Nov 16, 2023 · 43m · startup-ideas
How To Make Money As A Creator | Nathan Barry (ConvertKit)
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
ConvertKit founder Nathan Barry joins Greg Isenberg to break down the mechanics of modern audience building, the power of quest-driven storytelling and edutainment, and the strategic transition from service agencies to high-multiple software businesses.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 31% of the talking time here. How this is scored →
Greg as informed peer 5.8 Guest teaching 5.8 Guest disagreement 1.4 Greg pushing back 0.7
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 6:57 Nathan directly rejects Greg's premise on inherent interest
Nathan straightforwardly contradicts Greg's assertion that every person on the planet is interesting, arguing that most people lack the narrative structure and transformational journey needed to be compelling.
Hardest push from Greg ▶ 10:27 Greg reframes and defends ordinary storytellingGreg clarifies his stance against Nathan's pushback, breaking down creator archetypes and arguing that even mundane experiences become compelling if given proper contextual packaging.
Biggest teaching moment ▶ 7:15 The manuscript evaluation filter and hero's journeyNathan explains how book editors evaluate manuscripts solely by checking character change between the start and end, illustrating why active personal transformation is essential for creators.
Greg holds their own ▶ 31:00 Greg's thesis on the failure curve of productized agenciesGreg demonstrates operational expertise by diagnosing the hidden scaling liabilities, client quality variances, and margin collapse facing creator-founded productized agencies.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| The Web App Challenge and Starting ConvertKit | 5 | 5 | 1 | 1 | Greg sets the agenda by identifying Nathan as a central node in the creator space and asks for non-obvious audience builders. Nathan explains S-tier niche audience strategies using Shaan Puri and Sahil Bloom/Siava Kaczynski as case studies. | |
| Being Interesting Off the Internet: Authenticity and AI | 6 | 5 | 1 | 1 | Greg offers a thesis on AI commodifying generic content and the necessity of unique personal perspectives. Nathan builds upon this with the Envato founder's aphorism to be interesting off the internet first. | |
| The Hero's Journey: Why Creators Must Have a Quest | 4 | 8 | 6 | 1 | When Greg asserts that everyone is inherently interesting just by existing, Nathan explicitly disagrees and rejects the premise. Nathan breaks down the hero's journey framework, explaining why unguided routines fail to make engaging content without an active transformation. | |
| Transforming Mundane Experiences into Compelling Stories | 6 | 6 | 2 | 2 | Greg pushes back to refine his point, distinguishing between B2B creators and everyday storytelling craft. Nathan reconciles the views by demonstrating how mundane jobs become interesting through explicit quests and deliberate packaging. | |
| The Edutainment Formula: Commercials and Bag Reviews | 5 | 5 | 1 | 0 | Nathan breaks down edutainment using Chase Reeves and Ryan Reynolds' Mint Mobile commercials as examples. Greg connects this to shifting media consumption patterns and lo-fi iPhone production styles. | |
| The Power of Video and Practicing Comedy | 6 | 4 | 0 | 0 | Greg cites Shaan Puri's viral application video to illustrate organic video leverage, admitting his personal friction with video creation. Nathan offers practical routines for treating humor as a daily practiced skill. | |
| Learning the Craft of Humor: David Nihill's Public Speaking Lessons | 4 | 7 | 1 | 0 | Nathan recounts David Nihill's speech punch-up agency methodology, illustrating specific comic timing adjustments to speech delivery. Greg listens and affirms how learnable and tactical these skills are. | |
| The Economic Leverage of Undervalued Creative Skills | 6 | 6 | 1 | 0 | Greg and Nathan analyze the economic transformation where historically underpaid skills like writing and teaching gain massive leverage online. Nathan provides an example of a schoolteacher earning seven figures through course products. | |
| Ladders of Wealth Creation and Cross-Industry Inspiration | 5 | 6 | 1 | 0 | Nathan outlines his Ladders of Wealth Creation framework and borrowing business model ideas across unrelated niches like ghost towns and fashion design. Greg facilitates the transition smoothly into monetization taxonomy. | |
| The Pitfalls of Scaling Productized Agencies | 7 | 5 | 2 | 2 | Greg lays out a clear critique predicting the death of productized creator agencies within 18 to 24 months due to scaling bottlenecks. Nathan agrees and expands on the operational friction of high client variation and misaligned skills. | |
| Strip Malls vs. Skyscrapers: Optimizing Creator Portfolios | 8 | 6 | 1 | 1 | Greg presents his real-world portfolio of agency and community assets to seek concrete advice. Nathan introduces the mental model of strip malls versus skyscrapers, urging focus on high-multiple software assets. | |
| Combining Agencies and Software: The Brennan Dunn Case Study | 7 | 6 | 0 | 0 | Greg details how his SEO agency decided to spin out a software SaaS layer. Nathan validates this strategy using Brennan Dunn's RightMessage and Slice and Dice agency model as an exact precedent. |
Statements from this episode (23)
Barry: 30k high-net-worth subscribers beat 300k food blog readers
“Like I'd much rather take 30,000 people interested in investing and buying businesses who are higher net worth people on that one side compared to like 300,000 who are reading a food blog and nothing against food blogs. It's just like the intent or the amount …”
Isenberg: Content copying will decline as AI automates it; unique stories will win
“My thesis is that that's going to be less and less of a thing over time as AI helps automate a lot of that. So the people that are going to win are going to be sharing unique perspectives and stories.”
