Finding Hidden Profit In Your Email Newsletter — Lesson Nine

Tobin Slaven
Apr 29, 2017 · 8 min read

Other Ways To Monetize Your Newsletter

This is part NINE of TWELVE lessons in the Finding Hidden Profit course on Skillshare. You will also find links to each of the 12 lessons in the video notes.

Please note: If you are NOT currently a Skillshare member, here is my link [I am an affiliate partner] for a free 30-day trial (more than enough to take the full FHP course and any of the other 15,000+ courses available) on

The Big Five Ways To Monetize Your Newsletter

This post for Lesson Nine includes a overview of the different ways people are earning income with their newsletters. If you want the breakdown of what the numbers actually look like, you can review this epic blog post (3,000 words) at where I go into more details than I will cover here.

So without further ado… let’s talk about five different ways you can earn a side income (even replace your current job) by developing the 3rd of the essential pillars — Pillar C:

Idea #1 — Attaching A Newsletter To An Existing Business

This one wasn’t covered in the Lesson Nine video, but my guess is that anyone who is already on the entrepreneurial path will see the opportunity of adding a newsletter and second income stream to an existing business.

We have already talked about how most businesses use email marketing, but they just barrage their customers with salesy emails and honestly, it is not a great experience. It is where the description of spamming people came from.

But if I had a traditional business — a Main Street merchant for example, I would create a newsletter about what is going on locally and of interest to my customers.

Yes, I would sprinkle in news and updates about my store and most readers would understand that. But if you are talking about local events and even other businesses, all of a sudden you become an authority in your local market and a great resource for the local shoppers.

So there is no doubt that a newsletter, developed on a subject related to yor existing business, can help drive additional sales and you won’t have to pay for advertising ever again. But make sure you focus on content that your readers want to know, not just what you want to talk about.

Idea #2— Affiliate Marketing

In the last lesson, we talked a lot about Affiliate Marketing, the creation of a Soap Opera Series, and the Sub-Soap Opera Series that engages with people on the problem, not getting salesy about a product.

I previously share Andre’s Chaperon as a great example of someone who uses this strategy, and makes a full-time living both selling his own training programs and affiliate offers for others.

Key Takeaway: It is important to remember that email newsletters work because people forget quickly. So even if they find a great website, they get busy with other things. That is why it is so important to constantly rebuild that relationship, just like making deposits in a banking account.

Every time you extend an affiliate offer, you are making a withdrawal from that same relationship account. So don’t over do it — or at least make sure you are depositing more (value bombs) than you are withdrawing. You will know if you have gone to far, if you start to see a lot of unsubscribing from your list.

Idea #3 — Sponsors

Taken from the traditional world of advertising, the idea of adding sponsors for creative work is not a new one. Look at podcasting for example. There are several different websites (Midroll for example) where they will help you place sponsors in your work — for a fee.

Often times, you need a big audience (in the case of Podcasts, 25,000+ downloads to get started) before they will work with you. But one of my friends recently started up his new newsletter and he already has a dozen sponsors who are eager to support his new and innovative project.

So don’t be afraid to ask…

To my knowledge, I have not yet seen a website that does the same thing for newsletters, but you would probably be giving away more money than needed. (sign up for any of their newsletters) or Hacker Newsletter are examples of newsletters that regularly maintain a slot for sponsors of each edition. The money that can be earned grows as your audience grows.

Jason Calacanis of Inside is famous for using what he calls white-listed advertising. That means that because he owns the creative decisions, they will not sell sponsorships to any product or advertiser that they don’t fully endorse. They have the advantage of having built a robust audience. But you too may be able to do this — at least within your specific niche or interest.

Share the good stuff with your readers, and they will not mind seeing a sponsored post on occasion. Mark them as sponsored, so your readers know. You can even add a “this week’s newsletter is sponsored by…” section at the end of your newsletter.

Idea #4— Classified Ads

Classified Ads sound a lot like Sponsors, in that someone is paying to be seen and promoted to your audience. But while a sponsor might pay hundreds or even thousands of dollars for multiple newsletter, a classified ad is smaller in scope and placed for each edition.

I don’t see as many newsletters using this format, but as a reader I really like the experience because often times the classified ads can be as interesting as the curated content.

