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Supa

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Little update on my progress with my newsletter.

I looked at quite a few newsletter tools, Substack, Ghost, MailCheat(Chimp), Revue, and some more. For now I decided to go with ConvertKit.

One of the most important factors for me is that you can easily access the sent newsletter posts online as well, so that they not simply disappear for anyone to read after they are sent, except in the inboxes of those subscribed at the time. So more of a blog/newsletter hybrid.

Set up a little landing page, bought a domain, created a little logo myself and did all the serious stuff like disclaimers, privacy policy and some more things that one needs when running a website in the EU and in Germany.

Currently writing on my first post to publish. Taking me some time but it's going faster and faster, while I already have more posts in the pipeline that I'm working on simultaniously.
 
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MTF

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One of the most important factors for me is that you can easily access the sent newsletter posts online as well, so that they not simply disappear for anyone to read after they are sent, except in the inboxes of those subscribed at the time. So more of a blog/newsletter hybrid.

That was my key factor, too and that's why I went with Ghost. ConvertKit allows you an archive page but the ones I saw were ugly and I don't think they would be even indexed by Google.

Currently writing on my first post to publish. Taking me some time but it's going faster and faster, while I already have more posts in the pipeline that I'm working on simultaniously.

Awesome! Keep us updated.

Is this going to be in English or German?
 

Supa

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That was my key factor, too and that's why I went with Ghost. ConvertKit allows you an archive page but the ones I saw were ugly and I don't think they would be even indexed by Google.
With ConvertKit you can create a landing page and add a newsletter feed to it, so visiters can access your posted newsletters. But yes, Ghost's blog-like look is a lot better. This is supposed to be a temporary solution. I'm preparing to moving the posts as blog posts to a wordpress site and using ConvertKit only for the newsletter itself.

Awesome! Keep us updated.
I will! If I feel good about the first post, maybe I'll post it here :)

Is this going to be in English or German?
The newsletter will be in English.

I'm planning on doing the posts in English and in German as soon as it's on a wordpress site where I can add both more easily.
 

MTF

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Just secured my first YouTube sponsorship / a "brand ambassador" :smile:

I'm really curious whether it will translate into any growth for the newsletter since these are two different mediums.

Still, I think it's a pretty rewarding kind of marketing as you're working directly with a fellow creator instead of a faceless corporation.

Also, I had a plan to hire someone to customize my Ghost theme once I hit 500 subscribers since the website looks basic and perhaps a little cheap. Maybe I'll do it sooner as I think that my opt-in rates could be much higher. A more professional custom brand design would help build more trust and show that it's not just another similarly-looking newsletter.
 
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Andy Black

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Great work @Supa and @MTF.

I like this sort of joint progress thread. I’ve not seen one like this in the forum before. It almost creates a small community within the community.

@MJ DeMarco … are there any other threads that multiple people update with progress? Could this be a thing for the forum?
 

JoeyF

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Just secured my first YouTube sponsorship / a "brand ambassador" :smile:

I'm really curious whether it will translate into any growth for the newsletter since these are two different mediums.

Still, I think it's a pretty rewarding kind of marketing as you're working directly with a fellow creator instead of a faceless corporation.

Also, I had a plan to hire someone to customize my Ghost theme once I hit 500 subscribers since the website looks basic and perhaps a little cheap. Maybe I'll do it sooner as I think that my opt-in rates could be much higher. A more professional custom brand design would help build more trust and show that it's not just another similarly-looking newsletter.
Fun experiment! Hope it goes well!

I'm currently pondering how best to deal with my website, it looks like trash and if it's already getting some organic traffic, I should put some more effort into it and double down on SEO.

90 organic visits in the last 28 days through the long tail keywords I set out last year, not exactly hitting the big time yet but cool to see something happening.
 

Andy Black

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I just sent an email to my handful of subscribers to my new $5/mth newsletter.

It was literally bullet-points of my progress and thoughts growing my business this week. It's like a journal so really easy to come up with the content (although it took time to summarise it so it was easy to read).

I consider that time well spent because it helps me get clarity anyway. It's probably something I should do every Sunday evening.
 
