Marketing 23 guests | 35 insights

Content Marketing

Content marketing is how you earn attention instead of buying it. The best content marketers create genuinely valuable material that builds trust and authority over time—making sales conversations easier because prospects already know and respect you.

The Guide

4 key steps synthesized from 23 experts.

1

Start by identifying your unique point of view

Don't create content that anyone could write. Your content should reflect a distinct perspective or expertise that only you can provide. This 'earned secrets' approach—sharing insights from your real experience—creates content that stands out and builds genuine authority.

Featured guest perspectives
"The spicy take is like, here's what a lot of people get wrong. The spicy take is, I am prepared to have the courage of conviction and plant my flag and say, this is what I believe."
— Wes Kao
"We're seeing a shift from 'keyword-first' to 'audience-first' content strategies... creating content that speaks to a specific audience's pain points and questions."
— Amanda Natividad
2

Obsess over the headline and hook

Your content lives or dies in the first few seconds. Spend disproportionate time on your headline and opening—they determine whether anyone reads the rest. The best hooks create curiosity or promise a specific, valuable outcome.

Featured guest perspectives
"Packaging matters more than people think... your content's value is only realized if people actually consume it, and that starts with the hook."
— Kieran Flanagan + Scott Tousley
"The headline is the gatekeeper... If your headline doesn't work, nothing else matters."
— Jimmy Daly
3

Distribute relentlessly across multiple channels

Creating content is only half the job—distribution is the other half. Repurpose each piece of content for multiple platforms: turn a blog post into a Twitter thread, LinkedIn post, newsletter, and podcast topic. Most content fails from under-distribution, not poor quality.

Featured guest perspectives
"One interview could become a long-form written piece, a podcast episode, social snippets, an email series... Think about the content flywheel from the start."
— Camille Ricketts
"The best marketers I know spend as much time on distribution as they do on creation. Content without distribution is just a diary entry."
— Amanda Natividad
4

Create content that addresses objections before sales conversations

Strategic content marketing anticipates and answers buyer objections before they arise in sales calls. Write about pricing philosophy, implementation challenges, and comparison guides—so prospects arrive educated and pre-sold.

Featured guest perspectives
"We created content for every single objection we heard in sales calls... By the time prospects talked to sales, they'd already read answers to their concerns."
— Ashley Deibert

Common Mistakes

  • Creating generic content that anyone could write instead of leveraging unique expertise
  • Spending 90% of time on creation and 10% on distribution (should be closer to 50/50)
  • Writing for search engines instead of real people with real problems
  • Expecting results too quickly—content marketing compounds over 6-18 months

Signs You're Doing It Well

  • Prospects mention your content during sales calls
  • Your content gets shared by people in your target audience
  • Inbound leads reference specific articles or topics you've covered
  • You're seen as a thought leader in your space

All Guest Perspectives

Deep dive into what all 23 guests shared about content marketing.

