"Build an audience first" might be the most common advice given to indie hackers. But how do you build an audience at the highest levels? In other words, how do you build an actual media company? To find out, I needed to talk to a pro. Alex Wilhelm (@alex) the Senior Editor at TechCrunch. He's also built two news organizations from the ground up — Mattermark and Crunchbase News — the latter of which published thousands of articles and broke over a million monthly pageviews. These are numbers that could easily turn a mediocre indie hacker business into a successful one. In this episode, Alex and I discuss the strategies and principles that differentiate successful media companies from half-hearted content marketing efforts, and drive millions of pageviews in the process.
What’s up everybody. This is Courtland from Indiehackers.com and you’re listening to the Indie Hackers 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 do they make decisions, both in 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.
If you’re on a Mac, the easiest way to do that is just go to IndieHackers.com/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 into actually, don’t just build an audience, build an entire media company, a media brand.
And 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 an organization that drives millions of page views rather than more simpler content marketing efforts that only get a few hundred or few thousand page views here and there.
At the end of the episode, we tried to distill Alex’s advice to a bullet list or a 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.
(end of intro) I know you’ve had at least two different stents where you’re charged with building an entire media organization from scratch, one at Mattermark and one at Crunchbase News. And 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. 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, was to build a little media company led by me, focused on the financial startup-y, venture capital type stuff, my bread and butter that I’ve written about for a while. It went medium bad until I went to rehab and then it went medium good until I quit. That was 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 not a dis in any way, startups are always resource constrained. You’re always making priorities. As Mattermark’s business didn’t quite proceed the way that we had anticipated, my resource base got diminished to the point where, “Okay, this is not going to work, but I sure learned a lot.”
As a personal year, huge, in terms of just learning – of 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.
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, though, is if you’ve never worked at a startup, it’s a really interesting environment. There’s nothing quite like it given the sheer lack of rules and formality.
So for me, going from TC, which was owned by AOL effectively, when I was there and then now Verizon, I’m inside the belly of a huge company, right. It’s just huge. Going to Mattermark where you can see the whole company in one room was just insane to me.
You could see everybody. Like, where’s sales? Oh, right there. Where’s legal? Oh, it’s that person. This is a strange place. So it was also a really good intro for me into the world of “in the guts” startup.
I got to go to a board meeting, and I got to do that “in the weed” stuff. And I, 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. It’s just so different.
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. What did you take from your time at tech crunch going to Mattermark?
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 Morrill, 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. There was a guy named Nick who was running that. Love Nick, fantastic human. There were already some bones in place, but what they didn’t have, though, was someone who was focused on it 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. 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.
It’s hard to jump over that fence if you’re not accustomed to what it’s like on the other side. But TC was interesting. Narrow that for me a little bit, because I could ramble 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 as setting journalism apart and 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, 80,000 followers on Twitter, and it’s not just you. I look at other journalists and they all seem to have 10, 20, 30,000 followers, like way more than the average founder. And there’s just something that seems to be about news that seems to be so good at captivating people and getting them to read and follow and building an audience.
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 a contract, part-time basis, because that was the amount of budget that I had to play with. It was maximizing how much I could get for my set budget at the time. 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 facing work that makes you lose credibility.
We ended up with a small team of someone who could help copy edit and run the site. Someone who was better at data journalism, and then me, was our trio, if you will. So it was a mixture of talents that we then tried to bring to the market. Then coming to the front part of your question about, what was our plan?
One of the most obvious things and well-known facts but 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. It’s really, really hard to go out there and actually write every day, unless you’ve done it forever. This is my job. So to me, it’s what I do, but for most folks it’s difficult. 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 and they can bring it forward. But with Mattermark it started off with just me. I rolled in as the journalist, there was no plural, it was just me. So then it was fun stuff like getting the blog set up and learning how to work with the developer team and that stuff.
For me, all this was new, informative experiences. Their goal was to publish every day. We eventually got there, and we got to cover some relatively big stuff. We got better as time went along and got better at just having regular chart colors for branding sake, stuff like that, that is pretty basic, but you have to learn, and it was a good year. I don’t think we accomplished there all that we wanted to. That’s why I was glad to 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 ideas and being a regularly consistent writer?
