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How to Create Useful Content
For people who hate creating content
How to Create Useful Content

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Why This Episode Exists + Nerdy Stuff Not In The Pod 💡
This week, we talk content. Specifically, how to make it painfully easy to create useful content - particularly for people who don’t think they’re capable of creating compelling content.
We reframe content as a tool - something your customer can grab hold of and use to solve a problem. This ensures the content is evergreen and can turn into an effective customer acquisition lever.
I talk through a broad framework (below), and run through examples to help you create a process that spits off content as a byproduct.
Framework:
Identify your customer's journey (the "river") and the obstacles they face (the "dams").
For each obstacle, uncover the truth about why your customer struggles to overcome it.
Create top-of-funnel content that acknowledges your customer's "hole" (their struggle) and provides a "ladder" (a solution or useful information).
Test insights and acquisition channels with this content.
Develop mid-funnel content (e.g., onboarding email flow) that goes deeper into your customer's struggles and success stories.
Continuously update this content as you learn more about your customers.
Use brand-building content on discovery channels (e.g., LinkedIn, Twitter, TikTok) to test insights and channels.
Focus on cataloging your customers' experiences and stories rather than creating content from scratch.
Record and share customer interactions (e.g., Zoom calls) to provide context and build trust.
Continuously speak with your customers to uncover their struggles and the solutions that have helped them overcome obstacles.
Pod References
Pod Timestamps:
00:30 Intro
02:00 We’ve Got Mice
05:15 The Mouse Man’s Funnel
07:50 Smooth Jazz
08:21 One - Build Your Funnel to Match Customer Emotion
11:45 Good Questions For Your Funnel
12:30 Two - Contrast from the Feature Fold
14:30 Saving your Customers a Decision
15:53 Three - Take Yourself Seriously
19:14 Four - The Things Other People Stink At
22:14 The End
22:50 Recap of the Four Lessons
Transcript - Feel Free to Read it Like a Long-form Article:
Today, we’ll answer two of the questions we get asked the most.
Should I create content to help build awareness and trust as I test out and build my business?
And
If, so, what the heck do I write or record or talk about?
Most things in the startup world are counterintuitive, and content is no exception. The way to create great content is to not create anything. And the use for content early on usually has a whole lot more to do with your product than the content itself.
And, most importantly- by far - nobody wants to hear your voice. They want to hear their voice, in you. If that sounds pretty yoda-y, don’t worry, we’ll sort it all out.
And before we get too far into it, let’s shine a light on the elephant in the room. Lots of founders say they aren’t going to create content because they aren’t good at it. That’s a cop out. We’ve worked with thousands of entrepreneurs and every single one is capable of creating useful content, in the way that we describe useful - meaning, it does its job. You’re included. You can create content that gets you customers.
We aren’t telling you to make tik toks or to write out those weird linkedin posts that are just a summary of a wikipedia article or the other ones that start with some unnecessary personal statement like “when I was younger, I was terrified of clowns.” That stuff is dumb and in no way useful to anyone. We’re talking useful content in the truest sense of the word. Content that will be of use to your customer. That’ll help them solve a problem.
And since I love a good group of three, today we’re going to tackle three things today that support you creating content that’ll help your business gain momentum.
First, figuring out where to start
Second, building a system that makes generating ideas and creating content straightforward
Third, running tests with top of funnel and mid funnel content
By the end, you’ll know what to say and where to say it. And, you’ll know how to predict when someone will order the super spicy hot sauce at Dos Toros.
Actually, let’s start there - in a Dos Toros in the West Village of New York City in 2017. Now if you don’t know Dos Toros, it’s a burrito place that I thought was the best burrito in NYC until I went to El Gallo, which has a far superior burrito, but also seems to be run by a flock of seagulls or something because of the 25 times I’ve ordered from there I don’t think I’ve gotten what I actually ordered even once. It’s to the point where I think it’s a strategy. Like instead of a burrito they’ll give me three tacos because they’re so confident I’ll like them. And they’re right. I’ve also definitely been given other people’s orders a few times and never said anything because all the food is great and I’m confident that whoever got my order will be happy, too.
