
How Nathan Barry Made $50K From a Passive Evergreen Newsletter
03/07/23 • 48 min
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You may be familiar with traditional newsletters, but an evergreen newsletter is a smart and automated approach to standard email newsletters. It allows established creators to step off the content hamster wheel, build a personalized journey for new subscribers, and make better versions of future email sequences based on audience feedback.
Nathan Barry, CEO of ConvertKit, has made $50K from “a secret newsletter about money.” He noticed that a lot of content existed for new creators, but not for established ones. Nathan’s “Secret Money Newsletter” is a paid $149 email sequence targeting established creators that make at least $200K annually. It currently has 500 subscribers and an impressive 87% open rate.
In this episode, Alyssa and Melissa talk to Nathan about the power of transparency and providing context behind success metrics, the advantages of an evergreen newsletter, and connecting with your audience by incorporating their feedback into future email sequences.
Key Takeaways
- [03:03] - What is Nathan’s paid newsletter about?
- [08:26] - Why Nathan is so transparent about his own finances, and is it worth it?
- [17:24] - How much revenue has Nathan’s paid newsletter generated?
- [22:36] - What is the most challenging aspect of an evergreen newsletter?
- [29:06] - Why evergreen newsletters are a great way to showcase your expertise.
- [32:30] - How an evergreen newsletter can remove the pressure of wanting it to be “perfect”.
- [34:21] - How to keep email sequences from overwhelming your subscribers.
- [36:45] - What are Nathan’s plans for the future of his newsletter?
- [39:59] - Why asking your audience for specific feedback makes it so much easier to keep writing content.
- [45:16] - Nathan’s method for coming up with content for future emails.
Quotes
[14:04] - “By putting advice out there, and real numbers, you show people what’s possible and they can learn from the specifics. It makes a huge difference when people share actual numbers, it gives you real context.” ~ @nathanbarry
[20:35] - “I love with email how few barriers there are between your ideas and the reader.” ~ @nathanbarry
[32:47] - “If you know this is going to be email #1 for a long time, that puts the pressure on it. But, good news — you can edit it. So 15 people will get that, and you can learn from it and so the version that’s going to go out to 500 people over a period of time is so much better, and a lot of the pressure comes off.” ~ @nathanbarry
Links
- Nathan Barry on Twitter
- Nathan Barry on LinkedIn
- Nathan Barry
- A secret newsletter about money
- Buy Back Your Time
- Subscribe to the monthly Deliverability Defined newsletter!
- Ask Alyssa & Melissa questions or suggest content for our next monthly newsletter!
Connect with our hosts
Stay in touch
Try ConvertKit's deliverability in action
It's now free to use ConvertKit with an audience of 1,000 subscribers or less! Start building your audience and reaching their inboxes: convertkit.com/pricing.
You may be familiar with traditional newsletters, but an evergreen newsletter is a smart and automated approach to standard email newsletters. It allows established creators to step off the content hamster wheel, build a personalized journey for new subscribers, and make better versions of future email sequences based on audience feedback.
Nathan Barry, CEO of ConvertKit, has made $50K from “a secret newsletter about money.” He noticed that a lot of content existed for new creators, but not for established ones. Nathan’s “Secret Money Newsletter” is a paid $149 email sequence targeting established creators that make at least $200K annually. It currently has 500 subscribers and an impressive 87% open rate.
In this episode, Alyssa and Melissa talk to Nathan about the power of transparency and providing context behind success metrics, the advantages of an evergreen newsletter, and connecting with your audience by incorporating their feedback into future email sequences.
Key Takeaways
- [03:03] - What is Nathan’s paid newsletter about?
- [08:26] - Why Nathan is so transparent about his own finances, and is it worth it?
- [17:24] - How much revenue has Nathan’s paid newsletter generated?
- [22:36] - What is the most challenging aspect of an evergreen newsletter?
- [29:06] - Why evergreen newsletters are a great way to showcase your expertise.
- [32:30] - How an evergreen newsletter can remove the pressure of wanting it to be “perfect”.
- [34:21] - How to keep email sequences from overwhelming your subscribers.
- [36:45] - What are Nathan’s plans for the future of his newsletter?
- [39:59] - Why asking your audience for specific feedback makes it so much easier to keep writing content.
- [45:16] - Nathan’s method for coming up with content for future emails.
Quotes
[14:04] - “By putting advice out there, and real numbers, you show people what’s possible and they can learn from the specifics. It makes a huge difference when people share actual numbers, it gives you real context.” ~ @nathanbarry
[20:35] - “I love with email how few barriers there are between your ideas and the reader.” ~ @nathanbarry
[32:47] - “If you know this is going to be email #1 for a long time, that puts the pressure on it. But, good news — you can edit it. So 15 people will get that, and you can learn from it and so the version that’s going to go out to 500 people over a period of time is so much better, and a lot of the pressure comes off.” ~ @nathanbarry
Links
- Nathan Barry on Twitter
- Nathan Barry on LinkedIn
- Nathan Barry
- A secret newsletter about money
- Buy Back Your Time
- Subscribe to the monthly Deliverability Defined newsletter!
- Ask Alyssa & Melissa questions or suggest content for our next monthly newsletter!
Connect with our hosts
Stay in touch
Try ConvertKit's deliverability in action
It's now free to use ConvertKit with an audience of 1,000 subscribers or less! Start building your audience and reaching their inboxes: convertkit.com/pricing.
