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 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.
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.
Last week, I wrote a piece about five of the key hires who took Morning Brew to $40 million in revenue.
I mentioned that I had a process for finding such people, and was surprised by how many of you were interested in hearing more about that.
So this week, I’m going to show you that process, but I want to ground it in something a little more important – namely, why look for these people in the first place?
Well, here’s why…
###
In any business, including the creative ones, there are really only three types of advantages you can have over your competitors:
Resources: You have money to burn, and they don’t
Behavioral: You naturally do something that they don’t
Information: You know something they don’t
When a writer buys $200,000 worth of their own book in order to guarantee it lands on the bestseller list (yes, this happens), that’s a resource advantage. They have enough money to manipulate the system, giving them an edge, even against people who may be better writers.
If someone writes compulsively, and just can’t help themselves, that’s a behavioral advantage. They have an edge over the person who has to force themselves to sit down and write.
Personally, I prefer an information advantage because I think it’s the only one you can choose to cultivate, and is most resilient to AI.
And when it comes to information, the biggest moat that you can have is access to people. Not famous people. But rather, the people behind the scenes who have just as much insight and far less attention.
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Stephen Hanselman, Heather Jackson, Donna Passannante, Tara Gilbride, Ilena George, Lindsay Mecca, Kate Perkins Youngman, Laura Hurlbut.
Do you recognize any of those names?
Probably not, but they’re some of the first people that Tim Ferriss thanked in the acknowledgements section of The Four Hour Workweek, and they belong to his agent, editor, marketing director, and publicity director, respectively, along with the four interns who helped him get the project over the finish line.
Isn’t that interesting? The stories they could tell…
That book spent more than four consecutive years on the New York Times best-seller list, and fans like me default to giving Tim all the credit for that. But he himself considers these people absolutely crucial to the success of the project and we don’t even know their names.
And this is the big point – there’s an asymmetry between the people who have interesting experience and insight on any particular topic, and the people who get the attention.
It holds true in every arena. Every company. Every creative project. Attention flows like water towards a few people at the front. But for every CEO, or lead actor, or author, there are lots of people slightly behind the scenes who have just as much fascinating insight. Maybe more.
More?
Yes, maybe. Check this out…
A quick Google of Stephen’s name reveals that he didn’t just work with Tim on each of his five books. He also worked with other incredibly popular authors like travel writer Rolf Potts, investor Kamal Ravikant, and stoic Ryan Holiday.
Indeed, he’s actually a co-author of at least two of Holiday’s books.
So if everyone wants to write a story about how Tim Ferriss or Ryan Holiday became best-sellers, the path taken by most of your competitors will be to either…
Do a lot of Googling, and rehash other pieces or…
Try to contact the authors for (yet another) interview
An option that’d set you apart would be to reach out to people like Stephen.
Tim and Ryan are practically impossible to contact because of the volume of inbound they get. Stephen’s Gmail address is listed right on his Publisher’s Marketplace profile.
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I think my old company, The Hustle provides an interesting example of how this works in practice.
Our main competitor was Morning Brew, and if you subscribe to both The Hustle and Brew, and a few other similar newsletters, what you’ll find is that maybe 40-60% of their daily coverage overlaps.
They report on the same stories, share the same links.
Why? Because everyone’s pulling from the same few information sources.
Running a multi-million dollar daily newsletter is all about efficiencies. Over time, each writer finds their favorite sources – a few places they’re guaranteed to find the stories readers want – and there are only a handful of those.
The Sunday edition of The Hustle was refined by Zachary Crocket, and it sprang from his desire to do more in-depth, long-form coverage of business stories that were further off the beaten path. Things like…
You can’t just Google these kinds of things. That’s why they’re so interesting.
Zack spent his time combing through old newspapers, absorbing the comments in very niche Facebook groups, or rifling through long-forgotten boxes in the dark corners of museum archives.
Almost as a rule, he tried to avoid talking to big, well-known names. Instead preferring the people who were deep in the trenches, had lots of experience, and almost zero attention.
He wrote what no one else could because he looked where no one else would.
And he (read, “we”) were rewarded for it. The pieces were insanely popular. To this day, it’s common to surf Hacker News and see one of the old Sunday Stories from years ago trending on the front page again.
When you write what no one else can, people want to share.
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I know I promised you my own personal method for finding these kinds of interesting employees in a company, so here it is…
I like LinkedIn.