Side note, we’ve been pitched this idea a few times. Not the mismanage your restaurant idea, but the general “mystery box” idea. I just did a quick search through Tacklebox applications and found 7 since 2016 that are pitching some form of an app that just has one button - “order food” and then the number of people you’re ordering for, and then, some amount of time later, you get… something from somewhere. It sounds pretty damn whispery, and we’ve never worked with someone with this idea.. but… the same idea 7 times seems like a lot, right? Sound off in the comments. We don’t have comments as far as I know, but I’ve heard people say that and it sounds cool. We’re way off the rails. Back to Dos Toros.
I was eating lunch there with a friend of mine who I won’t embarrass but has written a few best selling books. We were talking about something when he got a huge grin on his face and said -
“This guy is going to get the hot habanero sauce on his burrito.”
Dos Toros is a crammed little restaurant and we were maybe 7 feet from the counter, which is similar to a Chipotle, in that you sort of order your burrito assembly line style. A few seconds later, the person working asked the customer which hot sauce he wanted - mild, medium, or hot habanero, and without missing a beat the guy boomed hot habanero.
My friend started laughing and pulled out a flexible notebook the size of a passport he keeps in his back pocket with one of those space pens attached to it by a piece of string and started scribbling. He does this 5-10 times every time we hang out. Apparently a family member bought him the notebook because he used to pull out his phone to take notes and that seemed way more rude.
“Aren’t you going to ask me how I knew?” He asked. I played along.
“Well, whenever there’s a guy ordering that seems to have been paying attention to someone good looking in front of or behind them in line, they order hot habanero sauce. I think they must think it’s manlier or something. I guess ordering the mild isn’t a turn on.”
A few minutes later he tapped me - hot habanero. On cue, a guy in a puffy jacket confidently echoed “hot habanero. Extra, if you can.”
I once asked my friend about his notebook habit and he responded that a writers job is simple - notice things about people, and write them down. The funny things, the quirky things, the things other people miss. That type of depth of understanding adds layers to the writing, he said. Also, he continued, it’s hard as hell to make stuff up. I’m not a good enough writer to do that, and luckily there’s no need to. The stories I need, the answers to the test, are everywhere. I’d much rather catalog than dream them up.
Writers and entrepreneurs are similar in that way. A writers job is to notice things about people everyone else misses and write them down. An entrepreneurs job is to notice things about people everyone else misses and then build those people a product based on the things they’ve noticed.
When entrepreneurs try to make stuff up, it usually goes badly.
The similarity, obviously, is the noticing. That’s always been the super power and it always will be. Every bit of tech makes it easier to scale an insight, but chatGPT and every other flashy new piece of software is nothing without the insight that you need to earn through noticing.
And THAT is why you should create content, especially during the early days. Not because it’ll help your business grow, although it will if you do it right. Not because it’ll help your personal brand, although, again, it could. But because creating content forces you to notice. It forces you to catalog. It forces you to get something you believe about your customer out in the world - to put a stake in the ground. And then, it gets you feedback. Does what you noticed about your customer actually matter to that customer? If you have that baseline, you’re way more likely to build a great product.
People talk about MVPs a ton. The smallest version of your product that works, that’ll show whether you can solve someones problem. If your finished product is a car, your MVP is a skateboard, and that’s what we call them at Tacklebox. Skateboard products.
Content is a way to test your insights even before you build any sort of product. Content is a way to force yourself to pay attention.
So, let’s do that.
After… a word from our friends at Byldd.
—
—
how to start
There’s a book I love called Bird by Bird - Instructions on Writing and Life , written by Anne Lamott. It’s hilarious and insightful and a great read, especially if you’re trying to learn how to write well, which is a super power for entrepreneurs.
In the first sentence of the first chapter Anne says that good writing is about telling the truth, and telling the truth is a great place to start with your content for your business, too.
An exercise I love doing with founders is to have them map out the big river and dam model we always use - the river taking their customer to their big, final goal, and the dams being the blockers in the way that stop them from getting anywhere.
Once we identify a bunch of blockers, I have the entrepreneur tell me the truth about each blocker. The real reason the entrepreneur can’t get past it.
Here’s an example.