Well, one thing you mentioned a few minutes ago was how many followers journalists sometimes have on Twitter. I think that’s not simply because they’re journalists, I think because they’re there a lot. One thing that people like myself in the media do is we read constantly, and we stay up too late.
We read way too many tweets and articles and papers, and we watched too many interviews and we stayed generally informed broadly and then we niche down into our chosen vertical or focus area, if you will. 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 a problem with the SaaS product or they’re trying to develop a new brand or whatever. They get niched down. 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 so many posts attached to that one thing.
If you’re in my seat, I cover the public markets to some degree, startups, venture capital trends, Austin startups. There’s a lot of stuff that’s brewing around. So I always have something to grab onto. 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 that 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, that’s my take on it. So widening their topic 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 get the word out a bit more than you can by yourself, though, of course, you can always beat your own drum as hard 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 also it 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?
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. You can see in the numbers if no one cares and I try to not let that guide me too much because I’m a bit, I don’t know.
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 at 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.
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, “No-code is great. We want to talk to you about it.” I’m like, “Whoa, Whoa, chill, what?”
I’ve had to go out and learn all this stuff. So if you can follow your nose and 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.
That gives you a shot at grabbing their attention and grabbing their follow up, 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. That 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. 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 -- what would be the opposite, like playing a video game, playing video games, you get an instant feedback, every five seconds where it’s like, “Oh, I died. I lost. I didn’t shoot the person, or I didn’t get the treasure.”
Writing is more like a video game, where if you’re prolific and you’re regular like you’re talking about, if you’re constantly tweeting, 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.”
I think you can course correct and just 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. It is something that you get better and faster at as time goes along, you’ll build muscles and memory for reactive thinking. Also, you’ll become a better writer. 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 like by the time people pay attention, you’ll have got some practice in the bank. You will have done a couple of 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, TNW, back when it was two part-time people in the UK and me in college.
I was bad. I was not good, but I got to write when the site was small and learn. And so that’s, I think, an analogy a lot of people will go through in this process. But back to your point about long feedback loops in the building of the 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, having been neglected over the years. 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 (inaudible) than anticipated. And then by the time that I left, I was pretty proud of it. 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 get things 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 then you’re doing really well in terms of traffic and audience. What are those numbers like?
You can tell that I’m no longer 24 because my brain is going in the reverse gears to find them. We were probably doing around a million pages a month, I think, when I left. Somewhere in there. That’s within 15% of correct in either direction, somewhere in there. What was really exciting about Crunchbase News, what made it such an edifying project to work on, was twofold.
One, the people I got to work with on my team were amazing. I loved them. I’m still close with nearly all of them. 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% in a month, but we grew by 15%, almost every single month.
And so there was this compounding effect to our efforts and this, this pushing forward. We set records six out of seven months, we set a consecutive record. It was just this never any push forward. That was great. I missed that feeling of working with a small team towards a near term goal. It’s really, really fun.
Somewhere in there we also had a little podcast and we had syndication deals with Yahoo Finance, and we were on Smart News. We had other places where we drive 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, right? If people could get millions of page views to their website every month, holy shit, would 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, 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’ve gotten a much bigger job than I knew what to do with. That’s why they call it growth, I guess. The second step was to figure out where we want 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. The news team at that point it was me, right? So it was news team, singular me. I had to get a blog up and going.
The first thing I did was work the agency, got a design put together and got a site on the internet, picked up a couple of crew from the old Mattermark days that I 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 the audience react to? What is a Crunchbase reader? who currently knows about us? To me, at that point, it was a blank slate in the best possible sense, a blank canvas.
You can go forth and draw on it. 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 the way that other publications weren’t. We tried to let our personalities sit out there a little bit, so we didn’t seem boring.
We weren’t trying to be writers with the AP in the startup world. We didn’t want to do that. Tech Majority 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 our initial goal. 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.
We hadn’t found that audience and I didn’t want to be like, “That flopped do it again,” but that’s what I had to do, but only I knew. Then later on, of course, analytics were entirely open to everybody and everyone got to see everything. So that was a short, 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. I don’t want to let my answer color other people’s perspective too much because what Crunchbase wanted, the corporation, they 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.