When I’m deconstructing a company, I start by reading a few interviews with the founders to plot the growth over time, along with any other major milestones.
I chart it so I can see any major turning points. For example…
Then, I search LinkedIn for everyone who’s worked at a place, or was hired around major turning points in a company, and manually plot their…
Name
Title
Department (Editorial, Sales, Operations, etc.)
Start/End Dates
…in a spreadsheet.
There’s probably a way to do this automatically with robots or VAs or something, but I do it manually because I find it gives me a much better feel for each person’s actual relationship with a company.
For example, on LinkedIn, someone may say they were CMO of a company for just three months, and if you take that data at face value, you may think something very bad must have happened for a company to hire and lose such an important role in so short a time.
But when you look closer, you see that this person was a sophomore in college at the time, that the company was just a month old, and that actually, it wasn’t so much an executive hire as it was kids trying to get something off the ground.
That sort of thing happens a lot when you study startups, and that’s why I do it manually.
At any rate, if you do this, what you’re left with is a map that shows how a company grew over time – where their hiring priorities were, and by extension, the major challenges or opportunities they were facing at any given point, as well as the people who played pivotal roles in their success.
It’s not perfect. Some people don’t keep their LinkedIn up to date. But it’s directionally accurate, and enough to give you the kind of look into a company you won’t typically find on TechCrunch.
Once you have that, there are two things you can do:
Sleuthing: I plug names of lesser-known key employees into Google and Spotify to see if they’ve talked about their work publicly at all – often, they have.
Consulting: A lot of people are happy to give you an hour of their time after they leave a company, and for $100 or so, you can learn things the original employer paid thousands to understand.
You don’t need many. In fact, most the time, all it takes is one name, and from there, you can find your way to the rest.
That’s the beauty of focusing on people – they have such rich context. A ten-minute chat can save you hours of research.
And so I’ll leave you with one more little tip I got from Zach when we worked together – something small that’s had a big impact on my work.
When finishing an interview, one of the last questions he always asked was, “Who else do you think I should talk to about this?”
It’s small. But you wouldn’t believe what comes from that.
In the beginning, every new subscriber is exciting. They trickle in day by day, and every single one is a signal that you’re onto something with your newsletter. You were right! People want this! You’re unstoppable!
Eventually, you think, there will be a day when you will count new signups in the tens, or hundreds, or even perhaps thousands per day.
But right now, each one is a big deal.
Then comes the morning where you wake up and the list hasn’t grown at all.
Wait… has it? Did I have 43 or 44 yesterday? Did it shrink?
The analytics show it definitely hasn’t shrunk. But what the hell? What happened to my little rocket ship? Do people hate this idea? Am I a failure? Was my second grade bully right about me? And most of all…
Why bother with this?
Here’s how to keep going in the face of all this nonsense…
Think about the list, however small, as a group of people in a room. Whether it’s 1,000, or 100, or 10 – however small it is, remember those are real people sitting in a room, waiting for whatever it is you’re writing.
Then treat the work the same way you would if you had to go stand in front of those people, and share it with them face to face.
Make something you’d be proud to show to ten people in a room, and you’ll end up with something worthy of ten-thousand. Then, when you get to ten-thousand, and that no longer feels like an accomplishment, put them all in a room and imagine yourself on-stage.
You can keep going with the exercise every day for as long as you work. Because the reality is that it always comes back to the people.
Recently, for the first time, I noticed daily stories making their way through the newsletter community on Twitter.
Similar to the way national news has a handful of daily stories that all the channels cover, the newsletter industry is now big enough and has enough people talking about it that my feed was filling up with different takes on the same topic every day.
One day, it was, “Beehiiv or Sparkloop?” The next, “Are we in a newsletter bubble?” Or perhaps, “Can you really call creators business owners?” Etc., etc., etc…
It reminded me of this quote from Hemingway:
“Writers should work alone. They should see each other only after their work is done, and not too often then. Otherwise they become like writers in New York. All angleworms in a bottle, trying to derive knowledge and nourishment from their own contact and from the bottle…”
That book is one of my favorites, by the way. I’m convinced you can learn everything worth knowing about writing by just studying that one your entire career.
Anyways, I realized I was spending too much time in the bottle, and it was affecting what I thought I should write about. It was also making me feel less relevant if I didn’t comment on the topic of the day.
