The little-known secret to selling $250,000 worth of ads in 60 days

Without any prior experience

Guest Deep Dive

The little-known secret to selling $250,000 worth of ads in 60 days — with no experience

 Today’s deep dive is a guest post from Wouter Teunissen.

Wouter is the founder of and previously was the top ad salesperson at The Milk Road.

Wouter will take over writing from here…

SMASH. I slam the door.

I throw my bag on my bed in disappointment.

I'm home again after another long dark winter day at University…

Home again with nothing to show for it. I flip open my laptop as usual, itching to do something with my life. My leg shaking like a fiend waiting for his next hit.

My eyes start scanning Twitter like a hawk tracking his prey. Except there's no pray. I'm just scrolling...

Like Caesar crossing the rubicon, a single action, a single tweet would change history.

Well at least for me and you. You see without that one tweet, I would not be here. You would not be reading this. And my life would certainly be different, I'd probably still be behind that laptop. Itching. Waiting. Watching.

But what was the tweet? It was so simple.

Popular entrepreuner/podcaster Shaan Puri, who at the time was running the Milk Road newsletter just posted the Milk Road’s first video on YouTube.

Respectfully, the video’s thumbnail sucked. And for some reason I decided to tweet that thought out to Shaan, thinking nothing of it.

I went to the toilet, I get back, and I see a little blue notification. He replied!

They liked my unsolicited feedback. So, I got an internship to work there. What followed was 4 months of intense, varied, and difficult work.

I had never done something like this before, I was like Jon Snow. I knew nothing.

After months of hustling helping grow the newsletter, another opportunity arose. The Milk Road needed a salesperson. I remember reading the message in Slack, I crafted a text saying I would be the perfect person.

I sat on my chair, sweat pouring down the side of my torso (literally), and clicked.

Message sent.

What followed was me learning -- on the go -- how to sell over $250,000 in advertisements whilst studying full time within 60 days, working 24/7 around the clock.

After having sold $1,000,000+ worth of newsletter advertisements, it's crazy to say but my life changed because of newsletters.

Today people refer to me as the 'messi' of newsletter advertisement sales.

I'd not go that far, but, after having sold millions of dollars of ads, I know a thing or 2 about selling.

Matt has given me the opportunity to write a guest post here highlighting some of the things I've learned. And hopefully, this is something useful to you.

Now listen up, here are the topics I'm going to cover.

These are all secrets that I've learned through blood, sweat, and tears of selling my ass off.

These are the 4 secrets to getting your newsletter to generate (significant) revenue.

1. Are you worth it?

Before you can start selling advertisements, you gotta be real wit yo self.

Does anyone even want to advertise in your newsletter?

Think about it this way, you're walking through a street of shops. Would you walk into the shop that is empty?

The store with an empty storefront and one guy eagerly asking you to come in with a weird Swedish accent?

OR the shop that looks beautiful, the lighting, and the products are all cleanly displayed.

The newsletter that sucks -- hopefully not yours -- is the one begging people to come in.

The newsletter that wins -- hopefully yours! -- is the one that is clean, attractive, and worth going inside.

So. Are you even worth it?

Ask yourself if the following applies to you:

  • You should have a well-defined audience(e.g. newsletter operators).

  • You should have a well-defined value prop (e.g. reach founders of newsletters).

If you can't articulate these two points, you gotta go under a tree and do some thinking like the Buddha.

And then once you've found enlightenment, you can go ahead and prepare the groundwork to sell like crazy.

You're going to need a media kit first.

  • Here is an example of a phenomenal media kit - TLDR media kit - (linked here)

You're also going to need simple infrastructure in place.

How are you collecting leads? Tracking conversations? Tracking revenue?

Honestly, Google Sheets and Typeform as your tech stack is fine. Just make sure you're tracking your KPIs somewhere. That's the most important thing.

Why should you track this?

That's like asking someone if they need an umbrella if they go outside.

How do you know if you need one -- You look outside the window! 

If the window doesn't exist, and it's just a brick wall. You don't know if you need an umbrella or not...

That's a bad situation to be in (trust me I'm Dutch I know the pain of a rainy day). 

So tracking your KPIs is like having that window, you look at it and you can see if you need to fix something, grab an umbrella, or panic.

Things that I like to track are;

  • Revenue per newsletter

  • Fill Rate (% of upcoming newsletters in 30 days that are sold out)

  • Churn (how many advertisers return month over month)

  • Leads in the pipeline (# of people you're talking to)

Publish these consistently in your team channels.

You should feel a maniacal sense of urgency to have these KPIs looking great at all times. If that's not something you want to do, or someone on your team wants to do, you can click off this newsletter now.

Anyway, most of the above things are table stakes to organize, but necessary.

Now as Anakin Skywalker once said, this is where the fun begins....

2. So you wanna be a legitimate newsletter publication. Who cares?

The most important thing for sales is that you know better than anyone who should be a great fit for your audience.

You are like a doctor, you're consulting the patient on why their needs are served by sponsoring your newsletter.

So if you don't have a degree in knowing everything about your audience, you better start gathering data! Otherwise, how can you advise your clients?

Now the most important step in any process is step one. Step one in any sales process, is knowing who you should contact.

Most importantly that’s knowing;

  • What is this person’s job title?

