A friend of mine was at a party here in Austin recently, chatting with a data scientist from Medium about AI-generated content.
“Technology can’t really detect it yet,” was the basic gist, “but humans seem to be able to.”
Fascinating.
What this person meant, I gather, is that any individual human has barely a coin-flip’s chance of spotting AI content. Tech isn’t much better yet. But if you step back, and look at how large groups of people interact with human- and AI-generated content, it’s different.
In other words, it sounds like data teams are finding novel ways to detect AI.
II.
There’s been a lot of debate over whether platforms like Google will punish writers for using AI once they can reliably spot it.
My opinion: Of course they will.
So far, most platforms have taken a relatively soft stance, advocating for “the appropriate use of AI or automation,” as Google puts it.
I see some people interpret this as though Google is indifferent to or even supportive of AI-gen content.
But I think the smarter interpretation is to view this as a “tactical retreat.”
AI has the ability to completely undermine the trust and utility Google has built with users. They have a strong incentive to control its appearance in search.
But they can’t reliably detect it yet. A stronger policy would be meaningless without the ability to enforce it, so it looks to me like they’ve traded space for time while they hone the systems needed to deal with this new technology.
Once those exist – and they will – I believe we’ll see platforms like Google get much more bold about cracking down on AI content.
III.
Medium offers an interesting example.
Early in 2023, they updated their terms to say that they, “welcome the responsible use of AI-assistive technology,” so long as writers were transparent about it.
Later that year, as they got a better feel for the negative effects AI had on users’ experience, they took a firmer stance:
“Medium is for human writing, full stop,” they wrote. AI augmentation would be allowed – technically using a tool like Grammarly counts as AI augmentation – but not welcome.
Humans were the priority.
Behind the scenes, they’ve put enormous resources into refining their distribution system to limit the reach of 100% AI-generated content.
Fascinatingly, that has meant re-introducing humans into the loop. Their boost program uses two layers of human review to help decide what gets increased visibility on the platform.
Then, a couple of weeks ago, they came out and said that any partner using AI in their paywalled content – disclosed or otherwise – will be removed from the partner program.
IV.
So what does all this mean for you?
There’s no doubt AI plays a role in the future of human creativity and content marketing. Personally, I enjoy Brett Hurt’s take on this – something he’s calling Renaissance 2.0
But never forget the incentives of the platforms.
Their goal is to serve up the best content for end-users. Full stop. So experiment with AI, but only to the extent that it helps you create stuff that’s better than what’s out there now.
And be careful not to get over-invested in it.
More than one great company has been killed overnight by Facebook or Google choking off distribution. And as platforms find new ways to spot AI content, they’ll be bolder about eliminating it.
I’m not sure what it was. It’s not like I’m not busy enough already. But I just signed up to run the Lean Horse Ultra Marathon with my friend, Sam – 50 miles through South Dakota hill country – four months from now.
This is by far the longest race I’ve run.
The last ultra I did (which was also the first ultra I did) was 50km or about 31 miles. It wrecked my legs and feet, and this adds almost a full marathon to that.
I trained for that first race, from a base of zero, in eight weeks, and finished second-to-last, just under the cutoff time.
This time, I want to do better, and with four months to prep, I’m confident. Here are the things I’m going to do differently:
1. Training My Feet & Legs
Last time, I cobbled together a simple training program from two different chapters of the 4-Hour Body. It essentially looked like this:
400m sprints 2-3 days a week
1 day of long, slow, distance (10+ miles)
That’s it. There was lots of rest involved, and in the entire run-up to the event, I don’t think I ever ran more than twelve miles.
It worked pretty well. I think I missed like half of my planned training sessions, and I was still able to finish the race. But I was slow, and I really hurt my feet.
This time, I’m taking training more seriously. Part of it is out of respect for the other competitors. And part is because I want to perform better. Sitting here at the outset, the things I think I want to change would be…
Add heavy compound lifts 1-2x per week
Barefoot slow jogs to strengthen small muscles in feet
Maybe do a 50-mile walk 1x per month – just to get used to covering that distance mentally
2. Diet
I was too heavy for that race. Probably 185lbs or more. I should be competing around 165, so over the next few months, I’ll be focused on leaning out.
Big things for me:
No drinking calories – That means skipping the alcohol and lattes. I like black coffee, so that’s easy. Ditching diet sodas too though even though they’re zero calory.
Don’t cook in butter – Personally, this is where I get most of my hidden calories. As soon as I cut it, I lean out pretty fast.
Avoid processed carbs (mostly) – This is my big weakness. Not really interested in cutting it entirely (especially since I’ll be in Connecticut in the summer – home to the best pizza). But would like to take it down to maybe one meal a week.
3. Focus on Recovery
I don’t have an ice bath or anything fancy like that. Just going to focus on getting to bed early, and spending at least 8 hours there.
I’ve been running for fun the last week or so and track it on a Garmin watch. Seems like my performance only improves on days after I get to bed early.
Last Thing
I remember what it was now – the thing that made me do this. A realization I’ve had over and over in my career: I accomplish more when I have more going on.
I yearn for the opposite. For a clear, open schedule with lots of free time so I can finally focus on the work I want to do.
But the reality (for me at least) is that I do that work more reliably when I don’t have all day. And being busy, pushing for new things, keeps me reminded that I’m capable of more.
I got this really nice compliment on my Austin newsletter from Jason Scharf this week 👇
This was a big deal for me for two reasons:
Jason runs the AustinNext podcast. He knows everyone here in town and is super tapped-in (a.k.a hard to surprise)
My entire “growth plan” so far has been to focus on making the content so good people like Jason talk about it
This was a really nice indication that the process is working, so this week, I thought I’d write about what that process looks like at a high level each week, and the five tools that are crucial to my work right now.
This isn’t just for local newsletters…
It’s more universal, and should be useful no matter what kind of newsletter or community you’re building. A lot of it, I learned at The Hustle, then brought with me to Hampton (where our weekly active members stayed between 85-90%).
Now I’m using it in Austin too, because it works.
You’ll recognize the names of all five tools, but I use them in ways you might not expect (that’s literally the only reason I thought this might be worth writing).
We’ll get into them in a second, but first…
Let’s Talk About Mindset
The tools I use are less important than the mindset. And the mindset is centered about community-building.
I want people to think of the newsletter as something they’re a part of, and want to interact with each week.
What are people looking for in a professional community? There are a lot of things, but generally, you can boil them down to these three must-haves:
To meet someone interesting
To learn something interesting
To feel like they contribute
Whether you’re building online or in-person, it’s always the same. Miss any one of these for too long, and people will drop off.
I’ve talked before about how to write stuff no one else can. The main point of that piece was that you can cultivate an information advantage as a writer, simply by talking to people who are often overlooked.
This piece takes that one step further, with a few tips that’ll help you put yourself at the center of an information web that’s hard for anyone else to replicate, and helps deliver on the three must-haves above.