Ada Chen Rekhi 1 quote
Listen to episode →
"I know a lot of people have talked about doing a LinkedIn 30. So 30 days of posting something on LinkedIn in terms of content every day for 30 days straight, and just getting past that barrier of sharing."
Tactical:
  • Commit to a 'LinkedIn 30' to force the habit of sharing insights.
  • Write for an 'audience of one' to make the process feel more authentic and less like self-promotion.
  • Focus on crystallizing a thought that is useful to you rather than chasing viral metrics.
View all skills from Ada Chen Rekhi →
Andy Raskin 1 quote
Listen to episode →
"What I find is like, yeah, there's this a while where you're writing and it feels like you're talking to nobody and then gradually it grows and you'll have these peaks, but then over time is where the magic is."
Tactical:
  • Focus on long-term consistency rather than expecting immediate 'boom' results.
  • Use platforms like Medium or LinkedIn to build an audience without intermediaries.
View all skills from Andy Raskin →
Barbra Gago 1 quote
Listen to episode →
"And then tactically, it's a lot of content marketing and a lot of thought leadership. When you're building a category, you need to make sure that there is a category that's validated by analysts and directory sites and things like that... And then of course, getting a lot of content around because when you're generating a new category, you're also needing to educate buyers that there is a category that they can now budget for and why they should allocate budget for that."
Tactical:
  • Produce high volumes of content to educate the market on the new category
  • Use content to explain why a new budget line item is necessary
View all skills from Barbra Gago →
Ben Williams 1 quote
Listen to episode →
"We have a side car product called Snyk Advisor. Snyk Advisor, it's basically a service that developers use to search and find open source packages when they're considering integrating some within their software applications... anyone searching on Google for a package that does X, Y, Z or a specific package by name, Snyk Advisor will be right up there in terms of the search results."
Tactical:
  • Build programmatic SEO assets that index high-intent search terms
  • Provide free utility or data (like security scores) to attract users from search engines
View all skills from Ben Williams →
Camille Hearst 1 quote
Listen to episode →
"One of the things that I've seen that I don't know if people realize is consistency and predictability of content creation... there is something to churning out consistent quality work and putting it out there for your audience to consume and respond and react to that goes a long way. It's almost like the 10,000 hours."
Tactical:
  • Maintain a consistent schedule to build audience habits
  • Focus on 'churning out' work to reach the '10,000 hours' of mastery
View all skills from Camille Hearst →
Cam Adams 1 quote
Listen to episode →
"He set up a whole team of people who looked at people's motivations and the top jobs to be done that Canva could service. He then mapped that through the entire experience of going into Google, typing a search query, getting that search query, seeing that it was a great result, firstly getting to the top result, but then also the experience after they landed on Canva."
Tactical:
  • Identify high-volume 'Jobs to be Done' (e.g., 'Halloween poster') and create dedicated landing pages
  • Ensure the post-click experience takes the user directly into a relevant template to fulfill the search promise
View all skills from Cam Adams →
Camille Ricketts 3 quotes
Listen to episode →
"The way that you think about product market fit, you have to think about content market fit. So even though content feels like it's running adjacent to the actual product that you're putting out there, you still have to think about who is my audience? ... What is it that they need to get promoted? What is it that they need to avoid failure? What is it that causes them a great deal of anxiety in the day-to-day of their lives or their work? And can you create some type of content product that is going to address this for them?"
Tactical:
  • Identify the specific professional needs of your audience (e.g., getting promoted, avoiding failure)
  • Treat content as a product that addresses user anxieties
"painkillers always win. So can your content be a painkiller? Can it help people out of situations that are causing them a lot of pain? Can it help people stop being so confused or can it make them even feel less alone in their experience?"
Tactical:
  • Focus content on solving specific 'pain' points rather than just providing 'vitamins' (general info)
  • Share failures or suboptimal situations to help the audience feel less alone
"It would take eight hours to just write the thing. And that's after you had done all of the prep work of making sure that your interviewee was feeling really anchored and understanding a topic that you were both really excited about and making sure you were mining all of the tactical gems from that conversation."
Tactical:
  • Spend time 'mining' tactical gems from interviews rather than just transcribing
  • Allocate significant time (8-10 hours) for the actual writing and synthesis process
View all skills from Camille Ricketts →
Chris Hutchins 1 quote
Listen to episode →
"make clips of your podcast and you could put those clips on these channels that do have that built in distribution... TikTok, YouTube, Instagram Reels... brand awareness for me."
Tactical:
  • Create high-quality clips of long-form content for TikTok and Reels
  • Use these platforms for brand awareness even if direct attribution to downloads is low
View all skills from Chris Hutchins →
Christopher Miller 1 quote
Listen to episode →
"One of the channels that we're spending some time experimenting with is this concept of microapps... Website Grader... you put in your domain, and it crawled your site, and then gave you a set of recommendations... It was definitely a one trick pony. But what it did was it created an interesting conversation"
Tactical:
  • Build 'one-trick pony' tools (e.g., graders, generators) that solve a specific, narrow problem
  • Use the output of a free tool to transition the user into a conversation about the full product suite
View all skills from Christopher Miller →
Claire Butler 1 quote
Listen to episode →