Of course, any time spent focusing on today’s “thing” is time you don’t get to spend making something that lasts a long, long time. And that’s a problem.
So I unfollowed everyone, on Twitter at least.
I do still read their long-form stuff, either via their blogs or newsletters, and this has two important benefits over social media:
First, it’s long form. They’re usually exploring an idea in much more detail, and you’re absorbing more deeply.
But second, and perhaps more importantly, you’re taking each person on their own, rather than as a chorus. And the difference between those two things is the difference between signal and noise.
I was on the phone with another local newsletter founder the other day. He’s doing 7-figures across a handful of publications, and he asked me what I thought the gap was that my Austin newsletter was filling.
It’s a great question. And to be honest, I hadn’t thought about it much. I guess the way I’m trying to go about this newsletter is I’m building the thing I think one or two of my friends would like to have.
But the longer I spend in business, the less crucial I think an actual gap in the market is. Most of the wealthiest people I know are plumbers, and closet installers, and house painters and the like. They’re not tapping into new markets, but just serving a big existing one with lots of healthy competition.
But I do think a lot about advantages, and what, if anything, allows you to differentiate yourself and stay in business, even if others are serving the same customers you do. And I’ve always liked the framework put forward by Tim Ferriss that says there are essentially three possible advantages you can have:
Informational
Behavioral
Resources
I don’t have millions to make the newsletter work, so I can’t out-spend or out-wait competitors.
As for behavior, I’m a default-introvert who’s quite happy (too happy, really) to lounge around at home rather than going out. Oh sure, I can be social. But there’s no compulsion I have that would make me better at writing a local newsletter than someone else.
The thing I plan to lean on is an informational advantage, and this is may be interesting to you because it’s (I think) the one thing you can choose to develop.
I’ve heard it said that a well-curated Twitter feed can be more valuable than an MBA, and I agree.
So the first few weeks of this process have been largely focused on building the kind of information flow that will allow me to curate something fascinating for readers.
The process is simple, really. Just time-intensive, and you can’t rush it.
I have an RSS feed, Twitter, and a Google doc.
The RSS feed is subscribed to a few great news sources around town, and on Twitter, I keep a list of individual people who say and do interesting things here too.
Each morning, I spend a couple hours reviewing both closely. Anything that seems like a good fit for the newsletter gets dropped in the Google doc for use later.
That’s where most of the content comes from, but the secret is that as I’m reading, I take the time to continue updating both the RSS Feed and the Twitter list.
So if I read a story about an interesting local founder, I may add them to my Twitter list to stay up to date on ideas they share in the future. If they have a personal blog, I may add that to the RSS feed too. Depending on the situation, I may also reach out, introduce myself.
With each new addition to the info stream, I get a better and better sense of what’s going on around town, and what little-known things readers might like to hear about.
It’s really very simple, but it takes time and you can’t force it, and that’s why most people never do it.
With time, you can get to a point where you’re seeing things long before most other people, or you have access to information others can’t get. Then, your audience is locked in because everyone wants access to information that’s hard to find.
This pipeline of information is one of the most important assets you can have as a writer, and it’s one you can build virtually for free.
Today, we’re lookin’ at Peter Zeihan to see what he can teach us about being a high-priced creator/consultant.
If you don’t know Zeihan, he’s a geopolitical analyst who’s gotten famous over the last few years for his opinions on China, the US, and the future of globalization (namely, that there isn’t going to be one).
But my fascination with him has less to do with his public opinions, and more to do with how he spends his time.
He seems like the paragon of a paid thinker…
Author of several books and a near-daily newsletter
Lives in the mountains of Colorado, close (but not too close) to Denver
Long hikes every day to think and record Youtube thoughts
Travels often to give paid speeches and seminars to big companies
Likely doing 7-figures in annual revenue without much of a team
Doing well enough to donate 100% of book proceeds to charity
Funny
Basically, when I grow up, I wanna be like Peter.
So this week, I spent a few hours digging into his business to uncover any key learnings. We’re going to look at three:
Business Model
Ideas > Optimization
Chosen Relevance
1. Peter Zeihan’s Business Model
Before we dive in, remember that all media companies essentially make money in one of three ways: Free products (which are monetized via ads and affiliate deals), front-end products, and back-end products.