That’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 standard publishing metrics, page views, follower accounts, newsletter 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. Newsletter subs is a great one, newsletter open rates, CTRs, all that stuff, but it just varies based on our near- and medium-term goals. It’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 home page and there’s just hundreds of stories and infinite scroll, you’ve got a newsletter sign up box and you’ve got like 10 different newsletters you could sign up for.
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 or first readers from when you haven’t really made a name for yourself?
Great question. 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 a hundred people, but that channel tops out pretty quickly and it 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.
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 grist that people want, so Google serves it up. People want to be informed.
And I think that’s why news content or news-y stuff, journalistically stuff, for lack of a better phrase, does have constant market impact because people have the thirst to know what’s going on and be informed. That same sentiment applies to a lot of stuff that I read in the SaaS World about.
What SaaS metrics should you hit? What should your LTV to CAC be in 2020? People will read that because they’re desperate to know. Similar emotions play different target points if you get what I’m saying. Search is gigantic. Then from there you get to do more exotic stuff.
Like for us, our partnership with Smart News was a long time coming. We rebuilt 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 layered on top to build out our distro (ph), grab new eyeballs, and try to reach new audiences with writing that we were proud of. By that point we had we had an artist working with us, we had lots of custom art that we were doing. We’d out our branding, and we’d figured out our logo, and we’ve really reached a nice state of equilibrium that I was pretty proud of.
So let’s go 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 is teaching people how to code will create all sorts of cool graphics that are easily sharable or retweetable, or they’ll 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’d watched the growth of Morning Brew, ever. They’re that newsletter group that’s been –
I love – 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 like 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 brand. So if you’re looking for a good example, go look at that. We didn’t have someone who was like 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, I don’t recall what it was back then.
We had some basis from which to stand on and because journalists followed me, other journalists in the field, they would often retweet us and so that would help broaden our reach organically. So we were 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, though 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, really basic shit. It’s all hard, it’s all slow. It does compound. The first one’s the hardest, but you can’t not be present in those areas out there.
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. Maybe I wrote that one article and it got 200 retweets and it was amazing, but like my next article was a complete dud.
Right. It doesn’t seem like there’s any connection. 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 Jason Lemkin?
I do. Yeah. SaaStr guy.
SaaStr guy. I love Jason. Jason was fantastic. He answered questions on Quora forever. He’s done like a bajillion Quora answers and he’s done a bajillion emails and he just, 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 published an article and it flops. I’m like, “Oh, I’m over it. 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. Right? And he’s managed to build attention on the back of technical SaaS advice and company building stuff. When it comes to keeping at it, he’s the North Star in the startup world for what happens when you just don’t give up. So you don’t have to take my word for it. He’s done it.
You can 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 Twitter account, whatever it is you’re trying to get them to pay attention to because you’ve provided them something they didn’t have.
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. Write 400 things, go viral a bunch. Then you’ll 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 Crunchbase News and that it pretty much every large media organization does, is you 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 got to mix it up.
There’s a lot of variety and novelty there, but how do what the best mix is? When you came into Crunchbase news, there’s an infinite number of types – you could do interviews with people, you could do investigative journalism. How do what’s going to resonate? How do you decide what’s worth working on writing about and what you want to avoid?
Well, the good news is you get about – I wrote, I think it was a couple thousand pieces for Crunchbase News. I think, total over the couple of years, no, it would have been at least a thousand. Somewhere in the four figures anyways. So I took a bunch of ad vats (ph) to tinker with that and figure out what it was.
You end up figuring out, if I write this, it’ll probably do pretty well. I’ll write some of those. I think this person on this 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.
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. In every newsroom, there’s some form of a regular get together to talk about ideas, trends, changes, interviews, and something like that.
So you just have to do that process. Now, of course, the world of journalism is going to be different than the world of building content to support a SaaS brand, but there’s going to be similarities, and this is one of them. Then back to our point of analytics, that will guide you a little bit.
If you only want to do things that are highly successful, you’re going to struggle because it’s hard to have repeat successes. 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? Maybe you had your meeting of the writers. You said, “You know what? This works really well. We should do more of this.” I’m just curious what that process actually looks like, something specific.
Sure. We call them explainery 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 that’s too late. If you don’t know what’s going on. Or how does ratchet work if you get a down round and you’re getting a rescued 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.
