 3 (06:07):
In its unbelieved.
Speaker 2 (06:09):
Hundreds of thousands of readers. So it's a little crazy.
Speaker 3 (06:13):
You've been a fierce advocate, both in your just pure
journalistic role but also now your entrepreneurial role, if you will,
of the facts and been a fierce advocate of dispelling
misinformation and really kind of getting to the truth whatever
that you know, I'm funny about that. I think truth
(06:33):
is still a word that can be defined. I don't believe.
I don't want to be political, but I don't believe
in alternative facts. I think that there are just facts
and there are truths, and I think you do as well.
But we're in a world where that doesn't seem to
be everybody's view. Any advice that you can give on
how you stay pure and so committed to that at
(06:55):
a time when it feels like that's a bit of
you know, multiple choice to people maybe is to say.
Speaker 2 (07:02):
It it's an incredible time, and then you add Michael,
you add Ai into this, honestly, And someone came to
me yesterday or a couple of days ago and said,
so you're going to hire a thousand reporters to like
be able to fact check, you know, what coat the
pope is wearing, or just as an example, because there
are memes out there, you know, now with AI you
can really distort reality. So for me, I answer that
(07:24):
question with the reporting process. I have a lot of
faith in who did we talk to, what did they say?
Is it verified? How does the person who told us something? No.
I'm constantly asking how does that person know?
Speaker 3 (07:38):
Right?
Speaker 2 (07:39):
And I think I am a little old school about that,
but I think even in a world where journalists are
only going to be contributing a small sliver to the
overall information ecosystem, that sliver is really really important. And
you know, that's the part of the problem I want
to work on, which is to ensure that continues to
(08:00):
be high quality, original reporting, that is accurate, and that is,
you know, as much as possible, tuning out the noise
and getting back to the basics of sort of what
do we know and how do we know it. I
think as a society we're gonna disinformation we've only we
haven't even scratched the surface of what's coming. But I
(08:22):
am optimistic because we are seeing massively engaged audiences for
quality journalism when it's introduced, and you know, we can
write a story about a troubled startup and you know,
government agencies looking into it the next day. I mean,
there's incredible impact that original reporting is having. Now, I
(08:44):
think we have to be honest that it's hard to
maintain that trust with consumers and many people don't trust it,
but the IMPACT's still there.
Speaker 3 (08:52):
You know. It's interesting just because you were around when
I was in the earlier days. You were new to it.
But in that dot com moment, you know, I would
have emerging companies come to see me and say, Michael,
we're going public in thirty days. We need to build
a brand. And I used to say, oh, you're from
the build a brand in thirty days group. I guy, Yeah,
(09:13):
that's not exactly how it works. It takes time to
build a brand. You can't build a brand. I mean literally,
there were people who'd come in and go, no, no, no,
we're going public in a month. Oh yeah, it doesn't
work that way. And I used to have a round
cabinet better known as the trash can for the people
who said I need to build a brand in thirty
days today, I would submit to you you can build
a brand in a much shorter time than people think.
(09:34):
Because the speed of information and all of that or everything,
we know you can. What we also know is you
can destroy a brand three seconds. You don't need thirty days,
you need one second. You can destroy a brand. We've
seen that happen as well. But I want to marken
back to something and this is something that I introduced
into the marketplace a couple of months ago. It was
(09:56):
a word game that I played and I came up
with some words and they apply here, and I'd love
your speed round word association. I was kind of making
an analogy to a Larry David kurb Your Enthusiasm episode
where they talked about at a dinner party the need
for a middler, the person at the dinner party who
(10:16):
will get the conversation started the middler. I think in
our industry, somehow I got the job of being the
middler in a lot of instances to kind of stir
the conversation. So I said, Okay, if that's kind of
my job, if that's kind of my remit in the industry,
I have to come up with the sentences of the
words I was an English major that would enable me
(10:38):
to start a conversation. So I came up with what
I've characterized as media links, t's and c's. Give me
the t's trust, transparency, technology, talent, and transformation. You use
any of those words, and you used many of them already. Yeah, okay,
in this conversation, you've used the transformation, you've certainly used
(11:00):
the technology word. Talked about trust because we're talking about
disinformation and transparency. Where'd you get the information from? I
understand people don't give up their sources, but you're trying
to get to a transparency and then the sea words.