I’ve been dissecting all sorts of creator-led media brands in public and private for years now, and have yet to find one that doesn’t fit this model. Peter is no exception (although he is using some interesting products we don’t see often in the typical newsletter space). Let’s dive in…
Free Products
The core of Peter’s media footprint includes two key properties: his newsletter, and his Youtube channel. Both are free, but that doesn’t mean they don’t earn money:
His Youtube channel is monetized, and averages ~1.5m+ views per week. At an estimated $5 CPM, that’d be ~$7.5k per week from Youtube alone
Both the newsletter and Youtube include plenty of calls to action selling his other products (below)
C2A on his Youtube videosC2A in the Newsletter to buy the books
One smart thing: In videos, lectures, podcast interviews, and writing, he continually emphasizes the fact that both his newsletter and Youtube videos are, and will-always-remain, free. That’s a good way to help growth.
Traditionally, front-end products are paid products that run roughly $50-$100 (cheap enough to be impulse buys).
Technically, the only thing Zeihan offers in that regard are his books.
However, he also does something I haven’t seen a solo-creator do before: He sells high-ticket webinar recordings. He’s got more than half a dozen webinars priced $650-$750/ea., and covering topics from inflation to the Ukraine War’s impact on energy, food, and materials industries.
I’m going to lump these in as front-end products for two reasons:
His remaining products are likely much, much more expensive, so relatively speaking, these are still his “low barrier to entry” offerings
The corporate clients these are designed to appeal to are less price sensitive than typical consumers (more on this soon). So again, in relative terms, these are “low priced”.
Back-End
Finally, on top of these, Peter also does:
Speaking: He’s represented by several speaker bureaus, and in this interview with Joe Rogan said that he did 179 seminars last year. Hard to know if those are all in-person or a mix or live + online, but either way, it’s a lot.
Executive Briefs: I’m not quite sure what these are, but I’d imagine they’re high-ticket, highly specialized research projects undertaken for execs at a specific company. Maybe something like this PDF he wrote back in his days in private intelligence.
Consulting: Always a mystery.
2. Ideas > Optimization
I don’t know much for certain about how much money Peter makes each year. But I do know…
From this podcast that he’s looking forward to retiring soon.
From this newsletter (posted Friday) that he’s doing well enough to donate 100% book proceeds to charity.
So he’s doing well. And yet, anyone who’s spent time focused on growing an audience would look at the website and see at once that it’s kind of stitched together – not really optimized for conversion.
There are plenty of email capture forms. But they don’t really flow, the pages are just a little chaotic, and there are clear gaps in the funnel.
For example, there’s no nav button for the webinars. The only way to find them is by clicking through random newsletter, or Youtube video archives. Maybe they’re not a priority. Or maybe it was just overlooked.
Chaos (but pushing the newsletter hard, which is good)
And yet, my conservative estimates place his annual revenue in the seven-figure zone when you factor in speaking and consulting fees.
So what’s the point?
The point is that even if you don’t optimize every last detail of your site, you can generate more than enough money by getting the big things right:
Speaking of monetization, that brings us to the next interesting lesson I feel Peter’s work has to offer us all as professionally curious people…
3. Chosen Relevance
I’ve mentioned a few times now that a lot of his time is spent speaking to, consulting with, and writing for executives. Specifically, executives in the agricultural, industrial, and energy sectors.
a.k.a. People with deep pockets.
These are big industries where a lot is at stake. And there’s an important lesson there: Zeihan has purposefully found a way to make his passion (geopolitics) relevant to big companies who can pay him lots of money to hear how his research can make/save them even more money.
Let that sink in for a second.
He purposefully figured out the link between what he was interested in, and what big companies are willing to pay to learn, then used that as the foundation for a (likely) multi-million dollar publishing and consulting empire.
I don’t know about you, but this has me thinking questions like…
What big industries would care a lot about topics I like researching?
What are the specific angles they would care about?
How much is on the line for them? What’s it worth?
What would they need or want from me? (in terms of webinar topics, executive briefs, etc.)
To take things one step further, he’s even found ways to have a positive impact on some of these major industries by showing them where there’s incentive for them to go greener, or more local.
Someone recently asked me for the playbook we use to write our community newsletter over at Hampton. He was hoping for a one-pager he could give his team, so they could write something similar for their industry.
That was a big compliment.
It was also a little daunting because the last thing I wrote about content strategy was, like… Fifty pages. After cutting.
