What's up, everybody?
This is Cortland from IndieHackers.com, and you're listening to the IndieHackers podcast.
On this show, I talk to the founders of profitable internet businesses, and I try to get a sense
of what it's like to be in their shoes.
How did they get to where they are today?
How did they make decisions, both through their companies and in their personal lives,
and what exactly makes their businesses tick?
And the goal here, as always, is so that the rest of us can learn from their examples and
go on to build our own profitable internet businesses.
If you've been enjoying the show and you want an easy way to support it, you should leave
a review for us on iTunes.
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review.
There's been a lot said on this podcast about how if you want to build a business that makes
enough money for you to quit your job and be your own boss, it's helpful to build an
audience first.
And recently, that's gone a step further, and to actually don't just build an audience,
build an entire media company, a media brand.
I think that's obviously the most extreme version of building an audience.
So instead of just talking to amateurs about this, I wanted to talk to a pro, someone who's
actually done this and gotten paid to do it as their job.
Alex Wilhelm is the senior editor at TechCrunch.
He was also the editor-in-chief at Crunchbase News, which he started from scratch.
And it's worth listening to Alex's experiences and advice because he knows what it's like
to build one organization that drives millions of page views, rather than more simpler content
marketing efforts that only get a few hundred or a few thousand page views here and there.
At the end of the episode, we tried to distill Alex's advice into a bullet list or playbook
of sorts that you can follow.
But I really recommend listening to him elaborate on each of these principles during our conversation,
just because I think that's a much better way to really understand what he's getting
at.
Enjoy the conversation.
I know you've had at least two different stents where you were charged with building
an entire media organization from scratch, one at Mattermark and one at Crunchbase News.
That's a huge responsibility.
And I know also they turned out very differently.
So let's start with Mattermark.
What was going through your head when they gave you that huge responsibility, and how
did you approach it?
Going to Mattermark was interesting.
It's a little bit of a personal story, more than a work story.
I was at TechCrunch before Mattermark, and I had a little bit of a drinking problem.
And so I thought that I was miserable in my job, it turns out I was just miserable in
life.
So I quit TC, I went to Mattermark.
And the idea was, like you said, it was to build a little media company, led by me, kind
of focused on my financial start-up-y venture capital type stuff, kind of my bread and butter
that I've written about for a while.
And it went medium bad until I went to rehab, and then it went medium good until I quit.
It's kind of the breakdown of 2016 for me.
Mattermark didn't, in the end, have the resource base required to do what our ambitions wanted.
And that's kind of a, that's not a diss in any way.
Start-ups are always resource constrained, you're always making priorities.
And so as Mattermark's business didn't quite proceed the way that we had anticipated, my
resource base kind of got diminished until the point when it's kind of like, okay, this
is not going to work.
But I sure learned a lot.
I mean, as a personal year, huge, in terms of just learning a lot of stuff, getting my
life back together, getting my health back together, and all that stuff.
So it was super useful as a year, a tough one, though, not one that I would be super
excited to do again.
It's one of those formative years where you learn a lot about yourself.
Yeah, you know, I really hate how most of life is falling down a staircase and learning
how to fall down better the next time, but it seems to be a trend, at least in my life.
What I'll say the way is, if you've never worked at a start-up, it's a really interesting
environment and there's nothing quite like it, given the sheer lack of rules and kind
of like formality.
And so for me, going from TC, which was owned by AOL effectively when I was there, and then
now Verizon.
So inside the belly of a huge company, right, Portland, I mean, it's just huge.
And going to Mattermark, when you could see the whole company in one room was just insane
to me.
Like, you could see everybody.
Like, where's sales?
Oh, right there.
You know, where's legal?
Oh, it's that person.
You know, like, it's this strange place.
So it was also a really good intro for me to kind of the world of in the guts start-up.
I got to go to a board meeting and I got to kind of do that in the weed stuff.
And so I just tried to absorb as much as I could, because it was a great, great experience.
I think everyone should work for a startup for at least a year to see what they're like.
You know, like, it's just so different.
And if you're a solo founder, you're literally wearing all the hats.
Where's legal?
It's you.
Who's on content?
It's you.
Who's building the product?
It's you.
Yeah.
What did you take from your time at TechCrunch going to Mattermark?
I mean, TechCrunch, as you said, it was owned by AOL.
They've been doing this for a long time.
When you showed up at Mattermark, were you like, wow, you guys are doing content all
wrong.
Here are the things you need to fix.
Well, no.
So they had some good stuff going for them.
So one, the CEO of Mattermark, Danielle Morrell, is a mastermind of generating attention around
things.
She can just engender attention to what she's working on.
So she was always very good at writing up posts about Mattermark's business, growth at
the time, drawing a lot of attention to that.
There was a newsletter that was doing really well, frankly, and there was a guy named Nick
who was running that.
Love, Nick.
Fantastic human.
They had some kind of bones in place.
But what they didn't have, though, was someone who was focused on it kind of full time, someone
who was going to bring a different tone to it, frankly, just a journalistic tone.
My goal was to come there, go there, and build a reputable, if small, journalistic outlet.
That was the idea.
And it's hard to do that if you don't have some grounding in journalism because a lot
of business relationships are relatively transactional, whereas a lot of journalism isn't.
And so it's hard to kind of jump over that fence if you're not accustomed to what it's
like on the other side.
But TC was interesting.
I guess, narrow that for me a little bit because I could ramble it for 20 minutes and bore
the hair out of you.
What do you want me to focus on?
I mean, strategically, one of the things that I see is setting journalism apart and sort
of news content as opposed to a lot of the content that most founders write is just the
tremendous amount of attention and traffic that you can generate by telling people what's
going on in the world.
For example, you've got something like 75,000, 80,000 followers on Twitter.
And it's not just you.
You've got other journalists and they all seem to have 10, 20, 30,000 followers, way
more than the average founder.
And there's just something that seems to me about news that seems to be so good at captivating
people and getting them to read and follow and building an audience.
And so when you come into a place like Mattermark and they're saying, hey, we want a reputable
news outlet, how do you think about what you're going to do for them?
How are you going to actually get the numbers that they need?
Why do you need so many resources?
Do you need to hire a team?
What is it that you're doing that gets you such a large audience?
So on the team front, I hired some people that I knew on kind of a contract part time
basis because that was the kind of budget that I had to play with.
So it was maximizing how much I could get for my set budget at the time.
So we're regarding the team front.
Journalism is largely a team sport.
You can do it solo, a bit like building a company, team sport, but often people will
actually be a solo founder, a little bit less common, I think.
But in journalism, you want to have someone who's good at copy editing, right?
So you don't have ridiculous small errors in your public, you know, facing work that
makes you lose credibility.
We ended up with a small team of someone who could help copy it and kind of run the site,
someone who was better at data journalism than me.
That was kind of our trio, if you will.
So it was a mixture of talents that we then tried to bring to the market.
Then coming kind of to the front part of your question about, you know, what was our plan?
One of the most obvious things in well-known facts was still least regarded piece of advice
when it comes to writing on the internet is regularity.
And the reason why everyone knows that it's true is because it works.
And the reason why no one does it is because it's hard.
And it's really, really hard to go out there and actually write every day, unless you've
done it forever.
Like, you know, this is my job.
So to me, it's kind of like what I do, but for most folks, it's difficult.
And so the team element comes into play there a little bit too, because you can have some
people to fall back on if you run out of ideas for a day.
You have someone else there who might have an idea of their own, they can kind of bring
it forward.
But with Matterwork, you know, it started off with just me.
Like I rolled in as the journalist.
There was no plural.
It was just me.
So then it was fun stuff like, you know, getting the blog set up and learning how to work with
the developer team and that sort of stuff.
For me, all this kind of new, informative experiences.
But the goal was to publish every day and we eventually got there and we got to cover
some relatively big stuff and we got better as time went too long and got better at, you
know, just having, you know, regular chart colors for branding's sake.
Stuff like that, that is pretty basically, you have to learn.
And it was a good year, but, you know, I don't think we accomplished there all that we wanted
to.
And that's why I was glad to kind of get another crack at the apple with Crunchbase News.