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MTF

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I sent pitches to 17 newsletters on Swapstack, ranging from 21,000 subscribers to just 270. I have a few more, larger newsletters saved which cover broader topics but may potentially work as well (I first want to see how more relevant newsletters will perform).

Update on this:

Just 8 newsletter owners responded:
  1. One newsletter didn't consider it a good fit.
  2. One newsletter approved my pitch and then didn't reply to my questions (I just followed up).
  3. Another newsletter also didn't respond until I followed up. But I'm not sure about this one as it's a very small newsletter and the owner doesn't seem to be particularly interested.
  4. Discussing the deal with one tiny newsletter. Probably doesn't make sense considering low subscriber count and a terribly low open rate.
  5. Tried negotiating with a newsletter that could be a good fit but the newsletter owner changed his prices and charges way too much.
  6. One approved my pitch today and hasn't responded to my questions since (I followed up).
  7. Almost done finalizing a deal with a newsletter with 7,000 subscribers.
  8. One deal with a 9,000+ subscriber newsletter is finalized and ready to go this weekend.
All in all, Swapstack was very promising when I first saw it but now I see it's not as game-changing as I thought it would be. Perhaps it works better for bigger and sexier niches like marketing and tech.
 

Mr. Roboto

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I got inspired by this thread!

I've cleaned up my personal website, migrated old content to other services, and started a publication with Substack which will act as a student newsletter (I have extensive programming knowledge but I'm lacking first-hand experience in other important fields of running a SaaS business).

I'll be sharing my experiences and thoughts on producing a valuable product. It should help me beat multiple birds with one stone. I can market the product, build a personal brand, and monetize newsletter content this way. Substack allows making certain posts available only to paid subscribers. I'll soon share it with my network.

Now my biggest regret is not building a strong and large network earlier. I'll have to start showing up in relevant groups.

I'll share an update soon.
 
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MTF

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I got inspired by this thread!

I've cleaned up my personal website, migrated old content to other services, and started a publication with Substack which will act as a student newsletter (I have extensive programming knowledge but I'm lacking first-hand experience in other important fields of running a SaaS business).

I'll be sharing my experiences and thoughts on producing a valuable product. It should help me beat multiple birds with one stone. I can market the product, build a personal brand, and monetize newsletter content this way. Substack allows making certain posts available only to paid subscribers. I'll soon share it with my network.

Now my biggest regret is not building a strong and large network earlier. I'll have to start showing up in relevant groups.

I'll share an update soon.

That's awesome. I'm happy to see so many people getting inspired by this thread to start creating their newsletters.
 
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MTF

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What an awesome article:

Here are the ones that resonated the most with me:

  • There is no competition for your personal voice.

  • Build relationships. That’s what it’s all about. Anyone trying anything else is lying to themselves or their readers. All you need is one relationship to change or save your project, career, or life. Why not establish more? This is also what separates the wealthy from the successful.

  • New idea? Just start. You can’t establish relationships if you’re not out there. Whatever it takes, get your idea out there now. Course correct, if and when needed. Every failure is possible entertainment for your audience. So, just ship.

  • Keep track of what delights you about other newsletters — not what engages you (that’s too easy — A.I. can do that). Engagement is good for a few sentences. Delight builds anticipation for the next issue. You’re probably not producing enough delight. You probably should be.

  • Subject lines don’t matter anywhere near as much as your From line. Trust is the only thing that improves your From line.

  • Monetization is a byproduct. If you build an audience to serve that audience, monetization will present itself. You don’t need to chase it. You don’t even need to accept it if you don’t want the added responsibility.
 
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Andy Black

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^^^ I love the emphasis about building relationships. Will read the article. Thanks for sharing, and your takeaways.
 

Andy Black

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Ones that resonates with me were:
  • There’s bravery in brevity. Small is considerate, difficult, and valuable. Most books should be a blog post. Most blog posts should be a tweet. Most tweets shouldn’t be.
Shorter is indeed harder to do, and more valuable imo. Loved the “Most tweets shouldn’t be.” 100% agree.

  • Don’t get bogged down in tracking clicks. Respond. People are not “opens.” People are not “clicks.”
Amen. I’ve been saying that for years. Stop calling it traffic.