"I got him to make technical content and that, I think, went to number one on Hacker News... I remember one of my bars were deciding if something would hit this or not... "Did I understand it?" And if I understood it, it was probably too basic, or if I could have written it myself, it was probably too basic."
Tactical:
  • Set a high bar for technical depth: if a non-technical marketer can write it, it's too basic
  • Leverage engineers and designers to write about the 'how' and the craft behind the product
View all skills from Claire Butler →
Emilie Gerber 2 quotes
Listen to episode →
"The standard press release format, it's so formulaic, and I think it actually encourages that more marketing speak. The benefit is that you're getting all the news details in one place... However, you can do the exact same thing in a blog post."
Tactical:
  • Use a first-person blog post instead of a formal press release for announcements
  • Include all news elements in the blog post to serve as a resource for reporters
"If you're going to do that [social strategy], have an exec that you're also trying a social strategy with. Don't just do the plain corporate channels. Corporate channels, it's very hard to build a following... When you have an executive, you're following a personality."
Tactical:
  • Prioritize executive social presence over corporate brand channels
  • Focus on building a personality and tone for the executive spokesperson
View all skills from Emilie Gerber →
Ethan Smith 2 quotes
Listen to episode →
"The future of content is clearly AI-assisted. Clearly, you and I will be using AI to help us write, so it's not no AI at all, but it's not 100% generated with AI."
Tactical:
  • Use AI to draft or structure content but ensure human experts provide the final polish and unique insights.
  • Avoid 100% automated content generation as it lacks 'information gain' and is easily detected by search algorithms.
"One concept would be information gain. So did you say something that somebody else didn't say? Two is how typical are you? Are you so typical that I think that you're a rewritten version of somebody else's content?"
Tactical:
  • Conduct original research to ensure your content provides 'information gain.'
  • Avoid 'typicality' by including domain expertise and unique perspectives that AI cannot easily replicate.
View all skills from Ethan Smith →
Gergely 2 quotes
Listen to episode →
"I started a blog six years before... I said, 'I'm going to start a blog, it'll be about software engineering and I'll call it The Pragmatic Engineer.'... I said, 'I'm going to do what Jeff Atwood said. I'm going to publish... every two weeks I'm going to publish an article, and I'll do it for a year.'"
Tactical:
  • Commit to a regular publishing cadence (e.g., every two weeks) for at least a year to build momentum.
  • Focus on a specific niche (e.g., pragmatic software engineering) rather than general topics to attract a dedicated following.
"I announced my newsletter, I told people, 'I'm going to go full time on this.' I had maybe 10,000 Twitter followers and, I don't know, maybe 1,000 on LinkedIn... What I didn't tell is that there was at least six years of accidental work behind this."
Tactical:
  • Build a presence on platforms like Twitter and LinkedIn years before you intend to monetize them.
  • Use a personal blog as a long-term repository for insights that can eventually be converted into a newsletter or book.
View all skills from Gergely →
Gokul Rajaram 1 quote
Listen to episode →
"My rule of thumb is when they do a search for you on Google, if your LinkedIn profile is the first thing that comes up, you've probably done something wrong. What should come up is an article you wrote. Is a tweet you published."
Tactical:
  • Write and publish non-obvious insights about your specific domain (e.g., payments, risk, crypto)
  • Aim to have your own content outrank your social profiles in search results
View all skills from Gokul Rajaram →
Julian Shapiro 2 quotes
Listen to episode →
"Generally speaking, threads, despite everything I've said, are the primary way to get followers. There's a reason why people do threads as opposed to single tweets is because when people get exposure to a thread, they're basically getting exposure to the length of thoughts equivalent to you having sent a newsletter edition or a blog post in many cases."
Tactical:
  • Use long-form threads (up to 30 tweets) to prove consistency of thought
  • Use clickbaity opening tweets to trigger the initial click
  • Port followers from your website or newsletter to provide an initial sample audience
"I'm spending as many hours going back and rewriting old blog posts and handbooks as I am writing ones. If you come back to anything I've written over the course of a year or year and a half, it'll be updated, because I consider everything I write to be evergreen."
Tactical:
  • Avoid writing about newsy trends that expire quickly
  • Regularly update old content to keep it relevant and accurate
  • Use handbooks as a middle ground between newsletters and books for better UX and SEO
View all skills from Julian Shapiro →
Laura Modi 1 quote
Listen to episode →
"We wanted to become the content leaders in that, with the hypothesis... that if we win on content and as a thought leader, that will drive back to Bobbie. And today... if you do a cursory Google search for something like 'How long does formula last?' Milk Drunk is showing up between the CDC and the bum on the first page of Google."
Tactical:
  • Create a separate content platform (e.g., a blog) to address customer education needs.
  • Focus on high-intent SEO keywords that establish your brand as a thought leader.
View all skills from Laura Modi →
Lulu Cheng Meservey 3 quotes
Listen to episode →
"Going direct... means that the founder or executive for some very senior person has to be speaking from themselves. First person, may be first person plural, and speaking in a human voice authentically. You see them make mistakes, you see them be vulnerable, and they have to become an ambassador to the community."
Tactical:
  • Identify the spokesperson's dominant communication style (long-form, video, audio, or short-form).
  • Invest heavily in one primary channel that fits the spokesperson's natural strengths before expanding.
  • Avoid ghost-writing that sounds corporate; maintain a human, vulnerable tone.
"LinkedIn is super underutilized because it gets a ton of eyeballs in time, but most of the content sucks... the ratio of your competitive set of interesting content versus how much time and attention people spend on there is excellent."