Barry: If AI could have written it, it is not worth publishing
“Especially with writing being done by AI right now, a filter that I like to use is if I'm writing something, could AI have written this? If yes, it's probably not worth me publishing.”
Barry: Most people are uninteresting because they lack storytelling fundamentals
“I think that most people are actually really not interesting at all, because they don't know, like, the fundamentals of a good story.”
Nathan Barry: The best way to be interesting online is pursuing transformative quests
“The best way to be interesting on the internet is to be going on a quest that is going to change you and that is worth following.”
Barry: ConvertKit began as a challenge whose initial revenue goals failed
“I said, I'm going to build a SaaS company to 5000 dollars a month in recurring revenue in six months with only 5000 dollars of my own money. And I called it the web app challenge. And that is what ultimately became ConvertKit. I didn't hit any of my goals.”
Nathan Barry: Creators only need either a compelling journey or great storytelling
“Someone who is the best at both, they're going to have a much easier time building an audience, but you could be mediocre at storytelling and have a compelling journey, or you could have a mediocre journey and be compelling at storytelling. And either one of t…”
Barry: Adding entertainment value expands educational content reach
“Anything you're trying to teach. The more you can add an entertainment value to it, often the more people it's going to reach.”
Isenberg: Audience demand favors casual, iPhone-style entertainment video
“Cause it's approachable, but also because the platforms are prioritizing video. Creators are going to want to create more video. Brands are going to want to create more video. Products are going to want to create more video. And the type of video people want i…”
Barry: Creator status has shifted from high-end gear to accessible tools
“It used to be cool to say like, oh, I had this red camera or whatever the equivalent is. In your industry, right? The absolute best of whatever, and it's polished and perfect. And now it's cool to be like, yep, I didn't do that. I did it this other way. We all…”
Isenberg: Shaan Puri's self-made All-In application surpassed one million views
“It has well over a million views. He basically shot it himself, edited it on iMovie. It's his job application to work at the all in podcast.”
Barry: David Nihill's agency punches up keynotes by measuring laughs per minute
“What he did is he got a bunch of his comedy friends together and said, we were going to make an agency where we will punch up your business talks. You bring a talk that you've already done, and you send it to us, and we will write it no more than five percent,…”
Barry: Creative skills provide massive online leverage by capturing attention
“And it's just because, comedy, writing, teaching, all of these things are so, so valuable at capturing attention. And then you can drive that attention to whatever you want. And you get leverage in a really interesting way.”
Isenberg: Top writers like Sahil Bloom make $5M a year
“Like, you used to get paid 50,000 dollars to write, and now the greatest writers, Sahil Blooms and the Nick Hubers, are getting paid five million dollars a year to write.”
Barry: High school teacher makes nearly $1M online teaching other educators
“Like I know a school teacher who makes almost a million dollars a year. Like teaching school teachers how to manage their classroom, how to show up effectively, how to create lesson plans, all of this stuff. And he actually still teaches part time at the high …”
Barry: Nick Huber makes bulk of his revenue from agencies
“He can make plenty of money off of sponsorships and digital product sales and traditional things, but he's actually making them like the bulk of his money off of two agencies with shepherd and his re costs egg.”
Barry: Cerro Gordo ghost town makes ~$50K monthly in YouTube sponsorships
“It has a YouTube channel. It makes like 50 grand a month in sponsorship revenue because the YouTube channel is so popular.”
Isenberg: Creator-Led Productized Agencies Will Die in 18 to 24 Months
“So my thesis is that you're actually going to see a bunch of creator led productized agencies die in about 18 to 24 months.”
Barry: Paid Newsletters Put Growth and Monetization in Direct Conflict
“Turns out I chose a business model that requires my best content to be behind a paywall. And then I need new content, not behind a paywall to get new readers. And like these two sides of my business are directly at odds, you know, growth and monetization are d…”
Barry: Creators Should Build One 'Skyscraper' Business Instead of Strip Malls
“And I think a lot of creators like to build strip malls. Here's what I mean. If you think about the footprint of land, what you can build, right? You're going to a strip mall and you're like, okay, I'm going to build this one little business here. Here's my ra…”
Barry: A Growing $10M ARR Software Company Is Worth Over $50M
“A software company doing ten million a year in revenue is worth more than fifty million dollars, right? If it's growing, growing well.”
Barry: Agencies bridge software's short-term cash flow problems
“Software is great at long-term enterprise value and terrible for a short-term cashflow. And so the agency kind of bridges that gap.”
Barry: Tutorials cannot match done-for-you agency onboarding for software
“No amount of like onboarding and help tutorials will ever turn someone into the perfect user. But when you're like, all right, fine, I'll like pay me and I will just set it all up for you. It turns out that works pretty well.”