  • Meet your subscribers. When you meet readers in person, you get a better understanding of how what you do fits in their world. It shapes the way you publish, as well as what you publish.
Get to Zoom as soon as you can. Only the most engaged will want to. You’ll benefit more than they will.

  • When stuck, apply another constraint.
Yes! Constraints are what make us innovate. So long as we see hurdles as stepping stones.

  • Be ready to unlearn in an instant when presented with new information.
This is good advice for business and life.
 
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Roli

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Thank you @MTF for this nugget of gold!
 

MTF

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Update on this:

Just 8 newsletter owners responded:
  1. One newsletter didn't consider it a good fit.
  2. One newsletter approved my pitch and then didn't reply to my questions (I just followed up).
  3. Another newsletter also didn't respond until I followed up. But I'm not sure about this one as it's a very small newsletter and the owner doesn't seem to be particularly interested.
  4. Discussing the deal with one tiny newsletter. Probably doesn't make sense considering low subscriber count and a terribly low open rate.
  5. Tried negotiating with a newsletter that could be a good fit but the newsletter owner changed his prices and charges way too much.
  6. One approved my pitch today and hasn't responded to my questions since (I followed up).
  7. Almost done finalizing a deal with a newsletter with 7,000 subscribers.
  8. One deal with a 9,000+ subscriber newsletter is finalized and ready to go this weekend.
All in all, Swapstack was very promising when I first saw it but now I see it's not as game-changing as I thought it would be. Perhaps it works better for bigger and sexier niches like marketing and tech.

Update on this and a general update later:

I spent $57 on an ad in the only newsletter deal that has worked out so far. Just 5 people visited my website from that ad. As far as I know (my analytics aren't perfect with conversion tracking), nobody subscribed.

So in the end, at least for my niche, Swapstack is a complete waste of time.

50% of newsletters you pitch will ignore you. From the ones that accept the pitch, some will not continue the conversation (so they click a button and then stay silent). Those that respond once will drop the ball after your response. Yes, I could follow up with them but if that's how they treat potential sponsors I bet they also treat their subscribers like shit.

General update

About 6.5 weeks since starting, I'm at 170 subscribers now with average open rate of previous issues at around 60%.

Reddit and this forum are the main sources of growth (that past effective $50 newsletter promo doesn't generate any subscribers anymore but brought about 50 people).

I sent out emails to about 15-20 bloggers/YouTubers/websites that may have a similar audience to mine. I got zero responses even though many of these were email addresses specifically for sponsorship inquiries.

I find it strange that I'm not getting any responses. Feels like my emails don't even reach them. My guess is that they'd rather work with proper big brands.

Edit: right before posting this, I got an email from one YouTuber I emailed today. He asked what kind of promotion I have in mind. And another one (whom I also emailed today morning) replied he doesn't do sponsorships.

I set up Google Ads again on Saturday targeting specific keywords but the ads are still under review.

Other Newsletter Thoughts

I'm tempted to start a curated newsletter in a broad niche that offers more marketing opportunities.

My plan was to launch a new business as a sort of a investment, to add a new asset to my portfolio and diversify myself. But in the case of this newsletter, I can't do that as I have zero sensible options to do that.

I ran into a similar problem with my previous newsletter for vegan athletes. In hindsight, that was way too niche to ever work. I guess I have a talent of coming up with obscure topics lol.

So far my experience building newsletters has taught me that choosing the right topic is BY FAR the most important growth factor.

From my experience exploring the newsletter industry, here are the hottest niches:
  • finance/crypto,
  • tech/future,
  • general curated news newsletters,
  • general "best of the web" curated newsletters,
  • marketing/business.
Everything not on this list, even if otherwise a big niche (for example health/fitness), is way less popular.

I'm pretty sure I could have hit 1000+ subscribers in a big, popular niche already. Just a few ads in big publications would have helped me get there.

For example, if I had a newsletter about the future, I could advertise it in The Futurist. They charge $3,500 for an ad sent to their 760,000 subscribers. Their open rate is 26% and they say the ad has a CTR between 0.4-0.6%. So assuming you have a high-quality relevant newsletter, you pay $3,500 to expose it to about 197,600 people (views) and have between 7,904 and 11,856 people visiting your website.