So let’s get into that…
1. LinkedIn Sales Navigator
I pay $100 a month for a membership to LinkedIn Sales Navigator just because it makes it easy for me to find interesting people to follow online based on criteria that I want.
For example, here in Austin, I’m building a business newsletter that shares events and insights from fascinating people around town.
The process is pretty simple – find fascinating people, and follow them, curating the best insights they share, and adding some personal opinions and research on top.
Not just the famous people in Austin (remember, one of our goals is to introduce readers to interesting people). We have to get off the beaten path.
Sales Nav makes this easy.
Not only can I pull a list of local founders in seconds, but I can also see from the dashboard who’s actively posting on LinkedIn and might be worth following. The list stays updated too, so as people either relocate here, or change their info the match my search, I see ‘em.
So what I do is I keep this list, and when I have spare time throughout the week, I peruse it looking for new voices worth following.
I go deeper than you might expect. If someone appears here but doesn’t publish on LinkedIn, I’ll check for them on Twitter, or look for a personal blog.
I check out their company site too.
I think of this as a process of ongoing discovery – continually finding new things to be interested in and write about. So don’t rush it. You’re never really done.
2. Twitter Lists
For god’s sake, don’t use the native Twitter feed if you’re trying to get any work done. It’s a hellscape of distractions.
Instead, pick the people you want to pay attention to, and put them in a list. Then save a link to that list in your bookmarks bar so you can get to it without ever going to the Twitter homepage.
Not only do you avoid the distractions of trending topics and recommended posts. But you’ll get to scroll everyone’s tweets sequentially – no algorithm filtering. So it’s much better from a content-curation standpoint, because you can be confident you’re actually seeing everything people are saying week to week.
It automatically surfaces the most popular tweets for any profile you land on
It blocks the “Trending Topic” sidebar – you have no idea how good this is for your brain
3. My RSS Reader: Feedly
Even if someone publishes on LinkedIn or Twitter, they’ll often share more in-depth ideas on a blog or newsletter, and so I use Feedly to keep up with those.
If you don’t know what RSS readers are, good! The modern media industry would basically wither and die if readers ever caught onto how great RSS is.
Okay, fine… I’ll tell you. It’s basically a custom social media feed.
You can subscribe to newsletters, blogs, social media channels, and more, and have all posts pushed to one central location, organized, even highlighted or summarized with new AI features.
Basically, you get all the info you want without the attention-grabbing algorithms or incentives of big social. It’s also easier to unsubscribe from stuff, because you just nuke the individual feed for that source, rather than hoping they take you off their list.
So anyways, RSS is great.
I keep two different lists. One is for official publications here in Austin (newspapers, culture magazines, that kind of thing). The other is for personal blogs and newsletters of specific people in town.
Pro Tip: Often, when someone signs up for the newsletter, I’ll check to see if they publish stuff online. If they do, and it’s a fit for the newsletter, I’ll add them to my RSS feed and keep an eye on their work.
I like to shout readers out as often as I can. It’s fun, and also helps give them the sense of contribution I talked about earlier.
Every morning, I get up early and my first 1-2 hours looks like this:
Go through Feedly skimming new articles
Scroll the last 24 hours on my Twitter list
Scroll my LinkedIn Feed
Because I continually add to all three of these whenever I find new sources worth following, the quality of the stuff I’m able to surface continues to improve over time as the “information web” gets more and more unique.
4. The Drop File
I talked about this in my community newsletter playbook, but one of the most important tools I have is a simple, ugly, Google Doc that sits in my bookmarks bar.
As I sit down each morning, and throughout the day, if I come across anything that might be an interesting fit for the newsletter, it gets dropped in here.
Then, when it’s time to write, I open this file up, review what I’ve got, and pick from there.
Shout out to Steph Smith who taught me this
There are a lot of little things that go into writing a business newsletter week after week. You can’t reference the same person too often or the content becomes too obvious and easy. You want to have a good mix of men and women highlighted. A good mix of industries too.
It’s hard to just sit down and write that off the cuff.
Having the drop file makes it easier to pick from a buffet of ideas and get the kind of blend that I’m looking for each week. It also lets me develop longer stories over several weeks, collecting material passively until I feel I have enough to write something.
5. Time
The final tool – this stuff takes time. I probably spend 10-15 hours each week just reviewing these feeds, exploring, and being curious. And I think that’s kind of the main advantage I have in finding things that surprise people.
It’s possible to make something people enjoy reading in less time. But it’s hard to build deep knowledge of a topic, and that’s my real goal here.
So many people are trying to shortcut the writing process these days. They look at an article like this, and their first thought is how to use AI to replicate what I’m doing in a fraction of the time.
I don’t worry about them at all.
To whatever extent I’m able to set myself apart from competitors, it’s largely because I’m quite happy to spend the time doing the thing that we’re here to do. The newsletter isn’t a path to something else.
If you feel the same way about your work, I think you’ll be just fine, as long as you know how to monetize well.
Quick Wrap-Up
Okay, so to review, there are three things that great content and communities need to offer:
New people
New ideas
A chance to contribute
I use tools like LinkedIn, Twitter, and Feedly to continually surface new people and ideas to share with readers.
I also use those same tools to follow my readers, so their work sometimes ends up in the newsletter, which gives them a sense of contribution.
The drop file keeps everything trapped in one spot so it’s ready for me when it’s time to write.
And time is the secret ingredient that allows me to dig deeper than readers or competitors could on their own. It takes everything above, and dials it up to 11.
Most of the time, when a writer starts to feel bored, it’s because they’re writing what they think they should write, rather than what they’re actually interested in.
Led by obligation, rather than curiosity.
We got some experience with this at Trends. People paid $300 per year for the newsletter, and we felt pressure to deliver the same kind of newsletter every week. But you can’t pull business opportunities out of thin air just to fill space.
So over time, we developed a rule: If we’re struggling to fill a segment, cut it, and see if people scream.
It’s a concept I got from Andy Rachleff, the man who coined the term ‘product-market fit.’
“At the end of your free trial, you should pull the trial,” he said. “If the customer doesn’t scream, you don’t have PMF.”
If we were struggling to fill a segment we thought needed to be there, we’d cut the segment entirely, and see if readers screamed.
If they did – if they wrote in asking where such-and-such was – we would put it back the following week, and make sure to prioritize it in the future. That’s how you know you’re making something people care about.
But often, they didn’t complain at all. Because cutting a “meh” segment gave us time to focus on stories we actually cared about, and made the newsletter better overall.
Your readers don’t need you to deliver the same format every week. They need you to deliver the same feeling. Your authentic voice will typically do that better than something you feel obligated to write, even if it ends up being much shorter.
My favorite example of this comes from The Hustle…
A daily writer once called out sick, and all of a sudden, Sam needed to get the newsletter shipped on his own.
What did he do? Cancel all his meetings, and draft a perfect email?
Not quite.
This is what he sent that day…
That’s it. That’s the whole thing.
People loved it.