So let's talk about these aspects of journalism that make it work.
The first thing you identified is regularity.
I think the average founder who has a blog attached to their SaaS product or something
isn't that regular every now and then they publish once every month or so, then twice
in another month.
What are your strategies for sourcing content and ideas and being a regularly consistent
writer?
Well, one thing you mentioned a few minutes ago was how many followers journalists some
ones have on Twitter.
And I think that's not simply because they're journalists, I think because they're there
a lot.
And so, you know, one thing that people like myself in the media do is we just we read
constantly and we stay up too late and we read way too many tweets and articles and
papers and we watch too many interviews and we stay generally informed broadly and then
we niche down into our chosen vertical or focus area, if you will.
And I think that founders often end up in their own little world, which is what you'd
expect because they're building something, right?
They're focused on this one thing they're doing.
They're fixing, you know, they're fixing a problem with a SaaS product or they're trying
to develop this new brand or whatever.
Things that they get niched down.
And so it's not a surprise to me that it's hard to write a lot because if you're doing
one thing, you can only write somebody post attached to that one thing.
If you're in my seat, I cover, you know, the public markets to some degree, startups, venture
capital trends, you know, Austin startups.
There's a lot of stuff that's kind of brewing around.
So I always have something to grab onto.
So I think topic diversity might be a pretty good way around the writer's block that a
lot of people have, it seems, in the startup community when it comes to the stuff you're
talking about.
Again, I'm speaking from just my perspective to them, so this may be terrible advice.
I freely admit, but that's my take on it.
So widening their topic remit and then also getting friends to write for them if possible.
If they have friends that can write, having someone else contribute brings their audience.
It brings their social following for a couple of days.
It's a really brilliant way to kind of get the word out a bit more than you can by yourself.
Though, of course, you know, you can always beat your own drum as far as you want.
Yeah, it seems like if you broaden what you write about, suddenly the world is your oyster.
You can write about a ton more different things.
But it also doesn't necessarily mean that anyone actually cares what you're writing
about.
I've seen a lot of dead blogs, a lot of dead news organizations, or people writing stuff
and they just don't get the subscribers, they don't get the followers on Twitter.
How do you think about choosing which content people actually want to read?
Well, one thing that you have is a never-ending feedback loop of analytics.
Because when you publish something and you tweet it out, you get essentially instant
feedback.
Like you can see in the numbers if no one cares.
And I try to not let that guide me too much because I don't know how to phrase this without
swearing a lot.
But screw them, I'll write what I want is my perspective a lot of the time.
But also, I do work for a publication that works for a for-profit company so I have to
pay some attention to performance.
And so what I have noticed is you can just watch what people care about.
One thing that's blown my mind lately has been the interest in no and low-code solutions.
I did a tweet about no code and I got a dozen emails about it because people were like,
good.
It's great.
We want to talk to you about it.
I'm like, whoa, whoa.
Chill.
Chill.
What?
And so I've had to go out and learn all this stuff.
So if you can kind of follow your nose via the analytics, via social responses, you can
get a pretty good taste for where the wind is going.
And that will at least bring your stuff you're writing into a vein where people want to read
it.
And that gives you a shot at grabbing their attention and grabbing their follow, bringing
those eyes to your product or whatever it is that you're doing in the SaaS world.
So that's, again, pretty general.
But that works.
It works day in, day out, week in, week out, every quarter.
It won't be the funnest writing you've ever done, but it will do what you want it to do.
One of the toughest parts of trying to start an online business is often the feedback loops
are really slow.
And so you do something and you're not sure what people think about it or whether or not
it's going to work until two or three months down the road.
And then you get to adjust.
Whereas if you're doing like, what would be the opposite?
Like playing a video game.
Playing video games.
You get an instant feedback every like five seconds.
It's like, oh, I died.
I lost.
I didn't shoot the person or didn't get the treasure.
And writing is kind of more like a video game where if you're prolific and you're regular
like you're talking about, if you're constantly tweeting or you're constantly publishing things,
you just get maybe five or six points of feedback a day as, oh, no one cares about this topic
or no one cares about this particular thing I'm writing about.
Oh, this one really blew up.
And so I think you can course correct and just sort of go in the right direction much
faster than if you try to start off building a product or something really complex out
of the gate.
I think that's right.
And it is something that you get better and faster as time goes along.
You'll build muscles in memory for this sort of reactive thinking.
Also, you'll become a better writer.
And I know we're talking mostly about like regularity and like topics and that sort of
thing.
But also the quality of your writing does matter.
Writing better is better.
If you have a much better vocabulary, if you're better at turning a phrase, if you don't make
awkward comma errors, people will come back more often.
They will pay more attention.
They will give you more respect.
The cool part about writing on the internet when you're not good at it is no one's probably
going to read it, right?
No one's really paying attention yet.
So by the time people pay attention, you'll have got some practice in the bank.
You will have done a couple hundred posts and you'll feel better about it.
You'll have better ground underneath you from which to stand and talk.
My training in journalism was at the next web, T&W, back when it was like two part-time
people in the UK and me in college.
I was bad.
I was not good.
But I got to kind of write when the site was small and learn.
And so that's, I think, an analogy to what a lot of people will go through in this process.
But back to your point about long feedback loops in the building of business world, it
can take a long time to get an audience going.
When we launched Crunchbase News, we had a pretty modest audience.
We had my Twitter account, we had the Crunchbase Twitter account, which was pretty moribund
by that point in time.
I think we kind of neglected over the years.
And so we really had to start from scratch and it took ages.
It was not an easy process.
That was a grind.
The first year was writing for a much more audience than anticipated.
And then by the time that I left, I was pretty proud of it.
But it was a lot of just believing that it was going to work out and keeping pushing
forward.
So even with my perspective, I understand the length of time that it takes to kind of
get the skills going.
So I'm sympathetic to it, I guess.
Can you share what the results were of your time at Crunchbase News?
Because like you said, you went in and it basically didn't exist at the end.
And then you're doing really well in terms of traffic and audience.
What were those numbers like?
You can tell that I'm no longer 24 because my brain is going like in the reverse kitchen
to find them.
We were probably doing around a million pages a month, I think, when I left.
Somewhere in there.
That's within 50% of the correct another direction.
Somewhere in there.
But what was really exciting about Crunchbase News, what made it such an edifying project
to work on what was twofold.
One, the people I got to work with.
My team were amazing.
I love them.
I'm still close with nearly all of them.
But also it was the regularity of our growth.
We didn't have this moment at Crunchbase News when all of a sudden we grew by 50% a month.
But we grew by 15% almost every single month.
And so there was this compounding effect to our efforts and this pushing forward in every
month.
We set records six out of seven months.
We'd set a consecutive record.
And so it was just this never-ending push forward that was great.
I miss that feeling of working with a small team towards a near-term goal.
It's really, really fun.
But yeah, somewhere in there, we also had a little podcast and we had syndication deals
with Yahoo Finance and we were on Smart News.
And so we had other places where we derived traffic and so forth.
But that number is just on the blog, if you will.
So I think what you did at Crunchbase is something that a lot of people would like to emulate.
People could get millions of page views to their website every month.
Holy shit, their products sell a lot more.
You showed up.
They needed to build a news organization.
What was the very first step that you took?
And how are you sort of modeling this challenge in your mind based on what you would learn
from Mattermark and what you learned from TechCrunch?
My first step was to panic, mostly.
I realized instantly that I got in a much bigger job than I knew what to do with.
And that's why they call it growth, I guess.
The second step was to figure out where we were going to live.
There was no place on the Crunchbase website that was going to be a fit for what the news
team was going to try to do.
And the news team at that point was me.
So it was the news team singularly me.
So I had to get a blog up and going.
So the first thing I did was work with an agency, got a design put together and got
a site on the internet.
I picked up a couple of crew from the old Mattermark days that I kind of brought along
with me and we got up and running.
What I wanted to do first was start seeding the ground with posts to get information.
Where do we stand?
What does our audience react to?
What is a Crunchbase reader?
Who currently knows about us?
I mean, to me, that was kind of a blank slate.
In the best possible sense, a blank canvas, you can go forth and kind of draw on it.