  • They should be a decision maker, depending on the size of the company you might want to message the CEO. Or maybe not, at bigger companies you will want to contact folks who have titles like: Demand Generator or Paid Marketing Manager, etc.

  • Who is this person?

  • Try to figure out what kinda person this is. Do a bit of diggin' and figure out what they like and dislike. Do they have an unexplainable hate for basketball? Don't bring it up! Or vice-versa.

Once you have the information on who you should reach out to, here are the ways you should contact them.

I'll get to how I do exactly this in the next section, but first know that:

You should be reaching out through multiple channels to your target prospects. LinkedIn, Twitter, and of course email.

I've even heard that in specific niches (like sports newsletters) that Instagram works wonders too.

Figure out where your folks are, and find them there. I sold over $100,000+ worth of ads via Twitter. DON'T overlook any channels!

Once you've sent a message, you should be following up multiple times AT LEAST. I've messaged leads well over 10 times before getting a reply. If I would have stopped at my 2nd. 3rd. or 5th email I'd not have closed a lot of sales.

Even previous advertisers have said that relentlessness is something their teams need. As long as you're polite, not rude, and providing value in each message you send. You can cut through the noise.

The key is to provide value in each message you send.

Don't just say "bump", "bump", "bump".

You're not a car going over speedbumps.

You're an authority on newsletters. And you're here to help sponsors look great.

3. The Magic Tool I Use To Generate Revenue (on easy mode)

High and Quality Volume is necessary for newsletter sales.

That's why I am building the most comprehensive sales tool for newsletters. You can easily find, contact, and close companies who are actively advertising in newsletters through Open Rates real-time database of 10,000+ sponsors

Within just a few weeks of signing up, someone has closed a $20,000 deal because of our platform.

Using this tool myself, I sold thousands of dollars worth of ads too.

4. The Four Principles Of A Poor Man

I'm going to give you four sales principles I advise you to live and die by.

These are the four principles of a poor man because without them you're going to highlight incredibly poor business practices. And if you're not careful, will end up being the poor man.

So embrace these principles, and think of yourself as the poor man so that you avoid his mistakes.

  1. Avoid ___ in your cold emails

  2. Watch out for these ___ Red flags ALWAYS

  3. Protect ___ , where possible

  4. Stay ___

1) Avoid these things in your cold emails.

  • Do not be long in your message.

  • Do not repeat yourself.

  • Do not be boring.

Make sure you follow AIDA, and have your subject line smoothly flow into your first sentence.

What is AIDA? It’s the structure your email should follow (from the top down)

First, grab your reader’s Attention with a great subject line and preview text.

Then peak their Interest by mentioning a stat, a comment, or a fact that will make them make the 👀emoji.

Then follow up with something that this person Desires (more sales, more subscribers, etc), this must be a desire you / your newsletter can act on.

Finally, get your reader to take Action, by replying to you for example. 

2) Watch out for these 3 red flags in clients

You don't want to work with everyone.

Just like you are selective with who you target for your subscribers, you should be careful with sponsors too.

Watch out for these 3 red flags:

  • The customer/advertiser agrees way too quickly to a deal. This means they don't know what they're talking about or don't have the authority to do the deal.

  • Customers who do not know what they want to promote and why. If they can't articulate this (even after your help) you can't resell them in the future because there is no benchmark for what they want. So you can't track success.

  • If someone is difficult to sell and is erratic and odd. They will be difficult to work with and will come back to bite you in the ass. Either by not paying, asking for extra ad slots, or worse...

3) Stay protected. Always (shoutout Durex, no Magnum)

  • Use Insertion Order Agreements (template here) to protect yourself (assure advertisers you won’t scam 'em).

  • Note: This is not as good as getting paid upfront. I’ve had someone sign a $30k deal and pull out…

  • Practice good cash management - get paid upfront.

4) Stay Humble

Popular rapper Kendrick Lamar was talking to YOU when he said stay humble.

Remember at all times that:

  • Your content IS the main thing. Ensure it delivers, always. Even on Sundays because you're not lazy like the post office.

  • BE clear on your value proposition and deliver to advertisers. Didn't perform? Had no emails sent on the day you should've? Fix it!

Your reputation is the way you work with advertisers. Make it easy for them to come back or tell their peers about you.

I closed a $50,000+ deal because a guy I sold to at a large company liked working with us so much that they recommended us to another department.



And there you have it – the journey from a tweet to transforming my life.

Those are my secrets that propelled me from a university bachelor student to a master of newsletter ad sales.

Remember, it's not just about knowing the tricks of the trade; it's about the relentless pursuit of excellence and the willingness to dive headfirst into challenges.

Whether it's crafting the perfect media kit, mastering the art of the cold email, or using tools like Open Rates to streamline your process, success lies in the details.

I hope my story and these insights inspire you to take your own leap. To look at every tweet, every opportunity, not just as a passing moment, but as a potential turning point.

Because sometimes, all it takes is a single tweet to set you on a path toward rewriting your own history.

Thank you, Matt, for this opportunity to share my story with your audience.

And to all the readers, I encourage you to explore to amplify your newsletter's revenue.

Back to Matt McGarry…

Thank you, Wouter for writing this post!

If you enjoyed this make sure to:

  • Follow Wouter on Twitter

  • Join his newsletter on how to sell ads

  • Find, contact, and close companies who are actively advertising in newsletters with


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