My current opt-in rate from ALL traffic sources is roughly 10%. I'm pretty sure that for that hypothetical newsletter about the future, with people coming from a very similar publication, that rate would be at least 20-30%, if not more. So by placing just one $3,500 ad I'd acquire between 1,580-3,556 highly-relevant subscribers.

Since these are just theoretical calculations maybe my math is off. But how off could it really be? Even if by 50%, with just a few thousand dollars invested I could have 1000+ subscribers already. This would be enough to create a referral program (a strategy that helped build some big newsletters) and start monetizing the list.
 

Andy Black

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Update on this and a general update later:

I spent $57 on an ad in the only newsletter deal that has worked out so far. Just 5 people visited my website from that ad. As far as I know (my analytics aren't perfect with conversion tracking), nobody subscribed.

So in the end, at least for my niche, Swapstack is a complete waste of time.

50% of newsletters you pitch will ignore you. From the ones that accept the pitch, some will not continue the conversation (so they click a button and then stay silent). Those that respond once will drop the ball after your response. Yes, I could follow up with them but if that's how they treat potential sponsors I bet they also treat their subscribers like shit.

General update

About 6.5 weeks since starting, I'm at 170 subscribers now with average open rate of previous issues at around 60%.

Reddit and this forum are the main sources of growth (that past effective $50 newsletter promo doesn't generate any subscribers anymore but brought about 50 people).

I sent out emails to about 15-20 bloggers/YouTubers/websites that may have a similar audience to mine. I got zero responses even though many of these were email addresses specifically for sponsorship inquiries.

I find it strange that I'm not getting any responses. Feels like my emails don't even reach them. My guess is that they'd rather work with proper big brands.

Edit: right before posting this, I got an email from one YouTuber I emailed today. He asked what kind of promotion I have in mind. And another one (whom I also emailed today morning) replied he doesn't do sponsorships.

I set up Google Ads again on Saturday targeting specific keywords but the ads are still under review.

Other Newsletter Thoughts

I'm tempted to start a curated newsletter in a broad niche that offers more marketing opportunities.

My plan was to launch a new business as a sort of a investment, to add a new asset to my portfolio and diversify myself. But in the case of this newsletter, I can't do that as I have zero sensible options to do that.

I ran into a similar problem with my previous newsletter for vegan athletes. In hindsight, that was way too niche to ever work. I guess I have a talent of coming up with obscure topics lol.

So far my experience building newsletters has taught me that choosing the right topic is BY FAR the most important growth factor.

From my experience exploring the newsletter industry, here are the hottest niches:
  • finance/crypto,
  • tech/future,
  • general curated news newsletters,
  • general "best of the web" curated newsletters,
  • marketing/business.
Everything not on this list, even if otherwise a big niche (for example health/fitness), is way less popular.

I'm pretty sure I could have hit 1000+ subscribers in a big, popular niche already. Just a few ads in big publications would have helped me get there.

For example, if I had a newsletter about the future, I could advertise it in The Futurist. They charge $3,500 for an ad sent to their 760,000 subscribers. Their open rate is 26% and they say the ad has a CTR between 0.4-0.6%. So assuming you have a high-quality relevant newsletter, you pay $3,500 to expose it to about 197,600 people (views) and have between 7,904 and 11,856 people visiting your website.

My current opt-in rate from ALL traffic sources is roughly 10%. I'm pretty sure that for that hypothetical newsletter about the future, with people coming from a very similar publication, that rate would be at least 20-30%, if not more. So by placing just one $3,500 ad I'd acquire between 1,580-3,556 highly-relevant subscribers.

Since these are just theoretical calculations maybe my math is off. But how off could it really be? Even if by 50%, with just a few thousand dollars invested I could have 1000+ subscribers already. This would be enough to create a referral program (a strategy that helped build some big newsletters) and start monetizing the list.
How can you test newsletter ideas quickly?

Can you create simple opt-in pages and then focus on figuring out how to get a constant streams of new subscribers?
 
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MTF

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How can you test newsletter ideas quickly?

Can you create simple opt-in pages and then focus on figuring out how to get a constant streams of new subscribers?

I can set it up super fast with Ghost or maybe even use Carrd instead.

Perhaps I could skip writing any content as well and just book an ad or two on a similar newsletters and see how many people sign-up.