So I've given you the t's. The S words are content, commerce, culture, creativity, community,
(11:23):
and curation. And I can think of a lot of
those words that apply to the information. You're a curator.
You're curating the important information for your audience. Yep, you're
building a community. You are creative in the way you're
approaching it. You are delivering amazing content, and there's a
(11:44):
commerce side to your business as well, and you're marrying
the ability to drive commerce with the content that you're delivering.
I know that sounds kind of trite, but it's true.
So i'd love you to pick any of those words
and come back to me with that in this comment.
Speaker 2 (12:00):
Well, I'd love to pick the tea that I didn't say,
or any Michael, which of course you're so sharp for
pointing out, which is talent And I actually think one
of the things I'm most proud of. You know, we
have more than thirty five journalists who come to us
from the Wall Street Journal, the Times, Bloomberg what they
think are their dream jobs, and they come here and
(12:22):
you know, do the best work of their career because
I think as a journalist inside a big newsroom, I
was really have been trying to focus on ways to
set up today's news talent for success. And this obviously
sends to our business side as well. And we're fortunate
we just hired our first chief commercial officer, Carl Wells,
who ran all of subscriptions for all of Dow Jones.
(12:45):
So I think talent in this moment also is incredibly important.
It's really the oxygen for everything we do, whether it's
you know, break the latest news about how many Twitter
Blue subscribers there are very top of mind this moment,
or you know, really getting the big story inside the
downfall of SVB and so on. So that word resonates
(13:08):
with me a lot. And I think sometimes in news
and media, when we think of talent, we think of
very flashy personalities who maybe lead with maybe a point
of view, and we think less of these kind of
hard nosed, facts driven journalists. But at the Information we
we have a deep bench of talent, and I'm constantly
(13:29):
thinking about how to make this an even better place
for our talent and so on.
Speaker 3 (13:35):
And let's think about that for a second. There's not
a market that doesn't have competition, but it seems like
your market is getting more competition some ways. In some ways,
whether it's what the Smith Boys did with Semaphore or
what Finkelstein and Beckmann are doing with you know, their
new venture, how do you see those as differentiated? Because
(13:57):
I do want to get into that, because you know,
there's another part of this conversation, Jess, that I want
to get to, which is the brand side of it,
because I have a view of how brands are trying
to stay away from news. Yes, we feel so strongly
that news is a great place for brands to reach.
You know, a whole other side of this conversation, a
(14:18):
very desirable audience in the context of news. Yet news
is a red flag to certain people. Yeah, we can
pull that thread back.
Speaker 2 (14:26):
But yeah, I love the question about competition. And you know,
I am a very happy investor in Semaphore and in
about half a dozen other news publications because man, our
industry needs new blood and new approaches, and I'm happy
to support it. But what makes the information, I think
different in addition to our journalism, is the community and
(14:48):
audience we've built around it.
Speaker 3 (14:49):
You know, community, there's one of my c words.
Speaker 2 (14:52):
Yeah, I mean, we have a tremendous number of you know,
hundreds of thousands of readers who were spending you know,
nineteen minutes per session. You know, who are coming back,
you know, opening the app, you know, dozens of times
a day. These are professionals really about half work in
tech and half don't, so really broader business professionals, leaders
(15:17):
and sort of all rungs at the ladder, who are deeply,
deeply engaged with the information. You know, they aren't just
clicking on a link they may see across social media.