I believe we’ve talked about OAR in the past - a company that came through the program a while back that helps people with alcohol addiction. The delivery method is Naltrexone, a seldom prescribed drug that is extremely effective for some people addicted to alcohol. The medication gets rid of the feeling people get that makes them want to have a 3rd and 4th and tenth beer after the first two. Instead, it just makes you feel like you’ve had to big cans of water. You’re full. You don’t want any more.
Early on, during the first few weeks of the program - pre-product, pre the founder leaving their job - pre really anything but an idea, we were going through this sort of exercise with the founder - going through the lifecycle of their customer, moving down the river from alcohol addiction to control over how much they drank, if anything.
One of the early dams for this customer was listed as general awareness of naltrexone.
I asked the founder to tell me about that damn. The truth about it that he’d noticed that other people missed.
“Well, it’s actually less that people aren’t aware of Naltrexone, and more that they’re hesitant to ask their doctor about it.”
Why, I asked?
“Well… I think a lot of these people have been telling their primary care doctor for years that they have a couple drinks a week when they’re asked at checkups. It’s really embarrassing then to come in and say hey, I’ve actually been lying to you for 4 years - I actually have 10 times as many drinks then I’ve told you. It seems silly, but it’s a really hard thing to do. And most people don’t. In interviews people told me they’d love to try it, but didn’t want to have that conversation with their doctor.”
There’s some truth. Something he noticed but most other people hadn’t.
And, that’s a piece of content.
He wrote an article with a headline around how to try pharmaceuticals when you haven’t told your primary care doctor about your drinking problem. The content then helped the reader navigate the dam. There was a script they could literally copy and paste and send to their doctor portal about how they hadn’t been straightforward about a problem but wanted to explore solutions. There were instructions for setting up an appointment with a telehealth doctor who could prescribe naltrexone if they didn’t want to have that talk with their primary care doctor. And there was a story of someone who went on Naltrexone and turned their life around.
That piece of content did exceptionally well.
The writing quality was irrelevant. It was just describing an unspoken truth, then cataloging someone else’s experience. People who had the problem felt like the article was speaking directly to them. Speaking for them.
We’ve talked before about the components of trust. I think of it like a see-saw. On one side is traction, on the other is specificity.
The customer would’ve trusted OAR if they already had a ton of traction - if they knew 5 friends who’d tried it and it’d helped with their alcohol addiction. But they hadn’t launched yet. So, they had to rely on specificity. I understand this moment in your life better than anyone.
That makes people who don’t know you, trust you.
When our founders are looking for this sort of moment to create content around, my response is always to look in the hole.
What I mean by that is find customers that have dug themselves a bit of a hole. Customers that know they’re in a hole. That know they’ve made decisions to make that hole deeper or to dig it in the first place.
Your content acknowledges the hole, and throws them a ladder.
You got yourself into this mess, but we’ll help you get out of it. With as many specifics as possible. If people gravitate towards the content, it’s fairly likely they’ll gravitate towards the product that solves the problem far better than content ever could.
The content OAR created did three things:
It Validated that the insight - people not telling their primary care doctor - resonated. That lots of people who saw it would gravitate towards it. They’d trust it.
It tested acquisition channels - the article was sponsored in a bunch of different channels and forums and newsletters, and the conversion - there was a link for OAR which would let you sign up to know more about how they’d help people with alcohol addiction - tracked what channels delivered the most high quality customers.
It gave insight into the initial product. Matching customers with a virtual doctor would become a critical feature.
The article wasn’t especially well-written or funny or witty. It just told the truth - here’s the reality of a situation that most people don’t know about. And, it was useful - here’s how to help that situation.
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Content as a system
Another question we get a lot is how frequently should I create content?
The better way to think of this is to map out the jobs of your content. In general, there are three.
Top of funnel, mid funnel, and brand building.
We’ll start with top of funnel.
I visualize this like those old sticky, slimy, stretchy toys that looked like long hands you had as a kid. The ones that you would hold one end of and throw the other end against the window and it’d make the big slap sound and then stick. Top of funnel content is the stuff that you’re pushing out over and over that is trying to pull people in. It’s a great place to test all the insights you learn about customers for all the dams in their river. It’s often evergreen, there’s some paid advertising behind it eventually, and it lives forever in places like your FAQ. It’s useful and helpful for solving an edge of wedge problem. The thing that builds enough trust that people convert after reading it. It’s classic rivers and dams.