And so we just started writing stuff.
We tried to write stuff that people weren't writing.
We tried to have a data focused perspective on the news in a way that other publications
weren't.
And we tried to let our personalities sit out there a little bit.
We didn't seem boring.
We weren't trying to be writers or the AP of the startup world.
We didn't want to do that.
And TechCrunch already existed.
So we went in a slightly different direction, a bit more data focused, a bit more chart
heavy, focused around similar topics.
But that was kind of our initial goal.
And you know, like I said, uptake was initially slow.
I didn't share analytics with the team for a little bit because I didn't want them to
get discouraged at how some of the best stuff they were writing wasn't hitting yet.
And we finally found that audience, and I didn't want to be like that flocked, do it
again.
But that's what I had to do.
But only I knew.
And then later on, of course, analytics were entirely open to everybody.
And everyone got to see everything.
So that was a short phase.
What metric do you care about?
Is it just overall page views to all of our content?
Is it newsletter subscribers or social shares?
That's going to depend a lot.
So I don't want to let my answer color the people's perspective too much because what
Crunchbase wanted, the corporation, they kind of wanted new, unique people.
Can the news team bring in people to the broader world of Crunchbase that are new, that haven't
been here before?
Which I think is pretty smart.
It's a pretty good metric and a good way to approach thinking about the value that a journalistic
arm brings to the company.
Internally, we cared a lot about that number as well.
We also tracked kind of standard publishing metrics, page views, follower accounts, news
that are subs, that sort of thing.
We tuned for different metrics at different times, I want to say, keeping an eye on being
read, but often focusing on other metrics than just page views.
You don't want to let page views run your life, but also you can't have people not read
your stuff.
So page views can't matter not at all, but they also can't matter entirely.
And then, of course, depending on what we're working on for a month or a quarter, depending
on our OKRs, what we're doing, it would change.
When we launched the podcast, we did a different set of metrics around that that we were focused
on.
And that, of course, bent our attention in that direction.
News that are subs is a great one, newsletter open rates, CTRs, all that kind of stuff,
but it just varied based on our near and medium-term goals.
So that's a crappy answer of saying it varies, but it really did.
Sorry for that.
When I look at any media organization, for example, if I look at TechCrunch, you've got
this homepage, and there's just hundreds of stories, infinite scroll, you've got a newsletter
sort of sign up box, and you've got like 10 different newsletters you could sign up for.
And then you've got like your Twitter, you've all these different channels, I'm sure you
get traffic from search as well.
Is there one in the very early days that seems to dwarf all the rest?
Like where are you getting your first traffic, your first readers from when you haven't really
made a name for yourself?
So great question.
So for us, it went first from social, because we had existing social, we had personal accounts
that had followers, right?
So we could get people to show up and read the site in dozens of people, maybe 100 people.
But that channel tops out pretty quickly and doesn't grow.
From there, it was all about building an initial SEO base and getting onto the search game.
Because back to your question, what drives the majority?
Google is an amazing traffic source.
And I know that Google has diminished itself in recent years by adding more ads up top,
trying to answer questions to those terrible little boxes and kind of defiling its UI with
tons of crap and cruft and just yucky stuff.
Google search, remember when it was good?
But still, to this day, Google is an enormous driver of traffic to media companies because
we provide the risk that people want.
And so Google serves it up.
People want to be informed.
And I think that's why news content or news stuff, journalistic stuff, for lack of a better
case, does have constant market impact because people have the thirst to know what's going
on and be informed.
And that same sentiment applies to a lot of stuff that I read in the SaaS world about
what SaaS metrics should hit, what should your LTV2CAC be in 2020?
People will read that because they're desperate to know.
Similar emotions, slightly different target point, if you get what I'm saying.
But search is gigantic.
And then from there, you get to do more exotic stuff.
Like for us, our partnership with SmartNews was a long time coming.
We built our RSS feed and worked with them and there were lawyers involved.
But then we got to publish over there.
We got to publish on Flipboard to some degree.
And you begin to work in these other partnerships as you scale, get more attention, get more
in-market respect.
So for us, it was social search and then stuff we kind of layered on top to build out our
gestural ground, new eyeballs, and try to reach new audiences with writing that we were
proud of.
By that point, we had an artist working with us.
We had lots of custom art that we were doing.
We figured out our branding.
We figured out our logo.
And we really kind of reached a nice state of equilibrium that I was pretty proud of.
So let's go like one at a time.
Earlier on, you're doing social.
I assume that just means you're tweeting out the articles that you write.
One of the things that I've found that people who have a ton of Twitter followers do is
they often adapt their content to Twitter.
So an educator who's teaching people how to code will create all sorts of cool graphics
that are easily shareable or retweetable or tell lots of jokes because people get retweets
on jokes.
Were you doing any of that or was it just as simple as publishing to your blog and then
just tweeting it?
Yeah, we should have been more sophisticated.
If you've watched the growth of Morning Brew ever, there's that newsletter group that's
been doing it.
Yeah.
Just to be clear.
They look like they're having so much fun.
They're all super nice.
They're all super engaged.
I don't know any of them personally, but if TechCrunch fired me and I was like, oh crap,
I would be like, hi, can I come write for your newsletter because I just think they're
great.
They have been so brilliant at using social media and various bits of, and I mean this
in a completely non-mean way, attention-grabbing stuff to get more stuff for their brands.
If you're looking for a good example, go look at that.
We didn't have someone who was super in charge of social in that way, and so our social was
much more basic.
But because I had, at that point, 50,000 Twitter followers, whatever it was, 40,000, I don't
know what it was back then, we had some basis from which to stand on.
Because journalists followed me, other journalists in the field, they would often retweet us
and so that would help broaden our reach originally.
So we were kind of leaning on what we already had, but everyone has some community, everyone
has some platform, be it LinkedIn or Facebook or even Instagram is surprisingly effective
as well.
And of course, today, TikTok.
I'm not quite sure how that would fit into the SaaS content world.
Maybe it does if I was more creative.
But for us, it was Twitter, LinkedIn, and trying to hit the obvious stuff, building
pages, getting our first thousand likes on Facebook, just really sort of basic shit.
I mean, it's all hard, it's all slow.
It does compound, and the first one's the hardest.
But you can't not be present in those areas, I don't think.
I think trusting that it's going to compound is something that maybe you could do because
it was your full-time role.
But often founders don't have that trust.
They're writing a lot of stuff week after week and they're like, the numbers aren't
growing.
People, maybe I wrote that one article, and it got 200 retweets and it was amazing.
But my next article was a complete dud.
It doesn't seem like there's any connection.
And it seems like this endless treadmill.
How do you actually build up this audience into something that is compounding over time
and isn't just a bunch of hits and misses?
Do you know Jason Limkin?
I do.
Sastre Guy.
Yeah, Sastre Guy.
I love Jason.
Jason's fantastic.
He answered questions on Quora forever.
He's done like a bajillion Quora answers, and he's done a bajillion emails.
He brute forced his way into the center of the SaaS world by being ubiquitous and as
helpful as possible.
I always think back to his example whenever I get a bit bummed, like if I publish an article
and it flops.
I'm like, oh, I'm over.
This is it.
This Wednesday.
It's the end of my career.
I'm like, would Jason give up or would he write 65,000 more articles?
And I'm like, all right.
All right.
And I bring up Jason because he is very much in this startup SaaS world, and he's managed
to build attention on the back of technical SaaS advice and company-building stuff.
When it comes to kind of keeping at it, he's the North Star, I think, in the startup world
for what happens when you just don't give up.
So you don't take my word for it.
He's done it.
And you can kind of steal from his example, I think.
The other side of this is it just does work.
If you write stuff that people care about, over time, they will stick around and they
will attach themselves to your brand, your media property, your account, whatever it
is you're trying to get them to pay attention to because you provided them with something
they didn't have.
To the person in your example who is saying, oh, I've written 50 things.
One of them did, well, maybe that's a good ratio.
Maybe 2% going viral is pretty good.
So that means that every 50 things you write, one will go viral.
Cool.
So write 400 things, go viral a bunch.