So I’m going to try and write something shorter and more actionable here. We’ll focus only on the real stuff I do each week to produce our email, and we’ll cover:
Developing A Template
The Importance Of Your Drop File
Writing The Bones Each Week
Editing + Style
The Final Step
None of this is Hampton-specific. It should all transfer.
1. Developing A Template
When I talk about a newsletter template, I’m talking about the overall structure for the email – the major sections, and what goes in each.
Having a template for your newsletter is important because…
It makes the email easier to write each week
It helps you think about the purpose of each segment you include
Over time, it sets expectations with readers, and helps them skim and find what they’re looking for faster
The easiest way to start is to copy the format of a newsletter you already like, and iterate from there as you see what works and what doesn’t with your audience.
Each week, when I sit down to write, the very first thing I do is duplicate the last week’s email. I remove the old content, and the rest of my job is just filling in the structure with new content.
This saves a ton of time and energy. In fact, steps 1-3 are all about saving time and energy so you can spend it on step 4 (styling), where it’s most valuable.
So have a template.
The important thing to know is that your template evolves over time, and will take a while to solidify.
I’d estimate it took us about 2-3 months of weekly emails to settle on a pretty good structure at Hampton. And even then, it’s still evolving (currently in the middle of a visual refresh, though structurally, it’ll remain mostly the same).
Ours currently looks something like this:
Brief Intro
Recap Of Popular Slack Posts
New Members From This Week
Upcoming Events
A Post From The Blog
Every one of these is designed to do something specific (like get people excited about the Slack group, drive event RSVPs, or get eyes on the member interviews we publish on our blog).
And each of those, really boils down to the same single thing – helping members connect with one another.
That’s the essence of a community email. It’s about creating points of connection between your readers.
There are a hundred little tactics (for example, we intentionally include a lot of names in each issue – names, names, names!), but if you just write with the intention of creating connections between your readers, you’ll find your way.
2. The Importance Of Your Drop File
Okay, so you’ve got a template. Now how do you fill it in each week?
Answer: Your drop file.
The drop file is a simple Google or Word doc that you keep handy all week long. As you stumble across things that could be cool for your newsletter, you drop them in the drop file, and forget about them until it’s time to write.
I keep mine right in my bookmarks bar.
The structure of the drop file is simple. It’s a running list. Just bullet-items for each idea you come across, and maybe a few quick thoughts or follow-up links to help you write later.
You can find ideas anywhere. But over time, you’ll narrow the list of sources down to a few that deliver great options every week.
At Hampton, most of our content starts with our Slack channels. We’ve got hundreds of members in there, and our weekly active users have hovered between 85-89% from day one. So every week, there are a bunch of great conversations going on.
When I come across one I want to remember, it gets added to the drop file.
Then, whenever I sit down to write newsletters or do content planning, I open the file to jump-start the process.
3. Writing The Bones Each Week
With your template and an active drop file, the process of writing the newsletter is actually pretty simple.
It’s usually a process of…
Looking at your template – what needs to be filled in?
Looking at your drop file – what fits where in the template?
Match one to the other.
Rinse and repeat to fill in the major sections of the newsletter
On the first pass, I don’t write much. I’m just slotting story ideas in to make sure I like how they all fit.
Sometimes, a story or link might be a good match for more than one section of the newsletter, and it’s not immediately clear where it should go. But a little plugging and playing usually helps sort things out as I see the broader email take shape.
As things start to click, I’ll add more detail to each section, writing segments the way readers will eventually see them.
4. Editing + Style
Ultimately, your voice is the most important part of your style, and that’s different for everyone.
But here are a few editorial best-practices we used at The Hustle, which I’ve carried to Hampton, and which (I feel) make the newsletter easier and more pleasant to read…
Use simple language
Short paragraphs (no more than 2-3 lines in a Google doc)
An image at least every 200-300 words to break up text
Use bullets and bolding to make it skim-able
Axios really pioneered this style in recent years. You can learn more from them in their book, Smart Brevity.
5. The Final Step
Finally, testing. You want to a send test-version of the email to yourself.
When you get out of the editing window, and review in your inbox, you’ll pretty much always catch at least one thing you missed.
At minimum, you should read the newsletter on your phone, and click each link to be sure it’s headed to the right destination.
It can also be a good idea to read it in dark mode if it’s very design-centric. A surprising number of readers leave dark mode on all the time, and it can throw off certain design elements or make certain text hard to read.