Previous Episode

How to Fix Reputation Issues with Gmail
According to Finances Online, as of January 2020, Gmail had over 1.8 billion active users. When you’ve got a mailbox provider so prevalent on your email list, keeping yourself on good terms with that provider is essential for the survival of your subscriber count. But how do you know if your reputation with Gmail has tanked? And what’s the best way to respond?
While every mailbox provider cares about customers first, Gmail has its advantages for senders too. For example, Gmail allows you to track your domain and IP reputation. Gmail also sends helpful hints when your emails land in the spam folder, but it can be confusing.
In this episode, Alyssa and Melissa discuss how to determine where your sender reputation stands with Gmail, what to make of every possible inbox tip-off, how to respond when you realize your reputation has tanked, and reaching the root cause of your strained relationship with Gmail.
Key Takeaways
- [03:28] - There are many clues and data points Gmail provides that can point senders in the right direction when it comes to fixing your reputation.
- [06:37] - While Gmail is the mailbox provider, the actions of your subscribers determine where you land in the inbox. Remember that mailbox providers care about their customers (your subscribers) above all else.
- [07:34] - Subscribers will sometimes tell you when your messages are landing in their spam folders. Keep in mind that the promotions tab is still the inbox.
- [11:24] - If you land in the spam folder and see a banner that reads, “Why is this message in spam?” — it usually means you’re not using a verified sending domain with an ESP.
- [13:16] - If you realize you have a bad reputation with Gmail, immediately stop sending to unengaged subscribers and figure out the root cause.
- [14:07] - Clean your list, check to see if you’ve been listbombed, and avoid sending to unengaged subscribers for two weeks. As you see your reputation start to improve, you can gradually begin re-engaging subscribers who haven’t been receiving your messages.
Quotes
[06:59] - “Gmail’s number one priority is their customers, who are your subscribers. So you may have every good intention in the world of helping people, sending relevant content, but if those subscribers are not interacting in a positive way, then your reputation may be suffering.” ~ @mel_lambert_
[17:43] - “You have to give them time to build that trust back. And you want to make sure that in that process, when you’re building it back, you don’t do anything that would cause more negative signals to show up. Don’t try and re-engage your list too fast. You want to do all that really slowly and try to make sure that the most things they’re seeing when you send messages are those positive engagements like opens, and clicks, and replies.” ~ @alyssa_dulin
[19:22] - “Even though reputation issues can be scary, at least at Gmail there are a decent amount of tools, signals that you can use to be able to work on certain aspects of your list and your sending habits, and they give you an opportunity to get better.” ~ @mel_lambert_
Links
- Subscribe to the monthly Deliverability Defined newsletter!
- Monthly deliverability reports
- Starbucks
- Slack
- Gmail
- Hotmail
- Yahoo Mail
- Finances Online report
- Google Postmaster Tools
- Deliverability Defined 0222: Ask Our Experts: Help, My Emails Are Landing in the Promotions Tab!
- Ask Alyssa & Melissa questions or suggest content for our next monthly newsletter!
Connect with our hosts
Stay in touch
Next Episode

How Deliverability Impacts Newsletter Sponsorships
Creators are always looking for a way to earn income through their efforts, which traditionally evolves into sponsorship or brand deals. Of course, creators want to earn this extra income, but they struggle to keep their audiences happy; no one likes to feel like they’re being sold to when reading their favorite newsletter. Is there an option that balances the needs of creators, audiences, and sponsors alike?
One solution is newsletter sponsorship. Creators spend a long time crafting relationships with their audiences to keep them loyal and engaged, and this can pay off for them in the long run once they’ve amassed a following with consistent open rates. Brands with similar target audiences strive to work with creators who have already built their readers’ trust.
In this episode, Alyssa and Melissa discuss what newsletter sponsorship is and how to use it to your advantage. Together, they delve into how newsletter sponsorship differs from email marketing, how sponsorship impacts your deliverability, and why newsletter sponsorship is mutually beneficial for all parties involved.
Key Takeaways
- [04:27] - What is newsletter sponsorship?
- [07:21] - What is the ConvertKit Sponsor Network and who is the target audience?
- [10:26] - How newsletters differ from email marketing.
- [15:14] - What sponsors are looking for when they pay to appear in a newsletter.
- [18:10] - How will your newsletter’s deliverability change once you start introducing sponsorship?
- [23:30] - Why newsletter sponsorship is mutually beneficial for everyone involved.
- [26:40] - What to do when you experience deliverability issues with a sponsor.
Quotes
[12:21] “Another thing that's really awesome about newsletters and sponsors and brands is that you can really clearly help brands find out where they should go to find new customers.” ~ @alyssa_dulin
[20:13] - “The more you can encourage replies and that one-to-one feel in your newsletters, the better chance you have of moving those back to the primary inbox.” ~ @mel_lambert_
[21:24] - “I do recommend making sure that the ad still sounds like it's coming from you, that it visually matches your branding, and then, also, that the copy matches your branding.” ~ @alyssa_dulin
Links
- ConvertKit Sponsor Network
- Athletic Greens
- Petco
- James Clear
- Pat Flynn
- Subscribe to the weekly Deliverability Dispatch Newsletter!
- Subscribe to the monthly Deliverability Defined newsletter!
- Ask Alyssa & Melissa questions or suggest content for our next monthly newsletter!
Connect with our hosts
Stay in touch
Try ConvertKit's deliverability in action
It's now free to use ConvertKit with an audience of 1,000 subscribers or less! Start building your audience and reaching their inboxes: convertkit.com/pricing.
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