They are coming to us to learn, for answers, to
be informed. And you know, our audience also excues decades
younger than the other business publications out there with I
(15:38):
think it's about two thirds to a quarter being you know,
mid forties and under, which is a unique audience. And
so I think for anyone, for brands, for other types
of partners, you know, we're unique in that regard, and
I think we have this engine of journalism that continues
(15:59):
to build that loyalty and relationship. But I'm really proud
of the real community. We built a community that also
convenes and you know, we just had a call for
our subscribers and Larry Summers to unpack the unfolding SVB
banking crisis, and you know, we're just jumping on zoom
asking Larry Summers questions.
Speaker 3 (16:18):
There's a great segue because you talk about that community SVB,
you know, Silicon Valley Bank. They are critically important, were
a critically important member of the community that we're talking
about here in terms of tech and you know your
reporting was where I went for the information. Let me
just be clear, not only for the information, but for
(16:41):
the information. I went to you because I knew it
would be the best reporting. But that had to be
really an important moment for your audience just because of
the tech side of it, even though that is not
the limit of your audience.
Speaker 2 (16:55):
Yeah, and I think we were able to lead on
that story, on the down fall of FTX and many
others because we have our ears to the ground. It's experience,
it's knowing whom to call. And you know, we're other
community in many ways, but that doesn't mean we're easy
on this community.
Speaker 3 (17:14):
And I think that's a really really important point. You're
not sickophantic to this community, but you're connected to the community.
You know what I learned, and you were one of
the people who taught me this, so I'm going to
give you back thank you for something you taught me
many years ago. I learned from professionals like you, and
(17:35):
I mean this that when you're dealing with a reporter
in their day job, they are not your friend. That
being said, you can be friendly, of course. Yeah, you know,
that's advice I give people all the time when dealing
with the proper members of the fourth Estate, if you.
Speaker 2 (17:51):
Will, yeah, no, And I think the other way I
think about that too, is that everyone's professional and understands
they have a job to do and also taking a
lot view in terms of building relationships and right now
Sam Altman, the CEO of Open Ai, is very much
in the news. I love the Journal in the time,
seemed to have done the story we did eighteen months
(18:12):
ago on him in the past few days. But I
first met Sam when he was still in Stanford trying
to get attention for a tiny mobile startup he was
launching called Looped And I was the only one with
nothing to do that day at the Wall Street Journal
and took the meeting. And I think, you know, being
able to have built relationships right where you know where
(18:32):
to go, and you know, back to Silicon Valley Bank,
I was really proud that we were the first to
point out that not only were venture funds sort of
consolidated in terms of their banking and their deposits being
at SVB, but SVB was a major investor in their
venture funds. And I think, you know, that was a
story we did that has tremendous significance and I expect
(18:56):
to come up in all the looking back about what
went wrong there, And that was a very classic kind
of story for us that we could really lead on.
Speaker 3 (19:05):
So, Jess, I want to flip to the brand side
of the business. Yes, I go back to you know,
the hard charge politics in our world right now has
made news more suspect for brands, like do I want
to be associated with news? Yes? I know that's where
the eyeballs are, But do I want my brand associated?
And this goes right to the brand safety issue that
(19:26):
you covered brilliantly when that was an issue for the platforms.
You know, the truth is brands need to be associated
with news. That's the advice I give them. If you
want to reach the consumer that you're desperate to reach,
that holy grail. Talk about that from how you absolutely yeah,
And to make a brand feel like they're not choosing
(19:48):
sides they don't want to be. You know, in this world,
I still believe you, it's okay to choose sides, by
the way, just so I can have my opinion out there.
But brands have to be nervous about that. And we're watching,
just as an example, we're watching this back and forth
now with Disney and Florida. So now it's getting back
to he said, she said, you did this, you did that.
(20:10):
You're picking on us. It's a news cycle, but yet
it's exactly there. You know, Disney's point. Bob Iger's point
was Disney is entitled to have an opinion just like
anybody else, and it shouldn't be something that requires punishment
from the government, is really what he was saying.