It’s honest, in a surprising way. Because the truth is that he was busy and he needed to get back to work on other things. But more importantly, he didn’t try to fake interest in a bunch of random news stories and force himself to write a typical email.
He took an authentic emotion, and turned it into something he could share with his audience.
I think of this often.
My newsletter always feels like work. That’s because writing’s hard. It should feel like work, in the same way that going to the gym feels like work. Work you enjoy.
But if it ever feels too much like an obligation, I take that as a signal that there’s a gap between what I’m writing and what I actually care about at the time.
To close the gap, I’ll sometimes spend a few minutes free-writing. Either I’ll write about what’s making me mad right now (no stopping, no edits) or I’ll just set a timer and write non-stop for ten or fifteen minutes about whatever goes through my mind.
Usually, one of those gives me a thread I can pull. It’s hard to write for ten minutes straight without tripping over a thought you’re genuinely interested in.
“Excited curiosity [is] both the engine and the rudder of great work,” Paul Graham once wrote. “It will not only drive you, but if you let it have its way, will also show you what to work on.”
So if your newsletter’s feeling like a chore, rather than something you can sit down and enjoy making, stop for a second and ask yourself what you’re actually excited or curious (or mad) about these days.
Write about that.
To hell with your typical format. Just make sure you’re in it.
Yesterday, I sent the ninth issue of my local newsletter – the one I plan to grow into a 6-figure business – and as of right now, that list is sitting at 96 subscribers.
Sound low? It probably is a little bit, but based on what I’m seeing so far, I’m optimistic this is going to work. It just needs time.
Without going too deep into it, the quick reason is that I’m building a high-value audience, engagement is strong, and I can feel growth getting easier. But still, it’s a big difference from the other big newsletters I’ve written for in the past.
So today, I wanted to talk about the early stages of growth, and how I stay both sane and motivated while getting the ball rolling on a small list.
We’ll dig into…
Real talk on growth charts
What a good growth rate is
How to think about the value of your audience
Why shortcuts can be a mistake
Getting through the early days
Oh, and this is going to be relevant if your audience is big too. Growth is relative. Even when the list is big, it can feel like a slog sometimes. I formed a lot of these views while working at The Hustle, and while studying newsletters of all sizes across the industry.
Let’s dive in…
Real Talk On Growth Charts
I’ve been working on newsletters professionally, and studying them closely for almost half a decade. I’ve seen a lot of growth charts.
At this point, I can look at a chart and pretty reliably guess how someone is growing.
Organic growth looks different than paid growth. Paid ads look different than SparkLoop. Etc. There are still surprises every now and then, but for the most part, these things grow in somewhat predictable ways:
Organic growth tends to be fairly linear – unless you’re riding a hype cycle like crypto or AI – with random jumps when a piece goes viral or gets attention from bigger publications
If you see growth that’s both sustained and super-linear, they’re typically paying for that
It’s crucial to know this so that you can set realistic expectations for your list, and avoid comparing yourself to people who are playing a different game.
A great resource to check out is Chenell Basilio’s newsletter, Growth In Reverse. She charts the growth of dozens of different email lists, and writes about the tactics they used. Combined, those two offer a good sense of what you can expect from your list over time.
So What’s A Good Growth Rate For You?
Obviously, it varies. But there are some benchmarks that you can use as a baseline to set expectations as you get started.
In his recent interview on the Newsletter Operator podcast, Adam Ryan, former president of The Hustle and co-founder of Workweek, said that the two big milestones for a new newsletter are…
speed to 1,000 subscribers, and…
speed to 10,000 subscribers
If you can get to 10k inside a year organically, you’ve got a real firecracker on your hands, and the newsletter is probably going to reach escape velocity.
That’s the industry rule of thumb. But there’s two other things to remember if you’re early on:
You’re going to get more efficient at growing throughout your first year (so the first few months will be much different than the 10th-12th)
The benchmark for success is gonna vary based on the type of audience you’re going after
If you write a newsletter for CEOs of 9-figure companies, that’s going to grow a lot differently than others, and you may never break 1,000 readers. But that doesn’t mean the email is worthless.
It’s important to understand the nuance of audience value…
How To Think About The Value of Your Audience
It is both easy and tempting, when thinking about the value of your audience, to focus on size over everything else.
But as the old saying goes… “size is just one of several important factors that should be considered when you’re deciding the value of a thing, and it shouldn’t be over-weighted in your decision criteria or else… you know… you might walk away from something that’s actually really great.”
…Or something like that.
Here’s the deal – if you run a newsletter, there are basically two ways you’re going to make money from that:
By selling your products to that audience, or…
By selling someone else’s products to them
This can take many forms: paid subscriptions, services, paid events, ads, affiliate deals, etc.
But at the end of the day, it all comes down to those two things – the value of your audience is determined by their ability to buy either your products or someone else’s. And that, in turn, comes down to three things…
The size of your audience
How much money they have to spend
How willing they are to buy things you recommend (the technical term for this is “trust”)
It’s great to have all three of these. But if you have two, you’re good to go. And if there’s one that’s more important than the others, I’d say it’s purchasing power of the readers, not the size of the list.
The amount of money your readers have to spend dictates a lot of other things, like the price you can eventually charge for paid products, or the caliber of advertiser you can work with.
This is part of the reason I decided to build a local business newsletter, rather than a general audience. Business owners are a higher-value audience, and in something like a local newsletter, where the total addressable market is much more capped than something like Morning Brew, it’s important to focus on high-value readers.
There are other more important reasons I chose that audience – the biggest one being that I love learning and writing about business, and interacting with business owners.
So I wouldn’t encourage someone to pick an audience just because the readers have more money (you’ll be miserable if you don’t like what you write about). But it’s part of the equation to factor in.
Why Shortcuts Can Be A Mistake
In the same interview I mentioned earlier, Adam Ryan lamented the fact that so many newsletters are using paid recommendation platforms like SparkLoop or Beehiiv Boosts to grow so early in their journey.
Historically, newsletter operators pushed to get to ~10k subscribers organically before paying for ads.
There were a few reasons for that, but one of the big ones is that in the beginning, you’re trying to find content-market fit. You’re learning how to talk to your audience, what they need, what they see as your key value-prop, and how to communicate that to others.
When you find that, you unlock organic growth, and that in turn adds an important tailwind to paid marketing you do in the future.
One of Adam’s points was that it’s much harder to judge whether a newsletter has actually found content-market fit if they pay for growth out of the gate, especially with recommendation platforms where some portion of readers aren’t even aware they’re signing up for your list.
I’ll take that one step further…
Shortcutting that early growth doesn’t just muddy your understanding of how you’re doing. It can actually be a huge waste of time and money.
The most impressive and surprising growth chart I’ve seen came from a company that went from 0 to 10k+ subscribers in their first month by shoveling money into SparkLoop.
The founder called it the fastest-growing newsletter of its kind in the world.