Top of funnel is critical for testing out the insights that matter and the channels that convert. This is high priority for every startup.
Mid funnel is the content that’ll live in something like an onboarding email flow. After you’ve got a customer interested, you might drip them 3 or 5 or 7 emails that teach them stuff. That show them examples of other people being successful. That go deeper on the hole they’re in and the ladder you’ll give them.
This is high value content that entrepreneurs usually drag their feet on creating because it feels very permanent. This is the onboarding everyone will see, so it has to be perfect. Which usually means it’s ignored for far too long. The better approach is to edit it constantly. To continue learning more truths from your customers and updating this flow accordingly.
Finally, there’s brand building. The stuff that fills all the channels that you think of for content traditionally. The stuff that makes people uncomfortable. Linkedin, Twitter, Instagram, Tik Tok. What we call discovery channels.
Early on, all of this content is doing two jobs for you - testing insights and testing channels. You’re seeing what resonates and what converts.
Here’s what it looks like.
The other day I spoke with someone working on a startup that’ll help people take care of their plants. His idea was that he’d do a zoom call with customers who had plants that were dying. He’d diagnose the problem then give a solution in a follow-up email with affiliate links for soils or products where needed.
He wanted to test all of this with a content strategy, so we talked through a quick river and dams model with his customer. First, we had to narrow in on a customer with a bleeding neck problem, which I was skeptical about. It seemed that if someone was that interested in their plants that those plants dying would be a bleeding neck problem, they’d know how to take care of them. But his pitch was that new home owners - people that bough a house in the last year or two, specifically after moving from an apartment - often bought a few expensive, big plants. And those plants often started dying fast. And the last thing the home owner wanted was a half-dead fiddle leaf fig tree in their entryway.
The first dam was after they’d googled how to save my fiddle leaf fig. There was too much content - six ways to diagnose what’s wrong with your fig, ten common mistakes, and on and on. The founder had written a few of these and pushed them into the ehter, where they landed on the 7th page of Google, never to be heard from again.
He’d also created content for people who had signed up at his website - a drip campaign with a few emails showing pictures of before and after plants he’d helped. These seemed to do OK, but he had no top of funnel, so no one was getting to this stage.
Finally, his brand building on discovery channels was a tik tok account where he did a daily video on a specific type of plant he liked. Underrated plants, he called them.
This… was not a big hit.
So, we talked about cataloging.
Humans learn through stories. We build trust through stories. A how to video actually isn’t all that helpful a lot of the time. What is helpful is context. So, his new strategy became recording his zoom calls with customers, editing them into 90 second videos, and posting them to Tik Tok and Instagram. Specifically, he left in all the questions the customer ha asked about light and water and yellow leaves and all that. Then, he’d talk through his approach. He’d talk about similar fig trees or snake plants that’d he’d helped revive.
The whole thing exploded.
And, it was way easier for him to create content. Each customer was new content. He didn’t to think. The answers for the test were out there.
Cataloging is always better than creating.
There’s obviously way more we can dive into for top of funnel, mid funnel, discovery channels and brand building. The pace of the article matters - something Nathan Bazchez calls Thrust and Drag - but, being light on all of that was sort of the point of this podcast.
Because the important part about creating content is the act of creating it. Of forcing yourself to notice stuff about your customer other people don’t. Of forcing yourself to go through each of the dams your customer hits and try to get to the truth of that moment - the real reason they’re unable to get past it. Of finding your customers that have dug themselves holes and cataloging exactly how you’ve gotten other people out of holes so that you can help them.
The important part of content is the noticing bit.
Whenever people are stuck on creating content, I have a very easy and annoying answer. Speak with your customers. Have them tell you about the hard stuff. Have them tell you about why they can’t solve a problem. Then, write that down.
EB White has one of my favorite quotes of all time - don’t write about man, write about a man. Tell the stories of your customers interacting with problems, and the useful things you did to help them overcome them. That’ll build trust and inform you on what to build for a product.
Get an opinion of yours out in the world and see if your customer latches on to it. If you can speak for them.
And now I’m off to get a burrito from Dos Toros because I’ve been thinking about it since the beginning of the episode and I’m working from the city today. Hot habanero, please.