After their sign-up I could redirect them to a simple survey form to learn more about what they're interested in.

Thanks for that suggestion. Going back to the basics.

By the way, that's roughly how this newsletter got started (notice how extremely simple the landing page is):

Here's a great article on how she did it:
 

JoeyF

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Update on this and a general update later:

I spent $57 on an ad in the only newsletter deal that has worked out so far. Just 5 people visited my website from that ad. As far as I know (my analytics aren't perfect with conversion tracking), nobody subscribed.

So in the end, at least for my niche, Swapstack is a complete waste of time.

50% of newsletters you pitch will ignore you. From the ones that accept the pitch, some will not continue the conversation (so they click a button and then stay silent). Those that respond once will drop the ball after your response. Yes, I could follow up with them but if that's how they treat potential sponsors I bet they also treat their subscribers like shit.

General update

About 6.5 weeks since starting, I'm at 170 subscribers now with average open rate of previous issues at around 60%.

Reddit and this forum are the main sources of growth (that past effective $50 newsletter promo doesn't generate any subscribers anymore but brought about 50 people).

I sent out emails to about 15-20 bloggers/YouTubers/websites that may have a similar audience to mine. I got zero responses even though many of these were email addresses specifically for sponsorship inquiries.

I find it strange that I'm not getting any responses. Feels like my emails don't even reach them. My guess is that they'd rather work with proper big brands.

Edit: right before posting this, I got an email from one YouTuber I emailed today. He asked what kind of promotion I have in mind. And another one (whom I also emailed today morning) replied he doesn't do sponsorships.

I set up Google Ads again on Saturday targeting specific keywords but the ads are still under review.

Other Newsletter Thoughts

I'm tempted to start a curated newsletter in a broad niche that offers more marketing opportunities.

My plan was to launch a new business as a sort of a investment, to add a new asset to my portfolio and diversify myself. But in the case of this newsletter, I can't do that as I have zero sensible options to do that.

I ran into a similar problem with my previous newsletter for vegan athletes. In hindsight, that was way too niche to ever work. I guess I have a talent of coming up with obscure topics lol.

So far my experience building newsletters has taught me that choosing the right topic is BY FAR the most important growth factor.

From my experience exploring the newsletter industry, here are the hottest niches:
  • finance/crypto,
  • tech/future,
  • general curated news newsletters,
  • general "best of the web" curated newsletters,
  • marketing/business.
Everything not on this list, even if otherwise a big niche (for example health/fitness), is way less popular.

I'm pretty sure I could have hit 1000+ subscribers in a big, popular niche already. Just a few ads in big publications would have helped me get there.

For example, if I had a newsletter about the future, I could advertise it in The Futurist. They charge $3,500 for an ad sent to their 760,000 subscribers. Their open rate is 26% and they say the ad has a CTR between 0.4-0.6%. So assuming you have a high-quality relevant newsletter, you pay $3,500 to expose it to about 197,600 people (views) and have between 7,904 and 11,856 people visiting your website.

My current opt-in rate from ALL traffic sources is roughly 10%. I'm pretty sure that for that hypothetical newsletter about the future, with people coming from a very similar publication, that rate would be at least 20-30%, if not more. So by placing just one $3,500 ad I'd acquire between 1,580-3,556 highly-relevant subscribers.

Since these are just theoretical calculations maybe my math is off. But how off could it really be? Even if by 50%, with just a few thousand dollars invested I could have 1000+ subscribers already. This would be enough to create a referral program (a strategy that helped build some big newsletters) and start monetizing the list.
Brilliant update. It's quite inspiring to see how you're working your way through the ups and downs of getting a newsletter off the ground, testing new things and sharing results here.

Got me fired up reading this.

Cheers
 

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How can you test newsletter ideas quickly?

Can you create simple opt-in pages and then focus on figuring out how to get a constant streams of new subscribers?
I like this idea a lot, this would be really stacking the deck in your favour I feel.
 
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JoeyF

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I'm still working on my newsletter idea/format.

I've now written 3 newsletters in total - content curation with commentary style.

I'm trying to figure out a way to do this where it's fun to write for me and I'm not quite there yet.