Only problem was that the list was worthless. The employee who built it found a way to use FB ads to get very cheap emails for his personal newsletter, then set himself as a SparkLoop referrer for his employer’s newsletter, and profited for months sending low quality leads to his boss.
After they got rid of him, they had to get rid of the entire list too, which had ballooned to 100k+ unengaged subscribers. Six figures in ad spend down the drain because of a bad faith actor, and a little too much focus on list-size.
Dealing With The Slow Growth Days
Okay, so you know the risks of over-indexing on list size. You also know the other components you need to focus on (trust and audience quality). But how do you actually get excited about writing for a small group of people?
Here are a few tips…
1. Talk to a bunch of them
You have unique advantages when you’re small that you’ll miss when you’re bigger. For example, you can know almost everyone on your list, and get crucial insight about who they (and your future readers) are.
Talk to a bunch in-person or on the phone, and ask about why they signed up, and pay attention to the words they use when they answer your questions – you’ll start to hear patterns that you can mirror back in your landing page copy or social media posts.
2. Focus on other engagement metrics
Sure, growth’s important to keep track of. But early on, when you’re trying for content-market fit, you’ll get a lot more signal from things like…
Conversion rate on your landing page
Open and click rates
Qualitative feedback and spontaneous sharing from readers
When I say I’m optimistic that my local newsletter will work (given enough time), it’s because early feedback on these things has been strong, and to me, that’s more important than growth velocity right now. It also feels like growth is getting easier, but that’s a story for a different week.
3. Finally, pretend you’re speaking in front of them…
Every week, when I sit down to write for the audience of my local newsletter, I pretend like they’re all sitting in a room, and they’ve come to hear me speak. It keeps me accountable. I can’t be boring, or phone it in just because the list is small.
96 people may not sound like a big list. But 96 people in a room is substantial.
This is a trick I got from Jacob Cohen back when we both worked at The Hustle. He used to get everyone hyped up by comparing how many football stadiums worth of people we were talking too that morning, and I find it works just as well when working with small or large audiences.
Wrapping Up
Last year, I wrote about one of my favorite companies, Lost Art Press, which makes 7-figures in top-line revenue selling wonderful woodworking books.
During the research for that case study, I came across a line from the founder that I think about all the time…
John and I each put in $2,000 of our own money to pay for the first press run of our first book, “The Art of Joinery,” and we grew the business slowly from there. It’s a difficult way to run a business and requires a never-ending focus on expenses. But growing the business slowly ensured that it would be difficult to fail.
Christopher Schwartz
It sounds trite, but the early days really are something you’re going to want back later. Don’t rush to get through them.
On May 6th, 1835, from a cellar in downtown New York, James Gordon Bennett Sr. published the first-ever stock report based on information he’d gathered on Wall Street.
His brand new one-page paper was called The New York Herald, and it would change the content we consume forever.
When you think of old-time paperboys yelling, “Extra! Extra! Read all about it,” you’re thinking of Bennett’s work. He pioneered the so-called Extra edition, wherein papers would print more than once a day, updating stories as news unfolded.
He’s also widely considered to be the first person ever to publish an interview. If you can imagine that – it simply hadn’t been done before.
He invented the society column. He invented the stock sheet. He was the first publisher in America to be granted an exclusive interview with a sitting president, and the first to employ a European press corps, bringing unparalleled news from Europe.
During the civil war, he pioneered the use of maps to show troop movements – something we largely take for granted now.
He also had his reporters pour over southern newspapers, tallying up any mention of rebel troops or positions.
“The resulting list was, when published, so accurate and comprehensive that the Confederate war command arrested several clerks at its Richmond headquarters, on the assumption they had leaked secret documents.”
Literally the day after the war broke out, Bennett began publishing battle maps
All this wasn’t easy. These were the knock-down drag-out days of early New York media, and his opponents did a lot to try and keep him down.
Publishers boycotted any newsstand that did business with him (sound familiar?)
They refused money from companies advertising with him. On his honeymoon, they conspired to try and have his travel plans cancelled. Then later, worked hard to spread the rumor his son was a bastard.
Enemies even beat him up on the street in broad daylight (including, in one noteworthy instance, a candidate for district attorney whom his paper had put down).
None of it worked. Through his voice, and his innovative storytelling, Bennett had won the support of the people. He could speak directly to them. And they would not let The Herald fail.
“I never wish to be a day in advance of the people,” he apparently said.
Maybe not, but he sprinted ahead of his competitors.
By 1865, as he neared retirement, revenue had climbed to $1 million per year, which was as much as the next five competitors combined.
When his son took over, it would be America’s most profitable paper, and eventually afford the junior Bennett two Parisian townhouses, an 1,800-acre estate in Versailles with a palace on the grounds, a shooting estate in Scotland, a villa in Beaulieu-sur-mer with four private chefs, and a 314 foot yacht with three private staterooms just for him, each rumored to house a different mistress.
Oh… And a townhouse in Manhattan, a mansion on 182nd street, a country club estate in Newport, and of course, The Herald building itself.
It was, in short, very, very, very profitable to be good at capturing the attention of the masses. And the key to that seems to be a continual focus on innovating content.
All of this is chronicled well in a book I picked up recently, Battle of Ink and Ice.
The main storyline is about a historic dispute over who reached the North Pole first.
But it’s set against the backdrop of the newspaper wars of the late 19th and early 20th centuries, and for the last few weeks, it’s had me thinking a lot about content innovation, and whether we can lay down any firm rules on how to do that.
So far, I think I’ve found four…
I.
Sahil Bloom was the first person I ever noticed purposefully testing new content formats. Maybe you’ve seen it too – he tries different things, some catch on, then he repeats those (often with further small tweaks).
Pay attention to the dates, and slight format tweaks
Eventually, the world catches on, and people start copying.
I don’t think there’s anything wrong with recycling formats that seem to be working for other people. I’ve done it myself. BUT it’s important to realize the limitations.
I’ve never seen anyone get as big or bigger than Sahil by repurposing his hooks, and that suggests something interesting – that content formats are subject to the same “law of shitty clickthroughs” as ads.
If you don’t know the law of shitty clickthroughs, it basically says that people respond to novelty until the novelty wears off. A new ad format grabs attention, driving all sorts of traffic and clicks and buzz. Competitors copy it. And over time, people get used to it, and learn to tune it out.
It’s one reason growth teams are constantly experimenting with new ideas.
One issue with copying what’s working for other people is that by default, you’re joining further along the curve and get less time before the idea stops working.
But much more importantly, if you only copy others, you don’t form opinions about why something is working and what else might work. You’re reliant on others to keep your growth engine going.
It’s also hard to build a position as a leader if your audience notices that you’re always following someone else.
So the first rule I can see of content innovation is that you generally want to be at the front of the curve, trying new things. That will help you wring the most out of formats that hit, but it will also help you develop an opinion of your own around what to try, and that’s the most valuable part.
II.
Okay, so we agree that we should be “innovating” but what the hell does that actually mean?