Speaker 2 (20:26):
I mean, it's a hugely important to show. I tell
you my partnerships with brands, and you know, we're so
fortunate to work for everyone from Apple to Accenture. I
mean we it's been really incredibly energizing to see how
we can kind of open up our community of subscribers
to partners and then come to us for a reason.
They want to reach decision makers, to build relationships with
(20:50):
them over you know, sometimes for a specific campaign or objective,
but really to build relationships over time and to influence
people who are going to you know, be very important
clients and partners to them over the long term.
Speaker 3 (21:04):
And Jess, you know, I'm a baseball guy. When I
grew up, I played baseball and it was my sport.
Not so much today, but back then, and I was
one of those walking encyclopedias because I knew every fact
in every detail. And there's a famous baseball player named
we Willie Keeler who was in the twenties or thirties,
and his tagline was hit him where they ain't. And
(21:28):
my argument to brands is, if you want to hit
them where they ain't, that's great. But if you want
to hit them where they are, and hit them where
they are in the right mentality, in the right mode,
where they're seeking information, I.
Speaker 2 (21:40):
Think that's a key. And we're all so different, you know,
I can't speak for sort of a generalist news publication
whose mission is just to cover all the facts of
the day, good or bad, right, I think that can
be more complicating for brands. You know, what we are
is we are a resource to be, you know, to
go into that next meeting and know what the heck
is how in the digital ad market or who's really
(22:03):
up or down inside Google at the moment. And I
think the relationship our readers have with us, they put
us in this sort of you know, secret weapon, although
we're not so secret anymore that everyone's reading us, but
we're a resource. We're there to help them solve problem.
Speaker 3 (22:18):
Well. I will tell you, Jessica that Ben King and
Andrew Cohene, my current and former chief of Stuff, can
tell you how many times my briefs for the day's
meetings have the information as the source for the information
that I'm getting so I can tell you that firsthand,
they are both shaking their heads to say, thank you,
you make their job easier.
Speaker 2 (22:39):
Well, well, that's what we love. And so I think
when it comes to the brands we work with, it's
how can we help you a brand, you know, reach
some people in this community, build these relationships yourself to
drive your business forward. And I do think that publications
that want to build very meaningful partnership businesses in the
(23:00):
coming decades, as we do, you know, need to sit
more on that side as solving real problems for the
partners as well as our audience. And I think when
you can do that, there's a tremendous opportunity because to
your point, there's so much consumer engagement, but you know,
long gone or the days of just thinking you're going
to throw something up and get some eyeballs and that's
(23:21):
going to work for anyone. And so I think, you know,
with our partnerships, we've really work to craft everything from
e bank components to surveys, to white papers to conversations
and you know, really build our programs off you know, newsletters,
so many things. It's really fun to be working with
brands right now.
Speaker 3 (23:40):
So Jessica, I want to come back to something that
is dear and dear to your heart and as well
to mine. We talked about talent, but you know, the
other subset of that is is the need for diversity
and talent. And number one and number two an area
that I know is near and dear to your heart
and certainly to mine, is you know, the entrepreneurial side.
(24:02):
And you know from a gender perspective, the opportunities for
women entrepreneurs. And you know I can speak to this
firsthand because my daughter in law was a entrepreneur who
was the co founder of the Wing. I think know that,
of course, and you know I watched what she went
through as a young founder. Did my best to be
a you know, not a mix in father in law,
(24:25):
but give her as much advice as I could. But
I watched some of the things she went through, good, bad,
and indifferent, building a business from a back of an
envelope to a business that reached a very high point.
Speaker 2 (24:37):
Absolutely, ecuation and.
Speaker 3 (24:38):
All of that and then combination of pandemic and other
things got in the way. But I watched the difficulty
that a young woman entrepreneur went through that I don't
think a young male entrepreneur would go through. I just don't.