The way I see this working is, If I can get to a place where I have fun writing the newsletter and there is strong interest in the topic for the reader, that's where the magic will happen.

But it has to be fun to write otherwise I know I'll struggle to keep it going and really invest the time and effort into making it a great newsletter.

I'm going to experiment with some other avenues of attack this week on the same subject matter to see if I can make it a bit more fun both to write and read.

What makes writing your newsletter enjoyable?

Is it giving your thoughts in your own style?
Working on your writing and seeing that improve?
Knowing you're delivering value and building relationships?
Entertaining people?
The subject matter is super interesting to you?
 

Andy Black

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You guys might find this useful:
I think you’re goal is to figure out a channel/funnel and product/money nozzle to go on the end of that funnel.

I personally don’t even write welcome emails till someone signs up, and then I send a personalised video welcome. That way I’ve spent the minimum amount of time writing stuff no-one will see.
 

Andy Black

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I'm still working on my newsletter idea/format.

I've now written 3 newsletters in total - content curation with commentary style.

I'm trying to figure out a way to do this where it's fun to write for me and I'm not quite there yet.

The way I see this working is, If I can get to a place where I have fun writing the newsletter and there is strong interest in the topic for the reader, that's where the magic will happen.

But it has to be fun to write otherwise I know I'll struggle to keep it going and really invest the time and effort into making it a great newsletter.

I'm going to experiment with some other avenues of attack this week on the same subject matter to see if I can make it a bit more fun both to write and read.

What makes writing your newsletter enjoyable?

Is it giving your thoughts in your own style?
Working on your writing and seeing that improve?
Knowing you're delivering value and building relationships?
Entertaining people?
The subject matter is super interesting to you?
What if it wasn’t you doing the writing?

What if you found a topic and channel that brought a consistent stream of new subscribers, where many have money to burn. Would you discount it or consider hiring a content writer or buying content?
 
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JoeyF

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You guys might find this useful:
I think you’re goal is to figure out a channel/funnel and product/money nozzle to go on the end of that funnel.

I personally don’t even write welcome emails till someone signs up, and then I send a personalised video welcome. That way I’ve spent the minimum amount of time writing stuff no-one will see.

I do think this is a great way forward, if you're confident you'll enjoy writing about the things you're testing.

My issue right now is, I feel I really need to do some internal work of my own, testing out writing some content, to see what I actually enjoy writing about.

Otherwise, having an audience or not, it's not going to work.

Then I can start running some real world tests where I send traffic to landing pages to see what the final form hook of my newsletter will be.
 

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After their sign-up I could redirect them to a simple survey form to learn more about what they're interested in.
Personally, I’d send a personalised 30 second welcome video via email. They then know it’s not some clever auto responder, and many will be surprised and delighted to hear from you and get in early. Then you can get into email conversation and learn more about them and what they want. Get to Zoom and enjoy meeting people, and seeing your avatar come to life.

Surveys can help, and I’ve even used them myself, but I think engaging is better than surveying.
 

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What if it wasn’t you doing the writing?

What if you found a topic and channel that brought a consistent stream of new subscribers, where many have money to burn. Would you discount it or consider hiring a content writer or buying content?
Interesting idea for sure and it has crossed my mind.

Shaan Puri (partner of Sam Parr on MFM podcast) has just started a new web3 newsletter.


His strategy was to partner up with someone who is equally passionate and the partner writes the newsletter and Shaan edits it.

It's going really well.

I had an idea initially to recruit some volunteers to provide little bits of content for this newsletter and for me to focus more on pulling it all together and doing the marketing.

It's a topic where finding people interested in contributing would probably be fairly easy so I will give this idea some more thought.
 
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Interesting idea for sure and it has crossed my mind.

Shaan Puri (partner of Sam Parr on MFM podcast) has just started a new web3 newsletter.


His strategy was to partner up with someone who is equally passionate and the partner writes the newsletter and Shaan edits it.

It's going really well.

I had an idea initially to recruit some volunteers to provide little bits of content for this newsletter and for me to focus more on pulling it all together and doing the marketing.

It's a topic where finding people interested in contributing would probably be fairly easy so I will give this idea some more thought.
Yeah. Lots of people like writing but don’t know how to create an audience and/or monetise. If you do the business and marketing side then I imagine you’d have your pick of writers.
 