Well, I’ll tell you what it doesn’t mean: It doesn’t mean you need to be completely unique, with never-before-seen ideas, and it doesn’t mean you need to be a million times better than everyone else. Trying for either of those is more likely to stall you rather than help you.
Instead, the winning formula seems to be “a little better, and a little different.”
This is where Mr Beast comes in. In his interview with Joe Rogan he talks about the exponential rewards that can come from small improvements in content:
If you get people to click your video 10% more, and watch your video 10% longer than mine, you don’t get 10% more views, you get like four times the views. You have to think exponentially.
Mr Beast
It can be hard to look at the small tweaks someone like Sahil makes – moving a semicolon here, changing a thumbnail, trying a different video title – and feel like that’s a valuable use of time.
That is, until you truly internalize the idea that small improvements can unleash enormous gains. A bit more engagement sends a signal to the algorithm that more people should see your stuff, and that snowballs.
But it’s not just about the algorithm. (Blegh, I hate the way we talk about that)
When you’re a little bit different, you’re no longer competing with everyone else. This again is why it’s better to be at the front of the innovation curve rather than further along it.
And when your stuff is a little better than what came before – a little more detailed, perhaps, or a little easier to read, a little more fun, etc. – you give the audience something to get excited about. And word of mouth will always be the most powerful algorithm out there.
III.
I swear this isn’t going to become the Sahil-Bloom-fanclub newsletter. But there’s one other important lesson I take from his recent work that I think is worth sharing.
These days, the main place I see him testing stuff is on Youtube.
He’s relatively new to the platform. At the time of this writing, his oldest video was posted just ~2 months ago.
I want you to pay attention to these view counts.
When he joined Youtube, he had over a million Twitter followers. An average tweet from him gets hundreds of thousands of views – often millions – and his newsletter list is 700k+ strong.
But on Youtube, he’s the new kid on the block.
Imagine that for a second.
Think about how hard it’d be to go thousands of likes and shares every day, to a few hundred views total. That ability – to ignore your ego while moving into new arenas – seems important to what we’re talking about here.
My prediction is that within a year, Youtube will be his biggest audience. But you can’t get that kind of growth unless you’re willing to repeatedly go back to basics.
In their book, Dual Transformation, the authors use the metaphor of a mountain range.
When you dominate a space, you stand atop a hill, and from up there, every other path looks like it heads down.
But there are bigger mountains than the one you’re standing on – emerging trends and competitors that will one day surpass you. If you’re not willing to at least put one foot on another hill, you’ll eventually become obsolete.
You have to be willing to go downhill in order to get higher.
Naval Ravikant put it similarly once. “When you look at the greatest artists and creators,” he said, “they have this ability to start over that nobody else does.”
IV.
I want to close this out by looking at Tim Ferriss for a second. I think he’s a fascinating person to learn from for two reasons:
He’s stayed relevant for almost 20 years now, and…
He tests a lot
If you know of Tim, you probably think of him as either a podcast host or author of The 4-Hour Workweek. But I’ve been following him since 2008, and he’s tried so many things in that time. To name just a few:
Ran one of the world’s top 100 blogs
Filmed 3 different TV series
Trialed a membership format
Trialed a monthly box-club
Runs a newsletter with 2m+ subscribers
TED and SXSW speaker
Wrote 5 books – including an NFT project called Cockpunch 😂
Launched a fiction podcast series for Cockpunch
Built apps for 4-Hour Body and Slow Carb Diet
Co-founded largest psychedelic research center in the world
The Tim Ferriss Book Club produces audio versions of famous books from other authors
Even within each of those things, he tests a lot of different formats, like his recent walk & talk interview with Greg McKeown (which I think podcasters will adopt en-masse as soon as someone figures out the tech to make it easy).
But most know him for just one or two things.
The lesson here is that over the course of your career, you’ll try a lot. Some of it will fail, a decent amount will be successful, and then a few things will be so overwhelmingly successful that they eclipse all your other work in people’s minds.
We don’t control what we’re remembered for. All we can control is what we put out into the world, and the effort that goes into making it better and different than what came before.
The first person who ever really explained newsletter monetization to me was James Altucher, and if you’ve seen the Newsletter Engine business model we published at Trends, it was strongly influenced by him.
If you haven’t, here’s the short version – there are three ways newsletters make money:
Free Products: Monetized via ads and affiliate deals
Backend Products: Typically start around $500 and can go up to the many thousands of dollars.
“Free sells the frontend, frontend sells the back,” James told me. “Backend’s typically where you make all your money. Frontend either loses money or breaks even.”
Those last seven words haunted me for years…
The Newsletter Engine
In fact, the whole front end haunted me a little.
Firstly, because of the name – if you line up all three product types in the order customers encounter them, the frontend isn’t in the front. It was hard to develop a visual model that used these names and explained them intuitively.
But secondly, because of what James said about breaking even. Let’s face it, if you’re a solo operator, you don’t want to break even. You want to make money. Indeed, we were making millions on Trends at the time, which was a frontend product of sorts.
So what gives?
Recently, I set out to get to the bottom of all this, and came away with a new insight that’s adding a lot of important texture to how I think about monetizing newsletters overall.
Let’s get into it…
The Key Insight:
It turns out that the terms “frontend” and “backend” come to us from the world of direct mail marketing.
There, the “frontend” was generally defined as the first thing customers bought from you, and the “backend” was comprised of everything else they purchased over their lifetime as your customer.
Here’s the key…
The whole purpose of a frontend product was to sell something – anything – to a new reader because once they’d bought one thing from you, they were much more likely to buy future products too, even if those future products were much more expensive.
“It can cost a marketer as much as 15 times more to find a new customer as it does to sell an additional item to an existing customer,” direct marketer Craig Simpson says.
Thus, the reason people were willing to break even or even lose money on the frontend was that conversion rates and profit margins were much much higher on the backend afterward.
Think About It This Way…
If you have a list of 10k free subscribers and you try to sell them anything, you can reasonably estimate ~1% to ~3% of them will buy.
So if you have a $500 course, for example, and you market it to that list, a 1% conversion would make you about $50,000.
Not bad. But here’s the thing…
If you’d sold those same people a front-end product first, you’d still expect at least ~1% (or 100 people) to buy that. Then, those 100 people would have a much higher conversion rate when it came time to sell the $500 backend.
I haven’t seen conclusive data on this yet, but I’ve read that 20% conversion from frontend to backend isn’t crazy. We’ll use 10% here.
So that small list of 100 people who previously bought from you drove 10% of the revenue of a list 100x the size. And we’re using some of the most conservative numbers I’ve seen here –
Relatively small list
Low conversion rates
Low-price backend offer.
You can imagine how all this stacks up if you can grow even one of those three.
The kicker is, if you do it right, the extra $5k should be almost all gravy, since as James said, the frontend is designed to cost you either nothing, or very little.