Then you go viral eight times.
I think a mistake that people make is the expectation that any single piece of content
will either mimic previous success or will push the ball farther forward than it otherwise
might.
A lot of writing is incremental.
A lot of news is incremental.
And that's just the way it's going to be, I think, forever.
And one of the interesting things that I've seen that you did at Crunchybase News and
pretty much every large media organization does is you kind of diversify the types of
things that you're writing.
So it's not all educational stories.
It's not all gossip.
It's not all data-driven.
You kind of mix it up.
There's a lot of variety and novelty there.
But how do you know what the best mix is?
Like when you came into Crunchybase News, there's an infinite number of types.
You could do interviews with people.
You could do investigator journalism.
How do you know what's going to resonate?
And how do you decide what's worth working on and writing about and what you want to
avoid?
Because you get about, you know, I wrote, I think it was a couple thousand pieces for
Crunchybase News.
I think total over the couple of years.
No, it wouldn't have been at least a thousand.
Somewhere in the four figures anyways.
So I took it.
I had a bunch of at-bats to tinker with that and figure out what it was.
And so you end up figuring out, like if I write this, it'll probably do pretty well.
I'll write some of those.
I think this person on the site as an interview is going to be really useful to people who
are trying to figure this thing out to understand this part of the world.
And so you just sit around with yourself and a pad of paper or with your colleagues and
several pads of paper.
And you talk about it.
I mean, it's a pretty, in every newsroom, there's some form of a regular get-together
to talk about ideas, trends, changes, interviews, and something like that.
And so you just have to kind of do that process.
Now, of course, the world of journalism is going to be different than the world of like
building content to support a SaaS brand.
But there's going to be similarities.
And this is one of them.
And then back to our point about analytics, that will guide you a little bit.
You know, if you only want to do things that are highly successful, you're going to struggle
because it's hard to have repeat successes.
But certainly, you can look to what things tend to do better on average and lean in that
direction if you want to choose shorter-term numbers.
But generally speaking, talk to interesting people, write interesting things, explain
the world or explain how to do things, and people will show up.
Can you give me an example of maybe a particular type of article or a trend that you figured
out at Crunchbase?
And maybe you had your meeting with the writers.
You said, you know what?
This works really well.
We should do more of this.
Yeah.
I'm just curious what that process actually looks like, something specific.
Short and short, we call them explanatory pieces.
And they're hard to do, but we did a couple of them.
One thing that we always wanted to do more of was explaining arcane topics that you only
find out when you're a founder in too deep to not learn them, like how to structure a
cap table.
Like, people don't do that unless you have to do it, right?
So then it's too late if you don't know what's going on.
Or like, how does ratchet work if you get a down round and you're getting a rescue VC
deal?
So one thing we did was we wrote a series of articles about a fictional company.
They were doing, I can do this, a drone delivery of fried chicken, I think, or chicken wings
or something.
It was this fake company we made up.
And then we walked them through over a series of stories, a couple of VC rounds, and we
had a fictional cap table that we updated every post.
And then we had them get recapped and sold, and we walked everyone through what that looks
like inside the numbers.
It's very time consuming to do, but we discovered that these explainery things had an insane
shelf life.
I wrote a piece entitled, How to Read an S1, the IPO filing document you would give to
the government.
And that's still doing numbers, I presume, over there, was when I left.
Did it take forever?
Yes.
Was it worth it?
Of course.
So we mixed in those with our news stuff, longer and shorter form.
We thought about content kind of in short and long increments to me, kind of what we're
working on.
And then we tried to build intelligent channels, and we launched a weekend email newsletter
for a few people, and we let that have its own personality.
And you just kind of tend to expand and so forth.
But the explainery stuff was a trend we noticed early, we invested in, and it paid off pretty
well.
What stops you from just going all in on that?
Like, hey, this trend works well, reliably, you know, explainery articles, get more traffic
and have longer shelf life than other articles.
Why not just do 100% explainery pieces?
Well, you run out of stuff to explain, and you'll get sloppy, and you won't have the
best ideas.
Like the how to write an S1 piece took a while to put together.
It wasn't like I sat down on Tuesday and it was done by Wednesday morning.
That piece took a minute.
We thought about the layout, we thought about how we were using images and art, and we did
a good job, I think.
But it took a lot of time.
So that's not something you could do every day back to our point about regularity.
It would just be impossible if you had a simply enormous team and a very wide purview of things
to explain.
So we use that as a targeted weapon, as opposed to like a carpet bombing exercise.
We wanted to keep everyone on the site every day.
We went through the show-ups, and we always had stuff going up, but it wasn't always the
longest stuff.
You don't always have to do that.
But there is a really good point there, because people are always looking for a hack to get
around doing the work when it comes to writing.
And I don't think there is one.
Unless you're like super famous.
Like if you're super famous, anything you write, people will read because you're super
famous.
But I mean, most people aren't.
I'm not.
You're not.
You're not even 1% of the way to super famous.
Thank God, because that's a miserable life.
But like, there isn't going to be probably a hack to building a long-term content property
or media property for my world that is good based off of finding one cheap trick.
I mean, that's what Uproxx and all those companies did.
And they were like, you know, soldier comes home, you won't believe what happens next.
They found this one way to hack the Facebook algorithm, and they blew up.
And then they immediately cratered when the algorithm changed.
That's a good warning for that kind of thinking, I think.
Could you describe it as an accumulation of cheap tricks?
Like, you've got your Explainery article trick, and then you've got like your Superviral
Gossipy article trick, and then maybe, you know, a media organization is just like five
or 10 of those.
And that's all you need.
Well, I wouldn't call them tricks.
I would call them huge investments of hard work.
So the trick implies that I'm doing something to confuse you.
I know what you're saying, though.
But we never did the Gossipy thing, really.
We never did anything in those lines.
We tried to not cover people much, we tried to cover companies and trends.
And so we set maybe a harder challenge ahead of ourselves than we had to.
But like I was trying to say earlier, I was making it up.
I hadn't really done this before.
There's a lot of trial and error, and a lot of error from me just being inexperienced.
But I tried to fix that by working as hard as I could, and that went okay.
But I think you do end up with six or seven techniques, methods, perhaps, that you use
to approach the market.
In my world right now, I write a morning column, so that's part of my output.
I do two podcasts a week, Mondays and then Thursdays.
That's part of my kind of structure.
And I'm also talking to people all the time.
I'm talking to another VC this afternoon, and I'm going to have a bunch more notes about
that.
And I'm always trying to talk to people, listen, ask probing questions to learn more stuff,
so I have more stuff to write about.
So that way, when news breaks, I have a lot in the back of my head that I can bring up,
like, oh, this connects to that.
This is what this looks like.
And people love that sort of connection.
So it's techniques and practice, much like anything else.
If it was tricks, I think everyone would do it.
Then everyone would have this super successful media property, but they don't.
Yeah, I mean, writing every day consistently is a pretty hard, quote unquote, trick to
pull off.
There's no shortcut to doing that.
I mean, to be clear, though, Karlin, I don't want to do anything else.
This is the job that I want.
So I don't want to overly pessimistic about it.
If you enjoy writing, if you're very full of shit, like I am, it's lovely.
I can see, though, people who are a bit quieter and less talkative might be a bit more onerous.
What if you don't enjoy writing, but for whatever reason, you're like, I want to start a media
company.
Maybe I'll hire some journalists.
How do you identify people who can write for you or with you?
And how do you even structure a small journalistic organization?
So the way you said it was really funny.
What if you want to run a marathon, but you hate jogging?
How do you hire a pinch marathoner to run in your place?
Yeah, well, in that case, you just write your name on their forehead and off they go.
So having been the journalist that has been brought in twice now to do this, I suppose
I'm something of an expert, which is embarrassing.
They don't actually really not answer your question.
I would look for someone who has some managerial experience.
I would look for someone who has as much experience in the topic area that you care about.
And then I would decide to trust them.
Because what you don't want to do if you're the CEO of a company and you're trying to
launch a media brand is to micromanage it, because it needs to find its own voice a little
bit.
It needs to breathe.
It's going to be generally aligned.