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 beast talk entitled “How to read an S1” the IPO filing document you give to the government. That’s still doing numbers, I presume, over there. It was when I left. Did it take forever? Yes. Was it worth it? Of course.
We mixed in those with our news stuff, longer and shorter form. We thought about content in short and long increments depending on what you were working on. Then we tried to build intelligent channels.
We launched a weekend email newsletter for a few people, and we let that have its own personality. You just tend to expand and so forth. 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? You’re like, “Hey, this trend works well reliably, explainery articles get more traffic and have a longer shelf life than other articles.” Why not just do a hundred percent explainery pieces?
Well, you’ll run out of stuff to explain and you’ll get sloppy and you won’t have the best ideas. 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’re using images and art. And we did a good job, I think. But it took a lot of time. That’s not something you can do every day, back to our point about regularity, it would just be impossible unless 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 wanted people to show up, so we always had stuff going up, but it wasn’t always the longest stuff. You don’t always have to do that, but you raise a really good point though.
Because people are always looking for a hack to get around doing the work when it comes to writing. I don’t think there is one, unless you’re super famous. If you’re super famous, anything you write, people will read because you’re super famous. Most people aren’t, I’m not, you’re not. You and I aren’t even 1% of the way to super famous, thank God, because that’s a miserable life.
There isn’t going to be 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. That’s what Uproxx and all those companies did. They were like, “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 a super viral gossipy article trick and then maybe a media organization is just like five or ten of those and that’s all you need.
Well, one, I wouldn’t call them tricks. I would call them huge investments of hard work. To me, trick implies that I’m doing something to confuse you. I know what you’re saying though. We never did the gossipy thing. 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 and 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. That went okay. But I think you 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 structure. I’m also talking to people at a time, like I’m talking to another VC this afternoon and I’m going to have a bunch more notes about that. 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 sorta 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. Writing every day, consistently, is a pretty hard quote, unquote, “trick” to pull off. There’s no shortcut to doing that.
To be clear, though, Courtland, I don’t want to do anything else. This is the job that I want. I don’t want to sound overly pessimistic about it. If you enjoy writing, if you’re very full of shit like I am, it’s lovely. I can see the 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 to even structure a small journalistic organization?
So the way you said that, it’s really funny. Like what if you want to run a marathon, but you hate jogging.
How do you hire a pinch marathoner to run in your place?
Well, in that case, you just, 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 because I don’t actually really know how to 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, and it needs to breathe.
It’s going to be generally aligned. You’re not going to have auto parts, eCommerce Company and a publication about how to make grits. That would be strange. It’s generally aligned, but then let them have space. Let them breathe, let them walk free.
Just have some really clear metrics you want them to hit and then fire them if they fail. It’s not super hard. And given the number of people in the media world who have been laid off in the last 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.
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’ve put that link there because we would’ve had 0.02%, more click through rates. 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 the two?
Well, a world of difference, really. So anyone could 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. As long as you don’t get sued 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, 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. 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 conflict of interest stuff like Crunchbase, couldn’t say, “Hey news team we want to land a deal with so and so, 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 a point of the show – as we could.
It was my job to hold that up, so we could proudly call ourselves journalists without any wink or diminishment. So that’s harder than probably what 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.
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.
I’ve noticed, as you said, there’s been so many layoffs and that’s how I realized this trend of journalists have a ridiculous number of followers, just going on Twitter, seeing journalists who 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 can tell they live on Twitter all day and they’ll have 50, 70, a hundred thousand followers. And it’s actually surprisingly inexpensive to hire a really good journalist. It’s like 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 like, you and I both have friends that work at like big five tech companies and you and I both know what mid-level engineers make for, 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 couple because people need to eat. I think 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 journalism background and they’ll do well, to be clear. But if you want to build a more serious, slightly distinct media outlet for distinctly 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 has 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 then 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. 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’ll give your work a lot more cohesion.”
I think it’s 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 and writing from that lens. 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 the Camille ran it, was a tremendous example of what you’re saying. They brought First Round Capital lots of attention.
I heard about the First Round Review than I heard about the First Round Capital. Tomas Tunguz over at RedPoint has built a personal blog that everyone reads in the world of SaaS. He now has brought an enormous halo effect to his employer, which is weird, normally goes the other way around.