How This Changed My Thinking…
Three things
First, I finally get what James meant. If conversion rates really are 10-20x higher on people who’ve bought from you before, it makes sense to break even on the frontend in order to boost conversion on the backend.
Second, I used to think of the three product types – free, frontend, backend – as interoperable. You can pick which ones you want to build. But this makes them more interdependent. It’s still possible to get by without one or more, but you’re likely leaving money on the table.
Finally, it cements another piece of advice I got recently from Ryan Carr, co-host of the Newsletter Operator podcast.
We worked together atThe Hustle, where he ran growth on our frontend product Trends, and a couple weeks ago, I asked him when he thought people should launch frontend products.
“I can’t think of a downside to producing a frontend offer to start driving traffic to immediately,” he said.
At first I was skeptical because paid products take a lot of time, effort, and often money to make. Without a big free audience, there’s not much chance you see a return on that.
But I get it now. The frontend’s job is to give you a highly motivated marketing list to sell more expensive products to in the future. So he’s exactly right – the earlier you start building it, the better.
A few other things still swirling through my head on this…
It’ll take me time to fully incorporate this into the way I think about newsletter monetization, but here are a few things I think are true in light of this…
1 . Your Frontend Should Be Fulfilled Automatically
If you’re a solo operator, you can’t spend a lot of time each week on something that only breaks even (unless you have another job, or deep cash reserves, and a plan for a killer backend). So start thinking about product types that can be fulfilled automatically.
Rather than paid newsletters, maybe think email courses, ebooks, guides, etc.
In a recent interview, Ryan Carr, co-host of the Newsletter Operator podcast, suggested was going back through your old content to compile a guide you can sell as a welcome offer to new subscribers for $15-$25. “That provides value to folks so they don’t have to scroll back through all of your old newsletters,” he said.
If you’ve got a paid newsletter already, and it’s struggling to reach profitability, I think there are a couple of options:
Add a lower-price frontend product (like Ryan’s option above) so that you build a bigger pool of pre-qualified purchasers to market your paid newsletter to. Higher conversion rates might make a $100/yr newsletter profitable if it isn’t already. Or…
Price the paid subscription higher (like $500 and up), effectively making it a backend product, and add a new frontend product that can be fulfilled automatically.
Obviously larger organizations can run paid newsletters that break even because they’re not limited to the mental bandwidth of a single person.
2 . You Should Ideally Own Frontend Data
Right now, on my site, I have one paid product. It’s a book I wrote. It’s fulfilled completely through Amazon, which is nice because it truly functions as passive income.
BUT I now realize that carries a price for me, because I don’t own any of the sales data. Anyone who buys the book is Amazon’s customer, not mine.
Theoretically, some of them are on my email list. So if I were to launch a backend product, they might see it.
But I can’t segment them out, or factor their purchase into overall estimates of LTV.
That may not matter for me. I’m not sure I ever want this to be more than a high-six to low-seven figure business, and you can probably do that without a high level of granularity on reader behavior.
But it’s interesting. I get ~$1-$4 in royalties for each book sold. And I think the value of that data is actually higher than that in the long run. So part of me is thinking through other potential fulfillment options that’d bring those insights in-house.
3 . This Adds Nuance To Pricing
I used to say that frontend products are typically priced $50-$100. And that’s true – if you look across the web, a loooot of companies price their frontend there. It works as an easy place to start.
But if the goal is to maximize conversions on the frontend, and you’re willing to break even or potentially lose money, the real math on how to price it would be more similar to how you set your Target CPA on ads.
Here’s something that no one’s going to tell you when you first get started writing or creating things on the internet…
Someday, a new generation of creators will come up behind you, and they’re going to be better than you in a lot of ways.
Sometimes, their work will be better than yours. Other times, it will be worse, but they’ll be better at getting attention, and so eclipse you that way. A few will be both. Others will be better at tapping into the new thing people care about – the thing you think is pointless.
The list goes on…
When this happens – and it will happen to you – you have two choices about how to go forward: You can be small, and defensive; guard the secrets of your trade, and try to deny newcomers the admiration they’re earning with their work. Or you can go the opposite way, and decide that you’ll always do your best to help them succeed.
As you can probably guess, the first path offers nothing for you in the long run, except maybe a little comfort for your ego as you slowly slide into irrelevance. It’s the second path we want.
The second path is tougher, because it forces you to grow as a creative person. It forces you to look at your work, and the work being done around you, and to ask (possibly for the first time in years) what you actually bring to the table that’s unique these days.
It forces you to acknowledge that other people can do some of the things that made you special years ago. It forces you to confront and maybe even kill off parts of your ego.
But if you can do it, you’ll be much better off for it. Because above all, this approach forces you to abandon any kind of scarcity mindset, and when you do that, your work gets better, and you, your peers, and your readers all benefit.
Two people have really helped form my thinking on this.
The first is Tim Ferriss. I’ve been a fan of his for almost two decades, since the publication of his first book, The 4-Hour Workweek. His work inspired entire generations of other writers to talk about solopreneurship, remote work, lifestyle design (a term he coined), and more. And yet, he’s stayed relevant through it all.
I think there are two key factors.
First, he doesn’t hold back information. A lot of writers are scared that if they share everything they know, their audience won’t need them anymore. So consciously or not, they hold back or try to drip ideas out slowly in order to hold onto attention.
But what this really is is a fear that if you say the one big truth you know, you won’t have anything else to say.
I’ve done this. It’s a mistake. It keeps you from writing at the edge of your ability, and what you don’t realize is that by holding back, you’re just being less helpful to readers, which opens the door for someone else who’s willing to tell-all to come in and scoop them up.
Tim tries to write the definitive book on each topic. He doesn’t hold back. As a result, people continue to follow him because they know that he’ll teach them everything he learns along the way.
Your readers are always running into new problems – new issues every damn day. If they think of you as someone who always teaches the maximum they can, they’ll continue to look to you for help with each new issue they face.
That brings me to the other aspect of Tim Ferriss’ long-term relevance, which is his focus. He doesn’t chase trends. Instead, he’s focused on solving the problems he’s encountering in his own life. Then he writes about that, trusting that some segment of his audience will benefit.
So those two things – teaching everything you can, and focusing on the things you’re facing in your own life, rather than chasing trends – those are two good ways to stay relevant for a long time, even as other great writers come onto the scene.
I think they speak mostly to the craft itself; to keeping your work relevant to the audience.
The other person who’s really formed my thinking on this is Joe Rogan, because of how he treats other creators.
Whether it’s podcasting or comedy (both areas in which he’s a dominant player) he’s not just accepting of others coming into the craft, but he actively tries to promote them and make them as successful as possible.
He’s typically pretty subtle about this publicly, but finally shared his thoughts in a recent conversation with Cameron Hanes and Steven Rinella (starts at 2:15:04)
“I don’t think of comics ever as competitors,” he said. “I try the best I can to get them more famous. I want them to be huge.”
What a great mindset.