You're not going to have auto parts, e-commerce company, and a publication about how to make
grits.
That would be strange, but you're going to have something that's generally aligned.
But then let them have space.
Let them breathe.
Let them walk free.
And then just have some really clear metrics you want them to hit and then fire them if
they fail.
It's super hard, and given the number of people in the media world who have been laid off
in the last, I don't know, five years, there's probably some pretty great people out there
you can get for a reasonable amount of money, but you have to decide to trust them.
And that's the thing that a lot of people struggle with because they want to run it
like a marketing team.
They want to sit there and say, well, you should have put that link there because we
have 0.0% to work with the rates.
No, it's not marketing in the strict sense.
Don't treat it that way, and then you'll be fine.
Yeah, what is the difference between content marketing, as founders like to say, and a
traditional media journalistic organization?
What separates it to you?
Well, a world of difference, really.
Anyone can put together a publication on their site and have it run from the corporate voice.
That's not hard to do.
There's no rules to follow.
I mean, as long as you don't have a suit for libel or slander or whatever, you're fine.
If you want to have people come and presume that they're being told stuff not strictly
for the advantage of the company who's paying for the site, then you need to bring in the
traditional rules of journalism.
That gets a little tricky when you work for a company.
One of my jobs at Crunchbase was to be the buffer zone between Crunchbase and the company
and Crunchbase News, the publication.
It was my job to make sure that the news team was unencumbered as best as I could from what
the corporation wanted.
It was to be like, here, we're going to sit and do journalism and make lots of noise for
the parent company, which will bring people to the site.
It'll bring links like The New York Times covered something that we wrote on the front
page of the business section.
That was cool.
I have that.
Actually, it's right there.
I saved it.
But there's more autonomy required.
There is conflicts of interest, stuff like Crunchbase couldn't say, hey, news team.
We want to land a deal with so-and-so.
We want you to cover their stuff.
I would have been like, absolutely not, because that's not how this works.
We didn't do transactional stuff like that.
We tried to abide by every element of traditional journalistic ethics, which is too long to
explain here.
It's not really the point of the show, as we could, and it was my job to hold that up
so we could proudly call ourselves journalists without any sort of wink or diminishment.
That's harder than probably what most companies want to do.
But I think even bringing an ex-reporter in will bring some rigor to a newsroom that you
otherwise might not get from someone who is more of a content strategist, say.
Yeah, so you hire a journalist, you give them a lot of autonomy, ideally they understand
the rules of journalism, and they've been doing this for a while, and so they can figure
it out.
And I've noticed, as you said, there's been so many layoffs, and it's kind of how I realized
this trend of journalists have a ridiculous number of followers, just going on Twitter
to seeing journalists and said, hey, the outline or whoever just laid us all off, and I look
and they always have these very witty tweets, very good writers, you could tell they live
on Twitter all day, and they'll have 50, 70, 100,000 followers.
And it's actually surprisingly inexpensive to hire a really good journalist.
It's shockingly cheap compared to what one might expect.
It gets more expensive in the business world, but yeah, it is still cheaper than you think.
If you're used to paying...
You and I both have friends that work at big five tech companies, and you and I both know
what mid-level engineers make for not working very hard.
Journalists will work a lot harder than that for a fraction of the money.
So we're a bargain, so go get yourself a cup because people need to eat.
I'm conflating two things, though.
So let me try to tease these apart.
You can hire someone to come write on your corporate blog with a journalist background
and they'll do well, to be clear.
But if you want to build a more serious, slightly distinct media outlet, distinct from your
product, that might be a center of gravity that attracts people and attention and inbound
links and that sort of thing, I think you should set that up a bit more strictly and
have a bit more separation between the two.
But from the corporate perspective, I think either one is merit.
It just depends on how seriously you want to go about this.
If you just want to have a better blog, cool.
That's not that hard.
Hire some people.
Go hog wild.
But the step above that is to build your own little media org, and I think that should
adhere to traditional journalistic rules.
I think that one of the best bits of Twitter that I've seen lately about this topic was
a tweet that said, don't build a blog, build a media brand around your SaaS company.
I forget the exact quote, but I think it's a good point because people will trust the
media brand because they've been reading it.
And then that trust will in some ways transfer over to the corporation itself.
I think the way that you frame these things is very important.
I don't remember where I heard this, but someone said, if you're a musician making an album,
instead of thinking about making an album, think about a movie or a story and then think
about making the soundtrack to that movie.
And it will give your work a lot more cohesion.
And I think it's kind of similar with a media organization.
Don't think about, oh, I'm going to have a blog and write articles.
Think about actually building a media brand, a magazine or something that people get behind
and then approach all of your articles you're writing from that lens.
And I guess it'll have more cohesion and you'll be able to do something that's much bigger
and more ambitious than you thought of otherwise.
Oh, dude, for sure.
I mean, the first round review back in the day was when Camille ran, it was a tremendous
example of what you're saying.
It brought first round capital, lots of attention.
I heard more about the first round review than I heard about first round capital.
Like Tamaz Tunga is over at Redpoint, has built a personal blog that everyone reads
in the world of SaaS.
And so he now has brought an enormous halo effect to his employer, which is weird.
Normally, it goes all the way around, but it just goes to show you how when done well
and when done correctly, this stuff has an outsize impact that can change not just personal
life, but also business trajectory, which is much harder to do.
So let's get into some of the reasons why a media brand can resonate so well.
I have my own theories and I feel like just like firing them off to you and you could
tell me, you know, that's bullshit Cortland or actually, that's actually very important
and you should do this.
Oh, this is going to be so much fun.
Hey, you talk and I'll just shot bullshit occasionally.
Okay, writing about basically current events to me seems necessary to build a successful
media organization.
Often people can write these blogs with nothing but evergreen articles, nothing but educational
stuff.
It's not related to any sort of thing going on in the world, anything that's happening.
I think people are significantly less likely to share it and to, you know, tweet about
it and to retweet it and to talk to their friends about it, which is pretty important,
as you said, for the very first phase of growth, where it's going to be mostly on social.
So in your opinion, how important is it that the content you write about focus on current
events?
It can't not do it ever, but it doesn't always have to.
You don't always have to have what we call a news hook, right?
But often it's a great way to frame the piece.
So if you want to make a point, a broader point, hang that on top of something that's
happening that people are searching for, looking for, that they care about now.
And they're much more likely to read the thing that you wrote and then get the thing you
were trying to say that might have been evergreen.
And you can always write the evergreen piece anyway.
It doesn't preclude that.
You're not, you know, banned from it.
But having a news hook is a great way to draw near-term attention.
And anyone in the media game knows how to find a news hook for something.
So it's a good point.
And I think you nailed it.
Yeah, define news hook.
What does that mean exactly?
What the hell happened that brought us to talking about this thing?
And then we can talk about more related things, but it's what happened.
Tesla reports earnings or, you know, Tesla's car crashes into semi-well and autopilot mode.
Whatever the thing that just went bang, boom, crash, or sort, whatever that is, is the news
hook.
And then that lets you do a lot more stuff around that, but that brings people into the
moment.
It also grounds it in a place in time, which I think matters a lot.
And I think a corollator to my first point is not only should you write about things
that are current events, not only should you have a news hook, but certain things just
are more remarkable to people than others.
So writing about someone who everybody's familiar with, Elon Musk, for example, writing about
a company that people are familiar with, Apple or Google, is almost always going to net you
more traffic than writing about something obscure that people don't already have a personal
connection with or personal opinions about.
How much do you think about, I guess, the familiarity of the subjects that you write
about when you're leading a media organization?
It's so you're not wrong at all that if you put Tesla in a headline, you will get many
more clicks on Twitter.
You also get many more emails from really annoying Tesla shareholders.
Those are great.
But I think you can't only do that.
Back to our discussion about content diversity and having a mix of things.
Covering hot button companies and people is a great way to bring in some folks to the
publication, but one thing you'll find is that they won't always be the highest quality
readers.
They'll be there just to read a paragraph and then go rage about it on Twitter.
So I think it's never a bad thing to have some stuff that touches that line of wire.