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Brilliant update. It's quite inspiring to see how you're working your way through the ups and downs of getting a newsletter off the ground, testing new things and sharing results here.

Got me fired up reading this.

Cheers

Thank you. I'm honored to hear that it fired you up.

I love how this thread turned into a joint progress thread as @Andy Black mentioned. I have a few progress threads on the forum and they're very me-focused. This thread is cooler because we get to try different things together, post updates, and inspire each other.

By the way, if there are any lurkers in this thread (hi!) come forward and introduce yourself. You have nothing to lose. Start your newsletter if you're on the fence and learn as you go.
 

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I'm trying to figure out a way to do this where it's fun to write for me and I'm not quite there yet.

The way I see this working is, If I can get to a place where I have fun writing the newsletter and there is strong interest in the topic for the reader, that's where the magic will happen.

But it has to be fun to write otherwise I know I'll struggle to keep it going and really invest the time and effort into making it a great newsletter.

I can relate to that. In general in business perhaps you shouldn't chase passion but IMO in writing, if you can't have at least some fun doing it, it just isn't going to work.

This is particularly important if you're building a mostly solopreneur kind of a business where you don't plan to ever hire someone else to write it for you. Most writers/writers-entrepreneurs don't want to do that.

What makes writing your newsletter enjoyable?

Is it giving your thoughts in your own style?
Working on your writing and seeing that improve?
Knowing you're delivering value and building relationships?
Entertaining people?
The subject matter is super interesting to you?

For me and my current newsletter:
  • Voluntary discomfort has been a part of my life for many, many years. I don't see myself ever not doing it because whenever I take a break, my life gets worse.
  • It's an excellent way for me to contemplate my own self-improvement, particularly since all my articles so far are based on specific quotes from books (that makes it more enjoyable to write than if I were to provide just my original thoughts).
  • It fills a gap for my target audience. So far I haven't found anything aimed at self-improvement for men that wouldn't be about pick-up/dating/sex, fashion, gadgets, or toxic masculinity. The only exception is www.artofmanliness.com but they tend to be quite conservative in style and for older readers.
  • It helps me remember better what I learned from the books I read. I also enjoy sharing quotes from these books with other people.
  • I like inspiring my male friends to get uncomfortable. The newsletter lets me do that on a larger scale (although most of the time I can't see the results with my own eyes as I can when I push my friends face to face).
  • Potentially it will help me network with some men I inspire. That would be an incredible bonus.
  • I think that many men these days struggle with lack of purpose/depression/apathy and similar mental issues. I know for a fact that discomfort can help them feel better. So if I can help turn someone's life around, this is how I can provide real value.
 
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What if it wasn’t you doing the writing?

What if you found a topic and channel that brought a consistent stream of new subscribers, where many have money to burn. Would you discount it or consider hiring a content writer or buying content?

I understand where you're coming from and I think you see it this way because you first describe yourself as an entrepreneur/people helper and not as a writer. For writers the thought of not doing the writing is akin to telling an entrepreneur "what if it wasn't you creating the business?"

Personally, I’d send a personalised 30 second welcome video via email. They then know it’s not some clever auto responder, and many will be surprised and delighted to hear from you and get in early. Then you can get into email conversation and learn more about them and what they want. Get to Zoom and enjoy meeting people, and seeing your avatar come to life.

Surveys can help, and I’ve even used them myself, but I think engaging is better than surveying.

I may consider some Zoom calls. Video welcomes are too much for me (I suck at video and don't want to invest my time into it).
 

Andy Black

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Video welcomes are too much for me (I suck at video and don't want to invest my time into it).
Do you FaceTime people via your phone? If it’s not as simple as that then I contend you’re doing it wrong.

I only mention video because it’s obviously genuine rather than an autoresponder. People are often genuinely surprised to get them, even though they’re 20-30 seconds of me saying hello, waving, telling them what to do, and then asking how they found out about the course/newsletter/etc.

If you can do that via a personalised email then I think that’s just as good, maybe better (as they don’t have to click to watch). I’d look at the website associated with their email and comment on it, or ask them about their cool name or something. Again, people would reply as they were surprised they got a real email.
 

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