I've been around the block enough to say.
Speaker 2 (24:53):
Yeah, I don't either, Michael. I agree with you. I mean,
I think there's are there horrible female founders, of course,
you know, but I think there's no question that the
world sees women in leadership in general, let alone at
the helm of a hot startup like the Wing or
I suppose the Information or other places you know differently,
(25:16):
And I think, you know, there is a lot. We
have a huge women event coming up this fall, and
so I'm in a phase of assembling data as we
look out ten years almost in the history of the information,
what has and hasn't changed for women in technology and business.
And I tell you, Michael, very little has changed.
Speaker 3 (25:35):
And I agree again, Jessica, you know I watched it firsthand. Yeah,
I must tell you it was painful to see some
of the extra difficulty that they encountered, not just my
daughter in law, but her and her co founder that
I don't think men would have encountered. They weren't less
(25:56):
equipped to handle it any means, but yeah, but they
were handling things that I would never have had to handle.
Speaker 2 (26:04):
And I think that's true you know, I know the
female experience. That's true for other underrepresented groups in tech
for sure, and across the board and in business. And
I think it's a time where we have to be
aware of it and we have to find ways to
build up and support, you know, the people who were
stepping out there to do things. I also think if
you look at women in technology, it's a moment. It
(26:27):
feels like a changing of the guard. To me, we're
seeing a lot of women step aside switch their roles
who have been great leaders in technology, like Sheryl Sandberg,
Susan Wijiski, and I think there's a question. I see
a lot of amazing women rising through the ranks, but
not all of them are as visible or want to
be as visible. And this is something else I think
(26:49):
I'm trying to understand and maybe slightly champion to be
a little more visible, because I do think seeing role
models makes a big difference.
Speaker 3 (26:58):
Well, it's what they did with c or the initiative,
which was so logical because the tagline, if you remember,
was you have you can't be her if you can't
see her, and that mentality works if you can't envision
yourself somewhere you're never going to get there. Yeah, able
to form that mental picture and say I can do.
Speaker 2 (27:16):
That, Yeah, absolutely, But this flip side, you know, I
think for women who want to be you know, who
are in the trenches, like they had their work cut
out for them to just be badass at their job
right without taking all the time. So it's kind of
you know, I have three boys under the age of six,
it's you know, I'm optimistic, and I personally just want
(27:40):
myself and the information to kind of be ahead of
those stories, to be telling them to push back. You know,
early on in our history, one of the first big,
big stories we broke was about a venture capitalist who
was sexually harassing female founders, and you know, that story
ended up shuttering his f and we continued on the
(28:01):
thread and really launched the me too movement in Silicon
Valley right before Hollywood. And I just don't think that
was it was not a story other publications covered, but
it was when we covered, and so it's an important
part of our DNA.
Speaker 3 (28:15):
Well, Jessica Lessen, this has been an important part of
my day, my week. To be able to have somebody
as bright as you and as articulate as you share
your thinking and your thoughts and your vision. I want
to thank you. We could go on forever, Jess, but
we've covered a lot. I appreciate it. I do want
(28:37):
to schedule a second round with you, because there's so
much more I want anytime.
Speaker 2 (28:41):
I think everyone in our industry should just hold on tight,
Michael and buckle up because a lot of changes coming
and so it's really fun to unpack it with you.
Thank you for having me.
Speaker 3 (28:56):
I'm Michael Cassen. Thanks for listening to Good Company.
Speaker 1 (29:01):
A Good Company is a production of iHeartRadio. A special
thanks to Lena Peterson, chief Brand Officer and Managing Director
of media Link, for her vision on Good Company, and
to Jen Sealey, vice President Marketing Communications of media Link
for programming amazing talent and content
Popular Podcasts
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The Nikki Glaser Podcast
Every week comedian and infamous roaster Nikki Glaser provides a fun, fast-paced, and brutally honest look into current pop-culture and her own personal life.