But I wouldn't make it the only thing that you do or you end up chasing things that make
you appear vapid because once you realize that Elon Musk drives traffic, you'll cover
more Elon Musk stuff.
You'll cover more trivial Elon Musk stuff.
You have to do the standard of quality at the same level.
You can't let that diminish just because it's traffic generated.
That said, I do love to see the numbers, but when I do cover Tesla, it's a lot of fun.
I think you're otherwise right.
I would just say there's never going to be one thing you can do exclusively and have
it go well.
But I think that sort of stuff is a great thing in the mix.
Have you ever had a trail mix like peanuts and whatever you're hiking and sometimes
you grab a whole handful and it's all nuts and sadness and then your next handful is
like all M&Ms and you're like, yes!
Sometimes you'll go a bit more in the newsy, famous people direction.
Sometimes you'll go more into the niche stuff.
Sometimes I write stuff for a week that no one cares about but me and that's fine.
I kind of know that going into it, but it doesn't attract to when I write different
people in smaller quantities who I stick with.
I've met a lot of VCs by covering more niche SaaS topics who I now can kind of just call
it and get their take on stuff, then I would have written higher level, more celebrity
focused stuff, business like you know, covering Mark Cuban and whatever.
So it has a place.
It's certainly not a panacea and certainly it's a low calorie snack and it should be
treated like a Pop-Tart.
It's not really a full meal.
How important is it to break news quickly?
I've seen lots of media organizations writing about the same things that other people are
already writing about and it seems like there's this race to be the first and to not write
about things that are old, to write about things that are new and that just happened
yesterday or last hour.
Is that something that factors into your decision making?
Oh, God.
Yeah.
Yeah.
I mean, news freshness matters.
And so if you're going to cover a news item straight, Kortland buys Ferrari, drives it
into trade.
That's a news story.
That's a headline.
If you're going to report just that, you need to be quick.
But if it's, you know, local Ferrari driver crashes car, continuing pandemic, reckless
driving in and around town X, then you can write that a week later and you can frame
it around a broader context with more data.
So it depends on what you're trying to do.
The story will be different if it was later on.
I read a lot of what's called next day stuff.
So I let a lot of folks write the breaking piece and then I will jump on the analysis,
talk to some people, get some other quotes and kind of build around that to provide some
more context analysis.
And that's one way that I approach this.
But breaking news matters because people give a shit.
And if you can write stuff that people care about, they're going to come show up and pay
attention.
And that's ultimately what you kind of need.
If you're selling ads or subscriptions, whatever your business is, media or not, people showing
up does matter.
And so you always have a bias towards what's happening now.
I like how you mentioned that you'll do multiple pieces on a particular news or a particular
event.
So there might be the breaking news part of it where you just say, this is what happened.
We get this out as fast as possible.
But you also want to do an analytical piece on it and you also want to figure out the
broader themes and the broader story and how this fits into other big stories and topics.
Is there almost like a playbook you have for, okay, this event happened, we need to cover
it from all these different angles?
Every publication is very different.
There's some publications that are very top-down, editor tells editor, who tells sub editor,
who tells writer.
The reason why I came back to TechCrunch is not just the lovely people who I'm so lucky
to get to work with again, because most of the staff is the same as when I was here before,
but it's the autonomy.
TechCrunch is more of a very flat organization.
And so we do a lot more intra-writer collaborations versus top-down playbooks.
So it's not like we have a three-point plan, like, ah, X happened, you'll do this, you'll
do that, you'll do that.
It's much more organic, which I find to be much more creative and enjoyable.
So we probably have playbooks that I just don't quite see in our patterns of coverage,
but nothing as explicit as that.
Another thing you've been talking about that often, I think people who write news talk
about, but the people who have blogs and sort of corporate publications almost never talk
about it.
It's just this word, story.
If you think about just plain facts, if you can get facts from Twitter, you can go on
Twitter and see people tweeting, oh, this happened, this happened, this happened.
And I think one of the reasons why websites like Twitter haven't never well killed journalism
is because, well, there's no story around the facts.
A journalist can actually take this fact and that fact and weave them together and say,
well, here's actually what's going on.
Here's the greater narrative.
Tech is becoming a monopoly or people are leaving San Francisco.
How important is it that when you relate some event that occurred that you include some
sort of story?
What are the details you think about for what makes a story good?
That's a really great set of questions.
I'll try to be relatively brief.
I think you nailed what a story is and that if you just have a collection of facts, you
have bullet points, which are an effective tool that I use occasionally when I'm writing.
If I need to, they're fantastic.
But there's certainly one tool on Toolbox.
You can't only use a hammer to build a house, other as you have a really weird ass house.
So building context and walking people through why something matters is very important.
Just to bring it home to what I do is I cover a lot of the late stage startup market and
I cover the IPO market and a little bit of the public markets.
One of my jobs is to kind of explain to people what's going on between the two to walk them
across the divide as IPOs happen and that sort of thing to explain what the hell is
going on for startups in the exit market for IPOs in the private markets and kind of back
and forth.
I do a lot of context building, I try to do this, I try to build context, provide a narrative
flow to things and cover things thematically over a multi-month period to let people know
what's going on.
And so if they read my stuff, I hope they walk away reasonably informed about what's
happening in the world.
And if you just gave them a dose of facts every day, here's seven, they're going to
forget them, they're not going to flow together and they won't be able to draw the connections
that you're drawing because you're in the zone covering all this stuff.
And so I think it's a very, very important part of building a publication.
And this is the craft element of it that I was talking earlier about getting better over
time.
As you get better at this, as you practice it, this becomes more easy or becomes easier
and much faster as well.
And so you end up being able to write relatively quickly stuff that would take other people
a lot longer to help kind of walk you through the news hook, through the facts and into
the context of what matters to their life, their startup, whatever it is.
And how important is it to sort of own the story because the story is completely subjective.
Two people can look at the same facts and have a completely different story around it.
TechCrunch's perspective on it might be, oh, XYZ is happening.
More people who have started companies are looking to, I don't know, bootstrap.
And someone else might look at it and have a completely different conclusion.
And I think one of the options you have as a media organization is you adopt someone
else's story.
You see, oh, this publication is writing it and this is their angle on these facts.
You're going to buy into that and just provide additional context.
But also as a journalist, you can essentially create your own story.
You can say, no, I'm going to completely ignore what other people are saying about this and
my own narrative and my own theme for what's going on and talk about this for months.
And you often see this with, for example, Ben Thompson as your tech read.
I think he does this a lot where he has his own unique analysis of what's going on and
it's a different take than really anyone else has.
Is that something that factors in?
Do you care about being unique with your story or is it more so just important that you're
talking about stories that everyone wants to share?
It does matter.
I don't think about it, though.
I don't think about it in going, is this sufficiently unique?
I just try to do the best job that I can telling people what's going on, why it matters and
so forth.
When it comes to your discussion of facts, I would quibble a little bit with how you
could theoretically get entirely different perspectives on things.
What Ben Thompson does as your tech read, and I read tech read here and there, I used
to be a subscriber that I'm a fan, for lack of a better phrase, guys really smart.
And he uses these images very well to help kind of build on top of this text and it's
quite well done.
He sets usually a level up from everyone else who are analyzing more discrete news events.
He's built essentially kind of a one-of-a-kind media company, so none of the stuff that he
does applies to what the rest of the world does.
He's got a huge subscriber base.
He does the thing he wants to do.
People love him.
It's not really replicable.
He certainly is an envious, if you will.
I think that when there's a set of facts, there's only so far you can go from them without
being entirely full of shit.
If you want to go Fox News, sure, you can just say whatever you want.
It doesn't matter.
Nothing is true.
Trump's always right.
Of course, whatever the president said, we can find a way to twist our logic around and
make it work so scared old people will vote for him again, whatever.
But if you live in the realm of reality, if you're attached to the planet, if your feet
are actually on the ground and your brain is switched on, I don't think you can get
too far away from the facts.
It's actually the grounding elements of what drives coverage.
People are covering Robin Hood because it's growing so fast.
Robin Hood could have done some PR tricks.
They could have done some cool things.
You get attention to themselves.
But fundamentally, they're changing their entire market, so we have to write about them.