One person who is doing this in a really interesting way is Ann Friedman. But if you like this model, look at this page which shows how she sells her classified ads each week. is a curated newsletter platform, which is software to help you build and send your newsletter each week. I have not used Curated myself, but they have one feature that I REALLY love and that is a board you can update and show what sponsorship or classified ad slots are available.

Idea #5 — VIP Members and Patreon

There is one last revenue model to talk about and it is a doozy. If you can get this one right, your newsletter income can rocket past your highest expectations.

The trick is to figure out if you are sitting on information that is so valuable, people will pay for insider access.

In the VIP Member model, you actually build and send two different newsletters. The first goes to your free subscribers and it really used to build your relationship with many. The second newsletter has some of that same content, but you hold the very best back for your paying members. And they are the only ones who receive the paid version.

Which brings me to one of my favorite newsletter stories — the story of Scott’s Cheap Flights.

You can listen to a great interview from Chris Guillebeau on Side Hustle School (where I learned about Scott’s newsletter), but here are the high points:

  • Scott Keyes is a D.C. based political analyst, who for fun learned that he was really good at sourcing amazing deals on airline flights
  • He started sharing those deals with family and friends (in his spare time)
  • More and more people wanted in on the action…
  • He now boasts over 500,000 subscribers, over 30,000 paid subscribers for his premium newsletter, and his business generates over $1.5MM each year — which as you can imagine, is now his full time job!

And the best part is, Scott is still doing what he loves to do most (guess we all have a nerdy side) because he spends a big chunk of his day — finding great deals on flights all around the Globe.

One Last Key Takeaway: There is also a website called Patreon. Are you familiar with it?

Patreon is a platform for helping you cultivate and serve the people who love your work so much, that they are willing to support it financially. Normally this happens with tiny micro-payments (less than $10) each month.

But they add up fast…

I didn’t have a great example of a newsletter that is killing it with Patreon. I am sure there is one, I just haven’t found it, yet.

But I wanted to share this because it is near and dear to my heart.

You see, I received an ukulele as a birthday present (thank you to my beautiful, generous wife) and I have been learning songs on YouTube.

My favorite channel to learn from is a talented lady named Cynthia Lin, who teaches in real life too, but she has dozens of tutorials on YouTube. They are awesome. And for free!

Well, when Cynthia kicked in her own Patreon account, she now has over 750 supporters, and earns several thousand dollars each month. It is worth looking at her account because you can see how she regularly engage with her audience there, and even let’s the paying supporters choose her next tutorials.

So do you see what is happening there? Yes, the example is from YouTube, but the process looks a lot like Finding Hidden Profit in your email newsletter.

  • Give good stuff for free to build awareness and a relationship
  • Give even better stuff to the people who support you
  • It doesn’t take a lot from each, but a lot of supporters adds up to what can be a significant income, and one that enables you to do more of what you love to do.

I will never be as talented as Cynthia on the uke (trust me, I feel like I have fat, slow fingers). But I do love seeing examples of people earning money and creating value from their passions.

And if Cynthia Lin ever sees this (I know this is a long shot), but I would LOVE to do your newsletter for you! We could feature your latest songs and tutorials, but let’s surround it with other great news and updates (like Ukulenny) from the world of four strings!

Just saying… it would be an awesome newsletter and if someone else out there wants to create one, I will be your first subscriber.


Your homework for Lesson Nine is to go back to your homework from Lesson Two, and think about who your audience is in one sentence. Now let’s (like in Lesson Six) make a list of 10 businesses, products, or services that your people would love to know about. These could be your first sponsors!

If you can’t come up with 10, then make a list of 20.

And one great way to build relationships with these potential sponsors, is to invite them to be listed as a sponsor for little or no money as you are getting started. It makes your newsletter look good (oh, wow — they’ve got sponsors) and builds goodwill.

Remember, I told you about my friend who STARTED his newsletter with a dozen or so sponsors, and they were happy to be seen as supporting a new venture and one that would matter to the local community.

This was part NINE of TWELVE lessons in the Finding Hidden Profit course on Skillshare. You will also find links to each of the 12 lessons in the video notes.

Please note: If you are not currently a Skillshare member, here is my link [I am an affiliate partner] for a free 30-day trial (more than enough to take the full Finding Hidden Profit course and any of the other 15,000+ courses available) on

And if you would like to see an example of my own, personal-branded newsletter called [Tobin Today] you can subscribe here (sent each Thursday morning):

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