Tactical:
  • Post genuinely interesting and useful content on LinkedIn to stand out against generic corporate updates.
  • Use LinkedIn specifically for career-related or professional audience targeting.
"Step one would be assessing what are you good at and what do you enjoy... Step two is setting up your account on those channels... And then you start building your audience. And when you start if you're actually starting from zero, get some pipeline of content ready... get a week or two of posts ready to go."
Tactical:
  • Prepare 1-2 weeks of content before launching a new channel to build momentum.
  • Prioritize consistency over trying to go viral with every single post.
  • Focus on providing value to a specific audience rather than chasing 'low-value' viral likes.
View all skills from Lulu Cheng Meservey →
Meltem Kuran 4 quotes
Listen to episode →
"I'm a huge fan of SEO, happy to discuss that later, but if people aren't asking this question to Google, you can write all the content you want, it doesn't matter, nobody's going to find it."
Tactical:
  • Verify that people are actually asking the question on Google before writing content.
"The biggest mistake people make is they will just shove keywords. They're like, 'Okay, these are the keywords people are searching for, I need to make sure I mention it five times.' Obviously do that, make sure that the content that you wrote answers the question. But the main thing to think about it is, is the Google search over? If someone reads your content, if they typed in something to Google, and then they read the article that you've published, are they going back to Google to continue reading more or is the Google search over?"
Tactical:
  • Focus on 'ending the search' rather than just keyword density.
  • Write content that answers the primary question and the likely follow-up questions.
"We have this framework that we call the traffic light system. Essentially we go, whenever the team is going to do a content series, they will go and find up to 700 keywords... And then those set of keywords get ranked by highest volume to the lowest volume... And then you go one by one... and say, what is the intent of someone searching this keyword?"
Tactical:
  • Rank keywords by volume and then categorize by intent (Green: high intent/ready to buy, Yellow: mixed intent, Red: no intent).
  • Execute from Green highest volume down to Yellow, often ignoring Red entirely.
"We use Clearscope, we love it... those tools will give you a score to say you're an A plus or you're a C minus, you need to make your language less sophisticated, currently it's at university level and we need it to be at fourth grade reading level."
Tactical:
  • Aim for a low reading level (e.g., 4th or 5th grade) to ensure clarity and accessibility.
View all skills from Meltem Kuran →
Paul Millerd 1 quote
Listen to episode →
"Podcast is the ultimate long game, so you need to find some intrinsic connection to what you're actually doing. If you don't love the conversations or the format you're doing, don't do it."
Tactical:
  • Choose a content format (podcast, newsletter) that you would enjoy doing even if it lost money
  • Commit to a 'long game' mindset for podcasting growth
View all skills from Paul Millerd →
Ray Cao 1 quote
Listen to episode →
"Number one thing is that you have to really be unfiltered. I mean, you don't really need to be perfect on this platform. I mean that's the beauty of it. You can be yourself, you can really share the things that you like."
Tactical:
  • Focus on being relatable and showing a 'different side' of the brand or person.
  • Embrace the community culture by listening to user behaviors before creating.
View all skills from Ray Cao →
Sriram and Aarthi 1 quote
Listen to episode →
"The most important thing... is just get started and do something every single day... it builds muscle, it gets you familiar with the medium and you start understanding what works in that medium and what doesn't and you start building reps."
Tactical:
  • Post content every single day to build the creative muscle.
  • Focus on being authentic and relatable rather than just projecting an expert persona.
  • Share niche expertise you've actually practiced rather than 'LARPing' as an expert in broad topics.
View all skills from Sriram and Aarthi →
Yuriy Timen 2 quotes
Listen to episode →
"I think with SEO, it's like the first pillar I would say is, do you have a unique angle... Do you have a unique programmatic angle, right? For instance, Canva did dealt with templates... do you have a unique data angle?"
Tactical:
  • Audit the SEO landscape for 'how-to' searches to find editorial gaps.
  • Identify programmatic opportunities like templates or landing pages for long-tail keywords.
  • Leverage proprietary user data to create unique search experiences.
"SEO is now becoming more attractive because once you got your burn under control and you're thinking, "Okay, we saved all this money by reducing our paid budget. We're cutting it entirely. How do we put some of those resources back to work?" And all of a sudden SEO starts looking a lot more lucrative because it's almost like you took the urgency of grow at any cost in the next six months, you took that out of the equation."
Tactical:
  • Shift resources from paid media to SEO when extending runway becomes the priority over short-term growth spikes.
View all skills from Yuriy Timen →
Zoelle Egner 1 quote
Listen to episode →
"Make sure that you have also set up a process to take the insights that your customer success people are coming up with and turn them into as much content as you can... we would talk to a bunch of customers and then customer success would have helped them build bases, and then we would create templates."
Tactical:
  • Create a 'conveyor belt' to turn individual customer solutions into generic templates
  • Use real-world workflows as the basis for blog posts and educational resources
  • Share templates with smaller customers to scale support without increasing headcount
View all skills from Zoelle Egner →

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1

Download the skill

Download SKILL.md
2

Add to your project

Create a folder in your project root and add the skill file:

.claude/skills/content-marketing/SKILL.md
3

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Help me with content marketing