They made themselves impossible to ignore.
We will all cover Robin Hood's growth, its monetization, the good stuff, the bad stuff,
but they become a place that you can't not go.
I think that's when the uniqueness factor comes in.
What can you bring to the table on a story like that that's particularly good and interesting?
Bloomberg today, as we recorded this, I don't know if this is coming out, wrote a really
great recap of Robin Hood breaking some news on some investigations that are under.
That's a new fact that they've brought in.
Robin Hood will try to spin that, but I mean, it's a fact, and so that's going to change
the way coverage goes for them.
I don't know if I answered your question.
I'm trying to hack at it in different directions.
Does that help at all?
Yeah.
As someone who reads a lot of news, it's interesting to me that I don't know how the sausage is
made.
It's been so much of my time looking at this stuff and seeing what's going on.
It's part of why I wanted to talk to you.
What's going on behind the scenes?
There's this almost interplay between what successful media organizations are covering
and the stories that are going on and what they want the story to be, so to speak.
For example, you could say that you can't not talk about Robin Hood, which certainly
seems to be true.
It's a huge topic, but it's also in part a huge topic because media organizations are
choosing to talk about it.
For example, someone wanted to talk about my employer Stripe, well, there's lots going
on at Stripe, and it's one of the fastest growing tech companies, but it's not as exciting.
It's not as consumer focused, and so it doesn't get as many articles written about it.
But it seems to be almost a self-fulfilling prophecy.
Because you choose not to write about it and other people aren't talking about it, then
it makes it easier to justify not writing about it.
I guess what I'm really curious about is how do you see your obligation to create stories
versus your obligation to report on what people are already talking about?
By create stories, you mean go forth and find stuff that matters and isn't being talked
about?
Exactly.
I think it's a big part of my job because the last thing you want to do is to send into
generica.
You don't want to become exactly similar to some other publication.
You don't want to lose any sort of angle on the world.
You want to bring something that other people aren't, otherwise, why are you doing it?
The internet distribution is free, so if we want to write the exact same story about X
or Y, who really cares?
Some traffic?
Come on, really.
Traffic, as you and I both know in the ad games, is not super valuable.
When it comes to Stripe, though, Stripe is pretty well covered for an enterprise company.
For companies that sit in the background, they do a pretty good job of bringing attention
to yourselves.
I was at a Cloud 100 thing when Patrick was just up there talking to a room full of a
couple hundred VCs and eight journalists.
The company doesn't lack for attention and so forth.
I think it's the companies that are small, that are like a couple of people building
a slash product, they're like a million AR or whatever, and they're desperate for attention.
That's tough.
It's really tough because there aren't so many journalists covering the startup world
that the amount of attention we have to give out can drip all the way down that far.
That's just the struggle of the news.
Business is economics going to hell and the industry falling apart.
Back in the day, there were a multiple of the number of journalists in the world that
we have now, at least in the US.
There was more folks listening, more folks to talk to you, more folks to go out there
and talk to that person in the small business and get their story.
Now I get yanked by breaking big news off of smaller stuff just because that's a fact
of the way the world currently works.
It's not good or bad.
It is bad, but it also is.
I'm sympathetic to the person who gets ignored, but the best way to get attention is just
to kick ass.
If you're incredibly interesting and you're very successful, you will be talked about.
The tonic, the antidote to being a startup that's ignored is just to crush it and people
won't pay attention to you.
That's tough and most startups won't do that.
It's kind of a shitty bit of advice, frankly.
This is exactly why I started Indie Hackers.
At first, it was literally just a blog or a media company and the whole idea was there
exists an entire subset of founders building companies that are interesting to lots of
people, but maybe not broadly interesting enough to get mainstream media coverage.
TechCrunch is not going to write about someone who just got to $10,000 in monthly recurring
revenue.
I wish we could.
There are still tens of thousands of people who want to read that.
I wish we could.
I try to always pick up a couple of seed rounds here and there to highlight people.
I'm currently corresponding with a startup from YC's demo day last week that I think
is awesome.
I try to have, I know some local entrepreneurs in my hometown here, Providence, my adopted
hometown.
I'm trying to get to know people that are building smaller stuff, but it's an enormous
amount of legwork to write something that people don't really want to read at the same
scale as a bunch of other stuff.
You do get torn between the realities of the industry you live in and also how much space
you can generate for yourself to write the stuff that you really care about.
I'm lucky in that I work for a publication that gives me a lot of freedom.
I have a bit of a personal readership, a couple of people read my stuff just because I wrote
it.
Between those two things, I can go out of bounds a little bit more often than I might
at a different place, which is why I'm going to stay put at TC.
I'm sympathetic to what you're saying.
I don't have a solution for it other than fixed journalism and economics, which will
help.
If we can pull that off, then I would be super rich.
You mentioned Ben Thompson having a huge personal following.
People like him as a person and his perspective on things.
You have a huge Twitter following.
You have people who like your perspective on things.
Have you considered just being a solo journalist and whether or not you have, what do you think
differentiates that sort of role from writing for a bigger publication?
Yeah, everyone's had that thought.
In the same way that every engineer working in a team for an idiot has been like, I can
just go build this myself.
I can just get my friends, we can just launch our own company, we can build our own product.
The indie hacker thing, you're asking me, why am I not going to do that in journalism?
The short answer is I'm trying to have kids, and so fraternity leave sounds great, and
I've got good health insurance, and my wife is in residency, so I make most of the money.
I'm sufficiently old that my life's become boring, I guess is what I'm saying.
I think that's next for me if things go well.
Not soon.
I'm not going to leave TCI.
I just got back.
I'm super happy.
I'm getting to do a lot of stuff that I'm excited about.
I love the people I work with, but yeah, in five years, probably.
Yeah.
If Substack is still popping in five years, I'm in, you know, might be a terrible financial
choice, but it sounds like a really fun way to approach the world.
My internet friend, Polina, from Fortune Last, she now runs her own little media company,
Alex from Buzzfeed's doing this.
Some people that I know are very jumped in the pool.
They're very brave, and I'm proud of them.
I hope they do really well.
I subscribe to some of their stuff, so if it goes well for them, maybe I can talk myself
into doing it.
But working for big companies is somewhat easy.
You get a raise every year.
You get 401k, there's things that you get that are nice.
Yeah, I think the risk adjusted sort of expectation for what you can earn as an indie hacker is
not always as glamorous as it might seem when we talk about the success stories and the
standouts.
A lot of people fail.
There's a lot of risk that you have to take.
And it's something that I think you should do, not just because you think it's the best
financial decision, because it's probably not, but because you have some other things
right.
For example, if you can't work for an employer, there's just something inside of you that
just hates doing it, which is kind of the case with me and a lot of other people, then
it gives you that extra.
But if you're telling it at your employer and you love the sort of benefits that you
get, I don't think it makes sense to financially just jump in the pool as an indie hacker.
I mean, unless you just can't take it anymore.
Right?
Exactly.
And I respect that.
This is why I like entrepreneurs.
This is why I like covering startups.
You get to talk to people who have decided to do something really dumb, and not like
ignorant, but stupid.
Like, you were working at Google, you were mid-level, you were probably pulling down
350 a year, and now you're going to have to go start a company?
Great.
Good job.
Now, you won't invest all that stock you had waiting for you.
But I love that.
I love that people are going to go out there and be like, this probably won't work, but
I'm going to roll the dice.
I'm going to work super hard.
I'm going to build something I think the world needs.
And then you get to talk to them, and then they get to tell you how stoked they are about
fixing whatever it is.
Like, I've had people get so hyped about healthcare APIs, and I'm like, oh, lord, how do I care
about that?
And then they tell me why they're working on it.
I'm like, oh, shit.
All right.
Cool.
And I'm totally convinced by their enthusiasm and passion and just drive to make the world
a better place and hopefully a pile at the same time for themselves.
But yeah, I like talking to the crazy people, which is why I cover startups.
It's a never-ending font of fun folks and fun stories.
It's good times.
With so many people writing content online, I think one could argue that it's almost
a commodity.
There's so much to read.
There's obviously way more to read than any person could read in a day.