I wanted that for my career, and frankly, for my day-to-day life. To be free from that useless anxiety over competition, and instead start from this place of abundance. So I chose that, and cultivate it regularly.
These two guys helped.
I also found it helpful just observing my interaction with their work as a reader or listener. In almost two decades, no one has replaced Ferriss in my mind, even though I’ve read and admire many other writers who’ve come up in his wake. No one’s replaced Rogan.
You’re not competing for mind-space in the way that you think you might be.
The only thing that makes you irrelevant are the bad decisions that come from fearing irrelevance. So put that out of your mind, and get back to work.
Geoff Sharpe is the co-founder of Lookout Media up in Canada. They have a string of three local newsletters, spread between Ottawa and Vancouver, and have grown to over 65k subscribers and six-figures in revenue.
Last week, he jumped on Zoom with me to share a bunch of what they’ve learned, including:
The Importance of Hard Editorial Decisions
Keys to Growth
Keys to Selling Memberships
Keys to Selling Ads
He gave me permission to write it all up, so that’s what we’ll look at today.
Even if you’re not running a local newsletter, a lot of this will still be useful. And if you are, I highly recommend connecting with Geoff – he’ knows a ton about this and is really generous with his insights.
1. The Importance of Hard Editorial Decisions
If you’re reading this, you probably already know the fundamental rule of newsletters is, “quality first.” You can have all the growth hacks in the world, but if the stories suck, you’re just not going to get any organic traction.
That’s especially true if you’re heading into markets that already have other players on the field.
Ottawa and Vancouver both have hundreds of thousands of residents. There are plenty of existing news sources for them.
So one of the most important decisions Geoff and his co-founder Robert Hiltz made early on was how they’d be different.
Specifically, they focused on what they weren’t going to do.
“You’re never gonna beat a local news company at getting local news,” he told me. “But where you can beat them is having an interesting analysis and point of view.”
In other words, personality.
The Lookout team didn’t think Vancouver needed more listicles about “Five Best Pasta Places In Town,” so they decided to focus on deeper coverage of local news, events, and restaurants, with the goal of becoming a trusted resource.
Under-the-radar restaurants, and data-backed regional news
If you’re going through this, give yourself time. Geoff says it took them 3-6 months of testing (publishing 3x per week) to really find their editorial groove. But now, three years in, the brand carries weight, and gets recognized on its own. That gives them the flexibility to bring on new writers or potentially even expand to new locations because they took the time to build the foundation.
2. Keys to Growth
Like most of the local newsletter operators I’ve talked to so far, Geoff and the Lookout team rely primarily on Facebook and Instagram ads to grow their audiences.
“You want to know my targeting for these ads?” he said, laughing. “The city.”
He keeps the audience targeting super simple, letting Meta handle most of the optimization on its own, and as a result, he’s seeing ~$0.60-$0.70 CPAs, with high open and click rates.
They’ve experimented with a lot of formats, but a few things he likes to test in ads include:
Images of recognizable local landmarks
Different “contrast messages” that tap into local identity or even tribalism (e.g. “If you live in XYZ, you won’t want to read this.”)
3. Keys to Selling Memberships
This was fascinating…
Like other local newsletter founders I’ve talked to recently, Geoff told me that it’s tough to scale local ad sales. Budgets are relatively small, and you spend a lot of time educating old-school business owners on benefits of a newsletter audience.
But Lookout compensates for that by leaning hard on paid subscriptions and he estimates ~75% of their revenue (!) is from paying subscribers right now.
Increased Audience LTV: Readers become worth more, which changes how much you can spend to advertise to them.
Diversified Revenue: Ad markets are fickle, and change with the wind. Having subscription revenue protects you from sudden shocks
Recurring Revenue: Maybe the biggest benefit of paid subs – many of them keep paying year after year, funding your growth plans
Lookout offers memberships in either monthly or annual format. First year goes for ~$75, then the price increases to ~$120, which means they could lose ~30% of readers from year one to two and still earn more.
He told me that annual is better to focus on, since they find churn is ~2x higher on monthly subs, and for the Lookout group, he estimates ~85% of paying members are on annual plans.
It’s wild to hear that this is possible with local newsletters, but there you go!
Interestingly, I recently asked Farhan Mohamed of Overstory Media, how he would recommend I think about revenue if I wanted to build a $1m local newsletter in Austin, and he said something similar; Think about how to make ads 25% of the pie, and fill the rest with things like events, paid subscriptions, etc.
This 25% ad ratio may be a broader theme in the industry.
So how does Lookout sell these paid memberships? Well, there are two components:
Get Clear On The Value: Insiders get access to content free readers can’t see, including their updates from city hall meetings, and long-form pieces on restaurant gems.
“Support Local Media”: They lean into this narrative, and it works. Interestingly, I’ve heard this from other local media founders too – readers seem happy to pay to support quality local writers.
The highest-leverage time he’s found to sell paid memberships is 2-3 months in, after people have experienced some of the value and gained an affinity for the newsletter.
So, he focuses on quarterly sales drives. They make a limited number of memberships available at a discount, and lean hard on the narrative of why people should support now.
4. Keys to Selling Ads
Okay, so selling ads is hard. But you should still try it.
Geoff’s biggest tip was to do what you can to pre-qualify advertisers by making sure they have the budget before you get on a call with them.
They use Tally as their contact form. We used them at Hampton too because they have this cool feature where they can collect data from forms poeple don’t finish filling out. Can be super useful for you.
He reviews submissions and emails promising leads to set up a call.
Pro Tip from Geoff: Set up your sales flow so that anyone who doesn’t pre-qualify for a live call can still be funneled to an automated checkout where they can buy inexpensive ads in your newsletter without any face-to-face interaction.
Another major insight – keep it simple.
I’ve heard this from several other local newsletter founders too – a lot of local advertisers just aren’t as sophisticated as venture-backed tech startups or large global brands. They’re not used to seeing performance data, or measuring direct ROI.
That’s not a dig on them. It just means that when you’re selling you need to position the value differently than you might in other circumstances.
A lot of these business owners are used to buying ads in local newspapers, so Geoff often guides the conversation toward the problems those publishers are having right now.
“When was the last time you saw and clicked on a banner ad on a website?” he often asks.
When you frame it that way, people intuitively understand the issue, and it opens the door to talk about other types of advertising options.
For More From Geoff…
Check him out on Twitter, and if you’re in Ottawa or Vancouver, check out their newsletters here:
It’s been an interesting week for journalism after Tucker Carlson published his live interview with Putin.
Don’t worry – we’re not gonna talk about politics today.
But it occurred to me that Carlson provided a timely counter-point to my article last week, and I thought it was worth sharing.
The main focus of last week’s piece was that the world is filled with fascinating and insightful people who routinely get overlooked by journalists when researching a story. If you know how to spot them, and reach them, you can write stuff no one else can.
Carlson, I realized, deals more with “untouchable,” guests. People who are widely disliked or even condemned, and rarely given a chance to speak at-length, unfiltered.