But it just goes to show you how, when done well, and when done correctly, this stuff is as an outsized impact that can change not just a personal life, but also business trajectory, it’s just 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 can tell me, “That’s bullshit Courtland,” or “that’s actually very important and you should do this.”
Oh, this is going to be so much fun. You talk and I’ll just shout 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 and nothing but educational stuff, but if it’s not related to anything going on in the world, anything that’s happening, I think people are significantly less likely to share it and to 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. So 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, the topic that people are searching for, or looking forward to 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’ve been evergreen. You can always write the evergreen piece anyway. It doesn’t preclude that. You’re not 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 new hook for something. It’s a good point and I think you nailed it.
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 Tesla’s car crashes into semi while in autopilot mode, whatever the thing that just went, bang, boom crash, or sword, whatever that is, is the news hook.
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.
I think correlated 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 gonna net you more traffic than writing about something obscure that people don’t already have a personal connection with or a personal opinion about.
How much do you think about, I guess, the familiarity of the subjects that you write about when you’re leading a media company?
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 live 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, judging the standard or quality at the same level. You can’t let that diminish just because it’s traffic generating.
That’s said, I do love to see the numbers when I do cover Tesla. It’s a lot of fun. I think you’re otherwise right. I would just say like, there’s never going to be one thing you can do exclusively and have it go well. But I think that stuff is a great thing in the mix. Like have you ever had trail mix?
Peanuts and whenever you’re hiking and sometimes you grab a whole handful and it’s all nuts and sadness and then like your next handful is like all M&Ms? Sometimes you’ll go a bit more in the newsy, famous people direction. Sometimes you’ll go a little more into the niche stuff. Sometimes I write stuff for a week and no one cares about but me.
And that’s fine. I know that going into it, but it doesn’t attract to what I write different people in smaller quantities who I stick with. Like, I’ve met a lot of VCs by covering more niche SaaS topics who I now can just call and get their take on stuff than I would have if I had written higher level, more celebrity focused stuff.
Business celeb is like covering Mark Cuban or 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 the 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?
Oh God. Yeah, news freshness matters. And so if you’re going to cover a news item straight, “Courtland buys Ferrari drives it into tree.” That’s a new story. That’s a headline. If you’re going to report just that you need to be quick. But if it’s, “Local Ferrari driver crashes car, continuing pandemic of reckless driving in and around town X,” then you can write that a week later and you can frame it around a broader context, 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, and get some quotes and build around that to provide some more context and analysis.
That’s one way that I approach this. But breaking news matters because people give a shit. 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 need if you’re selling ads or selling subscriptions. Whatever your business is, media or not, people showing up does matter. 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 hook or 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.
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, right? 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 was not just the lovely people who I’m so lucky to get to work with again.
Because most of the stuff is the same as it was when I was here before. But it’s the autonomy. TechCrunch is more of a very flat organization. So we do a lot more like intro writer collaborations versus top down playbooks.
So it’s not like we have a three-point plan like, “Oh, X happened, you’ll do this, you’ll do that, and 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 corporate publications almost never talk about is just this word story. If you think about just like plain facts. 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 and never will kill journalism is because 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 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 or two to a box. You can’t only use a hammer to build the house or it’s gonna be a really weird ass house. So building context and walking people through why something matters is very important. And just to bring it home to what I do is, I cover a lot of the late stage startup market and I covered the IPO market and a little bit of the public markets.
One of my jobs is to explain to people what’s going on between the two to walk them across the divide as IPO is happening and that sort of thing, to explain what the hell is going on for startups and in the exit market for IPOs, in the private markets, and 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 have the connections that you’re drawing because you’re in the zone, covering all this stuff.
I think it’s a very, very important part of building a publication. 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 easier and much faster, as well. You end up being able to write relatively quickly stuff that would take other people a lot longer. Delve walk people through the news hook, through the facts and into the context of my (inaudible) their life, their startup, whatever it is.
And how important is it to own the story? Because the story is like completely subjective, right? 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.”
Someone else might look at it and have a completely different conclusion. 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. We’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. I have my own narrative, my own theme for what’s going on and talk about this for months.” And you often see this with, for example, Ben Thompson of Stratechery.