If you don't like one particular article, why pay for it?
Why even read it?
You could just go read something else.
And they'll find something to fill your time.
How do you as a new media organization get around that?
How do you compete with the fact that no matter what topic you pick, no matter what angle
you cover, someone else is probably already doing it.
There's already a TechCrunch.
There's already an IndieHackers.
Yeah, but there's already a TechCrunch and Adventure Beat and a bunch of other publications.
There's plenty of room for crunch-based news to show up, you know?
A bit like how you scratch your own itch by building a company to go out and fix the thing
that pissed you off, figure out what you're not reading that you want to.
And that'll be a good sniff in the direction of where you should go.
We at Crunch-Based News have this data-focused approach.
We spend a lot of time doing charts and looking up data and running numbers and trying to
provide a bit more rigor behind the anecdote.
One thing that I don't like reading is a trend piece.
People in New York City are wearing this type of thing.
And I'm like, it's fine if seven people on the author's front.
I don't care.
But if you bring data to me, you say, look, it's up 30% over the last two quarters, up
100% from the last year, I sit up.
And so we took that approach, and that was our angle.
But really, if you sit down and you say to yourself, there's nothing I can bring to the
market that's different.
I have no unique thoughts.
If I'm not interested at all, then don't write.
I don't think that's true about anybody listening to this show.
There is something that's missing.
They do have a perspective that's unique, and they probably have something to say.
It's hard to learn how to say it, but I think there's enough room for everybody online because
the internet's just so big.
You won't be a hit, maybe, but you'll have a good state regime of traffic and it'll help
you.
Yeah, I refuse to be pessimistic about this one.
The last thing that I think we haven't really covered that seems pretty important is just
the, how do you structure and actually write a story on the internet?
Obviously, on the internet, people are pressed for time.
If they're checking their email, they're on Twitter, they're usually in some sort of distracted
state.
Yes.
They're probably not going to read something that's boring.
They're not going to read something that's overly complex.
And in addition, as a journalist, you have this extra responsibility on you to basically
not get the facts wrong.
And you have all these other concerns we talked about where you might want to be writing something
that does well on Google or does well on Twitter.
How do you approach actually structuring a story?
What are some mistakes you think a novice might make that you wouldn't?
I think a mistake a novice might make would be to reach too quickly for a pattern they
can just use to hammer out stuff.
So I wouldn't ignore SEO.
I wouldn't ignore social titles.
I wouldn't ignore any of the things that are obvious, but I wouldn't over next to them.
I would spend a bit more time writing some short to medium-form things, being bad, having
my friends read them and telling me what they liked and didn't like, and then hammering
on my own style.
And if you want to improve quickly, the best thing to do is to go read books by great folks.
Whenever I feel my style going to shit, I go read some more books, and I get better
because you absorb through intellectual osmosis, this stuff from other people who are better
than you.
I'm not a particularly great writer, and I have a kind of annoying style.
And I've kind of given up trying to fix it.
This is just kind of who I am.
But you learn structure through practice, good inputs, and feedback.
And if you're going to be alone, you won't have an editor who can sit down with occasionally
and chat things through.
So you're going to have to find other folks to give you advice.
But no good piece of writing you've ever read was done entirely by one person.
It's always been a team effort.
So if you have to go assemble your team, do it.
But get some other inputs.
It can be your mom if she's got the time.
It doesn't have to be someone fancy your famous or good.
It's someone who reads, can provide some good feedback, where they got lost, where they
need some more context.
This happens to me.
People will be like, we need to know the sentence here.
You jumped.
And I'm like, you didn't follow my logic?
They're like, no.
I'm not in your head at a sentence.
I'm like, all right, cool enough.
So that's about it.
And then you can also imitate, respectfully, people that you really like.
You're not going to start writing Ben Thompson length essays to start, but you can go find
some people you like at say Bloomberg who write in a particular style, and you can go
learn from that.
And then finally, there are just resources to lean on.
So read the Bloomberg way, which is literally Bloomberg's book on how to do Bloomberg style
reporting.
Strunk and White's fantastic for style.
And then there's a zillion great books out there that you can pick up, but there's assets
and tools and so forth that you can pick up in writing groups if you want to go super
deep.
People listening is probably dumb, but that'll get you started.
So I'm trying to distill everything we've talked about into, I don't know, some sort
of very loose playbook for listeners who are trying to do what you mentioned earlier, not
just build a blog, but build an actual media company.
And I think some of the best points that you brought up that people can really take away
are number one, consistency.
If you're not writing on a regular basis, a lot of content, like people just aren't
going to read.
You're not going to get a lot of shots on goal.
You're not going to be able to build a lot of traffic.
Number two, like I like this idea of the firewall, if you're trying to build an actual media
organization, it can't just be this sort of corporate, very clearly, you know, trying
to push some product.
It needs to be something you think of differently than your actual product business.
And if you're one person, that might be kind of hard, but you need to understand that these
should be two different things.
Yeah, it's hard to have two personalities, but keep going.
Yeah.
Number three, this is a consistent theme you keep bringing up, you need to read a lot.
And you need to read a variety.
That might be very specific things like, you know, the Bloomberg Way, they're actually
a book, their actual book, but a lot of it could just be news, Twitter, what's going
on in the world.
And I think that feeds into some of the other tips you've given, which are, you know, write
about things that are recent, write about things that matter to a lot of people.
And ideally, write about things that you yourself wish you were reading.
Because that's a good way to sort of uncover what's not being written about and have your
own unique angle.
Are there any major things that we're missing here?
Like what else do I need to basically build a media organization?
Or is that it?
Could I go off and do it with only those tips?
I think the only...
So I think that's a good start and a really good summary, if I can just say so.
I would add just grit, the same grit that I think that fires up an entrepreneur is going
to be necessary for this sort of work, because while there's plenty of room on the internet,
there's also plenty of competition and, you know, you will have to fight for attention
and so forth.
So if you just decide not to give up, you're going to be fine.
It's hard to do that, as we all know.
But I think that does apply to the situation a lot.
And then I would add one more thing, have some fun.
Writing is good.
Being part of the conversation is enjoyable.
It's one of the funnest things that I've ever begun to do as a person.
And so, you know, you should find some joy in it as often as you can, hopefully every
time, every day, if not once a week, on the harder weeks.
But there should be some element of joy because you're bringing information to people who
want it, and you're helping them better understand the world they live in, and you're educating
yourself at the same time.
And that's a pretty cool job, or a pretty cool part of a job, if you're a solo founder
out there trying to expand and stuff yourself.
So, you know, try to smile, and then don't give up.
All right.
Well, I'm doing the having fun part.
It's fun talking to you, Alex, and getting to watch you almost choke on your drink when
I say that.
It's not lukewarm, really lukewarm coffee.
How long have you been talking, by the way?
I have no idea how long this has been.
I think it's been like an hour and 15 minutes.
Oh, my God.
I should go check Slack.
Finish.
What we're talking about.
Panic.
You've got stuff to do.
Yeah, you've got articles to write.
Where can listeners go to find out more about what you're up to, and maybe get in contact
with you if you're willing to answer some questions about journalism?
Yeah, yeah, yeah.
So, twitter.com slash Alex is my main social presence.
My email is alex.willhelm at techrunch.com.
I'm usually between one and seven days late on email, so apologies for that.
Life is busy.
I write for techrunch.com.
You can find myself around there.
I'm also on a podcast called Equity, where we cover the VC startup worlds, which is BLAST
and one of my longest projects that I've been part of, one of the funnest.
As you know, Carlin, podcast is just a blast.
It's never a boring time.
But really, I'm around to help.
If I can be of use, shoot me an email, I'll try to get back to you ASAP.
Time is limited, but I will try to answer whatever questions you have.
All right.
Thanks so much, Alex.
Listeners, if you enjoyed this episode and you want an easy way to support the podcast,
you should leave a review for us on iTunes or Apple podcasts.
Probably the fastest way to get there if you're on a Mac is to visit ndhackers.com slash reviews.
I really appreciate your support and I read pretty much all the reviews you leave over
there.
Thank you so much for listening.
And as always, I will see you next time.