It’s very similar to what drove Rogan to the top of the podcast charts during the pandemic.
Anyways, all this got me curious about Tucker’s business, so I looked into it and found a couple things I think anyone can learn from him. Today, we’ll look at:
Some Background
How He Makes Money
How He’s Growing
What Surprised Me
The analysis is going to be entirely A-political, and we’re not going to look at the Putin interview itself. But at the bottom I’ve got some final thoughts for people specifically interested in understanding that better.
1. Background:
If you don’t know him yet, Tucker Swanson McNear Carlson is an American political commentator, famous for his conservative views and influence.
He’s been in media since 1991, writing for many outlets – including Arkansas Democrat Gazette (his first writing gig out of college), New York magazine, Reader’s Digest, Esquire, Slate, The NYT Magazine, The Wall Street Journal, and others.
He’s also published three books, and was co-founder of a news site called The Daily Caller, which he launched in 2010 with his former college roommate, Neil Patel (not that Neil Patel).
He’s had a long career in TV, including stints at CNN, PBS, MSNBC, and FOX, where his show, Tucker Carlson Tonight, grew to a peak of 5.3m viewers per night in late 2020 – the highest of any news show ever up to that point.
In spring of 2023, he was suddenly dismissed by FOX (there have been several theories put forward as to why, though as far as I can tell, FOX has never confirmed any).
Since then, Carlson has been building the Tucker Carlson Network, a streaming platform owned by his newest company, Last Country, Inc. which he founded with the same co-founder from his other company, Neil Patel.
Articles of Incorporation for Last Country, Inc.
First Lesson – Long Term Relationships: I think the big takeaway here is how important a handful of relationships will be all the way through your career in media. Tucker and Neil went to college together in the ‘80s. They launched a business twenty years after that, ran it together for a decade, and then partnered on Last Country too.
Who are the people in your life that you’ll collaborate with over and over for years? That’s a question worth thinking about.
2. How He Makes Money
Carlson and Patel raised $15m for Last Country, Inc. from a venture fund called 1789 Capital.
Just to hammer home the importance of long-term relationships in this game, 1789 is spearheaded by a man named Omeed Malik, who also invested in their last company, The Daily Caller.
Right now, the company monetizes in a few main ways:
Ads (direct partnerships + ad share on Twitter & Youtube)
Paid Memberships: $72/yr or $9/mo.
Speaking & appearance fees
He’s likely also still getting proceeds from his 3 books.
Ads: They sold their first ad deal in the fall of ‘23. It was reportedly valued at $1m+, and went to a company called Public Square.
Get this… Public Square is also influenced by Malik, the investor who backed both of Carlson’s companies. You see, Malik formed a blank check company called Colombier Acquisition, which eventually merged with Public Square to form PSQ Holdings.
Seriously, it’s tough to over-state how critical these long-term relationships are.
This was also interesting to me coming from more of a boot-strapped media background. To see the way some of these high-level players move millions of dollars around behind the scenes – just shows there are levels to the game most people never realize.
Paid Memberships: Their main product is called Team Tucker. It gets you access to behind-the-wall videos. This is priced in the typical “frontend” range of $50-$100 per year (low enough to be an impulse-buy, designed to reach mass audience).
Speaking & Appearance Fees: I’ve had a hard time digging up any solid info on how much Tucker gets paid to speak, but the numbers I’ve seen range from 6- to 7-figures which seems in-line with someone with his audience size.
What’s interesting is that he’s given a name to these speaking events – the Sworn Enemy Tour.
That’s different from other speakers I’ve seen. A lot of other speakers simply offer to speak, and leave it at that. But by rounding up all the events and making them part of a “tour” – a cohesive project – it feels like he creates more demand.
You’re not just paying Tucker to appear. You’re part of the tour. Part of his mission.
I don’t know, it’s interesting. Filing this away mentally for the future when I want to do more speaking.
3. How He’s Growing
At the tactical level, Tucker uses a handful of levers to drive audiences toward his new platform.
He posts organically on social, where he has large audiences on X, Facebook, IG, Youtube, and Rumbler. He also relies on earned media from other press, and is even testing Facebook ads.
But let’s talk about the real over-arching strategy here: He’s polarizing.
He doesn’t rely on a specific growth hack or tactic so much as he taps into emotion – controversy – and uses that to spread. People who love him talk about him all the time. And people who hate him talk about him all the time.
He knows exactly how to pull that lever. Just take a look at the lineup of recent interviews on his site…
This is something I’ve observed with a lot of successful media founders. They think in terms of emotion, not topic. Certain emotions cause stories to spread. That’s the wave they ride.
It reminds me of something I learned early in my time at The Hustle. I was interviewing Sam about a story they’d done on scamming the Amazon best-seller list, and he told me that when they published, he knew the haters would spread the story just as far (if not further than) the people who loved it.
That’s the dirty secret of media.
I don’t think it means that you need to be artificially controversial in order to succeed. But I do think that the more comfortable you are with being disliked by some people, the better you’ll do.
4. What Surprised Me
The thing that shocked me most about Last Country, Inc. is how basic their growth systems seem to be right now. For example…
He’s only got one ad running on Facebook – no variants
There is no – I repeat NO – email capture on his site
That second one is absolutely wild to me.
I’ve thought a lot about this and basically have three theories as to what’s going on here.
The only ad currently running for Tucker Carlson Network on FB
Theory No. 1: Tucker’s spent most of the last 23 years in TV, and maybe email and social media ads just aren’t an obvious growth choice for people coming from that industry. Seems unlikely though, given that they built The Daily Caller which is web-based.
Theory No. 2: He also comes from political media, where it’s much more common to buy email lists. Maybe that’s what they’re doing.
Theory No. 3: Maybe they just don’t think they need it. He’s got big audiences on all his social platforms. Maybe they’re already able to drive the kind of business results they want with that.
I have no idea. Honestly, I’m shocked. But we’ll see what happens over time.
Final Thoughts: The Putin Interview
I’ve listened to a lot of third-party analysis on this interview. Some of it is good. A lot of it’s not.
If the war in Ukraine is particularly important to you (as it is to me), and you’d like to form your own opinion, here’s my best suggestion:
First, watch the interview itself in-full. It’s so crucial to know what was actually said before listening to any analysis from other parties.
Then listen to this breakdown by Konstantin Kisin and Francis Foster. It’s the most balanced I’ve found yet. As an added benefit, Kisin was born in the Soviet Union, and has been translating Putin’s speeches for English-speaking audiences throughout the war, so he has context many English commentator’s lack.
Finally, watch this talk about the Russian mindset. It was recommended by Kisin in the video above, and I think it ads crucial context to Putin’s words in the interview, and the broader war. I wish I’d seen this two years ago.
My own bias is toward Ukraine. I’ve tried to keep that out of this piece, but my view is colored by it. Still, I found this to be an important conversation, and I think critical western audiences will benefit from analyzing it.