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 does 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 and 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 at Stratechery, and I read Stratechery here and there. I used to be a subscriber that I’m a fan for lack of a better phrase. Guy’s really smart. And he uses these images very well to help build on top of this text. I think it’s quite well done. He sits usually a level up from everyone else who are analyzing more discreet news events.
He’s built essentially a, one-of-a-kind media company. So none of this 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 – I can envy it, if you will.
So 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. So 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, your brain is switched on.
I don’t think you can get too far away from the facts and the facts are the grounding elements of what drives coverage. Like people are covering Robinhood because it’s growing so fast. Robinhood could have done some PR tricks and they could have done some cool things to 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. And so we will all cover Robinhood’s growth, it’s monetization, the good stuff, the bad stuff, but they’ve become a place that you can’t not go. And I think, I think that’s when the uniqueness factor comes in. And what can you bring to the table on a story like that, that’s particularly good and interesting.
Bloomberg today, as we record this, I don’t know this is coming out, wrote a really great recap of Robinhood breaking some news on some investigations that they’re under. That’s a new fact that they brought in and Robinhood 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. So 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. I spend so much of my time looking at this stuff and seeing what’s going on and it’s part of why I wanted to talk to you. It’s like, well, 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. So for example, you could say that you can’t not talk about Robinhood, which certainly seems to be true.
It’s like a huge topic, but it’s also in part, a huge topic because media organizations are choosing to talk about it. And if, for example, someone wanted to talk about my employer, Stripe, well, there’s lots going on at Stripe.
It’s one of the fastest growing tech companies, but it’s not as exciting. It’s not as consumer focused, so it doesn’t get as many articles written about it, but it seems to be like 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.
And so 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?
I think it’s a big part of my job because the last thing you want to do is to send into Generika. You don’t want to become exactly similar to some other publications. You don’t want to lose any angle on the world. You want to bring something that other people aren’t otherwise, why are you doing it?
With the internet distribution’s free, right. So it’s wrong to write the exact same story about X or Y who really cares? But some traffic – not really. Traffic, as you and I both know in the ad game is not super valuable. When it comes to Stripe though. I mean, Stripe is pretty well covered for an enterprise company, for a company that sits in the background.
They do a pretty good job of bringing attention to, I guess, 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 like 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 SaaS product. They’re like not a millionaire 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.
And that’s just a struggle of news businesses economics going to hell and the industry falling apart. Back in the day there were like a multiple of the number of journalists in the world that we have now, at least in the U.S.
And so there was more folks listening, more folks to talk to you, more folks to go out there and talk to that person with a small business and get their story. Now I get yanked by breaking big news off of smaller stuff. Just because that’s the fact of the way the world currently works.
It’s not good or bad. Well, it is bad. But it also is. So 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.
And so the tonic, the antidote to being a startup that’s ignored is just to crush it and people will pay attention to you, but that’s tough. And most startups won’t do that. So it’s 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 existed entire subset of founders building companies that are interesting to lots of people, but maybe not broadly interesting enough to get mainstream media coverage.
Like TechCrunch is not going to write about someone who just got to $10,000 in monthly recurring revenue. But I wish there were 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 the 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 at Providence, my adopted hometown. I’m trying to get to know people that are building smaller stuff, but I mean, 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.
And so 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 and I have a bit of a personal readership.
A couple of people read my stuff just because I wrote it. And so 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, but I’m sympathetic to what you’re saying. I don’t have a solution for it other than fix journalism’s economics, which will help. But I mean, if we can pull that off and I will 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 role from writing for a bigger publication?
Everyone’s had that thought in the same way that every engineer working in a team for an idiot, who’s been like, “I can just go build this myself. Why don’t I just go, I can just get my friends. We can just launch our own company. We can build our own product,” like the indie hacker thing, right.
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 paternity leave sounds great. And I’ve got good health insurance. And my wife is in residency, so I make most of the money. So, I’m sufficiently old that my life has 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 TC. I just got back. I’m super happy. I’m getting to do a lot of stuff I’m excited about. I love the people I work with, But, in five years, probably, yeah. If Substack is still popping in five years, I’m in. It 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 have already jumped in the pool. They’re very brave and I’m proud of them.
And 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 a big company is somewhat easy. You get a raise every year. You get a 401K match, there’s things that you get that are nice.
Yeah. I think the risk adjusted expectation for what you can earn as an Indie Hackers 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 risks 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 because you have some other things, right? Like if you can’t keep, for example, if you can’t work for an employer, there’s something inside of you that just hates doing it, which is the case with me and a lot of other people, then it gives you that extra oomph. But if you’re killing it at your employer and you love the benefits that you get, I don’t think it makes sense to financially to jump in the pool as an Indie Hacker.
I mean, unless you just can’t take it anymore. Right?
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. Not like ignorant, but like stupid. “Oh, you were working at Google.
You were like mid-level. You’re probably pulling down 350 a year and now you’re going to off and go start a company. Great, good job, now you’ll invest all that stock you had waiting for you. But I love that. I love that the 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 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. I mean, like I’ve had people get so hyped about like healthcare APIs. 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 them a better place and hopefully a pile at the same time for themselves. 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 can read in a day. If you don’t like one particular article, why pay for it? Why even read it?
You can 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. It’s already in Indie Hackers.
Yeah. But there’s already a TechCrunch and Adventure Beat and a bunch of other publications. So there’s plenty of room for Crunchbase News to show up. 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. That’ll be a good sniff in the direction of where you should go. We are Crunchbase 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.
Like at one thing that I don’t like reading is like a trend piece. Like, “People in New York City are wearing this type of thing.” And I’m like, it’s five to seven people and the author’s friend. I don’t care. But if you bring data to me, you said, “Look, it’s up 30% over the last two quarters, up a hundred percent from last year,” I sit up. We took that approach and that was our angle.
But if, 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, I’m not interesting 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 is just so big. You won’t be a hit maybe, but you’ll have a good steady (inaudible) 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, how do you structure and actually write a story on the internet. Obviously on the internet people are pressed for time. They’re checking their email. They’re on Twitter. They’re usually in some distracted state.
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, like 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 a Twitter.
How do you approach actually structuring a story? And 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. 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 the next to them (ph).
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 the 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. Like 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 an annoying style and I’ve given up trying to fix it.
This is just 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 you can sit down occasionally and chat things through.
You’re gonna 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 could be your mom. If she’s got the time. It doesn’t have to be someone fancy or famous or good. Just someone who reads can provide some good feedback where they got lost, where they needed some more context that this happens to me.
People will be like, “We need another sentence here. You just, you jumped.” And I’m like, “You didn’t follow my logic?” They’re like, “No, I’m not in your head. Add a sentence.” I’m like, “All right.”
So that’s about it. And then you can also imitate respectfully people that you, that you read and like. You’re not gonna start writing Ben Thompson length essays to start. You can go find some people be 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 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 and writing groups, if you want to go super deep. But people listening to this probably don’t, but that will get you started.
So I’m trying to distill everything we’ve talked about into a 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’ve 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 gonna get a lot of shots on goal. You’re not gonna 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 corporate very clearly, 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 hard, but you need to understand that, like these should be two different things.
Yeah. It’s hard to have the two personalities but keep going.
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 the Bloomberg Way, their actual book, but a lot of it can 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, 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 uncover what’s not being written about and have your own unique angle.
Are there any major things that we’re missing here? 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?
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 fires up an entrepreneur is going to be necessary for this work, because while there’s plenty of room on the internet, there’s also plenty of competition and 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 in this situation. And then I would add one more thing. Have some fun. Writing is good. Being part of the conversations is enjoyable. It’s one of the funnest things that I’ve ever gotten to do as a person.
And so, 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 to 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 this stuff yourself. So, 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 again, 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.
I should go check Slack. What we’re talking about, panic.
You’ve got stuff to do. 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/Alex is my main social presence. My email is [email protected] I’m usually between one and seven days late on email. So apologies for that. Life is busy. I write for TechCrunch.com. You can find myself around there. I’m also on a podcast called Equity, where we cover the VC startup worlds, which is a blast and one of my longest projects that I’ve been part of, one of the finest as you know, Courtland. The podcast is just a blast. It’s never, ever a boring time, but really, I’m around to help if I can be of use, shoot me an email and try to get back to you ASAP. Time is limited, but I will try to answer whatever questions I can.
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 indiehackers.com/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.
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